Location: Winter Haven
Do Not Show Listings
112 PAINE DR, WINTER HAVEN, FL 33884
$315,000135 Days on yellowkey MLS ID: L4957763
REDUCED by $35,000 (10.0%) on 04/21/2026
Bed: 5 Bath: 2.0 Liv Area Sq Ft: 2078 Built: 1965 Tax: $3,343 (2024)Community: Fla Highlands Co SubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,343
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Brandy Duncan (863-585-6849)
906 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$792,000136 Days on yellowkey MLS ID: L4957757
REDUCED by $88,000 (10.0%) on 04/21/2026
Bed: 9 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5700 Built: 1954 Tax: $5,237 (2024)Community: East View PkwySingle Family
Taxes:$5,237
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Middle School: Westwood Middle
Remarks: Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.
936 AVENUE T SE, WINTER HAVEN, FL 33880
$195,00029 Days on yellowkey MLS ID: O6392455
REDUCED by $55,000 (22.0%) on 04/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1410 Built: 1960 Tax: $3,545 (2025)Community: WoodmereSingle Family
Taxes:$3,545
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. : Offers may be entered ONLINE through Monday, May 4, 2026 at 2:00 pm. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today! Offers may be entered ONLINE through Monday, April 20, 2026 at 2:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)
Listing Agent: Daniel Rodriguez (407-934-0305)
689 VITTORIO DR, WINTER HAVEN, FL 33884
$315,000176 Days on yellowkey MLS ID: O6353926
2 Days Off yellowkey (back on 1/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2053 Built: 2021Monthly Fee: $19 Tax: $5,951 (2025)Community: Villamar Ph 2Single Family
Taxes:$5,951
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Mclaughlin Academy Of Excellence
Remarks: Under contract-accepting backup offers. Welcome to the Serendipity floor plan — where comfort meets style! This stunning three-bedroom, den, two-bathroom home offers the perfect blend of modern design and everyday convenience. Step inside to find a bright, open-concept layout featuring high vaulted ceilings, a spacious great room, a beautifully appointed kitchen with a large island and walk-in pantry, and a cozy dining area ideal for gatherings. The owner’s suite provides a peaceful retreat with dual walk-in closets and a luxurious en-suite bath. The flexible den is perfect for a home office, guest space, or hobby room, offering versatility to fit your lifestyle. Enjoy year-round outdoor living in the beautiful enclosed lanai overlooking the fully fenced backyard—perfect for relaxing or entertaining in privacy. Located in a highly desirable area, this home offers convenient access to top-rated schools, shopping, dining, parks, and houses of worship. Designed for both elegance and functionality, the Serendipity truly lives up to its name—a happy discovery of the place you’ll love to call home.
Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)
Listing Agent: Kelly Martinez (407-864-8965)
4020 CARTERET DR, WINTER HAVEN, FL 33884
$419,90042 Days on yellowkey MLS ID: O6389154
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2282 Built: 2015Monthly Fee: $484 Tax: $3,537 (2025)Community: TraditionsSingle Family
Taxes:$3,537
Remarks: Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Sofia Lovinsky (407-376-1845)
446 TERRANOVA ST, WINTER HAVEN, FL 33884
$425,00057 Days on yellowkey MLS ID: P4937910
REDUCED by $10,000 (2.3%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2121 Built: 2004Monthly Fee: $664 Tax: $2,816 (2025)Community: Terranova Ph 03Spa: NoSingle Family
Taxes:$2,816
