Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Beds: 3 to 3
Do Not Show Listings
Winter Haven - 324 properties found
312 TOWHEE RD, WINTER HAVEN, FL 33881
$339,000153 Days on yellowkey MLS ID: B4902119
REDUCED by $10,000 (2.9%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2020 Built: 2005Monthly Fee: $34 Tax: $2,621 (2024)Community: Hamilton West Ph 01Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,621
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: ? Back on Market – New Price Welcome to this move-in ready 4-bedroom, 2-bath home with a 2-car garage, perfectly situated on a rare nearly ½-acre oversized lot in Winter Haven! This home offers the space and updates today’s buyers are looking for — including a brand NEW roof and NEW A/C (2025), giving peace of mind and added value from day one. Step inside to a bright, open layout with updated flooring and plenty of room for both everyday living and entertaining. The spacious kitchen flows seamlessly into the main living area, creating a comfortable and inviting atmosphere. The flexible 4th bedroom with French doors can easily serve as a guest room, home office, or additional living space — tailored to your needs. Outside, the oversized lot is a true standout! Whether you’re dreaming of adding a pool, storing a boat or RV, or creating your own backyard oasis, this property gives you the space to make Conveniently located near shopping, dining, and major roadways while still offering room to spread out — a rare combination at this price point. Don’t miss your chance to own a home with space, updates, and flexibility — schedule your showing today! The listing agent is an owner of the property
Listing is courtesy of: FREEDOM REALTY (863-289-7004)
Listing Agent: Ike Fountain (863-206-1105)
542 EAGLE LANDING BOULEVARD, WINTER HAVEN, FL 33880
$290,00028 Days on yellowkey MLS ID: L4960889
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1292 Built: 2021Monthly Fee: $38 Tax: $3,061 (2025)Community: Eagle Landing Phase ISingle Family
Taxes:$3,061
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Carla Miro (786-897-4081)
1516 AVENUE D NE, WINTER HAVEN, FL 33881
$286,000152 Days on yellowkey MLS ID: O6364664
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1970 Tax: $2,486 (2024)Community: Lake Elbert HeightsSingle Family
Taxes:$2,486
Remarks: Fully renovated 3BR/2BA home with an open space perfect for office or extra space located in Winter Haven NO HOA! New Roof, New AC, New Water Heater, New Flooring, New Kitchen Cabinets, updated bathrooms cabinets, and modern finishes throughout. Turn-key and move-in ready with a spacious yard and great location. Huge fenced backyard with banana trees Plus, NO HOA — enjoy more freedom and lower monthly costs Don’t miss it!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Karina Turcios (407-346-7606)
878 KILLEARN BLVD, WINTER HAVEN, FL 33880
$255,00094 Days on yellowkey MLS ID: O6377826
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1467 Built: 1983 Tax: $3,710 (2025)Community: Cinnamon Ridge Ph 03Spa: NoSingle Family
Taxes:$3,710
Elementary School: Lake Shipp Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: BACK ON THE MARKET! PRICE CHANGE – NO HOA & PRICED TO SELL! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat. Inside, you’ll find a functional, comfortable layout with great natural light and flexible living space. This home presents an excellent opportunity for buyers looking to add personal style, build equity, or secure a solid investment property in a growing area. Whether you’re a first-time buyer, downsizing, or expanding your investment portfolio, this home offers strong potential, location convenience, and everyday livability. Ideally located near shopping, dining, Downtown Winter Haven, and the Polk Parkway, with easy access to both Orlando and Tampa for commuting or weekend travel. If you’re looking for space, flexibility, and long-term value with NO HOA restrictions, this is one you don’t want to miss. Schedule your private showing today and explore the possibilities.
