Location: Winter Haven
Do Not Show Listings
2362 BRASSIE CT, WINTER HAVEN, FL 33884
$274,90070 Days on yellowkey MLS ID: O6384404
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1260 Built: 2022Monthly Fee: $18 Tax: $5,003 (2025)Community: VillmarSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,003
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. Nestled in the growing Villamar community, this beautifully maintained 3-bedroom, 2-bath Meritage Home offers modern comfort and an ideal location near Chain of Lakes Elementary. Built with energy efficiency in mind, this newer home features an inviting open-concept floor plan where the kitchen flows seamlessly into the spacious great room—perfect for entertaining and everyday living. The kitchen showcases quartz countertops, stainless steel appliances, a pantry, and ample cabinetry for storage. Sliding glass doors off the family living area leads to the backyard, offering easy indoor-outdoor living. The thoughtfully designed split-bedroom floor plan provides privacy, with two secondary bedrooms and a guest bath located at the front of the home, while the primary suite is tucked away off the great room. The spacious owner’s retreat includes quartz countertops, dual sinks, a walk-in tile shower, and a generous walk-in closet. Ceramic tile flooring enhances the main living areas with a clean, modern aesthetic, while the bedrooms provides comfortable carpeting. Residents of Villamar enjoy resort-style amenities, including a community pool with lap lane overlooking Crystal Lake, playground, and convenient community mailboxes. The location offers quick access to Route 27 for commuting to Orlando and is just minutes from Legoland, shopping centers, Publix, and Walmart. This community is only two miles from Legoland and in close proximity to Posner Park which offers many stores, restaurants and entertainment for your family, as well as the Orlando's theme parks. Discover the perfect blend of comfort, convenience, and community in this move-in ready home. The photographs included in this listing were taken during a previous rental listing. The property may appear slightly different at time of showing. One or more photos have been modified or virtually staged for illustrative purposes.
Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)
Listing Agent: Millie Brockmeyer (407-970-9782)
2438 4TH ST NE, WINTER HAVEN, FL 33881
$239,90052 Days on yellowkey MLS ID: L4960053
1 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1135 Built: 2026 Tax: $223 (2025)Community: Lincoln SubSingle Family
Taxes:$223
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to this beautiful brand-new construction home featuring 3 bedrooms and 2 bathrooms with a thoughtfully designed layout. This home offers tile flooring throughout, sleek stainless steel appliances, and a convenient indoor laundry room for added functionality. Enjoy the privacy of a fully fenced backyard, perfect for relaxing or entertaining. No HOA so bring all your Toys! Located in a quiet neighborhood with a great location close to shopping, dining, and everyday amenities, and just a short drive from LEGOLAND, this home combines comfort, style, and convenience. Call me today for a private showing!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Sandra Canales (863-205-2641)
1280 DENALI DR, WINTER HAVEN, FL 33881
$409,00092 Days on yellowkey MLS ID: G5107453
INCREASED by $10,000 (2.5%) on 04/05/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2566 Built: 2024Monthly Fee: $92 Tax: $6,203 (2025)Community: Lake Lucerne IiSingle Family
Taxes:$6,203
Elementary School: Bethune Academy
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: One or more photo(s) has been virtually staged. Move-In Incentive Available! Qualified buyers who finance with our affiliated lender may choose one of the following: a 4.5 interest rate or $5,000 toward closing costs (buyer must qualify; incentive applies only when using our affiliated lender). Welcome to this stunning 3-bedroom, 2.5-bath two-story home located on a quiet cul-de-sac in the desirable Lake Lucerne II community. Built in 2024 and beautifully enhanced with thoughtful upgrades, this home offers the peace of new construction with the added value buyers are looking for. The backyard is truly a showstopper, backing up to conservation land with a serene pond view, creating the perfect setting to enjoy your morning coffee or unwind at the end of the day. Vinyl fencing along the sides and a rear metal fence preserve privacy without obstructing the view. Inside, the home features high ceilings throughout, luxury vinyl flooring (with carpeted stairs and tile in bathrooms and laundry), an open-concept floor plan, and elegant design touches including a detailed foyer wall and a