Location: Winter Haven , 33884
Do Not Show Listings
116 MANDOLIN DR, WINTER HAVEN, FL 33884
$365,00037 Days on yellowkey MLS ID: O6403313
REDUCED by $5,000 (1.4%) on 05/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2248 Built: 2009Monthly Fee: $56 Tax: $5,678 (2025)Community: MandolinSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,678
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
Remarks: ARE YOU LOOKING FOR A GATED COMMUNITY WITH A LOW HOA and NO CDD? At 116 Mandolin Dr in WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home offers 2,248 square feet of COMFORTABLE LIVING on a generous 0.26-acre lot! Step inside to soaring VAULTED CEILINGS in the living and dining areas—these ELEVATED CEILINGS create an open, airy feel that makes the home even larger than its footprint. The entire home features durable VINYL FLOORING, and all bedrooms are generously sized, offering FLEXIBILITY FOR FAMILIES, guests, or a home office. NATURAL LIGHT pours in throughout the home, creating a bright and welcoming atmosphere that’s perfect for new homeowners. Major updates include a NEW A/C SYSTEM (2025) and GUTTERS INSTALLED (2024), while the WATER HEATER was replaced in 2017. The roof and plumbing are original, but the seller is willing to NEGOTIATE A BRAND NEW ROOF — making this property an UNBEATABLE VALUE for the price. Situated in a quiet gated community, this property offers both privacy and security. The location is a standout—just a short walk from a newly constructed Publix set to open in the coming months, as well as nearby Dollar General and 7-Eleven for everyday convenience. You’re also just minutes away by car from Eagle Ridge Mall, LEGOLAND Florida Resort, and all the shopping, dining, and entertainment that downtown Winter Haven has! —making this home not only comfortable, but perfectly located.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nomar Rosa (646-673-3900)
5351 MICKEY AVE, WINTER HAVEN, FL 33884
$308,950197 Days on yellowkey MLS ID: S5138935
INCREASED by $8,951 (3.0%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
5147 KINSLEY DR, WINTER HAVEN, FL 33884
$299,999373 Days on yellowkey MLS ID: S5127810
REDUCED by $23,636 (7.3%) on 05/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
634 WEXFORD CT, WINTER HAVEN, FL 33884
$235,00018 Days on yellowkey MLS ID: L4961955
0 Days Off yellowkey (back on 6/3/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1328 Built: 1980Monthly Fee: $130 Tax: $1,723 (2025)Community: Cypresswood Patio HomesSingle Family
Taxes:$1,723
Remarks: MOVE-IN CONDITION! Charming 2-bedroom, 2-bath patio home on a shaded, landscaped corner lot in Cypresswood Golf & Country Club. This well-maintained single-level residence features a split-bedroom floorplan, expansive great room for living and dining, breakfast nook, carpet and tile floors, skylight, ceiling fans, ample closets including a walk-in in the primary, and a convenient attached 2-car garage with attic access. Enjoy an oversized screened rear porch overlooking picturesque greenspace and mature oaks. Systems and amenities include architectural shingle roof, gas water heater, and full kitchen appliances (dishwasher, range, microwave, refrigerator, washer/dryer). HOA includes community pool and private road; community amenities include an 18-hole golf course, clubhouse with pro shop and lounge, Jr. Olympic pool, tennis/pickleball/recreation area. Convenient to HWY 27, I-4, shopping, restaurants and near Publix.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Michelle Howard (863-944-9920)
2817 WINGFOOT CT, WINTER HAVEN, FL 33884
$270,000301 Days on yellowkey MLS ID: P4935798
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1666 Built: 1990Monthly Fee: $285 Tax: $1,448 (2024)Community: Cypresswood Golf Villas Gc-2Spa: NoVilla
Taxes:$1,448
Remarks: Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
441 SAN JOSE DR, WINTER HAVEN, FL 33884
$275,000392 Days on yellowkey MLS ID: P4934776
REDUCED by $10,000 (3.5%) on 04/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1843 Built: 1984Monthly Fee: $5 Tax: $1,000 (2024)Community: Orchid Springs Patio HomesSpa: NoSingle Family
Taxes:$1,000
Remarks: Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene & secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exteri9or features; Paved drive and walkways, attractive canopies and covered front porch invites you inside to discover a charming home. The kitchen boasts custom pantry space, ample counter area & is thoughtfully designed for hosting guests without compromising meal preparation. Beyond the kitchen, the spacious living room, flex apace is adjacent to a second private patio. The large family room offers expansive sliding doors and windows making the perfect space for relaxation. Leading to a beautiful lanai ideal for sharing a glass of wine or enjoying a barbeque, with its scenic outlook. The dining room is designed for casual or formal entertainment. The master bedroom features an ensuite bath and picturesque views while additional bedrooms and guest bathroom complete the layout. Flooring; Tiled foyer, kitchen and bathrooms with plush carpet in the master bedroom as well as the second bedroom, living and dining rooms. Designed with single level living in mind this Orchid Springs Patio Home offers ease of mobility and low maintenance. Stop outside to the spacious outdoor area enveloped by lush trees providing privacy and a natural ambiance. Additional amenities include a spacious 2 car garage with natural gas water heater & washer & dryer. Roof will be replaced before closing. Conveniently located in SE Winter Haven, this central Florida home provides easy access to downtown, Chain of Lakes boat launches, LegoLand, and major highways. The neighborhood also features a community clubhouse and pool, enhancing the overall Florida lifestyle experience.