Listing is courtesy of: SIGNATURE INTERNATIONAL REAL E (561-404-7263)
Listing Agent: Barbi Rodriguez, Llc (352-404-2377)
107 SUGAR CREEK RD, WINTER HAVEN, FL 33880
$349,9004 Days on yellowkey MLS ID: P4938569
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1511 Built: 1985 Tax: $1,380 (2025)Community: Not In SubdivisionSingle Family
Taxes:$1,380
Remarks: BEAUTIFUL 3-BEDROOM POOL HOME ~ This inviting residence offers the perfect blend of comfort and functionality, featuring a spacious living room ideal for relaxing or entertaining, expansive kitchen, along with a desirable layout for added privacy. The home includes 3 bedrooms and 2 bathrooms, with a unique primary suite setup that features a private sink area separate from the bathroom for added convenience. Step outside to enjoy a screened-in lanai with a 10,000-gallon in-ground pool, perfect for soaking up the Florida lifestyle year-round. The patio provides additional outdoor space for dining or lounging, while the fully fenced backyard showcases mature landscaping for both beauty and privacy, along with a handy storage shed. This well-maintained property is move-in ready and offers everything you need to enjoy indoor-outdoor living at its finest—schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Erin Floyd (863-412-2286)
1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880
$795,00017 Days on yellowkey MLS ID: L4961193
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2001 Built: 2021 Tax: $7,094 (2025)Community: N/ASingle Family
Taxes:$7,094
Remarks: Welcome to true lakefront living on the renowned Chain of Lakes in Winter Haven, perfectly positioned on Lake Shipp with approximately 500 feet of waterfrontage, an extremely rare offering that creates the feel of your own private park right in your backyard. Built in 2021 with block-on-slab construction and a durable metal roof, this 3-bedroom, 3-bathroom home was designed to maximize water views and effortless indoor-outdoor living. Inside, you’ll find soaring ceilings and an open layout that flows seamlessly into the kitchen, featuring 42-inch cabinetry, quartz countertops, a large island, pantry, and a dine-in area—ideal for entertaining or everyday living. Large 8-foot sliding glass doors open out to a fully screened lanai that spans the entire width of the living area, creating a true extension of the home and the perfect place to relax while overlooking the water. The split floor plan offers privacy, with a spacious primary suite positioned to capture lake views, complete with a large walk-in closet and a spa-style en-suite bathroom featuring double vanities and a walk-in shower. One of the additional bedrooms also features its own en-suite bathroom, creating a secondary primary suite—ideal for guests or multi-generational living. The remaining bedroom is well-sized and positioned for convenience. Step outside and embrace the lifestyle this property was built for. With your own private dock, you can moor your boat and enjoy direct access to the Chain of Lakes. Cruise across to local favorites like Harborside Restaurant and take in some of the best sunsets Central Florida has to offer. Additional features include plantation shutters on the front of the home, a spacious indoor laundry room, a detached storage shed, and a rare drive-through 3-car garage with access from the front all the way to the backyard—perfect for boats, trailers, or additional vehicles. With no HOA and close proximity to downtown Winter Haven, this property delivers a unique combination of space, convenience, and true waterfront living. This is more than just a home—it’s a rare opportunity to own a standout piece of lakefront property on the Chain.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$394,000398 Days on yellowkey MLS ID: P4934266
REDUCED by $5,000 (1.3%) on 04/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1603 Built: 2006Monthly Fee: $17 Tax: $5,194 (2024)Community: Island LakesSingle Family
Taxes:$5,194
Remarks: One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $45,000 PRICE IMPROVEMENT! Lakefront living on the Chain of Lakes just became an incredible opportunity. Welcome to 4099 Island Lakes Dr — a well-maintained 3 bedroom, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Major updates already handled with a brand new roof installed February 9, 2026, giving buyers peace of mind and potential insurance benefits. Combine that with a significant $40K price reduction, and this property stands out in today’s market. Inside, you’ll find a bright and open layout filled with natural light. The spacious living area flows seamlessly into the kitchen and dining space, ideal for entertaining or relaxing after a day on the water. The primary suite features beautiful lake views, a private bath, and generous closet space. Step outside to freshly installed sod and updated landscaping that enhances curb appeal and creates the perfect setting for outdoor gatherings. With direct lake access, enjoy boating, fishing, kayaking, and stunning sunset views right from your backyard. Whether you're searching for a full-time residence, seasonal escape, or lakefront investment, this Chain of Lakes home offers location, lifestyle, and value. Schedule your private showing today.