charming electric fireplace in the living room. The upgraded kitchen boasts stone countertops, beautiful cabinetry, stainless steel appliances, a large island with bar seating, and a pantry, making it ideal for both everyday living and entertaining. Downstairs also includes a flex room perfect for a home office or guest space, a half bath, and a 2-car garage. Upstairs, a spacious loft offers endless possibilities, family room, playroom, or potential 4th bedroom. The primary suite is a true retreat, featuring tray ceilings, generous space for a king-sized bed, and an upgraded California Closet–designed walk-in closet offering exceptional storage and organization. The primary bath includes dual sinks and a walk-in shower. Two additional bedrooms, a full bath, and a well-appointed laundry room with sink complete the upper level. Additional upgrades include a whole-home water filtration system, security system, and a hybrid heat-pump water heater that efficiently heats water while cooling the garage. Enjoy resort-style living with no CDD, a community clubhouse, two pools, and a playground. Conveniently located near shopping, golf courses, and with easy access to I-4, you’re perfectly positioned between Orlando and Tampa, sunrise to sunset. This home is move-in ready and truly special. Schedule your private showing today and experience it for yourself.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Luisa Hurtado (646-259-1153)
1148 TYLER LOOP, WINTER HAVEN, FL 33884
$265,00043 Days on yellowkey MLS ID: L4960292
4 Days Off yellowkey (back on 4/5/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2024Monthly Fee: $16 Tax: $7,039 (2025)Community: Peace River ReserveSingle Family
Taxes:$7,039
Remarks: Short Sale. SHORT SALE working on lender approval Rare opportunity to own a Next-Gen multigenerational home in Winter Haven’s Peace Creek Reserve. Built in 2023, this thoughtfully designed 4-bedroom, 3-bath residence offers over 2,100 square feet of living space and features a private in-law suite with its own entrance, kitchenette, living area, bedroom, and bathroom — ideal for extended family, guests, or potential income opportunities. The main home features an open-concept layout designed for modern living, while two covered lanais create seamless indoor-outdoor Florida lifestyle space. The property also includes a vinyl privacy fence, irrigation system, and a two-car garage. Located in a newer community in the heart of Winter Haven, residents enjoy convenient access to shopping, dining, and the Chain of Lakes lifestyle that makes Central Florida so desirable.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Sarah Armstrong (863-287-0252)
3927 PALAZZO PL, WINTER HAVEN, FL 33884
$305,00071 Days on yellowkey MLS ID: O6383833
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1597 Built: 2023Monthly Fee: $40 Tax: $4,716 (2025)Community: Villamar Ph 4Single Family
Taxes:$4,716
Remarks: Do you want to own a true one of a kind? A true one of one? This is truly a special opportunity to own a home that is as unique as it is inviting. This property is the FINAL Amarylis model available in the entire community — a rare find that offers both distinction and immediate availability. Unlike new construction opportunities that often involve lengthy build timelines, unexpected delays, and months of uncertainty, this home is completely MOVE-IN READY. No waiting, no construction process, no guesswork — just the ability to step inside and immediately begin enjoying your new home. From the moment you enter, the home creates a lasting impression. The soaring ceilings and welcoming walk-in foyer set the tone for a bright, open, and airy living experience. The elevated ceiling height dramatically enhances the feeling of space, giving the home a grand and expansive presence that feels far larger than expected. Natural light pours through the living areas, creating a warm and uplifting atmosphere throughout the day. Designed for modern living and meaningful moments, the open-concept floor plan encourages connection and comfort. The seamless flow between the kitchen, dining, and living spaces makes everyday life effortless while providing the perfect backdrop for gatherings, celebrations, and quiet evenings at home. Luxury vinyl flooring throughout the main living areas adds both style and durability, creating a cohesive and low-maintenance environment that complements any design aesthetic. Built in 2023, this residence offers the peace of mind that today’s buyers value most. Everything reflects newer construction standards, meaning you can enjoy your home without the typical concerns of replacing major components or tackling costly updates. Simply move in and focus on living. Adding even more value and convenience, the home includes a full security