Between $300,000 - $400,000 Winter Haven FL Real Estate, Homes, Condos for Sale

4 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code

Under Construction. Introducing the Crestview floorplan, a unique two-story all block construction home available in Villamar, one of our communities in Winter Haven, Florida. Inside this 4 bedrooms, 3-bathroom home you will find 1,866 square feet of desirable living. As you step through the foyer you are greeted with a well-appointed kitchen that features an island with bar seating, cabinets for storage, quartz countertops and stainless-steel appliances. The kitchen overlooks the dining room, living room and outdoor patio making entertaining guests or enjoying time with family easy. The first floor also features a powder room. Perfect for keeping your privacy during guest visits. The second floor is complete with the primary bedroom, three additional bedrooms, a loft, and the laundry room. The primary bedroom includes its own bathroom with a dual vanity sink, separate shower and spacious walk-in closet. Like all homes in Villamar, the Crestview includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

6059 Navona Way, Winter Haven

$336,990

5 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code

Under Construction. The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

6055 Navona Way, Winter Haven

$360,000

5 Beds ⋅ 3 Baths ⋅ Buckeye Rdg SubDv. ⋅ 33881 Zip Code

Welcome to 4230 Roberta Drive in Winter Haven! This spacious single-family home offers 5 bedrooms, 3 bathrooms, and approximately 2,616 sq ft of heated living area, providing plenty of space for comfortable everyday living. The home features a functional layout with the primary bedroom located upstairs, central A/C and heating, and a 2-car attached garage. With generous living spaces and a practical floor plan, this home offers plenty of possibilities to make it your own. Seller is offering up to $10,000 toward buyer’s closing costs, subject to agreed-upon terms. Enjoy the benefit of a remarkably low association fee of only $275 per year. Conveniently located in Winter Haven with access to shopping, dining, services, and everyday conveniences. A great opportunity to make this property your next home. All information is deemed reliable but should be independently verified by buyer and buyer’s agent.

4230 Roberta Drive, Winter Haven

$345,000

5 Beds ⋅ 3 Baths ⋅ Inman Grvs Ph 2 SubDv. ⋅ 33881 Zip Code

Discover the perfect family lifestyle at 930 Cattleman St, located in the Inman Groves community of Winter Haven, Florida. This Lennar Boston model features a modern and spacious layout with 5 bedrooms and 2.5 bathrooms, ideal for those looking for comfort and plenty of room to grow. The first floor features an open-concept kitchen that seamlessly connects to the living area, creating the perfect setting for family gatherings and entertaining. It also includes a versatile flex space that can be used as a formal dining room, home office, or playroom. Upstairs, you’ll find all five bedrooms, including a spacious primary suite with a private bathroom and walk-in closet. The home also offers the added convenience of a two-car garage. With a generous backyard and convenient access to shopping, schools, and major roadways, this home offers an excellent combination of peaceful living and connectivity. Don’t miss the opportunity to live or invest in one of Winter Haven’s growing areas!

930 Cattleman Street, Winter Haven

$350,000

3 Beds ⋅ 2 Baths ⋅ Homewood Sub SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to 117 Homewood Drive in Winter Haven! Situated on a spacious .36-ACRE LOT, this 3-bedroom, 2-bath home offers 1,762 square feet of heated and cooled living space, a versatile BONUS ROOM, screened-in POOL, FENCED backyard, and plenty of space for indoor and outdoor living. Inside, the family room features a wood-burning FIREPLACE, while the kitchen is equipped with new stainless-steel appliances. The bonus room provides additional flexibility for a home office, hobby room, playroom, or additional living space. Step outside to enjoy the screened-in pool, outdoor kitchen area, and recently RESURFACED back patio—an inviting setup for entertaining or enjoying Florida's year-round outdoor lifestyle. The fenced backyard also features a 5-year-old STORAGE SHED with a roll-up door and electrical access, providing convenient space for storage, equipment, or projects. Numerous recent improvements add to the home's appeal, including a NEW ROOF in 2023, A/C replaced in 2024, NEW WATER HEATER, NEW POOL PUMP & MOTOR, new stainless steel kitchen appliances, a resurfaced back patio in 2026, and an updated garage with TESLA charger that conveys. With .36 acres, a screened pool, bonus room, outdoor entertaining space, fenced yard, and substantial storage, this home offers plenty of versatility. Conveniently located with easy access to the Polk Parkway, shopping, dining, and other Winter Haven amenities. Schedule your private showing and experience all that 117 Homewood Drive has to offer!

117 Homewood Drive, Winter Haven

$319,999

4 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code

Under Construction. Azure BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the open-concept layout. The kitchen shines with quartz countertops and all-new stainless-steel appliances, overlooking the dining area and patio. A convenient half bath is located downstairs for guests with a spacious laundry room upstairs. Upstairs, you’ll find all four bedrooms, including the expansive owner's suite with a walk-in shower, double vanities, and a spacious walk-in closet. A flexible recreation space upstairs provides an ideal spot for family gatherings. With a smart thermostat ensuring energy efficiency and comfort, the Azure seamlessly blends functionality and modern luxury. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5369 San Pietro Drive, Winter Haven

$340,000

3 Beds ⋅ 2 Baths ⋅ Summit East Ph 02 SubDv. ⋅ 33884 Zip Code

Beautifully maintained 3-bedroom, 2-bath pool home in a quiet Winter Haven community with a low HOA of $260/year. This home offers extensive upgrades, modern finishes, and a bright, open layout designed for comfortable living. Major improvements include a new roof (2020), new AC (2020), tankless water heater (2021), updated windows (2018), Culligan water system (2016), and a new pool pump and filter (2025). The kitchen features granite countertops, stainless steel appliances, a breakfast bar, and excellent natural light. The bathrooms also include granite counters, updated fixtures, and a large tub in the primary suite. Paradise Walk in tub (2020) in second bathroom. Enjoy Florida living with a saltwater fiberglass pool, screened enclosure, covered patio, fenced yard and irrigation system. Interior highlights include multiple flex spaces, neutral paint, updated ceiling fans, clean flooring, and move-in ready condition. Located close to shopping, dining, medical facilities, Legoland, and major highways, this home offers strong value with thoughtful upgrades and excellent maintenance. Schedule your private showing today.

