Winter Haven Homes with Tennis Court(s) Community Features

Winter Haven Homes with Tennis Court(s) Community Features

Welcome to Winter Haven, Florida—a vibrant city nestled in the heart of Polk County, where the sun shines bright and the community spirit thrives! Known for its picturesque lakes and lush landscapes, Winter Haven is a haven for outdoor enthusiasts and families alike. With its charming downtown area filled with unique shops, delightful eateries, and a rich history, there's something for everyone in this welcoming city.

One of the standout features of Winter Haven is its diverse range of residential communities, particularly those that boast homes with tennis courts. Imagine waking up each day in a beautiful home, surrounded by manicured lawns and the sounds of nature, with the convenience of a private tennis court right in your backyard. These properties not only offer a perfect setting for active lifestyles but also foster a sense of community among neighbors who share a passion for the sport.

Living in a home with a tennis court in Winter Haven means you can enjoy year-round access to your favorite game, whether you’re challenging friends, hosting family gatherings, or simply enjoying a peaceful afternoon practice. The community features often include beautifully landscaped common areas, walking trails, and recreational facilities that enhance the quality of life for residents.

With its ideal location, Winter Haven is also just a short drive from the attractions of both Orlando and Tampa, making it a perfect blend of tranquility and accessibility. Whether you’re looking to invest in a family home or a vacation retreat, Winter Haven’s homes with tennis courts offer an exceptional lifestyle in a city that truly feels like home. Come discover your dream home in this enchanting Florida city!

Newest Winter Haven Homes with Tennis Court(s) Community Features

$309,900
3 Beds ⋅ 3 Baths ⋅ Casarena On Lakes SubDv. ⋅ 33881 Zip Code
Welcome to 2 Casarena Ct, a truly unique opportunity in a private gated Winter Haven community. One of only three 3-bedroom with 3 full bathroom residences in the community, this spacious home is ideally positioned to capture beautiful views of Lake Cannon, part of Winter Haven’s renowned Chain of Lakes. Step inside to an inviting open-concept floor plan featuring an expansive living and dining area highlighted by a striking fireplace, creating a warm focal point for both everyday living and entertaining. The thoughtfully designed layout includes two generous primary suites, providing exceptional privacy and flexibility for owners, guests, extended family, or seasonal visitors. Each primary offers spacious living accommodations, with the balcony primary offering double vanity and a sauna in the shower, the while the additional ensuite bedroom and bath provide even more versatility. The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry, and convenient access to the main living and dining spaces. Enjoy Florida living from multiple outdoor areas, including a private balcony overlooking the community pool with views toward Lake Cannon, as well as a private Florida room at the rear of the home—perfect for morning coffee, reading, relaxing, or enjoying the Florida sunshine year-round. Additional features include two HVAC systems, with one replaced approximately six months ago, tankless water heater, natural gas connection, a whole-home generator for added peace of mind, and a two-car garage. A unique private paver parking space provides additional dedicated parking beyond the garage—an exceptional feature for condo living. Residents enjoy the benefits of a private gated community along with lawn care, access to the community pool, and lake access to Lake Cannon and the Chain of Lakes with boat slips that are first come first serve. The combination of water views, spacious living areas, multiple private suites, outdoor living spaces, garage parking, and community amenities makes this property an excellent option for buyers seeking the convenience of low-maintenance living without sacrificing space, privacy, or comfort. Whether you're looking for a full-time residence, seasonal Florida retreat, or spacious lock-and-leave lifestyle, 2 Casarena Ct offers a rare combination of privacy, lakefront community living, and exceptional interior space in the heart of Winter Haven.

