Winter Haven Homes with Restaurant Community Features

Winter Haven Homes with Restaurant Community Features

Welcome to Winter Haven, Florida – a vibrant city nestled in the heart of Polk County, renowned for its stunning lakes, rich history, and a welcoming community spirit. With its picturesque landscapes and warm climate, Winter Haven is an ideal destination for those seeking a perfect blend of relaxation and recreation. Known as the "Chain of Lakes City," it boasts over 50 lakes, offering endless opportunities for boating, fishing, and enjoying the great outdoors.

One of Winter Haven's standout features is its thriving restaurant community. The city is home to a diverse array of dining options, from charming cafes to upscale restaurants, making it a food lover's paradise. Whether you crave fresh seafood, hearty Italian, or delightful local cuisine, you’ll find it all just a stone's throw away from your front door. The culinary scene here is not just about food; it’s about building connections and creating memorable experiences with friends and family.

When it comes to real estate, Winter Haven offers homes that embrace this community-centric lifestyle. Many properties are strategically located near popular dining spots, allowing residents to indulge in the vibrant local culture without venturing far from home. Imagine enjoying a leisurely evening stroll to your favorite restaurant or hosting friends for a weekend barbecue in your spacious backyard, all while being surrounded by the charm of this beautiful city.

With its appealing blend of natural beauty, a bustling restaurant scene, and a strong sense of community, Winter Haven is not just a place to live; it’s a place to thrive. Discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Winter Haven Homes with Restaurant Community Features

2991 Plantation Road, Winter Haven
$465,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood Plantations SubDv. ⋅ 33884 Zip Code
Move in Ready in Cypresswood Plantations!! Located in the highly sought-after gated golf community of Cypresswood in Winter Haven. This beautiful custom built home features 4 bedrooms, 3 baths situated on a large, one-third acre lot and boasts 2,625 square feet of living area and offers the versatility of a triple-split floor plan. Fully equipped updated kitchen with granite countertops, island and maple wood cabinetry. The spacious floor plan includes a formal living and formal dining, family room with wood burning fireplace. Primary suite with crown molding and large primary bath, huge tiled shower, dual sinks, and granite countertops. Screened in lanai and whole house generator. Large two car side load garage. Enjoy the quiet, beautiful and peaceful views Cypresswood has to offer, along with a 24-hour manned gated entrance, golf community that features golf, tennis, fitness, community and clubhouse with restaurant and activities. Close to all Florida major attactions, shopping and medical facilities.

2991 Plantation Road, Winter Haven
260 Greenfield Road, Winter Haven
$349,900
3 Beds ⋅ 2 Baths ⋅ Cypresswood Greenfield Village SubDv. ⋅ 33884 Zip Code
Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed private POOL deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is 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 for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours.

260 Greenfield Road, Winter Haven
306 Eagle Pond Drive Unit 306, Winter Haven
$211,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
MOTIVATED SELLER! Enjoy the best of Florida living in this beautifully updated condo located in the desirable, gated community of Cypresswood Golf & Country Club in Winter Haven! Featuring stylish upgrades, peaceful pond views, and an array of resort-style amenities, this inviting home offers the perfect blend of comfort, convenience, and an active lifestyle. Step inside to discover tile flooring throughout, elegant marble kitchen countertops, an extended breakfast island perfect for casual dining and entertaining, and matching marble countertops in both bathrooms. Additional upgrades include ceiling fans, a newer water heater, and the convenience of an interior laundry area with washer & dryer included. The floor plan features two spacious bedrooms, each with its own walk-in closet. The primary suite offers a private en-suite bathroom, while additional linen storage and a separate exterior storage closet with shelving provide plenty of room to stay organized. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic sized community pool, lighted tennis/pickleball courts, clubhouse with a restaurant, event space and more. Minutes from Hwy 27 and the I-4 corridor. Centrally located between Orlando and Tampa. Schedule your private showing today!

306 Eagle Pond Drive Unit 306, Winter Haven
5288 Green Drive, Winter Haven
$314,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this spacious Biscayne floor plan in Lake Ashton, a gated 55+ GOLF community in Winter Haven in Central Florida! This solar-powered home offers over 1,800 sq. ft. of living space with 3 bedrooms, 2 baths, a 2-car garage, and an expanded outdoor living area. One bedroom is ideal as an office or den. The open-concept floor plan features living, dining, dinette and kitchen areas, with triple sliders and double sliders opening to a covered, screened lanai with privacy panels, newer ceiling fans and lighting, and tile flooring. The kitchen boasts granite countertops, upgraded appliances, tile backsplash, newer sink and select lower-cabinet pullouts. The private primary suite includes two walk-in closets, dual vanities, soaking tub, step-in shower with grab bar and linen closet. Additional features include luxury vinyl plank flooring, 2022 roof and water heater, 2022 solar panels and gutters, automatic garage screen, hurricane shutters, and a beautifully landscaped paver outdoor area. The washer and dryer, garage refrigerator and generator convey. Enjoy amenity rich living in the highly desirable Lake Ashton community!

