Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Price: $1,000,000+
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Winter Haven - 3 properties found
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,471
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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 is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Daniela Zoppe (407-808-7350)
13 BOGEY DR, WINTER HAVEN, FL 33881
$1,895,000111 Days on yellowkey MLS ID: L4958559
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 4708 Built: 1994 Tax: $7,481 (2025)Community: N/ASingle Family
Taxes:$7,481
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.
Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)
Listing Agent: Brock Jennings (863-990-5846)
1123 CYPRESS PT W, WINTER HAVEN, FL 33884
$1,150,000288 Days on yellowkey MLS ID: P4934938
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2713 Built: 1977Monthly Fee: $29 Tax: $6,114 (2024)Community: Cypress PointSingle Family
Taxes:$6,114
Tax Year: 2024
Remarks: ELEGANT POOL HOME ON CHAIN OF LAKES! Paradise awaits you at this fabulous lakefront residence that offers the ultimate in comfort, space and sunset views Thoughtfully designed for lake living and entertaining, the home captures the beauty of Lake Eloise from both, inside and out. This home is situated on .72 acres with fencing, dock, boathouse and on a quiet cul de sac. Inside this spacious residence are 3 bedrooms, 3.5 baths, formal rooms and plenty of relaxed living space. The handsome two-story entry hall features a beautiful staircase and Mexican tile flooring. This foyer is flanked by the formal living room and formal dining room, both showcasing gorgeous wood floors and fabulous millwork of chair railing, crown molding and finish work, all of which continues throughout much of this custom home. The wonderful kitchen boasts beautiful wood cabinets, including pantry-style, a center island w/seating, gorgeous granite counters, stainless appliances, a desk area with bookcase and handy pass-throughs to the casual dining room, family room and the lanai. An impressive family room is perfect space for family and when entertaining guests as it presents meticulous mill work, a warm fireplace, wet bar, durable, attractive Mexican tile flooring, with access to the lanai, spacious pool area and amazing view across Lake Eloise. A lovely guest bedroom is adjacent to the family room and a full bathroom with an attractive tile shower and stone countertop vanity. The second level of the home houses two, spacious master en suites situated on either side of a bonus room that is ideal as den or office. The primary master’s suite has a wonderful view of the lake and an elaborate layout with his and her dressing rooms that include remarkable wardrobes and closet systems; this suite has a luxurious bathroom outfitted with hydro-spa tub, extraordinary walk-in shower with multi-spray heads and bench, plus a lengthy dual sink vanity. The additional upstairs en suite has a large walk-in closet, single sink vanity and a tile walk-in shower. A special room-with-a-view is the library/reading room that is adjacent to the bonus room; the wall of windows gives a panoramic view across the property and lake. The back lanai, patio and pool area is a true highlight that is perfect for relaxation or entertainment. Here, you’ll find an outdoor kitchen, heated pool & spa creating a serene setting for lounging, swimming, or hosting gatherings with friends and family. Outdoor enthusiasts will delight in the lakefront provisions of the fishing dock and boathouse with lift and metal roof; spend the day out fishing and boating or enjoy a sunset cruise throughout the Winter Haven Chain. Don’t miss this exceptional opportunity to embrace a lifestyle of elegance, convenience in your own slice of paradise of Central Florida! Call today for a private tour of the home and property.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Erin Floyd (863-412-2286)
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