Browse All Winter Haven FL Properties for Sale

Entitled land! 14 Unit townhome development approved and ready for construction immediately! 1.57 acres consisting of 103 feet of lake frontage on Lake Buckeye in Winter Haven. Documents will be provided upon requests.

1530 11th Street Ne, Winter Haven

$179,999

2 Beds ⋅ 2 Baths ⋅ Stonebridge Vls Ph 02 SubDv. ⋅ 33880 Zip Code

Turnkey Villa in Stonebridge — Low Maintenance Living, Prime Location Step into easy Florida living with this move-in ready 2-bedroom, 2-bath villa in the highly desirable Stonebridge community. With vaulted ceilings, abundant natural light, and an open-concept layout, the home feels bright, spacious, and immediately inviting. The thoughtfully designed split-bedroom floor plan offers ideal privacy for guests, roommates, or a dedicated home office. The primary suite provides a relaxing retreat with a walk-in closet and a spacious walk-in shower. The kitchen is both functional and welcoming, featuring generous counter space, ample cabinetry, and a breakfast bar that flows seamlessly into the main living area—perfect for everyday living or casual entertaining. Major systems—including the roof, HVAC, and water heater—are all approximately 3 years old, giving buyers peace of mind from day one. Step outside and enjoy one of the home’s standout features: direct proximity to the community pool—just steps away for effortless relaxation. Conveniently located near downtown Winter Haven, Legoland, Disney, and major roadways with access to Florida’s beaches, this home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Opportunities like this don’t last—schedule your private showing today.

2218 Abbey Road, Winter Haven

$215,000

2 Beds ⋅ 2 Baths ⋅ Vienna Square Duplex SubDv. ⋅ 33884 Zip Code

Virtually Staged. MAKE AN OFFER!! - THIS IS NOT THE SAME HOME BUYERS MAY REMEMBER! This inviting villa has been refreshed and is ready to make a brand-new impression. Recent improvements include fresh interior paint, new carpet in both bedrooms, brand-new stainless-steel kitchen appliances, a freshly painted garage floor, and a new glass shower door in the primary bathroom. Located in the gated 55+ community of Vienna Square, this move-in-ready 2-bedroom, 2-bath villa offers 1,118 square feet of comfortable, single-story living. The bright, open living area, functional kitchen, spacious primary suite, attached two-car garage, and screened rear porch provide an easy, low-maintenance Florida lifestyle. Community amenities include a clubhouse, swimming pool, fitness center, recreational facilities, and organized social activities. Monthly fees also include cable television, water, lawn and grounds maintenance, pool maintenance, and recreational facilities. If you viewed this property before the improvements were completed, come back and see the difference. At $215,000 this refreshed home deserves a fresh look. Schedule your private showing today!

1224 Vienna Square Drive, Winter Haven

$175,000

33880 Zip Code

**Prime Commercial Lot for Sale – Spirit Lake Road, Winter Haven, FL** **Location, Location, Location!** This is a rare opportunity to own a prime commercial lot in one of Winter Haven's highest-traffic areas. Located directly on Spirit Lake Road, this vacant parcel is surrounded by thriving businesses, making it an ideal spot for your next commercial venture. With McDonald's as your neighbor, you’ll benefit from the constant flow of foot and vehicle traffic. Additionally, the lot is just a short distance from the Polk Parkway and the world-famous Legoland Florida Resort, bringing millions of visitors to the area each year. **Property Highlights:** - **High Traffic Exposure**: Located in a bustling commercial corridor, providing maximum visibility and easy access for customers. - **Proximity to Major Attractions**: Just minutes from Legoland and the Polk Parkway, ensuring a steady stream of potential customers. - **Neighboring McDonald's**: High-traffic area with established businesses, ensuring you’re in great company. - **Ideal for Retail, Dining, or Office Use**: The flat, spacious lot is versatile and ready for your business ideas. - **Easy Access**: Great road frontage and access to major routes ensure customers will have no trouble finding your location. Whether you're looking to expand your business, open a new restaurant, or develop a retail center, this lot offers an exceptional location to achieve your goals. The combination of high visibility, prime location, and proximity to major attractions makes this an unbeatable investment opportunity. **Don’t miss out on this incredible chance to own a piece of Winter Haven’s commercial future. Contact us today for more information and to schedule a showing!**

Spirit Lake Road, Winter Haven

$379,000

3 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code

One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $10K PRICE IMPROVEMENT on 7/24! Now offered at another improved price, this waterfront home on Lake Rochelle delivers the best value currently available on the Winter Haven Chain of Lakes. Located in the desirable Island Lakes community, this well-maintained 3-bedroom, 2-bath home combines lakefront living, major recent updates, and everyday functionality. A brand new roof was installed in February 2026, offering added peace of mind and potential insurance advantages for the next owner. Fresh landscaping and new sod create excellent curb appeal, while the open split-bedroom floorplan provides comfortable living with beautiful natural light throughout. The spacious primary suite overlooks the water and includes a private bath and walk-in closet. The living and dining areas flow easily into the kitchen, making the home ideal for entertaining, weekend guests, or simply enjoying the lake lifestyle. Step outside and enjoy direct access to the Chain of Lakes with boating, fishing, kayaking, and sunset views right from your backyard. Conveniently located near shopping, dining, medical facilities, and major roadways while still offering a peaceful waterfront setting. Whether you’re looking for a primary residence, winter retreat, or investment opportunity, this property checks all the boxes for Florida lakefront living. Schedule your private showing today.

