Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Beds: 6+
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Winter Haven - 4 properties found
906 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$792,000149 Days on yellowkey MLS ID: L4957757
REDUCED by $88,000 (10.0%) on 04/21/2026
Bed: 9 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5700 Built: 1954 Tax: $5,237 (2024)Community: East View PkwySingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,237
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Tax Year: 2024
Middle School: Westwood Middle
Remarks: Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Brandy Duncan (863-585-6849)
461 FISH HAWK DR, WINTER HAVEN, FL 33884
$435,000101 Days on yellowkey MLS ID: O6376115
INCREASED by $20,000 (4.8%) on 04/04/2026
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3920 Built: 2006Monthly Fee: $45 Tax: $6,577 (2024)Community: Hart Lake Cove Ph 02Single Family
Taxes:$6,577
Elementary School: None
High School: None
Middle School: None
Remarks: COMPLETE REMODELING * PRIME LOCATION * HOUSE & INVESTMENT * NEW ROOF 2026 Complete remodeling house6/5 near 4,000 square feet of living area. Short distance from parks as Legoland, restaurants, malls. Great location between Tampa and Orlando. Builders don't build this king of big houses anymore. Brand new fence, new floors, walls and update bathrooms inside, owner invested more than $50,000 on new updates. Price is reduced for a quick sale. Today construction cost is $200 square feet. Get this great deal for a fraction of the original price. All concrete block construction.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Gino Dapello (954-790-0632)
15 LAKE HOWARD DR NW, WINTER HAVEN, FL 33880
$250,00028 Days on yellowkey MLS ID: TB8493899
Bed: 6 Bath: 4.0 Liv Area Sq Ft: 2883 Built: 1920 Tax: $5,897 (2025)Community: Leonards SubSingle Family
Taxes:$5,897
Elementary School: Inwood Elem
High School: Winter Haven Senior
Tax Year: 2025
Remarks: This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!
Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)
Listing Agent: Clarisa Moody (813-446-2003)
3826 GAINES CT, WINTER HAVEN, FL 33884
$1,779,90093 Days on yellowkey MLS ID: P4937567
0 Days Off yellowkey (back on 4/3/2026)
Bed: 6 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5400 Built: 1989Monthly Fee: $44 Tax: $14,471 (2025)Community: Gaines CoveSingle Family
Taxes:$14,471
Remarks: Under contract-accepting backup offers. Property is under contract with contingencies and a kick-out clause. Seller will consider backup offers. Lakefront home on the prestigious Chain of Lakes, directly on Lake Eloise, set on 1.87 acres. This three-story estate offers 6 bedrooms, 5.5 bathrooms, and a private in-law suite on the lower level, providing exceptional privacy, generous scale, and a setting designed to embrace the lake. The primary suite is thoughtfully positioned to capture sweeping lake views and serves as a true retreat, featuring a large walk-in closet and a spa-style bath with oversized shower and jacuzzi tub. Additional living spaces flow effortlessly, anchored by a chef’s kitchen with granite countertops, cherry cabinetry, and double ovens, opening to both formal and casual gathering areas ideal for entertaining. Designed for elevated living and hosting, the home includes a private movie room for a true theater experience and a spacious game and gathering room located just off the pool, creating a seamless indoor-outdoor connection. Outdoor living is a focal point of the property, highlighted by a large infinity pool within a screened enclosure overlooking the lake—an ideal setting for entertaining, relaxing, and enjoying sunset views. A private boat dock extends the lakefront lifestyle. Additional highlights include a grand circular driveway, mature shade trees, a four-car garage with space for recreational vehicles, a whole-home Generac system, and low HOA.
Listing Agent: Daniela Zoppe (407-808-7350)
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