Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881
$120,00028 Days on yellowkey MLS ID: L4960788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1252 Built: 1985Monthly Fee: $325 Tax: $1,415 (2025)Community: Country Lake CondoSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,415
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
6236 KNOTTY PINE DR SE, WINTER HAVEN, FL 33884
$145,000115 Days on yellowkey MLS ID: L4958273
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1369 Built: 2000Monthly Fee: $65 Tax: $2,744 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$2,744
Elementary School: Garden Grove Elem
Remarks: Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area ideal for relaxing or entertaining. The kitchen provides ample storage and prep space, while the adjoining dining area creates a natural flow for everyday living. Outside, you’ll enjoy a low-maintenance yard, covered parking, and plenty of room for outdoor seating. Garden Grove Oaks residents love the clubhouse, community pool & hot tub, social activities, and peaceful setting, all while being close to shopping, dining, medical facilities, and the best of Winter Haven. Whether you’re seeking a seasonal retreat or a year-round home, this charming property is move-in ready and waiting for you!
Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)
Listing Agent: Nicole Castro (863-547-5647)
207 24TH CT SW, WINTER HAVEN, FL 33880
$285,000104 Days on yellowkey MLS ID: L4958315
1 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1296 Built: 1976 Tax: $4,614 (2025)Community: West Of Lake HowardSingle Family
Taxes:$4,614
Elementary School: Inwood Elem
Middle School: Westwood Middle
Remarks: Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the heart of Winter Haven. Offering nearly 1,300 square feet of comfortable living space, this well-maintained home features a functional layout with a kitchen and family room combination, ceiling fans throughout, and plenty of natural light. Step outside to your private backyard oasis complete with an in-ground pool—perfect for relaxing, entertaining, or enjoying Florida’s sunshine year-round. A one-car garage adds convenience, while the absence of HOA fees provides flexibility and freedom. Ideally located near schools, shopping, dining, and major roadways, this home is a wonderful opportunity for homeowners or investors alike. NEW ROOF 2020, NEW AC 2022. Don’t miss your chance to make this inviting Winter Haven property your own!
Listing Agent: Melissa Mottern (863-860-1808)
100 EL CAMINO DR #101, WINTER HAVEN, FL 33884
$109,99028 Days on yellowkey MLS ID: S5147114
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1971 Tax: $393 (2025)Community: Orchid SpringsSpa: NoCondo
Taxes:$393
Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Sharon Gastelbondo (863-800-4655)
100 EL CAMINO DR #111, WINTER HAVEN, FL 33884
$71,000115 Days on yellowkey MLS ID: S5141094
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 931 Built: 1971 Tax: $1,178 (2025)Community: GranadaSpa: NoCondo
Taxes:$1,178
Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.
390 16TH ST NE, WINTER HAVEN, FL 33881
$238,90071 Days on yellowkey MLS ID: P4937879
REDUCED by $1,000 (0.4%) on 04/07/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2178 Built: 1959 Tax: $3,631 (2025)Community: Lake Elbert Heights Unit 02 02 RepSingle Family
Taxes:$3,631
Remarks: The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming atmosphere, while multiple living areas provide room to spread out and enjoy. The remodeled kitchen features a refrigerator, dishwasher, and range, along with a convenient breakfast bar and adjacent dining area—perfect for everyday living and entertaining. A formal living room greets you at the front entry, and the oversized family room offers exceptional gathering space, complete with a built-in desk and direct access to the screened lanai. The generous primary suite includes a walk-in closet, garden tub, separate shower, and an additional wall A/C unit for added comfort. A desirable mini–master suite with its own private bath provides ideal space for guests, extended family, or a private home office. Built-in cabinetry throughout the home adds both character and abundant storage. Situated on a large corner lot, the expansive yard offers endless possibilities for outdoor living, recreation, or future enhancements. The chain-link fenced backyard provides security and functionality while maintaining an open feel. With no HOA restrictions, you’ll enjoy the freedom to personalize the property to suit your needs. Combining space, natural light, a sizable yard, and the advantage of no HOA, this property delivers comfort, flexibility, and room to grow.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Michelle Heath (863-528-3123)
310 17TH ST NE, WINTER HAVEN, FL 33881
$300,00090 Days on yellowkey MLS ID: L4958640
