Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Living Area Square Feet: 2500 to 2999
Do Not Show Listings
Winter Haven - 76 properties found
1394 OAKMONT DR, WINTER HAVEN, FL 33884
$549,50039 Days on yellowkey MLS ID: L4961930
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2606 Built: 2018Monthly Fee: $5 Tax: $10,681 (2025)Community: Lake Ashton West Ph 2Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,681
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amenity-rich lifestyle. Residents enjoy access to championship golf courses, multiple clubhouses, indoor and outdoor pools, fitness centers, tennis and pickleball courts, bowling, movie theater, restaurant and lounge areas, walking and biking paths, lake access, and a vibrant social atmosphere that makes Lake Ashton one of Central Florida’s premier active adult communities. This beautifully upgraded Ashton floor plan offers approximately 2,606 square feet of living space with 3 bedrooms, 2 full bathrooms, a den, flex room, and a spacious 2-car plus golf cart garage with room for up to 2 golf carts. Inside, you’ll find soaring cathedral ceilings, tray ceiling accents, crown molding, recessed lighting, updated fixtures, and a seamless blend of laminate flooring and ceramic tile throughout. The gourmet kitchen features granite countertops, solid wood 42-inch cabinetry with crown molding, stainless steel appliances including a Bosch dishwasher and double convection ovens, along with abundant prep and storage space. Designed for both comfort and efficiency, the home includes a FULLY PAID OFF SOLAR PANEL SYSTEM with transferable warranty, whole-house generator, enhanced landscaping, updated irrigation system, abundant storage, and negotiable furnishings for a potential move-in-ready opportunity. The spacious primary suite offers custom closets, soaking tub, oversized walk-in shower, and private sauna. Enjoy Florida living year-round from the oversized screened lanai complete with remote-control privacy shades, outdoor kitchen with stainless steel grill, kegerator, wine fridge, barbecue area, and an impressive Veranda 10-person hybrid swim spa. The SELLER IS ALSO INCLUDING THE GOLF CART WITH THE SALE, making it even easier to enjoy everything the Lake Ashton lifestyle has to offer.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
4223 SAN ROCCO WAY, WINTER HAVEN, FL 33884
$280,000244 Days on yellowkey MLS ID: S5137072
REDUCED by $45,000 (13.8%) on 06/17/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2522 Built: 2023Monthly Fee: $22 Tax: $7,612 (2024)Community: Villamar Ph 5Single Family
Taxes:$7,612
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2024
Middle School: Denison Middle
Remarks: Virtually Staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and connection. The kitchen shines with stainless steel appliances, an oversized pantry, and cabinets with updated fixtures, all opening to the main living area with NEW laminate flooring—creating a seamless space for gathering and entertaining. A bedroom and full bathroom on the main floor offer ideal flexibility for guests or multi-generational living. Upstairs, you’ll find four additional bedrooms, a loft that’s perfect for a home office or a cozy nook to unwind and recharge, and a conveniently located laundry room. The oversized primary suite features a large walk-in closet and an ensuite bathroom complete with a stand-alone shower, upgraded shower head, and linen closet for added convenience. Step outside to a fully fenced backyard, offering privacy and plenty of space to create your own outdoor retreat—whether that means adding a future pool, garden, or simply enjoying a quiet evening of relaxation. The oversized under-the-stairs storage and two-car garage add even more practicality, while the LOW HOA helps keep ownership easy and affordable. Perfectly situated just off US-27, residents enjoy proximity to dining, shopping, and grocery options, as well as easy access to I-17. Outdoor enthusiasts will love being near the Winter Haven Chain of Lakes, ideal for boating, kayaking, fishing, or simply soaking up the sunshine. Plus, the charming Downtown Winter Haven Historic District is nearby—home to local restaurants, boutiques, and community events like First Fridays, the Wine, Chocolate & Cheese Festival, and so many more! For a weekend of fun with the family and friends, LEGOLAND is only 3.5 miles away! This home beautifully blends modern comfort, functional space, and a convenient location—making it a must-see in the heart of Winter Haven. This is the one you've been waiting on. Schedule a showing today and make it yours!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Brianna Perez Montalvo (407-687-3837)
15 LAKE HOWARD DR NW, WINTER HAVEN, FL 33880
$240,00079 Days on yellowkey MLS ID: TB8493899
REDUCED by $10,000 (4.0%) on 06/23/2026
Bed: 6 Bath: 4.0 Liv Area Sq Ft: 2883 Built: 1920 Tax: $5,897 (2025)Community: Leonards SubSingle Family
Taxes:$5,897
Elementary School: Inwood Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!
Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)
Listing Agent: Clarisa Moody (813-446-2003)
1328 DAISY FIELD DR, WINTER HAVEN, FL 33884
$380,00075 Days on yellowkey MLS ID: L4960820
REDUCED by $10,000 (2.6%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2024Monthly Fee: $30 Tax: $7,633 (2025)Community: Harmony/Lk Eloise Ph 1Single Family
Taxes:$7,633
Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!
6261 PINEHURST LOOP, WINTER HAVEN, FL 33884
$585,000107 Days on yellowkey MLS ID: L4959857
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2512 Built: 2021Monthly Fee: $5 Tax: $10,832 (2025)Community: Lake Ashton West Ph Ii NorthSpa: NoSingle Family
Taxes:$10,832
Remarks: Experience the best of Florida resort-style living in this exceptional Ashton floor plan located in the sought-after Lake Ashton Golf Club Community. Offering 3 bedrooms, 2 baths, a den, and 2,512 square feet of thoughtfully designed living space, this beautifully maintained home combines elegance, comfort, and functionality. A paver driveway, manicured landscaping, and stunning leaded-glass French doors create impressive curb appeal. Inside, you'll find an open-concept design enhanced by plantation shutters, abundant natural light, and a wall of 8-foot sliding glass doors that seamlessly connect the indoor and outdoor living spaces.The gourmet kitchen is sure to impress with Seacrest Birch cabinetry featuring soft-close drawers, Silestone countertops, ample workspace, and generous storage. The spacious primary suite offers a relaxing retreat complete with custom his-and-her closets, dual vanities, and a dedicated granite makeup station. A versatile den provides the perfect space for a home office, hobby room, or guest overflow.Certified as an Environments for Living Green Home, this residence was designed with energy efficiency and long-term savings in mind.Step outside to your own private oasis. The oversized screened veranda features custom flooring, a fully equipped outdoor kitchen, and a heated saltwater pool—ideal for entertaining guests or enjoying peaceful Florida evenings year-round.The extended garage easily accommodates larger vehicles and a golf cart and includes epoxy-coated floors and screened garage doors.Lake Ashton offers an unparalleled lifestyle with two 18-hole golf courses, clubhouses, fitness centers, resort-style pools, tennis, pickleball, bowling, dining, movie theater, and countless social activities. Whether you're seeking an active lifestyle or a peaceful retreat, you'll find it here. Washer, dryer, and front flagpole do not convey. Schedule your private showing today and discover why so many choose to call Lake Ashton home.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Anita Lowe (863-269-6461)
341 MANDOLIN LN, WINTER HAVEN, FL 33884
$430,00018 Days on yellowkey MLS ID: L4962452
REDUCED by $9,000 (2.1%) on 06/24/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2506 Built: 2011Monthly Fee: $56 Tax: $4,408 (2025)Community: MandolinSingle Family
Taxes:$4,408
Remarks: NEW PRICE + AMAZING VALUE IN GATED COMMUNITY OF MANDOLIN! Fall in love with this 4-bedroom, 2-bathroom NEWLY ADDED SALT WATER HEATED POOL home PLUS OFFICE/FLEX ROOM offering an impressive 2,506 square feet of living space in a highly desirable gated community. You’ll appreciate the exceptional curb appeal, extended driveway, detailed custom trim work, Luxury Vinyl Plank and tastefully added upgrades throughout the home. Discover a spacious split floor plan featuring elegant accents that welcome you in. The kitchen features granite countertops, solid wood cabinets, NEWER appliances and a large pantry.The oversized indoor laundry room makes your life easy! The flexible office/den space is perfect for working from home, a playroom, fitness area, or additional guest space. The spacious primary suite is privately tucked away and features oversized his-and-her walk-in closets along with a beautifully remodeled primary bathroom complete with an enlarged walk-in shower, stylish new tile and backsplash, and a relaxing separate garden tub. Three additional generously sized bedrooms provide plenty of room for family and guests. Step outside to your own private backyard retreat and enjoy days of fun in the sun featuring a newly added heated saltwater pool and pool cage, screened porch, patio paver deck, and fully fenced backyard with double gate—perfect for entertaining, relaxing, and enjoying the Florida lifestyle year-round. You can also store your boat or outdoor toys! Additional features include termite bait system, regular pest control maintenance, and much more! Conveniently located near LEGOLAND, THE BEAUTIFUL CHAIN OF LAKES, schools, shopping, medical facilities, restaurants, an all Winter Haven has to offer. Easy commute to all Central Florida Attractions and Florida Beaches! Don't miss this incredible opportunity! CALL TODAY FOR A TOUR! Your Florida Dream home awaits!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Tina Heim, Pa (863-370-1786)