7002 Summit Circle, Winter Haven

$330,000

2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code

CDD DEBT BALANCE PAID IN FULL*** DESIGNATED GOLF CART ENTRY/GARAGE (9x18) *** FLORIDA ROOM (10X30) ** EXTENDED SCREENED ENCLOSURE(15x30) ** ROOF REPLACED 2022** **Three (3) Windows Replaced in 2023** ** EXTERIOR OF THE HOME PAINTED IN 2021*** and DEDICATED UNSCREENED PAVER AREA FOR YOUR GRILL. This Bali Floor Plan with 2 Beds/2 Baths offers 1,484 sq.ft. living area PLUS 300 Sq. ft. living area in the Florida Room with Tile Floor and Air Conditioning. Grab your Binoculars- You're going to enjoy the nature views of the pond, golf course and wooded area while you relax on the back lanai. The Double Glass Door Entry opens into the heart of the home, the Living Room area. The Guest Bedroom and Bathroom are on the Right, Front of the Home. The Guest Bath features a Shower/Tub Combo and a pocket door provides privacy for overnight guests. A dedicated Linen Closet is in the hallway that leads to the Guest Bedroom/Bath. The Kitchen offers 42" cabinets, granite countertops, breakfast bar, reach in pantry and dinette area. The Living Room, Kitchen and Dinette areas have Crown molding and Tile Floors. The triple sliding glass door system in the Living Room and Double sliding glass door system in the Dinette create a wide, unobstructed opening to the Florida room, offering flexible ventilation, abundant natural light, and a seamless connection. The Florida Room could be used as a Craft area, additional Sitting area with TV or even a Bedroom room for Guests. You have Options! Make the Most of the Space!!! The Primary Suite offers His/Her Walk in Closets and En-suite with Tiled Shower, Vanity with Dual Integrated Sinks and Linen Closet. This attractive home has a 2 Car Garage (19x20) and Separate Golf Cart Garage. The Garage Doors have glass inserts for additional light into the garage and add to the Curb Value of this Home with Paver Driveway and Flagpole. The well-maintained lawn has an irrigation system and custom curbing outlines the landscape beds with rock mulch. Lake Ashton is a 55+ community with Resort Style Amenities, Planned Activities like Dances, Trivia, Day trips, Entertainment series, Holiday Events and MORE! The residents in Lake Ashton enjoy Outdoor and Indoor Swimming Pools, 2- Golf Courses (Memberships are Optional), 2 - Clubhouses, Pickleball, Tennis, Racquetball (Indoor), 1/2 Court Basketball (Indoor), Billiards, Bowling Lanes, Movie Theater, Eagles Nest (Eatery) and More. Make plans today to visit this home and Lake Ashton!

4028 Phoenician Way, Winter Haven

$375,000

4 Beds ⋅ 3 Baths ⋅ Estates/Lk Florence SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully maintained 2023-built home offering the perfect blend of modern design, functionality, and space to grow! Located in a desirable Winter Haven community, this move-in ready residence feels just like new construction without the wait. This spacious home features 4 bedrooms and 2.5 bathrooms, with all bedrooms thoughtfully located upstairs for added privacy and separation from the main living areas. The versatile floor plan is ideal for both everyday living and entertaining, offering a seamless flow throughout the home. The kitchen and living spaces showcase a clean, modern aesthetic, perfect for today’s lifestyle, while large windows bring in plenty of natural light. Whether you're starting a family or need more room to grow, this layout adapts to your needs with ease. Step outside to a huge fully fenced backyard with endless possibilities, create your dream outdoor oasis, add a pool, or design the perfect space for gatherings and play. Conveniently located just minutes from Legoland, shopping, dining, and major roadways, this home combines comfort, location, and value all in one. Don’t miss your opportunity to own a practically new home in one of Winter Haven’s growing areas!

1117 Michelangelo Lane, Winter Haven

$359,000

3 Beds ⋅ 2 Baths ⋅ Lake Dexter Moorings SubDv. ⋅ 33884 Zip Code

Virtually Staged. WATERFRONT LIVING ON BEAUTIFUL LAKE DEXTER-PRIVATE DOCK - OVERSIZED CORNER LOT -Newly Remodeled - This beautifully updated 3 Bedroom 2 Bath plus separate Dining Room/Office Lake Dexter canal home offers your own 15 X 25 private dock with electric and water, giving you easy access to boating, fishing and days on the lake. All right from your backyard. Inside, the spacious split-bedroom floor plan features an oversized living room with a fireplace and triple sliding doors opening to the screened lanai and spa. The kitchen had been remodeled with new quarts countertops, new abundant cabinetry, breakfast bar, additional counter space & beverage/wine cooler perfect for entertaining! The formal dining room can easily be converted into a large office/den with built-in oak bookshelves provides the perfect space for working from home or additional flex space. The newly renovated private primary suite offers dual walk-in closets, an updated bath and triple sliders providing direct access to the lanai, spa and outdoors! The guest bathroom has also been beautifully improved. Large inside laundry with plenty of pantry storage is great for organization. Outside, enjoy the huge lot partially fenced in from the waterfront dock! NEWER HVAC and DUCTWORK! NEW SPA PUMP & FILTER! The community also offers a boat ramp and community pool to enjoy when you come back in and want to cool off! If waterfront living, boating, fishing and plenty of space are on your wish list, this Lake Dexter home deserves a closer look! You will love living here!

1475 Grand Cayman Circle, Winter Haven

$329,999

4 Beds ⋅ 2 Baths ⋅ Inman Grvs Ph 2 SubDv. ⋅ 33881 Zip Code

Welcome to this beautiful 2023-built home in Winter Haven, offering 4 bedrooms, 2 bathrooms, approximately 1,867 square feet of living space, a two-car garage, and a fenced yard. Designed for comfortable modern living, this home features tile flooring throughout the main living areas and carpet in the bedrooms. The open-concept kitchen is perfect for everyday living and entertaining, featuring a large kitchen island, pantry, dining area, and all appliances included. Additional features include a whole-home water filtration system and solar panels that may be transferred to the buyer, subject to applicable terms and buyer qualification. Conveniently located near shopping, dining, medical facilities, and everyday essentials, with easy access to Cypress Creek Plaza, Polk State College, Winter Haven Hospital, and the Winter Haven station. Enjoy being close to LEGOLAND® Florida Resort and PEPPA PIG Theme Park, while Walt Disney World® Resort and the greater Orlando area are approximately 45 minutes away, depending on traffic and destination. This home is ready for its next owner. Schedule your private showing today!

751 Grove Street, Winter Haven

$309,900

3 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code

Welcome to 2 Casarena Ct, a truly unique opportunity in a private gated Winter Haven community. One of only three 3-bedroom with 3 full bathroom residences in the community, this spacious home is ideally positioned to capture beautiful views of Lake Cannon, part of Winter Haven’s renowned Chain of Lakes. Step inside to an inviting open-concept floor plan featuring an expansive living and dining area highlighted by a striking fireplace, creating a warm focal point for both everyday living and entertaining. The thoughtfully designed layout includes two generous primary suites, providing exceptional privacy and flexibility for owners, guests, extended family, or seasonal visitors. Each primary offers spacious living accommodations, with the balcony primary offering double vanity and a sauna in the shower, the while the additional ensuite bedroom and bath provide even more versatility. The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry, and convenient access to the main living and dining spaces. Enjoy Florida living from multiple outdoor areas, including a private balcony overlooking the community pool with views toward Lake Cannon, as well as a private Florida room at the rear of the home—perfect for morning coffee, reading, relaxing, or enjoying the Florida sunshine year-round. Additional features include two HVAC systems, with one replaced approximately six months ago, tankless water heater, natural gas connection, a whole-home generator for added peace of mind, and a two-car garage. A unique private paver parking space provides additional dedicated parking beyond the garage—an exceptional feature for condo living. Residents enjoy the benefits of a private gated community along with lawn care, access to the community pool, and lake access to Lake Cannon and the Chain of Lakes with boat slips that are first come first serve. The combination of water views, spacious living areas, multiple private suites, outdoor living spaces, garage parking, and community amenities makes this property an excellent option for buyers seeking the convenience of low-maintenance living without sacrificing space, privacy, or comfort. Whether you're looking for a full-time residence, seasonal Florida retreat, or spacious lock-and-leave lifestyle, 2 Casarena Ct offers a rare combination of privacy, lakefront community living, and exceptional interior space in the heart of Winter Haven.

