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$149,700
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villas SubDv. ⋅ 33884 Zip Code
UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS.

649 Broadmoor Circle, Winter Haven
$85,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit on the front porch and enjoy your morning coffee. The rooms are nice sized with great closet space. The laundry/shop area has plenty of space for your Do-it-yourself projects. Oakwood Estates, a 55+ community offers 2 pools, 2 clubhouses, shuffleboard, tennis courts, miniature golf, and much more. In addition to the amenities, Oakwood offers many opportunities to meet with new folks. Come to Koffee Klatch on Wednesday morning, enjoy an ice cream social a couple times a month, or get your Boogie on at one of the dances. Call today to view this home that's just waiting for YOU!!

4127 Sprucewood Street, Winter Haven
$259,000
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and relaxing 2 bedroom 2 bath with 2 car garage. The beautifully finished kitchen comes complete with a full stainless steel appliance package, granite tops, and modern gray cabinets. These lovely cabinets, and countertops also complement both the primary bath, and the guest bathroom. Neutral colors offer a nice finish to this well designed floor plan. Enjoy the privacy from your screened patio with no back door neighbors. Easy living awaits without the big worries. Exterior paint, roof replacement, irrigation water, yard maintenance, and Spectrum Internet/TV package is included in the reasonable monthly fees. Enjoy the social activities with the neighbors, splash in the community pool, or make a hit on the tennis/pickleball courts. The convenient location, and reasonable monthly fees makes this 55+ community an easy choice. Step inside, fall in love. Make it yours!

1709 Linz Ct, Winter Haven
$187,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.

1012 Medinah Dr Se, Winter Haven
$230,000
2 Beds ⋅ 3 Baths ⋅ Casarena On The Lake SubDv. ⋅ 33881 Zip Code
Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached two-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

11 Casarena Court, Winter Haven
$263,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
NEW PRICE IMPROVEMENT! WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

3923 Baldwin Lane, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villas Gc-2 SubDv. ⋅ 33884 Zip Code
Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.

2817 Wingfoot Court, Winter Haven
$229,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood Enclave Ph 01 SubDv. ⋅ 33884 Zip Code
This meticulously maintained and professionally updated 2 bedroom 2 bath villa is 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. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and brand new tennis and pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

14 Enclave Drive, Winter Haven
$105,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroom, 2-bathroom manufactured home comes fully furnished and is being sold as-is, allowing you to move in comfortably without additional expenses. The double panes windows add thermal efficiency, and the 2014 shingle roof is in great condition . Features Include: - Two spacious bedrooms (split bedroom ) and bathrooms - Two attached screened-in porches, perfect for enjoying the Florida sunshine - Utility shed for additional storage (houses washer/dryer) - Parking space for two vehicles - Access to community amenities, including swimming, shuffleboard, fishing pier, and tennis Location: Conveniently located close to shopping centers and restaurants, everything you need is just a short drive away. Enjoy a vibrant community lifestyle with various social activities and events right at your doorstep. This section is a “No Dog” area but other inside pets are acceptable (cat, bird, fish)

4246 Cedarwood Street, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Valhalla SubDv. ⋅ 33884 Zip Code
Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches. The open concept kitchen includes granite countertops, custom cabinetry, a center island with breakfast bar, Bosch dishwasher, stainless oven and range, walk-in pantry, and a passthrough to the living area for open flow. Wood plank flooring runs throughout the main spaces. The living room features large windows and an adjacent flex space for dining, office, or den use. The primary suite includes an ensuite bathroom with slate tile, jacuzzi tub, glass shower, dual sinks, and the laundry room is part of the primary. The guest room features a window seat and recessed lighting. A third room functions well as an office or additional guest space. HOA covers lawn care, water, trash, basic cable, pool, and tennis access.

104 Woden Way, Winter Haven
$198,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one, call to view today. Flood zone area is deemed to be correct but must be verified by buyer/buyer broker.

683 Broadmoor Circle Unit 683, Winter Haven
$259,000
2 Beds ⋅ 2 Baths ⋅ Vienna Square Phase 3a SubDv. ⋅ 33884 Zip Code
NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver driveway, granite counter tops, shaker cabinets, new Whirlpool appliances, Delta fixtures, designer lighting, inside laundry and more. In the owners retreat, there is a walk-in closet and tiled walk-in shower. The guest bathroom has a tub/shower combo. Lawn maintenance and most exterior maintenance are included in the monthly HOA dues, along with Spectrum basic cable/internet, access to the clubhouse, heated pool, fitness center, and more. This new home comes with a structural warranty. Call today!

1703 Linz Court, Winter Haven
$139,000
2 Beds ⋅ 2 Baths ⋅ Royal Crescent Condo SubDv. ⋅ 33884 Zip Code
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.

5850 Cypress Gardens Boulevard Unit 304, Winter Haven
$229,500
2 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 2a SubDv. ⋅ 33884 Zip Code
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.

1561 Vienna Square Drive, Winter Haven
$108,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the living room give the feel of lots of space. The floorplan offers 2 living areas. The guest bedroom has the main bathroom attached which is perfect for those overnight guests. The primary bedroom is spacious with two separate closets for him and her with a nice sized shower stall in the primary bathroom. The shingle roof was installed in 2021. The vapor barrier was replaced in 2023 and the home has new skirting. The side porch offers more living space and is backed with a great workshop area. The laundry is inside the home. If all that isn't enough there is an EV charging port installed. This home is located in Oakwood Estates, a 55+ community offering many activities or just sit back and enjoy the peaceful community. Make your appointment today!! This home will be sold unfurnished with appliances only.

4321 Cherrywood Street, Winter Haven
$21,000
Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome to your future home site in a vibrant 55+ community, perfectly positioned along the tranquil canal connecting Lake Hamilton to Lake Henry, with breathtaking views of Lake Henry itself. This is an ideal location for boating and fishing enthusiasts, offering exclusive access to the waterway. The community boasts a wide array of activities and amenities, including a refreshing pool, well-maintained shuffleboard courts, convenient coin laundry facilities, and secure RV/boat storage (available for an additional fee). Enjoy the peace of mind that comes with living in a gated community where safety and security are top priorities. Please note that the property includes a 99-year land lease.

7066 Fairview Village Circle, Winter Haven