665 BROADMOOR CIR, WINTER HAVEN, FL 33884
$170,00050 Days on yellowkey MLS ID: TB8496998
REDUCED by $10,000 (5.6%) on 06/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1139 Built: 1981Monthly Fee: $335 Tax: $1,395 (2025)Community: Cypresswood Tennis VillasVilla
Taxes:$1,395
Remarks: Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully designed living space. With a mostly furnished interior and quick occupancy available, you can step right in and start enjoying it from day one. Located inside the gated CypressWood golf community, this home delivers true resort-style living. Spend your days enjoying the sparkling pool, tennis courts, and scenic golf course surroundings, all while the HOA takes care of lawn maintenance and exterior upkeep so you don’t have to. The location ties it all together. Just minutes from LEGOLAND Florida Resort, shopping, and dining, with quick access to Highway 27 and I-4, you’re perfectly positioned between Orlando and Tampa for work, travel, or a day out. Whether you’re looking for a full-time home or a seasonal escape, this is low-maintenance Florida living done right.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Darin Dobson (407-947-6773)
4577 BACK NINE DR, WINTER HAVEN, FL 33884
$349,600151 Days on yellowkey MLS ID: P4937386
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1918 Built: 2009Monthly Fee: $5 Tax: $5,155 (2025)Community: Lake Ashton West Ph 01Spa: NoSingle Family
Taxes:$5,155
Remarks: Welcome Home!!! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retirement 55+ community. This home has BRAND NEW EXTERIOR PAINT! The widened, paver driveway offers extra room for parking and the screened entry at the front door is an added bonus. The glass leaded front door with large eye brow window above leads you into a home that is warm, inviting and spacious. The open-concept kitchen showcases granite countertops, stainless steel appliances, Maple cabinets and a Pantry Cabinet with convenient pull-out shelving. You can seamlessly blend indoor and outdoor living by sliding open the living room and dinette area sliding glass doors to the screened, covered lanai with 8" aluminum border base. It's the perfect place for entertaining. The primary bedroom with En-Suite bath has been extended 4 ft. to provide additional living space. It's the perfect getaway and you'll enjoy the EXTRA SPACE in the primary suite. The primary bathroom has ample closet space with His/Her Walk In Closets with Organization System, a large walk in shower with double shower heads, a separate water closet and separate His and Her Vanities. Her vanity has an additional make up area. Guests will appreciate the separate bedrooms and bath behind a pocket door. Additional features include: an automatic screen on the garage door, a separate irrigation meter, 18" diagonal tile in home (Bed 2 and Bed 3 are excluded), crown moulding, New A/C modulator, cabinetry in laundry room, Plantation Shutters in the Bedrooms, Upgraded entry light fixture, surround sound in the living room, additional insulation in the attic, new interior paint in Bedroom 1 and Guest Bathroom, new interior paint in the formal dining and dinette areas. Lake Ashton, a Florida Retirement community, has a Clubhouse with large grand ballroom, Outdoor Community Heated Pool, Tennis Courts, Bocce Ball, Shuffleboard, Fitness Center, Movie Theater, Bowling Lanes, Restaurant (Charm City)and More! The Health and Fitness center has indoor basketball, indoor racquetball, indoor heated pool, pickle ball and tennis courts, media center, card, craft and billiard rooms. There are two golf courses located in Lake Ashton. Memberships are optional and not a requirement to reside in Lake Ashton. Residents enjoy the resort style amenities and activities offered in Lake Ashton, a premier Florida Retirement Community. Don't miss this opportunity to own your piece of paradise. Check out the photo gallery and make your appointment to tour this home.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