2 Casarena Court, Winter Haven

$310,000

3 Beds ⋅ 2 Baths ⋅ Lake Elbert Estates SubDv. ⋅ 33881 Zip Code

Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home offering approximately 1,220 square feet of living space on a generous 0.28-acre lot. The home features an updated interior, modern finishes, comfortable living areas, and a functional floor plan. Conveniently located near shopping, dining, recreation, and downtown Winter Haven. Schedule your private showing today and come see everything this move-in-ready home. Owner is willing to give $5000 towards closing costs.

Winter Haven

$305,000

4 Beds ⋅ 2 Baths ⋅ St James Xing SubDv. ⋅ 33881 Zip Code

Virtually Staged. Weclome to this move-in ready single story home with a bright, open floor plan and inviting living spaces. The spacious kitchen features granite countertops, stainless steel appliances, and ample cabinet space. Functional vinyl flooring enhances the main living areas, while spacious bedrooms provide comfortable accommodations. An attached two car garage adds convenience to this lovely home. Easy to show!

4750 Osprey Way, Winter Haven

$319,900

4 Beds ⋅ 2 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code

SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

113 Avenue C Se, Winter Haven

$345,190

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in November 2026. This Castaway floorplan is available in farmhouse exterior designs. The inviting front porch opens to a gracious foyer with 2 adjacent secondary bedrooms and a full bathroom. The well-appointed island kitchen is open to the cafe area and spacious family room with access to the covered lanai. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. A 3rd secondary bedroom, full bathroom and conveniently located laundry room complete the Castaway plan.

823 Andrew Street, Winter Haven

$315,000

3 Beds ⋅ 2 Baths ⋅ Lake Deer SubDv. ⋅ 33880 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home, built in 2020 and located in the gated Lake Deer community. This move-in-ready residence features a bright, open-concept floor plan that seamlessly connects the living room, dining area, and kitchen—ideal for everyday living and entertaining. The kitchen is the heart of the home, offering granite countertops, stainless steel appliances, ample cabinetry, and a spacious center island with additional seating and workspace. Laminate flooring extends throughout the home, providing a clean, modern appearance with no carpet to maintain. The primary suite includes a private bathroom and walk-in closet, while two additional bedrooms are flexibility for guests, a home office, or a personal fitness space. The home also features an attached two-car garage and a covered rear patio overlooking the generously sized backyard—perfect for relaxing, entertaining, or creating your own outdoor retreat. Residents of Lake Deer enjoy access to a community playground and dock for fishing or taking in the peaceful lake views. Additional benefits include low HOA fees, no CDD, and Flood Zone X. Conveniently located near shopping, dining, schools, and major roadways. Schedule your private showing today!

195 Black Skimmer Lane, Winter Haven

$344,900

2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code

Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

4075 Bedford Avenue, Winter Haven

$340,000

4 Beds ⋅ 2 Baths ⋅ Reflections East Add SubDv. ⋅ 33884 Zip Code

** $10K PRICE REDUCTION as of 10/23/2026!!** More space, more flexibility, and more included! Located near LEGOLAND Florida Resort, this spacious Winter Haven home offers 2,257 square feet of total living area, including a permitted 320-square-foot addition completed in 2021. The interior features a bright main living area with vaulted ceilings, a separate dining space, generously sized bedrooms, an interior laundry room, and a well-equipped kitchen with ample cabinetry and counter space. The refrigerator, range, microwave, dishwasher, washer, and dryer are all included. Step outside to a fenced backyard designed for enjoying the Florida lifestyle. A brand-new permitted covered patio, completed in March 2026, provides an inviting shaded space for relaxing, grilling, or entertaining. The backyard also features mature shade trees and a paver gathering area with a built-in firepit and seating. Additional highlights include a complete HVAC system installed in 2023, a main house roof installed in 2017, a new patio roof installed in 2026, a two-car garage, an included security system, and eight included 360-degree security cameras. Conveniently positioned in Central Florida between Orlando and Tampa, the home provides access to major attractions, shopping, dining, recreation, and everything the Winter Haven area has to provide. With substantial living space, valuable permitted improvements, included appliances, and an outdoor area ready to enjoy, this home delivers features that are increasingly difficult to find at this price point. Schedule your private showing and see how much this property has to give.

817 Reflections Loop E, Winter Haven

$369,900

4 Beds ⋅ 3 Baths ⋅ Windridge SubDv. ⋅ 33881 Zip Code

Space, a Screened Pool and a location that keeps you connected! This 4-bedroom, 2.5-bath pool home on the north side of Winter Haven offers 2,836 sqft, a first-floor office/den, an upstairs bonus room and a 2-car garage. The HOA is only $350 a year, there's NO CDD, and it's in Flood Zone X. Out back, the screen enclosure covers both the 24x14 in-ground pool and the 38x11 covered lanai with ceiling fans, giving you a shaded spot to dine, relax or entertain any time of year. Past the pool, the backyard has room for pets, gardening or play. Inside, high ceilings and ceiling fans keep things bright and open. The kitchen opens to the family room and has granite counters, a cooking island, dual sinks and two pantries, with a separate dining room nearby. The 13x13 den works well as a home office, playroom or guest space. Upstairs, the bonus room sits at the center of the bedroom hallways and makes a great media room, hangout or second office. The 19x16 primary suite has two walk-in closets and an en suite bath with granite counters, a vanity area, a garden tub, a separate shower, a private toilet room and a linen closet. Three more bedrooms, including a roomy 16x13, share a second full bath with dual sinks. The washer, dryer, refrigerator, range, dishwasher and microwave all stay, and there's an inside laundry room. Furnishings are negotiable. Quick access to SR 27 puts Haines City, Davenport and I-4 within easy reach for commuting toward Orlando or Tampa.

