Winter Haven FL Historical Real Estate, Homes for Sale

4 Beds ⋅ 1 Baths ⋅ Chris Brown Cemetery Replat SubDv. ⋅ 33881 Zip Code

PRICE ADJUSTMENT***Don't Miss This Opportunity! This home offers amazing potential and features 4 bedrooms and 1 full bath, making it ideal for homeowners or investors. The kitchen is just off from the spacious dining area, great for family gatherings, while the spacious living room and family room provides extra space to relax. The primary bedroom as well as the other rooms are generously sized, offering a built-in closets. This home is a great candidate to be transformed into your ideal living space or added to your rental portfolio. Property is being sold As-Is. All buyers MUST view the home in person before submitting an offer. Opportunities like this don't last long, schedule your showing today before it's gone! ** FURNISHINGS, WASHER, DRYER, OR REFRIGERATOR DOES NOT CONVEY WITH THE SALE OF HOME.

111 Sunset Drive E, Winter Haven

$279,900

3 Beds ⋅ 2 Baths ⋅ Anna Mar SubDv. ⋅ 33881 Zip Code

**PRICE DROP** Check out this unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!

961 Drexel Avenue Ne, Winter Haven

$420,000

6 Beds ⋅ 5 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code

Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.

1339 7th Street Sw, Winter Haven

$257,999

4 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!

1701 36th Street Nw, Winter Haven

$214,999

2 Beds ⋅ 2 Baths ⋅ Coker A B Add SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. This 2 BR, 2 BA home is located near Rotary Park and Kiwanis Park, which is on Lake Martha, both public parks. Each park has room for games and family gatherings. Rotary Park has a baseball field with backstop and other outside activity areas. This home is located near schools, the Winter Haven downtown post office, the Winter Haven (Bay Care Hospital) and several doctors offices and medical clinics. The Winter Haven Public Library is also 6+/- blocks to the west of this property. The home has a metal roof which offers a long life and better storm protection than typical asphalt shingles. The windows have been replaced and the central A/C - Heat system has recently been inspected. The home has attic storage, however, a detached storage building, with a high interior ceiling, provides room for lawn equipment or other large items not needed inside the residence. where they are more easily accessed than typical attic space provides. The interior of the home has been extensively renovated with both bathrooms completely remodeled.

414 Avenue C Avenue Ne, Winter Haven

$109,900

2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

1700 6th Street Nw Unit C1, Winter Haven

$250,000

2 Beds ⋅ 2 Baths ⋅ Cooper Estates SubDv. ⋅ 33880 Zip Code

Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

940 Oleander Drive Se, Winter Haven

$550,000

9 Beds ⋅ 6 Baths ⋅ Coker A B Add SubDv. ⋅ 33881 Zip Code

Virtually Staged. Rare opportunity to own a 5-unit multifamily investment property situated on an oversized lot in the rapidly growing and expanding City of Winter Haven. The property consists of three separate buildings, providing flexibility, privacy, and multiple income streams. Currently, three units are leased with one vacant unit available for immediate occupancy or additional rental income potential , air b n b options as well . Recent renovations and updates completed within the past year include a new metal roof, updated HVAC systems, and numerous interior and exterior improvements, helping minimize deferred maintenance and enhance long-term value. Located near shopping, restaurants, schools, medical facilities, and major roadways, this property is positioned in one of Central Florida's strongest and fastest-growing rental markets. The versatile layout presents numerous possibilities for investors seeking cash flow, portfolio expansion, house-hacking opportunities, or potential short-term rental and Airbnb use, subject to local regulations and buyer verification. With strong income potential, multiple buildings, recent capital improvements, and a prime Winter Haven location near attractions, employment centers, and everyday conveniences, this is a unique opportunity to acquire a well-maintained multifamily asset with both immediate income and future upside.

