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$197,500
3 Beds ⋅ 2 Baths ⋅ Hartridge Manor SubDv. ⋅ 33881 Zip Code
Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking and gathering. Spacious bedrooms showcase relaxing retreats for rest and privacy. The home sits on a generous lot with room to enjoy outdoor living. The backyard is perfect for relaxing evenings, gardening, or weekend gatherings. With no HOA, you’ll enjoy added flexibility and freedom. Ample parking adds convenience for residents and guests alike. The location provides easy access to shopping, dining, and daily essentials. Nearby parks and lakes fit outdoor recreation opportunities year-round. Major roadways are just a short drive away for easy commuting. This property is a great fit for homeowners or investors seeking value and potential. Come explore the possibilities this home has to show for.

820 Avenue Z Nw, Winter Haven
$379,998
4 Beds ⋅ 3 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter Haven Rare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place. Landlord expenses are minimal: owner covers water (~$25/mo) and basic WiFi ($50/mo). Tenants handle electricity, lawn maintenance, and all other utilities — maximizing net cash flow from day one. 4 bedrooms | 2 bathrooms | 1,680 sq ft | Built 1965 | Polk County | Minutes from US-27, downtown Winter Haven, and Legoland Florida. Ideal for the buy-and-hold investor seeking immediate cash flow with low management overhead. Current leases transfer at closing. All financing welcome: Conventional | DSCR Loan | Cash.

215 Kilmer Lane, Winter Haven
$2,400,000
33884 Zip Code
Presenting a rare investment and owner-user opportunity along one of Central Florida’s most prominent commercial corridors. This fully renovated restaurant property offers approximately 2,200 square feet of thoughtfully updated space situated on nearly one acre with extensive on-site parking and exceptional visibility. Recent capital improvements include a new roof, new HVAC system, and comprehensive interior and exterior renovations, creating a true turnkey asset ready for immediate operation. Strategically positioned on highly traveled Cypress Gardens Boulevard, the property benefits from strong daily traffic counts, excellent accessibility, and proximity to major retail, entertainment destinations, residential communities, and tourism-driven demand. The generous site size provides flexibility for future expansion, redevelopment opportunities, outdoor dining enhancements, or additional revenue-generating uses, subject to local approvals. Whether acquired as a flagship restaurant location, long-term investment, or redevelopment play, this offering combines a premier location, significant recent upgrades, strong market fundamentals, and exceptional visibility in one of Winter Haven’s most desirable commercial corridors. Opportunities of this caliber and location are increasingly rare in today’s market.

7350 Cypress Gardens Boulevard, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Buckeye Heights SubDv. ⋅ 33881 Zip Code
SELLER MOTIVATED!!! Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously sized layout including three spacious bedrooms and two bathrooms. The primary suite is a true retreat, complete with a walk-in closet for ample storage. At the heart of the home, a large kitchen and dining area provides the perfect setup for family gatherings and entertaining. Step outside onto the oversized 0.26-acre lot, where the backyard offers a private oasis featuring mature, producing fruit trees, a handy detached storage shed, and a solid privacy fence running across the rear property line. Perfectly situated in a desirable community zoned for great local schools, this property has incredible bones and just needs some updating and TLC to truly shine. The seller is highly motivated and ready to see your offers—bring your design ideas and schedule your private showing today to unlock this home's immense potential!

1406 Meadow Drive Ne, Winter Haven
$255,000
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
No HOA, no CDD! Jump in to get a deal! Charming brick home nestled only few min from Downtown Winter Heaven and near Legoland. Luxury upgraded and boast lots of improvements - brand new roof, new luxury vinyl planks floor throughout, new interior and exterior paint, new bathroom and new shower room, new pluming, brand new kitchen cabinets and granite counters, new Stainless Steel appliances, new lights throughout, all new doors and door frames. Brand new landscaping and fence in back yard. Schedule private showing today - close it tomorrow and enjoy your dream home with your family! This is only for you!!!