Listing Agent: Don Jerue (863-259-9550)
129 MORNING GLORY CIR, WINTER HAVEN, FL 33884
$317,00042 Days on yellowkey MLS ID: P4938153
REDUCED by $18,000 (5.4%) on 04/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1888 Built: 2002Monthly Fee: $52 Tax: $3,638 (2025)Community: Morningside Ph 02Single Family
Taxes:$3,638
Remarks: Designed for the way you live today, this beautifully updated 3BR/2BA home offers a modern, open floor plan ideal for gathering with family, entertaining friends and great for enjoying relaxed backyard barbecues. Built in 2002, offering just under 1900 square feet of comfortable living space. Topped with a long-lasting, low maintenance tile roof designed for lasting durability, this home is ideally positioned with no direct neighbors-backing up to peaceful green space for added privacy. Thoughtfully updated with numerous recent improvements, providing peace of mind for the next owner. Major upgrades include new HVAC system (2023), hot water heater (2025), new flooring throughout (2025), freshly painted, complemented by new ceiling fans, light fixtures and hardware throughout. While functionality has been enhanced inside recent upgrades outside include irrigation improvements (2023), a garden sump pump (2026) and exterior paint just completed, offering even more value and curb appeal. Enjoy resort-style living in this gated community featuring a heated pool, spa, tennis/pickleball courts and Community Clubhouse. Residents also have access to a private boat ramp and dock-perfect for fishing or taking in breathtaking sunsets on Lake Winterset. Winter Haven is a vibrant and growing lakeside city known for its Chain of Lakes lifestyle, charming downtown with weekend farmers market and ski shows. Winter Haven is also home to attractions like LEGOLAND Florida Resort and Peppa Pig-offering the perfect balance of relaxation, recreation and convenience to Lakeland/Tampa, Orlando, major airports and both coasts. The perfect place to call home!
Listing Agent: Laurie Nock (937-218-0031)
731 CANBERRA RD, WINTER HAVEN, FL 33884
$325,000164 Days on yellowkey MLS ID: L4957294
REDUCED by $10,000 (3.0%) on 04/25/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 1989Monthly Fee: $17 Tax: $2,207 (2024)Community: Cypresswood Patio HomesSingle Family
Taxes:$2,207
Remarks: Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.
Listing Agent: Melissa Witter (863-206-8744)
2008 RIVER HAWK LOOP, WINTER HAVEN, FL 33880
$385,0009 Days on yellowkey MLS ID: S5148468
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2032 Built: 2026Monthly Fee: $98 Tax: $228 (2025)Community: Residences At Winter HavenSingle Family
Taxes:$228
Remarks: Excellent investment opportunity with leaseback in place. This featured Everglades model home by Laref Homes is being offered with a 2-year leaseback through April 30, 2028, at $2,570/month, providing immediate rental income. There is an effortless style to this stunning 2,032 sq. ft. home, featuring three bedrooms plus a versatile den and an open-concept layout. Premium vinyl flooring flows seamlessly throughout, leading to a beautifully designed kitchen with a striking waterfall island. The spacious living area connects naturally to a covered lanai, creating a bright and modern living environment. Loaded with upgrades, this model home offers a unique combination of design and functionality. Furniture not included.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)
1028 S LAKE MARIAM DR, WINTER HAVEN, FL 33884
$850,00039 Days on yellowkey MLS ID: P4938222
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3255 Built: 2005Monthly Fee: $25 Tax: $5,715 (2025)Community: Waters Lake MariamSpa: YesSingle Family
Taxes:$5,715
Remarks: Welcome to your slice of LAKEFRONT, POOL HOME paradise on the pristine shores of Lake Mariam in Winter Haven, Florida. This stunning 3-bedroom, 2.5-bathroom home with a versatile BONUS ROOM offers the ultimate Florida lifestyle, complete with direct lake access, a private dock, and breathtaking water views right from your own backyard. Built to last and designed for low maintenance, this home features a durable METAL ROOF and solar panels, offering peace of mind and significant savings on energy costs year after year. Whether you’re sipping morning coffee while watching the sunrise over Lake Mariam or heading out for a day on the water, this property delivers the lakefront living experience you’ve been searching for. Inside, the thoughtfully designed floor plan offers three comfortable bedrooms, two and a half bathrooms, and a spacious bonus room perfect for a home office, media room, guest suite, or playroom. The heart of the home is the beautifully designed kitchen, featuring abundant cabinetry, stainless steel appliances, granite countertops, a center island, breakfast bar seating, glass-front upper cabinets, recessed lighting, and an open layout that flows seamlessly into the main living