1213 MICHELANGELO LN, WINTER HAVEN, FL 33884
$559,90040 Days on yellowkey MLS ID: O6408212
REDUCED by $5,000 (0.9%) on 06/19/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2894 Built: 2022Monthly Fee: $76 Tax: $4,722 (2025)Community: Estates/Lk FlorenceSingle Family
Taxes:$4,722
Elementary School: Elbert Elem
Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Luxury Heated Pool • Resort-style backyard • Move-In Ready Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
3600 JULIUS ESTATES BLVD, WINTER HAVEN, FL 33881
$340,000299 Days on yellowkey MLS ID: O6339978
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2014Monthly Fee: $105 Tax: $3,256 (2024)Community: Lake Smart EstatesSingle Family
Taxes:$3,256
Remarks: AMAZING two-story home!!! Located in a BEAUTIFUL LAKEFRONT COMMUNITY! HUGE, fenced corner lot, very nice layout with a FLEX area/room that can be used as a formal Livingroom, office, or den, large master bedroom with a nice bathroom with dual sinks, walk in shower & walk-in closet, laundry room, 2 car garage & so much MORE**Seller may consider buyer's concessions **CALL YOUR AGENT FOR A PRIVATE SHOWING**
Listing is courtesy of: LUXURY REAL ESTATE GROUP LLC (561-929-7304)
Listing Agent: Gladys Falcon (863-812-1771)
605 SW SARNER PASS WAY W, WINTER HAVEN, FL 33881
$399,000115 Days on yellowkey MLS ID: G5108932
REDUCED by $14,000 (3.4%) on 04/20/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2676 Built: 2022Monthly Fee: $76 Tax: $4,782 (2025)Community: Lake Lucerne Ph 5Spa: NoSingle Family
Taxes:$4,782
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Boone Middle
Remarks: Move-in ready and beautifully maintained, this exceptional 4-bedroom, 2.5-bathroom home offers modern comfort, thoughtful design, and outstanding convenience. Built in 2022, this spacious two-story residence is ideally situated on a desirable corner lot in the sought-after Lake Lucerne community. The main level features an open-concept layout that seamlessly connects the living room, dining area, and gourmet kitchen—perfect for everyday living and entertaining. The kitchen is appointed with granite countertops, stainless-steel appliances, a large center island with seating, a deep sink, upgraded fixtures, abundant cabinetry, and generous prep space. A private office/den with double doors provides the flexibility for a home office, fitness room, study, or playroom. A convenient half bath is also located on the first floor. Upstairs, retreat to the spacious primary suite featuring a large walk-in closet and a luxurious ensuite bathroom with dual granite vanities and an upgraded walk-in shower. The additional bedrooms has ample space for family and guests, while the centrally located upstairs laundry room adds everyday convenience. Step outside to enjoy Florida living at its finest. The covered rear lanai overlooks a spacious backyard with plenty of room for entertaining, relaxing, gardening, or future outdoor enhancements. Residents of Lake Lucerne enjoy access to community amenities including two swimming pools, a playground, and beautifully maintained common areas. Conveniently located near Highway 27 and approximately 20 minutes from I-4, this home offers easy access to both Orlando and Tampa. You'll be just 45 minutes from Walt Disney World, 20 minutes from LEGOLAND Florida, 35 minutes from Lakeland, and minutes from Winter Haven Hospital, Downtown Winter Haven, shopping, dining, Publix, Walmart, and everyday conveniences. For added peace of mind, the roof, HVAC system, and water heater are all approximately four years old. Owner financing available for qualified buyers, creating a unique opportunity for those seeking flexible financing options. Schedule your private showing today and discover everything this beautiful home has.
