Location: Winter Haven
Do Not Show Listings
3826 GAINES CT, WINTER HAVEN, FL 33884
$1,779,90074 Days on yellowkey MLS ID: P4937567
0 Days Off yellowkey (back on 4/3/2026)
Bed: 6 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5400 Built: 1989Monthly Fee: $44 Tax: $14,471 (2025)Community: Gaines CoveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,471
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Property is under contract with contingencies and a kick-out clause. Seller will consider backup offers. Lakefront home on the prestigious Chain of Lakes, directly on Lake Eloise, set on 1.87 acres. This three-story estate offers 6 bedrooms, 5.5 bathrooms, and a private in-law suite on the lower level, providing exceptional privacy, generous scale, and a setting designed to embrace the lake. The primary suite is thoughtfully positioned to capture sweeping lake views and serves as a true retreat, featuring a large walk-in closet and a spa-style bath with oversized shower and jacuzzi tub. Additional living spaces flow effortlessly, anchored by a chef’s kitchen with granite countertops, cherry cabinetry, and double ovens, opening to both formal and casual gathering areas ideal for entertaining. Designed for elevated living and hosting, the home includes a private movie room for a true theater experience and a spacious game and gathering room located just off the pool, creating a seamless indoor-outdoor connection. Outdoor living is a focal point of the property, highlighted by a large infinity pool within a screened enclosure overlooking the lake—an ideal setting for entertaining, relaxing, and enjoying sunset views. A private boat dock extends the lakefront lifestyle. Additional highlights include a grand circular driveway, mature shade trees, a four-car garage with space for recreational vehicles, a whole-home Generac system, and low HOA.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Daniela Zoppe (407-808-7350)
6204 KNOTTY PINE DR SE, WINTER HAVEN, FL 33884
$120,000281 Days on yellowkey MLS ID: P4935440
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1014 Built: 1985Monthly Fee: $65 Tax: $696 (2024)Community: Garden Grove OaksManufactured Home
Taxes:$696
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: Under contract-accepting backup offers. R E D U C E D - R E D U C E D ... DON'T WAIT TO OWN THIS 2BR-2BA MFG HOME ON THIS LARGE CORNER LOT IN SE COMMUNITY WITH LOW MONTHLY FEES, OWNING YOUR OWN LAND AND GREAT AMENITIES. CLUBHOUSE WITH LARGE ENTERTAINMENT ROOM, FULL KITCHEN, LIBRARY, BILLIARDS ROOM, SPA, OVERSIZED POOL OVERLOOKING WATERFRONT PEACE POND WITH COOKOUT ROOM OFF POOL AREA AND EVEN SHUFFLEBOARD, THIS COMMUNITY OFFERS SO MUCH FOR THEIR RESIDENTS. THE HOME IS MOVE IN READY AND HAS SOME FURNITURE LEFT FOR CONVENIENCE OF THE SELLER. OPEN LIVING ROOM DESIGN WITH SEPARATE DINING ROOM, LARGE KITCHEN HAS EAT IN COUNTER , SPLIT BEDROOM PLAN WITH 2 BATHS. PRIMARY BEDROOM AND BATH HAS STEP IN SHOWER AND GUEST BATH OFF 2ND BR HAS TUB. LAUNDRY ROOM WITH WASHER, DRYER & WORKSHOP WALL OFF THE 14X8 SCREEN ENCLOSED PORCH. 18X11 CARPORT WITH LONG DRIVEWAY WITH PLENTY OF PARKING SPACE FOR VISITING GUESTS. MATURE LANDSCAPING WITH 2 LARGE OAKS ON THIS CORNER LOT.
Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)
Listing Agent: Glenda Pruitt (863-412-2727)
260 GREENFIELD RD, WINTER HAVEN, FL 33884
$393,00064 Days on yellowkey MLS ID: P4937787
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1947 Built: 1978Monthly Fee: $152 Tax: $5,885 (2025)Community: Cypresswood Greenfield VillageSingle Family
Taxes:$5,885
Elementary School: Elbert Elem
Remarks: Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours. AGENTS, please see remarks.
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
688 AUGUSTA RD, WINTER HAVEN, FL 33884
$337,00049 Days on yellowkey MLS ID: P4937966
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1586 Built: 1980Monthly Fee: $137 Tax: $3,636 (2025)Community: Cypresswood Fairway Patio HomesSingle Family
Taxes:$3,636
Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!