5809 Windridge Drive, Winter Haven

$319,999

4 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully designed 4 bedroom, 2.5 bathroom two-story home, built in 2024, offering modern style, thoughtful upgrades, and easy maintenance living. Step inside to discover elegant tile flooring throughout the main level, creating a sleek and inviting atmosphere. The spacious kitchen features stunning quartz countertops, upgraded appliances, and beautiful gold accents that add a touch of sophistication to the heart of the home. Upstairs, you’ll find comfortable bedrooms with plush carpeting, including a spacious primary suite designed for relaxation. The open concept layout provides plenty of space for entertaining, everyday living, and making lasting memories. Step outside to enjoy the large paved backyard area, perfect for outdoor dining, entertaining, or creating your own private retreat. The backyard also features turf instead of traditional grass, providing a beautiful, low maintenance outdoor space without the hassle of regular mowing and upkeep. This move in ready home offers the perfect combination of comfort, style, and convenience.

231 Hayley Street, Winter Haven

$399,900

3 Beds ⋅ 3 Baths ⋅ Overlook Estates East SubDv. ⋅ 33884 Zip Code

Great new price on this Awesome 3 bedroom 3 bath home is ready for its you!!. Located in a GREAT gated community in off of Overlook Drive in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the kitchen with nice countertops and wood cabinets. The rooms have great windows offering abundant natural light, and space for everyone. The 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with no home in your back yard, Roof replaced in 2004.Check out this sweet property today. Step inside and you will love. Make it yours!!

742 Santa Maria Drive, Winter Haven

$345,000

3 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code

Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with a den, ideally situated in the premier gated active-adult community of Traditions at Lake Ruby. Designed with comfort, efficiency, and entertaining in mind, this beautifully appointed home offers an impressive array of upgrades and thoughtful features. The desirable split-bedroom floor plan provides privacy and versatility, including a spacious Junior Bedroom Suite with its own ensuite bath—perfect for visiting family or guests. The well-equipped kitchen is a chef’s delight, featuring a center island with pendant lighting, fingerprint-resistant stainless-steel appliance package, recessed lighting, and 42-inch white upper cabinetry enhanced with crown molding, soft-close hinges, and brush nickel hardware. A generous walk-in pantry provides additional storage, while the pull-out cabinet organizers keep everyday items conveniently within reach. The spacious Living Room features wood laminate flooring and triple glass sliding doors that open to the extended lanai, seamlessly blending indoor and outdoor living. The open-concept design also incorporates a dedicated Dining Room and cheerful breakfast nook, providing plenty of space for family gatherings and entertaining. The generously sized Primary Bedroom Suite is enhanced with laminate flooring and dual walk-in closets featuring deluxe closet organizer systems. The luxurious Primary Bath offers a handicapped-accessible tiled shower with glass enclosure, comfort-height vanity with dual sinks, and linen closet for additional storage. Outdoor entertaining is effortless in the oversized screened lanai, featuring decorative stamped-concrete flooring, retractable solar screens and a built-in buffet and BBQ Grill—perfect for enjoying Florida’s year-round outdoor lifestyle. Additional amenities include a versatile Den/Office, Laundry Room with cabinetry, washer and dryer, ceiling fans with remote controls, and extensive storage throughout. Energy-efficient features include solar panels with a monthly solar expense of approximately $209, a 15-SEER HVAC system, AO Smith hybrid water heater, Low-E windows, radiant heat barrier, and architectural shingle roof installed in 2026. A stone facade, decorative stone curbing, and paved driveway add to the home’s impressive curb appeal. Additional upgrades include smart-lock entry, whole-house generator, retractable garage screen, keyless garage entry pad, and a two-car garage equipped with three overhead storage racks, workbench with matching cabinetry, and an overhead solar skylight. Traditions at Lake Ruby offers an exceptional active-adult lifestyle with an impressive selection of amenities and planned community activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. Conveniently located near shopping, medical facilities, and major transportation routes, Traditions at Lake Ruby offers the perfect combination of resort-style amenities, energy-efficient living, and everyday convenience. HOME CAN BE PURCHASED FURNISHED

3541 Raleigh Drive, Winter Haven

$369,900

4 Beds ⋅ 3 Baths ⋅ College Estates SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. Virtually Staged. COMPLETELY RENOVATED 4-BEDROOM POOL HOME WITH NO HOA, OVERSIZED .42-ACRE LOT, DETACHED GARAGE/WORKSHOP AND A BRAND-NEW ROOF! Designed for entertaining inside and out, this move-in-ready 4-bedroom, 2.5-bath home offers 2,189 sq. ft. of heated living space and 2,818 total sq. ft. under roof, with no rear neighbors and an incredible backyard retreat. The transformation starts at the curb with a BRAND-NEW ROOF, fresh sod, updated landscaping and freshly painted exterior. Step inside to a bright, updated interior featuring luxury vinyl plank flooring throughout, fresh paint, abundant natural light, new lighting fixtures, updated hardware and new ceiling fans. At the heart of the home is a completely renovated kitchen featuring solid-surface countertops, brand-new cabinetry and stainless steel appliances. With plenty of workspace and an inviting layout, the kitchen flows naturally into the home's living areas, creating an ideal setting for everyday living and entertaining. The spacious primary suite features a beautifully renovated en-suite bathroom with dual sinks and a tiled walk-in shower. The guest bathroom has also been completely remodeled and includes a dual-sink vanity. Need even more space? A versatile bonus room with its own mini-split air-conditioning system, half bath and separate closet creates the perfect game room, home office, guest retreat, media room or additional living space. An air-conditioned breezeway leads to an oversized indoor laundry room offering even more storage and functionality. Now step outside to the feature that truly sets this home apart—YOUR OWN PRIVATE BACKYARD OASIS! The fully refurbished swimming pool features a refreshed finish, all-new pool equipment and new surrounding decking, creating a fantastic setting for Florida outdoor living. An attached covered outdoor pavilion provides the perfect shaded space for grilling, dining and entertaining, plus an additional storage room. The oversized, fully fenced .42-acre backyard offers plenty of room for pets, play and outdoor activities, while NO REAR NEIGHBORS adds to the sense of privacy. Double-gate access leads to a detached two-car garage/workshop, providing outstanding space for vehicles, hobbies, tools, equipment or additional storage. A BRAND-NEW SEPTIC TANK AND DRAINFIELD adds another significant recent improvement. With a NEW ROOF, RENOVATED KITCHEN AND BATHROOMS, REFURBISHED POOL, NO HOA, oversized fenced lot, detached garage/workshop, stainless steel appliances, luxury vinyl plank flooring, flexible home-office space and extensive updates throughout, this property checks the boxes today's buyers are searching for. Schedule your private showing and experience this move-in-ready Florida pool home for yourself!

