Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
260 GREENFIELD RD, WINTER HAVEN, FL 33884
$393,00073 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,885
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
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
$337,00058 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!
2800 SUNSET DR NW, WINTER HAVEN, FL 33881
$349,000309 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
Tax Year: 2024
Middle School: Westwood Middle
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)
205 WESTWOOD AVE, WINTER HAVEN, FL 33880
$210,00042 Days on yellowkey MLS ID: TB8485945
0 Days Off yellowkey (back on 4/3/2026)
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 806 Built: 2021 Tax: $2,703 (2025)Community: Brysons R H SubSingle Family
Taxes:$2,703
Elementary School: Frank E. Brigham Academy
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Charming 2-bedroom, 1.5-bath home located in Winter Haven presenting a great opportunity for first-time home buyers or investors. This property features a functional layout with comfortable living spaces and a practical design suited for everyday living. The home sits on a generously sized lot, providing plenty of outdoor space for entertaining, gardening, or future improvements. Conveniently located near local schools, shopping, dining, and major roadways, this property provides both accessibility and convenience. With strong potential as a starter home, rental property, or investment opportunity, this home is a great option for buyers looking to enter the market or expand their portfolio in the growing Winter Haven area.
Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)
Listing Agent: Jay Patel (863-399-5820)
1246 31ST ST NW, WINTER HAVEN, FL 33881
$165,90078 Days on yellowkey MLS ID: TB8470610
REDUCED by $4,000 (2.4%) on 04/02/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 840 Built: 1961 Tax: $1,157 (2024)Community: West Cannon HeightsSingle Family
Taxes:$1,157
Elementary School: Inwood Elem
Remarks: Welcome to this charming 2-bedroom, 1-bathroom home in the West Cannon Heights neighborhood of Winter Haven, an excellent opportunity for first-time buyers or investors. With a really large open kitchen, this home is move-in ready. The exterior features a covered parking area and a workshop with a new roof. This property offers a cozy living space and a convenient location, with no HOA fees. Don't miss the chance to own this piece of Winter Haven.
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Pablo Lluveras Matos (813-406-3652)
1550 11TH ST NE #D7, WINTER HAVEN, FL 33881
$135,00081 Days on yellowkey MLS ID: P4937703
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1976Monthly Fee: $361 Tax: $2,265 (2025)Community: Lake Buckeye CondomiCondo
Taxes:$2,265
Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: Carlee Marchetti (863-258-3338)
262 OLEANDER ST, WINTER HAVEN, FL 33881
$274,90045 Days on yellowkey MLS ID: TB8479025
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1743 Built: 2017Monthly Fee: $49 Tax: $2,428 (2025)Community: Lakes/Lucerne Park Ph 3Single Family
Taxes:$2,428
Elementary School: Lake Alfred Elem
Remarks: One or more photo(s) has been virtually staged. SUPER DEAL on a big four bedroom home! Clean, fresh and well maintained home! PLUS, an American Preferred Home Warranty is included! With American Home Warranty, if you ever need to use it, you get to choose your own preferred vendors! Enjoy room for the family and privacy for mom and dad in the spacious split bedroom layout . You are going to like the open-concept living areas, big island kitchen with walk-in kitchen pantry. The large master suite with ensuite bath has a large walk in closet. Plenty of natural light brightens your living spaces from the energy efficient windows. All bedrooms are generously sized. Style and comfort welcome you with brand new beautiful, premium style, extra thick, waterproof luxury vinyl plank flooring in all the living areas. Fresh new carpet in all bedrooms. Pretty ceramic tile in wet areas. ROOF 2024! A fresh coat of premium exterior paint has been done and seals the deal for years to come. MOVE IN READY! Come and see this lovely home in the well-maintained Lakes at Lucerne community today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Patty Wolfgang (813-389-5226)
2782 ADELINE AVE, WINTER HAVEN, FL 33881
$280,99037 Days on yellowkey MLS ID: O6391785
REDUCED by $10,000 (3.4%) on 04/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1328 Built: 2026Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Taxes:$3,456
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today!