areas. With its generous workspace and water views from the adjoining living space, this kitchen is ideal for both everyday living and entertaining. The oversized 2-car garage provides ample storage for vehicles, watercraft equipment, and all your lake toys. Step outside and discover what truly sets this property apart: your own private HEATED POOL and SPA, along with an impressive private dock stretching out over the serene waters of Lake Mariam, ideal for boating, fishing, kayaking, or simply soaking in the natural Florida scenery. With direct lake access and one of the longest docks on the water, this is a rare find in today’s market. Located in Winter Haven’s sought-after lake corridor, you’re just minutes from dining, shopping, Legoland Florida, and easy access to I-4 connecting you to both Tampa and Orlando. Schedule your showing today!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Mabel Vassallo (863-604-0499)
1033 SAWGRASS DR, WINTER HAVEN, FL 33884
$364,00094 Days on yellowkey MLS ID: P4937685
REDUCED by $5,000 (1.4%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1879 Built: 2022Monthly Fee: $5 Tax: $7,458 (2025)Community: Lake Ashton West Ph Ii SouthSpa: NoSingle Family
Taxes:$7,458
Remarks: Welcome to 1033 Sawgrass Dr, where modern comfort meets thoughtful upgrades in this beautifully maintained 3-bedroom, 2-bath home. Designed with everyday living in mind, this home features an open-concept layout filled with natural light, creating a bright and inviting space perfect for both relaxing and entertaining. The kitchen offers quality finishes and a clean, contemporary feel, seamlessly connecting to the main living area. Elegant crown molding adds a refined touch, while plantation shutters provide both style and function throughout the home. The primary suite offers a spacious retreat, complete with a large walk-in closet for ample storage. Outside, the widened driveway adds extra convenience and functionality—an upgrade you’ll appreciate daily. Located in the highly sought-after Lake Ashton community, residents enjoy access to an impressive array of amenities designed for an active and social lifestyle. From two 18-hole golf courses to expansive clubhouses, fitness centers, indoor and outdoor pools, and courts for tennis, pickleball, bocce, and more, there’s always something to do. Additional features include a bowling alley, movie theater, arts and crafts spaces, pet areas, and a full calendar of community events. Positioned in Central Florida with convenient access to both Tampa and Orlando, this property offers the perfect balance of comfort, convenience, and lifestyle.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Veronica Bard (863-670-7526)
2 CASARENA CT, WINTER HAVEN, FL 33881
$320,00097 Days on yellowkey MLS ID: L4958770
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2377 Built: 1983Monthly Fee: $310 Tax: $5,755 (2025)Community: Casarena On LakesSingle Family
Taxes:$5,755
Remarks: **RECENTLY REDUCED AND PRICED TO SELL** Welcome to this spacious 3 bedroom, 3 bath townhouse located in the private, gated, lakefront community of Casarena on the Lakes. Situated on the Winter Haven Chain of Lakes with a desirable south-facing view of Lake Cannon, this home offers the rare opportunity to enjoy both sunrise and sunset views right from your own space. Three-bedroom properties in this community are seldom available. This would make a PERFECT winter retreat! Boasting over 2,300 square feet of living space, the home provides plenty of room to live comfortably. The second level features two primary suites. One includes a private balcony with beautiful lake views, perfect for morning coffee or winding down in the evening. That same suite also offers an oversized walk-in shower with a built-in steam sauna, creating a relaxing, spa-like retreat at home. The third bedroom is located on the main level and works perfectly for guests or a home office. The kitchen has been thoughtfully updated with high-end stainless steel appliances, granite countertops, and solid wood cabinetry. It opens to the dining area and main living space, which are separated by a striking stone fireplace, making the layout ideal for both everyday living and entertaining. Parking is a standout feature with a two-car garage PLUS an additional parking space, providing room for three vehicles. Community amenities include a pool, tennis court, and a newly rebuilt composite dock with boat slips available on a first-come basis. Leave your boat in the water so you’re always ready for early-morning fishing, evening cruises, or a spur-of-the-moment dinner at one of the Chain’s waterfront restaurants. Additional updates to this home include two new A/C units, a WHOLE-HOUSE GENERATOR, and a tankless water heater, offering comfort and peace of mind year-round. This home delivers space, thoughtful upgrades, and true lakefront living in a secure, well-kept community.