2336 W CANNON TER NW, WINTER HAVEN, FL 33881
$729,00092 Days on yellowkey MLS ID: L4958323
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1856 Built: 1995 Tax: $6,634 (2025)Community: West Cannon TerraceSingle Family
Taxes:$6,634
Remarks: HUGE PRICE DROP! Completely renovated home with new pool on Cannon Lake! Welcome to your dream lakeside retreat on a sprawling lot with 120 feet of pristine lakefront on Lake Cannon. This completely renovated three-bedroom, two-bathroom home boasts an open floor plan with high ceilings and a desirable split-bedroom layout. The stunning kitchen features granite countertops, a counter-height breakfast bar, and brand-new Samsung bespoke appliances, including an induction stove, perfect for culinary enthusiasts. The expansive primary suite offers a luxurious en suite bath with a large shower equipped with multiple showerheads, including a rain showerhead, and sliding glass doors that lead to an impressive outdoor entertaining space. The screened-in patio, perfect for hosting gatherings, overlooks the brand-new saltwater, heated pool and spa, completed in 2025, creating an idyllic setting for relaxation and fun. Additionally, the home features a new roof and new windows, ensuring peace of mind for years to come. Enjoy unobstructed views of the lake from your large outdoor area, ideal for summer barbecues or evening stargazing. Conveniently located near shopping, restaurants, and entertainment, this home truly offers the best of lakeside living on the chain of lakes.
Listing Agent: David Small (407-601-8351)
1864 EMILY DR, WINTER HAVEN, FL 33884
$297,000154 Days on yellowkey MLS ID: TB8447490
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1836 Built: 2005Monthly Fee: $25 Tax: $3,788 (2024)Community: Emily EstatesSingle Family
Taxes:$3,788
Remarks: Come to see this move-in-ready, 4-bedroom 2-bath home located in the Beautiful Community of Emily Estates!! Featuring shiny new stainless steel appliances, fresh interior and exterior paint, and brand new plumbing fixtures, this home feels like it was just built! You will love everything about this house, but especially its light and bright floorplan, showering sunlight on the wide open living areas, a kitchen with plenty of cabinet and counter space, and a breakfast bar, ceramic tile throughout for easy maintenance, a beautiful backyard with tons of room to run and play or relax and soak up some sun. Located in a great neighborhood close to shopping, dining, and right down the road from Legoland!
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Octavia Cheveresan (727-403-8948)
345 24TH ST NW #25, WINTER HAVEN, FL 33880
$158,00069 Days on yellowkey MLS ID: P4937740
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1979Monthly Fee: $270 Tax: $1,776 (2025)Community: Imperial VillasVilla
Taxes:$1,776
Remarks: Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open layout flows seamlessly to a peaceful sitting lanai overlooking the heated community pool—the perfect spot to enjoy your morning coffee or unwind in the evenings. Major updates add peace of mind, including a resurfaced roof with a 15-year warranty, a tankless hot water heater, and an updated electrical system. The low HOA fee of just $270/month covers water, high-speed internet, cable, gas, and all grounds maintenance—you only pay for electric! The property includes 2 assigned parking spaces, with one under a carport, and the community has ample visitor parking. Enjoy easy access to shopping, dining, and downtown Winter Haven events, all while embracing a relaxed, low-maintenance lifestyle close to the lake. Whether you’re downsizing, snowbirding, or looking for carefree Florida living, this villa checks all the boxes. Property is eligible for FHA Financing! Move in, relax, and enjoy the best of Winter Haven living!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Michele Elchin (863-514-6880)
333 LAKE HOWARD DR NW #113D, WINTER HAVEN, FL 33880
$112,00018 Days on yellowkey MLS ID: P4938082
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1030 Built: 1974 Tax: $1,073 (2025)Community: Imperial Harboursphases 01 & 02Condo
Taxes:$1,073
Remarks: Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.
Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)
Listing Agent: Nancy Cini (727-612-0375)
2800 SUNSET DR NW, WINTER HAVEN, FL 33881
$349,000300 Days on yellowkey MLS ID: P4935252
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 1972 Tax: $1,432 (2024)Community: Idylwild HeightsSingle Family
Taxes:$1,432
Elementary School: Walter Caldwell Elem
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing blend of suburban tranquility and convenient urban access.
Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)
Listing Agent: Lucy Martinez (863-521-4156)
4749 MAGNOLIA PRESERVE AVE, WINTER HAVEN, FL 33880
$299,90022 Days on yellowkey MLS ID: O6393069
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2015Monthly Fee: $32 Tax: $2,273 (2025)Community: Magnolia Preserve Phase TwoSingle Family
Taxes:$2,273
Elementary School: Eagle Lake Elem
High School: Lake Region High
Remarks: Under contract-accepting backup offers. Beautiful 4-bedroom, 2-bath home in Magnolia Preserve with an open-concept layout, high ceilings, and a large backyard overlooking a pond with a fountain. The spacious great room features wood-look flooring, recessed lighting, and a ceiling fan, while the kitchen offers a large breakfast bar, ample cabinetry, stainless steel appliances, and generous counter space. The primary suite includes a walk-in closet and an en-suite bath with dual sinks, garden tub, and separate shower. Enjoy the covered rear patio, interior laundry room, and 2-car garage. Move-in ready and conveniently located near shopping, dining, and major roadways.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Jeremy Harper, Pa (863-288-0886)
638 LAKE DEXTER CIR, WINTER HAVEN, FL 33884
$244,90030 Days on yellowkey MLS ID: O6390069
REDUCED by $5,000 (2.0%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1989Monthly Fee: $35 Tax: $3,649 (2025)Community: Lake Dexter Woods Ph 02Single Family
Taxes:$3,649
Elementary School: Chain O Lakes Elem
Remarks: This move-in-ready, three-bedroom, two-bathroom home is located in the sought-after Lake Dexter Woods community. The residence features a functional layout designed for modern comfort and style, highlighted by an attached one-car garage and low-maintenance tile flooring throughout the entire home. The updated kitchen serves as a stylish centerpiece, equipped with beautiful granite countertops and sleek stainless-steel appliances. Outside, you can relax and enjoy the fresh air from your private porch and patio, which overlooks a fully fenced-in backyard, providing a secure space for outdoor entertaining or pets. The location offers a perfect blend of comfort and convenience, situated near top-rated schools, multiple grocery stores, and popular local attractions. Residents can enjoy a resort-style lifestyle with access to premium community amenities, including sparkling pools, tennis/pickleball courts, and more.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
214 GROVE RIDGE DR, WINTER HAVEN, FL 33880
$280,00060 Days on yellowkey MLS ID: O6382247
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1560 Built: 2019 Tax: $1,536 (2025)Community: Grove RidgeManufactured Home
Taxes:$1,536
Remarks: Under contract-accepting backup offers. Back on market, buyer financing fell through. Their loss, your gain! Stunning ranch modern transformation that will take your breath away! Welcome to this 2019 impeccably redesigned modern rustic 4 bed/2 bath retreat on fenced one-third acre lot on cul-de-sac with seamless indoor-outdoor entertaining. Homeownership pride from the front curb to the back fence! As you approach, you are greeted by a New sprawling 13’x46’ covered front porch with ample space for hosting gatherings while you enjoy the beautifully landscaped front yard with extended driveway that includes a tall RV cover. Step inside to the farmhouse chic living room that seamlessly flows through the sliding barn doors into the heart of the home, the custom designed kitchen, featuring wood beam tray ceiling with pendent lighting, white cabinets, butcher block counter, SS appliances including smart fridge w/tv & Alexa, large island with farm sink and breakfast bar, & barn door pantry with luxury vinyl plank flooring throughout and fresh interior paint. Adjacent to the kitchen on one side is the laundry room with built in cabinets that leads to the back yard, and the other side to the spacious family room, with every inch thoughtfully styled that create a warm, inviting atmosphere. Included is the entertainment center with the wide screen tv. The main bedroom has spacious on-suite bathroom that features beadboard panels & stone backsplash, dark matching accent trim, double sinks, garden tub, separate rain head shower with glass sliding door, and storage closet. The 2, 3 ,& 4th bedroom share a convenient 2nd bathroom with shower/tub. The property also includes a large storage shed with electric— perfect for tools, hobbies, or extra storage. Situated in a peaceful area of Winter Haven, this home offers the best of both worlds: quiet suburban living with easy access to shopping, dining, and major highways for commuting throughout Central Florida. Don’t miss your chance to own this move-in-ready home with modern updates, generous space, and outdoor charm — all with no HOA!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Sheryl Manche (386-882-2121)
205 WESTWOOD AVE, WINTER HAVEN, FL 33880
$210,00033 Days on yellowkey MLS ID: TB8485945
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 806 Built: 2021 Tax: $2,703 (2025)Community: Brysons R H SubSingle Family
Taxes:$2,703
Elementary School: Frank E. Brigham Academy
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Charming 2-bedroom, 1.5-bath home located in Winter Haven presenting a great opportunity for first-time home buyers or investors. This property features a functional layout with comfortable living spaces and a practical design suited for everyday living. The home sits on a generously sized lot, providing plenty of outdoor space for entertaining, gardening, or future improvements. Conveniently located near local schools, shopping, dining, and major roadways, this property provides both accessibility and convenience. With strong potential as a starter home, rental property, or investment opportunity, this home is a great option for buyers looking to enter the market or expand their portfolio in the growing Winter Haven area.
Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)
Listing Agent: Jay Patel (863-399-5820)
6036 NAVONA WAY, WINTER HAVEN, FL 33884
$304,999202 Days on yellowkey MLS ID: TB8431493
1 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2039 Built: 2025Monthly Fee: $18 Tax: $8,495 (2025)Community: Villa MarSingle Family
Taxes:$8,495
Elementary School: Pinewood Elem
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. Did we mention the brand-new washer and dryer? The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Contact or make an appointment for more details on interest rates. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
5480 SAN PIETRO DR, WINTER HAVEN, FL 33884
$378,120246 Days on yellowkey MLS ID: TB8416862
58 Days Off yellowkey (back on 3/12/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 2025Monthly Fee: $18 Tax: $2,768 (2025)Community: Villa MarSingle Family
Taxes:$2,768
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Meet the Esperanza, a single-story, multi-generational home designed for modern living with flexibility and comfort. This 4-bedroom, 3-bathroom, 2-car garage home features a separate multi-gen suite with its own bathroom and kitchenette, ideal for extended family or guests. The spacious layout offers distinct areas for gathering and relaxing, including an open-concept living and dining space paired with a thoughtfully designed kitchen featuring quartz countertops, stainless steel appliances, and smart home technology for everyday convenience. With smart design and stylish touches throughout, the Esperanza balances independence and togetherness, providing room to grow—together. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.
3324 FOX RIDGE DR, WINTER HAVEN, FL 33884
$275,00021 Days on yellowkey MLS ID: TB8490277
1 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1422 Built: 1985 Tax: $3,619 (2025)Community: Fox Ridge Ph 01Single Family
Taxes:$3,619
Remarks: Under contract-accepting backup offers. Nestled within the peaceful community of Fox Ridge, this exquisite 3-bedroom, 2-bathroom home serves as a sanctuary for those in search of tranquility combined with modern amenities. As you step inside, you'll be greeted by bright, fresh interiors enhanced by newly installed luxury vinyl plank flooring throughout the main living areas. The kitchen, a chef's delight, features stainless steel appliances, sleek white cabinets, and elegant granite countertops. The generous primary suite includes dual closets and a convenient ensuite bathroom for added comfort. An expansive sunroom beckons you to unwind throughout the year, while the private, fenced-in backyard is ideal for gatherings or enjoying a peaceful afternoon. This home also features a new ROOF, a new HVAC system, a two-car garage, and updated lighting and fixtures throughout, ensuring it's move-in ready. Don’t miss the chance to explore this charming retreat today!
