Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Price: $400,000 to $499,000
Do Not Show Listings
Winter Haven - 51 properties found
1854 ELOISE COVE DR, WINTER HAVEN, FL 33884
$450,000102 Days on yellowkey MLS ID: L4958664
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2888 Built: 2006Monthly Fee: $94 Tax: $3,516 (2025)Community: Eloise CoveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,516
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Denison Middle
Remarks: PRICED REDUCED!! This wonderful 4-bedroom, 3-bath pool home is located in the gated community of Eloise Cove and is a former Lennar model featuring the highly sought-after Sheffield floor plan. NEW ROOF 9/2025. Water heater 2021. The spacious kitchen offers granite countertops, stainless steel appliances, double ovens, and a breakfast bar—perfect for entertaining. The home boasts a separate living room, dining room, family room, and office, along with a split bedroom floor plan for added privacy. The primary suite features a walk-in closet, dual vanities, a jetted soaking tub, and a separate shower. Additional highlights include a laundry room, crown molding, tinted windows, a security system, and magnificent decorator faux finishes with custom window treatments already in place for the next owner. Enjoy Florida living at its finest on the large screened lanai overlooking a private pool and fully fenced backyard. Residents also have access to a community dock on Lake Eloise, part of the renowned Chain of Lakes. Call today to schedule your private showing!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Amy Reynolds (863-412-2279)
2112 RIVER HAWK LOOP, WINTER HAVEN, FL 33880
$429,9004 Days on yellowkey MLS ID: S5148856
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2378 Built: 2026Monthly Fee: $98 Tax: $228 (2025)Community: Residences Of Winter HavenSingle Family
Taxes:$228
Elementary School: Lake Shipp Elem
Middle School: Westwood Middle
Remarks: Under Construction. Under Construction. Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Crystal River Gen Suite floor plan brings a versatile elegance to everyday living. The open layout is anchored by a stunning gourmet kitchen featuring a waterfall island, while a private Gen Suite offers ultimate flexibility and independence with its own entrance, bath, and kitchenette. It’s a lovely modern space that’s ready for you to make it your own.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)
104 SANDERLING DR, WINTER HAVEN, FL 33881
$419,00041 Days on yellowkey MLS ID: O6392989
REDUCED by $6,000 (1.4%) on 05/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 2004Monthly Fee: $34 Tax: $6,245 (2025)Community: Hamilton West Ph 01Single Family
Taxes:$6,245
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this beautifully reimagined 4-bedroom, 2-bathroom pool home, perfectly positioned on a premium corner lot. Thoughtfully updated with a new roof (2021), HVAC (2024), and fresh interior paint throughout—including ceilings and the pool deck—this residence offers effortless, move-in-ready living. Inside, a refined layout unfolds with a formal dining space and a flexible bonus room, ideal for a private office or curated living area. The heart of the home showcases an open-concept design, where the living room flows seamlessly into a sophisticated kitchen and breakfast space, perfect for both intimate gatherings and entertaining. The kitchen is appointed with quartz countertops, high-end appliances, a built-in bar fridge, and a convenient pot filler, blending style with function. A desirable three-way split floor plan ensures privacy and comfort throughout. Outdoors, enjoy a screened-in patio overlooking a sparkling pool, complemented by a generously sized, fully fenced backyard, your own private retreat designed for the Florida lifestyle. Experience the perfect blend of modern upgrades and timeless comfort. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Kevin Asenjo (407-844-5252)
144 BEVERLY DR, WINTER HAVEN, FL 33884
$409,90024 Days on yellowkey MLS ID: O6397768
REDUCED by $10,100 (2.4%) on 04/28/2026
