Location: Winter Haven , 33884
Do Not Show Listings
100 EL CAMINO DR #202, WINTER HAVEN, FL 33884
$64,900257 Days on yellowkey MLS ID: TB8418090
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1971Monthly Fee: $751 Tax: $302 (2024)Community: Orchid Spgs Vill 100 CondominiumCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$302
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Waterfront Serenity Meets Effortless Living in the Heart of Winter Haven. Step into a lifestyle where your biggest daily decision is whether to enjoy coffee overlooking the lagoon or take a refreshing dip in the heated community pool. Nestled on the second floor of the meticulously maintained 55+ Granada Building, Unit 202 is more than just a home; it’s your private sanctuary in the sought-after Orchid Springs community. A Layout Designed for Connection and calm. Experience an open-concept living and dining area bathed in Florida’s natural light. The expansive Florida Roomacts as your front-row seat to nature, offering tranquil water views and lush landscapes that make every sunset feel like a private event. The Primary Retreat: A generously sized suite featuring a massive walk-in closet for ultimate organization. Modern Flexibility: Enjoy the convenience of an elevator and on-site laundry, with the rare added potential to install your own in-unit washer/dryer hookup. Seamless Comfort: A brand-new AC system ensures year-round peace of mind. The Gold Standard of HOA Value. Rarely does an HOA work this hard for you. This "all-inclusive" lifestyle eliminates the stress of multiple bills, saving you hundreds monthly. High-Tech Package: Includes Premium Cable and High-Speed Internet (a $250/month value). Total Utility Coverage: Gas, water, sewer, and trash removal are all covered. Maintenance-Free: Pest control, exterior upkeep, and grounds care are included, so you can spend your weekends at the private park or the clubhouse instead of mowing the lawn. The Best of Winter Haven at Your Doorstep. Beyond the gates of Orchid Springs, you are minutes from the vibrant energy of downtown Winter Haven. Indulge in local favorites like Nutwood or LoveBird, explore the world-famous Chain of Lakes, or enjoy the convenience of being just a stone's throw from LEGOLAND® Florida. Claim Your Piece of Paradise. With a recently adjusted price of $64,900, this move-in-ready residence offers a rare combination of waterfront beauty and unbeatable financial value. Schedule your private tour today and discover why life is better at Orchid Springs.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Carlos Diez Cordova (813-694-6208)
6315 GROVE POINTE DR SE, WINTER HAVEN, FL 33884
$160,000170 Days on yellowkey MLS ID: P4936981
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1984Monthly Fee: $65 Tax: $867 (2024)Community: Garden Grove OaksManufactured Home
Taxes:$867
Elementary School: Garden Grove Elem
Remarks: This beautiful home is back on the market due to buyer financing falling through right before closing – no fault of the seller. The good news? The seller has already completed lender-required repairs, so the home is ready for a smooth closing! Welcome to 6315 Grove Pointe Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts a walk in closet and private en-suite bath with both a garden tub and separate shower. Step into the open-concept living space filled with natural light featuring spacious living and dining areas ideal for entertaining or family gatherings. The kitchen is equipped with updated appliances, reverse osmosis water purification system, ample counter space and plenty of storage. The home had a new membrane roof installed in 2021 with a gutter and roof maintenance yearly contract. Roof was just inspected 10/2025. Vinyl plank flooring throughout, updated appliances and electric drapes. Enjoy community amenities, friendly neighbors and the convenience of being just minutes from local shopping,dining, medical facilities,and Winter Haven's world-famous Chain of Lakes. With access to major highways,commuting to nearby cities like Orlando or Tampa is a breeze. Don't miss the opportunity to make this beautifully maintained home in Garden Grove Oaks your new home! Schedule your private showing today and experience all this property for yourself.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Anita Lowe (863-269-6461)
714 MAGNOLIA PL #714, WINTER HAVEN, FL 33884
$230,000184 Days on yellowkey MLS ID: P4936867
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1987 Tax: $2,724 (2025)Community: Winterset 03 A Condo Ph 01Condo
Taxes:$2,724
Tax Year: 2025
