Location: Winter Haven
Do Not Show Listings
1100 MARTINIQUE DR #105, WINTER HAVEN, FL 33884
$55,00010 Days on yellowkey MLS ID: G5113424
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 663 Built: 1974Monthly Fee: $232 Tax: $974 (2025)Community: Orchid Spgs Vill 300 BarcelonaCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$974
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Spacious condo with 1 bedroom, laundry inside, bonus patio area and on 1st level. Easy to maintain so you have the flexibility to travel and relax. The kitchen is white and bright and living room/dining combo offers an open floor plan. This home feels comfortable and cozy. This condo comes with an assigned parking spot. Close to restaurants, shopping lakes and a variety of activities.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Tina Mcdonald (989-385-5757)
542 LAKE DEXTER BLVD, WINTER HAVEN, FL 33884
$240,00010 Days on yellowkey MLS ID: L4962517
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1131 Built: 1987Monthly Fee: $33 Tax: $2,905 (2025)Community: Lake Dexter Woods Ph 02Single Family
Taxes:$2,905
Remarks: Welcome to this charming home in the desirable Lake Dexter Woods community of Southeast Winter Haven. This well-maintained residence offers comfortable living with an open and inviting layout, spacious living areas, and abundant natural light throughout. The kitchen provides ample cabinet and counter space, while the primary suite features a private bath and generous closet storage. Enjoy Florida living year-round from the enclosed Florida room, perfect for relaxing or entertaining. The property also features a fenced backyard with mature landscaping and low-maintenance outdoor spaces. Residents of Lake Dexter Woods enjoy access to community amenities including a pool, boat ramp, and dock with access to Lake Dexter. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers both comfort and convenience in a sought-after location. This home has lots of updates! lighting, electrical panel and outlets, plumbing, 2021 Water heater, 2024 Roof, 2025 HVAC.
Listing is courtesy of: DILIGENCE LLC (727-400-5063)
Listing Agent: Malachi Gaddis (941-875-2111)
5580 STATE ROAD 542 W, WINTER HAVEN, FL 33880
$235,000217 Days on yellowkey MLS ID: A4671922
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2174 Built: 1952 Tax: $1,740 (2024)Community: Jan Phyl VillageSingle Family
Taxes:$1,740
Tax Year: 2024
Remarks: PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jen Victor (941-587-2787)
3337 COSTELLO CIR, WINTER HAVEN, FL 33884
$345,000131 Days on yellowkey MLS ID: L4959241
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2522 Built: 2023Monthly Fee: $17 Tax: $7,388 (2025)Community: Villamar Phase 5Spa: NoSingle Family
Taxes:$7,388
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: McLaughlin Academy Of Excellence
Remarks: Why buy new when this is BETTER than NEW? This immaculate and spacious home features 5 bedrooms, 3 baths, 2 car garage, a fenced backyard and a water view! What more could you ask for? It’s the perfect blend of comfort and affordability with a modern style. The home features an open concept living room, dining room and kitchen. Perfect for entertaining! The sellers have removed the standard Formica countertops in the kitchen and bathrooms and replaced them with a beautiful white Quartz! But that's not all, they also replaced the carpet on the stairs with a beautiful Red Oak wood, fenced in the backyard, updated the faucets, fixtures, and hardware throughout. They also added a shiplap accent wall in the upstairs loft and laundry room. There is one bedroom and one full bathroom located on the main floor ideal for guests or someone that can't climb stairs. Upstairs, you'll notice the versatile loft space that is currently being used as a home office but would also work as a playroom or 2nd living area. The generous primary suite with a huge walk in closet and en-suite bathroom, along with 3 additional bedrooms, a bathroom and the laundry room are also located upstairs. The fully fenced backyard provides privacy and is the perfect place to unwind and relax. Located in a desirable and quiet community close to dining, shopping, schools, entertainment, and major highways. Don't miss out on this beauty!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Mindy Russo (863-812-1294)
5351 MICKEY AVE, WINTER HAVEN, FL 33884
$308,950209 Days on yellowkey MLS ID: S5138935
INCREASED by $8,951 (3.0%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
840 PIEDMONT DR SE, WINTER HAVEN, FL 33880
$425,00012 Days on yellowkey MLS ID: L4962339
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1870 Built: 1960 Tax: $4,220 (2025)Community: Cooper EstatesSpa: NoSingle Family
Taxes:$4,220
