Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
541 HEATHER GLEN DR, WINTER HAVEN, FL 33884
$269,999132 Days on yellowkey MLS ID: O6377141
REDUCED by $15,001 (5.3%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1453 Built: 2000Monthly Fee: $33 Tax: $740 (2025)Community: Heather Glen Ph 01Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$740
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Short Sale. SHORT SALE!! SUBMIT YOUR OFFER & WE WILL SUBMIT TO THE BANK. Welcome to Heather Glen, a gated community in the heart of Winter Haven with an HOA of ONLY $150 A YEAR! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience & ready for a quick close & move in. Featuring neutral gray walls, wood-look tile flooring, and plantation shutters throughout, this open-concept home is filled with natural light and boasts a spacious master suite with walk-in closet and private bath, two additional bedrooms with a guest bath, and a bright kitchen with plenty of counter space, a window over the sink, and a cozy dinette area for your morning coffee. Enjoy the convenience of an interior laundry room, newer roof and A/C unit, and a fully fenced backyard with a separate well for irrigation. Located just minutes from Legoland, Peppa Pig Theme Park, shopping, dining, medical facilities, and downtown Winter Haven, this pristine home is the perfect rental in a sought-after location. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeavanna Lanza Pa (585-313-3408)
2049 SAN MARCOS DR SE #127, WINTER HAVEN, FL 33880
$149,9005 Days on yellowkey MLS ID: P4938940
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 666 Built: 1989Monthly Fee: $237 Tax: $893 (2025)Community: Park Lake 03 02 AmdSpa: NoCondo
Taxes:$893
Elementary School: Frank E. Brigham Academy
Remarks: MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just steps from the community clubhouse, pool, fitness room, mailboxes, and parking, you'll enjoy maintenance-free living with outstanding amenities right outside your door. Park Lake residents also enjoy access to a private dock, gazebo, and beautiful waterfront views of Lake Lulu, part of the world-famous Winter Haven Chain of Lakes, providing opportunities for boating, fishing, and enjoying Florida's natural beauty. The nearby Chain of Lakes Complex and baseball fields add to the recreational appeal. Inside, soaring vaulted ceilings in the living room, dining area, and primary bedroom create a bright and spacious atmosphere. The screened lanai offers dual entry points and the perfect place to enjoy your morning coffee or evening breeze. Major renovations completed in December 2022 include stylish kitchen cabinetry, granite countertops, under-counter refrigerator, induction cooktop, and ceramic tile flooring throughout. Additional upgrades include impact-resistant windows, a new A/C system with UV light, Nest security system, and a new washer and dryer. The location is hard to beat, with restaurants, shopping, banking, medical facilities, downtown Winter Haven, and LEGOLAND Florida all just minutes away, making this home ideal for both full-time living and seasonal enjoyment. Whether you're looking for a primary residence, winter retreat, or investment opportunity, this beautifully updated condo offers affordability, convenience, lakefront amenities, and a truly carefree Florida lifestyle. Seller financing and Private Financing Available! Do not wait, it will not last long!
Listing is courtesy of: HUT REALTY, LLC (407-559-2929)
Listing Agent: Daniel Hut (863-400-6090)
548 MARTIN LUTHER KING BLVD NE, WINTER HAVEN, FL 33881
$160,000245 Days on yellowkey MLS ID: L4956442
3 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2182 Built: 1970 Tax: $3,632 (2024)Community: Campbell & Henry SubSingle Family
Taxes:$3,632
Elementary School: Elbert Elem
Tax Year: 2024
Remarks: ** Back to market and reviewing multiple offers: submit all offers by Monday 5:00 pm 5/25/26** Spacious 3-bedroom, 2-bathroom home in Winter Haven priced to sell! This fixer-upper is perfect for investors, flippers, FHA 203(k) buyers, or first-time homeowners looking to build instant equity. With 2,182 sq ft of living space on an 8,442 sq ft lot, this property offers plenty of room for cosmetic and structural improvements. Priced well below market, buyers can capitalize on a significant value-add opportunity in a growing neighborhood. Renovate to create your dream home, or take advantage of strong resale and rental potential.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Daryl Ash, Ii (863-934-1548)
352 ALEXZANDER WAY, WINTER HAVEN, FL 33881
$269,90075 Days on yellowkey MLS ID: L4960645
REDUCED by $9,100 (3.3%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1867 Built: 2021Monthly Fee: $86 Tax: $4,088 (2024)Community: Jace LndgSingle Family
Taxes:$4,088
Elementary School: Walter Caldwell Elem
Middle School: None
Remarks: 2021 built beautiful house with 4 beds and 2 baths and inside laundry room and double car garage totaling 2395 Sqft under roof. Centrally located in a very nice, quiet community on a dead-end road. Plenty of open air as there is no neighboring house on one side and back of the house. Open floor plan with Master in one side and other three bedrooms are located on the other side of the house. Stainless appliances are in the kitchen with a large spacious island for meal preparation and breakfast. Master bath with his and her walk-in closet with separate door for the toilet. Double sink and standing shower in the master and tub in the other bath. Tiles in all wet areas and waterproof wood like vinyl flooring throughout the living area and bedrooms floor. Dishwasher (not included with this sale) has power but not hooked up with water (buyer will have to try as is or get their own dishwasher). House is AS IS and buyer to verify as seller never lived on this property.