822 17th Terrace Ne, Winter Haven

$329,090

4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3761 Giorgio Drive, Winter Haven

$335,000

4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3921 Giorgio Drive, Winter Haven

$349,900

4 Beds ⋅ 2 Baths ⋅ Ridge Acres Ph 02 SubDv. ⋅ 33880 Zip Code

Welcome to 456 Adriel Ave, where newer construction meets the space to actually spread out. Built in 2022, this thoughtfully designed 4-bedroom, 2-bath home offers approximately 1,874 square feet of living space on an impressive approximately half-acre homesite—a combination that can be hard to find among newer homes in Central Florida.Step inside to a bright, inviting floor plan designed for everyday living and easy entertaining. The kitchen serves as the heart of the home with dark cabinetry, light marble countertops, stainless steel appliances, generous prep space and a large peninsula that naturally connects the kitchen with the main living area. Just beyond, the living room adds personality with a distinctive tiled feature wall and fireplace, creating a comfortable gathering space with a modern touch.With four true bedrooms, the layout provides the flexibility today's buyers are looking for—whether that means additional bedrooms, a guest space, home office, hobby room or simply room to grow. The home's newer construction provides the clean, contemporary feel buyers want without the wait of building from scratch.But the story continues outside.The expansive fenced backyard offers the kind of room that changes how you live at home. There is space for pets, play, gardening, entertaining and creating your own outdoor retreat, along with an existing pergola/garden area that adds character to the setting. Whether you're enjoying a quiet Florida evening, hosting friends for a backyard cookout or simply appreciating the extra privacy and breathing room, this is outdoor space designed to be used—not just looked at.And then there is the location. Living in Winter Haven means enjoying a community known for its lakes and outdoor lifestyle, including the famed Chain of Lakes, along with boating, fishing and waterfront recreation. Downtown Winter Haven brings local restaurants, shops and community events together, while nearby shopping, dining and entertainment make everyday errands convenient. LEGOLAND Florida Resort and the area's many parks and recreational opportunities add even more to the Central Florida lifestyle.456 Adriel Ave isn't simply another newer home—it offers four bedrooms, modern living and the kind of homesite that gives you room to make the property your own. For added piece of mind, the fire station is only 5 minutes away. Newer home. Huge yard. Room to live.

456 Adriel Avenue, Winter Haven

$339,999

5 Beds ⋅ 4 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code

More than a home, this property offers the flexible space, storage, and energy-saving features today’s buyers are searching for! A standout bonus area provides incredible versatility with its own living space, closet, bathroom, and private rear entrance, making it ideal for multigenerational living, guests, a home office, or additional bonus rooms. Another bedroom features its own en suite bathroom for added comfort and privacy. Inside, enjoy granite countertops, upgraded lighting, ceiling fans throughout, and an abundance of closets and storage space. The dedicated laundry room includes cabinet storage, while a staircase in the garage provides convenient access to the attic for even more storage. Solar panels help keep monthly energy costs extremely low, even during Florida’s hottest months. Outside, the extended paver driveway offers additional parking and attractive curb appeal. The community features two swimming pools, a playground, and a walking trail. Enjoy a convenient Winter Haven location just minutes from Port 27 and the Chain of Lakes for easy lake access, as well as Downtown Winter Haven’s shopping, dining, and entertainment. The home is also approximately five minutes from Highway 27, providing easy travel to Orlando and surrounding areas, and is conveniently located near LEGOLAND Florida. This spacious and versatile home is ready for its next owner! This home is also available for rent! For rental details and lease information, please see MLS #L4965531.

6183 Grey Heron Drive, Winter Haven

$330,000

5 Beds ⋅ 4 Baths ⋅ Villamar Ph 4 SubDv. ⋅ 33884 Zip Code

Short Sale. ** $17K PRICE REDUCTION as of 10/20/2026!** Short Sale — Third Party Approval Required. Welcome to 2639 San Marco Way, a spacious 5-bedroom, 3.5-bathroom two-story home offering 2,701 square feet of flexible living space in Winter Haven, FL. This short sale opportunity presents an excellent chance to acquire a generously sized home at an improved price point in an established Winter Haven community. The two-story layout provides excellent separation of space, with room for large households, multigenerational living, home offices, or guest accommodations. Five bedrooms and three and a half bathrooms give the kind of flexibility that is increasingly difficult to find at this price point. Conveniently located near shopping, dining, medical facilities, and the beautiful Winter Haven Chain of Lakes, with easy access to US-27 and major routes to both Orlando and Tampa. This is a short sale subject to lender approval. Being sold as-is. Buyer and buyer's agent to verify all information including HOA fees, community details, restrictions, measurements, and permitted uses. A rare opportunity to own a large Winter Haven home — schedule your showing today!

2639 San Marco Way, Winter Haven

$309,900

3 Beds ⋅ 2 Baths ⋅ Carrolls Sub SubDv. ⋅ 33880 Zip Code

Virtually Staged. Under Construction. BRAND-NEW CONSTRUCTION –Welcome to this beautiful 3-bedroom, 2-bath home featuring 1,322 sq. ft. of living space with an open-concept floor plan. Thekitchen will feature shaker-style cabinetry, granite countertops, and stainless-steel appliances, with luxury vinyl plank flooring throughout the home. The exterior will be accented with stone veneer for added curb appeal. Additional features include an attached garage, covered front entry, and covered rear patio. Estimated completion in approximately 60–75 days. Secure this new construction home nand make it yours before completion! NO HOA, NO CDD! *Photos/renderings are for illustrative purposes only and may depict finishes, landscaping, furnishings, or features not included in the completed home.

2015 Recker Highway, Winter Haven

$359,900

3 Beds ⋅ 2 Baths ⋅ Terranova Ph 03 SubDv. ⋅ 33884 Zip Code

Welcome home to this stunning 3-bedroom, 2-bathroom residence tucked into the sought-after, gated community of Terranova. From the moment you step inside, an open floor plan invites you through sun-filled living spaces accented by elegant crown moulding and custom built-ins. The chef-inspired kitchen anchors the home with generous counter space and a breakfast bar — perfect for casual mornings or entertaining guests. Plantation shutters throughout add a touch of timeless charm while offering privacy and light control in every room. Step outside to a spacious backyard, a blank canvas ready for weekend barbecues, a play area, or the pool of your dreams. Beyond your front door, Terranova's gated setting offers peace of mind just minutes from shopping, dining, and medical facilities — the perfect blend of tranquility and convenience. Don't miss this one — call today to schedule your private showing!

464 Terranova Street, Winter Haven

$318,000

4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ph 5 SubDv. ⋅ 33881 Zip Code

A fantastic opportunity for investors or future homeowners! This beautiful corner-lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. It boasts a beautiful, spacious kitchen. The open-concept layout seamlessly connects the living and dining areas, creating the ideal space for entertaining guests or enjoying everyday family life. Sliding glass doors open onto a large backyard—perfect for outdoor activities, gatherings, or simply relaxing. Additional features include a two-car garage, a fully equipped laundry room, and a well-designed floor plan that prioritizes functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy excellent amenities such as a clubhouse, swimming pools, a playground, and walking paths. The home is close to shops, restaurants, and major roads—including easy access to US-27—making for a convenient commute to Winter Haven, Davenport, and Orlando attractions. Don't miss out on this incredible opportunity!

