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$249,900
2 Beds 2 Baths Cypresswood SubDv. 33884 Zip Code
BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed baseboard trim with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

$289,000
3 Beds 2 Baths Gardens Ph 01 SubDv. 33880 Zip Code
Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

212 Majestic Gardens Lane, Winter Haven

$549,999
3 Beds 3 Baths Lake Ashton West Ph Ii North SubDv. 33884 Zip Code
*GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The views from this coveted lot location are spectacular so make sure you bring your binoculars! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven

$106,000
2 Beds 2 Baths Lakeridge Condo SubDv. 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven

$370,000
4 Beds 3 Baths Overlook Estates East SubDv. 33884 Zip Code
HOME SWEET HOME! This sweet 4 bedroom 3 bath home is ready for its next happy homeowner. Located in a small gated community in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the homey kitchen with granite countertops and wood cabinets. The corner pantry can hold all your treats for those football weekend get togethers. The rooms have large windows offering abundant natural light, and space for everyone. The ideal 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with a PVC-fenced back yard, and extra storage in a charming 10x12 planters shed. The 2025 architectural shingle roof, 2017 AC dual zone AC system, and Generac generator have you covered in all Florida weather. Check out this sweet property today. Step inside, fall in love. Make it yours!

754 Santa Maria Dr, Winter Haven

$699,000
4 Beds 3 Baths Hart Lake Hills Ph 01 SubDv. 33884 Zip Code
From the moment you enter, it is immediately apparent this is not your typical lakefront home. Elevated sightlines extend across the pool to the tranquil waters of Hart Lake, creating a dramatic first impression and an almost infinity-edge style of living. Situated on approximately half an acre in the gated SE Winter Haven community of Hart Lake Hills, this immaculate custom residence offers 4 bedrooms, 3 baths and over 2,500 SF of refined living space with a level of finish and customization rarely found at this price point. Designed for upscale everyday living and impressive entertaining, the home showcases gorgeous travertine and wood flooring, substantial millwork, designer lighting, custom tile and stonework, granite surfaces and distinctive architectural details throughout. Statement fixtures incorporating sculptural, crystal and glass elements add another layer of sophistication. The open, triple-split bedroom floor plan includes a spacious family room, formal dining, office/den, kitchen with dinette and inside laundry. The family room captures panoramic lake views through expansive glass doors opening to the pool and features a custom wood TV wall accented with natural-edge detailing. The kitchen offers quartz countertops, stainless appliances, custom wood cabinetry, breakfast bar and a light-filled dinette overlooking the pool and lake. The adjoining dining room is illuminated by a dramatic faceted glass chandelier, while the office/den room provides flexibility as an office, study or additional sitting room. The primary suite features wood flooring, a large walk-in closet with built-ins and an extraordinary spa-inspired bath. Travertine and stone surround a floating-edge soaking tub with black stone deck, dramatic underlighting and sleek linear fireplace. An oversized open shower features multiple body sprays, handheld fixture and rainfall shower, complemented by floating cabinetry, granite-topped vanity, designer lighting and a private water closet. Three generously sized guest bedrooms are privately positioned away from the primary suite with excellent closet space and access to beautifully customized guest baths. The third bath also serves the pool and features a glass-enclosed MrSteam steam shower. Outside, wide steps transition from the elevated interior to an expansive screened outdoor living area where the saltwater pool appears visually connected to Hart Lake beyond. A large covered lanai with travertine flooring offers room for dining and lounging, while generous deck space provides plenty of room for entertaining and enjoying the Florida sunshine. Hart Lake offers opportunities for fishing, boating and enjoying the natural waterfront setting. Additional features include double-pane windows, insulated sliding doors, central vacuum, irrigation well, 2019 roof, 2020 A/C and a pool enclosure refurbished in 2024 with new screening, doors and screws. All this and centrally located between Tampa and Orlando, approximately 10 minutes from shopping, dining and medical facilities, and within walking distance of Chain of Lakes Elementary.

