Location: Winter Haven
Do Not Show Listings
116 MANDOLIN DR, WINTER HAVEN, FL 33884
$365,00046 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)
23 CASARENA CT, WINTER HAVEN, FL 33881
$230,00052 Days on yellowkey MLS ID: S5148554
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2045 Built: 1984Monthly Fee: $310 Tax: $3,909 (2025)Community: Casarena/LksSpa: NoSingle Family
Taxes:$3,909
Elementary School: Inwood Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with a breakfast bar and a convenient half bathroom. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile & hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor & multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip & dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining and major roadways. Low-maintenance living in a secure, gated community.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
634 WEXFORD CT, WINTER HAVEN, FL 33884
$235,00027 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
Elementary School: None
High School: None
Middle School: None
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)
441 SAN JOSE DR, WINTER HAVEN, FL 33884
$275,000401 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
Tax Year: 2024
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.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
812 ANDREW ST, WINTER HAVEN, FL 33881
$349,99036 Days on yellowkey MLS ID: O6406531
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2371 Built: 2026Monthly Fee: $6 Tax: $2,808 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,808
Elementary School: Fred G. Garnier Elem
Remarks: MOVE-IN READY! Discover lakeside living at Willowbrook North in Winter Haven, where modern single-family homes meet scenic Florida charm. Nestled near beautiful Lake Fannie and adjacent to the Willowbrook Golf Course, this boutique community offers thoughtfully designed homes with open-concept layouts, energy-efficient features, and stylish finishes. Residents enjoy convenient access to Hwy 27, Downtown Winter Haven, shopping, dining, entertainment, and the new Haines City Target & Crossroads Village. Community highlights include low HOA fees, scenic surroundings, and select homesites with water views. Experience comfort, convenience, and connectivity in one of Winter Haven’s most desirable new home communities.
Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)
Listing Agent: Adam Schott (407-270-2747)
811 ANDREW ST, WINTER HAVEN, FL 33881
$322,49019 Days on yellowkey MLS ID: O6410787
INCREASED by $15,000 (4.9%) on 05/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1600 Built: 2026Monthly Fee: $6 Tax: $2,695 (2025)Community: Willowbrook NorthSingle Family
Taxes:$2,695
Remarks: Under Construction. Ready in September 2026! The Atwood floor plan features 3 bedrooms, 2 full baths, approximately 1,600 sq. ft., an open-concept design, spacious kitchen island, private primary suite, and thoughtfully designed living spaces that combine comfort, style, and everyday functionality in a growing Central Florida location. Willowbrook North offers modern single-family homes in a boutique Winter Haven community near Lake Fannie and Willowbrook Golf Club, with convenient access to shopping, dining, Downtown Winter Haven, US-27, and I-4.
4577 BACK NINE DR, WINTER HAVEN, FL 33884
$349,600160 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)
530 SANCTUARY BLVD, WINTER HAVEN, FL 33881
$639,900113 Days on yellowkey MLS ID: S5144344
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3619 Built: 2023Monthly Fee: $83 Tax: $7,594 (2025)Community: Sanctuary By The Lake Ph OneSpa: NoSingle Family
Taxes:$7,594
Elementary School: Lake Alfred Elem
High School: Auburndale High School
Remarks: Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, & everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence & refined architectural detail. Step through the beautiful double front doors and experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, & expansive living spaces designed to feel both grand & inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal & casual living areas, creating an ideal setting for both entertaining & relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring granite countertops, upgraded stainless steel appliances, a breakfast bar, walk-in pantry, and generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room and dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms, and a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity, and a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes and quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace, and sink adds everyday convenience. A 50 amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks, and year-round entertainment, while nearby access to Lakeland and I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.
1517 AXEL CIR, WINTER HAVEN, FL 33880
$489,00028 Days on yellowkey MLS ID: P4938741
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3022 Built: 2023Monthly Fee: $71 Tax: $4,964 (2025)Community: Pinnacle PointSingle Family
Taxes:$4,964
Elementary School: Lake Shipp Elem
Remarks: Winter Haven home near Chain of Lakes featuring 5 bedrooms, 3 bathrooms, and 2 flexible bonus rooms offering exceptional convenience and a lifestyle close to everything Central Florida buyers love. This move in ready property provides effortless access to major commuter routes, grocery stores, shopping, dining, scenic walking trails, LEGOLAND Florida Resort, and Florida’s beautiful beaches just about 90 minutes away. Step into your own private outdoor sanctuary designed for both relaxation and entertainment. The caged saltwater pool includes a 6×10 sun shelf perfect for in water lounging along with a 3 to 6 foot depth range ideal for both play and leisurely floating. Enjoy the luxury of a heated spa with priority Jacuzzi jet action creating the perfect setting for evening unwinding, stress relief, muscle relaxation, or hosting friends for cozy nights under the stars. The spacious gazebo offers a shaded retreat for outdoor dining, socializing, or simply enjoying the Florida breeze. Practical upgrades elevate this property as it is equipped to support a home generator, has a warrantied water softener for supreme taste, two 5-ft gates that create a wide 10-ft entry to the backyard and a on-site shed adding valuable extra storage keeping everything tidy and easy to access. Inside, the home feels bright, modern, and truly move in ready. The open concept layout creates an inviting flow throughout, and the generous kitchen is perfectly suited for gatherings, meal prep, and everyday connection. With its flexible floor plan, this home easily accommodates large families, multi generational living, or hosting guests with comfort and privacy. A standout property offering both lifestyle and practicality. This home is a must see!