2 Casarena Court, Winter Haven

$349,001
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

4075 Bedford Avenue, Winter Haven

$235,000
2 Beds ⋅ 2 Baths ⋅ Winterset 03 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Waterfront Living • Renovated Interior • Private Garage. Imagine ending your day with a beautiful Florida sunset over Lake Winterset. This beautifully renovated 2-bedroom, 2-bath condominium offers something that is hard to find in condo living—a private 1-car garage, expansive waterfront views, and the added character of a second-floor residence with vaulted ceilings and skylights. Located in the gated Winterset community, this home combines a relaxed lakefront lifestyle with a thoughtfully updated interior that is comfortable, stylish, and move-in ready. The kitchen is truly the centerpiece, featuring abundant cabinetry, granite countertops, stainless-steel appliances, a stylish tile backsplash, and an oversized counter with generous breakfast-bar seating. The open design creates a spacious connection between the kitchen and living area. The main living area features rich wood flooring and a striking built-in entertainment center with display shelving and architectural detail. Step through the sliding glass doors and enjoy the true highlight of this home—the enclosed waterfront lanai overlooking Lake Winterset. With room for both dining and comfortable seating, this becomes an extension of the living space and an ideal place to enjoy the beauty of Florida's nature. Imagine starting your morning with coffee overlooking the lake or relaxing at the end of the day as the sun sets across the water. The views aren't simply outside your door—they become part of everyday life. Renovated throughout, this home offers a cohesive blend of comfort and style. Plantation shutters, updated bathrooms, wood flooring, and carefully selected finishes create a polished feel throughout. The primary bedroom offers beautiful lake views, while the second bedroom provides flexibility for guests, an office, or additional living space. A unique feature of this residence is the installed stair chair, providing added convenience between the garage level and the second-floor home. A 1-car garage is an especially desirable feature for condo living, providing secure parking and valuable additional storage. Having your own garage adds a level of convenience that is not commonly found with condominium living. Set within the gated Winterset community, this home offers a welcoming waterfront lifestyle surrounded by beautiful lakes, mature landscaping, and green spaces. Residents can enjoy the waterfront clubhouse, pool and spa, along with an active and social community atmosphere. Winterset provides opportunities for boating, fishing, and enjoying the peaceful waterfront setting, while remaining conveniently close to shopping, dining, entertainment, theme parks, airports, and Florida's east and west coast beaches. Whether you're looking for a full-time residence, seasonal retreat, or an easy-to-maintain Florida getaway, 809 Magnolia Place offers the rare combination of lakefront views, thoughtful renovations, vaulted ceilings, a private garage, and a lifestyle centered around the water.

809 Magnolia Place, Winter Haven

$350,000
3 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with a den, ideally situated in the premier gated active-adult community of Traditions at Lake Ruby. Designed with comfort, efficiency, and entertaining in mind, this beautifully appointed home offers an impressive array of upgrades and thoughtful features. The desirable split-bedroom floor plan provides privacy and versatility, including a spacious Junior Bedroom Suite with its own ensuite bath—perfect for visiting family or guests. The well-equipped kitchen is a chef’s delight, featuring a center island with pendant lighting, fingerprint-resistant stainless-steel appliance package, recessed lighting, and 42-inch white upper cabinetry enhanced with crown molding, soft-close hinges, and brush nickel hardware. A generous walk-in pantry provides additional storage, while the pull-out cabinet organizers keep everyday items conveniently within reach. The spacious Living Room features wood laminate flooring and triple glass sliding doors that open to the extended lanai, seamlessly blending indoor and outdoor living. The open-concept design also incorporates a dedicated Dining Room and cheerful breakfast nook, providing plenty of space for family gatherings and entertaining. The generously sized Primary Bedroom Suite is enhanced with laminate flooring and dual walk-in closets featuring deluxe closet organizer systems. The luxurious Primary Bath offers a handicapped-accessible tiled shower with glass enclosure, comfort-height vanity with dual sinks, and linen closet for additional storage. Outdoor entertaining is effortless in the oversized screened lanai, featuring decorative stamped-concrete flooring, retractable solar screens and a built-in buffet and BBQ Grill—perfect for enjoying Florida’s year-round outdoor lifestyle. Additional amenities include a versatile Den/Office, Laundry Room with cabinetry, washer and dryer, ceiling fans with remote controls, and extensive storage throughout. Energy-efficient features include solar panels with a monthly solar expense of approximately $209, a 15-SEER HVAC system, AO Smith hybrid water heater, Low-E windows, radiant heat barrier, and architectural shingle roof installed in 2026. A stone facade, decorative stone curbing, and paved driveway add to the home’s impressive curb appeal. Additional upgrades include smart-lock entry, whole-house generator, retractable garage screen, keyless garage entry pad, and a two-car garage equipped with three overhead storage racks, workbench with matching cabinetry, and an overhead solar skylight. Traditions at Lake Ruby offers an exceptional active-adult lifestyle with an impressive selection of amenities and planned community activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. Conveniently located near shopping, medical facilities, and major transportation routes, Traditions at Lake Ruby offers the perfect combination of resort-style amenities, energy-efficient living, and everyday convenience. HOME CAN BE PURCHASED FURNISHED