644 Hart Lake Drive, Winter Haven

$425,000
4 Beds 3 Baths Lake Mariam Hills Rep SubDv. 33884 Zip Code
Welcome home to this beautifully maintained four-bedroom, 2½-bathroom home located in a desirable gated community. New Roof installed along with a private access boat launch to Lake Mariam, perfect for enjoying Florida’s outdoor lifestyle. From the moment you walk through the front door, the home’s thoughtfully designed open floor plan immediately stands out. Your view leads straight through to the sparkling pool, creating a wonderful sense of space and bringing the outdoors in. The dining room is conveniently located to the right, while the spacious living room provides plenty of room for relaxing and entertaining. The kitchen features a large island with a breakfast bar, making it the perfect gathering spot for family and friends. Its open design allows you to prepare meals or wash dishes while still keeping an eye on the family enjoying the pool. Step outside to the expansive pool area, where there is plenty of space for outdoor dining, morning coffee, entertaining, or simply relaxing by the pool. It’s an ideal setting for enjoying the Florida sunshine year-round. The oversized master suite offers plenty of room to unwind and features a spacious master bathroom with a garden tub and dual vanity sinks. And there are some important recent updates to appreciate, including a new roof installed just one year ago and a new garage door. With its spacious floor plan, private lake access, boat launch, pool, oversized master suite, and recent improvements, this home offers the perfect combination of comfort, convenience, and Florida living—all within a gated community.

120 Lake Mariam Way, Winter Haven

$134,990
1 Beds 1 Baths Fairview Village SubDv. 33881 Zip Code
Welcome Home to Easy Florida Living! Come discover this beautifully maintained 2023 Skyline Park Model, installed in August 2022 and thoughtfully designed with comfort, convenience, and relaxation in mind. From the moment you arrive, you’ll appreciate the new concrete driveway, newer roof, central air, spacious storage, and inviting outdoor living opportunities. Inside, the home offers an open and comfortable layout with a large pantry, dining island, electric fireplace, walk-in shower, and a bedroom spacious enough for a king-size bed. The home is being offered with many furnishings and features, including a French-door refrigerator, electric range, microwave, washer/dryer combo, water softener, blinds, generator ready and more. The lifestyle is just as appealing! The 99-year perpetual lease is renewable for only $1, while the current $90 monthly association fee includes water, sewer, trash, seasonal lawn maintenance, heated pool access, clubhouse, and a variety of community activities. Enjoy shuffleboard, horseshoes, billiards, ping pong, and a community dock with direct canal access to Lake Henry, complete with a pier bench and fire pit. Whether you’re looking for a seasonal retreat, a comfortable Florida getaway, or a place to enjoy the relaxed community lifestyle, this one is ready for you to come see and fall in love with it! Financing Available!

7060 Fairview Village Circle, Winter Haven

$115,000
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
OVER $19,000 IN RECENT UPGRADES MEANS THE BIG-TICKET WORK HAS ALREADY BEEN DONE! This fully furnished Oakwood Estates home features a new roof (2023), plus new HVAC, electric water heater, rain gutters, and exterior porch tile (2024). Step inside to a bright, welcoming interior filled with natural light from double-pane windows. Luxury vinyl plank flooring flows throughout. The kitchen features stainless steel appliances, white cabinetry, wood-look countertops, and a newer sink. Built-in cabinetry adds charm and storage to the dining area, which opens to a spacious living room. Both bedrooms are generously sized, with a walk-in closet in the primary. A separate laundry room includes the washer and dryer. Enjoy additional living space in the Florida room and enclosed lanai, perfect for relaxing and enjoying the Florida lifestyle. Hurricane shutters, vinyl siding, and an updated electrical panel add even more value. Oakwood Estates is a gated, resident-owned 55+ community with two heated pools, two clubhouses, pickleball and tennis courts, shuffleboard, bocce ball, miniature golf, a fishing lake and pier, RV and boat storage, library, activities center, and an active social calendar. Major updates done, furnishings included, and ready for you to move in and enjoy!

4332 Cherrywood Street, Winter Haven

$164,900
2 Beds 2 Baths Eagle Pond Condo SubDv. 33884 Zip Code
Looking for a COUNTRY CLUB LIFESTYLE? Conveniently located in Cypresswood Golf & Country Club, on Dundee Rd near HWY 27. RECENT UPDATES INCLUDE a 2 year old AC unit, and in 2026 brand New hot water heater, countertops throughout, dishwasher, microwave, disposal and kitchen faucet. This SUPER CLEAN 2 bed/2 bath condominium offers an open concept with 10' Ceilings, Crown Molding, 2" Blinds and Ceiling Fans throughout. You will love the spacious kitchen with pantry & lots of counter space. Both bedrooms feature walk in closets. Ample amount of closet space plus an outside storage room & assigned parking. Cypresswood residents enjoy a resort and country club lifestyle! The 18 hole golf course and Clubhouse with chef prepared meals & live music are open to the public. Additional amenities include Brand New tennis & pickleball courts, plus a half Olympic size pool. Located just minutes from trendy downtown Winter Haven, convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, hospital and medical facilities. Just 5 minutes to BRAND NEW Publix and ALDI grocery's, 7-11 gas station & McDonalds.