Listing Agent: Mohammad Iqbal (813-494-8864)
2813 WINGFOOT CT, WINTER HAVEN, FL 33884
$215,00099 Days on yellowkey MLS ID: L4959887
1 Days Off yellowkey (back on 6/8/2026)
REDUCED by $15,000 (6.5%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1682 Built: 1990Monthly Fee: $295 Tax: $2,981 (2025)Community: Cypresswood Golf VillasSpa: NoVilla
Taxes:$2,981
Remarks: Under contract-accepting backup offers. Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
256 MEREDITH BLVD, WINTER HAVEN, FL 33881
$339,99046 Days on yellowkey MLS ID: G5111558
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
Elementary School: Lake Alfred Elem
Remarks: One or more photo(s) has been 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)
3097 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$449,0009 Days on yellowkey MLS ID: S5150948
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2577 Built: 2004Monthly Fee: $33 Tax: $4,587 (2025)Community: Buckeye PointeSpa: YesSingle Family
Taxes:$4,587
Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Desiree Carlson (541-743-1985)
1871 EMILY DR, WINTER HAVEN, FL 33884
$312,50029 Days on yellowkey MLS ID: S5149517
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2012 Built: 2005Monthly Fee: $38 Tax: $3,862 (2025)Community: Emily EstatesSingle Family
Taxes:$3,862
Remarks: Beautiful single-family home offering 4 bedrooms and 2 bathrooms with approximately 2,012 square feet of heated living space. This spacious residence features high ceilings and a functional layout designed for comfortable living and entertaining. The kitchen includes space for a breakfast table and flows seamlessly into a separate dining room, while an additional family room provides the perfect setting for gatherings. Conveniently located near Cypresswood Golf & Country Club, East Central Park, and Rotary Park, offering access to outdoor recreation, including skating, softball, and picnic areas. The property also provides easy access to U.S. Highway 27, with shopping, dining, and everyday conveniences just minutes away, including Publix and Walmart. The owner is currently in the process of updating the home, including new flooring and additional improvements, all of which will be completed before closing.
Listing is courtesy of: REALTY OF AMERICA (321-732-5369)
Listing Agent: Cisco Romero (407-922-6375)
1540 N LAKE MIRROR DR NW, WINTER HAVEN, FL 33881
$950,000370 Days on yellowkey MLS ID: P4934907
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3885 Built: 1967 Tax: $6,494 (2025)Community: Mirro MacSingle Family
Taxes:$6,494
Elementary School: Inwood Elem
Middle School: Westwood Middle
Remarks: Lakefront living on the Winter Haven Chain of Lakes takes on a completely different feel at The Guest House, a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
1280 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$1,259,0007 Days on yellowkey MLS ID: L4961525
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5416 Built: 1995 Tax: $7,019 (2025)Community: N/ASingle Family
Taxes:$7,019
Remarks: Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come together in this truly one-of-a-kind estate on the shores of Lake Hamilton. Situated on more than one acre of fully fenced waterfront property with a wrought-iron gated entrance and no HOA restrictions, this custom residence offers over 5,400 square feet of living area designed for both grand entertaining and everyday enjoyment of Florida's lakefront lifestyle. From the moment you arrive, the home's distinctive architectural design makes a lasting impression. A circular driveway leads to the large covered portico where a tranquil fountain welcomes guests and creates an unforgettable arrival experience. Stepping through the double doors reveals a dramatic foyer with soaring ceilings, abundant natural light, and immediate panoramic lake views. Throughout the home, artistic influence and personality are evident at every turn. One of the owners is an accomplished artist, and their creativity is beautifully reflected in the home's unique design elements, decor, and inviting spaces. The completely remodeled kitchen, updated in 2018, serves as the heart of the home and features extensive custom cabinetry, granite countertops, a striking raised glass breakfast bar, center island with a built-in wine trough, and a bright eat-in dining area overlooking the lake. Nearby, the formal dining room provides the perfect initimate setting for holiday gatherings and special occasions. Designed with flexibility in mind, the home offers multiple living and entertaining spaces including a spacious family room anchored by a fireplace, dedicated office, theater room, enclosed Florida room stretching across the rear of the home, and numerous areas for relaxation or hosting guests. The expansive Florida room is the ideal place to begin each day with coffee while watching spectacular sunrises paint the sky over