Listing is courtesy of: BERRY REALTY & APPRAISAL SERVICES PA (863-224-6857)
Listing Agent: Kylie Berry (863-224-6857)
2349 SALZBURG LOOP, WINTER HAVEN, FL 33884
$309,900107 Days on yellowkey MLS ID: P4937532
REDUCED by $5,000 (1.6%) on 04/15/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1724 Built: 2008Monthly Fee: $290 Tax: $4,041 (2025)Community: Vienna Square Ph 01Single Family
Taxes:$4,041
Remarks: HERONS, CRANES, EGRETS, AND DUCKS! You'll have a birds eye view of Florida's most beautiful waterfowl from this custom 3 bedroom 3 bath home located in charming Vienna Square. This excellent floor plan offers a private 3rd bedroom with en suite bath perfect for the momma, in-laws, or extra guests. Enjoy the private interior courtyard with an in-ground spa, and space for fun get togethers. Check out the upgraded wood cabinets pull outs, granite countertops, 7 foot doors, elaborate crown molding, and deep wood trim throughout this well planned home. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a fun filled lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for retirement living. Monthly fees include lawn mowing, a Spectrum Internet/TV package, and all community amenities. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!
Listing Agent: Marti Sutton (863-206-0563)
104 AVENUE K AVE NE, WINTER HAVEN, FL 33881
$209,000285 Days on yellowkey MLS ID: P4935577
3 Days Off yellowkey (back on 5/2/2026)
REDUCED by $8,000 (3.7%) on 04/14/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1190 Built: 1946 Tax: $1,783 (2024)Community: Silvercrest AddSingle Family
Taxes:$1,783
Remarks: Under contract-accepting backup offers. SELLER MOTIVATED. MAKE OFFER! Looking for an affordable, move-in ready home under $250k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find a modern kitchen with granite countertops, stainless steel appliances, open shelving, and deep teal subway tile that pops. The layout is open and airy with luxury vinyl plank floors, fresh paint, and natural light throughout. Major updates are already done for you—new roof (2023), updated electrical and panel (2023), PVC plumbing (2025), and a new tankless water heater (2025). There's also a detached shed with laundry and extra storage, plus room to park a boat, RV, or trailer—no HOA rules to worry about. Located across from public lakes and close to downtown Winter Haven, the Winter Haven Hospital, Polk State College, parks, trails, and transit, this home makes it easy to live, work, and play in one of the most walkable parts of town. If you've been searching for a 3-bed home with updates and a fenced yard near the heart of Winter Haven, 104 Avenue K NE is ready to welcome you home.
Listing Agent: April Spaulding (863-866-1044)
260 GREENFIELD RD, WINTER HAVEN, FL 33884
$370,00083 Days on yellowkey MLS ID: P4937787
REDUCED by $23,000 (5.9%) on 05/02/2026
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)
1250 31ST ST NW, WINTER HAVEN, FL 33881
$225,000157 Days on yellowkey MLS ID: O6361582
4 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1176 Built: 1960 Tax: $2,529 (2024)Community: West Cannon HeightsSingle Family
Taxes:$2,529
Remarks: Under contract-accepting backup offers. Price Improvement — Exceptional Value! Beautifully renovated home tucked away in a quiet, no-HOA community and situated on a spacious corner lot offering added yard space and great curb appeal. This move-in ready property features an open-concept layout with modern finishes, abundant natural light, and fresh updates throughout. The spacious primary suite includes a private bath, and the updated kitchen showcases stylish finishes and appliances ready for everyday living. Laundry hook-ups included for convenience. Well-priced and eligible buyers may qualify for financing programs that assist with closing costs — ask for details.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Daryle Henry, Jr. (863-651-4792)
151 1ST ST, WINTER HAVEN, FL 33880
$254,900172 Days on yellowkey MLS ID: TB8447780
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1259 Built: 2023 Tax: $2,032 (2024)Community: Leslie J ASingle Family
Taxes:$2,032
Elementary School: Jewett School of the Arts