508 Eagle Pond Drive Unit 508, Winter Haven

$200,000
2 Beds 2 Baths Vienna Square Ph 01 SubDv. 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square home. This one can be a real charmer with your personal touches. Bright, light, and open floor plan. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

2338 Salzburg Loop, Winter Haven

$324,900
4 Beds 2 Baths Gardens Ph 01 SubDv. 33880 Zip Code
Welcome to 418 Majestic Gardens Blvd, Winter Haven, FL 33880, a spacious and move-in-ready 4-bedroom, 2-bath home located within a gated community. Offering a well-designed floor plan with generous living and dining areas, this home provides plenty of space for everyday living, entertaining, or continued use as an investment property. The kitchen features abundant cabinetry, ample counter space and stainless-steel appliances, while the open living areas are enhanced by high ceilings and plenty of natural light. The spacious primary suite includes a large private bath with dual vanities, soaking tub, separate shower and walk-in closet space. Three additional bedrooms provide flexibility for family, guests, a home office or additional accommodations. Step outside to enjoy the screened rear lanai overlooking a fully fenced backyard with plenty of room to relax, garden or entertain. A large concrete pad provides additional outdoor-use possibilities, while approximately 20 producing sugar apple plants create a unique backyard feature for those who enjoy fresh tropical fruit and gardening. Adding to the property's versatility, the home has previously been utilized as an Airbnb/short-term rental and has provided income for the current seller, making it an attractive option for buyers searching for either a primary residence or potential investment property. Conveniently located near Winter Haven shopping, dining, recreation and major roadways, this property combines space, privacy and opportunity. Move-in ready with a flexible floor plan, gated-community setting, screened outdoor living area, fenced yard and established fruit-producing plants—418 Majestic Gardens Blvd is ready for its next owner.

418 Majestic Gardens Blvd, Winter Haven

$119,000
2 Beds 2 Baths Lakeridge Condo SubDv. 33881 Zip Code
Virtually Staged. Virtually staged bedroom. CENTRAL FLORIDA LAKE VIEW CONDO- THIS IS THE ONLY GATED 55+ CONDOMINIUM COMPLEX IN WINTER HAVEN. (Slightly younger buyer could possibly get approved.) NEW ENERGY-EFFICIENT WINDOWS IN THIS IMMACULATE, MOVE-IN READY 2 BEDROOM 2 BATH CONDO. WATER HEATER is 2025 & CENTRAL AIR CONDITIONER is a 2020. The kitchen is larger than most condo kitchens & the unit has a total of 1,347 sq. ft. of living area. MONTHLY FEE INCLUDES-WATER, SEWER, CABLE, FIBER OPTIC INTERNET, TRASH REMOVAL, CONDO RESERVES & use of recreational facilities- HEATED POOL, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. All appliances & washer/dryer are included. The 26'x14' great room adjoins the additional FL/bonus room with large storage closet. The 16X14 foot master bedroom easily accommodates a king-size bed & has a walk-in closet & en-suite bathroom with walk-in shower. The 2nd bedroom includes a space-saving drop-down Murphy bed. The 2nd bathroom has a tub/shower combination. The linen closet is near the washer & dryer for convenience. Lakeridge is close to shopping, places of worship, groceries, restaurants, medical offices & hospital. Extra assigned storage on the same floor. Social activities available, if you wish to participate. Lakeridge is well-maintained, well-managed & passed inspections & studies with flying colors. Electric car charger on site for owners use. YOU ONLY HAVE TO PAY FOR YOUR ELECTRICITY HERE, AS EVERYTHING ELSE IS INCLUDED IN THE MONTHLY FEE. ONE SMALL PET MAY BE APPROVED. NON SMOKING PROPERTY. Quick Closing is available. Information believed to be accurate but not guaranteed. Measurements are approximate.