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: Updated 4/3 pool home with two master suites, quartz kitchen, no HOA, and walkable access to the Winter Haven Chain of Lakes—now at an improved price. This move-in-ready home offers a bright, open layout with luxury vinyl plank flooring, a modern great room overlooking the private backyard, and a beautifully remodeled chef’s kitchen featuring quartz countertops, custom soft-close cabinets, stainless appliances, and a Ruvati workstation sink. The oversized primary suite includes a tray ceiling, walk-in closet, soaking tub, dual vanities, and a large tiled shower. A second ensuite bedroom functions perfectly as an in-law suite or private guest retreat. All bedrooms are generously sized, and the home has been updated throughout with quality finishes. Step outside to a 33' covered and screened lanai, a heated 30x15 in-ground pool, and a fully fenced backyard with a powered SmithBuilt workshop/shed. Major upgrades include: roof (2019), whole-home replumb (2019), AC handler (2019), kitchen remodel (2021), flooring (2021), pool heater (2022), variable-speed pump (2024), irrigation system (2024), and guest bath remodel (2025). Located less than a 2-minute walk to the Lake Summit boat ramp, offering direct access to the Winter Haven Chain of Lakes for boating, skiing, and fishing. Minutes to Legoland, shopping, dining, medical facilities, and convenient routes to both Orlando and Tampa. A beautifully updated home with no HOA, excellent flexibility, and impressive value at its new price!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Christina Loesch (347-977-0962)
2968 PLANTATION RD, WINTER HAVEN, FL 33884
$442,00045 Days on yellowkey MLS ID: P4938120
REDUCED by $23,000 (4.9%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1997Monthly Fee: $149 Tax: $3,191 (2025)Community: Cypresswood PlantationsSingle Family
Taxes:$3,191
Remarks: Enjoy serene golf-front living in this beautifully designed 2BR/2BA home, featuring two versatile bonus rooms perfect for a media room, home office, or guest space. This home features an irrigation well for watering the beautiful landscaping, and inside, there is an emergency whole-home Generac generator system! There is also a nice gas fireplace in the living area. Located in a desirable guard-gated golf-course community with a restaurant, pool, and tennis courts, this home combines comfort, space, and lifestyle. The open, spacious floor plan is ideal for everyday living and entertaining, with an expansive screened porch overlooking the golf course and peaceful pastureland, offering exceptional privacy and views. The primary suite is a true retreat, complete with a screened sitting porch overlooking the water, a spa-like bath with a jetted tub, a walk-in shower, a double vanity, and a bright solarium. The kitchen is well-appointed with a walk-in pantry and built-in shelving, while the large laundry room includes a utility sink and ample cabinetry. An oversized 3-car garage with additional storage cabinets completes the package. First time on the market, a rare opportunity to enjoy relaxed, resort-style living with plenty of flexible space!
Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)
Listing Agent: Joshua Taylor (863-651-5471)
5393 SAN PIETRO DR, WINTER HAVEN, FL 33884
$409,2454 Days on yellowkey MLS ID: TB8503618
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3016 Built: 2026Monthly Fee: $53 Tax: $4,690 (2025)Community: Villa MarSingle Family
Taxes:$4,690
Remarks: Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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)
4 GROVE CT SE, WINTER HAVEN, FL 33884
$429,9004 Days on yellowkey MLS ID: O6401108
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 1983 Built: 1977 Tax: $2,779 (2025)Community: Lake Winterset AcresSingle Family
Taxes:$2,779
Remarks: One or more photo(s) has been virtually staged. STUNNING POOL HOME ON OVERSIZED .53-ACRE CUL-DE-SAC LOT WITH NO HOA! Experience the perfect Florida lifestyle in this beautifully updated 4-bedroom, 2.5-bathroom residence. Perfectly positioned at the end of a quiet cul-de-sac, this home offers rare privacy and modern comfort. KEY UPGRADES: Move in with peace of mind featuring a RECENTLY REPLACED ROOF, UPDATED AC SYSTEM, NEW POOL PUMP,and modernized ELECTRICAL AND PLUMBING systems. The property has been FULLY REPAINTED inside and out for a fresh, contemporary look. INTERIOR ELEGANCE: The functional floor plan includes a formal LIVING ROOM