514 Avenue C Ne, Winter Haven

$105,000

2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

55+ COMMUNITY IN WINTER HAVEN! CORNER UNIT WITH GREAT AMENITIES! Looking for easy, low-maintenance living in a 55+ community in Winter Haven? This spacious corner-unit condo offers comfort, convenience, and plenty of amenities. Inside, you’ll find a kitchen with granite countertops and marble flooring, plus wood laminate floors throughout the living room, dining area, and hallway. The convenient interior laundry area includes a washer and dryer, making everyday living a little easier. The primary bedroom opens to a screened-in balcony, creating a nice spot to enjoy your morning coffee or relax at the end of the day. The community offers plenty to keep you active and connected, including a large heated swimming pool, pickleball courts, shuffleboard, grilling area, and clubhouse with a fitness center. Additional features include elevator access, reserved covered parking, secure storage, and a common laundry area. Located in central Winter Haven, you’ll be close to downtown, shopping, restaurants, hospitals, and medical facilities. With convenient access to I-4, you’re also within easy reach of both Orlando and Tampa. If you’re looking for a 55+ condo in Winter Haven with resort-style amenities and a convenient location, this corner unit is worth a look!

1700 6th Street Nw Unit B24, Winter Haven

$325,000

5 Beds ⋅ 3 Baths ⋅ Lakewood SubDv. ⋅ 33884 Zip Code

Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it into one of the best investments on the street. Surrounded by beautiful homes with strong property values, this two-level home boasts 5 bedrooms (with potential for a 6th), three bathrooms, and 2579 square feet of living space. Inside, you'll find real hardwood floors, double-paned windows, a cozy wood-burning fireplace, and a double car garage, all situated on a spacious 0.32-acre lot. With a little TLC and creativity, this property has the potential to become a stunning showcase home that stands out in the neighborhood. Don't miss this opportunity to own a piece of Winter Haven's red brick charm and create the home of your dreams. Schedule a showing today and start envisioning the possibilities that await.

129 Lake Otis Road Se, Winter Haven

$298,000

3 Beds ⋅ 2 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code

Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

1301 Evalyn Drive Se, Winter Haven

$265,000

3 Beds ⋅ 1 Baths ⋅ Biltmore Shores SubDv. ⋅ 33881 Zip Code

This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

3022 Hickory Street Nw, Winter Haven

$260,000

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

Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!

29 Golf View Circle Ne, Winter Haven

$249,000

Ida Lake Sub SubDv. ⋅ 33881 Zip Code

THIS PROPERTY HAS AN LCC LAND USE WITH THE COUNTY OF WINTER HAVEN. MANY POSSIBILITIES INCLUDING LIGHT INDUSTRIAL AND/OR MIXED USE RESIDENTIAL. WOULD BE GREAT FOR BUSINESS/RESIDENTIAL OR LIGHT INDUSTRIAL USE

2844 Lake Alfred Road, Winter Haven

$450,000

Bryson R H Sub SubDv. ⋅ 33880 Zip Code

If you’ve been looking for a clean, standalone commercial building in a prime, high-visibility location, this is it. Located on 1st Street South, surrounded by busy auto dealerships and professional offices, and just minutes from downtown Winter Haven, this freestanding building offers excellent exposure with steady drive-by traffic throughout the day. The property features ample paved parking, including front and side spaces, and sits on a corner with easy access and visibility from multiple directions. Inside, you’ll find a bright, open layout with flexible rooms that can be adapted for many types of businesses — salon, boutique, medical office, professional services, or even a small café or studio. The building features a welcoming front entry, updated lighting, two restrooms, and central air conditioning units. Winter Haven continues to grow rapidly, attracting both residents and investors due to its central location in Polk County and proximity to Lakeland, Orlando, and Tampa. This property gives you a chance to own a piece of that growth in one of the most active corridors in town. Highlights: freestanding commercial building with great curb appeal, Plenty of on-site parking.High-traffic corridor near car dealerships and retail centers. Ideal for office, salon, or professional use Easy access to U.S. 17 and Cypress Gardens Blvd.