system with installed cameras that convey with the property, providing comfort and confidence from day one. With three bedrooms and two bathrooms, this home offers flexibility for a variety of lifestyles. Whether accommodating guests, creating a home office, or designing a playroom, the space adapts beautifully to your needs. The primary suite provides a relaxing retreat, complete with a spacious walk-in closet and a well-appointed bathroom featuring a dedicated vanity seating area — a small but meaningful touch that enhances everyday routines. Step outside and the lifestyle continues. A charming front porch offers a welcoming space to relax and unwind, while the backyard provides the perfect setting for entertaining, grilling, or enjoying peaceful outdoor moments. The included playground set adds both convenience and enjoyment. The location of the home is equally appealing, offering exceptional convenience with close proximity to a variety of shopping, dining, and everyday essentials. Residents also benefit from the community’s amenities, including a large resort-style pool with abundant seating and shaded cabana areas, as well as recreational spaces designed for enjoyment and leisure. This is more than just a home — it is an opportunity to skip the wait, avoid construction uncertainties, and immediately embrace a space designed for comfort, connection, and everyday living. Don’t miss your chance at beautiful, easy living!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Iliana Perez (407-990-7293)
2664 COUNTRY CLUB RD N, WINTER HAVEN, FL 33881
$525,00068 Days on yellowkey MLS ID: L4959468
0 Days Off yellowkey (back on 4/5/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2696 Built: 2001 Tax: $6,393 (2025)Community: Poinsettia ParkSingle Family
Taxes:$6,393
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4 bedroom, 3 bathroom pool home featuring a 3-car garage and situated on over half an acre. This expansive property offers a massive driveway, providing exceptional space for a boat, RV, or simply added privacy between neighbors—an increasingly rare find. Step inside to an inviting layout enhanced by luxury vinyl plank flooring and tile throughout. The home features a spacious front sitting room and an open-concept design that seamlessly connects the main living areas. At the heart of the home is the upgraded kitchen, complete with granite countertops, stainless-steel appliances, ample cabinetry, generous counter space, and a large island overlooking the bright and open living room—ideal for gatherings and everyday living. The primary suite offers a peaceful retreat with an ensuite bathroom featuring dual vanities, a garden tub, walk-in shower, and a walk-in closet. French doors from the primary bedroom lead directly to the screened-in patio, creating a private connection to the outdoor oasis. The additional bedrooms are located on the opposite side of the home, equal in size and conveniently positioned near two full guest bathrooms. Step outside to enjoy true Florida living on your large screened-in pavered patio overlooking the inground pool, perfect for entertaining family and friends. The property also includes a storage shed for added convenience. Recent upgrades include interior and exterior paint (2026), a new metal roof (2025), and new pool screens, offering peace of mind and move-in readiness. Located near a variety of restaurants, retailers, and everyday conveniences, this home combines space, privacy, and modern comfort in a highly desirable setting.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: John Hubbert, Jr (863-243-4024)
4270 ROBERTA DR, WINTER HAVEN, FL 33881
$315,00079 Days on yellowkey MLS ID: O6381790
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1851 Built: 2019Monthly Fee: $25 Tax: $2,961 (2025)Community: Buckeye RidgeSingle Family
Taxes:$2,961
Remarks: Gorgeous 4 bedroom, 2 bathroom, 2 car garage home located in Buckeye Ridge subdivision. Home has been well-maintained with NEW Roof 2025, Solar panels, and Tile floors. This is an open floor plan home that boasts a large room that features the kitchen, living room and dining room. Kitchen area is perfect for entertaining Family and Friends. The primary suite is a true retreat, featuring a private en-suite with dual sinks, walk-in shower, an expansive 7x8 walk-in closet, private commode, and an extra linen closet. This split plan home also features 3 more bedrooms, another full bathroom and an indoor laundry room. The sliding doors to the backyard lead you to a covered porch overlooking a fenced backyard with large pond view. Buckeye Ridge Community is perfectly situated with easy access to downtown, shopping, dining, medical facilities, and not too far from HWY 27, providing effortless travel to both Tampa and Orlando.