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Nan Seelall Llc (352-978-1050)
1302 LAKE ELBERT DR SE, WINTER HAVEN, FL 33880
$589,50019 Days on yellowkey MLS ID: L4962421
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2626 Built: 1947 Tax: $7,971 (2025)Community: Elbert HillsSpa: NoSingle Family
Taxes:$7,971
Remarks: Come and See this Amazing Lake Front Home Located in the Water Skiing Capital of the World, on Lake Elbert in Winter Haven, FL. As you enter the front door of this beautiful Home the hardwood floors will delight your eyes as you look down the long foyer to the right that leads pass the kid's 2 Bedrooms area for them to enjoy, to a large Family room with Lake Views that will be one of your favorite places to relax. Going back down the foyer you will end up seeing the 1st floor Master King Ensuite with Lake views and a private bathroom on the left, and the Stunning Gourmet Kitchen on the right flowing into a light-filled Dining Sunroom with Lake Views, perfect for entertaining. This Home is the ideal home to Live in full time, or Enjoy it here during your favorite time of the year, or use it for a short term rental or longer term while you're at your other home. This Home easily sleeps 10 with it's 5 Bedroom, 4.5 Bathrooms, a kid's area that will sleep 4, while the Adults can appreciate 3 King Master Ensuites with their own Bathrooms. The kid's 2 bedrooms area with a bathroom circles back with a door into the Kitchen, the HUB of the home. You can go out the rear door to the nice patio and the 2 car Garage / Game Room that also has the Laundry Room and a Full Bathroom with a walk in Shower. Back inside, going up to the 2nd floor you have a door going out to the balcony in the front of the home over the 1st floor patio that allows for the peaceful Lake views. The other 2 Master King Ensuites with Walk in Closets and Private Full Bathrooms. Sitting on almost 1/2 acre on a hill up from the Lake, this AMAZING HOME with so much to love and could be Yours's to ENJOY all year or create a Great Cash Flow for your Retirement. It is only about a 10 minutes drive to LEGOLAND, and aproxamently 30 minutes or so to DISNEY WORLD, UNIVERSAL STUDIOS, SEA WORLD, and OTHER PARKS, and only about 1.5 hours to the BEAUTIFUL FLORIDA BEACHES OR EITHER SIDE OF THE STATE. Come and See this Amazing Home the is Priced to SELL.