Remarks: Welcome to your move in ready dream home! Built in 2023 and still sparkling like new, this 3 bedroom , 2 bath beauty comes with an attached 1 car garage, sits at the at the end of of a peaceful dead end street in the highly sought after unincorporated Winter Haven-offering the perfect blend of privacy and convenience. Step inside to an open, light filled floor plan where every detail shines. The heart of the home is a chef's kitchen featuring gorgeous granite countertops, with a large breakfast bar perfect for morning coffee or cold afternoon cocktails and casual dinners with friends and family. Featuring ample cabinetry and spacious pantry make cooking a real joy. Out back escape to your own lush green tropical oasis - shaded by mature trees and lush greens complete with a handy storage shed for your tools and toys. Back yard would be great for having barbecue and making memories.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Juan Garcia (352-467-4043)
265 LAKE THOMAS DR, WINTER HAVEN, FL 33880
$348,95069 Days on yellowkey MLS ID: L4959685
REDUCED by $1,000 (0.3%) on 05/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1517 Built: 1985 Tax: $1,169 (2025)Community: Timber WoodSingle Family
Taxes:$1,169
Remarks: Welcome to this beautifully renovated lakefront retreat on Thomas Lake in Winter Haven! This stunning two-story home combines modern upgrades with warm character and breathtaking water views. Currently, the 3rd bedroom is set up as a loft, offering breathtaking lake views and including a closet. Step inside to tall vaulted ceilings creating an open, airy layout filled with natural light. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel appliances, quartz countertops, brand-new cabinetry, and closet pantry – providing plenty of storage and room to cook or entertain. A cozy fireplace with a raised hearth and wood accents adds charm and a welcoming focal point to the living space. This home also features beautifully updated bathrooms and walk-in closets. The home also includes a new electric water heater and newer A/C (2022) for added efficiency and peace of mind. Outside, you’ll find a newer roof (2022), fresh exterior paint, an attached 1-car garage with driveway, and plenty of space to enjoy the outdoors. Relax or entertain on the large rear patio, or unwind on the private, enclosed back porches on both floors, each offering gorgeous, tranquil lake views. This move-in-ready lakefront gem blends modern updates, comfort and scenic surroundings, making it a rare opportunity you won’t want to miss!
Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)
Listing Agent: Angie Reynolds (863-838-1090)
1640 NW PEARCE RD, WINTER HAVEN, FL 33881
$330,000278 Days on yellowkey MLS ID: L4954651
REDUCED by $15,000 (4.3%) on 05/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1421 Built: 2025Community: Lake View Sub Pb 3 Pg 80Single Family
Taxes:$0
Remarks: Discover the perfect blend of modern living and convenience in this brand new 3-bedroom, 2-bathroom home located in the heart of Winter Haven, just minutes from the serene shores of Lake Hartridge. Best of all, there’s NO HOA to worry about! As you step inside, you’ll be greeted by a bright and airy open floor plan that flows seamlessly throughout the home. The luxury vinyl plank flooring adds both elegance and durability, making it a great choice for busy households. The heart of the home is undoubtedly the beautiful kitchen, which features stainless-steel appliances, quartz countertops, and plenty of cabinetry to store all your cooking essentials. The kitchen design allows for easy interaction with guests in the spacious living room, ensuring you never miss a moment while entertaining. Retreat to the primary bedroom, a sanctuary designed for relaxation. This inviting space comes complete with a generous walk-in closet and a luxurious ensuite bathroom, featuring dual sinks and a modern walk-in shower—providing a perfect spot to unwind after a long day. The two additional bedrooms are thoughtfully designed with equal sizing and each boasts a walk-in closet, ideal for family members or guests. The second bathroom, conveniently located near the entrance of the home, includes a shower and tub combination, offering both comfort and functionality. Situated in the heart of WinterHaven, this home places you in close proximity to a variety of retailers, restaurants, and shops, ensuring you have everything you need right at your fingertips. Plus, the adjacent home is also available for sale and currently under construction, offering a unique investment opportunity. Don’t miss your chance to own this exceptional new home in Winter Haven—schedule a tour today and envision the possibilities!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: John Hubbert, Jr (863-243-4024)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.