Remarks: Situated in the desirable gated community of Terranova, this wonderful 3-bedroom, 2-bath pool home with a den offers comfort, and efficiency. Enjoy low energy costs thanks to the FULLY PAID SOLAR SYSTEM, providing long-term savings and sustainability. Upon arrival, you’re welcomed by a lovely covered entry accented with a leaded glass front door and arched transom window, filling the foyer with natural light. The spacious great room features hand-scraped engineered wood flooring and a large sliding glass door that seamlessly brings the outdoors in, offering views of the patio and pool area. The well-appointed kitchen showcases white cabinetry with brushed nickel hardware, beautifully complemented by a glass tile backsplash. Stainless Steel Appliance Package includes a Gas Range. A granite-topped breakfast bar with pendant lighting provides additional seating and creates a natural gathering space. A formal dining room is conveniently located nearby, making entertaining effortless. The primary bedroom suite offers a walk-in closet and a cozy sitting niche—ideal for relaxing while enjoying views of the pool. The primary bathroom is thoughtfully designed with dual sinks, a linen closet, walk-in shower, private water closet, and a luxurious garden tub. Step outside to your private outdoor oasis. The lagoon-style pool with a cascading waterfall creates a tranquil ambiance, while the covered patio provides shade from the Florida sun and convenient access to the guest bath—perfect for poolside gatherings. A fully fenced yard ensures privacy and features an avocado and citrus trees. Additional Features: Den/office, Laundry room with washer and dryer, Solid surface flooring throughout, Water heater (2020), Architectural shingle roof (2020), 18 SEER Carrier HVAC system with heat pump (2020) and warranty, In-wall pest control system, Pull-down attic stairs, Irrigation well, Smart lock entry, Child safety fence for pool, Exterior carriage lighting, Oversized driveway, Two-car garage with door opener and keyless entry panel. This fabulous home is conveniently located in a picturesque gated community near schools, shopping, restaurants, and Legoland, offering the perfect blend of luxury, convenience, and energy efficiency.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
5347 MICKEY AVE, WINTER HAVEN, FL 33884
$349,99921 Days on yellowkey MLS ID: S5146851
INCREASED by $478 (0.1%) on 04/21/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 2026Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: This home offers, 9"4' ceilings and 8' doors, 42' cabinets, 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, secondary bedroom with its own bathroom.
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
5171 KINSLEY DR, WINTER HAVEN, FL 33884
$339,999239 Days on yellowkey MLS ID: S5133352
INCREASED by $3,100 (0.9%) on 04/21/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2050 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: An inviting covered entry welcomes guests to this inspired Tarragon home. Pass two bedrooms, a shared bath, a flex room and a laundry on your way to a spacious great room with an adjacent covered patio. The well-appointed kitchen boasts a center island, a walk-in pantry and a dining nook. Showcasing a generous walk-in closet and an attached bath with double sinks. An additional bedroom and bathroom round out this inspired plan. *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!
5147 KINSLEY DR, WINTER HAVEN, FL 33884
$314,999328 Days on yellowkey MLS ID: S5127810
REDUCED by $3,636 (1.1%) on 04/21/2026
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!
5135 KINSLEY DR, WINTER HAVEN, FL 33884
$314,999329 Days on yellowkey MLS ID: S5127745
REDUCED by $951 (0.3%) on 04/21/2026
Remarks: Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42" white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a covered patio. This could be your dream home! *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!
3022 HICKORY ST NW, WINTER HAVEN, FL 33881
$273,000131 Days on yellowkey MLS ID: A4674941
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1602 Built: 1955 Tax: $1,866 (2024)Community: Biltmore ShoresSpa: NoSingle Family
Taxes:$1,866
Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.
Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)
Listing Agent: Ashlee Morrell (941-740-9134)
3820 TRADITIONS BLVD N, WINTER HAVEN, FL 33884
$380,00022 Days on yellowkey MLS ID: P4938275
0 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2400 Built: 2006Monthly Fee: $485 Tax: $2,300 (2025)Community: Traditions Ph 01Spa: NoSingle Family
Taxes:$2,300
Remarks: This stunning property is situated on a premium lot, offering picturesque views of the pond. Featuring a highly desirable split-bedroom floor plan, this partially furnished home includes three bedrooms and two baths. As you step inside, you're welcomed by a charming screened-in front porch with a leaded glass door and transom window. The kitchen boasts 42" upper maple wood cabinetry, accented with braided trim, crown molding, and convenient pull-out drawers. Recent updates include a new refrigerator and microwave, along with a closet pantry. Enjoy casual meals at the breakfast bar or in the cozy breakfast nook. The open-concept design seamlessly connects the formal dining room and living room, both of which showcase stunning pond views. The spacious great room is bright and inviting, featuring high ceilings and vinyl plank flooring. Architectural details like arched entryways, crown molding, and decorative niches enhance the home's elegant atmosphere. The four-seasons room, lined with large windows, allows you to enjoy the scenic views year-round. The generously sized primary bedroom suite serves as a private retreat, complete with plantation shutters and a cozy sitting area. Dual walk-in closets with overhead luggage shelves offer ample storage. The primary bathroom features a comfort-height vanity with double sinks, a linen closet, a seated walk-in shower, a water closet, and a luxurious garden tub. For outdoor enjoyment, the expansive screened-in lanai provides a peaceful space to relax. Additional features include a laundry room with a washer, dryer, utility sink, and extra cabinetry, solid surface flooring throughout, a water heater (installed in 2024), an upgraded HVAC system with an Aprilaire electronic filtration system, custom window treatments, an invisible dog fence, and a five-zone irrigation system with an irrigation meter. The home also boasts an architectural shingle roof (installed in 2019), professionally landscaped corner lot, pull-down attic stairs, alarm system, gutters, exterior lighting, paved walkway and driveway, and a two-car garage with shelving and a garage door opener. Residents of Traditions enjoy a wealth of amenities, including a lakefront clubhouse with a dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, and courts for tennis, pickleball, basketball, bocce ball, and shuffleboard. The community also offers a fitness center, aerobics studio, and more. Conveniently located near shopping, dining, major routes, and Legoland, this home offers an exceptional lifestyle. The monthly HOA fee covers exterior house painting, cable, internet, lawn service, and clubhouse amenities, ensuring a maintenance-free living experience.
740 SQUIRES GROVE DR, WINTER HAVEN, FL 33880
$369,99059 Days on yellowkey MLS ID: S5144206
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2616 Built: 2022Monthly Fee: $64 Tax: $5,142 (2025)Community: Squires Grove Ph 2Single Family
Taxes:$5,142
Remarks: PRICE REDUCED!!! Seller is motivated... Welcome to 740 Squires Grove Dr. This beautiful 5 bedroom, 3 bath residence offers the space you've looking for, filled with natural light and and large fenced backyard ideal for gatherings, pets or relaxing outdoors. Well located near shopping, dining, hospitals, major highways, and just minutes from LEGOLAND. Book your showing today!.
Listing is courtesy of: NORTHGROUP REAL ESTATE, INC (561-222-1850)
Listing Agent: Lulis Batista (407-969-2098)
4612 REYNOSA DR SW, WINTER HAVEN, FL 33880
$320,000257 Days on yellowkey MLS ID: V4944212
1 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1716 Built: 1984 Tax: $4,573 (2024)Community: Plaza SubSingle Family
Taxes:$4,573
Elementary School: Lake Shipp Elem
Remarks: Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Trent Shackelford (941-518-7875)
3030 LAUREL OAK LN, WINTER HAVEN, FL 33884
$339,990120 Days on yellowkey MLS ID: L4957976
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2004 Built: 2022Monthly Fee: $22 Tax: $6,438 (2024)Community: Villamar Ph 4Single Family
Taxes:$6,438