Listing is courtesy of: ELEVATE REAL ESTATE BROKERS (954-772-3870)
Listing Agent: Russ Yerton (863-602-5944)
5025 KAIA AVE, WINTER HAVEN, FL 33884
$349,99043 Days on yellowkey MLS ID: TB8502447
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $40 (0.0%) on 06/15/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2631 Built: 2026Monthly Fee: $15 Tax: $5,000 (2025)Community: VillamarSpa: NoSingle Family
Taxes:$5,000
Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! Entertain guests with ease with an open kitchen which overlooks the dining and great room. First floor flex space can be best used to fit your needs. Upstairs primary suite features an oversized walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)
Listing Agent: Bryan Sumner (813-336-5895)
445 TALAMONE DR, WINTER HAVEN, FL 33884
$555,00019 Days on yellowkey MLS ID: P4938949
REDUCED by $10,000 (1.8%) on 06/19/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2653 Built: 2002Monthly Fee: $83 Tax: $6,593 (2025)Community: Tuscany At WintersetSingle Family
Taxes:$6,593
Remarks: Nestled within the exclusive gated community of Tuscany, a charming neighborhood of just 18 homes in Southeast Winter Haven, this 4 bedroom, 3 bath pool home offers over 3,300 square feet under roof on a private 0.33 acre lot. Designed for both comfortable living and entertaining, the home features a dedicated office, formal dining room, living room, and an impressive 25' x 17' poolside bonus room complete with a custom wall-to-wall hardwood entertainment center, surround sound, upgraded lighting, tile flooring, and ceiling fan. The spacious kitchen showcases abundant Kraft Maid cabinetry, granite countertops, generous workspace, and a sunny breakfast nook overlooking the pool. A thoughtfully designed triple-split bedroom floor plan provides privacy for family and guests, while multiple access points lead to the screened pool and outdoor living areas. The spacious primary suite features a double-sink vanity, garden tub, separate shower, private water closet, and oversized walk-in closet. It also as access to the pool area. Additional highlights include hand-scraped real wood flooring throughout most of the home, including the primary suite, an outdoor summer kitchen with built-in gas grill, sink, and refrigerator, indoor laundry room, oversized two-car garage, expanded driveway with parking for up to eight vehicles, a separate entrance to the bonus room, and mature landscaping with an irrigation system on a dedicated meter. The large private backyard offers plenty of space beyond the screened pool area, creating a peaceful retreat while remaining conveniently located less than a mile from schools and Publix supermarket. Experience this exceptional property like never before with a 3D Interactive Virtual Tour or Virtual Reality featuring a 2D Floor Plan and immersive 3D Dollhouse Model, plus a 360-degree Interactive Aerial Virtual Tour showcasing the entire Tuscany community and panoramic views as far as the eye can see. The home features a stunning collection of modern gold crystal chandeliers throughout, including a 23.6" dimmable LED crystal chandelier with adjustable color temperatures in the hallways and kitchen, an elegant gold crystal flush-mount chandelier in the master bedroom, a large modern crystal LED chandelier that serves as a beautiful focal point in the living room, and a luxurious 40" gold rectangular crystal chandelier with 16 lights above the dining area, creating a cohesive, contemporary design with lighting and timeless elegance throughout the home. Meticulously maintained, this one-of-a-kind pool home is a rare opportunity to own a beautiful property in one of Southeast Winter Haven's most desirable gated communities.
Listing is courtesy of: 3D TEAM REALTY LLC (863-604-3662)
Listing Agent: Jimmy Aguilar (863-604-3662)
440 PALMA CEIA RD, WINTER HAVEN, FL 33884
$800,00014 Days on yellowkey MLS ID: O6415193
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2575 Built: 2023Monthly Fee: $149 Tax: $6,403 (2025)Community: Cypresswood Golf/CcSpa: NoSingle Family
Taxes:$6,403