Listing Agent: Andrea Friedmann (863-661-6535)
943 SUMMER GLEN DR, WINTER HAVEN, FL 33880
$325,00088 Days on yellowkey MLS ID: O6386883
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1846 Built: 2019Monthly Fee: $30 Tax: $2,755 (2025)Community: Coventry Cove Ph IiSingle Family
Taxes:$2,755
Remarks: One or more photo(s) has been virtually staged. 943 Summer Glen Dr is a spacious and well-maintained home offering exceptional value in the heart of Winter Haven. This move-in-ready residence features a functional, open floor plan designed for modern living and effortless entertaining. The bright, airy interior flows seamlessly into versatile living spaces, including a comfortable primary suite and additional bedrooms perfect for a growing family or a dedicated home office. Positioned in a quiet, family-oriented community, this property sits just moments from top-rated schools like Lake Shipp Elementary and the renowned Jewett School of the Arts. Residents enjoy immediate access to the Chain of Lakes for premier boating and fishing, as well as the dining and boutiques of historic downtown Winter Haven. Perfectly situated between Orlando and Tampa, this home provides a high-quality lifestyle and significant appreciation potential without the metropolitan price tag. Schedule your private showing today to discover why 943 Summer Glen Dr is the perfect place to start your next chapter!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Stacey Vazquez (407-874-5751)
1911 BROWN ST NE, WINTER HAVEN, FL 33881
$249,000153 Days on yellowkey MLS ID: O6373193
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1440 Built: 2020 Tax: $3,345 (2025)Community: Not In A SubdivisionSingle Family
Taxes:$3,345
Remarks: Location Location!! NO HOA, NO CDD, Built in 2020. QUIET, YET CONVENIENT LOCATION! Whether you're shopping for a first home, Investment or last home, this beauty is just what you’ve been looking for! Beautiful 3BR/2BA home open floor plan, living room/dinning groom /family room kitchen combo. located in NE Winter Haven. Large walk in closet in the Master Bedroom/Bath. Master bath contains a shower and tub, as well as double vanity. Kitchen comes equipped with stainless steel appliances, Vinyl flooring consistent through entire home, central a/c and heating. All stainless-steel appliances convey. This home will not last long, call today for your private showing.
Listing is courtesy of: VYLLA HOME (813-947-7996)
Listing Agent: Manny Duran, Jr (407-334-8893)
1501 7TH ST SE, WINTER HAVEN, FL 33880
$365,00068 Days on yellowkey MLS ID: A4689208
REDUCED by $4,900 (1.3%) on 06/03/2026
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2806 Built: 1959 Tax: $5,528 (2025)Community: Highland EstatesSingle Family
Taxes:$5,528
Remarks: Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT, 2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shaker cabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature modern updated finishes. The living room features a large brick fireplace. The large fenced in backyard has a large underground pool just waiting for its new homeowners to spend their afternoons building memories and soaking up the Florida sun. The front of the home features 2 driveways. This home is close to Legoland, Lakes galore and amazing shopping, dining and entertainment.
Listing is courtesy of: ELEVATE REALTY LLC (561-427-3923)
Listing Agent: Laura Auten (561-427-3923)
300 AVENUE V NE, WINTER HAVEN, FL 33881
$190,00051 Days on yellowkey MLS ID: L4961309
REDUCED by $10,000 (5.0%) on 06/03/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 912 Built: 1963 Tax: $169 (2025)Community: Eula Vista SubSingle Family
Taxes:$169
Elementary School: Clarence Boswell Elem
Remarks: Welcome to this charming 3 bedroom, 1 bath home ideally located in the heart of Winter Haven, just minutes from shopping, dining, and schools. From the moment you arrive, you’ll be greeted by a lush, established front garden, perfect for those who enjoy outdoor living or gardening. The home features a covered front porch, ideal for relaxing mornings or unwinding in the evenings, along with a convenient one-car carport. Inside, you’ll find a warm and inviting living space highlighted by durable wood-look tile flooring that flows seamlessly throughout the main areas. The kitchen and dining room combination offers a functional layout with plenty of room for everyday living and entertaining. Tucked away at the rear of the home, the spacious primary bedroom provides added privacy and a generously sized closet. Two additional bedrooms offer flexibility for guests, a home office, or hobby space. The full bathroom includes a single-sink vanity and a tiled tub/shower combo. Additional features include an exterior storage/laundry room located under the carport with washer and dryer hookups. Whether you're a first-time homebuyer, investor, or looking to downsize, this home offers great potential and opportunity. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
825 NW AVENUE Y AVE NW, WINTER HAVEN, FL 33881
$285,00051 Days on yellowkey MLS ID: S5148593
REDUCED by $10,000 (3.4%) on 06/03/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1497 Built: 1978 Tax: $3,281 (2025)Community: Hartridge ManorSingle Family
Taxes:$3,281
Elementary School: Walter Caldwell Elem
Remarks: Welcome to your turn-key Florida retreat! This beautifully reimagined home is a masterclass in modern updates and serene living, nestled within a tranquil, established community. From the moment you arrive, the vibrant curb appeal and crisp, clean lines signal a home that has been maintained with pride. The heart of the residence is an open, sun-drenched kitchen featuring premium stainless-steel appliances, sleek cabinetry, and chic subway tiling—perfect for the culinary enthusiast or the frequent entertainer. With durable wood-look flooring and a versatile, oversized utility suite, this home seamlessly blends style with everyday functionality. Beyond the interior, your private oasis awaits. Relax on the expansive screened-in porch or take advantage of the massive, fully fenced backyard—a rare find that offers limitless potential for a pool, garden, or workshop. The long driveway and integrated carport provide plenty of space for your vehicles and toys, making this the perfect home base for a Central Florida lifestyle. Whether you’re a first-time buyer or a savvy investor looking for a high-quality asset, this property offers an optimistic outlook and incredible value. Opportunity is knocking—book your showing today and claim your piece of paradise!