604 Sarner Pass Way, Winter Haven

$320,000

3 Beds ⋅ 2 Baths ⋅ Mariana Heights SubDv. ⋅ 33881 Zip Code

Discover the opportunity to own a home in a convenient Central Florida location, surrounded by attractions, recreation, shopping, dining, and everyday conveniences. Enjoy easy access to LEGOLAND® Florida Resort, approximately 25 minutes away, as well as LEGOLAND Water Park and PEPPA PIG Theme Park. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, water activities, and enjoying Florida's outdoors. The area provides convenient access to local parks, restaurants, shopping, entertainment, and downtown Winter Haven. Its Central Florida location also makes it an excellent base for enjoying many of the region's popular attractions while maintaining a more relaxed residential lifestyle. Whether you're looking for a primary residence, a second home, a vacation property, or an investment opportunity, this property offers the chance to enjoy the best of Winter Haven and Central Florida living. Schedule your private showing today!

4629 Palmetto Drive, Winter Haven

$339,000

4 Beds ⋅ 2 Baths ⋅ Inman Grvs Ph 1 SubDv. ⋅ 33881 Zip Code

Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased through November 2026 at $2,150 monthly. A fantastic opportunity for both investors and future homeowners.

507 Short Lane, Winter Haven

$319,990

4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. Ready in November, 2026. Beautiful Single Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The Baker plan is in Farmhouse exterior design. Adjacent the foyer you'll find 3 secondary bedrooms and a full bathroom. The well-appointed island kitchen overlooks the spacious family room and adjoining cafe with access to the covered lanai. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. Photos are representative only and not of the actual home. Selections, features, and finishes may vary.

815 Andrew Street, Winter Haven

$362,499

5 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code

Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5441 San Pietro Drive, Winter Haven

$359,000

4 Beds ⋅ 3 Baths ⋅ Overlook Estates East SubDv. ⋅ 33884 Zip Code

HOME SWEET HOME! This sweet 4 bedroom 3 bath home is ready for its next happy homeowner. Located in a small gated community in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the homey kitchen with granite countertops and wood cabinets. The corner pantry can hold all your treats for those football weekend get togethers. The rooms have large windows offering abundant natural light, and space for everyone. The ideal 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with a PVC-fenced back yard, and extra storage in a charming 10x12 planters shed. The 2025 architectural shingle roof, 2017 AC dual zone AC system, and Generac generator have you covered in all Florida weather. Check out this sweet property today. Step inside, fall in love. Make it yours!

754 Santa Maria Dr, Winter Haven

$349,500

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code

MOTIVATED SELLERS!!! Welcome to one of THE MOST DESIRABLE AND BEAUTIFUL 55+ GATED/GUARD community in Winter Haven, FL! LAKE ASHTON has great amenities for their residents to enjoy every day and feel in PARADISE. An enormous club house were events are held, two pools, dog park, golf course, bowling, movie theater, fitness center, restaurant, and more. There's also a 2nd clubhouse available for residents. This gorgeous well maintained home has MULTIPLE VALUABLE UPGRADES that the future owner would enjoy. Even the floor plan was updated in the KITCHEN making this home UNIQUE in the neighborhood! NEW ROOF was installed in 2024, DISHWASHER FEB 2026, REFRIGETATOR NOV 2025, and WATER HEATER 2021. Also ENJOY the BENEFIT of having WATER SOFTENER, A WATER PURIFIER SYSTEM IN THE KITCHEN and QUARTS COUNTER TOPS. For the outdoor living you have a SPACIOUS TILE FLOORING, SCREENED LANAI WITH FLORIDA GLASS FOR PRIVACY. ONE OF THE BEST FEATURES OF THIS PROPERTY IS THAT IT HAS PAID OFF SOLAR PANELS. WHAT ELSE YOU CAN ASK FOR? This helps with the electric bill cost. COME AND SEE THIS AMAZING HOME THAT WILL MAKE YOU FEEL IN PARADISE!

5325 Snead Drive, Winter Haven

$379,000

4 Beds ⋅ 2 Baths ⋅ West Winter Haven SubDv. ⋅ 33880 Zip Code

Step into a piece of Winter Haven history—beautifully reimagined for modern living. Just moments from Lake Howard, this exceptional 1925 residence offers the character and craftsmanship today's luxury buyers crave, paired with a complete top-to-bottom transformation. Original refinished 101 year old hardwood floors and two sets of original French doors provide a timeless connection to the home's past, while the rest has been thoughtfully rebuilt with today's lifestyle in mind. The custom kitchen, elegant architectural details, crown molding, tray ceilings, and spacious living areas create a home that feels both sophisticated and inviting. The private primary suite is a true retreat, featuring his-and-hers walk-in closets and a spa-inspired ensuite with a two-person tiled shower, garden tub, and generous vanity space. Two additional bedrooms upstairs add flexibility for guests, family, or a private home office. With approximately 2,011 heated square feet, 4 bedrooms, 2 baths, a dedicated laundry room, fully fenced backyard, and no HOA, this is a rare opportunity to own something with genuine character—not another cookie-cutter home. Bring your boat and water toys and enjoy the freedom and lifestyle that come with living near Winter Haven's beautiful Chain of Lakes. For buyers who appreciate history, character, and modern luxury, this is a home that simply must be experienced in person.

2112 Avenue C Sw, Winter Haven

$325,990

4 Beds ⋅ 2 Baths ⋅ Lake Smart Pointe SubDv. ⋅ 33881 Zip Code

Spacious 4-bedroom home in the beautiful and well-kept Lake Smart Pointe community, offering LOW HOA and NO CDD. This home features an open-concept layout with a kitchen island, Jack & Jill bath, and a private backyard with no rear neighbors and expansive green space behind the property. Nice neighborhood with convenient access to shopping, dining, schools, and major highways. More photos coming soon.

380 Lake Smart Circle, Winter Haven

$335,000

3 Beds ⋅ 2 Baths ⋅ Summerhaven Shores SubDv. ⋅ 33884 Zip Code

**NEWLY REDUCED PRICE** NO HOA- QUICK CLOSE AVAILABLE** IMMACULATE SE WINTER HAVEN, FLORIDA HOME LOCATED ON A SHADED CUL-DE-SAC LOT. NEW ARCHITECTURAL SHINGLE ROOF INSTALLED 2022, AC-HEAT PUMP SYSTEM NEW IN 2020 and NEWER INSULATED WINDOWS THROUGHOUT! The privacy-fenced rear yard has double-wide gates allowing access for storing your boat or RV plus plenty of space for the existing 10 x 16 storage/work shed with power, a large patio & separate fenced area for dog space or a garden! The living room & dining room area are conveniently located adjacent to the spacious, updated custom kitchen featuring granite countertops, stainless steel appliances, a 4-door refrigerator, 10 cabinet drawers, a pull-out trash drawer & center island. The family room features a beautiful brick fireplace with hearth and mantle, perfect for enjoying & decorating on holidays! Sliding glass exit doors allow access from the family room to the welcoming 18 x 37 covered and screened patio. The primary bedroom has a walk-in closet and includes a remodeled en-suite bathroom with a custom tiled walk-in shower and glass shower door. Bedrooms 2 and 3 are near the remodeled hall bath that features a comfort-height vanity & tub-shower combination. This lovely, well-maintained home is perfect for gatherings & entertaining! A public park with a boat ramp on Lake Ned is less than a mile away! Shopping and restaurants are nearby, plus be sure to check out the brand-new Publix grocery store located on Dundee Road! Easy access to Hwy 27 & I-4, Orlando, Tampa area attractions & both coasts. Measurements are approximate. Info is believed to be accurate but not guaranteed. This one will sell soon, so make your showing appointment today!