0 Days Off yellowkey (back on 4/7/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1796 Built: 1958 Tax: $2,575 (2025)Community: Lake Elbert Heights Unit 2 2Nd ReplatSingle Family
Taxes:$2,575
Remarks: Under contract-accepting backup offers. Enclosed Saltwater Pool | Corner Lot | 4 Bedrooms in Winter Haven Welcome to 310 17th St NE in Winter Haven, FL — a charming 4-bedroom, 2.5-bath pool home set on a spacious 0.28-acre corner lot in an established neighborhood. This home offers a blend of character, space, and opportunity for the next owner. Inside, you'll find nearly 1,800 sq ft of living space with a functional layout that includes four bedrooms, 2 full bathrooms and a convenient half bath, offering flexibility for guests, home office space, or everyday living. The kitchen and bathrooms retain their original style, giving buyers the chance to update and personalize over time. Step outside and enjoy the enclosed saltwater pool (installed in 2018), creating a private outdoor space for relaxing or gathering with friends. The fenced backyard and large corner lot provide room to spread out and enjoy outdoor living. Major systems have already been updated, including AC (2020) and water heater (2018). The home also offers 2,267 total square feet under roof, adding additional usable space. Conveniently located near shopping, dining, schools, and major roadways, this property combines the charm of an established Winter Haven neighborhood with everyday convenience.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Jenelle Grabowicz (863-604-0834)
1012 MEDINAH DR SE, WINTER HAVEN, FL 33884
$187,900245 Days on yellowkey MLS ID: P4936101
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1981Monthly Fee: $320 Tax: $2,740 (2025)Community: CypresswoodSpa: NoVilla
Taxes:$2,740
Remarks: Fresh new price — NOW OFFERING A HOME WARRANTY! Your opportunity to own in Cypresswood just got better! Welcome to The Tennis Villas! Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a welcoming first impression and a charming space to enjoy.This 2-bedroom, 2-bath villa features expansive living and dining areas with laminate flooring, a bright kitchen with updates and ceramic tile flooring. An open-concept layout that includes a wet bar with cabinet storage—perfect for entertaining. A bonus Florida room with air conditioning overlooks an open field and pond, providing a peaceful view right from your home.The primary bedroom boasts a sliding glass door leading to the enclosed lanai, filling the space with natural light and offering relaxing backyard views. Recent updates include a NEW metal roof for peace of mind. Plus, the HOA covers exterior paint, roof maintenance, lawn care, and pest control, making this home truly move-in-ready.The Cypresswood community offers incredible amenities:An 18-hole championship golf course designed by Ron Garl, Junior Olympic-sized pool, Lighted tennis courts, Fitness center & clubhouse with pro-shop, On-site restaurant and event space.Whether walking, biking, or taking the golf cart, all amenities are conveniently close by. You’ll also love the location—just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, and plenty of shopping and dining options.Don’t miss your chance to enjoy the Florida country club lifestyle in this affordable, stylish villa. Schedule your private showing today!
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
356 STERLING DR, WINTER HAVEN, FL 33884
$332,00062 Days on yellowkey MLS ID: L4959652
0 Days Off yellowkey (back on 4/6/2026)
REDUCED by $3,000 (0.9%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1535 Built: 2001Monthly Fee: $24 Tax: $3,462 (2025)Community: BerryhillSingle Family
Taxes:$3,462
Remarks: Clean, clean, clean. Welcome to 356 Sterling Drive — a meticulously maintained 3-bedroom, 2-bath pool home that truly shows like a model. Pride of ownership is evident from the moment you arrive, where outstanding curb appeal showcases fresh exterior paint, hurricane-rated double-pane windows and sliding doors, lush landscaping, and a welcoming front lawn. This move-in ready residence offers extensive recent updates, including a brand-new roof with Heritage Proline Titan XT shingles (2025), refinished pool, new stainless steel appliances (2023), water heater (2023), new double-hung hurricane rate double pane windows (2024), updated bathroom vanities, new interior and exterior paint (2023), upgraded door hardware and electrical faceplates (2023), and more. Inside, an open and airy layout features tile flooring throughout, elevated ceilings, and an inviting great room designed for both relaxed living and entertaining while capturing tranquil views of the screened pool. The eat-in kitchen provides generous workspace, ample cabinetry, newer stainless appliances, and a charming bay-window dinette ideal for everyday dining. A desirable split bedroom plan ensures privacy. The spacious primary suite offers generous closet space and a well-appointed en-suite bath with dual sinks, updated