1610 1st Street S, Winter Haven

$256,500

2 Beds ⋅ 1 Baths ⋅ Tranquility Park 02 Rep SubDv. ⋅ 33880 Zip Code

Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

1601 Roselawn Street Sw, Winter Haven

$249,900

4 Beds ⋅ 2 Baths ⋅ Dugger Rep SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Short Sale. ***THIS IS AN UNAPPROVED SHORT SALE TRANSACTION*** Spacious 4/2 with a duplex layout. an impressive 12,000sqft+ lot that includes a covered back patio, nice sized pool, and detached garaged. Property needs new roof, pool work, and a variety of other repairs throughout the property. Tenant occupied. 24hr notice needed

116 Hampden Road, Winter Haven

$330,000

3 Beds ⋅ 2 Baths ⋅ Almeda Park SubDv. ⋅ 33880 Zip Code

Welcome to 991 S SE in Winter Haven. This beautifully upgraded, turnkey home is being offered fully furnished and sits quietly at the end of a peaceful street with no HOA. It perfectly blends mid-century modern charm with stylish, modern updates throughout. Inside, you’ll find three bedrooms and two full bathrooms, along with two spacious living areas that can easily serve as a home office, playroom, or additional lounge space. The open floor plan feels bright and inviting, with plenty of natural light, walk-in closets, and a centrally located guest bath. The owner has already completed all the major updates for you, including a newer roof, newer water heater, and a brand-new septic system, ready for you to just move in and enjoy. Outside, the home features a sparkling courtyard pool, a storage shed, and a convenient circular driveway that provides plenty of parking. This property is perfect as a primary residence, seasonal getaway, or fully furnished short-term rental with excellent Airbnb potential. Located near shopping, dining, and Central Florida attractions, this home offers a wonderful combination of comfort, privacy, and convenience.

919 Avenue S Se, Winter Haven

$1,550,000

Taprell Terrace Sub SubDv. ⋅ 33881 Zip Code

Exceptional Commercial Property with High Traffic Exposure – Auto Repair Business Included. Unlock the potential of this expansive 8,056 sq. ft. commercial property, currently operated as a successful auto repair shop. Situated on a prime corner lot at a busy intersection with over 30,000 vehicles passing daily, this property offers unbeatable visibility and accessibility—ideal for a wide range of business ventures. The building features multiple rooms and flexible spaces that can be easily adapted or leased for various uses, such as retail, office, or service-based businesses. Whether you're looking to expand an existing operation, launch a new enterprise, or invest in a high-traffic commercial location, this property delivers endless possibilities. Included in the sale are the land, the building, and the existing auto repair business, offering a turn-key investment opportunity with established income potential. This property is not only a functional business. It is a long-term asset in a thriving commercial corridor. Whether you continue the auto business or reposition the space, the location and layout present endless opportunities for growth and income. Schedule a private tour today and explore the full potential of this exceptional property.

2010 8th Street Nw, Winter Haven

$289,000

3 Beds ⋅ 2 Baths ⋅ Cooper Estates SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. BACK ON MARKET - NEWLY REWIRED & FRESHLY PAINTED INTERIOR! Welcome to this inviting 3 bedroom, 2 bath home in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious Florida Room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a decorative fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!

880 Oleander Drive Se, Winter Haven

$189,900

3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Cute as a button. Great starter home or investment property. Large corner lot. Featuring NEW ROOF, NEW SEPTIC, NEW ELECTRICAL PANELS. This three bedrooms one & one half bathroom has a new modern eat in kitchen and laminate floors. Open spacious living and dining room. Covered front porch. Why rent just buy. Adjoining vacant lot is not included in the sale and has been removed from the legal description. Lot maybe purchased separately. Seller will contribute towards buyers closing costs. Please see realtor remarks.

1997 26th Street Nw, Winter Haven

$195,000

3 Beds ⋅ 2 Baths ⋅ South College SubDv. ⋅ 33880 Zip Code

Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an updated kitchen with ample cabinet space, and a comfortable primary suite designed for everyday living. Outside, the generous fenced-in lot provides room for entertaining, expansion, or future development. What truly sets this property apart is its strategic location, making it a strong candidate for Commercial or Industrial rezoning. Whether you envision office space, a retail storefront, business headquarters, long-term rental, or continued residential use, the possibilities are wide open. Perfectly suited for homeowners, investors, or entrepreneurs, this Winter Haven property combines location, accessibility, and potential. Don’t miss this rare opportunity, schedule your private showing today!