Remarks: Over 1 Acre with Golf Course Views in Cypresswood Golf & Country Club. Discover a rare opportunity to own one of the LARGEST residential lots in Cypresswood Golf & Country Club, one of Winter Haven's premier gated golf communities. Built in 2023 and situated on 1.17 acres, this exceptional 4-bedroom, 3-bathroom residence offers luxury, privacy, and modern living with expansive views of the 2nd green and 9th tee of the Ron Garl-designed championship golf course. A long private driveway lined with Florida-friendly landscaping leads to an expansive paver parking courtyard and oversized three-car garage featuring a professionally finished epoxy floor. Ebony-finished tongue-and-groove ceilings on both the front entry and rear screened lanai create an impressive first impression, while the Therma-Tru insulated front door with decorative glass insert welcomes you inside. The thoughtfully designed OPEN-CONCEPT FLOOR PLAN features luxury vinyl plank flooring throughout, soaring ceilings with decorative beam details, custom millwork, recessed lighting, and large windows that fill the home with natural light. The spacious great room is anchored by a custom shiplap feature wall with an electric fireplace and opens seamlessly to the covered lanai through oversized sliding glass doors. A premium Denon surround sound system serves both the great room and lanai, making entertaining effortless. The gourmet kitchen combines style and functionality with quartz countertops, a large center island, solid wood cabinetry, under-cabinet lighting, a walk-in pantry with custom shelving, Frigidaire Professional Series stainless steel appliances, and a natural gas cooktop. The spacious primary suite offers a tray ceiling with decorative beams, an oversized walk-in closet, and a luxurious ensuite bath featuring dual vanities, a garden tub, walk-in shower, and private water closet. The split-bedroom floor plan provides privacy for family and guests, and every bedroom includes a walk-in closet. Step outside and enjoy the freedom of owning more than an acre with panoramic golf course views and plenty of room to create your dream outdoor living space. Residents of Cypresswood Golf & Country Club enjoy an 18-hole championship golf course, clubhouse, restaurant, junior Olympic-sized pool, tennis and pickleball courts, and scenic roads perfect for walking, running, and biking. Conveniently located near US-27, I-4, the Polk Parkway, downtown Winter Haven, and LEGOLAND Florida Resort, this home offers an exceptional combination of luxury, space, and location.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Jessica Estrada (863-409-1771)
199 8TH ST SE, WINTER HAVEN, FL 33880
$410,0002 Days on yellowkey MLS ID: TB8521428
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2992 Built: 1961 Tax: $4,446 (2025)Community: Nydeggers West Elbert SubSingle Family
Taxes:$4,446
Remarks: Welcome to your new home! This spacious 5/2 has all you could need for functionality, family, and entertaining. Nestled just near Lake Elbert, less than a mile from downtown Winter Haven where you will find tons of local shopping, food, and lounges. On the main floor you will find both a formal and family living room, dining room, kitchen with attached laundry and plenty of pantry space, and the main bedroom with an ensuite bathroom, a built-in closet as well as a larger multi-function walk-in closet, or you can make it into an office! The ensuite bathroom has a separate door, a walk-in shower with multi heads/rain head, and a spa tub. On the second floor, you will find four additional bedrooms, the second bathroom, and the landing space can be utilized as a small living/game room area. On the second floor you will find 2 utility closets, so no toting cleaning supplies up the stairs! The home has original and working whole home exhaust, so in the cooler months or if you just like the windows open the exhaust pulls air through the house allowing for natural cooling as well as attic space to store seasonal décor. The A/C was replaced less than a year ago. Outside you will find in the front a semicircle driveway as well as a long drive that leads all the way back to the detached 2 car garage. There’s storage shelving in the garage and a working utility sink. Everything you could need in a home is right before you! all dimensions are approximate, buyer and or buyer's agent to confirm room dimensions.
Listing is courtesy of: SKYBROOK REALTY & ASSOCIATES, INC. (813-435-9683)
Listing Agent: Jenn Gibbs (863-241-9019)
256 MEREDITH BLVD, WINTER HAVEN, FL 33881
$339,99060 Days on yellowkey MLS ID: G5111558
0 Days Off yellowkey (back on 6/22/2026)
REDUCED by $35,000 (9.3%) on 06/04/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2531 Built: 2026Monthly Fee: $6 Tax: $500 (2024)Community: WillowbrookSingle Family
Taxes:$500
Remarks: Virtually Staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
6121 FOREST RIDGE WAY, WINTER HAVEN, FL 33881
$310,00079 Days on yellowkey MLS ID: TB8491651
4 Days Off yellowkey (back on 6/22/2026)
REDUCED by $5,000 (1.6%) on 05/08/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2017Monthly Fee: $90 Tax: $3,073 (2025)Community: Forest RidgeSingle Family
Taxes:$3,073