Remarks: Welcome to your dream home in the heart of Villamar, where modern living meets serene surroundings. This stunning four-bedroom, two-bathroom residence is perfectly situated on a desirable corner lot, offering privacy and tranquility with no backyard neighbors, as it backs up to a lush conservation area and a picturesque pond. Step inside to discover a bright and airy open-concept design, accentuated by high ceilings that create an inviting ambiance. The gourmet kitchen is a chef's delight, featuring sleek stainless steel appliances, a spacious island with seating for up to six, and elegant decorative lighting that enhances the space. The stylish tile backsplash adds a touch of sophistication to this culinary haven. Retreat to the expansive primary bedroom, where a tray ceiling enhances the sense of luxury. The en suite bathroom completes the suite with a private water closet, a large walk-in shower, dual sinks, a generous walk-in closets, providing ample storage and comfort. This home is designed for modern convenience, featuring a designated indoor laundry room and a host of upgrades, including a water softener system with reverse osmosis. Step through the sliding glass doors to the screened-in lanai, equipped with a ceiling fan and epoxy flooring, perfect for enjoying Florida's beautiful weather. The private backyard, enclosed by a vinyl fence, offers a secure space for relaxation or play. Additional highlights include a spacious two-car garage and access to the community pool, ideal for those hot summer days. Located close to the enchanting Chain of Lakes and Legoland, as well as an array of shopping and dining options, this home promises a lifestyle of comfort and convenience. Don't miss the opportunity to make this exceptional property your new home. Schedule a viewing today and experience all that this remarkable residence has to offer!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
215 SANTA ROSA DR, WINTER HAVEN, FL 33884
$329,90015 Days on yellowkey MLS ID: TB8494313
REDUCED by $20,000 (5.7%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2355 Built: 1988Monthly Fee: $46 Tax: $3,255 (2025)Community: Overlook EstatesSingle Family
Taxes:$3,255
Elementary School: Elbert Elem
Remarks: One or more photo(s) has been virtually staged. This is a 4 bedroom, 2 bathroom single family home with approximately 2,355 square feet on about 0.34 acres, a 2 car garage, a wood burning fireplace, and a screen enclosed pool and jacuzzi inside a gated community just minutes from Legoland. This home stands out for buyers who want strong square footage, a functional layout, and outdoor features that are already in place. The floor plan gives plenty of room for daily living, guests, or flexible use, and the 2 car garage adds practical storage and parking that matters for long term ownership. The gated setting brings added privacy and neighborhood appeal while keeping the property close to shopping, dining, schools, and the main conveniences that make this part of Winter Haven attractive. Inside, the home gives a buyer a solid starting point with the chance to update key finish areas over time. The kitchen and bathrooms are the main spaces where a future owner may choose to remodel, making this a value add opportunity for someone who wants to improve the home around an already desirable footprint. The wood burning fireplace adds character to the living area and helps give the interior more presence than a basic builder layout. This is the kind of house that works well for a buyer who wants size, location, and lifestyle features first, then the freedom to make design changes at their own pace. The outdoor setup is a major part of the appeal. The screen enclosed pool and jacuzzi create a more complete Florida living experience and give the backyard a true entertaining and relaxation element. The screened enclosure adds usability and helps the pool area feel like an extension of the home rather than just an extra feature. The pool is reported to be working, with the main noted item being a light, and seller will have the pool fully cleaned and ready to go. For buyers searching online for a Winter Haven pool home, a gated community home near Legoland, a house with jacuzzi and screened pool, or a Polk County property with indoor and outdoor living space, this home checks multiple search points that matter. Major system notes also help frame the opportunity clearly. The AC is reported at about 10 years old, the water heater about 2 years old, and the roof about 10 years old, with a prior note that inspection suggested roof replacement due to age and mentioned one small leak in a closet. The septic system was replaced, which is an important update for future maintenance planning. HOA is reported at approximately $550 a year, and rental restrictions are reported as no. For buyers looking for a 4 bedroom 2 bathroom home in Winter Haven, a gated neighborhood property near Legoland, or a Florida home with pool, fireplace, garage, and room to personalize, 215 Santa Rosa Dr presents a strong opportunity. SOME PHOTOS HAVE BEEN VIRTUALLY EDITED.
Listing is courtesy of: SILVER DOOR REALTY LLC (954-993-0696)
Listing Agent: Michelle Paez (954-589-0144)
1658 TEAGAN LN, WINTER HAVEN, FL 33884
$315,99013 Days on yellowkey MLS ID: S5146407
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1933 Built: 2024Monthly Fee: $16 Tax: $4,170 (2025)Community: Peace Creek ReserveSingle Family
Taxes:$4,170
Elementary School: Wahneta Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.
Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)
Listing Agent: Barbara Cunha De Freitas (617-458-0838)
2014 10TH ST NW, WINTER HAVEN, FL 33881
$228,00096 Days on yellowkey MLS ID: O6374317
REDUCED by $1,900 (0.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1229 Built: 1953 Tax: $2,753 (2024)Community: Villa ManorSingle Family
Taxes:$2,753
Elementary School: Frank E. Brigham Academy
Remarks: One or more photo(s) has been virtually staged. 4.99% Rate 30-year fixed FHA/VA Act now ! Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Daniel Araque (321-276-0747)
3863 BEDFORD AVE, WINTER HAVEN, FL 33884
$345,00014 Days on yellowkey MLS ID: O6396509
REDUCED by $10,000 (2.8%) on 04/16/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1797 Built: 2017Monthly Fee: $485 Tax: $4,293 (2025)Community: Traditions Ph 02Single Family
Taxes:$4,293
Remarks: As you walk into this beautiful home, you are welcomed by a den/office on the right with double doors, which can easily be used as a third bedroom if desired. Continuing through the home, you’ll find a spacious formal dining room separate from the main living area. As you exit the dining room, the home opens up into a bright open-concept space featuring the living room, kitchen, and a cozy coffee/breakfast area, perfect for everyday living and entertaining. The gourmet kitchen features upgraded Kraft Maid cabinetry, Cambria quartz countertops, newer KitchenAid appliances, and a gas convection range, all overlooking the spacious living room with large windows and sliding glass doors that bring in plenty of natural light. The home offers three sliding glass doors that lead out to a large screened-in lanai, perfect for relaxing and enjoying the Florida lifestyle. The lanai also features an extended screened area with artificial turf. The spacious primary bedroom includes a walk-in California closet system and an en-suite bathroom with dual sinks, comfort-height vanity, separate toilet room, and a walk-in tiled shower. Throughout the home you will find crown molding, imported Italian tile flooring, engineered wood flooring, plantation shutters, and Hunter Douglas remote-control shades. Additional features include a laundry room with washer and dryer, double-pane low-E windows, an AO Smith hybrid water heater, Pelican salt-free water filtration system, gutters, and a stone exterior façade with a brick paver driveway and extended front walkway. The two-car garage features an insulated garage door, garage door opener, overhead storage racks, and a workbench area with pegboard and additional workspace. Located in the desirable Traditions 55+ gated community, residents enjoy resort-style amenities including a clubhouse, heated pool and hot tub, ballroom, craft room, meeting rooms, library, computer room, fitness center, tennis and pickleball courts, dog park, and more. Monthly HOA fees include lawn service, cable TV, internet, and exterior house painting.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Stephanie Class Cordero (321-208-0378)
1936 CROSSROADS BLVD, WINTER HAVEN, FL 33881
$495,00046 Days on yellowkey MLS ID: L4959864
REDUCED by $4,900 (1.0%) on 04/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 2018Monthly Fee: $133 Tax: $2,645 (2025)Community: Crossroads At Lake RegionSpa: YesSingle Family
Taxes:$2,645
Remarks: One or more photo(s) has been virtually staged. Welcome to 1936 Crossroads Blvd in the highly sought-after gated community of Crossroads at Lake Region. This exquisite entertainer’s paradise comes partially furnished, features a private screened pool and spa, upgraded finishes throughout, and a fully fenced backyard designed for relaxation and entertaining. This meticulously upgraded Rockingham II floor plan, built in 2018, offers nearly 2,500 square feet of thoughtfully designed living space with one of the most functional and desirable layouts in the community. The open-concept design provides a natural flow from the kitchen to the main living area with sweeping views of the covered lanai and pool enclosure, making the home ideal for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, pendant lighting, abundant cabinetry, and a large breakfast bar overlooking the main living area. Wood-look tile flooring throughout the main living areas adds durability while giving the home a clean, modern feel. The primary suite features an upgraded tray ceiling, abundant natural light, and a spacious walk-in closet with a custom California Closet system for added organization. The ensuite bath offers dual vanities, a soaking tub, and a separate glass-enclosed shower. Step outside to the true highlight of the home. The screened pool and spa area features an upgraded epoxy-coated deck that gives the outdoor space a clean, finished appearance while also being durable and easy to maintain. The fully fenced backyard provides privacy and security, while the covered lanai and extended deck space offer plenty of room for outdoor seating, grilling, and entertaining year-round. The property also features a dedicated irrigation well to help maintain the landscaping efficiently, thereby reducing water costs. The home is also equipped with a programmable permanent exterior lighting system, allowing for customizable accent lighting year-round. This incredible property is conveniently located near Highway 27 and the Polk Parkway, offering quick access to I-4, major metro areas, local theme parks and attractions, shopping, dining, and Florida’s beautiful beaches. Do not miss this incredible opportunity. Schedule your private showing today.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Craig Murrell (863-409-7718)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.