Listing is courtesy of: URBAN CORE REALTY (813-418-0207)
Listing Agent: Monica Dudas (813-418-0207)
6617 WESTCHESTER DR NE, WINTER HAVEN, FL 33881
$135,00019 Days on yellowkey MLS ID: S5146646
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1987Monthly Fee: $46 Tax: $1,848 (2025)Community: Lake N Golf Estates AddManufactured Home
Taxes:$1,848
Remarks: Welcome to 6617 Westchester Dr NE in Winter Haven, located in the highly desirable 55+ no pet community of Lake 'n Golf Estates. This spacious and well maintained home has been lovingly owned by the same family since 1992 and offers comfort, convenience, and a true Florida lifestyle. Inside, you’ll find a bright and inviting layout with generous living spaces, engineered wood flooring in the main living areas and bedrooms, and porcelain tiles in the kitchen, bathrooms, and hallway. The home also features an inside laundry room for added ease. It will be sold mostly furnished, making it a perfect move in ready option for seasonal or full time living. A standout feature is the enclosed front Florida room, complete with its own mini/split system for heating and cooling, along with updated windows, blinds, porcelain flooring, a ceiling fan, and a hide-a-bed, creating a comfortable and versatile bonus space year round. This home has been thoughtfully updated over time, including a new roof (2023), updated heat pump and ductwork, a membrane roof over the sunroom and new siding (2025). Additional improvements include updated windows and doors, enhanced plumbing throughout (including replacement of gray piping, water heater, fixtures, and disposal) and upgraded appliances such as a new stove (2025) and microwave (2024). Outside, you’ll appreciate the large carport, a beautifully finished driveway, and additional space for golf cart parking, along with a cement golf cart path for added convenience. With NO REAR neighbors, the property offers a private and peaceful setting. Additional included items such as select furnishings, a leather recliner, beds, TVs, ceiling fans, blinds, and an outside antenna add even more value and convenience. Residents of Lake 'n Golf Estates enjoy a vibrant and active lifestyle with access to lake Henry, a clubhouse, pool, shuffleboard courts, and a variety of social activities. Conveniently located near shopping, dining, and everyday amenities, this community offers both relaxation and accessibility. Don’t miss your opportunity to own a beautifully updated and spacious home in one of Winter Haven’s most welcoming 55+ communities, schedule your private showing today!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
400 EL CAMINO DR #223, WINTER HAVEN, FL 33884
$59,900162 Days on yellowkey MLS ID: O6354793
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 850 Built: 1974 Tax: $945 (2023)Community: Orchid Spgs Vill 400 San MiguelCondo
Taxes:$945
Tax Year: 2023
Remarks: Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical facilities, Winter Haven Hospital, US Hwy 27, and I-4. The monthly HOA fee covers water, sewer, trash, natural gas, lawn maintenance, grounds upkeep, and use of the community room, allowing for easy, maintenance-free living. An assigned parking space is included, and one pet is welcome with HOA approval (size and breed restrictions apply). Buyer approval is also required by the HOA. Whether you’re searching for a year-round home or a seasonal retreat, this well-maintained condo at Orchid Springs Village offers comfort, convenience, and a welcoming community atmosphere.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Scott Cohara (407-398-9554)
1546 JESSICA BLVD, WINTER HAVEN, FL 33884
$275,490181 Days on yellowkey MLS ID: O6353135
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1880 Built: 2025Monthly Fee: $14 Tax: $32 (2024)Community: Peace Creek Reserve 40'SSingle Family
Taxes:$32
Elementary School: Wahneta Elem
Remarks: One or more photo(s) has been virtually staged. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
6033 GRAND OAKS DR SE, WINTER HAVEN, FL 33884
$140,000164 Days on yellowkey MLS ID: P4936903
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1982Monthly Fee: $65 Tax: $1,784 (2024)Community: Garden Grove OaksManufactured Home
Taxes:$1,784
Remarks: Very well kept home on your own lot. No lot rent here! Low HOA of only $65 a month. Garden Grove Oaks is a well-kept and managed over 55 park in a great location in SE Winter Haven. Home has 2 bedrooms and 2 full bathrooms. Kitchen and dining area have tons of cabinets and storage for all your dishes and cookware and includes a closet pantry. There is a wet bar in the dining area with a small sink, open shelves and cabinet storage underneath. The opposite side of the dining room has a built-in china cabinet. Main bedroom is a great size with a walk-in closet and small bathroom with tub and tiled shower. Second bedroom has door opening to nice-sized bathroom with large sink and cabinets and a shower/tub combination. Home has a membrane roof that was installed in spring of 2014. York air conditioner is 8-9 years old. Nice large laundry room has Bosch washer and dryer. Back screened porch is always cool! HOA fee includes use of the clubhouse with many activities planned every month. There is a billiard room, card and game room with library and puzzles to check out, large event area, and great kitchen. Huge heated pool and spa for all residents and their guests. There is also a shuffleboard court. HOA is an award-winning association. Community is close to a Super Walmart and grocery stores as well as shopping and restaurants. Only minutes to Hwy. 27! Winter Haven is famous for its Chain of Lakes! Where else can you find all of this for only $140,000? Please make an appointment to see this great home today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Peggy Lewellen (863-412-7692)
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