Location: Winter Haven , 33884
Do Not Show Listings
3151 LAUREL OAK LN, WINTER HAVEN, FL 33884
$346,55544 Days on yellowkey MLS ID: L4961605
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2029 Built: 2026Monthly Fee: $18Community: VillamarSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$0
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under Construction. New construction home with 2029 square feet one-story including 4 bedrooms, 2.5 baths, and an open living area. Enjoy an open kitchen with shaker-style cabinets with crown molding, granite countertops, Samsung stainless steel appliances, pantry, and a spacious counter height island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Jack-and-Jill hall bath with an enclosed tub and toilet, accessed from bedrooms 3 and 4. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey."
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
5121 SYLAS JAX AVE, WINTER HAVEN, FL 33884
$308,17044 Days on yellowkey MLS ID: L4961604
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1568 Built: 2026Monthly Fee: $18Community: VillamarSingle Family
Remarks: Under Construction. New construction home with 1568 square feet on two-story including 3 bedrooms with loft, 2.5 baths, and an open living area. Enjoy an open kitchen, Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a bathroom. Plus, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not
1798 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884
$298,900124 Days on yellowkey MLS ID: TB8476320
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1526 Built: 2025Monthly Fee: $90Community: Peach CrossingsSingle Family
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year: 2024
Middle School: Denison Middle
Remarks: Welcome to Peach Crossings, a brand-new community in Winter Haven! This beautiful three-bedroom, two-bathroom home is designed with both comfort and style in mind. The kitchen is a true highlight, featuring expansive counter space, perfect for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The combination of granite countertops and crisp white cabinetry creates a timeless and elegant look. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy outdoor living on the covered patio, an ideal space for relaxing, dining, or enjoying the Florida weather. This home also comes with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for modern convenience. A mudroom just off the garage provides a functional space to store shoes, bags, and coats, helping to keep the home organized. Conveniently located next to the laundry room, this area makes everyday tasks easier. Located in the heart of Polk County, Peach Crossings offers the perfect balance of peaceful lake living with easy access to shopping, dining, and local attractions. Families will appreciate the top-rated Polk County schools, and the community features a children’s playground and a picnic area for all to enjoy. Don’t miss this opportunity—schedule your showing today!
Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)
Listing Agent: Gayle Van Wagenen (904-449-3938)
1783 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884
$409,90062 Days on yellowkey MLS ID: TB8498625
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2244 Built: 2025Monthly Fee: $95Community: Peach CrossingsSingle Family
Remarks: Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home situated on a desirable corner lot with no rear neighbors, offering extra privacy and an open feel. As you step inside, a long and inviting foyer welcomes you into the home. The first floor boasts a bright and open family room, perfect for gathering, along with a modern kitchen featuring a large island, breakfast bar, and brand-new Whirlpool appliances. A guest bedroom and a full bathroom on the main level provide a comfortable space for visitors or a private home office. Upstairs, the master retreat offers plenty of space for a king-sized bed, a dresser, and even a cozy reading nook. The en-suite bathroom includes a dual sink vanity, a linen closet for added organization, and a spacious walk-in closet for all your storage needs. The four additional bedrooms are generously sized, allowing everyone their own private space. These rooms can also be used as a home office, playroom, or hobby room to suit your lifestyle. With three full bathrooms, mornings run smoothly without congestion. A large upstairs laundry room with ample storage and a dedicated closet adds to the home’s convenience. Step outside and enjoy the covered back patio and covered front porch, perfect for relaxing or entertaining outdoors. Located in the highly sought-after Peach Crossings community, this home offers easy access to top-rated Polk County schools, shopping, dining, and local attractions. With all upgrades included, this home is move-in ready! Schedule your private showing today!