4019 CARTERET DR, WINTER HAVEN, FL 33884
$269,99984 Days on yellowkey MLS ID: S5145776
REDUCED by $4,901 (1.8%) on 04/29/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2006Monthly Fee: $484 Tax: $1,704 (2025)Community: Traditions Ph 01Spa: NoSingle Family
Taxes:$1,704
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle & exceptional amenities. Fully upgraded with a brand new HVAC system and water heater installed (both in March 2026), an updated roof (November 2023), updated kitchen appliances (2024), refreshed landscaping (2026), newer irrigation controller and bidet (2025), fresh interior paint (December 2025), exterior paint (2024). This thoughtfully designed 2 bedroom, 2 bathroom home also includes a versatile office that can easily serve as a third bedroom, along with a spacious family room that provides additional living space for relaxing or entertaining. As you arrive, you’re welcomed by a covered and screened front entry. Inside, the open concept floor plan is enhanced by vaulted ceilings and a stylish blend of luxury vinyl flooring in the main living areas and ceramic tile in the kitchen, bathrooms and laundry room, creating both elegance and easy maintenance. The eat in kitchen is bright and inviting, featuring a closet pantry, stainless steel appliances that are just two years old and a comfortable dining space ideal for everyday meals. An interior laundry room is conveniently located just off the kitchen and provides direct access to the two car garage. Sliding glass doors from the living room lead to a screen enclosed patio, offering the perfect spot to unwind, entertain guests, or simply enjoy Florida’s beautiful year round weather. The primary suite serves as a relaxing retreat, highlighted by a tray ceiling, walk in closet and an ensuite bathroom with a double sink vanity and step-in shower. Outside, the property is beautifully framed by mature landscaping, with an attached two car garage, brick paved driveway and walkway that enhance the home’s inviting curb appeal. Residents of Traditions enjoy a true resort style lifestyle, featuring a lakefront clubhouse with a library, fitness center, card room, and billiards, as well as a resort style pool, hot tub and sauna. Additional amenities include tennis and shuffleboard courts, a dog park, a boat ramp and a dock overlooking Ruby Lake, providing endless opportunities for relaxation and recreation. The $484 monthly HOA fee covers lawn care (including bush/tree trimming and mulch replacement), exterior painting, cable, and internet. Ideally located near shopping, dining, and medical facilities with Publix opening soon just down the street, this home offers the perfect combination of comfort, convenience, and an active community lifestyle.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
400 EL CAMINO DR #210, WINTER HAVEN, FL 33884
$130,000130 Days on yellowkey MLS ID: S5142500
REDUCED by $5,000 (3.7%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1666 Built: 1974Monthly Fee: $448 Tax: $1,368 (2025)Community: Orchid Spgs Vill 400 San MiguelSpa: NoCondo
Taxes:$1,368
Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy & a peaceful feel while enjoying the security & convenience of community living. Inside you will find updated luxury vinyl flooring, windows, Stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer & AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well-maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!
649 BROADMOOR CIR, WINTER HAVEN, FL 33884
$149,700233 Days on yellowkey MLS ID: O6352259
REDUCED by $1,800 (1.2%) on 06/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1278 Built: 1981Monthly Fee: $314 Tax: $2,570 (2024)Community: Cypresswood Golf VillasVilla
Taxes:$2,570
Remarks: UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS. ALL interior contents and furniture convey with the property.