Remarks: Welcome to your own private backyard retreat in the heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bath pool home sits on a spacious .31-acre lot with NO HOA and offers the perfect blend of comfort, convenience, and Florida living. The true showstopper is the incredible approximately *983-square-foot covered lanai*, creating an expansive outdoor living space rarely found in homes of this size. Perfect for entertaining, relaxing, outdoor dining, or even a home gym, this massive covered retreat overlooks the sports-style pool, oversized fenced backyard, custom playground, firepit, raised irrigated garden beds, and turf-and-tile entertaining area. Best of all, enjoy spectacular *LEGOLAND fireworks* views right from your own backyard. Inside, you'll find a bright and inviting floor plan with generous living spaces, comfortable bedrooms, and a well-appointed kitchen that flows seamlessly into the living and dining areas. Recent updates provide peace of mind, including a New Roof (2023), New Covered Lanai (2023), whole-home re-plumbing (2024), reverse osmosis system in the kitchen (2024), stainless steel dishwasher (2021), gas water heater (2021), irrigation system for yard (2023), updated light fixtures throughout, Ring security system with automatic flood lights, and added recessed lighting in the living room and kitchen. The outdoor space was thoughtfully enhanced in 2024 with stained fencing, rocked and irrigated landscape borders, a fully sealed playground, and beautifully designed gathering spaces that make this property ideal for everyday living and entertaining alike. Conveniently located just minutes from Downtown Winter Haven, LEGOLAND Florida Resort, major hospitals, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect combination of location, lifestyle, and value. Don't miss this rare opportunity to own a beautifully updated pool home with an extraordinary outdoor living experience. Schedule your private showing today!
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Jenna Henderson (850-524-3843)
3097 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$449,00016 Days on yellowkey MLS ID: S5150948
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2577 Built: 2004Monthly Fee: $33 Tax: $4,587 (2025)Community: Buckeye PointeSpa: YesSingle Family
Taxes:$4,587
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Desiree Carlson (541-743-1985)
205 ARBUTHNOT ST, WINTER HAVEN, FL 33881
$299,77762 Days on yellowkey MLS ID: S5148024
REDUCED by $223 (0.1%) on 06/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1447 Built: 2022Monthly Fee: $84 Tax: $2,856 (2025)Community: Sanctuary By The Lake Phase OneSingle Family
Taxes:$2,856
Remarks: PRICE TO SELL!!!UP TO $5,000 IN BUYER INCENTIVES AVAILABLE! This property may qualify for up to $5,000 in closing cost credit when using the seller's preferred lender. Ask us how to qualify! Welcome to Sanctuary by the Lake — one of Winter Haven's most sought-after gated lakefront communities, built by Southern Homes along the stunning shores of Lake Rochelle, part of Florida's renowned Chain of Lakes. Whether you're looking for your forever home or a high-demand investment property, this one checks every box. This move-in ready, beautifully upgraded 3-bedroom, 2-bathroom home seamlessly blends modern design with relaxed lakeside living. Step inside to a spacious foyer that opens into a bright, open-concept living and dining area filled with natural light. Glass sliding doors lead to a generous, fully fenced backyard with room to add a pool — perfect for families and a future value-add for investors. The show-stopping kitchen is designed to impress, featuring stainless steel appliances, a mosaic tile backsplash, white shaker cabinets, a large center island with sink, and a full pantry. Designer touches throughout — bold accent walls, custom pendant lighting, and wood-look tile flooring — give this home a distinctive, upscale feel that stands out in any market. The primary suite is a true retreat with a walk-in closet and a spa-inspired en-suite bath complete with a soaking tub, walk-in glass shower, dual-sink vanity, and elegant tile finishes. Two additional bedrooms offer flexibility for family, guests, or a home office. A stylishly updated second bath rounds out the interior. Outside, enjoy a covered patio and lush backyard — your own private piece of Florida paradise. The 2-car garage adds convenience and storage. Community amenities include exclusive access to Lake Rochelle for kayaking and water sports, scenic walking trails, private docks, and a playground — all with low HOA fees and absolutely NO CDD. Ideally located near US-27, major shopping, dining, medical centers, and Central Florida's top destinations including LEGOLAND®, Walt Disney World®, and Universal Studios®. This is a limited opportunity — priced to sell and incentives won't last long. Call today to schedule your private showing!
Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)
Listing Agent: Julio Salgado (407-791-0265)
732 7TH ST NE, WINTER HAVEN, FL 33881
$79,900129 Days on yellowkey MLS ID: L4958841
0 Days Off yellowkey (back on 2/12/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1528 Built: 1925 Tax: $417 (2025)Community: Martha HeightsSingle Family
Taxes:$417
Remarks: Estate-owned property being sold AS-IS for investor value. Seller inherited the home and has never occupied the property. Property requires significant renovation and is cash offers only; may not qualify for traditional financing. Seller will make no repairs or concessions. Buyer to perform all inspections and due diligence prior to closing.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Kevin Tison (863-206-5755)
4132 SPRUCEWOOD ST, WINTER HAVEN, FL 33880
$129,00011 Days on yellowkey MLS ID: P4938951
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1981Monthly Fee: $163 Tax: $1,183 (2025)Community: Oakwood EstatesManufactured Home
Taxes:$1,183
Remarks: Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the lanai as you enter the home. Once inside the home you will find a cozy family room and an open and and appealing kitchen just perfect for entertaining. The living room beyond the kitchen is open and spacious. The refrigerator was new in 2025. The guest bedroom opens onto the guest bath giving your overnight guest their own bathroom. The primary bedroom is large enough for a king sized bed, plus lots of closet storage space. The laundry with new washer and dryer is located inside the home. The roof was done in 2019 and the air conditioner in 2024. And if that isn't enough, there is new carpet throughout the home. Oakwood Estates is a 55+ community offering many activities and amenities. You can stay as busy as you would like, or just sit back and watch the world go by.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Kathy Devor (573-450-1679)
4612 REYNOSA DR SW, WINTER HAVEN, FL 33880
$310,000314 Days on yellowkey MLS ID: V4944212
1 Days Off yellowkey (back on 6/7/2026)
REDUCED by $10,000 (3.1%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1716 Built: 1984 Tax: $4,573 (2024)Community: Plaza SubSingle Family
Taxes:$4,573
Elementary School: Lake Shipp Elem
Middle School: Westwood Middle
Remarks: Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Trent Shackelford (941-518-7875)
814 SUNSET COVE DR, WINTER HAVEN, FL 33880
$305,00011 Days on yellowkey MLS ID: GC540983
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1768 Built: 2002Monthly Fee: $25 Tax: $3,730 (2025)Community: Sunset Cove Ph 01Single Family
Taxes:$3,730
Remarks: Welcome to 814 Sunset Cove Drive in Winter Haven! This move-in ready 4-bedroom, 2-bathroom home offers the perfect combination of comfort, style, and convenience. Nestled in a wonderful neighborhood, this well-maintained property features a spacious and functional floor plan designed for both everyday living and entertaining. Step outside to your own private retreat and enjoy the beautiful pool area, perfect for relaxing on sunny Florida days, hosting family gatherings, or creating lasting memories with friends. The backyard provides an inviting outdoor space to enjoy year-round. Inside, you’ll find generously sized bedrooms, comfortable living spaces, and a layout that makes you feel at home the moment you walk through the door. Whether you’re looking for your first home, a place to grow, or simply a move-in ready property with an exceptional outdoor living area, this home checks all the boxes. Don’t miss the opportunity to make this beautiful Winter Haven home your own!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ricky Catanzano, Jr (352-359-8991)
301 TERRANOVA BLVD, WINTER HAVEN, FL 33884
$415,00011 Days on yellowkey MLS ID: S5151390
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 2005Monthly Fee: $50 Tax: $4,429 (2025)Community: Terranova Ph 04Single Family
Taxes:$4,429
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bathroom home located in the desirable gated community of Terranova in Winter Haven. Offering approximately 1,960 square feet of living space, this residence features an open and functional floor plan designed for comfortable everyday living and entertaining. The spacious kitchen flows seamlessly into the main living areas, creating the perfect gathering space for family and friends. The primary suite provides a private retreat, while the screened lanai with a private spa offers the ideal place to relax and enjoy Florida living year-round. The beautifully landscaped backyard provides additional outdoor space for entertaining or unwinding. Conveniently located just 5 minutes from LEGOLAND Florida Resort and close to shopping, dining, hospitals, schools, and major roadways, this home offers the perfect combination of comfort, convenience, and location. The property is equipped with leased solar panels, which will be transferred to the buyer at closing, subject to the solar company's approval and transfer requirements. Schedule your private showing today and discover everything this exceptional home has
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Rosa Nieves (407-870-3125)
204 AVENUE D NE, WINTER HAVEN, FL 33881
$265,00011 Days on yellowkey MLS ID: O6413665
Bed: 6 Bath: 3.0 Liv Area Sq Ft: 2102 Built: 1915 Tax: $1,902 (2025)Community: Winter Haven HeightsSingle Family
Taxes:$1,902
Remarks: Prime mixed-use redevelopment opportunity in one of Winter Haven’s most strategic growth corridors. Situated directly across from Winter Haven Hospital, this property offers exceptional potential for investors, builders, and developers seeking to capitalize on a location positioned for long-term growth and redevelopment. The property is located within a Mixed-Use (MU) district that allows up to four residential dwelling units per lot and building heights of up to four stories, creating significant flexibility for residential, mixed-use, or income-producing projects. Its highly desirable location near major employment centers, medical services, retail, dining, and downtown Winter Haven further enhances its development appeal. An exceptional opportunity exists to assemble a larger development footprint through the acquisition of the adjacent parcel at 203 Ave C NE (see separate MLS#O6414107), as well as 209 Ave C NE (coming soon), offering the potential for a multi-parcel redevelopment project in a high-demand area. Opportunities of this scale and location are increasingly rare in Winter Haven. Whether acquired individually or as part of a larger assemblage, this property presents a compelling investment opportunity for developers seeking density, flexibility, and a premier location directly across from one of the area’s largest healthcare campuses.
Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)
Listing Agent: Paola Arias (407-969-9211)
1280 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$1,259,00014 Days on yellowkey MLS ID: L4961525
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5416 Built: 1995 Tax: $7,019 (2025)Community: N/ASingle Family
Taxes:$7,019
Remarks: Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come together in this truly one-of-a-kind estate on the shores of Lake Hamilton. Situated on more than one acre of fully fenced waterfront property with a wrought-iron gated entrance and no HOA restrictions, this custom residence offers over 5,400 square feet of living area designed for both grand entertaining and everyday enjoyment of Florida's lakefront lifestyle. From the moment you arrive, the home's distinctive architectural design makes a lasting impression. A circular driveway leads to the large covered portico where a tranquil fountain welcomes guests and creates an unforgettable arrival experience. Stepping through the double doors reveals a dramatic foyer with soaring ceilings, abundant natural light, and immediate panoramic lake views. Throughout the home, artistic influence and personality are evident at every turn. One of the owners is an accomplished artist, and their creativity is beautifully reflected in the home's unique design elements, decor, and inviting spaces. The completely remodeled kitchen, updated in 2018, serves as the heart of the home and features extensive custom cabinetry, granite countertops, a striking raised glass breakfast bar, center island with a built-in wine trough, and a bright eat-in dining area overlooking the lake. Nearby, the formal dining room provides the perfect initimate setting for holiday gatherings and special occasions. Designed with flexibility in mind, the home offers multiple living and entertaining spaces including a spacious family room anchored by a fireplace, dedicated office, theater room, enclosed Florida room stretching across the rear of the home, and numerous areas for relaxation or hosting guests. The expansive Florida room is the ideal place to begin each day with coffee while watching spectacular sunrises paint the sky over the water. The first floor features three generously sized guest bedrooms, while the private owner's retreat occupies the upper level. This luxurious sanctuary enjoys elevated wraparound views of Lake Hamilton, creating a peaceful escape unlike anything else in the area. Also located above is a unique artist's perch or widow's walk, offering an elevated vantage point to enjoy panoramic views, morning and evening skies, wildlife watching, and endless inspiration. Outdoor living is equally impressive. The heated salt-filtered pool, completed in 2018, overlooks the lake and creates a resort-style atmosphere. Expansive paver decking and wide-open lawn areas provide ample room for family gatherings, pets, and outdoor recreation. A composite dock extends into Lake Hamilton, making it easy to enjoy boating, fishing, paddleboarding, and sunset cruises. Spanning nearly 1,900 acres, Lake Hamilton is widely known for its excellent fishing, boating opportunities, and scenic beauty. Cruise across the lake to enjoy dining and entertainment at local favorites such as Floridino's and Port 27 before returning home for a peaceful sunset ride across the water. Additional features include a detached two-car garage, large storage shed and the privacy and freedom that comes with having no HOA. Rarely does a property combine architectural character, artistic expression, expansive living space, resort-style amenities, and over an acre of lakefront land in such a remarkable setting. This is more than a home—it is a private waterfront retreat where every sunrise feels like a work of art.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
206 DILLON ST, WINTER HAVEN, FL 33880
$215,00025 Days on yellowkey MLS ID: L4962158
0 Days Off yellowkey (back on 6/6/2026)
REDUCED by $2,000 (0.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1017 Built: 1996 Tax: $1,600 (2025)Community: Jan Phyl VillageSingle Family
Taxes:$1,600
Elementary School: Pinewood Elem
Remarks: Under contract-accepting backup offers. 3 bedroom, 2 bathroom concrete block home with a 1-car garage situated on a corner lot in the Jan Phyl Village area of Winter Haven with NO HOA. Several major updates were completed in 2021 including the roof, kitchen, flooring, guest bathroom flooring, and hot water heater. The home also features a newer dishwasher and new garage door. The backyard provides a great space for relaxing or entertaining. Conveniently located near Polk Parkway access, shopping, dining, schools, and surrounding Central Florida areas for an easier commute. Located in an established neighborhood with friendly neighbors and just a short distance from Winter Haven’s Chain of Lakes area. A solid option for a primary residence or investment property at an affordable price point.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Aubrie Flint (863-618-6347)
47 ENCLAVE DR, WINTER HAVEN, FL 33884
$245,000112 Days on yellowkey MLS ID: P4937867
REDUCED by $15,000 (5.8%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 1999Monthly Fee: $433 Tax: $3,221 (2025)Community: Cypresswood Enclave Ph 2Spa: NoVilla
Taxes:$3,221
Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!
Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)
Listing Agent: David Shippey (863-521-4517)
800 WARE AVE NE, WINTER HAVEN, FL 33881
$242,99962 Days on yellowkey MLS ID: O6399008
REDUCED by $1,996 (0.8%) on 06/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1000 Built: 2023 Tax: $1,293 (2025)Community: Swan Lake EstatesSingle Family
Taxes:$1,293
Remarks: Welcome to 800 Ware Ave NE, Winter Haven, FL, TENANT OCCUPIED, a fantastic opportunity for both investors and future homeowners alike! This 3-bedroom, 2-bathroom home features a desirable open floorplan with durable laminate flooring throughout, creating a seamless and low-maintenance living space. Situated on a spacious corner lot, the property also offers a fully fenced yard, perfect for added privacy, pets, or outdoor enjoyment. EXCELLENT INVESTMENT opportunity with a reliable, good-paying tenant already in place through January 2027, providing immediate and consistent income. Enjoy the peace of country-style living while remaining just minutes from Winter Haven’s Chain of Lakes, as well as nearby shopping, dining, and world-famous Central Florida attractions like LEGOLAND, Disney, and Universal Studios. The home also includes a dedicated utility/laundry room and the benefits of a newer, energy-efficient build, making it truly move-in ready and built for long-term value. Don’t miss your chance to secure this income-producing property or future home, schedule your private tour today!
Listing Agent: Veronica Figueroa (407-519-3980)
271 INMAN BLVD, WINTER HAVEN, FL 33881
$350,000194 Days on yellowkey MLS ID: W7881213
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2274 Built: 2024Monthly Fee: $49 Tax: $1,347 (2024)Community: Inman GrovesSpa: NoSingle Family
Taxes:$1,347
Remarks: PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)
Listing Agent: Isabelle Maye (540-840-8849)
117 4th JPV ST, WINTER HAVEN, FL 33880
$190,000134 Days on yellowkey MLS ID: TB8472143
REDUCED by $28,000 (12.8%) on 05/29/2026
Bed: 3 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1224 Built: 1957 Tax: $2,572 (2025)Community: Jan Phyl Village Unit 02 Pb 37 Pg 50Single Family
Taxes:$2,572
Remarks: Under contract-accepting backup offers. Looking for the perfect starter home or turnkey investment? Welcome to 117 4th Ave N! This well-maintained 3-bedroom, 1.5-bath home has been lovingly cared for by the same family for over 40 years and is now ready for its next chapter. Situated just minutes from shopping and dining, this property delivers both comfort and convenience in the heart of Winter Haven. Recent updates include a brand-new roof (2025), providing peace of mind and long-term value. For investors, current tenants are interested in staying—offering an immediate income opportunity if desired. Inside, you'll find an open and inviting floor plan where the kitchen flows seamlessly into the spacious living room. Each bedroom offers generous space with nice-sized closets, perfect for growing families or long-term renters. But here's the bonus: attached to the back of the home is additional flex space not included in the square footage. This area could easily be converted into a 4th bedroom, mother-in-law suite, home office, or studio—adding even more value and versatility to the property. Parking is another standout feature with a covered carport plus a detached garage—ideal for extra vehicles, storage, or workshop space. Priced to sell and brimming with potential, this gem won't last long.
Listing is courtesy of: FIVE STAR REAL ESTATE OF FLORIDA LLC (904-539-3336)
Listing Agent: Arina Reid-Martin (770-500-0514)
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