Remarks: Where Every Day Feels Like Vacation—Lakefront Condo! Desirable Upstairs condominium with unobstructed Lake Views. Welcome to your dream home! This stunning upstairs unit offers 2 Bedroom, 2 full bathrooms and a convenient 1-car garage! Enjoy breathtaking views of Winterset Lake from your home. The open floor plan is enhanced by skylights, providing ample natural light throughout. This home is perfect for both relaxation and entertaining. The spacious primary bedroom with ensuite bath. Wake to a beautiful view of Winterset Lake. 2nd bedroom is a great guest space or office. Enjoy your screened in Lanai with spectacular sunsets! Located in a resort-style community, you will have access to top-notch amenities including a Clubhouse, pool, spa, tennis courts, boat dock and fishing pier and direct lake access. Safety and peace of mind are ensured with a state-of-the-art security system controlling access to the community. Winterset is professionally managed and maintained. Experience the perfect blend of comfort and community in a highly desirable setting. A forever home or just a place to come to get out of the cold weather you will enjoy the tranquility and all the nature that Central Florida provides. Don't miss this opportunity. All measurements are approximate.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Laurie Nock (937-218-0031)
6133 GRAND OAKS DR SE, WINTER HAVEN, FL 33884
$140,00052 Days on yellowkey MLS ID: L4959932
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1234 Built: 1995Monthly Fee: $65 Tax: $1,039 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$1,039
Remarks: Priced to Sell! Fully furnished! Excellent opportunity in the desirable 55+ community of Garden Grove Oaks where you own your land and enjoy low HOA fees. Located at 6133 Grand Oaks Dr SE in Winter Haven, this home offers a great layout with spacious living and dining areas and plenty of natural light. The kitchen provides ample cabinet and counter space, and the primary bedroom includes a private en-suite bath. A second bedroom and bath provide space for guests or a home office. Enjoy relaxing on the screened porch overlooking the peaceful community setting.This home is being sold AS-IS and offers a fantastic opportunity for buyers looking to update and add their own personal touches. Garden Grove Oaks is a well-maintained community conveniently located near shopping, dining, medical facilities, and Winter Haven’s Chain of Lakes with easy access to major highways to Orlando and Tampa.Great value and priced for a quick sale — don’t miss this opportunity!
3025 SILVERADO TER, WINTER HAVEN, FL 33884
$235,000254 Days on yellowkey MLS ID: P4935949
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1281 Built: 1988Monthly Fee: $125 Tax: $1,918 (2024)Community: Cypress PondSingle Family
Taxes:$1,918
Remarks: THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect for walking or biking through beautifully maintained grounds. This home enjoys serene views of the golf course, pond, and stunning sunsets—plus a front-row seat to Legoland’s nightly fireworks. Inside, you’ll find cathedral ceilings, abundant natural light, a split-bedroom layout, and an eat-in kitchen. The laundry room is conveniently located off the kitchen. The screened lanai, featuring new lighting and a ceiling fan, is the perfect spot to enjoy your morning coffee or relax while taking in the wildlife and golf course views. Recent updates include a newer roof (2024), HVAC system, and upgraded electrical, giving you peace of mind. Cypresswood is one of Winter Haven’s most established and picturesque communities, making this home a rare opportunity.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Malak Hassani Benbachir (863-624-7266)
1678 LINZ CT, WINTER HAVEN, FL 33884
$258,50042 Days on yellowkey MLS ID: L4960316
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1158 Built: 2019Monthly Fee: $455 Tax: $3,009 (2025)Community: Vienna Square Ph 2CSingle Family
Taxes:$3,009
Remarks: BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Bryan Dicks (863-287-7851)
5163 KINSLEY DR, WINTER HAVEN, FL 33884
$339,999291 Days on yellowkey MLS ID: S5130838
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2077 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a shower and a separate soaking tub. A laundry room and a fourth bedroom with its own private bath complete the 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!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
1123 CYPRESS PT W, WINTER HAVEN, FL 33884
$1,150,000285 Days on yellowkey MLS ID: P4934938
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2713 Built: 1977Monthly Fee: $29 Tax: $6,114 (2024)Community: Cypress PointSingle Family
Taxes:$6,114