and a spacious FAMILY ROOM centered around a cozy DOUBLE-SIDED WOOD-BURNING FIREPLACE. The kitchen boasts NEW STAINLESS STEEL APPLIANCES, and ALL BATHROOMS HAVE BEEN COMPLETELY REMODELED with stylish finishes. OUTDOOR OASIS: Relax in your private SCREEN-ENCLOSED POOL, ideal for entertaining. The massive .53-acre backyard provides endless room for activities, while the rare 3-CAR GARAGE offers ample space for vehicles and storage. LOCATION HIGHLIGHTS: JUST 5 MINUTES (1.6 MILES) FROM LEGOLAND FLORIDA RESORT! Tucked away in a private cul-de-sac with no through traffic, yet minutes from shopping and dining. READY TO MOVE IN and easy to show. Schedule your private tour today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Julian Carvajal, Llc (407-454-2632)
5122 KINSLEY DR, WINTER HAVEN, FL 33884
$422,94887 Days on yellowkey MLS ID: S5143312
2 Days Off yellowkey (back on 4/2/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3030 Built: 2026Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: Under Construction. The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You’ll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry, and optional additional cabinets. Upstairs, discover an airy loft, a convenient laundry, three secondary bedrooms, and a lavish primary suite boasting an expansive walk-in closet and a private bath. This plan also features a patio and a 2-car garage. SAMPLE PHOTOS. Actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).*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)
6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$469,000154 Days on yellowkey MLS ID: P4937082
1 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2045 Built: 2019Monthly Fee: $5 Tax: $4,742 (2025)Community: Lake Ashton West Ph Ii NorthSingle Family
Taxes:$4,742
Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained 3-bedroom, 2-bath home awaits. From the stone on the front elevation and bronze screened front entry to the 32’ x 18’ bronze screened veranda, the home impresses in every way. It is situated on a quiet cul-de-sac with views of a large pond and golf course in the distance. Step inside and you’ll immediately notice how clean, crisp, and welcoming the home feels, offering the perfect setting for both comfortable, relaxed living and gracious entertaining. Tasteful 18” x 18” tile flooring provides a uniform flow throughout the house. Plantation shutters adorn all windows. Six interior and 2 exterior veranda fans (total of 8 fans) are remote controlled, high-end Minka ceiling fans. The living room is accented by a coffered ceiling. The kitchen is highlighted by maple cabinets in Toffee color, and feature rollout trays, a corner lazy-susan, refrigerator cabinet and bump ups and bump outs. Identical cabinets and granite counters are found in both baths. The chef’s kitchen appliances are fingerprint resistant stainless steel. A large walk-in pantry offers ample storage space off the kitchen. Multiple pocket doors afford smooth flow room to room. The granite kitchen counters are accented with pendant lighting above the island. Identical cabinets with granite counter and desk/work area are located in the laundry room. Tranquil views from the living room, kitchen and expanded veranda are stunning. The master bath provides dual vanities, one with makeup station, and a spacious, glass-enclosed shower with custom fixtures. The garage features parking for two vehicles and a separate golf cart garage. In addition to the Green Home features built into the house, extra insulation was blown in the attic, providing added energy savings. Plus, the CDD DEBT IS PAID IN FULL on this property, saving you over $10,000! With so many outstanding features, this property must be seen in person to be appreciated. Beyond your doorstep, Lake Ashton’s unmatched amenities invite you to enjoy two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and so much more, ensuring an active and fulfilling lifestyle. This special property is the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)
Listing Agent: Brad Kirwan (863-280-0390)
5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$475,000308 Days on yellowkey MLS ID: P4935325
2 Days Off yellowkey (back on 4/25/2026)