Remarks: Under contract-accepting backup offers. Virtually Staged. $15,000 deduction on 5/8! 2500 sq ft for $310,000! Step into comfort, space, and opportunity in this move-in ready 4-bedroom, 2.5-bath home located in the established Forest Ridge community of Winter Haven—with no CDD. From the moment you arrive, the inviting covered front porch and mature landscaping set the tone for what’s inside. The thoughtfully designed layout offers the perfect balance of everyday comfort and flexible living. The main level features an open kitchen and living area, a versatile bonus room near the entry—ideal for a home office, playroom, or creative space—and a convenient half bath for guests. At the center of the home, the open-concept kitchen is built for connection, featuring a center island, black and stainless steel appliances, and seamless flow into the dining and living areas—perfect for entertaining or simply enjoying day-to-day life. Recently upgraded dishwasher and garbage disposal. Durable tile flooring and recently upgraded carpet throughout all the main living spaces and upstairs bedrooms adds a clean, modern feel and abundant natural light creates a bright, welcoming atmosphere. Upstairs, you’ll find all four bedrooms, including a spacious primary suite designed for relaxation, along with two full bathrooms and a conveniently located laundry area equipped with a smart washer and dryer. Each space is designed with comfort and functionality in mind. Step outside to a generously sized backyard ready for your vision—whether it’s a future pool, outdoor kitchen, garden, or play space, the possibilities are endless. Set within the peaceful surroundings of Forest Ridge, you’ll enjoy quiet streets while being just minutes from Highway 27 and a short drive to I-4, giving you easy access to shopping, dining, schools, and everything Central Florida has to offer. This home checks all the boxes—space, flexibility, location, and value. Schedule your private showing today and see the potential for yourself!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Daniel Henzler (813-293-3603)
237 MCLEAN PT, WINTER HAVEN, FL 33884
$699,000233 Days on yellowkey MLS ID: L4957003
REDUCED by $21,000 (2.9%) on 04/30/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2961 Built: 2001Monthly Fee: $238 Tax: $6,631 (2024)Community: RenaissanceSingle Family
Taxes:$6,631
Remarks: MUST SEE! Beautiful Custom-Built Home in the Renaissance Subdivision! Welcome to your dream home nestled in the serene community of Renaissance in lovely Winter Haven, Florida. This stunning 4-bedroom, 4-bathroom model home offers the perfect blend of privacy, convenience, and resort-style living, complete with a spectacular pool area. Key Features: • Prime Location: Enjoy boat access to Lake Winterset in the chain of lakes and proximity to metro Orlando and Tampa, as well as attractions like Disney and Legoland. • Resort-Style Amenities: Full pickleball and basketball courts for active living and recreation. • Elegant Design: • Wide crown molding and baseboards throughout • 12-foot ceilings and 8-foot doors for an open and airy feel • Three sets of French doors leading to outdoor spaces • His and her walk-in closets for ample storage • Dedicated office space and formal dining room for entertaining Kitchen & Appliances: • Gourmet Kitchen: All stainless-steel kitchen appliances, including a 2022 French door refrigerator. • Smart Home Technology: Equipped with a Schlage keyless entry front door for added security and convenience. Security & Maintenance: • Advanced Security System: NASA security system with 5 cameras and motion sensors for peace of mind. • Irrigation System: 6-zone irrigation system with a separate well, updated in April 2025. Outdoor Oasis: • Salt Water Pool: Installed in 2021, with a new pool surface skimmer in 2025. • New HVAC System: Two 9-ton units refurbished in 2024, ensuring comfort year-round. • Natural Gas Tankless Hot Water Heater: Installed in 2020 for energy efficiency. • New Tile Roof: Installed in 2016, providing durability and style. • Flooring: New carpet, tile, and hardwood flooring installed in 2020. • Plantation Shutters: Added in 2020 for elegance and privacy. Waffle and Tray Ceilings: Transom windows enhance the natural light and aesthetic appeal. All windows were replaced in 2018 for energy efficiency. Additional Features: • Garage Storage: Gladiator metal garage storage system for organization. • Furniture Negotiable: Some furniture items may be negotiable for interested buyers. • Professional Landscaping: Newly updated landscaping in 2025 enhances curb appeal. This luxurious custom-built home is a true paradise waiting for you to call it your own. Don’t miss out on this incredible opportunity! Contact us today to schedule a viewing!