the water. The first floor features three generously sized guest bedrooms, while the private owner's retreat occupies the upper level. This luxurious sanctuary enjoys elevated wraparound views of Lake Hamilton, creating a peaceful escape unlike anything else in the area. Also located above is a unique artist's perch or widow's walk, offering an elevated vantage point to enjoy panoramic views, morning and evening skies, wildlife watching, and endless inspiration. Outdoor living is equally impressive. The heated salt-filtered pool, completed in 2018, overlooks the lake and creates a resort-style atmosphere. Expansive paver decking and wide-open lawn areas provide ample room for family gatherings, pets, and outdoor recreation. A composite dock extends into Lake Hamilton, making it easy to enjoy boating, fishing, paddleboarding, and sunset cruises. Spanning nearly 1,900 acres, Lake Hamilton is widely known for its excellent fishing, boating opportunities, and scenic beauty. Cruise across the lake to enjoy dining and entertainment at local favorites such as Floridino's and Port 27 before returning home for a peaceful sunset ride across the water. Additional features include a detached two-car garage, large storage shed and the privacy and freedom that comes with having no HOA. Rarely does a property combine architectural character, artistic expression, expansive living space, resort-style amenities, and over an acre of lakefront land in such a remarkable setting. This is more than a home—it is a private waterfront retreat where every sunrise feels like a work of art.
47 ENCLAVE DR, WINTER HAVEN, FL 33884
$245,000105 Days on yellowkey MLS ID: P4937867
REDUCED by $15,000 (5.8%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 1999Monthly Fee: $433 Tax: $3,221 (2025)Community: Cypresswood Enclave Ph 2Spa: NoVilla
Taxes:$3,221
Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!
Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)
Listing Agent: David Shippey (863-521-4517)
271 INMAN BLVD, WINTER HAVEN, FL 33881
$350,000187 Days on yellowkey MLS ID: W7881213
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2274 Built: 2024Monthly Fee: $49 Tax: $1,347 (2024)Community: Inman GrovesSpa: NoSingle Family
Taxes:$1,347
Remarks: PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)
Listing Agent: Isabelle Maye (540-840-8849)
2235 LAKERIDGE DR, WINTER HAVEN, FL 33881
$305,00061 Days on yellowkey MLS ID: P4938412
REDUCED by $10,000 (3.2%) on 05/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1893 Built: 2015Monthly Fee: $65 Tax: $2,614 (2025)Community: Lakeridge EstatesSingle Family
Taxes:$2,614
Remarks: Welcome to 2235 Lakeridge Estates, your opportunity to enjoy the Florida lifestyle in one of Winter Haven's growing and desirable communities near scenic Lake Hartridge and the Beautiful Winter Haven Chain of Lakes. An exceptional opportunity to own a beautifully designed home in the heart of Winter Haven. Nestled within the desirable Lakeridge Estates community near scenic Lake Hartridge, this well-maintained 3-bedroom, 2-bathroom residence offers nearly 1,893 square feet of thoughtfully designed living space, blending comfort, functionality, and Florida lifestyle appeal. From the moment you arrive, you’re greeted by a welcoming entry that opens into a bright, open-concept floor plan featuring vaulted ceilings and a seamless flow between the living and dining areas—perfect for both everyday living and entertaining. The spacious kitchen is a standout, complete with stainless steel appliances, ample cabinetry, a center island, and a pantry, making it as practical as it is stylish. The split-bedroom layout offers privacy and comfort, with a generously sized primary suite featuring a walk-in closet and an en-suite bath with dual features designed for relaxation. Two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to one of this home’s most desirable features—a spacious backyard, ideal for outdoor gatherings, pets, or creating your own private oasis. The covered rear porch extends your living space outdoors, capturing the essence of Florida indoor-outdoor living. Location is key, and this home delivers. You’re just minutes from everyday conveniences including shopping destinations, along with casual dining options. Beyond daily conveniences, Winter Haven is known for its vibrant charm and attractions. Enjoy weekends exploring the nearby Chain of Lakes, or take a short drive to world-renowned destinations like LEGOLAND Florida Resort, a major area highlight for entertainment and recreation. The revitalized downtown district offers local boutiques, dining, and community events, adding to the area’s growing appeal. Whether you’re a first-time buyer, growing household, or investor, 2235 Lakeridge Drive presents a compelling blend of space, location, and lifestyle—an inviting place to call home in one of Central Florida’s most steadily growing markets.
Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)
Listing Agent: Maria Elena Fernandez (407-704-0732)
2085 ISLE ROYALE CT SE #284, WINTER HAVEN, FL 33880
$124,999122 Days on yellowkey MLS ID: O6380383
REDUCED by $1 (0.0%) on 04/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 648 Built: 2004Monthly Fee: $270 Tax: $213 (2025)Community: Park LakeCondo
Taxes:$213
Elementary School: John Snively Elem
Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner.
Listing is courtesy of: LIONHEART BROKERS (321-214-4640)
Listing Agent: Claudia Centesimo (407-383-8882)
373 LAKE DAISY CIR, WINTER HAVEN, FL 33884
$215,000187 Days on yellowkey MLS ID: L4957732
1 Days Off yellowkey (back on 6/6/2026)
REDUCED by $10,000 (4.4%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1391 Built: 1990 Tax: $3,356 (2025)Community: Lake Daisy EstatesSpa: NoSingle Family
Taxes:$3,356
Remarks: Under contract-accepting backup offers. MOTIVATED SELLERS...OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Cheryl Brewer (863-224-0045)
108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881
$425,000189 Days on yellowkey MLS ID: L4957549
REDUCED by $14,000 (3.2%) on 04/13/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2495 Built: 1996Monthly Fee: $85 Tax: $3,479 (2025)Community: Gates Of Lake RegionSingle Family
Taxes:$3,479
Remarks: Located within the highly desirable gated community of The Gates of Lake Region, this beautifully maintained neighborhood is known for its picturesque brick-walled entrance, lush mature landscaping, tranquil ponds with fountains, and pride of ownership throughout. Unlike larger developments, The Gates of Lake Region offers a warm, neighborly atmosphere where residents enjoy quiet streets, manicured lawns, quality-built homes, and a true sense of community. This spacious 2,500-square-foot residence was originally constructed as a builder's model home and showcases numerous upgrades and architectural details throughout. Built with high-efficiency Ytong concrete block construction, the home offers superior sound reduction, enhanced structural performance, and meaningful energy savings. The elegant floor plan features 4 spacious bedrooms (one currently utilized as an office), 2 full bathrooms, and 1 half bath. Refined interior finishes include crown molding, oversized custom doors, handcrafted double entry doors, custom cabinetry, ceiling fans, a jetted tub in the primary suite, and a generously sized laundry room. Mature landscaping and a covered front entry create an inviting first impression. Inside, the foyer opens to formal living and dining areas accented by soaring ceilings and detailed trim work, providing an elegant setting for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, solid-surface countertops, a closet pantry, and a bright breakfast nook overlooking the screened lanai and private brick-walled backyard. The comfortable family room is centered around a granite-faced gas fireplace that adds warmth and character. A desirable split-bedroom layout provides privacy for the primary suite, which features a spacious walk-in closet, soaking tub, and tiled walk-in shower. The guest wing includes two additional bedrooms with generous closet space and convenient access to the guest bath. Outdoor living is equally inviting with a large screened lanai, mature tropical landscaping, and a private brick-walled backyard designed for relaxation and enjoyment. Additional features include an oversized two-car garage, natural gas water heater, irrigation system, and an efficient interior laundry room with additional storage. Residents of The Gates of Lake Region enjoy a peaceful setting surrounded by scenic ponds, decorative fountains, and beautifully maintained common areas, all while being just minutes from the Winter Haven Chain of Lakes, several golf courses, the Country Club of Winter Haven, medical facilities, shopping, dining, and Downtown Winter Haven. A new Publix is also planned nearby for added convenience. Orlando, Tampa, international airports, and both Florida coasts are all within easy driving distance. If you're searching for a community that combines timeless charm, quality homes, beautiful surroundings, and a genuine neighborhood feel, The Gates of Lake Region is a place you'll be proud to call home.