273 HAYLEY ST, WINTER HAVEN, FL 33884
$240,000145 Days on yellowkey MLS ID: O6375357
5 Days Off yellowkey (back on 5/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1432 Built: 2024Monthly Fee: $16 Tax: $6,815 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$6,815
Remarks: Under contract-accepting backup offers. Short Sale. Exceptional Corner-Lot Home in Peace Creek Reserve. A beautifully maintained, move-in ready 3 bedroom, 2 bath home. Just a short stroll from the resort-style pool and playground, this home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is ideal for entertaining, highlighted by a gourmet kitchen with a spacious center island overlooking the dining area and expansive family room. Ceramic tile flows throughout the main living areas, while upgraded carpeted bedrooms provide cozy retreats. Unwind in the oversized owner’s suite, featuring a spa-inspired bathroom with dual vanities and a generous walk-in closet. This home stands out with included stainless-steel appliances, solid surface countertops, window blinds, LED recessed lighting, ceiling fans, and more—features often considered upgrades elsewhere. Ideally located near Winter Haven’s renowned Chain of Lakes, enjoy kayaking, paddleboarding, or pontoon boat rentals on scenic waterways. Just minutes from LEGOLAND®, local restaurants, farmers markets, bike paths, and a variety of entertainment options, this home delivers both lifestyle and location.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bob Bretz, Pa (407-797-9500)
2656 WYNDSOR OAKS WAY, WINTER HAVEN, FL 33884
$750,00050 Days on yellowkey MLS ID: TB8501985
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3703 Built: 2007Monthly Fee: $267 Tax: $9,056 (2025)Community: Wyndsor At Lake WintersetSpa: NoSingle Family
Taxes:$9,056
Elementary School: Chain O Lakes Elem
High School: Winter Haven Senior
Remarks: Discover refined living in Wyndsor at Lake Winterset, one of Winter Haven’s premier gated communities. Set on a half-acre lot, this beautifully maintained 5-bedroom, 5-bathroom residence blends timeless craftsmanship with thoughtful updates and an impressive amount of living space. Step inside to soaring ceilings, architectural arches, decorative pillars, crown molding, and tray ceilings that create an immediate sense of grandeur. The formal living and dining rooms flow effortlessly into the main living areas, where 16x16 tile and luxury plank vinyl flooring with water-proof add both style and durability. The spacious kitchen is designed for everyday living and entertaining, featuring a large island, stainless steel appliances, and built-in oven and microwave. It opens to a warm and inviting great room complete with a gas fireplace and custom built-ins. A dedicated office and two additional living areas provide flexibility for work, relaxation, or extended generations. The primary suite is a private retreat with a double-door entry foyer, two walk-in closets, and room for a sitting or desk area. The spa-like en-suite bath includes a dual-head shower, Jacuzzi tub, granite counters, double sinks, and a separate vanity. Four additional bedrooms — each with its own private bath — are thoughtfully positioned on the opposite side of the home for maximum privacy. The upstairs suite offers versatility as a second primary, media room, or game room. Enjoy Florida living on the expansive 1,000 sq ft screened lanai, fully under roof and pre-plumbed and wired for an outdoor kitchen. Excellent for quiet evenings or large gatherings. Additional highlights include a 3-car garage with storage room and a tankless hot water system. Major updates include a new roof (2022) and two HVAC units (2017). Located minutes from Legoland and within easy reach of both coasts, major attractions, shopping, and dining, this home delivers luxury, space, and convenience in one of the area’s most desirable neighborhoods.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
1561 VIENNA SQUARE DR, WINTER HAVEN, FL 33884
$229,500579 Days on yellowkey MLS ID: P4932767
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1231 Built: 2014Monthly Fee: $430 Tax: $1,843 (2024)Community: Vienna SquareVilla
Taxes:$1,843
Elementary School: Elbert Elem
Remarks: R E D U C E D ... YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. THIS 2BR-2BA VILLA OFFERS AN OPEN GREAT ROOM DESIGN WITH SPLIT BEDROOMS. THE MASTER ENSUITE HAS WALK IN CLOSET WITH STEP IN SHOWER FOR CONVENIENCE. THE 2ND BEDROOM OFF FRONT ENTRANCE OF HOME HAS AN ADJOINING BATH WITH TUB AND SHOWER. DON'T WAIT, THIS GREAT GATED COMMUNITY HAS CLUBHOUSE, FITNESS CENTER, POOL, TENNIS COURTS AND OFFERS SO MUCH TO YOUR OVER 55 LIFESTYLE. CONVENIENT TO SHOPPING, RESTAURANTS AND ONLY MINUTES TO DOWNTOWN WITH SOMETHING FOR EVERYONE. THIS VILLA HAS AN OPEN FLOOR PLAN WITH HIGH CEILINGS, CEILING FANS, CERAMIC TILE IN THE LIVING AREA AND CARPETING IN THE BEDROOMS. RELAX ON YOUR ENCLOSED LANAI OVERLOOKING THE SERENE ATMOSPHERE OF THE PEACEFUL WOODED AREA BEHIND YOUR UNIT WITH NO REAR NEIGHBORS. THE MONTHLY HOA FEE INCLUDES EXTERIOR PAINT, ROOF, IRRIGATION WATER, LAWN MAINTENANCE AND RECENT ADDITION OF SPECTRUM TV/WIFI SERVICE. THIS VILLA HAS BEEN CLEANED AND READY FOR YOUR MOVE.
Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)
Listing Agent: Glenda Pruitt (863-412-2727)
2925 DAYTON DR, WINTER HAVEN, FL 33884
$284,500180 Days on yellowkey MLS ID: P4937324
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2109 Built: 2006Monthly Fee: $485 Tax: $2,954 (2025)Community: Traditions Ph 01Spa: NoSingle Family
Taxes:$2,954
Remarks: Discover the charm of this delightful 3-bedroom, 2-bath home located in the maintenance-free, 55+ gated community of Traditions at Lake Ruby. Thoughtfully designed for comfort and functionality, this home offers an inviting retreat for relaxed, worry-free living. Upon arrival, you’re welcomed by a spacious covered entrance enhanced with a leaded glass door and transom window. Inside, the eat-in kitchen features 42" maple wood cabinetry, Corian countertops, and a closet pantry for added storage. A breakfast bar and breakfast nook provide ample seating, making the space ideal for both everyday living and entertaining. The spacious great room showcases triple sliding glass doors that open to the oversized screened-in lanai, seamlessly extending the living space outdoors. The open-concept design also includes a formal dining room and formal living room, both accented with high ceilings and decorative niches that add architectural interest. The primary bedroom suite serves as a luxurious retreat, featuring a sitting area with patio access and dual walk-in closets with overhead luggage shelving for premium storage. The en-suite bathroom is well appointed with a comfort-height double-sink vanity, linen closet, seated walk-in shower, private water closet, and a relaxing garden tub. Outdoor enjoyment is effortless on the generously sized screened-in lanai, offering a serene space to unwind and enjoy the Florida lifestyle. Additional amenities include, a Laundry Room with washer, dryer, and utility sink, Honeywell Thermostat & Humidistat, Updated Architectural Shingle Roof 2020, Termite Bond, Paved Driveway & Walk Way, Gutters, Flood lights and Carriage Lighting, and a 2 Car Garage with Garage Door Opener. Residents of Traditions enjoy a plethora of amenities, including a lakefront clubhouse, a dock and boat ramp, a heated swimming pool and spa, a ballroom, billiards, meeting rooms, a library, a computer room, a craft room, a dog park, tennis and pickleball courts, basketball, bocce ball, shuffleboard, a fitness center, an aerobics studio, and much more. With its convenient location near shopping, restaurants, major routes, and Legoland, this home offers an exceptional lifestyle. Monthly HOA fees cover exterior house painting, cable, internet, lawn service, and clubhouse amenities, ensuring a worry-free living experience.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
14 ENCLAVE DR, WINTER HAVEN, FL 33884
$229,900316 Days on yellowkey MLS ID: P4935733
REDUCED by $10,000 (4.2%) on 05/01/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1995Monthly Fee: $429 Tax: $3,033 (2024)Community: Cypresswood Enclave Ph 01Villa
Taxes:$3,033
Remarks: Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven. The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer and dryer, screened lanai and a 2 car garage with garage door opener. Per the owner, recent upgrades include removal of a wall separating the kitchen from the living area thereby creating a true open-concept living area, upgraded matching stainless kitchen appliances, flooring in the kitchen, living room, foyer, hall and 2 bedrooms, New granite counter-tops, sinks and faucets in the kitchen and both bathrooms, new LED lighting, New front entry door, new window treatments and fresh interior paint. This is truly a move-in-ready villa with quality upgrades that set it ahead of the competition. Come and enjoy the Florida Country Club Lifestyle in this low maintenance villa.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steven Smith, Pa (863-224-2297)