603 Maggie Circle, Winter Haven
$1,195,000
5 Beds ⋅ 6 Baths ⋅ Na SubDv. ⋅ 33881 Zip Code
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

250 Brigham Road Nw, Winter Haven
$550,000
4 Beds ⋅ 1 Baths ⋅ West Winter Haven SubDv. ⋅ 33880 Zip Code
Stunning 2 story 3 bath Spanish home with attention to details. This home has been renovated, roof was complete in 2019, painted inside and out in 2020, new A/C in 2023, electric and plumbing and the sprinkler system in 2023. Upon entering into the family room, you will immediately notice the vaulted beam ceilng along with the 20foot high fireplace. There are built-ins and bookcases throughout the home. Walking up into the kitchen, there is granite throughout and stainless steel appliances, along with a breakfast nook. There is a beautiful flooring throughout the home. On the first floor, there is another sitting room,along with a bedroom and a additional renovated full bath. On the second floor, it provides the laundry room and two more bedrooms and two full bathrooms that have been tastefully renovated. Going outside, there is convered area where you can relax and the property is completely fenced in. Another great feature is a detached studio that has been

409 21st Street Sw, Winter Haven
$164,900
2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
Virtually Staged. Charming single-story home located in Winter Haven with a functional layout and comfortable living spaces throughout. This 3-bedroom, 1-bath property features an inviting living area filled with natural light, a spacious kitchen with ample cabinet and counter space, and tile flooring throughout for easy maintenance. The home also offers a covered parking area, paved driveway, and a generously sized yard with room to enjoy outdoor living. Conveniently located near shopping, dining, parks, lakes, and major roadways for an easy commute throughout Polk County.

3214 Avenue Q Nw, Winter Haven
$2,150,000
33881 Zip Code
Build your legacy on this rare 10+ acre high-and-dry estate parcel in the heart of Winter Haven. Mostly cleared and ready for your vision, this exceptional property offers the perfect blend of privacy, prestige, and convenience. Whether you're dreaming of a custom luxury mansion, an equestrian retreat, or a multi-generational family compound, the possibilities here are endless. Tucked away in a peaceful setting yet just moments from Country Club of Winter Haven, you'll enjoy the serenity of expansive acreage without sacrificing access to golf, dining, shopping, and top local amenities. Mature natural surroundings provide a secluded atmosphere with ample space for guest homes, workshops, barns, recreational toys, or resort-style outdoor living. Opportunities like this are becoming increasingly rare in Central Florida — especially properties that combine elevation, usable land, privacy, and proximity to town. Bring your builder and create the estate lifestyle you've always envisioned.

Country Club Road S, Winter Haven
$320,000
3 Beds ⋅ 2 Baths ⋅ Lake Daisy Estates SubDv. ⋅ 33884 Zip Code
329 Lake Daisy Loop | NO HOA, Highly Motivated Seller Welcome to this beautiful 3BR/2BA home in Lake Daisy Estates, offering over 1,500 sq. ft. of comfortable living space on a spacious corner lot—and best of all, NO HOA, giving buyers the freedom they want. This home features a bright formal living and dining area, a spacious kitchen with Frigidaire appliances, and a large family room with vaulted ceilings and a wood-burning fireplace. Sliding doors open to a generous enclosed patio, perfect for relaxing or entertaining. The master suite includes a walk-in closet, jetted tub, separate shower, double sinks, and private access to the patio. Additional highlights include: Marble flooring installed in 2025, New AC (2025), Roof replaced in 2017, Window shades installed in 2025, Indoor laundry room 2-car garage Located just minutes from Legoland (5 min), Walmart (4 min), shopping centers, restaurants, schools, and medical facilities. A fantastic opportunity in a prime location with no HOA—highly attractive for today’s buyers.