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
2790 ADELINE AVE, WINTER HAVEN, FL 33881
$282,99037 Days on yellowkey MLS ID: O6391726
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. 2 Spare Bedrooms and an Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
2786 ADELINE AVE, WINTER HAVEN, FL 33881
$294,99037 Days on yellowkey MLS ID: O6391683
REDUCED by $10,000 (3.3%) on 04/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1498 Built: 2026Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Now let me Introduce you to the Freeport II this 1498 sqft, 4 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas and Great room and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and the laundry room also includes a Washer and Dryer. With 2 Spare Bedrooms in the Front one in the Middle and an Owners Suite in the Back. The Owners Suite can easily fit a King size bed and has a large Walk-in closet. It also includes a Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
204 INMAN BLVD, WINTER HAVEN, FL 33881
$369,900105 Days on yellowkey MLS ID: L4958414
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2022Monthly Fee: $49 Tax: $4,974 (2024)Community: Inman GrovesSingle Family
Taxes:$4,974
Remarks: New Price and $2500 Seller Credit!! Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking. Priced at $374,900—approximately $140 per square foot—this home delivers exceptional value compared to similar properties in California and many northern metro areas. The well-planned layout includes five true bedrooms, three full bathrooms, and a versatile flex space that could easily be converted into a sixth bedroom. This additional space makes the home ideal for growing families, multigenerational living, aging parents, young adults living at home, or a private home office or hobby room. A guest suite on the first floor adds even more functionality and convenience. The main living areas feature upgraded tile flooring, while the kitchen is finished with granite countertops and ample workspace for everyday living and entertaining. The home has been meticulously maintained and is in pristine, move-in-ready condition. Outdoors, enjoy added privacy with no rear neighbors, creating a peaceful and open backdrop rarely found in newer communities. Located just 5 minutes from downtown Winter Haven, residents enjoy easy access to historic charm, the Ritz Theatre, Saturday farmers markets, a beautiful public library, and a growing selection of high-end and locally owned dining options. A brand-new Publix grocery store is currently under construction within walking distance, adding everyday convenience and long-term appeal. The community features a very low HOA and no CDD fees, helping keep ownership costs manageable—an important advantage for relocating buyers. Ideally positioned just 5 minutes from Legoland Florida and approximately 30 minutes from Disney, the home offers access to Central Florida attractions while maintaining a comfortable residential setting. With generous square footage, flexible living spaces, privacy, and proximity to downtown amenities, this home is an outstanding opportunity for buyers ready to trade cold winters or high housing costs for a more flexible and comfortable Florida lifestyle.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Veronica Bard (863-670-7526)
4094 GREAT EGRET DR, WINTER HAVEN, FL 33881
$305,000233 Days on yellowkey MLS ID: S5133843
1 Days Off yellowkey (back on 3/9/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 2019Monthly Fee: $12 Tax: $4,235 (2024)Community: Lakeside Lndgs Ph 3Single Family
Taxes:$4,235
Middle School: Davenport School of the Arts
Remarks: Under contract-accepting backup offers. Step into a home where every space invites you to stay and every corner is designed to create beautiful memories. This stunning, well-cared-for 4-bedroom, 2-bath single-family home is located in a quiet and peaceful area of Winter Haven, Florida, offering the perfect balance of comfort, warmth, and everyday tranquility. From the very first moment, this home welcomes you with an open, light-filled layout that brings the living and dining areas together—ideal for laughter-filled gatherings, special celebrations, and cozy nights at home. This is where life happens. At the heart of the home, the modern kitchen stands out with a spacious center island and drop-in sink, creating the perfect setting to cook, connect, and share unforgettable moments with family and friends. Just beyond, the screened porch becomes your personal retreat—perfect for morning coffee, evening conversations, or simply unwinding as the day fades away. The primary suite is a true private escape, offering space, comfort, and serenity. Enjoy an elegant ensuite bathroom with an oversized shower and a generous walk-in closet designed to make daily living effortless and enjoyable. Thoughtfully designed extras—including an indoor laundry room, a two-car garage, and a 6-speaker sound system throughout the home—add comfort, convenience, and the perfect atmosphere for every occasion. Located less than 13 minutes from downtown Winter Haven, you’re close to everything you need—shopping, dining, schools, and services—while still enjoying the peace of a calm, welcoming neighborhood.