Remarks: ELEGANT POOL HOME ON CHAIN OF LAKES! Paradise awaits you at this fabulous lakefront residence that offers the ultimate in comfort, space and sunset views Thoughtfully designed for lake living and entertaining, the home captures the beauty of Lake Eloise from both, inside and out. This home is situated on .72 acres with fencing, dock, boathouse and on a quiet cul de sac. Inside this spacious residence are 3 bedrooms, 3.5 baths, formal rooms and plenty of relaxed living space. The handsome two-story entry hall features a beautiful staircase and Mexican tile flooring. This foyer is flanked by the formal living room and formal dining room, both showcasing gorgeous wood floors and fabulous millwork of chair railing, crown molding and finish work, all of which continues throughout much of this custom home. The wonderful kitchen boasts beautiful wood cabinets, including pantry-style, a center island w/seating, gorgeous granite counters, stainless appliances, a desk area with bookcase and handy pass-throughs to the casual dining room, family room and the lanai. An impressive family room is perfect space for family and when entertaining guests as it presents meticulous mill work, a warm fireplace, wet bar, durable, attractive Mexican tile flooring, with access to the lanai, spacious pool area and amazing view across Lake Eloise. A lovely guest bedroom is adjacent to the family room and a full bathroom with an attractive tile shower and stone countertop vanity. The second level of the home houses two, spacious master en suites situated on either side of a bonus room that is ideal as den or office. The primary master’s suite has a wonderful view of the lake and an elaborate layout with his and her dressing rooms that include remarkable wardrobes and closet systems; this suite has a luxurious bathroom outfitted with hydro-spa tub, extraordinary walk-in shower with multi-spray heads and bench, plus a lengthy dual sink vanity. The additional upstairs en suite has a large walk-in closet, single sink vanity and a tile walk-in shower. A special room-with-a-view is the library/reading room that is adjacent to the bonus room; the wall of windows gives a panoramic view across the property and lake. The back lanai, patio and pool area is a true highlight that is perfect for relaxation or entertainment. Here, you’ll find an outdoor kitchen, heated pool & spa creating a serene setting for lounging, swimming, or hosting gatherings with friends and family. Outdoor enthusiasts will delight in the lakefront provisions of the fishing dock and boathouse with lift and metal roof; spend the day out fishing and boating or enjoy a sunset cruise throughout the Winter Haven Chain. Don’t miss this exceptional opportunity to embrace a lifestyle of elegance, convenience in your own slice of paradise of Central Florida! Call today for a private tour of the home and property.
Listing Agent: Erin Floyd (863-412-2286)
5125 SYLAS JAX AVE, WINTER HAVEN, FL 33884
$265,90036 Days on yellowkey MLS ID: L4960626
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1358 Built: 2025Monthly Fee: $18Community: VillamarSingle Family
Remarks: New construction home with 1358 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a raised bar, fully open to the 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 private en-suite bath, a tiled shower. Plus, enjoy a covered lanai, 1-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 decor do not convey."
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
144 MORNING GLORY CIR, WINTER HAVEN, FL 33884
$299,90036 Days on yellowkey MLS ID: P4938259
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1433 Built: 2006Monthly Fee: $160 Tax: $3,265 (2025)Community: Morningside At WintersetSingle Family
Taxes:$3,265
Remarks: Welcome to the beautiful waterfront resort-style gated community of Winterset. ! Enjoy the charming 3-bedroom, 2-bathroom home offering a delightful living experience. Built in 2006, this well maintained home is move in ready. The open floor plan seamlessly connects the main living areas, creating a spacious and airy feel throughout. The master bedroom is a serene retreat, complete with ample space, a walk-in closet, and an en-suite bathroom. The additional two bedrooms available for a home office, a guest room, or a personal hobby spa. . Enjoy the resort-style amenities that make this community truly exceptional. The clubhouse serves as a gathering place for residents. The sparkling pool and hot tub invite you to take a refreshing. Bring your boat- ramp available for enjoying Winter Haven’s famous chain-of-lakes.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Sharon Watson (863-557-4800)
1509 COVEY RISE TER, WINTER HAVEN, FL 33884
$357,83545 Days on yellowkey MLS ID: W7883981
4 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2021 Built: 2026Community: Ashton CoveySingle Family
Taxes:
Tax Year:
Remarks: Under Construction. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Panama single-family home is what you always pictured for yourself. Step in from the 2-car garage or front porch and pass the first of 3 spacious bedrooms and a full bath with double vanity. A versatile flex space upgraded to a study. In the dining area, prepare to be wowed. This space is highlighted by a gourmet kitchen with a large island overlooking a lanai and a great room where friends and family will gather. Your luxurious owner’s suite includes a beautiful tray ceiling, a double vanity owner’s bath and a huge walk-in closet. The Panama is pure bliss. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.
Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)
Listing Agent: Bill Maltbie (813-819-5255)
1114 BRIMSTONE CIR, WINTER HAVEN, FL 33884
$399,00037 Days on yellowkey MLS ID: O6392519
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2476 Built: 2024Community: Harmony/Lk Eloise Ph 1Single Family
Remarks: Welcome to Harmony at Lake Eloise, a thoughtfully crafted community in the heart of Winter Haven, designed for homeowners who want modern style and smart features. A beautifully designed floor plan offering open concept living, flexible spaces, and contemporary finishes. The home centers on a stylish kitchen with Shaker cabinetry and stainless-steel Whirlpool appliances, creating the perfect setting for everyday living and effortless entertaining. Built with long-lasting quality in mind, homes feature block-on-block construction, architectural shingles, and timeless stucco exteriors. The largest lot in the community. The open floor plan connects the foyer with a spacious great room and dining area, ideal for entertaining or family gatherings. The kitchen features solid-surface countertops, stainless steel appliances, a disposal, and thoughtful layout for everyday meal prep and hosting. The owner's suite includes a spa-style bathroom and walk-in closet; other bedrooms are generous in size and brightness. A dedicated loft space with scenic window views offers the perfect spot for relaxation or a home office. Eco-conscious tenants will appreciate the solar power system, which contributes to energy savings, and a modern security camera system for peace of mind. With a quiet and good-sized lot, perfect to enjoy Florida weather. Inside, integrated smart home technology brings added convenience, comfort, and peace of mind. The community boasts a state-of-the-art, two-story amenity center, an impressive hub for recreation, relaxation, and connection. Residents will also enjoy private boat slips with direct access to Lake Eloise, offering a true Central Florida lifestyle on the water. Harmony at Lake Eloise is where modern living, exceptional amenities, and a connected location come together. Beyond the interiors, residents can enjoy the tranquil surroundings of Lake Eloise, where outdoor activities abound. Whether you prefer strolls along the water or engaging in recreational activities, this community offers a wealth of opportunities to connect with nature. Located in the master-planned community of Harmony at Lake Eloise, residents currently enjoy access to a community pool, sidewalks throughout the neighborhood, walking paths around scenic ponds, and a designated bike accessway. Future community plans include a proposed lakefront amenity center on Lake Eloise and a planned commercial area with neighborhood shops (subject to development timelines and approvals). Conveniently located near LEGOLAND Florida Resort, the AdventHealth Fieldhouse and Conference Center, and the Freedom Boat Club Winter Haven Lake Eloise location, offering an additional boating lifestyle option by membership. Additional sports and recreation facilities are planned nearby, including four collegiate-level baseball fields projected to generate economic activity for the City of Winter Haven (publicly discussed development plans). Cypress Junction Montessori is planned nearby and is currently accepting enrollment for 2026. Polk County has begun clearing and dredging efforts at nearby Lake Lulu, with discussions suggesting a future canoe and kayak launch and park area (subject to county completion and final designation). With continued infrastructure investment, future recreational access to the Chain of Lakes is anticipated in some form, subject to approvals. Discover the harmony of life at Lake Eloise today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Sean Flatley (609-208-8204)
2935 PLANTATION RD, WINTER HAVEN, FL 33884
$598,90037 Days on yellowkey MLS ID: L4959891
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2724 Built: 1983Community: Cypresswood PlantationSingle Family
Remarks: Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a formal living room and an open-concept family room, dining area, and kitchen, creating a bright and inviting atmosphere ideal for both everyday living and hosting. Also features granite countertops, resurfaced garage, private office, freshly painted interior, paver driveway, and so much more. Enjoy the comfort, privacy, security, and lifestyle that come with living in one of Winter Haven’s premier golf communities.
Listing is courtesy of: LBJ REALTY AND ASSOCIATES LLC (863-206-1552)
Listing Agent: Lovett Johnson (863-206-1552)
543 TERRANOVA CIR, WINTER HAVEN, FL 33884
$399,90060 Days on yellowkey MLS ID: L4959863
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2118 Built: 2003Community: Terranova Ph 01Single Family
Remarks: POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!