Listing Agent: Luis Perez Garcia (201-658-0689)
472 ARCHAIC DR, WINTER HAVEN, FL 33880
$538,00019 Days on yellowkey MLS ID: L4962519
3 Days Off yellowkey (back on 6/21/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2725 Built: 2003Monthly Fee: $79 Tax: $3,572 (2025)Community: Village Spirit Lake Ph 01Spa: NoSingle Family
Taxes:$3,572
Elementary School: Eagle Lake Elem
Remarks: Lake-access living meets modern comfort in this beautifully updated corner-lot home. Welcome to 472 Archaic Drive, originally custom built, this updated 4-bedroom, 3-bath home is situated on a corner lot in one of Winter Haven's most desirable gated communities. With a heated pool, fully fenced yard, oversized garage with tool shed/workshop, and access to outstanding neighborhood amenities, this almost 2,800 sqaure foot home offers the perfect combination of comfort, style, and functionality. You'll appreciate the spacious layout, soaring ceilings, abundant natural light, and thoughtful upgrades throughout. The stunning chef-inspired kitchen serves as the heart of the home, showcasing abundant 42" custom cabinetry, luxury stone countertops, a large center island with additional sink, stainless steel appliances, and a stylish subway tile backsplash, a walk-in pantry, and breakfast nook. Thoughtfully updated with modern finishes and timeless design, this kitchen is perfectly suited for everyday living and entertaining alike. The thoughtfully designed split-bedroom floor plan provides privacy for everyone. The spacious primary suite serves as a true retreat, featuring a luxurious ensuite bath complete with dual vanities, a relaxing soaking tub, a separate walk-in shower, and a private water closet. Generous closet space and a serene atmosphere make this the perfect place to unwind at the end of the day. Two additional bedrooms are well-sized with built in storage window seats, and separated by a unique jack-and-jill bathroom with dual vanities, creating an ideal layout for families and guests. The fourth bedroom with closet makes a great added space to the home. A third full bathroom conveniently provides supplemental access to the backyard oasis where a heated self-cleaning swimming pool, covered lanai, and fully fenced yard create the ultimate setting for year-round entertainment. Residents of this sought-after gated community enjoy access to outstanding amenities including a clubhouse, community pool, playground, private boat ramp, and dock, providing endless opportunities for recreation and enjoyment. Easy access to get to Bartow and the Polk Parkway With a new roof in 2021, this beautifully updated, meticulously maintained, and ideally located home offers the perfect combination of luxury, comfort, and Florida living.
Listing Agent: Suzie Rudd (863-508-3000)
5331 MICKEY AVE, WINTER HAVEN, FL 33884
$349,999233 Days on yellowkey MLS ID: S5137804
INCREASED by $5,000 (1.4%) on 06/11/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2670 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms.
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
1000 LENA RUN CT, WINTER HAVEN, FL 33880
$549,00018 Days on yellowkey MLS ID: L4962371
0 Days Off yellowkey (back on 6/21/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2624 Built: 2007Monthly Fee: $129 Tax: $3,309 (2025)Community: Hidden CreekSpa: NoSingle Family
Taxes:$3,309
Remarks: Under contract-accepting backup offers. Welcome to 1000 Lena Run Ct — a thoughtfully designed 4-bed, 3-bath pool home offering space, privacy, and timeless appeal. The moment you step inside, you’ll notice the attention to detail, soaring ceilings, and a smart split floor plan that truly makes sense. With an additional office or bonus room and a three-car garage, this home delivers flexibility for modern living. Perfectly positioned on nearly half an acre in one of Winter Haven’s most desirable gated communities Hidden Creek, it offers rare privacy with no rear neighbors, peaceful natural views, and regular visits from local wildlife — including bald eagles and turkeys. The layout is ideal for families, multigenerational living, or anyone seeking extra space. The screen-enclosed pool area creates a true Florida retreat — perfect for relaxing, entertaining, or enjoying year-round outdoor living. The primary suite is a haven of comfort, featuring a soaking tub and walk-in shower designed for unwinding after a long day. Located just minutes from the Polk Parkway, this home provides easy access to Lakeland and Winter Haven’s top-rated dining, shopping, medical facilities, and attractions — including Legoland, Chain of Lakes recreation, and other local favorites. Move-in ready and beautifully maintained, this property blends convenience with a tucked-away feel — a rare opportunity to own a private pool home in a sought-after Winter Haven community.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Sarah Garner (863-303-4665)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.