329 Lake Daisy Loop, Winter Haven
$2,999,999
Fla Highland Co Sub SubDv. ⋅ 33881 Zip Code
4.3 acres fronting SR542 (Dundee Road) and cornering Sage Road. Total parcel acreage is 8.64 but only the front 4.3 is available for sale. Traffic lit, in a high growth area with recent road improvements that more readily routes traffic past the Subject towards downtown Winter Haven or towards Hwy. 27 and onto Orlando. Dundee Road becomes Central Ave. in Winter Haven, just beyond the Subject and around the picturesque lake, making for a grand entry into Winter Haven proper.  This property sits a short distance from US HWY 27 (2.8 miles) and just 3.6 miles from downtown Winter Haven. The property has many potential uses including retail, restaurants, medical, financial or other professional or business uses.

75 Sage Road, Winter Haven
$119,000
2 Beds ⋅ 1 Baths ⋅ Lucerne Shores SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. HUGE PRICE DROP! Enjoy the beauty of true Florida lakefront living on private Lake Lucerne! Situated on just over half an acre, this fully fenced waterfront property offers peaceful water views, breathtaking sunsets, and endless opportunities for fishing, boating, kayaking, or simply relaxing by the lake. Surrounded by mature trees and natural beauty. This versatile property features a grandfathered-in 3-bedroom, 2-bath single-wide mobile home offering excellent flexibility and future potential. The home includes tiedowns, a slab foundation, power, air conditioning, and a covered and screened patio area perfect for relaxing outdoors while enjoying the peaceful lakefront setting. The metal roof adds durability and functionality, while water has not been connected to the mobile home during the seller’s ownership the existing structure creates opportunities for continued use, renovation, replacement, or redevelopment. The property is grandfathered to allow replacement of the existing mobile home or the opportunity to build your own custom lakefront home. The seller is also including custom home blueprints valued at approximately $3,000 to help bring your vision to life. A major BONUS is the included 2017 KEYSTONE PASSPORT UlLTRA LITE 195RB CAMPER overlooking the lake, offering a comfortable turnkey setup perfect for weekend getaways, seasonal use, or full-time living. The camper is fully furnished and includes all furniture, décor, kitchenware, appliances, manuals, and household contents. Features include heat and air conditioning, working appliances, newer awning, newer tires including spare tire, backup camera, load distribution hitch, small grill, coffee maker, booth-style dining area, full kitchen, cozy sleeping area, and scenic lake views throughout. Additional property features include mature fruit trees such as banana, avocado, pecan, persimmon, and peach, along with a private well, septic system, metal storage shed, and convenient frontage on a main road while still maintaining a quiet waterfront atmosphere. Located in Winter Haven’s desirable lake region, this property is approximately 25 minutes from LEGOLAND Florida Resort and about 35 minutes from Walt Disney World. Whether you’re looking for a waterfront getaway, investment opportunity, or future dream homesite, this unique property captures the charm of Old Florida living while offering privacy, flexibility, and future potential.

4880 Old Lucerne Park Road, Winter Haven
$244,999
3 Beds ⋅ 2 Baths ⋅ Silvercrest Add SubDv. ⋅ 33881 Zip Code
MOTIVATED SELLERS Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. New roof 2022. Renovated bathrooms. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with direct access to the back patio. The master bedroom offers a private retreat with an en-suite bathroom and generous closet space that is connected directly to the large laundry room. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a spacious, fenced in yard with plenty of room for relaxing, gardening, or hosting gatherings. Conveniently located near Polk State College, Winter Haven schools, and just minutes away from downtown Winter Haven. This home combines peaceful living with everyday convenience. Perfect opportunity for first time homebuyers or rental property! Don’t miss the opportunity to make this move-in-ready home your own!