Listing is courtesy of: PRESTIGE LEGACY REALTY (407-760-1521)
Listing Agent: Gil Medina (407-760-1521)
196 DURRELL CIR, WINTER HAVEN, FL 33884
$215,00025 Days on yellowkey MLS ID: O6393488
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 1973 Tax: $3,359 (2025)Community: Fla Highlands Co SubSingle Family
Taxes:$3,359
Elementary School: Garden Grove Elem
Remarks: This 3-bedroom, 2-bathroom home located in the Florida Highland Co neighborhood. This residence offers a classic and straightforward layout that provides a comfortable living environment for a variety of lifestyles. The heart of the home features a kitchen equipped with a mix of black and white appliances, complemented by durable laminate countertops that offer plenty of workspace for daily meal preparation. The interior transitions smoothly between living areas, maintaining a functional sense of space throughout. Situated in a convenient location, this property offers easy access to local amenities and major regional hubs, ensuring a simplified commute for those working in the surrounding areas. Schedule your private showing today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
235 6TH ST NW #307, WINTER HAVEN, FL 33881
$125,000171 Days on yellowkey MLS ID: P4936842
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 714 Built: 1982 Tax: $1,976 (2025)Community: The HavenCondo
Taxes:$1,976
Elementary School: Lake Shipp Elem
Remarks: One or more photo(s) has been virtually staged. Downtown Winter Haven condo located in one of Winter Haven’s most iconic hotels, The Haven. This residence has been transformed into boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. With its blend of vintage charm, modern updates, and low-maintenance living, this 1-bedroom, 1-bath unit is ideal for first-time buyers, investors, seasonal residents, or anyone seeking an affordable condo with great rental potential. Located on the 3rd floor, the residence features tall ceilings, large windows, and bright natural light with elevated views of downtown. The updated kitchen offers granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets—perfect for maximizing storage in a condo setting. The spacious primary bedroom boasts oversized historic windows, a walk-in closet, and room for a king-sized bed. The bathroom has been refreshed with granite counters, a tiled tub surround, and a traditional tub/shower combo. The Haven provides sought-after condo amenities, including secure key-fob access, elevators, a community pool, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby. Residents also enjoy a private pool courtyard surrounded by lush landscaping, creeping fig walls, palm trees, and peaceful lounging areas—ideal for relaxation or working remotely outdoors. This walkable location offers the best of downtown Winter Haven living. Enjoy immediate access to dining, shopping, entertainment, and lakefront walking paths. With 50 lakes—including the world-famous Winter Haven Chain of Lakes—you’re minutes from boating, fishing, skiing, and sunset views. Everyday conveniences like Publix, Walmart, Aldi, TJ Maxx, medical facilities, and LEGOLAND Florida Resort are all close by. If you’re looking for an affordable, updated, low-maintenance condo with historic character and the convenience of downtown living, this stylish unit at The Haven checks every box.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
4622 CYPRESS GARDENS RD, WINTER HAVEN, FL 33884
$180,00027 Days on yellowkey MLS ID: S5146684
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1706 Built: 1985 Tax: $3,238 (2025)Community: Silver Oaks VillasSingle Family
Taxes:$3,238
Remarks: Welcome to this charming and versatile 2-bedroom, 2-bath home offering 1,706 square feet of living space in Winter Haven. This property features a spacious combined living and dining area, ideal for both everyday living and entertaining. The home also offers a flexible bonus room that can easily be converted into a third bedroom, home office, hobby space, or guest area, along with a bright sunroom at the back—ideal for relaxing and enjoying backyard views year-round. Step outside to a screened-in back porch, ideal for unwinding or outdoor dining, and take advantage of the backyard shed for additional storage. With its adaptable spaces and inviting indoor-outdoor features, this home is a must-see—schedule your private showing today and discover all it has to offer! The home is being Sold in As Is condition without any Warranty nor Guarantee by seller. The buyer is responsible for verifying ALL property information, room sizes, utilities and condition. All buyers must view the home before submitting an offer. HUD CASE: 098-116683 FINANCE ESCROW MAY APPLY FINANCE CODE: IE
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
4913 JACKSON ST, WINTER HAVEN, FL 33884
$239,90096 Days on yellowkey MLS ID: O6374521
2 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 2023Monthly Fee: $67 Tax: $3,152 (2025)Community: Jackson LndgSingle Family
Taxes:$3,152
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.
Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)
Listing Agent: Wanda Turner (407-756-2194)
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$434,900121 Days on yellowkey MLS ID: L4958092
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Single Family
Taxes:$2,790
Tax Year: 2023
Remarks: *** Motivated seller! Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! *** Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Brian Surrency (863-204-4298)
1620 KLATT ST SE, WINTER HAVEN, FL 33880
$199,90035 Days on yellowkey MLS ID: L4960372
0 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1087 Built: 1959 Tax: $1,885 (2025)Community: Shamrock ResubSingle Family
Taxes:$1,885
Elementary School: Chain O Lakes Elem
Remarks: Under contract-accepting backup offers. Welcome to 1622 Klatt St SE in Winter Haven, a unique opportunity offering business residential zoning ideal for homeowners, investors, or small business use. This property provides flexibility for residential living, home office, rental income, or professional services in a growing and centrally located area. Situated on high and dry land, this property offers added peace of mind with no flood concerns. The lot and location make it well-suited for long-term ownership, redevelopment, or income-producing potential. Conveniently located near major roadways, shopping, dining, and local amenities, this property benefits from strong accessibility and visibility while still maintaining a residential feel. The surrounding area continues to see growth, making this an attractive option for buyers looking to secure property in a developing corridor. This property is priced appropriately for today’s market, creating an excellent opportunity for buyers seeking value, flexibility, and location in Winter Haven.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
4454 GLENNS LNDG, WINTER HAVEN, FL 33884
$259,00053 Days on yellowkey MLS ID: P4938011
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1526 Built: 1991Monthly Fee: $83 Tax: $2,292 (2025)Community: Cypress Landing Ph 03Single Family
Taxes:$2,292
Remarks: One or more photo(s) has been virtually staged. This beautifully maintained 2-bedroom, 2-bath home with a 2-car garage offers the perfect blend of comfort, smart updates, and lifestyle perks. There’s something about 4454 Glenns Landing that feels like home before you even step inside. Maybe it’s the quiet charm of the neighborhood — families out walking at sunset, riding bikes, neighbors waving as they pass. Maybe it’s knowing you’re not just buying a house…you’re stepping into a true community. Inside, enjoy the natural light through new windows installed in 2021 and the roof was also replaced in 2020, giving you peace of mind and eliminating two major expenses right from the start. The kitchen has a quaint eat-in area as well as great counter space for food prep and stainless steel appliances. The seamless flow between the living room and dining area creates a spacious feel while keeping everything connected — perfect for entertaining guests, hosting family dinners, or simply enjoying a cozy night at home. The primary suite is a relaxing retreat, featuring a spacious walk-in closet and a private bath with solid surface countertops that add both durability and elegance. The secondary bathroom also showcases matching solid surface countertops, creating a cohesive and polished feel throughout. One of the home’s best surprises, the fully enclosed porch with its own air vent, seamlessly adding extra square footage of living space. Whether you envision a sunroom, home office, reading nook, or second living area, this flexible space gives you room to live the way you want. Step outside your front door and enjoy a neighborhood designed for connection. Residents enjoy access to: a clubhouse with a sparkling pool, a fishing pier and dock, boat slips available on a first-come, first-serve basis, a vibrant social club that plans activities year-round.
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Tisha Talbot (863-236-7610)
29 GOLF VIEW CIR NE, WINTER HAVEN, FL 33881
$300,000141 Days on yellowkey MLS ID: TB8453876
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1962 Tax: $4,496 (2024)Community: North Lake Elbert HeightsSingle Family
Taxes:$4,496
Remarks: Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Chris Sakamoto (904-200-7535)
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