Listing is courtesy of: SUCCESS INVESTMENT REALTY (407-304-0490)
Listing Agent: Bill Sprys (407-574-9724)
6044 GRAND OAKS DR SE, WINTER HAVEN, FL 33884
$169,900386 Days on yellowkey MLS ID: S5126925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1982Monthly Fee: $65 Tax: $1,287 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$1,287
Remarks: Welcome to 6044 Grand Oaks Dr SE in Winter Haven, a beautifully updated waterfront home in the desirable 55+ community of Garden Grove Oaks, where you OWN THE LAND! Enjoy peaceful water views right from your backyard plus take advantage of a recent $15,000 price improvement, making this home an incredible value. This charming 2 bedroom, 2 bath residence offers the perfect blend of comfort, modern updates & Florida lifestyle living. The spacious and open floorplan features laminate flooring throughout the main living areas, creating a bright and inviting atmosphere. The kitchen has been tastefully updated with new cabinet facings, countertops, & Stainless Steel appliances, offering both style and functionality. The Florida room, complete with vinyl plank flooring, updated sliding doors & custom blinds, provides the perfect spot to relax and soak in the tranquil water views. Additional updates include double-pane windows throughout, as well as refreshed flooring, toilet, and faucets in the guest bathroom. The primary suite offers a barn door entry and private ensuite bathroom, while the guest bedroom provides flexibility for visitors or a home office. Garden Grove Oaks is a welcoming, well-maintained community offering a heated pool, clubhouse, and active social calendar, all with NO LOT RENT. With its waterfront setting, modern updates, and excellent value, this home is truly move-in ready. Don’t miss the opportunity to make it yours, schedule your private showing today!
144 BEVERLY DR, WINTER HAVEN, FL 33884
$389,90056 Days on yellowkey MLS ID: O6397768
REDUCED by $9,600 (2.4%) on 06/03/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2492 Built: 1963 Tax: $3,785 (2025)Community: Eloise Woods Lake Roy UnitSpa: NoSingle Family
Taxes:$3,785
Remarks: FLORIDA LIVING AT ITS BEST! Pool home + oversized lot + NO HOA + Chain of Lakes access just minutes from LEGOLAND Florida Resort! This fully updated 4-bedroom, 3-bath home in SE Winter Haven offers the lifestyle buyers are chasing with TWO master suites, a HUGE FENCED BACK YARD, heated pool, and room to bring the boat, jet skis, golf cart, and all the toys. Inside you’ll find a designer-style interior featuring luxury vinyl flooring, oversized living spaces, and a stunning chef’s kitchen with quartz countertops, custom soft-close cabinetry, stainless steel appliances, and a premium Ruvati workstation sink. The oversized primary suite feels like a private retreat with tray ceilings, spa-inspired bathroom, soaking tub, dual vanities, walk-in shower, and spacious walk-in closet. A second private ensuite is perfect for guests, multigenerational living, or an in-law suite. Step outside to your screened lanai overlooking the heated inground pool and massive backyard — ideal for entertaining, relaxing, and enjoying year-round Florida sunshine. The pool is equipped with a top-of-the-line Raypak pool heater, making it easy to enjoy swimming year-round! MAJOR UPGRADES INCLUDE: New roof (2019), whole-house replumb (2019), AC handler (2019), water heater (2019), remodeled kitchen (2021), luxury vinyl flooring (2021), top-of-the-line Raypak pool heater (2022), variable-speed pool pump (2024), irrigation system (2024), and guest bathroom remodel (2025). Located less than 2 minutes from the Lake Summit boat ramp with access to 20+ connected lakes, waterfront dining, skiing, and fishing, this home is the perfect mix of luxury, freedom, and Florida lifestyle
Listing Agent: Christina Loesch (347-977-0962)
314 TERRANOVA BLVD, WINTER HAVEN, FL 33884
$399,99043 Days on yellowkey MLS ID: O6401702
REDUCED by $10,010 (2.4%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1884 Built: 2006Monthly Fee: $55 Tax: $5,141 (2025)Community: Terranova Ph IvSpa: NoSingle Family
Taxes:$5,141
Remarks: Welcome to this stunning 3-bedroom + den pool home in a desirable gated community in Winter Haven—where space, style, and Florida living come together beautifully! Designed with a highly sought-after split-bedroom floor plan, this home offers both privacy and functionality. The luxurious primary suite is a true retreat, featuring elegant tray ceilings, dual walk-in closets, and a spa-inspired ensuite bath with dual vanities, a private water closet, a relaxing garden tub, and a separate walk-in shower. At the heart of the home, the gourmet kitchen impresses with granite countertops, stainless steel appliances, and a huge walk-in pantry, providing both style and ample storage. The versatile den/formal living room offers flexibility—perfect for a home office, media room, or additional living space. Step outside to your screened-in outdoor oasis, complete with a sparkling inground pool and an expansive lanai—ideal for entertaining, relaxing, or enjoying sunny Florida days. The fully fenced backyard offers plenty of room for a garden, pets, or play. With its premium features, flexible layout, and resort-style outdoor space, this home is a true standout. Don’t miss your chance—schedule your private showing today and make this Winter Haven pool home yours!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Jeff Jones (205-902-3584)