4099 Island Lakes Drive, 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

$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

$279,900

3 Beds ⋅ 2 Baths ⋅ Peach Crossings SubDv. ⋅ 33884 Zip Code

NO CDD fees! Welcome to Peach Crossings, Winter Haven’s newest community! This brand-new three-bedroom, two-bathroom home is designed for both comfort and style. The kitchen is the heart of the home, offering ample counter space—perfect for meal prep and entertaining. It comes fully equipped with Whirlpool stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! Granite countertops and modern cabinetry provide a classic, elegant touch. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy the outdoors year-round with the covered patio, a great spot for dining, relaxing, and taking in the fresh air—made even better by the privacy of having no rear neighbors and a beautiful pond view. This home is packed with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom off the garage offers the perfect drop zone for shoes, bags, and coats, making daily routines easier. Located next to the laundry room, this space helps keep everything organized and clutter-free. Situated in Polk County, Peach Crossings offers a balance of peaceful lake life and easy access to shopping, dining, and major attractions. Families will love the top-rated Polk County schools, and the community features a playground and picnic area for all to enjoy. Don’t miss out on this incredible opportunity—schedule your tour today!

1787 White Elephant Loop, Winter Haven

$193,000

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

NEW LOWER PRICE!! This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one, call to view today. Flood zone area is deemed to be correct but must be verified by buyer/buyer broker.

683 Broadmoor Circle Unit 683, Winter Haven

$248,000

2 Beds ⋅ 2 Baths ⋅ Vienna Square Phase 3a SubDv. ⋅ 33884 Zip Code

NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver driveway, granite counter tops, shaker cabinets, new Whirlpool appliances, Delta fixtures, designer lighting, inside laundry and more. In the owners retreat, there is a walk-in closet and tiled walk-in shower. The guest bathroom has a tub/shower combo. Lawn maintenance and most exterior maintenance are included in the monthly HOA dues, along with Spectrum basic cable/internet, access to the clubhouse, heated pool, fitness center, and more. This new home comes with a structural warranty. Call today!

1703 Linz Court, Winter Haven

$139,000

2 Beds ⋅ 2 Baths ⋅ Royal Crescent Condo SubDv. ⋅ 33884 Zip Code

Welcome to your new home located directly across the street From Legoland. Home features community pool and tennis court and is ready for a new owner. Located in the central Hub of Winter Haven and close to anything any everything you need. Shopping, restaurants, schools.

5850 Cypress Gardens Boulevard Unit 304, Winter Haven

$250,000

3 Beds ⋅ 2 Baths ⋅ Osprey Landings Ph 01 SubDv. ⋅ 33880 Zip Code

Beautiful 3BR/2BA home in a gated community of Osprey Heights. All floors are covered with wood laminate. The Solar system is paid off and included in the price of the home with no extra payment.

123 Osprey Heights Drive, Winter Haven

$169,000

Home Park Unit 1 Replat Pb 28 Pg 39 SubDv. ⋅ 33880 Zip Code

Please note: Price reduction. Curt Campbell is my brother and I represent his interest in this Transaction. This property features access to the Winter Haven Chain of Lakes and there is NO HOA.

709 Lake Shipp Drive S, Winter Haven

$169,000

33880 Zip Code

Please note: Reduced price. Curt Campbell is my brother and I represent his interest in this Transaction. This property affords access to the Winter Haven Chain of Lakes and there is NO HOA. This property accesses the canal which takes you to Lake Shipp and the Chain of Lakes.

Z Avenue Sw, Winter Haven

$360,000

5 Beds ⋅ 3 Baths ⋅ Squires Grove Ph 2 SubDv. ⋅ 33880 Zip Code

Minutes from Legoland and Peppa Pig Theme Park, this 5-bedroom, 3-bath home offers comfort and functionality in a quiet cul-de-sac. The open-concept layout features a spacious kitchen, main-floor den, and a first-floor guest suite with full bath. Upstairs includes a versatile loft and a primary suite with walk-in closet and dual vanity. Additional highlights include second-floor laundry, tile in wet areas, a 2-car garage, and a large backyard ideal for entertaining. Conveniently located near shopping and dining. Low HOA—perfect for first-time buyers or investors. (Tenant Occupied - Lease ends October 2026)

821 Sun Burst Road, Winter Haven

$6,000,000

33880 Zip Code

Residential Land Location in Winter Haven, FL. Proposed 368 Units - Residential Multi-Family. Winter Haven is a city in central Florida, known for its canal-linked Chain of Lakes. Several lakes have waterside parks and eateries, as well as boat ramps and water-sports rentals. On Lake Eloise, Legoland Florida Resort includes Cypress Gardens, a 1930s botanical garden, and Lego-brick attractions, rides and a water park. West of the city, Circle B Bar Reserve has forest trails and alligator-inhabited wetlands. Final Engineering approved - All permits done. Just few miles from Supermarkets, Retail, Restaurants Doctors office and more. Excellent Location with easy access to Hwy 27 and I-4

Monroe Road, Winter Haven

$3,750,000

33884 Zip Code

Property has access to traffic signal via Lake Fox Drive. Zoned C-3 in City of Winter Haven. Permitted uses include hotel/motel, retail center, professional offices, restaurants, & more. Seller will consider dividing.