REDUCED by $35,000 (6.9%) on 04/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2443 Built: 2008Monthly Fee: $5 Tax: $6,051 (2024)Community: Lake Ashton West Ph 01Spa: YesSingle Family
Taxes:$6,051
Tax Year: 2024
Remarks: Under contract-accepting backup offers. PRICE REDUCTION! MOTIVATED SELLER! With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites year-round outdoor enjoyment, framed by the beauty of Lake Ashton's natural surroundings. Ideally situated near Lake Wales and Winter Haven this home offers exceptional access to shopping and entertainment; medical facilities and restaurants. The spacious three-bedroom, two-bath layout includes a large den, ideal for a home office or flexible living space. The chef's kitchen features upgraded 42" cabinets, tiled backsplash, granite counter top and breakfast bar all designed for both form and function. The primary suite offers a spa-like escape with double vanities, a walk-in shower, a large soaking tub, separate water closet, and His and Her walk-in closets. Direct access from the PRIMARY SUITE to the outdoor living space is a BONUS. The outdoor living space is covered and screened to enhance the home's entertaining capabilities, creating a seamless flow between indoor and outdoor living. This ST. JOHN floor plan is a split plan home, which is desirable and spacious. Golf enthusiasts will appreciate the separate golf cart entry garage. Additional home features include: Travertine Flooring in the Living Areas (Bedrooms have carpet), Custom Shelving in the Den/Office with Glass Doors, Tray Ceiling in the Primary and Living Room areas, Sliding Glass Doors that Disappear into a Pocket in the Living Room and Beautiful Window Treatments, Floor outlets in the LR and MORE.... IT'S AS MUST SEE!!! Located in Lake Ashton, a 55+ community, residents enjoy access to a resort-style pool, fitness center, pickleball and tennis courts, and planned activities. Lake Ashton offers 2- 18 hole golf courses (Memberships Optional), Restaurant, Pro Shop and Eagles Nest. If you are seeking luxury, security and an active lifestyle, Lake Ashton could be your next home.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$434,900131 Days on yellowkey MLS ID: L4958092
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Spa: YesSingle Family
Taxes:$2,790
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2023
Remarks: Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Brian Surrency (863-204-4298)
3108 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$423,00077 Days on yellowkey MLS ID: L4959442
1 Days Off yellowkey (back on 4/28/2026)
REDUCED by $3,000 (0.7%) on 04/23/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2249 Built: 2004Monthly Fee: $25 Tax: $5,809 (2025)Community: Buckeye PointeSpa: YesSingle Family
Taxes:$5,809
Remarks: Under contract-accepting backup offers. Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Jp Phillips (863-670-7923)
4020 CARTERET DR, WINTER HAVEN, FL 33884
$419,90055 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
Elementary School: Chain O Lakes Elem
Middle School: Mclaughlin Academy Of Excellence
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)
132 BROAD ST, WINTER HAVEN, FL 33881
$469,00041 Days on yellowkey MLS ID: P4938236
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2672 Built: 2016Monthly Fee: $74 Tax: $3,868 (2025)Community: Hampton CoveSingle Family
Taxes:$3,868
Remarks: Welcome to this immaculately maintained 4-bedroom, 3-bathroom home with a spacious 3-car garage, perfectly situated in the highly desirable Country Club area of Northeast Winter Haven. Located within a gated community, this home offers both privacy and peace of mind. Backing up to an 11-acre jurisdictional wetland, the property provides complete rear privacy with a beautiful natural landscape—no rear neighbors, just serene views and tranquil surroundings. Inside, you’ll find a thoughtfully designed split floor plan with upgraded flooring, modern cabinetry, and stylish countertops throughout. The layout offers both functionality and comfort, ideal for those who love to entertain. Step outside to your private screened back porch retreat and fully fenced yard—perfect for relaxing evenings or weekend gatherings while enjoying the quiet, natural backdrop. This home truly combines luxury, privacy, and location—don’t miss the opportunity to make it yours.