1776 6th Street Nw Unit 409, Winter Haven

$239,900
3 Beds 2 Baths Winterset 03 A Condo Ph 01 SubDv. 33884 Zip Code
3 bedroom, 2 bath ground-floor end-unit condo home with gorgeous views of Lake Winterset and a private 1 car garage—the perfect combination in one of Winter Haven’s most desirable gated communities. Welcome to 701 Magnolia Place, a spacious lakeview residence designed for easy single-level living with approximately 1,180 square feet, durable luxury vinyl plank flooring, and a comfortable, open layout. The living room is anchored by a fireplace and flows naturally into the dining area, creating an inviting space for everyday living and entertaining. The kitchen features white cabinetry, soft close drawers, newer stainless steel appliances, generous counter space, and an adjoining breakfast nook. The primary suite is spacious, measuring approximately 11x16, with lake views, a private bath with walk-in shower, generous closet space and direct access to the back patio. Two additional bedrooms provide flexibility for guests, a home office, hobby room, or den—a combination that makes this 3-bedroom floor plan especially hard to find in Winterset. A second full bath with tub and shower combo completes the interior. Step outside to the private screened porch, where wide-open green space and beautiful Lake Winterset views create the perfect place to enjoy your morning coffee, unwind at the end of the day, and watch sunsets you truly have to see to believe. As an end unit, the home enjoys an added sense of openness and privacy, while the attached one-car garage provides valuable parking and storage. Beyond the residence, the community of Winterset delivers on the Florida lifestyle. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Ground-floor living, an end-unit location, three bedrooms, private garage, screened porch, Chain of Lakes access, resort-style amenities, and gorgeous Lake Winterset views—701 Magnolia Place offers a combination that is difficult to find.

701 Magnolia Place, Winter Haven

$275,000
3 Beds 2 Baths Gardens SubDv. 33880 Zip Code
Welcome home to this beautifully designed 3 bedroom , 2 bath split plan home located in a desirable gated community! The open layout creates a spacious, inviting feel, with a large kitchen overlooking the living areas - perfect for every day living and entertaining. Step outside to enjoy a large back yard, offering plenty of room for pets, play, gardening or creating your own outdoor oasis. Located in an area convenient to LEGOLAND, major highways shopping, restaraunts, and Central Florida's world-famous theme parks, this home puts everything you need within easy reach. Best of all, there is no CDD, No flood insurance required, and low HOA, making this an attractive opportunity for both homeowners and investors. A gated community, newer roof, paint and carpet, septic pumped in 2025, all makes this one worth seeing!

106 Majestic Gardens Court, Winter Haven

$365,000
3 Beds 2 Baths Hartridge Hills SubDv. 33881 Zip Code
Move In Ready Custom Home in a Gated Community Near the Airport. Community has a Private Dock and Boat Ramp with access to the Chain of Lakes. Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. New water heater and also passed 4-point inspection for insurance purposes. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Hartridge Hills Drive, Winter Haven

$114,995
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets & additional storage, creating the perfect space for showcasing your favorite pieces and hosting family & friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven

$164,800
2 Beds 2 Baths Lakeside Ranch For Mobile Homes SubDv. 33881 Zip Code
Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully maintained, offering peace of mind and comfort from day one! BONUS=2024 Evolution C4PRO golf cart is included! The sales price includes the $11,000 share of ownership in this Co-op Community. The low $145/mo HOA fee includes water, sewer, and lawn mowing. Individual mailbox, community laundry and clothesline available. No pets. No motorcycles. Trucks ok. Located near shopping, entertainment, and health care!