3541 Raleigh Drive, Winter Haven

$549,999
3 Beds ⋅ 3 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code
Virtually Staged. *GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the water 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 water views from this coveted lot location are spectacular! 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

$115,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Oakwood Estates 55+ Community | Fully Furnished Home with Over $19K in Upgrades | Winter Haven, FL Over $19,000 in recent major upgrades means the big-ticket items are completely done! This move-in ready, fully furnished 2-bedroom home in Winter Haven, Florida is located in the highly desirable Oakwood Estates resident-owned 55+ gated community. INTERIOR & MODERN UPGRADES Step inside to a bright, open floor plan filled with natural light from double-pane energy-efficient windows. Luxury vinyl plank (LVP) flooring flows throughout the home for durable, low-maintenance living. The upgraded kitchen includes stainless steel appliances, white cabinetry, wood-look countertops, and an updated sink. A charming built-in dining buffet adds extra storage and leads directly into the spacious living room. Both bedrooms are generously sized, featuring a primary suite with a walk-in closet. The indoor laundry room comes complete with a washer and dryer included. ADDITIONAL LIVING SPACE & EXTERIOR FEATURES Expand your living area into the private Florida room and fully enclosed lanai, ideal for year-round relaxation and entertaining. Major exterior and mechanical updates include a new roof installed in 2023, along with a new central HVAC system, electric water heater, rain gutters, and exterior porch tile all completed in 2024. Additional peace-of-mind features include hurricane shutters, low-maintenance vinyl siding, and an updated electrical panel. RESORT-STYLE 55+ COMMUNITY AMENITIES Oakwood Estates offers low-maintenance retirement living with exceptional amenities. Enjoy two heated community pools, two clubhouses, pickleball and tennis courts, shuffleboard, bocce ball, miniature golf, a private fishing lake with pier, secure RV and boat storage, a library, and an active social calendar with community events. SCHEDULE YOUR SHOWING With major mechanical systems replaced, high-end furnishings included, and a prime position in a top-rated Polk County 55+ community, this home offers incredible value. Take the virtual tour, view the photos, and contact us today to schedule your private tour.

4332 Cherrywood Street, Winter Haven

$144,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**LARGE 2 BEDROOM - 2 BATH CONDO - NEW LISTING IN CENTRAL FLORIDA**- AGE 55+, GATED COMMUNITY (however, a slightly younger age may be approved). This up-to-date condo provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Florida. NEW ENERGY-EFFICIENT WINDOWS THROUGHOUT. The monthly fee INCLUDES: water, sewer, trash, fiber optic cable package with Choice HD, digital video recorder & fiber optic internet w/ 1 gig speed, & use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated secured entrances, covered assigned parking space, social events & activities. This well-appointed, move-in-ready condo has a large, bright kitchen w/ lots of cabinets, a tile backsplash, flush-mount LED ceiling lighting, plenty of counter space, all appliances & a pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional FL/bonus area & storage closet. The 16' x 14 ' primary bedroom easily accommodates a king-size bed & has a walk-in closet with a decorative barn door. The beautiful remodeled primary bathroom has an extra-wide door for easy direct access & includes a walk-in shower with a large format designer wall tile, & a comfort-height vanity with a vessel sink. The 2nd bedroom is convenient to the hall bath, which has a tub/shower combination & comfort-height vanity. The WASHER & DRYER are included in the sale. The Flooring throughout is either wood-look luxury vinyl or tile, NO CARPETING. Custom window shades are in place and are included in the sale. An extra assigned storage bin is located on the same floor. Enjoy beautiful views of Spring Lake and the evening sunsets from most rooms. Shopping, medical, hospital, places of worship, groceries, restaurants & bus line are very close by. COVERED ASSIGNED PARKING SPACE. SharePoint electric car charger on site for owners! Measurements are approximate. Information is believed to be accurate but not guaranteed. NON-SMOKING COMPLEX THAT IS WELL MAINTAINED & MANAGED. FURNITURE IS NEGOTIABLE. Make this your full-time or winter home!

1776 6th Street Nw Unit 308, Winter Haven

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