419 Avenue M Ne, Winter Haven
$259,000
3 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
SPACIOUS & AFFORDALE IN SOUTHEAST WINTER HAVEN, THIS 3BR/2BATH home features newer vinyl plank flooring throughout, brand new dishwasher just installed and newer kitchen cabinets! The great room has beautiful dark beams on the ceiling that give the room so much more character. Sliding glass doors open to the 10x23 screened-in patio and partially fenced & spacious rear yard for pets. Adjacent to the kitchen is an extra room, could be great for an office/den space for those who work from home. On the other side of the living area, you'll find 3 bedrooms and a guest bath with tub/shower. The primary bedroom has a walk-in closet with an en-suite bath with walk-in tiled shower. There is an oversized 1-car garage with workshop area and plenty of shelving. Located near the Lake Ned public boat ramp with kid's playground & basketball court! Great location with quick in-town access!!

404 Lake Ned Road, Winter Haven
$208,000
3 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

1100 Carefree Cove Drive, Winter Haven
$273,000
3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 33884 Zip Code
One or more photo(s) has been virtually staged. Beautifully Renovated Winter Haven Home Near LEGOLAND! Welcome to this beautifully renovated, move-in-ready home in the heart of Winter Haven! Featuring ALL NEW WINDOWS, a newer A/C system, and NEW APPLIANCES, this property offers modern comfort and peace of mind in a fantastic location. Just 2.1 miles from LEGOLAND Florida Resort, this home is perfectly suited for a primary residence, vacation getaway, or investment property. Enjoy updated finishes throughout, a functional layout, and a large fenced backyard with plenty of room for entertaining, pets, gardening, or outdoor enjoyment. Conveniently located near shopping, restaurants, medical facilities, and the many attractions Winter Haven has. With its desirable location and numerous updates, this home is an excellent opportunity for homeowners and investors alike. Renovated. Move-in ready. Great location. Endless possibilities—come see it for yourself!

137 Lowell Road, Winter Haven
$250,000
4 Beds ⋅ 3 Baths ⋅ Havencrest Add SubDv. ⋅ 33880 Zip Code
Discover a truly unique architectural gem in the heart of Winter Haven. Inspired by the timeless design style of Frank Lloyd Wright, this beautifully maintained home offers character, warmth, and distinctive architectural details rarely found in today’s market. From the moment you arrive, you’ll appreciate the clean lines, natural light, and thoughtful design elements that create a seamless connection between indoor and outdoor living. The home has been exceptionally cared for and is in very good condition, offering both charm and peace of mind. Spacious living areas, inviting atmosphere, and a layout full of personality make this property stand out from the ordinary. Whether you are looking for a primary residence, a second home, or an investment opportunity, this home delivers style and timeless appeal. Roof replaced in 2004. Conveniently located near downtown Winter Haven, shopping, dining, parks, and the Chain of Lakes. Schedule your private showing today and experience the character and beauty of this one-of-a-kind property.

317 Avenue G Se, Winter Haven
$849,000
Leslie J A Sub SubDv. ⋅ 33880 Zip Code
Exceptional investment opportunity in the growing Winter Haven / Eloise area featuring multiple parcels with income-producing and development potential. This unique package includes the commercial mechanic shop located at 204 Snively, two vacant lots at 208 Snively and 101 1st St. Eloise, plus 210 Snively featuring two residential homes on one lot. The commercial mechanic shop is currently tenant occupied at $2,500 per month, providing immediate income. The building received major updates in 2021 including a new electrical panel and split AC units. The property is connected to public water and city sewer. Positioned along a high-visibility corridor with an approximate traffic count of 17,500 vehicles per day, this location offers excellent exposure for current or future business use. 210 Snively includes two residential homes situated on one lot, with one unit currently rented for $1,000 per month and the second unit vacant, offering additional income potential or owner-user flexibility. Both residential units are connected to public water and serviced by septic systems. The included vacant lots at 208 Snively and 101 1st St. Eloise create additional possibilities for expansion, storage, redevelopment, or future development opportunities. Additional vacant lots at 205 Snively and 0 Snively are also available for added expansion and increased road frontage exposure. Conveniently located near major roadways, downtown Winter Haven, and area commerce, this multi-property package offers a rare combination of commercial income, residential income, redevelopment potential, and long-term upside. An added bonus is the properties are currently in the process of being rezoned to CAC (Community Activity Center) & Institutional, allowing the opportunity to continue the current use or transition into a variety of future permitted uses including offices, retail stores, banks, personal service businesses, and certain community facilities. This proposed zoning flexibility creates significant potential for investors, developers, or owner-users looking for future growth opportunities in an expanding area. Seller financing available!