5288 Green Drive, Winter Haven
575 Saint Andrews Road, Winter Haven
$286,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Golf Course Living with Total Peace of Mind! Welcome to your worry-free oasis on the green. Nestled within this beautiful, gated community of Cypresswood Golf and Country Club, this beautifully maintained 2-bedroom, 2-bathroom golf-front home offers the perfect blend of active resort living and quiet tranquility. Imagine waking up, stepping onto your private patio, and sipping your morning coffee while looking out over pristine, rolling fairway. What truly sets this home apart is that every major expense has already been taken care of for you. You can move in with absolute confidence, knowing you won't have to worry about costly upgrades or repairs for years to come. Recent premium updates include: •Brand New HVAC System (2024): Brand new inside and out for peak energy efficiency. •New Roof & Structural Updates (2022): Completely replaced roof, overhang, and facia boards. •Total Peace of Mind (2021): The entire home was fully re-plumbed. •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage door opener, a new garbage disposal, and upgraded GFCI outlets. Storage is never an issue with the massive 23x23 oversized garage—offering ample space for your vehicles, workshop, and of course, your golf cart. Opportunities in Cypresswood like this do not last long. Don’t wait to start living your dream golf-course lifestyle—call today to schedule your private showing!

575 Saint Andrews Road, Winter Haven
5344 Nicklaus Drive, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
Home for Sale in Lake Ashton, a Florida Retirement Community with Two (2) Golf Courses, Resort Style Amenities and Planned Activities like Trivia, Bingo, Dances, Day Trips, Holiday Events and MORE! This 3 Bedroom and 2 Bath home with over 1,600 sq. ft. living area would be a great seasonal home. The furniture in this home is negotiable. The exterior of this home has paver drive and walk ways, mature and well maintained landscape with rock-scape and landscape edging, a screened entry at the Front Door, and a Covered Lanai, on the front of the home, which is large enough for chairs. An irrigation system provides water to the large and beautiful Palm tree and other mature landscape around the home. This seasonally occupied and well maintained home offers an Open and Spacious Split Floor Plan with NO CARPET ANYWHERE! The kitchen features SS appliances (oven-December 2022, refrigerator 2021), Corian countertops, Dinette area with Bay Windows, Step Up breakfast bar and closet pantry. New Anderson Windows have been installed in the Dining room, Primary Bedroom and Primary Bathroom. Laminate flooring is in each of the bedrooms. The Primary Suite has 2 large walk-in closets, His/Her comfort height vanities, a Water closet and Large walk-in shower. The washer/dryer in the laundry room will be included in the sale of this home. The outdoor living area offers a 26 x 10 rear screened lanai and large paver area that is great for grilling. The 2 car garage is equipped with a "Skeeter Beater" for privacy and enjoying the cool cross breeze! Lake Ashton that offers 2 clubhouses, indoor and outdoor heated pools, pickle ball, tennis courts, racquetball, basketball, fitness centers, movie theaters, craft room, media center, several private lakes, private boat ramp/slips and more!! Come and enjoy your retirement and carefree living in the beautiful gated and guarded community of Lake Ashton today!