900 AVENUE Z SE #A1, WINTER HAVEN, FL 33880
$135,00031 Days on yellowkey MLS ID: L4961664
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 840 Built: 1974 Tax: $1,582 (2025)Community: Sandy Cove Winter HavenCondo
Taxes:$1,582
Remarks: Condo located in Winter Haven FL, the Water Ski Capital of the World and only 6 minutes from Legoland! Ground-floor, furnished condo in Sandy Cove, a lakefront community on the beautiful Winter Haven Chain of Lakes. This furnished 2-bedroom, 1-bath unit offers low-maintenance living that’s ideal for full-time residents, seasonal owners, retirees, or anyone seeking a convenient Florida lifestyle. The layout offers comfortable living with a spacious great room featuring laminate flooring, a ceiling fan, and sliding doors leading to the enclosed Florida room. The adjacent dining space is cozy and ideal for entertaining or quiet nights in. The kitchen is complete with quartz countertops, included appliances, and a stackable washer and dryer. The unit also features double-pane windows for improved energy efficiency, comfort, and noise reduction. The primary bedroom is generously sized and features a ceiling fan, walk-in closet, and direct access to the bathroom. The guest bedroom is also comfortably sized with a built-in closet, ceiling fan, and en-suite-style bathroom access. The bathroom has been updated with an upgraded vanity, solid-surface countertop, and walk-in shower. Enjoy outdoor living from the enclosed Florida room with screens and vinyl windows, perfect for relaxing or entertaining year-round. This ground-floor unit is ideally positioned just steps from the community clubhouse, grill area, and heated pool maintained at approximately 85 degrees for year-round enjoyment. Sandy Cove also offers a community dock on Lake Lulu, one of twenty+ lakes on the Winter Haven Chain, providing a peaceful setting to unwind, enjoy waterfront views, and take in beautiful Florida sunsets. Residents enjoy the relaxed lifestyle that makes Winter Haven so desirable, including boating, fishing, lakeside dining, golf courses, walking paths, and year-round community events. Conveniently located near everyday essentials and recreation, the condo is just minutes from Publix Super Markets, CVS Pharmacy, restaurants, banks, medical offices, and Walmart shopping. Nearby public boat access on Lake Summit makes it easy to enjoy the Chain of Lakes lifestyle, while several local golf courses are only a short drive away. The location also provides convenient access to both Orlando and ,making this an excellent choice for easy, low-maintenance Central Florida living.
3742 FIELDSTONE CIR, WINTER HAVEN, FL 33881
$300,0005 Days on yellowkey MLS ID: L4962401
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2016Monthly Fee: $36 Tax: $4,631 (2025)Community: Country Club EstatesSingle Family
Taxes:$4,631
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,919 square feet of comfortable living space in the well-kept community of Country Club Estates of Winter Haven. Lovingly cared for as a second home, this residence shows pride of ownership throughout and is truly move-in ready. The spacious floor plan provides plenty of room for everyday living and entertaining, while the extended screened rear patio creates the perfect setting to relax, enjoy your morning coffee, or unwind after a long day while taking in the peaceful surroundings. One of the property's most desirable features is its private backyard setting with no rear neighbors. The vacant parcel directly behind the home is designated for drainage and retention and is not slated for future development, providing added privacy and open views (buyer to verify with Polk County). Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this well-kept home offers comfort, privacy, and a fantastic Winter Haven location. Don't miss your opportunity to make it yours today!
Listing Agent: Brandy Duncan (863-585-6849)
4111 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$399,90014 Days on yellowkey MLS ID: O6411190
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1998 Built: 2012Monthly Fee: $17 Tax: $4,556 (2025)Community: Island LakesSingle Family
Taxes:$4,556
Remarks: Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!
Listing Agent: Amy Moline (407-506-7447)
381 WINTER RIDGE BLVD, WINTER HAVEN, FL 33881
$143,000154 Days on yellowkey MLS ID: S5140657
REDUCED by $2,500 (1.7%) on 05/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1996Monthly Fee: $253 Tax: $2,125 (2025)Community: Winter Ridge CondoCondo
Taxes:$2,125
Elementary School: Fred G. Garnier Elem
Middle School: Lake Alfred-Addair Middle
Remarks: One or more photo(s) has been virtually staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
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