Listing is courtesy of: NOVAK REALTY CORP (407-347-0114)
Listing Agent: Ronald Novak (407-791-7377)
2208 LAKE BLVD, WINTER HAVEN, FL 33881
$215,00089 Days on yellowkey MLS ID: L4959022
1 Days Off yellowkey (back on 3/19/2026)
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1044 Built: 1954 Tax: $2,551 (2025)Community: InwoodSingle Family
Taxes:$2,551
Remarks: Under contract-accepting backup offers. Let's not just brag about location, location, location and not brag about the water view with amazing sunsets. This updated, clean three bedroon, one bath home is a perfact starter or for someone looking to downsize. The hardwood floors are in excellent condition. The breezeway has been inclosed and can be used in multiple ways. current owner used it for an office. The tile floor and location in the home makes it versital. Heck with a little adaption it could become a thrid bedroom with room for a second bath. This home has fresh exterior and interior paint. Theres is an oversized one car garage and loft storage and there is a shed on the property. There are solar panels which almost eleminate the power bill --- averages about $25 month. They will be paid off by the seller at closing. The location is convenient to US 92, on a corner lot, with only one neighbor. A lake and Park across the street means not front neighbors, they corner lot means no rear neighbors. Priced to sell, don't let this one slip away. Give me a call for your private tour. New Roof will be installed after claim is settled (60-90) days.
Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)
Listing Agent: Jim Hampton (863-266-5666)
1640 NW PEARCE RD, WINTER HAVEN, FL 33881
$345,000275 Days on yellowkey MLS ID: L4954651
0 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1421 Built: 2025Community: Lake View Sub Pb 3 Pg 80Single Family
Taxes:$0
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Discover the perfect blend of modern living and convenience in this brand new 3-bedroom, 2-bathroom home located in the heart of Winter Haven, just minutes from the serene shores of Lake Hartridge. Best of all, there’s NO HOA to worry about! As you step inside, you’ll be greeted by a bright and airy open floor plan that flows seamlessly throughout the home. The luxury vinyl plank flooring adds both elegance and durability, making it a great choice for busy households. The heart of the home is undoubtedly the beautiful kitchen, which features stainless-steel appliances, quartz countertops, and plenty of cabinetry to store all your cooking essentials. The kitchen design allows for easy interaction with guests in the spacious living room, ensuring you never miss a moment while entertaining. Retreat to the primary bedroom, a sanctuary designed for relaxation. This inviting space comes complete with a generous walk-in closet and a luxurious ensuite bathroom, featuring dual sinks and a modern walk-in shower—providing a perfect spot to unwind after a long day. The two additional bedrooms are thoughtfully designed with equal sizing and each boasts a walk-in closet, ideal for family members or guests. The second bathroom, conveniently located near the entrance of the home, includes a shower and tub combination, offering both comfort and functionality. Situated in the heart of WinterHaven, this home places you in close proximity to a variety of retailers, restaurants, and shops, ensuring you have everything you need right at your fingertips. Plus, the adjacent home is also available for sale and currently under construction, offering a unique investment opportunity. Don’t miss your chance to own this exceptional new home in Winter Haven—schedule a tour today and envision the possibilities!