204 KINGSHILL CT SE, WINTER HAVEN, FL 33884
$262,40070 Days on yellowkey MLS ID: O6393480
REDUCED by $7,500 (2.8%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1437 Built: 1991Monthly Fee: $8 Tax: $3,704 (2025)Community: Planters WalkSpa: NoSingle Family
Taxes:$3,704
Elementary School: Garden Grove Elem
Remarks: This move-in-ready 3-bedroom, 2-bathroom home is located in the desirable Planters Walk neighborhood. The interior features a functional open-concept layout where the kitchen overlooks the main living areas, creating an inviting flow for daily living and entertaining. The updated kitchen is equipped with sleek granite countertops and stainless steel appliances. The primary suite serves as a private retreat, complete with a dedicated primary bathroom and a large walk-in closet. Practical features include an attached 2-car garage, a separate laundry room, and a combination of carpet and tile flooring throughout.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
6010 NAVONA WAY, WINTER HAVEN, FL 33884
$279,99983 Days on yellowkey MLS ID: TB8490929
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $20,000 (6.7%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1615 Built: 2025Monthly Fee: $53 Tax: $2,689 (2025)Community: Villa MarSingle Family
Taxes:$2,689
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a laundry room located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. Our model home is located at 5512 Taverna Loop, Winter Haven, FL 33884. Take I-4 W to exit 55 for US 27-S. Continue on US 27-S then turn right onto Thompson Nursery Road. Continue straight on Eloise Loop Road then turn left onto Rialto Road. Continue straight and our model homes will be on your right. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
1665 TEAGAN LN, WINTER HAVEN, FL 33884
$210,00048 Days on yellowkey MLS ID: S5148760
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1060 Built: 2024Monthly Fee: $78 Tax: $5,853 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$5,853
Elementary School: Wahneta Elem
Middle School: Westwood Middle
Remarks: Welcome to your next chapter in beautiful Winter Haven! This charming home offers the perfect blend of comfort, convenience, and value—an ideal opportunity whether you're a first-time buyer, downsizing, or looking to invest. Step inside to discover a bright and inviting layout designed for everyday living. The home features well-proportioned living spaces filled with natural light, creating a warm and welcoming atmosphere from the moment you walk in. The kitchen offers ample cabinet space and functionality, perfect for both casual meals and entertaining guests. Enjoy relaxing mornings or peaceful evenings in your private outdoor space, with room to personalize and make it your own. Nestled in a desirable location, this property provides easy access to shopping, dining, schools, and major roadways—making your daily commute and errands a breeze. Offered at just $210,000, this is an incredible opportunity to own a home in a growing and sought-after area of Winter Haven. Don’t miss your chance to make this property yours—schedule your private showing today!