finishes, and a tiled walk-in shower. Secondary bedrooms are nicely sized and provide convenient access to the full guest bath. Outdoor living is where this home truly shines. The screened pool and fully fenced backyard create the perfect setting for enjoying Florida’s year-round lifestyle, offering privacy, space for pets or play, and fruit trees that add beauty and a touch of nature. A two-car garage provides additional storage and everyday convenience. Located in the established Berryhill community of southeast Winter Haven, the home offers convenient access to shopping, dining, schools, medical facilities, and everyday essentials. Winter Haven’s central location between Tampa and Orlando makes commuting and travel easy while still enjoying the relaxed lifestyle the area is known for — including the Chain of Lakes, boating, recreation, and a vibrant community atmosphere. A beautifully updated home, thoughtfully cared for, and ready for its next chapter.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
1733 SANDALWOOD CIR SW, WINTER HAVEN, FL 33880
$260,00090 Days on yellowkey MLS ID: L4958444
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1075 Built: 1984 Tax: $1,330 (2025)Community: Sandalwood SubSingle Family
Taxes:$1,330
Elementary School: Lake Shipp Elem
Remarks: Attention Investors & Homeowners! Whether you’re a seasoned investor or looking for a home with built-in income, this property presents an exciting opportunity. This well-maintained 3-bedroom, 2-bath block home is located within Winter Haven city limits and offers 1,155 square feet of tile flooring throughout with no HOA. The home features a functional layout, spacious rooms, ample kitchen counter space, and a large fenced backyard. Major updates include a newer roof (2018), A/C replacement (2014), and a water heater installed in 2004. Currently tenant-occupied, making it a great income-producing option with future flexibility. Conveniently located just minutes from shopping, downtown Winter Haven, and approximately 12 minutes from LEGOLAND. Don’t miss out—schedule your showing today and see the potential for yourself.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Melissa Ramirez (813-956-1071)
610 GROVE ST, WINTER HAVEN, FL 33881
$271,000120 Days on yellowkey MLS ID: L4957731
REDUCED by $14,000 (4.9%) on 04/06/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1867 Built: 2022Monthly Fee: $50 Tax: $4,897 (2024)Community: Inman Grvs Ph 2Single Family
Taxes:$4,897
Tax Year: 2024
Remarks: This 3 YEAR YOUNG, 4 bedroom, 2 bath single-family home built by DR Horton offers 1,867 square feet of thoughtfully designed living space and a 2-car ATTACHED GARAGE with OPENER and NO SOLAR PANELS!! The open floorplan features a seamless kitchen, dining area, and family room combination, ideal for both everyday living and entertaining. The kitchen includes a CENTER ISLAND, GRANITE countertops, DOUBLE SINK, and a WALK-IN PANTRY and is ready for your personal touch with NEEDED APPLIANCES (except for the included dishwasher). Ceramic tile flooring runs throughout the main living areas, with carpet in the bedrooms. The PRIMARY BEDROOM boasts a WALK-IN CLOSET and a spacious EN-SUITE BATHROOM featuring a walk-in SHOWER, DUAL SINKS with GRANITE countertops, and a PRIVATE WATER CLOSET. Three additional bedrooms are serviced by BATHROOM #2, which offers a TUB/SHOWER combination, SINGLE SINK VANITY, and GRANITE countertop. An INSIDE LAUNDRY ROOM with washer/dryer HOOK-UPS adds convenience. Additional features include an IRRIGATION SYSTEM and a COVERED concrete LANAI, accessed through sliding glass doors from the family room. This home combines modern design, functionality, and value in a well-built, nearly new property. NOTE: THIS PROPERTY IS NOT FOR RENT!!! DON'T BE SCAMMED BY SOMEONE ADVERTISING THE PROPERTY FOR RENT ON SOCIAL MEDIA!!
Listing is courtesy of: VIEWPOINT VALUE REALTY (863-617-7015)
Listing Agent: Pat Pearson (908-295-7970)
287 INMAN BLVD, WINTER HAVEN, FL 33881
$315,00027 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
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
$295,90027 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 Agent: Dave Westphal (863-287-3302)
411 AVENUE A SE, WINTER HAVEN, FL 33880
$215,000275 Days on yellowkey MLS ID: L4954810
0 Days Off yellowkey (back on 4/3/2026)
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)
260 GREENFIELD RD, WINTER HAVEN, FL 33884
$393,00079 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
$337,00064 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
$349,000315 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)
205 WESTWOOD AVE, WINTER HAVEN, FL 33880
$210,00048 Days on yellowkey MLS ID: TB8485945
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
$165,90084 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
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
$135,00087 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.