4576 BACK NINE DR, WINTER HAVEN, FL 33884
$344,500120 Days on yellowkey MLS ID: P4937279
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1514 Built: 2019Monthly Fee: $5 Tax: $1,937 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$1,937
Remarks: Welcome to a wonderful new chapter in Lake Ashton, Central Florida’s premier fifty-five plus active adult community, where this thoughtfully maintained two bedroom, two bath home offers comfort, style, and peace of mind. Recently refreshed with exterior and interior paint, enhanced energy-saving features include additional attic foil insulation, and surrounded by pristine landscaping, the home immediately makes a welcoming impression with its screened front entry, elegant stone veneer, and newly sealed veneer and pavers. Inside, the living room feels open and inviting beneath a cathedral ceiling and new vinyl plank flooring, while the spacious primary suite and separate guest bedroom and bath provide privacy and relaxation for both owners and visitors. The kitchen is both functional and attractive with solid wood cabinetry and granite countertops, and the generously sized screened veranda creates the perfect setting for quiet mornings, relaxed evenings, or easy entertaining. This home truly shines when experienced in person, and life at Lake Ashton extends far beyond the front door with two championship golf courses, an expansive clubhouse, fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and an array of activities that make every day feel full and rewarding. Blending comfort, convenience, and an exceptional sense of community, this inviting property is ready to welcome you home and offer the very best of Florida living.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)
Listing Agent: Brad Kirwan (863-280-0390)
6625 THORNHILL RD, WINTER HAVEN, FL 33880
$299,900392 Days on yellowkey MLS ID: L4951980
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1221 Built: 2024 Tax: $569 (2024)Community: Thornhill OaksSingle Family
Taxes:$569
Elementary School: Eagle Lake Elem
Middle School: Westwood Middle
Remarks: ***BELOW MARKET VALUE*** New Construction 3 Bedrooms 2 Baths built by the best builder in the area WCM Construction! This home is built with high quality kitchen and bathroom cabinetry, Level 3 Granite counters throughout kitchen and baths, high end appliances, beautiful wood grain tile throughout the entire home - no carpet or wood. Built with perfection, yet affordably priced! Check out the complete walk-thru video or better yet, call for an appointment to see this beauty in person!
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Barry Macchione (863-604-7455)
5132 SYLAS JAX AVE, WINTER HAVEN, FL 33884
$370,09028 Days on yellowkey MLS ID: L4960822
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2587 Built: 2026Monthly Fee: $17Community: VillamarSingle Family
Remarks: Under Construction. New construction home with 2587 square feet two-story including 4 bedrooms with loft, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 3 and 4 share a jack-and-Jill bathroom. Plus, enjoy a 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey."
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
287 INMAN BLVD, WINTER HAVEN, FL 33881
$315,00028 Days on yellowkey MLS ID: S5147134
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 2023Monthly Fee: $49 Tax: $3,542 (2025)Community: Inman Grvs Ph 2Single Family
Taxes:$3,542
Elementary School: Elbert Elem
High School: Winter Haven Senior
Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Chris Loschiavo (863-280-2201)
104 11TH ST SE, WINTER HAVEN, FL 33880
$295,90028 Days on yellowkey MLS ID: P4938332
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1792 Built: 1953 Tax: $3,956 (2025)Community: East El Otis Park RepSingle Family
Taxes:$3,956
Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 3-bath home located in one of Winter Haven’s most established and sought-after neighborhoods. Situated on a spacious 0.26-acre lot, this property offers timeless character, mature surroundings, and a location rich in local history. A standout feature of the home is the private suite with its own entrance and full bathroom, ideal for guests, extended family, or a flexible work-from-home space. The layout provides both privacy and functionality, making it a rare find in this area. Recent updates include a newer roof (approx. 1 year old), updated electrical, a new water heater, and a newer A/C unit (2018), offering peace of mind on major systems. Enjoy the unique setting with nearby views of Lake Elbert to the north and Lake Otis to the south, surrounded by well-established homes and nearby lakefront properties. The home offers great bones and classic charm, presenting an excellent opportunity for buyers to update and personalize while investing in a premier location. Conveniently located near downtown Winter Haven, shopping, dining, and more.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Dave Westphal (863-287-3302)
411 AVENUE A SE, WINTER HAVEN, FL 33880
$215,000276 Days on yellowkey MLS ID: L4954810
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1240 Built: 1958 Tax: $1,474 (2024)Community: Denison Heights Estates Rep PtSingle Family
Taxes:$1,474
Elementary School: John Snively Elem
Remarks: Perfect BLOCK home for the first time home buyer, investor or seasonal owner - and a prime investment property for consideration as well. Located in a wonderful mature neighborhood zoned as a MIXED USE area; so there is potential to convert this Residential home into an Office or a Business! Offering quick access to every amenity imaginable and close to the Heart of Winter Haven. Currently a 2 bedroom home with a bonus room, could be 3 or 4 bedrooms with conversion of the bonus room and/or the garage. The large lot is between 1/4 & 1/2 Acre size with a fenced backyard. Roofing and electrical was recently updated. A great piece of real estate with lots of opportunity!