1109 5th Street Sw, Winter Haven

$430,000

5 Beds ⋅ 5 Baths ⋅ Lake Add SubDv. ⋅ 33880 Zip Code

Great investment opportunity! Tenant-occupied property in a central location with strong rental demand. Short sale subject to lender approval. Sold as-is, no repairs. Do not disturb tenants. No seller/creative financing.

724 W Central Avenue, Winter Haven

$479,000

5 Beds ⋅ 3 Baths ⋅ Southeast Terrace SubDv. ⋅ 33880 Zip Code

Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.

1818 6th Street Se, Winter Haven

$750,000

Mariana Heights SubDv. ⋅ 33881 Zip Code

Don't miss out on this opportunity for a ready to go pool business with direct exposure to US 92. This pool business features a large lot with over 150 ft road frontage on us 92. The office/showroom features air-conditioned office space as well as plenty of covered storage space behind the office.

2999 Us Highway 92, Winter Haven

$199,900

2 Beds ⋅ 1 Baths ⋅ Eula Vista Sub SubDv. ⋅ 33881 Zip Code

EXCELLENT INVESTMENT OPPORTUNITY IN THE HEART OF WINTER HAVEN! LOCATED AT 601 AVE U NE, THIS PROPERTY OFFERS INCREDIBLE POTENTIAL FOR RENTAL INCOME OR FUTURE DEVELOPMENT. WITH A SPACIOUS LOT AND SOLID STRUCTURE, IT'S PERFECT FOR INVESTORS LOOKING TO RENOVATE, RENT, OR FLIP. CONVENIENTLY SITUATED NEAR DOWNTOWN WINTER HAVEN, SCHOOLS, SHOPPING, AND MEDICAL FACILITIES, THIS LOCATION IS IDEAL FOR LONG-TERM TENANTS OR RESALE VALUE. BENEATH THE EXISTING CARPETING, YOU WILL FIND WELL-PRESERVED HARDWOOD FLOORING READY TO BE DISCOVERED AND ENJOYED. DO NOT MISS YOUR CHANCE TO OWN A PIECE OF RAPIDLY GROWING WINTER HAVEN-OPPORTUNITIES LIKE THIS DO NOT LAST LONG!

601 Avenue U Ne, Winter Haven

$750,000

4 Beds ⋅ 4 Baths ⋅ Orchid Springs Unrecorded SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. MAJOR PRICE IMPROVEMENT! Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

200 Island Way, Winter Haven

$240,000

4 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Short Sale. Requires a some TLC & Refresh. Pool Home.

119 Allen Avenue, Winter Haven

$899,000

3 Beds ⋅ 3 Baths ⋅ Mirro Mac SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. Virtually Staged. Mid-century modern lakefront pool home on the beautiful Winter Haven Chain of Lakes! Welcome to The Guest House, a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.

1540 N Lake Mirror Drive Nw, Winter Haven

$399,000

Lake Add SubDv. ⋅ 33880 Zip Code

TWO Redesigned and remodeled office buildings by local architect. Front building is known as 737 W Central Avenue, the rear building is known as 739 W Central Avenue. These buildings are located close to downtown, shopping, and retail centers.

737 W Central Avenue, Winter Haven

$204,999

3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Welcome to 1101 28th St NW, Winter Haven, FL 33881 – a fully remodeled and income-generating property perfect for first-time buyers, investors, or anyone needing a private space for in-laws or extended family! Public records show the home as a 2-bedroom, 1-bathroom, but it now features including a completely separate 1-bedroom, 1-bath apartment currently rented for extra income. The entire property has been tastefully updated—move-in ready with modern finishes throughout. Whether you're looking to offset your mortgage, expand your rental portfolio, or bring your parents closer while maintaining privacy, this home checks all the boxes. Don’t miss this unique opportunity