1936 CROSSROADS BLVD, WINTER HAVEN, FL 33881
$495,00059 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)
3971 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$474,900168 Days on yellowkey MLS ID: P4936971
REDUCED by $5,000 (1.0%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2023 Built: 2014Monthly Fee: $17 Tax: $4,603 (2024)Community: Island LakesSpa: NoSingle Family
Taxes:$4,603
Remarks: Big Price Drops and Price to sell. Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Keith St. Onge (863-651-1397)
496 TERRANOVA ST, WINTER HAVEN, FL 33884
$449,00088 Days on yellowkey MLS ID: O6380041
REDUCED by $11,000 (2.4%) on 04/11/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2357 Built: 2004Monthly Fee: $56 Tax: $6,005 (2025)Community: Terranova Ph 02Single Family
Taxes:$6,005
Remarks: Single story POOL HOME ready for new homeowners! This home sits on just over a QUARTER ACRE LOT. Terranova is a GATED COMMUNITY nestled among the Winter Haven Chain of Lakes. Enjoy the HEATED POOL all year in your backyard Oasis. Screened in patio is great for enjoying the beautiful Florida weather. Fully fenced yard with double door gate so you can pull a small boat inside! ROOF 2022. HVAC 2013. Split floor plan features the primary bedroom and bathroom on one side of the home and three additional bedrooms and a full bath on the other. High ceilings. BRAND NEW PUBLIX GROCERY STORE is being built less than five minutes away! Walking trail within the community to Chain of Lakes Elementary School. Call to schedule your private showing today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
314 TERRANOVA BLVD, WINTER HAVEN, FL 33884
$425,00011 Days on yellowkey MLS ID: O6401702
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)
737 SANTA MARIA DR, WINTER HAVEN, FL 33884
$478,00012 Days on yellowkey MLS ID: P4938535
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 1993Monthly Fee: $46 Tax: $3,220 (2025)Community: Overlook EstatesSingle Family
Taxes:$3,220
Remarks: Already appraised for the listing price, this home is a great opportunity for massive savings every month on utility bills. Current owners typical electric bill in heat of summer is approx. $16 Solar panels WILL be PAID IN FULL by Sellers at closing. 4 BR/2.5 BA w/NEW ROOF 2025, NEW AC 2024. Durable porcelain wood plank-look floors throughout. Stone, wood burning fireplace in great room. Very private, screened 32 x 16 HEATED pool with large covered seating area, cabana bath, outdoor shower and and roomy storage. Well established, small gated community convenient to shopping, downtown WH, chain-of-lakes recreation. Easy going HOA. Pet friendly! Safe concrete block/stucco construction and NO CDD. Don't miss this opportunity to protect yourself from future electric rate hikes. It's move in ready!
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Julie Phillips (561-906-1118)
1151 CAREFREE COVE DR, WINTER HAVEN, FL 33881
$435,000161 Days on yellowkey MLS ID: TB8450979
REDUCED by $4,000 (0.9%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1734 Built: 1984 Tax: $4,375 (2024)Community: Carefree CoveSingle Family
Taxes:$4,375
Remarks: Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter Haven’s northern Chain of Lakes and has been completely renovated to include a brand new roof, 4-ton A/C, luxury vinyl plank flooring, interior / exterior paint, and new water heater all installed in 2025. The interior living area includes new fixtures, new front and rear sliding glass doors. The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a stunning view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It can include a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy views of boats cruising the lake, skiers cutting through the water, and bald eagles, ospreys, and herons scooping up fish! The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes new ceiling fan and a large closet. The garage has been converted into the 3rd bedroom which is oversized with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces, as well a new toilets, and exhaust fans. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features new screen in the pool cage, a brand new pool liner, with new multi-color LED pool light, as well as new light and fan fixtures on the back porch. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The boathouse, which includes a roll-up door has also been newly painted is wired with electricity and could also function as a workshop. It features new lights, a new side door. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Furnishings in listing are available for separate purchase. As a potential AirBnB, the unit currently sleeps 7 including the pull out couch in the living room, but could potentially sleep 10 with the addition of a second bed in the 3rd bedroom and a second pull out couch in the enclosed porch area.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
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