2108 CARTGATE LN, WINTER HAVEN, FL 33884
$310,0007 Days on yellowkey MLS ID: P4938873
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1961 Built: 2023Monthly Fee: $18 Tax: $6,185 (2025)Community: Villamar Ph 3Spa: NoSingle Family
Taxes:$6,185
Middle School: McLaughlin Academy Of Excellence
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Winter Haven area! This move-in ready property offers a perfect blend of comfort, style, and modern updates throughout. From the moment you step inside, you’ll notice the upgraded accent wall paneling featured in the foyer, dining room, and spacious primary bedroom, adding warmth and custom character to the home. The dining room and foyer have also been enhanced with updated light fixtures that provide a fresh, elegant touch. Pride of ownership is evident throughout, as this home has been exceptionally well maintained and cared for. With inviting living spaces, a functional layout, and tasteful upgrades, this home is ideal for both relaxing and entertaining. Conveniently located near shopping, dining, schools, and major roadways, this property combines comfort and convenience in one attractive package. Don’t miss your opportunity to own this charming Winter Haven home — schedule your private showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Matt Everett (231-563-3176)
328 VAIL DR, WINTER HAVEN, FL 33884
$335,00013 Days on yellowkey MLS ID: TB8511866
REDUCED by $10,000 (2.9%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1712 Built: 1984Monthly Fee: $13 Tax: $3,387 (2025)Community: Cedar Cove Ph 01Single Family
Taxes:$3,387
Elementary School: Pinewood Elem
Remarks: Located in the desirable Cedar Cove community of SE Winter Haven, this beautifully maintained 3-bedroom, 2-bath home offers convenience, comfort, and room to enjoy both indoors and out... especially with a NEW ROOF before closing. DISCOVER a spacious fenced backyard shaded by majestic oak trees, complete with a screened lanai, brick paver patio, storage shed, and double gate access - ideal for entertaining, relaxing evenings, or weekend gatherings. Inside, natural light fills the home through skylights and expansive windows, accenting the soaring ceilings, durable hard-surface flooring, and inviting fireplace that creates a warm focal point in the living area. The kitchen is designed to impress with abundant cabinetry, stylish finishes, ample prep space, with an oversized secondary pantry for exceptional storage. RETREAT to the private primary suite featuring dual walk-in closets and a beautifully updated bath with a sleek tiled walk-in shower and designer-inspired details. Secondary bedrooms have built-ins that offer flexibility for a home office, hobby room, or guest accommodations. Experience the perfect blend of privacy, functionality, and everyday living in this charming cul-de-sac home. Just minutes from shopping, dining, schools, medical facilities, and Legoland Florida, the property also provides easy access to Tampa and Orlando for effortless commutes to airports, attractions, and Gulf or Atlantic beaches.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: John Evans (813-992-3483)
3204 HERON CV, WINTER HAVEN, FL 33884
$784,000276 Days on yellowkey MLS ID: P4936093
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $15,000 (1.9%) on 05/20/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3640 Built: 1999Monthly Fee: $214 Tax: $6,459 (2025)Community: Heron CaySingle Family
Taxes:$6,459
Remarks: Under contract-accepting backup offers. Price Improvement. Offered for the first time, this stunning custom-built luxury home in SE Winter Haven in the gated community of Heron Cay. This exquisite Mediterranean style home features 3,640 square feet of living space with 3 bedrooms, plus a large flex room, 3 ½ baths plus a gorgeous pool and outside entertaining area on a lot measuring .61 acres. As you enter through the front double doors with custom decorative iron work and a soaring ceiling of over 21 feet, you are in a magnificent foyer. The living room has the first of two wood/gas fireplaces with views and access to your private pool via the oversized arched glass French doors on either side of the fireplace. The elegant dining room is oversized and perfect for large family gatherings or entertaining and is adjacent to your cook’s dream kitchen. In addition, off the entry foyer is a home office with a massive built in book case and desk with the flexibility to also be a 4th bedroom. The kitchen is