Listing Agent: Steve Lockhart (863-289-9801)
5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$420,000249 Days on yellowkey MLS ID: P4936039
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2031 Built: 2015Community: Lake Ashton West Ph 01Single Family
Remarks: HUGE PRICE ADJUSTMENT — MOTIVATED SELLER! Welcome to this beautifully, open-concept Sebastian model FULLY FURNISHED and TURNKEY, allowing you to settle in and start enjoying the Lake Ashton lifestyle from day one. Grand, high ceilings immediately draw your eyes to the serene 17th-hole golf view, offering a peaceful backdrop perfect for relaxed living. The living room is anchored by a stunning wood entertainment center with glass display, complemented by plush leather recliners ideal for unwinding or hosting friends. Recessed lighting, neutral tones, and crown molding create a warm, inviting ambiance throughout the home. This home features tile flooring throughout the main living areas, thoughtfully selected furnishings in every room, and a second bedroom equipped with a medical bed for guests or caregiving needs. The gourmet kitchen includes 42" wood cabinetry with crown molding, granite countertops, a stylish backsplash, pendant lighting, Whirlpool stainless steel appliances, and under- and over-cabinet lighting. A washer and dryer are also included for easy, everyday living. The primary suite offers a peaceful retreat with a walk-in closet, dual granite vanities, and a walk-in shower with a corner seat. Triple sliders open to an extended screened veranda, perfect for morning coffee, evening breezes, or simply enjoying the tranquil golf course setting. The Garage is equipped with storage, a golf cart, a leisure bike, and a garage privacy screen, making it easy to embrace the active lifestyle of Lake Ashton. Just unpack and begin enjoying the community, offering two gated entrances with 24/7 guard service and access to two clubhouses featuring a grand ballroom, movie theater, bowling lanes, and on-site dining at Charm City and Eagle Nest. Stay active with amenities including indoor and outdoor pools, fitness centers, racquetball, tennis, pickleball, bocce, shuffleboard, and more.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Candra Alston (407-257-5204)
831 ORCHID SPRINGS DR ##831, WINTER HAVEN, FL 33884
$115,000135 Days on yellowkey MLS ID: L4957905
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 851 Built: 1987Community: Rosewood ManorCondo
Remarks: Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!
Listing is courtesy of: CLARK REALTY LLC (863-345-2155)
Listing Agent: Steven Perkins (863-797-7276)
3905 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$310,00037 Days on yellowkey MLS ID: P4938216
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1729 Built: 2005Community: Osprey PointeSingle Family
Remarks: Located in Osprey Pointe on Lake Ned, 3905 Osprey Pointe Cir. is everything you've been looking for in the heart of Central Florida. This 3 bed, 2 bath home was built to last and withstand anything that comes it's way. Using solid poured concrete tilt walls, the house is incredibly strong and comfortable. Offering over 1700 square feet of air conditioned space, you will never feel confined. The family room, kitchen and dining area have soaring vaulted ceilings, while the primary bedroom feels spacious with a beautiful tray ceiling. The kitchen has many upgrades including solid cabinets, granite counter tops and a natural gas range. You'll also have access to the community clubhouse, pool and dock. With a location just minutes from great shopping, restaurants, grocery stores, medical facilities and Legoland! This home is in great shape and has a wonderful location. It will not last long, come see it before it's gone.
Listing is courtesy of: STRAIGHT UP REALTY & PM LLC (863-698-7547)
Listing Agent: Cole Bataille (863-698-7547)
12 BRIDGEWATER DR, WINTER HAVEN, FL 33884
$440,00062 Days on yellowkey MLS ID: S5144703
0 Days Off yellowkey (back on 3/6/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2369 Built: 1990Community: BridgewaterSingle Family
Remarks: Under contract-accepting backup offers. Welcome home to this fabulous 3 bedroom, 3 bath water front pool home nestled in the desirable Bridgewater community. The home is located on the infamous "WINTER HAVEN CHAIN OF LAKES" on the canal between lake Eloise and the cleanest spring fed lake on the chain, LAKE WINTERSET. BRIDGEWATER IS AN ESTABLISHED COMMUNITY OF 22 CUSTOM BUILT HOMES. With access to a private community boat ramp, and newly renovated COMPOSITE dock for your boating and fishing pleasure. Lake Winterset often offers a SLALOM COURSE for the water skiing enthusiast. This fabulous brick home will have a BRAND NEW REROOF with ARCHITECTURAL SHINGLES, peel and stick UNDERLAYMENT installed over the next two weeks for the new owners peace of mind. The new roof will have a ten year transferable warranty to the new owner. As you enter this amazing home you'll be greeted by the grand foyer with vaulted ceilings, and an amazing view of the wood burning brick fireplace in the sunken great room with wooden floors, BLENDING RETRO CHARM WITH MODERN COZY FUNCTIONALITY. There are two sets of French doors exiting