Listing is courtesy of: MCO REALTY (407-479-8601)
Listing Agent: Vernel Smith (863-224-1942)
3204 HERON CV, WINTER HAVEN, FL 33884
$784,000285 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)
4140 SOPHIA BLVD, WINTER HAVEN, FL 33880
$274,90062 Days on yellowkey MLS ID: TB8495461
REDUCED by $5,000 (1.8%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1711 Built: 2017Monthly Fee: $25 Tax: $4,540 (2025)Community: Buckeye RidgeSingle Family
Taxes:$4,540
Elementary School: Elbert Elem
High School: Chain of Lakes Collegiate High
Remarks: MOVE-IN READY WITH MODERN UPDATES ON A PRIME CORNER LOT! Built in 2017 and featuring a LOW HOA, this beautifully maintained home offers a desirable open floor plan with a 3-way split bedroom layout, delivering the perfect balance of functionality and privacy. Enjoy peace of mind with NEW luxury vinyl plank flooring (2025) and fresh interior paint (2025), creating a clean, modern, truly turnkey feel throughout. Architectural details like decorative arches add character, while 18x18 tile in all wet areas enhances durability and style. The kitchen showcases 36” espresso cabinetry, generous storage, and all appliances included, making it ideal for both everyday living and entertaining. Additional highlights include window treatments throughout, an inside laundry room with washer and dryer, and abundant storage space. Step outside to your covered lanai, perfect for relaxing year-round. Situated on a spacious corner lot, the property offers added privacy and curb appeal. Conveniently located just minutes from Highway 27 and approximately 15 minutes to I-4, providing easy access to commuting, shopping, and dining. 1711 sq ft | 3 Bedrooms | 2 Bathrooms | 2-Car Garage
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: William Kilpatrick (863-669-8090)
1818 6TH ST SE, WINTER HAVEN, FL 33880
$500,000283 Days on yellowkey MLS ID: O6341480
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2006 Built: 1963 Tax: $3,632 (2023)Community: Southeast TerraceSingle Family
Taxes:$3,632
Elementary School: John Snively Elem
Tax Year: 2023
Remarks: Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.
Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)
Listing Agent: Washington Costa (407-460-4097)
5413 SAN PIETRO DR, WINTER HAVEN, FL 33884
$409,999148 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
Elementary School: Pinewood Elem
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
$775,00013 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)
908 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$299,90025 Days on yellowkey MLS ID: P4938735
REDUCED by $9,100 (2.9%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1200 Built: 1952 Tax: $3,909 (2025)Community: East View PkwySingle Family
Remarks: Sitting on Lake Jessie and on a beautiful lot along the Winter Haven Chain of Lakes, this property offers an incredible opportunity to own waterfront living at an affordable price point. Known as the “Chain of Lakes City,” Winter Haven features dozens of interconnected lakes perfect for boating, fishing, watersports, and enjoying the true Florida lifestyle. Whether you’re looking for a full-time residence, seasonal snowbird retreat, or a smart long-term investment opportunity, this home is priced right for someone ready to make a few updates while securing a spot on the highly desirable main Chain of Lakes. Opportunities like this are becoming harder and harder to find. The home includes a metal roof, updated AC system, and updated plumbing, giving you a solid foundation to make it your own. The oversized lot provides plenty of extra driveway space and room to add a large garage or additional storage for boats, trailers, or recreational vehicles. Relax and unwind in the screened-in area while enjoying the peaceful lake breeze and beautiful waterfront surroundings. With endless potential and a low price, this property is a rare chance to create your dream lakefront getaway without breaking the bank.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
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