1101 28th Street Nw, Winter Haven

$99,900

2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code

Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

700 Mirror Terrace Nw Unit 303, Winter Haven

$116,000

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, making maintenance a breeze. The kitchen features new appliances and solid surface countertops, while the updated bathroom adds a modern touch. Assigned covered parking is included with the unit. The active 55+ community boasts a newly remodeled, heated pool, clubhouse, shuffleboard courts, and a grilling area perfect for entertaining. A convenient car wash station is also available on-site. Public transportation stops right outside the community, and you're just a short distance to shopping and dining options. Medical facilities and a hospital are just blocks away. Centrally located between Tampa and Orlando, this location is ideal for both convenience and connectivity. OWNER WILL CONSIDER FINANCING. Please note: Buyer approval is required. All units are owner-occupied—rentals are not permitted.

1700 6th Street Nw Unit C26, Winter Haven

$124,000

2 Beds ⋅ 2 Baths ⋅ Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B SubDv. ⋅ 33880 Zip Code

Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms. Don't miss out- schedule a showing today!

689 Lake Howard Drive Nw Unit 1E, Winter Haven

$269,000

Florence Citrus Growers Assn Sub SubDv. ⋅ 33881 Zip Code

Prime commercial opportunity in a high-visibility location with strong owner-user and investment potential. Freestanding commercial building Just price reduced for you to start your own business. Prime corner lot with a well-established stand alone operating business for over 20 years. This commercial property offers incredible potential and could be converted for other uses with county approval. The roof is only 4 years old, and the AC unit is about 1.5 years old. It has 8 hair stylist chairs, 3 shampoo chairs, 10 waiting chairs and 9 dryers all included in the price. While the property needs some TLC, it’s priced accordingly—making it a fantastic investment. Don’t miss this chance to be your own landlord/boss! Call today for more details. Some photos are staged.

2106 1st Street N, Winter Haven

$245,000

3 Beds ⋅ 2 Baths ⋅ Lake Elbert Heights Unit 02 02 Rep SubDv. ⋅ 33881 Zip Code

Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

1540 Avenue C Ne, Winter Haven

$185,000

3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

SELLER MOTIVATED Beautiful FULLY RENOVATED single-family home. These 3 BEDS, 2 BATHROOMS home features BRAND NEW kitchen, Roof, bathrooms, flooring, paint, lighting and more. This gem provides a welcoming environment, located on a lot with surrounding greenery. Whether you're on the lookout for Starter home or an investment home, this property is a great option. What's nearby? This home is located in an area with plenty of options for recreational activity, restaurants, shopping, and more. Within a 10-minute radius, there is much to experience from the surround no lakes in the arca, includina Lake Cannon, to the movie theater al CMX Grand 10 Cinemas, and the Auburndale Speedway.

3931 Avenue R Nw, Winter Haven

$145,066

3 Beds ⋅ 2 Baths ⋅ Wahneta Farms SubDv. ⋅ 33880 Zip Code

2 Lots and 2 Homes for the price of One. Attention investors and those looking for a great deal! Seize a truly unique opportunity to own two homes for the price of one. This property includes a single-family home with 2 bedrooms and 1 bathroom address 215 10th Wahneta St W Winter Haven FL, as well as a single-wide mobile home from 1988 with 2 bedrooms and 1 bathroom address 213 10th Wahneta St W Winter Haven FL 33880. The single-family & Mobile home needs Lot's TLC but has great potential. It could be perfect for someone willing to put in some work or an investor looking to flip or rent it out. Also included on the property is a detached garage offering an extra 480 square feet of storage space. This unique setup offers flexibility depending on your needs. This is truly a rare find at this price point. Don't miss out on this fantastic investment opportunity! Dual Rental Income, Fix-and-Flip Potential, Multi-Generational Living

215 10th Wahneta Street W, Winter Haven

$457,465

Daniels Sub SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. AGGRESSIVELY PRICED PORTFOLIO SALE—MUST BE SOLD TOGETHER WITH 524 1ST ST S, WINTER HAVEN, FL 33880. This 2,300± SF commercial building is part of a two-property offering with a combined price of $720,000. The adjacent property at 524 1st St S includes an additional 1,320± SF office/medical-style building. The properties will not be sold separately. Located in a visible Winter Haven commercial corridor, this building offers a flexible retail/flex-style layout with open work or display areas, storage, two restrooms, ramped access, central air conditioning, and on-site parking. Zoned C-3, the property may support a variety of retail, office, professional, wellness, service, and specialty commercial uses, subject to buyer verification and municipal approval. The health food store business may be available through a separate transaction. Inventory, refrigeration, shelving, racking, and trade fixtures are not included in the real estate sale unless separately negotiated. Buyer must independently verify square footage, zoning, permitted uses, condition, accessibility, and all other property information.