Listing Agent: Belkis Garcia (407-994-5885)
237 MCLEAN PT, WINTER HAVEN, FL 33884
$699,000226 Days on yellowkey MLS ID: L4957003
REDUCED by $21,000 (2.9%) on 04/30/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2961 Built: 2001Monthly Fee: $238 Tax: $6,631 (2024)Community: RenaissanceSingle Family
Taxes:$6,631
Remarks: MUST SEE! Beautiful Custom-Built Home in the Renaissance Subdivision! Welcome to your dream home nestled in the serene community of Renaissance in lovely Winter Haven, Florida. This stunning 4-bedroom, 4-bathroom model home offers the perfect blend of privacy, convenience, and resort-style living, complete with a spectacular pool area. Key Features: • Prime Location: Enjoy boat access to Lake Winterset in the chain of lakes and proximity to metro Orlando and Tampa, as well as attractions like Disney and Legoland. • Resort-Style Amenities: Full pickleball and basketball courts for active living and recreation. • Elegant Design: • Wide crown molding and baseboards throughout • 12-foot ceilings and 8-foot doors for an open and airy feel • Three sets of French doors leading to outdoor spaces • His and her walk-in closets for ample storage • Dedicated office space and formal dining room for entertaining Kitchen & Appliances: • Gourmet Kitchen: All stainless-steel kitchen appliances, including a 2022 French door refrigerator. • Smart Home Technology: Equipped with a Schlage keyless entry front door for added security and convenience. Security & Maintenance: • Advanced Security System: NASA security system with 5 cameras and motion sensors for peace of mind. • Irrigation System: 6-zone irrigation system with a separate well, updated in April 2025. Outdoor Oasis: • Salt Water Pool: Installed in 2021, with a new pool surface skimmer in 2025. • New HVAC System: Two 9-ton units refurbished in 2024, ensuring comfort year-round. • Natural Gas Tankless Hot Water Heater: Installed in 2020 for energy efficiency. • New Tile Roof: Installed in 2016, providing durability and style. • Flooring: New carpet, tile, and hardwood flooring installed in 2020. • Plantation Shutters: Added in 2020 for elegance and privacy. Waffle and Tray Ceilings: Transom windows enhance the natural light and aesthetic appeal. All windows were replaced in 2018 for energy efficiency. Additional Features: • Garage Storage: Gladiator metal garage storage system for organization. • Furniture Negotiable: Some furniture items may be negotiable for interested buyers. • Professional Landscaping: Newly updated landscaping in 2025 enhances curb appeal. This luxurious custom-built home is a true paradise waiting for you to call it your own. Don’t miss out on this incredible opportunity! Contact us today to schedule a viewing!
Listing Agent: Luis Perez Garcia (201-658-0689)
6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$469,000198 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)
2964 PLANTATION RD, WINTER HAVEN, FL 33884
$579,900244 Days on yellowkey MLS ID: O6352519
REDUCED by $20,000 (3.3%) on 04/30/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3614 Built: 1989Monthly Fee: $137 Tax: $618 (2024)Community: Cypresswood PlantationsSpa: YesSingle Family
Taxes:$618
Remarks: Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for privacy and connection. The primary suite is complete with dual vanities, walk-in closets, a garden tub, separate shower and private pool access. On opposite wing rests an en-suite bedroom, complete with full bath and independent access. Ideal for multigenerational living, guest privacy or an upscale in-law suite. Two additional bedrooms share a dual bath, while a half bath serves daily living or poolside use. Gourmet gathering begins in the kitchen, including a center island with gas range, generous counter space and views out toward the lanai. The breakfast nook offers a comfortable space for everyday dining, complemented by a nearby utility room and a flexible bonus room. Going outside, this home’s soul lives in its outdoor realm. A pool and spa, and a summer kitchen complete with built-in grill, sink and prep station, invite all-day alfresco living. A covered lanai frames those golf and pond vistas beautifully, offering shade and breeze for lounging or entertaining. Cypresswood is a full-amenity, guard-gated community with an 18-hole golf course, clubhouse with restaurant and lounge, tennis and pickleball, fitness/wellness center, and social programming. A $10,000 seller concession and one-year home warranty.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)
Listing Agent: Audrey Christman (516-547-5343)
3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$255,000163 Days on yellowkey MLS ID: S5141071
REDUCED by $10,000 (3.8%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1603 Built: 2006Monthly Fee: $210 Tax: $3,716 (2025)Community: Osprey PointeSingle Family
Taxes:$3,716
Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!
Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)
Listing Agent: Debbie Browning (407-908-9060)
20 BREVARD DR SE, WINTER HAVEN, FL 33884
$515,00055 Days on yellowkey MLS ID: L4961284
0 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2340 Built: 1976 Tax: $2,154 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$2,154
Remarks: Under contract-accepting backup offers. Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Don Jerue (863-259-9550)
5850 CYPRESS GARDENS BLVD #304, WINTER HAVEN, FL 33884
$139,000538 Days on yellowkey MLS ID: O6266648
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1332 Built: 1975 Tax: $1,531 (2023)Community: Royal Crescent CondoSpa: NoTownhouse
Taxes:$1,531
Tax Year: 2023
Remarks: Welcome to your new home located directly across the street From Legoland. Home features community pool and tennis court and is ready for a new owner. Located in the central Hub of Winter Haven and close to anything any everything you need. Shopping, restaurants, schools.