Cypress Gardens Boulevard, Winter Haven

$238,000

Southaven SubDv. ⋅ 33880 Zip Code

Amazing commercial property ready for a business. Backs up to CSX railroad tracks. Property is in the Elouise CRA so tax incentives are available.

3rd Street, Winter Haven

$495,000

33884 Zip Code

This property is located on Pollard Road, which has just been repaved. With the new easement, acquired by the City of Winter Haven, street lights have been added and also City water and City sewer is available. And best of all there is NO HOA. This property is in a rural setting, with the occasional train passing by, yet, less than 5 miles from Publix or the local theme park. Currently, this property is in the county of Polk, but surrounded by the City of Winter Haven. This property was once a grove and as indicated by the FEMA flood plane map is high and dry with good drainage.

Pollard Road, Winter Haven

$980,000

33881 Zip Code

9.8 ACRES (8.5 acres of R-3 + 1.3 acres of Conservation zoning) in the City of Winter Haven. Prime location and already zoned for multifamily development (R-3). Additional unit count with potential zoning change of 1.3 acre portion to R-3. WATER, SEWER & POWER readily available! Property fronts onto Brigham Road and backs up to a Conservation Area. All measurements including acreage count are approximate to be determined by accurate survey.

Brigham Road, Winter Haven

$4,500,000

33884 Zip Code

6.82+/- Acre Self Storage Development Opportunity. Commercial zoning allows for Self Storage. The property is cleared and graded. This development project includes Lots S10, S11, and S12 shown on the attached map. The utilities are at the site. Once the buyer provides their conceptual plans for a self-storage project, the Seller's engineer can have full plans ready to submit within 4-6 weeks and approval within approximately 3 months. This project is part of a massive 450 (+-) Acre Mixed-Use Development project located just off Hwy 27 in Winter Haven.

Thompson Nursery 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

$850,000

Royonne Place Resub SubDv. ⋅ 33884 Zip Code

“Extraordinary Commercial Property” - This 5.33-acre commercial vacant land site is a rare opportunity to own a prime piece of real estate on busy Cypress Gardens Boulevard. With 550 feet of road frontage, this property is made up of 4 separate parcels & includes a small lake of about 1.5 acres (Lake Rey) (Lake Rey is classified as a Lake in Polk County, Florida). with 2 access points on either side of the lake off Cypress Gardens Blvd. The utilities available include city water, electric, gas-LP, and public sewer. The land use designation of CR (Commercial Retail) by The City of Winter Haven is within the city limits. It allows commercial development with any retail, including but Not Limited to retail strip centers, restaurants, stand-alone retail stores, etc. This property is on the primary east/west commercial corridor in this part of Winter Haven & is minutes away from LEGOLAND Florida. Don’t miss out on this outstanding opportunity to develop and clear this land with commercial improvements. Easy access to Us Hwy 27, and Downtown Winter Haven. There Is Little to No Remaining Vacant Commercial Development Parcels Alone, this is a Highly Traveled Roadway Great traffic and potential exposure. Close to The Chain of Lakes Complex Redevelopment - (This is a major development that will occur in Winter Haven over the next several years). The listing price includes all four parcels and is set at $999,000. Parcel A has the physical address of 1101 Cypress Gardens Boulevard. Outstanding location for many prospective uses. The property was formerly known as Slocum Water Gardens.” Seller is willing to entertain any and all requests you put in your offer.

1101 Cypress Gardens Boulevard, Winter Haven

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Winter Haven Homes For Sale

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Winter Haven Florida Information:

Winter Haven, Florida is located in Polk County, just west of Orlando, and east of Tampa. With a population of nearing 50,000, it is a charming and picturesque community that is known for its beautiful lakes and mild winters.

Winter Haven is known as the Chain of Lakes City because of the 48 lakes that surround it. These lakes provide opportunities for fishing, boating, swimming, and other water sports. There are also several restaurants and bars that are accessible by boat.

The city is also home to a number of parks and recreation areas, including Legoland Florida, which is a popular theme park with a water park.

The Chain of Lakes is a series of interconnected lakes in Polk County that is 14 of the lakes connected via canals. The Chain of Lakes is a popular destination for fishing, boating, and other water sports. The canals are now used for recreation, and are a popular destination for boating, fishing, and swimming.

We have a page specifically for Homes For Sale on the Chain Of Lakes.

Winter Haven is a popular tourist destination due largely to Legoland, and is home to a number of hotels, restaurants, and shops. Being a popular area with snowbirds, we also have many wonderful 55+ communities in the area.

If you are thinking about buying a home in Winter Haven, Give us a call! We are locals that know the area well. Check out our youtube channel to see more information on the area.