5344 Nicklaus Drive, Winter Haven
1321 Oakmont Drive, Winter Haven
$424,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
** CDD Debt Balance PAID IN FULL, saving you thousands! **A new four-season Sunroom was completed in April 2026. It is glass-enclosed with a separate HVAC mini-split and has beautiful new flooring. This home offers amazing curb appeal, with new landscaping on every side of the house, including lush privacy plantings in the back. The St. Marks floor plan has 3 Bedrooms and 2 Baths, plus a Den, spacious Laundry Room and a Double-car Garage with designated Golf Cart Entry. With 2,069 sq.ft. living area in the original house PLUS an additional 243 sq.ft. living area in the Sunroom, this OPEN and SPACIOUS home is ideal for entertaining friends and family. The tile plank flooring that appears "wood like" flows thru the LR, Formal Dining, Foyer, Kitchen, Dinette, Den, Sunroom and Laundry Rooms -- adding a touch of class to this truly charming home! The voluminous ceilings are enhanced with the 8ft. door openings in the home. The kitchen is enhanced with Granite countertops, soft close drawers and cabinets with newer hardware, stainless steel appliances, tiled backsplash, step-up breakfast bar with pendant lights, and abundant countertop space for food prep and display. The Dinette area, which is adjacent to the kitchen, is accessible from the Sunroom and the Den. The spacious Owners Suite occupies the left wing of the home and is a private retreat featuring His/Her walk-in closets and its very own En-Suite bath area. The Primary Bath offers His/Her comfort height vanities with Granite countertop and Newer Cabinet Hardware, a Walk-in shower w/glass door enclosure and Large soaking tub. The triple glass block allows an abundance of natural light into the space. A "Barn-Like" door on a smooth track system separates the Primary Suite from the Primary Bath. It's stylish and practical. On the right side of this Split Floor Plan home are Bedrooms 2 and 3 and the Guest Bath. The Guest Bath has a comfort height vanity, Shower/tub combo and Newer Hardware on the Cabs. It's perfectly positioned between the Guest Bedrooms. The laundry room is well designed and is the passage from the garage into the home. The laundry room has additional shelving for your storage needs. Hosting a Game Night or Want to Cozy Up with a Good Book? The brand-new SUNROOM would be the ideal place! It's accessible thru the TRIPLE SLIDERS in the LR & DOUBLE SLIDERS in the Dinette. ADDITIONAL UPGRADES: Whole House Gutter System, Automatic Screen (Skeeter Beeter) on the Garage Door, Storm Door on the front door, Pull Down Attic Ladder, new window dressings throughout the home, Six-Filter Reverse Osmosis Water System added to the Kitchen sink, Updated Painting in Several Rooms and Cabinet Handles in the Kitchen and Bathrooms. Lake Ashton has (2) clubhouses, (2) Golf Courses, Planned Activities and Resort Style Amenities. Residents enjoy 2 Swimming Pools (one Indoor & one Outdoor), Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Rooms, Media Rooms, Indoor Racquetball, Indoor 1/2 Court Basketball, Pickle Ball Courts, Tennis Courts, Shuffleboard Courts, Eagles Nest (an Eatery), a Pro Shop and MORE! Lake Ashton is a beautiful 55 Plus Community in Florida closely located to Shopping, Restaurants, Entertainment and Medical Facilities. MAKE AN APPOINTMENT TODAY TOUR THIS BEAUTIFUL HOME.

1321 Oakmont Drive, Winter Haven
2801 Wingfoot Court, Winter Haven
$245,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villa 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 trimwork 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. Both bathrooms also feature skylights. 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, pickleball 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
5325 Snead Drive, Winter Haven
$349,500
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
MOTIVATED SELLERS!!! Welcome to one of THE MOST DESIRABLE AND BEAUTIFUL 55+ GATED/GUARD community in Winter Haven, FL! LAKE ASHTON has great amenities for their residents to enjoy every day and feel in PARADISE. An enormous club house were events are held, two pools, dog park, golf course, bowling, movie theater, fitness center, restaurant, and more. There's also a 2nd clubhouse available for residents. This gorgeous well maintained home has MULTIPLE VALUABLE UPGRADES that the future owner would enjoy. Even the floor plan was updated in the KITCHEN making this home UNIQUE in the neighborhood! NEW ROOF was installed in 2024, DISHWASHER FEB 2026, REFRIGETATOR NOV 2025, and WATER HEATER 2021. Also ENJOY the BENEFIT of having WATER SOFTENER, A WATER PURIFIER SYSTEM IN THE KITCHEN and QUARTS COUNTER TOPS. For the outdoor living you have a SPACIOUS TILE FLOORING, SCREENED LANAI WITH FLORIDA GLASS FOR PRIVACY. ONE OF THE BEST FEATURES OF THIS PROPERTY IS THAT IT HAS PAID OFF SOLAR PANELS. WHAT ELSE YOU CAN ASK FOR? This helps with the electric bill cost. COME AND SEE THIS AMAZING HOME THAT WILL MAKE YOU FEEL IN PARADISE!

5325 Snead Drive, Winter Haven
508 Eagle Pond Drive Unit 508, Winter Haven
$159,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Great Price! A Pristine 2 bed/2 bath condominium, Conveniently located in Cypresswood Golf & Country Club, on Dundee Rd near HWY 27. 2026 UPDATES - BRAND NEW hot water heater, countertops throughout, dishwasher, microwave, disposal, kitchen faucet. 2 year old energy efficient AC. Featuring 9' 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! There's an 18 hole championship golf course with a Clubhouse that offers chef prepared meals & live music. Also open to the public. Additional owner amenities include Brand New tennis & pickleball courts, and 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
4040 Palma Ceia Circle, 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
665 Broadmoor Circle, 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
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