Listing is courtesy of: FLORIDA HOMES REALTY & MTG (904-996-9115)
Listing Agent: Matthew Davis (321-848-2004)
69 ENCLAVE DR, WINTER HAVEN, FL 33884
$300,00050 Days on yellowkey MLS ID: S5148089
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1682 Built: 1998Monthly Fee: $435 Tax: $2,189 (2024)Community: Cypresswood Enclave Ph 02Villa
Taxes:$2,189
Remarks: Welcome to 69 Enclave Drive, a beautifully updated home nestled inside the sought-after Cypresswood Golf & Country Club, a gated golf community known for its lush landscaping, resort-style amenities, and peaceful, secure atmosphere right in the heart of Polk County. From the moment you arrive, the manicured curb appeal sets the tone: mature palms, trimmed hedges, and a well-maintained façade with a two-car garage greet you at the entry. Step inside and you'll immediately notice the quality of every update, high-end laminate flooring flows throughout the home, complementing the fresh, modern palette and abundant natural light. The fully updated kitchen is a true showstopper, featuring custom raised-panel cabinetry, stunning granite countertops, a designer arabesque tile backsplash, and a full suite of stainless steel appliances, all included. A skylight above adds a bright, airy feel that makes cooking here a genuine pleasure. The spacious open-concept living and dining areas are designed for how Florida families actually live, wide open, light-filled, and flowing seamlessly toward the backyard through large sliding glass doors. The living room offers an ideal layout for entertaining, with a vaulted ceiling effect and views out to the lush, private backyard. Plantation shutters add a polished, upscale touch throughout. Bathrooms have been tastefully renovated with matching granite vanities, updated fixtures with brushed nickel hardware, and designer tile surrounds, all carrying that same cohesive, elevated look. The screened lanai is your private Florida retreat, perfect for morning coffee or evening sunsets, while the backyard offers mature trees, green space, and real privacy. An aerial view reveals just how spacious and private this lot truly is within the community. Practical updates make this home truly move-in ready: newer thermal windows for energy efficiency, a newer gas water heater, an updated laundry room with custom cabinetry, and a stunning epoxy-coated garage floor that gives the two-car garage a clean, finished look with room to spare. Living in Cypresswood means access to golf, a clubhouse, community pool, and the peace of mind that comes with a gated, well-managed neighborhood, all just minutes from shopping, dining, medical facilities, and major corridors serving the greater Central Florida area. Homes in Cypresswood at this level of finish don't last. Schedule your private showing today.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Manny Quiros (863-221-3036)
131 RUBY LAKE DR, WINTER HAVEN, FL 33884
$375,00070 Days on yellowkey MLS ID: P4938379
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1914 Built: 2000Monthly Fee: $71 Tax: $4,453 (2025)Community: Ruby Lake Ph 01Single Family
Taxes:$4,453
Remarks: One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest. Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A standout feature is the seamless connection to the outdoor space, with three separate access points to the 33x10 screened-in lanai, from the dinette, formal dining area, and primary suite—creating true indoor-outdoor living. The kitchen has been tastefully updated with brand new granite countertops, new range, and new microwave, along with ample cabinetry, a closet pantry, and breakfast bar. The primary suite is generously sized and opens into an en-suite featuring dual walk-in closets, split vanities, a garden tub, walk-in tile shower, and a private water closet. The split-bedroom floor plan offers privacy, while all bedrooms include walk-in closets. Recent improvements make this one stand out from others in the neighborhood, including brand new carpet throughout, fresh interior paint, and a new water heater, giving buyers peace of mind from day one. Located in the gated Ruby Lake community in Southeast Winter Haven, just minutes from convenient access to shopping, dining, Publix, Walmart, Legoland, and Hwy 27 for an easy commute.
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: Carlee Marchetti (863-258-3338)
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