Listing is courtesy of: NUWAVE REALTY (386-473-9765)
Listing Agent: Penny Miller (386-473-9765)
3826 GAINES CT, WINTER HAVEN, FL 33884
$1,779,90090 Days on yellowkey MLS ID: P4937567
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)
260 GREENFIELD RD, WINTER HAVEN, FL 33884
$393,00080 Days on yellowkey MLS ID: P4937787
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1947 Built: 1978Monthly Fee: $152 Tax: $5,885 (2025)Community: Cypresswood Greenfield VillageSingle Family
Taxes:$5,885
Remarks: Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours. AGENTS, please see remarks.
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
688 AUGUSTA RD, WINTER HAVEN, FL 33884
$337,00065 Days on yellowkey MLS ID: P4937966
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1586 Built: 1980Monthly Fee: $137 Tax: $3,636 (2025)Community: Cypresswood Fairway Patio HomesSingle Family
Taxes:$3,636
Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!
2336 W CANNON TER NW, WINTER HAVEN, FL 33881
$729,000108 Days on yellowkey MLS ID: L4958323
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1856 Built: 1995 Tax: $6,634 (2025)Community: West Cannon TerraceSingle Family
Taxes:$6,634
Remarks: HUGE PRICE DROP! Completely renovated home with new pool on Cannon Lake! Welcome to your dream lakeside retreat on a sprawling lot with 120 feet of pristine lakefront on Lake Cannon. This completely renovated three-bedroom, two-bathroom home boasts an open floor plan with high ceilings and a desirable split-bedroom layout. The stunning kitchen features granite countertops, a counter-height breakfast bar, and brand-new Samsung bespoke appliances, including an induction stove, perfect for culinary enthusiasts. The expansive primary suite offers a luxurious en suite bath with a large shower equipped with multiple showerheads, including a rain showerhead, and sliding glass doors that lead to an impressive outdoor entertaining space. The screened-in patio, perfect for hosting gatherings, overlooks the brand-new saltwater, heated pool and spa, completed in 2025, creating an idyllic setting for relaxation and fun. Additionally, the home features a new roof and new windows, ensuring peace of mind for years to come. Enjoy unobstructed views of the lake from your large outdoor area, ideal for summer barbecues or evening stargazing. Conveniently located near shopping, restaurants, and entertainment, this home truly offers the best of lakeside living on the chain of lakes.
Listing Agent: David Small (407-601-8351)
2800 SUNSET DR NW, WINTER HAVEN, FL 33881
$349,000316 Days on yellowkey MLS ID: P4935252
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 1972 Tax: $1,432 (2024)Community: Idylwild HeightsSingle Family
Taxes:$1,432
Elementary School: Walter Caldwell Elem
Remarks: One or more photo(s) has been virtually staged. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing blend of suburban tranquility and convenient urban access.
Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)
Listing Agent: Lucy Martinez (863-521-4156)
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