204 Snively Avenue, Eloise
$455,000
6 Beds ⋅ 2 Baths ⋅ Laramore Sub SubDv. ⋅ 33881 Zip Code
Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright, open-concept floor plans designed for easy living and low maintenance. Step inside to find durable ceramic tile flooring flowing seamlessly throughout the main living areas and kitchens, paired with crisp, neutral paint that makes the space feel fresh and inviting. The kitchens are fully equipped with rich wood cabinetry, ample counter prep space, white appliances (including dishwashers!), and a convenient breakfast bar/passthrough that overlooks the spacious family room. To top it off, each unit includes its own dedicated in-unit laundry closet with a stackable washer and dryer—a major premium for prospective renters.

1830 2nd Street Nw Unit A, Winter Haven
$400,000
33881 Zip Code
Positioned along highly traveled Dundee Road, this prime commercial lot presents a rare, turnkey development opportunity in a growing Central Florida corridor. The property has already completed the state permitting process, significantly reducing timelines and uncertainty for a new owner or developer. With an approved driveway in place and site plans already prepared for a hotel, much of the heavy lifting has been done—allowing you to move quickly from acquisition to construction. This makes it an ideal investment for hospitality groups, developers, or investors looking to capitalize on the area’s continued growth and strong traffic exposure. Surrounded by expanding residential communities, established businesses, and convenient access to nearby attractions and major roadways, this location offers both visibility and accessibility—key components for a successful commercial venture. Opportunities like this, where planning and approvals are already secured, are increasingly hard to find. Whether you move forward with the existing hotel plans or bring your own vision to life, this property is ready to deliver.

Dundee Road, Winter Haven
$195,000
3 Beds ⋅ 2 Baths ⋅ Biltmore Shores SubDv. ⋅ 33881 Zip Code
BACK ON THE MARKET! No fault of the seller! Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!

3006 Elm Street, Winter Haven
$629,000
Winter Haven SubDv. ⋅ 33880 Zip Code
Positioned in the vibrant core of Winter Haven, this exceptional commercial opportunity offers approximately 4325 square feet, creating flexibility that's increasingly hard to find in today's market. With prime downtown visibility and convenient access to local shops, dining, and foot traffic, the property is ideally situated for both owner-users and investors seeking a strategic location. The property consists of 2 parcels with zero lot lines and includes 5 on-site parking spaces. Additionally, the City of Winter Haven has granted the property a parking exemption, providing valuable flexibility regarding municipal parking requirements for this downtown location. The building configuration opens the door to multiple income streams or a blended use concept, allowing the structure to be owner occupied while simultaneously generating rental revenue. The attached garage/studio allows for more usable space and or added storage. Designed with versatility, the space lends itself to a wide range of commercial applications- from boutique retail and professional offices to creative studio environments or wellness services. Whether you're envisioning a flagship storefront, collaborative workspace, or a commercial concept tailored to evolving business needs, this property provides the foundation to bring that vision to life. With its central downtown Winter Haven location, adaptable layout, 2-parcel configuration, five parking spaces, and City parking exemption, this property represents a compelling opportunity in one of Central Florida's steadily growing downtown districts.