628 Lakeside Ranch Lane, Winter Haven

$229,900
2 Beds 2 Baths Winterset 01 A Condo 02 Amd SubDv. 33884 Zip Code
Virtually Staged. Completely renovated ground-floor condo with beautiful lake views of Lake Winterset on the world-famous Winter Haven Chain of Lakes! Welcome to Winterset, where this stunning remodeled 2 bedroom, 2 bath condo combines a spacious interior, private screened porch, exceptional water views, and the amenities of one of Winter Haven's most desirable gated communities. From top to bottom this unit is fresh, bright, and remarkably spacious. New flooring flows throughout, complemented by updated lighting, contemporary ceiling fans, modern fixtures, and a crisp neutral palette. The open living and dining areas provide plenty of room to relax and entertain, while large windows frame the expansive lawn and sparkling waters of Lake Winterset beyond. The expanded kitchen delivers the wow factor with elegant granite countertops, soft-close cabinetry with crown molding, black appliances including a gas range and dishwasher, a generous breakfast bar, and abundant cabinet and counter space. Open to the dining and living areas, it creates an easy flow throughout the main living space. The primary suite offers beautiful lake views, a huge walk-in closet and a luxurious master bath with double vanity undermount sinks, granite countertop, sleek chrome fixtures and a frameless glass walk-in shower surrounded by custom tile. Positioned separately from the primary suite, the spacious second bedroom offers two closets and convenient access to the beautifully renovated guest bath, complete with granite-topped vanity and custom-tiled tub and shower. The thoughtful layout also includes an interior laundry area and additional storage. Stepping outside to the private screened porch you'll find the perfect spot to unwind while watching the water and the most amazing sunsets you have to see to believe. Beyond the residence, Winterset delivers the Florida lifestyle buyers come here to enjoy. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Beautifully renovated, ground-floor living, an unusually spacious primary suite, private screened porch, resort-style amenities, Chain of Lakes access, and a gorgeous water view right outside your windows—this is the kind of Winter Haven condo that's easy to fall in love with.

503 Sweet Bay Circle, Winter Haven

$355,000
3 Beds 2 Baths Lake Ashton West Ph Ii South SubDv. 33884 Zip Code
1124 Sawgrass Drive Winter Haven, Fl. 33884 is located in Lake Ashton, an Exclusive Florida Retirement Community offering tailored activities and amenities to those seeking an Active 55 Plus lifestyle. Built in 2022 with 1,917 sq. ft. living area, this ST. MARKS floor plan home is MOVE IN READY and is located on the 10th Fairway of the West Golf Course in Lake Ashton. When you enter this home you have a direct view of the golf course thru the Triple Sliders that separate the LR from the Lanai. This Split Floor Plan offers: Formal and Casual Dining areas, a Living Room, Laundry Room, Primary Suite, 2 Bedrooms and a Flex Room with Built In Shelves. The living room is at the center of the this home with the Kitchen, Formal Dining, Primary Suite and Dinette areas flowing into the LR area. The Kitchen is spacious and offers a Breakfast Bar, SS Appliances, Recessed Lighting, Pull Out Drawers, Ample 42" Cabinetry and Granite Countertops. The Dinette area is easily accessible to the kitchen and Flex Room and Double Sliders provide direct access to the Covered and Screened Lanai. The Open and Spacious Floor Plan makes entertaining a BREEZE! The comfortable and spacious Primary Suite offers His/Her Walk in Closets, an attractive Primary Bath area with His/Her separate vanities, large soaking tub, walk in shower, separate water closet and linen closet. Glass Block accents the Primary Bath and provides an abundance of natural light into the room. Bedroom 2 and Bedroom 3 are separated by the Guest Bathroom with shower/tub combo and comfort height vanity. Each Bedroom has a built in Closet. The laundry room (washer/dryer included in the sale of the home) is sizable and is the passage from the garage to the kitchen. The garage has a separate golf cart entry and the golf cart is included with the sale of the home. Grab a great book and a cup of coffee and relax on the screened and covered lanai. Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

1124 Sawgrass Drive, Winter Haven

$749,000
3 Beds 4 Baths Cypresswood Palma Ceia SubDv. 33884 Zip Code
Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven

$165,000
2 Beds 2 Baths Eagle Pond Condo SubDv. 33884 Zip Code
Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with 10' high ceilings, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

1105 Eagle Pond Drive Unit 1105, Winter Haven

$115,000
2 Beds 2 Baths Orange Manor West Coop Inc SubDv. 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven

$165,000
2 Beds 2 Baths Cypresswood Tennis Villas SubDv. 33884 Zip Code
Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven

$110,000
2 Beds 2 Baths Oakwood Estates SubDv. 33880 Zip Code
Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven

$309,900
3 Beds 2 Baths Traditions Ph 01 SubDv. 33884 Zip Code
Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven

$399,900
4 Beds 3 Baths Traditions Ph 02 SubDv. 33884 Zip Code
Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the highly desirable Traditions at Ruby Lake, a premier 55+ gated community offering the very best of Florida resort-style living. Situated on an oversized lot, this exceptional home features a desirable split floor plan Jack and Jill bathroom w/ walk-in tub and soaring high ceilings that create a bright, open, and spacious feel throughout. Thoughtfully upgraded for both comfort and efficiency, the home offers a spacious, expanded screened lanai with brick pavers—the perfect outdoor retreat for entertaining or enjoying a quiet evening—enhanced by customizable LED lighting to create the ideal ambiance. Energy-saving features include foam-core insulation in the concrete block walls, new Andersen windows, and a freshly painted exterior. Inside, you'll find hardwood flooring in the primary bedroom and front bedroom, which also makes an ideal home office. The kitchen is beautifully appointed with custom cabinetry, granite countertops, slate stainless steel appliances, and abundant storage. Custom maple shelving in the pantry, laundry room, and both linen closets adds both elegance and functionality. The primary bath also features granite countertops, completing the home's high-quality finishes. Designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces that provide both privacy and flexibility for family and guests. HOA dues provide exceptional value and include weekly lawn and landscape maintenance, Spectrum TV service, and exterior house painting every seven years. Residents also enjoy full access to the community's impressive lakefront clubhouse, featuring a resort-style pool and spa, sauna, showers, a fully equipped fitness center, staffed front desk, library, business center, billiards room, craft room, and a spacious ballroom that hosts meetings, dances, entertainment, guest speakers, clubs, and social events. Outdoor amenities are equally impressive and include tennis, basketball, bocce ball, shuffleboard, pickleball, three community boat docks, a picturesque lakeside gazebo, and a paved walking path along the lake—perfect for morning strolls or evening exercise. If you're looking for a move-in-ready home with exceptional upgrades, low-maintenance living, and an active, resort-style lifestyle, this is the one you won't want to miss!

4132 Martindale Loop, Winter Haven

$469,000
3 Beds 2 Baths Village/Spirit Lake Ph 01 SubDv. 33880 Zip Code
Homes in The Village at Spirit Lake don’t come up for sale very often, and this one has a lot to offer. 315 Lanceolate Drive is a 3-bedroom, 2-bath pool home with two additional air-conditioned rooms in the converted garage, giving you plenty of flexibility for additional bedrooms, home offices, a gym, playroom, or extra storage. Inside, the home has been thoughtfully updated with a completely renovated kitchen, remodeled bathrooms, and comfortable living spaces that feel fresh and move-in ready. The second bathroom offers direct access to the pool area, making it especially convenient for everyday Florida living. Out back, you’ll find a screened lanai overlooking the saltwater pool and a fully fenced backyard with plenty of room to relax, entertain, or enjoy the sunshine. If you have a boat, this home makes that easy too. The extended driveway provides room for boat parking, and residents have access to the community’s private boat ramp on Spirit Lake. The gated Village at Spirit Lake also offers a clubhouse, new playground, pickleball courts, and basketball court, all with a reasonable HOA. Located in unincorporated Polk County with county taxes only, the home is just minutes from the Polk Parkway with convenient access to Winter Haven, Lakeland, shopping, dining, schools, and LEGOLAND Florida Resort. Saltwater pool, room for the boat, access to the lake, and a home that’s already been beautifully updated. There’s a reason homes in this neighborhood don’t change hands very often.

315 Lanceolate Drive, Winter Haven

$162,000
2 Beds 2 Baths Lakeridge Condo SubDv. 33881 Zip Code
NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room with views of Spring Lake & is located in the beautiful City of Winter Haven. Lakeridge Condominiums offers a maintenance free lifestyle with heated pool, tennis, shuffleboard, community room, gated secured entrances and covered assigned parking space. Water, sewer, cable, internet, trash removal and use of recreational facilities are included in the monthly fee. This well appointed move in ready condo has a large bright kitchen with lots of cabinets, great counter space, appliances and pantry closet. The kitchen overlooks the great room that also adjoins the additional bonus area and storage closet. The primary bedroom has a walk in closet & bathroom with a walk in shower. Beautiful views of Spring Lake can be enjoyed from the Primary bedroom & living areas. Washer/Dryer are included. Convenient to shopping, groceries & restaurants. Extra assigned storage bin on same floor. Lakeridge Condominiums is an age restricted, well maintained & well managed community.

1776 6th Street Nw Unit 807, Winter Haven