to the outdoor kitchen pool area from the great room with amazing views. As you turn to the right, you step inside the amazing study with wooden floors which can easily be transformed into a formal sitting room. Boasting over 2,369 square foot of living space there is plenty of room in this oversized kitchen and dining area to entertain your guest and sliding doors to exit to the pool area. The custom made plantation shutters in the dining area, convey with the home. The large primary bedroom has its own sliding doors that exit to the fully enclosed screen pool and outdoor kitchen area and TWO LARGE WALK IN CLOSETS. The primary bathroom has dual vanity sinks and a large garden jet tub with separate walk in shower stall. Enjoy cooking and entertaining in your fully screened in lanai with an outdoor kitchen area while taking in the sights and sounds of nature on this freshwater canal, AND CASCADING WATERFALL FROM THE SPA INTO THE HEATED POOL. The community of Bridgewater has its own PRIVATE BOAT RAMP LAUNCH and newly renovated dock for unlimited usage to its residents that wish to boat or fish just a few feet from their front door. The home is equipped with two air condition units one replaced 2 YEARS AGO and the other 5 YEARS AGO. Both front loader, washer and dryer convey inside this large indoor laundry room. The two car garage door was insulated for more energy efficient climate control. The home is located just 2.3 MILES FROM THE GATES OF LEGOLAND and just 2.5 MILES FROM SHOPS RESTARUANTS AND MEDICAL FACILITIES making this location ideal. Schedule your viewing today.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Eric Sigismondi, Llc (863-651-9257)
4223 SAN ROCCO WAY, WINTER HAVEN, FL 33884
$325,000190 Days on yellowkey MLS ID: S5137072
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2522 Built: 2023Community: Villamar Ph 5Single Family
Remarks: One or more photo(s) has been virtually staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and connection. The kitchen shines with stainless steel appliances, an oversized pantry, and cabinets with updated fixtures, all opening to the main living area with NEW laminate flooring—creating a seamless space for gathering and entertaining. A bedroom and full bathroom on the main floor offer ideal flexibility for guests or multi-generational living. Upstairs, you’ll find four additional bedrooms, a loft that’s perfect for a home office or a cozy nook to unwind and recharge, and a conveniently located laundry room. The oversized primary suite features a large walk-in closet and an ensuite bathroom complete with a stand-alone shower, upgraded shower head, and linen closet for added convenience. Step outside to a fully fenced backyard, offering privacy and plenty of space to create your own outdoor retreat—whether that means adding a future pool, garden, or simply enjoying a quiet evening of relaxation. The oversized under-the-stairs storage and two-car garage add even more practicality, while the LOW HOA helps keep ownership easy and affordable. Perfectly situated just off US-27, residents enjoy proximity to dining, shopping, and grocery options, as well as easy access to I-17. Outdoor enthusiasts will love being near the Winter Haven Chain of Lakes, ideal for boating, kayaking, fishing, or simply soaking up the sunshine. Plus, the charming Downtown Winter Haven Historic District is nearby—home to local restaurants, boutiques, and community events like First Fridays, the Wine, Chocolate & Cheese Festival, and so many more! For a weekend of fun with the family and friends, LEGOLAND is only 3.5 miles away! This home beautifully blends modern comfort, functional space, and a convenient location—making it a must-see in the heart of Winter Haven. This is the one you've been waiting on. Schedule a showing today and make it yours!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Brianna Perez Montalvo (407-687-3837)
2270 FIRESTONE PL, WINTER HAVEN, FL 33884
$185,000162 Days on yellowkey MLS ID: TB8440562
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1439 Built: 1984Community: Cypresswood Golf Villas Gi-4Villa
Remarks: Welcome to this well-kept home in the highly sought-after Cypresswood Golf and Country Club, a gated community known for its beautiful grounds and exceptional amenities. Inside, you’ll find bright, open living spaces that flow seamlessly from the living room to the dining area and kitchen, creating a warm and functional layout for everyday comfort. The kitchen offers ample cabinetry and a practical design, while the bedrooms provide generous space and a relaxing atmosphere. The bathrooms are clean, comfortable, and thoughtfully maintained. At the front of the home, a charming courtyard gives you a private spot to unwind or personalize with your own touches. Residents of Cypresswood enjoy access to golf, tennis, and an on-site clubhouse restaurant, all within a peaceful, well-established community. With convenient access to Winter Haven’s shops, dining, lakes, and major roadways, this home offers a perfect blend of comfort, lifestyle, and location.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Darin Dobson (407-947-6773)
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