155 Avenue B Sw, Winter Haven
$1,650,000
Porters Sub SubDv. ⋅ 33880 Zip Code
165 SW 5th St, Winter Haven, FL 33880 presents a strong opportunity for commercial redevelopment or investment in a growing Winter Haven location. This vacant parcel offers approximately 17,476 square feet and is positioned in an area with surrounding commercial and mixed-use activity. The site is ideal for a local owner-user, boutique developer, retail or service user, professional office, café/restaurant operator, or investor seeking a well-located parcel with redevelopment potential. With its central location and visibility, the site offers potential for an owner-user, investor, or developer seeking a parcel in an established part of the city. Buyers should verify intended use, zoning, and development requirements with the City of Winter Haven.

165 5th Street Sw, Winter Haven
$599,900
4 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 33880 Zip Code
Just extensively renovated — welcome back to 23 Oakwood Rd. This 4-bedroom, 2-bath home sits on 2.38 private, fully fenced and gated acres in Winter Haven, with no HOA and 2,125 sq ft of freshly redesigned living space. Every major surface has been touched: new luxury vinyl plank flooring, new 5-inch baseboards, and fresh paint run throughout, and removing the old half-wall opened the entry into one connected living and dining space. The kitchen was rebuilt with refreshed white cabinetry, white quartz counters, updated hardware, and a layout that flows straight into the family room. Both bathrooms got full makeovers — double-sink vanities with quartz tops, new mirrors, updated lighting, and new toilets. The split floor plan gives the primary suite its own wing, with French doors to the screened back porch, a large walk-in closet, soaking tub, separate shower, and updated double vanity. Three additional bedrooms flex easily as guest rooms, an office, or hobby space. Outside: a 42-foot covered front porch, a 34-foot screened back porch, mature trees, and room to park RVs, boats, trailers, or ATVs — or to garden, keep animals, or just spread out. A remote-gated entry secures the whole property. Recent updates: - New roof (2023) - New water heater (2026) - Updated well pump - Recently serviced septic system - New flooring, baseboards, paint throughout - Renovated kitchen and both bathrooms Room for a future pool, workshop, or other additions (subject to county approval). Minutes to the Polk Parkway, shopping, and medical facilities, with easy access to Lakeland, Tampa, and Orlando. If you toured this home before, it's worth a second look — it's not the same house. No AI staging Virtual Tour Has AI editing and Avatars

23 Oakwood Rd, Winter Haven
$319,900
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
PRICE REDUCTION! WELCOME TO YOUR NEW HOME! Experience peaceful lakefront living in a charming SE Winter Haven location, just minutes from LEGOLAND Florida Resort and the beautiful Chain of Lakes. This home is perfect for buyers looking to slow down and enjoy the simple things—morning coffee with a water view, evenings by the lake, and weekends spent fishing or unwinding in your own backyard. While the lake is smaller and offers a more quiet setting with no public boat access, that’s part of its charm—less traffic, more tranquility. Situated on a spacious lot with a fenced backyard, there’s plenty of room for pets, gatherings, or creating your own outdoor oasis. Inside, the home offers a solid foundation and a warm, inviting layout, ready for your personal style and updates to truly make it your own. If you’ve been searching for an affordable lakefront lifestyle with room to grow, this is your opportunity to put down roots and create a home that reflects you.

136 Lake Ring Drive, Winter Haven
$515,000
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
Virtually Staged. Wonderful opportunity to live in a Florida lifestyle property with two (2) ($1800 total) income-producing studio apartments on your property that are currently leased. Additionally the Airbnb potential would provide an even larger income stream since it's located only one mile from Legoland and the famous Winter Haven Chain of Lakes. This is a unique opportunity and is located on an oversized fenced corner double lot and only a 1/2 mile to Legoland. Another benefit is the bonus room could also be turned into a 4th bedroom. Plenty of paved parking for at least 10 cars. Corner lot will also allow for a detached garage to be built. No need to worry about skyrocketing electric bills as this home also has electric solar panels which are fully paid off and provide electric bill relief. Also on the property is a lovely sparkling 15' x 30' screened pool to provide escapes & privacy. There are many taste-full updates already done, including remodeled kitchen & bathrooms, new LVP throughout, newer windows, large storage shed, a hot tub, triple car wide concrete driveway & a portable back-up generator hook-up. Move-in ready and no HOA. This could also be a great place for a multigenerational living, short term rental or Airbnb.