a culinary dream with custom cabinetry, granite countertops, a spacious island, a walk-in pantry and upscale stainless appliances including a gas stove and double wall oven. The kitchen overlooks the great room, the breakfast nook and the pool. The great room ceiling beams are another architectural feature, and a second wood/gas fireplace is a focal point of this amazing room. Crown molding, columns, new windows, and a neutral color palette are throughout this home. Next to the great room is a large bonus/ flex space with French doors that can be used as a playroom, a library or even a workout space. The oversized primary bedroom has access out to the pool and features a spa type ensuite complete with a soaking tub and dual vanities. Twin oversized, walk-in closets feature built in shelves for keeping everything organized with access being via barn doors with glass panels. The guest rooms on the other side of the house have separate toilet/vanity areas with a shared tub/shower and private hallway. These are the only two rooms with carpet and it is a low pile neutral Berber style. Both guest rooms have oversized, walk in closets and there is a large linen closet in the private hallway. An indoor laundry room with built ins is well-located next to the kitchen and includes a laundry tub. Outdoor entertaining is perfect for celebrations in the screened lanai with your heated pool and outdoor kitchen! It is also a tranquil space to enjoy your friends and family as the pool features both a fountain and an area for plants. A pool bathroom is off the covered lanai and features a shower making an after swim shower really convenient. All of this beauty is set on professionally landscaped grounds with a whole house natural gas generator (2023) fed from the street and hurricane rated windows. The attached 3 car garage is oversized and features 3 separate garage doors and a driveway complete with a paver turnaround area for easy access in and out of the home. The home features a tile roof and many exterior trim details including landscape lighting only found in a custom, luxury home like this. The irrigation system is from this home’s private well. Built by the original owners and meticulously maintained showing pride of ownership throughout. This home has a low HOA that includes cable tv and Wi-Fi and is convenient to shopping, doctors, hospitals and local state colleges. Centrally located for an easy commute to Orlando or Tampa. Enjoy the virtual tour via the link.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Susan Mayrant (863-255-2715)
188 SWEET CIRCLE DR, WINTER HAVEN, FL 33884
$99,500125 Days on yellowkey MLS ID: G5107568
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1176 Built: 1982Monthly Fee: $279 Tax: $1,298 (2025)Community: Orange Manor West Coop IncSpa: NoManufactured Home
Taxes:$1,298
Remarks: Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1176 Square ft. 2 bedroom 2 bath 1991 mobile home with a front facing enclosed Florida room. The king size master bedroom has a walk-in closet and a private bathroom with step in shower. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.
Listing is courtesy of: MOSAIC SERVICES LLC (352-617-7606)
Listing Agent: Chris Cain (870-919-3798)
5413 SAN PIETRO DR, WINTER HAVEN, FL 33884
$409,999139 Days on yellowkey MLS ID: TB8465857
1 Days Off yellowkey (back on 1/30/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2892 Built: 2025Monthly Fee: $227 Tax: $2,688 (2025)Community: Villa MarSingle Family
Taxes:$2,688
Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. 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)
3831 GAINES DR, WINTER HAVEN, FL 33884
$775,0004 Days on yellowkey MLS ID: L4962328
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2678 Built: 2005Monthly Fee: $27 Tax: $3,522 (2025)Community: Gaines CoveSingle Family
Taxes:$3,522
Remarks: Welcome to this immaculate dream home at 3831 Gaines Dr! This beautifully updated 3-bedroom + office home features an open floor plan with stunning upgrades throughout, including an updated kitchen, modern bathrooms, and spacious living areas designed for both comfort and entertaining. The gorgeous kitchen is complete with brand-new appliances and flows seamlessly into the main living space, creating the perfect atmosphere for family gatherings and everyday living. Additional upgrades include a Kinetico water filtration system and an allergen air filtration system to help provide cleaner water and improved indoor air quality throughout the home. Step outside to your own private oasis featuring a heated pool, incredible outdoor kitchen, and a perfectly maintained yard that makes outdoor living effortless year-round. This move-in-ready home truly has it all — luxury, comfort, thoughtful upgrades, and plenty of space to live, work, and entertain!
Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)
Listing Agent: Vikki Thielen (863-604-6627)
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