632 1st Street S, Winter Haven

$262,535

Van Sickle C H Sub SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. AGGRESSIVELY PRICED PORTFOLIO SALE—MUST BE SOLD TOGETHER WITH 632 1ST ST S, WINTER HAVEN, FL 33880. This 1,320± SF office/medical-style commercial building is part of a two-property offering with a combined price of $720,000. The adjacent property at 632 1st St S includes an additional 2,300± SF retail/flex building. The properties will not be sold separately. This building features a reception/waiting area, office areas, support space, ramped entry, central air conditioning, and on-site parking. Zoned C-3, the property may support a variety of office, medical-related, wellness, professional, service, retail, and specialty commercial uses, subject to buyer verification and municipal approval. The adjoining 632 1st St S property is currently associated with a health food store business, which may be available through a separate transaction. Inventory, refrigeration, shelving, racking, and trade fixtures are not included in the real estate sale unless separately negotiated. Buyer must independently verify square footage, zoning, permitted uses, condition, accessibility, and all other property information.

524 1st Street S, Winter Haven

$1,479,999

Kennedy Heights SubDv. ⋅ 33880 Zip Code

Have you been looking for opportunity to get into the ever growing Food and Beverage business in central Florida? Look no Further... DUKES Sports Bar Winter Haven may just be your answer. Located Just off Cypress Gardens Blvd. and 6th Street SE. Well marked and visible from all directions, compliments of the extra Large Illuminated Signage out front. Surrounded by Shopping Centers like Walmart, TJMAXX and Publix as well as many Chain Restaurants, Chili's , Olive Garden, Red Lobster, Outback just to name a few. Winter Haven is among the fastest growing cities in Polk County, which is one of the fastest growing counties in the State of Florida. Home to the world renown Legoland just a few miles down the street. Building and Business along with all equipment is included. List of inventory is available upon request. Call for private showing after business hours.

1708 6th Street Se, Winter Haven

$1,590,000

33880 Zip Code

High visibility business location with a property use code of Auto Repair/ Commercial Service Garage (2750). Currently owner occupied and partially leased retail. Still retains architecture of Mid-Century Modern as built. Established highest visibility business location since 1958. Clean environmental report. Corner location on the major State Road east-west corridor 540.

801 Cypress Gardens Boulevard, Winter Haven

$700,000

2 Beds ⋅ 1 Baths ⋅ 33884 Zip Code

The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.

103 Eagle Lake Loop Road, Winter Haven

$1,150,000

6 Beds ⋅ 6 Baths ⋅ Lesnick Park SubDv. ⋅ 33880 Zip Code

THIS PROPERTY WAS ORIGINALLY 2 HOMES THAT WERE CO-JOINED. THE CURRENT OWNER HAS RECREATED TWO FULLY SEPARATE LIVING SPACES. OWNER LIVES IN ONE SIDE AND HAS A VERY SUCCESSFUL AIRBNB ON THE OTHER SIDE. THIS IS A UNIQUE OPPORTUNITY FOR A LARGE FAMILY, EXTENDED FAMILY WITH IN-LAWS, OR THOSE LOOKING FOR A STEADY STREAM OF SUPPLEMENTAL INCOME. BEAUTIFUL LAKEFRONT POOL HOME WITH EXPANSIVE VIEWS. EACH ROOM IS DETAILED WITH CROWN MOULDING THROUGHOUT. GORGEOUS WOOD FLOORS. LARGE BEDROOMS AND OPEN LIVING SPACES ABOUND.

1200 W Lake Otis Drive Se, Winter Haven

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