100 Alachua Drive, Winter Haven
$269,990
3 Beds ⋅ 3 Baths ⋅ Hutton Rep SubDv. ⋅ 33881 Zip Code
"Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities, plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed with electricity in the back provides additional convenience and storage. Enjoy pure, clean water throughout the entire home with a whole-house reverse osmosis filtration system. Located on a quiet dead-end street with no through traffic. No HOA, No CDD, low taxes, public water and sewer. Just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity! Equal Housing Opportunity."

811 22nd Street Nw, Winter Haven
$329,900
3 Beds ⋅ 2 Baths ⋅ Lake Elbert Heights Unit 01 02 Rep SubDv. ⋅ 33881 Zip Code
Virtually Staged. HUGE PRICE DROP! Completely renovated Gene Leedy home and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. The stunning kitchen has been completely updated with beautiful soft-close cabinetry, luxurious quartz countertops, stainless steel appliances, and recessed lighting—offering a sleek, contemporary look and exceptional functionality. Luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint, modern fixtures, and stylish ceiling fans that complete the elegant finish. The primary suite provides a private retreat, while additional bedrooms offer flexibility for family, guests, or a home office. Both bathrooms have been tastefully remodeled with updated tile, vanities, and fixtures. Outside, enjoy your private backyard oasis—fully enclosed with a block wall for enhanced privacy. A sparkling inground pool with paver deck sets the stage for year-round Florida living, whether you’re hosting a gathering or enjoying a quiet evening under the stars. Additional features include a separate exterior laundry/storage room for added convenience. Ideally located near shopping, dining, schools, and major roadways, this home offers easy access to Winter Haven’s famous Chain of Lakes and other nearby Central Florida attractions. Every detail has been updated—move right in and start enjoying the Florida lifestyle today! Schedule your private showing before it’s gone.

1558 Drexel Avenue Ne, Winter Haven
$246,900
3 Beds ⋅ 1 Baths ⋅ Jan Phyl Village Unit 03 A SubDv. ⋅ 33880 Zip Code
Move-in ready, this charming 3-bedroom, 1-bath block home sits on a spacious lot with no rear neighbors, offering added privacy and peaceful surroundings. Inside, you’ll find updated flooring in the bedrooms and bathroom, creating a fresh and inviting feel. The home also features two versatile bonus rooms—perfect for a home office, in-law space, or even a possible 4th bedroom to suit your needs. Enjoy Florida living at its best with a screened lanai off the back, ideal for relaxing in the sunshine or entertaining guests year-round. With its flexible layout and generous outdoor space, this property offers both comfort and opportunity. Whether you're a first-time buyer or looking to expand, this home is ready for you to move right in and make it your own!

218 Dennis Avenue, Winter Haven
$175,000
5 Beds ⋅ 2 Baths ⋅ South College Add Rev SubDv. ⋅ 33880 Zip Code
Short Sale. Hard to beat this combination of size, location, and upside. Located just one street from Winter Haven’s growing downtown district, this spacious approximately 2,200-square-foot home offers investors a rare opportunity to acquire a large property in an increasingly desirable area. The home is vacant and ready for renovation. Major system updates, including dual-zone air conditioning, have been completed in recent years, allowing the next owner to focus primarily on cosmetic improvements and value-add renovations. This property is being offered as a short sale and requires an investor offer. The seller is seeking a quick, as-is transaction, and the sale will be subject to lender approval. Cash or qualified investor financing preferred. No seller financing, lease-option, or subject-to terms are being offered. Large homes this close to downtown Winter Haven are increasingly difficult to find—especially with this much potential. Bring your contractor, run the numbers, and submit your best offer.

128 Avenue D Sw, Winter Haven