216 Shore Loop, Winter Haven

$390,000

4 Beds ⋅ 2 Baths ⋅ Carrolls Sub Pb 8 Pg 7 SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Discover this brand-new construction 4-bedroom, 2-bathroom single-family home, offering the perfect blend of modern style and functional living. The heart of the home is a contemporary kitchen featuring beautiful cabinetry, premium upgraded appliances, and clever design elements, including a hidden pantry and a dedicated coffee or liquor bar for effortless entertaining. The spacious living area provides an open, airy feel perfect for daily life or hosting guests. Retreat to the luxurious master suite, which acts as a private sanctuary with a spa-like bathroom. The master bath features a modern walk-in shower, a large soaking tub for ultimate relaxation, and generous his-and-her closets. Complete with a 1-car garage and located in the heart of Winter Haven, this home is move-in ready and designed for those who appreciate contemporary finishes and thoughtful, brand-new layouts.

2011 Recker Highway, Winter Haven

$385,000

3 Beds ⋅ 2 Baths ⋅ Terranova Ph 01 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. POOL HOME WITH POND VIEW IN GATED TERRANOVA! -NEW AC UNIT DECEMBER 2025--ROOF & HOT WATER HEATER ARE 6 YEARS OLD-- Welcome to this spacious 3-bedroom, 2-bath home offering 2,118 square feet of living space and a relaxing Florida lifestyle in one of southeast Winter Haven’s gated communities. The highlight of the home is the screened-in private pool overlooking the pond, creating a peaceful water-view backdrop for relaxing, entertaining, or enjoying time outdoors. Inside, the split-bedroom floor plan offers multiple living spaces, including a comfortable family room featuring a wood-burning fireplace. The eat-in kitchen provides plenty of space for casual dining and features a decorative backsplash behind the countertops, while the dining area flows naturally into the living room for an open and connected feel. Sliding doors provide access to the covered and screened pool area, where you can enjoy the pond views from your own backyard. The home also features a full bathroom with direct access to the pool area, adding extra convenience for family and guests. Additional features include an inside laundry room, walk-in closet, ceiling fans, attached 2-car garage, and a north-facing front exposure. Terranova is a gated community conveniently located in southeast Winter Haven with easy access to shopping, dining, schools, medical facilities, and area attractions including LEGOLAND Florida. Enjoy the combination of a private pool, water view, spacious interior, and gated-community setting—all in a convenient Winter Haven location. Schedule your private showing today!

543 Terranova Circle, Winter Haven

$340,000

5 Beds ⋅ 3 Baths ⋅ Pinnacle Point SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Short Sale. ** $10K PRICE REDUCTION as of 9/23/2026!!** This is a SHORT SALE-THIRD PARTY APPROVAL REQUIRED. Spacious and extensively upgraded, this 5-bedroom, 3-bath home offers more than 3,000 square feet of flexible living space in the Pinnacle Point community. The open floor plan features an impressive remodeled kitchen, upgraded flooring, generous living and gathering areas, and plenty of room for a large household, home offices, guests, or multigenerational living. Outside, enjoy a fenced backyard and improved patio area ready for relaxing, entertaining, or weekend cookouts. Built in 2022, the home also includes a two-car garage and convenient access to shopping, dining, medical facilities, and Central Florida attractions. Some interior projects remain unfinished, allowing the next owner to add their personal finishing touches.

1436 Axel Circle, Winter Haven

$305,490

5 Beds ⋅ 3 Baths ⋅ Villa Mar 40'S SubDv. ⋅ 33884 Zip Code

Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

6217 Botticella Boulevard, Winter Haven

$335,000

3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 33884 Zip Code

Back on market due to buyer not qualifying for loan - appraisal came in good! Welcome to this beautifully maintained 3-bedroom, 2-bathroom pool home offering comfort, functionality, and peace of mind with numerous recent improvements. From the moment you arrive, you’ll appreciate the inviting curb appeal, long driveway, and convenient side-entry garage. Step inside to a freshly painted interior and a warm, welcoming atmosphere featuring a wood-burning fireplace, perfect for cozy evenings at home. The spacious layout provides comfortable living areas and well-appointed bedrooms, making this home ideal for everyday living and entertaining. Step outside and discover your own private retreat! The resurfaced pool, completed in 2023, is surrounded by a large screened-in lanai, creating an expansive outdoor living space where you can relax, entertain, and enjoy the Florida lifestyle year-round. This home has been thoughtfully updated with numerous major improvements, including a 2023 roof and gutters, 2024 exterior paint, 2026 interior paint, and 2024 attic insulation. The HVAC system and water heater were replaced in 2021, along with the pool pump, providing added efficiency and peace of mind. Solar panels are already in place and will be paid off by the seller at closing, allowing the new homeowner to enjoy the benefits of solar without assuming the existing balance. Best of all, there is NO HOA, giving you greater freedom and flexibility. With a spacious lot, side-entry garage, long driveway, private pool, large screened lanai, and an impressive list of updates, this home is ready to welcome its next owner. Located in Winter Haven with convenient access to several lakes, local shopping, dining, recreation, major roadways and more. Come see all this move-in-ready pool home has to offer!

121 Lowell Road, Winter Haven

$379,000

4 Beds ⋅ 2 Baths ⋅ Eloise Woods East Lake Mariam Unit SubDv. ⋅ 33884 Zip Code

Welcome home to this CLEAN and PRISTINE 4-bedroom, 2-bathroom BLOCK pool home on a large lot with NO HOA! Inside, a great layout, light and bright walls and floors, and updated bathrooms, kitchen and flooring create a welcoming, modern feel. Sleek hurricane-impact windows and sliding doors add style, natural light, and peace of mind, while the roof and HVAC are both under 4 years old. Step outside and discover your own Florida oasis! The OVERSIZED POOL (36'x17') and huge 12' x 25' SCREENED-IN TILED PATIO create an incredible space for entertaining, relaxing, morning coffee, or enjoying beautiful Florida evenings. The spacious lot offers plenty of room to spread out, garden, and play! Solar panels add an energy-conscious bonus and meaningful energy savings. The location is difficult to beat! You are just 5 minutes from LEGOLAND, with sparkling lakes nearby for boating and fishing, golf courses, great restaurants, and plenty of Central Florida attractions within easy reach. Solid, stylish, spacious, and wonderfully located-this is a Florida home with room to live, relax, entertain, and make lasting memories. Come check it out TODAY!

437 Broward Terrace, Winter Haven

$374,500

4 Beds ⋅ 3 Baths ⋅ South Roy Shores Pb 38 Pg 45 SubDv. ⋅ 33884 Zip Code

Virtually Staged. UPDATED POOL HOME WITH NEW BATHROOMS, NEW POOL DECK & BRAND-NEW WATER HEATER! Welcome to this spacious 4-bedroom, 3-bathroom, 2,955-square-foot pool home on a desirable corner lot in Winter Haven, ideally located across from beautiful lakefront homes and close to Winter Haven's renowned Chain of Lakes. Major recent improvements include a BRAND-NEW HOT WATER HEATER installed in October 2026, TWO NEWLY REMODELED BATHROOMS completed in 2025, and a RESURFACED POOL WITH NEW POOL DECK completed in 2022. The roof was also replaced in 2023, providing additional peace of mind for the next owner. Inside, the triple-split bedroom floor plan offers privacy and flexibility, making this home ideal for families, guests, or those who need dedicated spaces for work and hobbies. The oversized family room is designed for entertaining, featuring two sets of sliding glass doors that open directly to the screened and netted pool enclosure and covered patio. The seamless indoor-outdoor flow creates the perfect setting for gatherings, relaxing poolside, or enjoying Florida's year-round lifestyle. A spacious flex room with direct pool and patio access offers endless possibilities as a game room, home office, media room, hobby space, or additional entertainment area. The kitchen features custom-made cabinetry, granite countertops, a custom tile backsplash, and stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The primary suite offers a private retreat with a bathroom featuring a garden tub, dual sinks, and a walk-in shower. The two recently remodeled bathrooms add fresh, updated appeal throughout the home. Additional highlights include a LARGE LAUNDRY ROOM with utility sink, drop-down ironing board, and extra shelving, as well as tile and wood flooring throughout the main living areas. Step outside to your own private backyard retreat. The resurfaced pool and NEW POOL DECK, completed in 2022, are surrounded by a screened and netted enclosure with a covered patio, creating an inviting space for swimming, dining, entertaining, and soaking up the Florida sunshine. A welcoming front screened porch, ample covered parking, and two detached storage sheds provide additional convenience and storage. The yard is irrigated by a well with a newer irrigation timer. The HVAC system is approximately 9 years old. While there are still opportunities for cosmetic updates in select areas, the home's generous size, desirable floor plan, significant recent improvements, and fantastic outdoor living spaces provide an excellent foundation for making it your own. Location adds even more appeal. The property is just a short walk to Freedom Boat Club, making it easy to access and explore Winter Haven's famous Chain of Lakes. LEGOLAND Florida is approximately one mile away, offering exceptional convenience for both residents and guests. With its four bedrooms, three bathrooms, private pool, newly remodeled bathrooms, resurfaced pool and new pool deck, new water heater, 2023 roof, flexible living spaces, and prime location near lakes and attractions, this is an exciting opportunity to own a spacious Winter Haven home and enjoy the best of the Florida lifestyle.

1380 S Lake Roy Drive, Winter Haven

$364,900

4 Beds ⋅ 3 Baths ⋅ Chestnut Crk SubDv. ⋅ 33881 Zip Code

PRICE REDUCED – MOVE-IN READY! Discover refined Florida living in the STUNNING SHENANDOAH II MODEL, an impressive SINGLE-STORY RESIDENCE offering 2,034 square feet of thoughtfully designed living space. Featuring 4 SPACIOUS BEDROOMS and 3 FULL BATHROOMS, this BEAUTIFULLY APPOINTED HOME blends ELEGANCE, COMFORT, and FUNCTIONALITY in a versatile layout designed for both everyday living and entertaining. From the moment you arrive, the CHARMING COLUMNED FRONT PORCH creates an inviting first impression. Step inside to a BRIGHT, OPEN-CONCEPT LIVING AREA where the seamless flow between the kitchen, dining, and living spaces creates an ideal setting for entertaining guests or enjoying relaxed evenings at home. The GORGEOUS KITCHEN is designed to impress, featuring PRISTINE SHAKER-STYLE CABINETRY, SAMSUNG STAINLESS STEEL APPLIANCES, a GENEROUS PANTRY, and a CHIC BREAKFAST BAR. The adjoining VERSATILE DINING AREA provides a welcoming space for everything from casual breakfasts to special gatherings. Throughout the main living areas and bathrooms, UPDATED 25-YEAR-LIFE-PROOF WOOD-VINYL FLOORING offers a SLEEK LOOK, while the bedrooms feature PLUSH STAIN-RESISTANT CARPETING for added comfort. These thoughtfully selected finishes combine BEAUTY, DURABILITY, and EVERYDAY PRACTICALITY. The SPACIOUS OWNER’S SUITE provides a peaceful retreat with a STYLISH TRAY CEILING, LARGE WALK-IN WARDROBE, and LUXURIOUS ENSUITE BATHROOM featuring DUAL SINKS and a BEAUTIFULLY TILED SHOWER accented by a GLASS ENCLOSURE. Step outside and embrace OUTDOOR LIVING on the EXPANSIVE COVERED LANAI, an inviting space for morning coffee, evening relaxation, or entertaining. Direct access to the THIRD FULL BATHROOM adds exceptional convenience for guests and outdoor activities. The LARGE BACKYARD provides a generous canvas for creating your own private outdoor retreat, with ample space to envision a future pool or customized outdoor living area, subject to applicable approvals and restrictions. Additional highlights include a 2-CAR GARAGE, ENERGY-EFFICIENT INSULATION, and ARCHITECTURAL SHINGLES, bringing together STYLE, EFFICIENCY, and PRACTICALITY. This EXCEPTIONAL HOME offers an appealing combination of BEAUTIFUL FINISHES, FUNCTIONAL DESIGN, SPACIOUS LIVING, and INDOOR-OUTDOOR COMFORT. If you’ve been waiting for a MOVE-IN READY RESIDENCE with room to personalize and make your own, this SHENANDOAH II MODEL deserves a closer look. WELCOME HOME!

1069 Sandpiper Loop, Winter Haven

$319,999

4 Beds ⋅ 2 Baths ⋅ Seasons At Annabelle Estates SubDv. ⋅ 33884 Zip Code

The single-story Ruby plan was designed for entertaining, offering a generous great room, an open dining area and a relaxing covered patio. You’ll also appreciate an impressive kitchen with a center island and a walk-in pantry, as well as a lavish primary suite with a private bath and an immense walk-in closet. This home will be built with either two secondary bedrooms and a study or three secondary bedrooms. A shared bath, a convenient laundry room and a 2-car garage complete this beautiful Seasons™ Collection home. Special financing rates and closing cost assistance may be available. Options may vary by community and offers are available on select homes only. Contact builder for more information!

5315 Mickey Avenue, Winter Haven

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