Winter Garden Homes with Tennis Court(s) Community Features

Winter Garden Homes with Tennis Court(s) Community Features

Welcome to Winter Garden, Florida – a charming city nestled in Orange County that beautifully blends small-town warmth with modern conveniences. Known for its picturesque landscapes and vibrant downtown area, Winter Garden offers residents a unique lifestyle filled with abundant recreational opportunities, delightful dining options, and a strong sense of community.

As you explore the homes in Winter Garden, you’ll discover an array of properties featuring luxurious amenities, including tennis courts. Imagine stepping into your backyard and enjoying a match with friends or family, all while basking in the Florida sunshine. Homes with tennis courts in this area are not just about sport; they embody a lifestyle of health, wellness, and social engagement.

The community features surrounding these homes are designed to enhance your living experience. Many neighborhoods are equipped with beautifully maintained tennis courts, clubhouses, and community pools, making it easy for residents to connect and enjoy leisure activities. The lush landscapes and well-planned amenities create an inviting atmosphere for families, retirees, and everyone in between.

Winter Garden's proximity to major highways and the bustling city of Orlando means you can enjoy a peaceful suburban lifestyle while having quick access to urban excitement. Whether you're strolling through the historic downtown, savoring a meal at a local café, or participating in community events, Winter Garden is a place where memories are made and friendships thrive.

Discover your dream home with a tennis court in Winter Garden and embrace the active lifestyle that awaits you in this delightful Florida gem!

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

9279 Grand Island Way, Winter Garden
$505,000
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 2c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 9279 Grand Island Way, a beautifully appointed 3-bedroom, 2.5-bathroom residence situated on a desirable corner lot in the sought-after Watermark community of Horizon West in Winter Garden. Offering the perfect blend of modern style, comfort, and convenience, this recently painted two-story home features brand-new luxury vinyl flooring throughout the first floor and an inviting open-concept floor plan designed for both everyday living and effortless entertaining. Step inside to discover a bright and spacious living area filled with natural light, complemented by beautiful new luxury vinyl flooring and a modern kitchen featuring granite countertops, 42-inch cabinetry, stylish pendant lighting, and ample counter space. The kitchen flows seamlessly into the dining and living areas, creating an ideal setting for gatherings with family and friends. A convenient half bathroom and access to the two-car garage complete the first floor. Upstairs, a versatile loft provides additional living space, perfect for a home office, media room, playroom, or private lounge. The spacious primary suite offers a relaxing retreat with an en-suite bathroom and walk-in closet, while two additional bedrooms provide comfortable accommodations for family or guests. The home's desirable corner-lot location allows for abundant natural light, enhancing its open and welcoming atmosphere. One of the property's standout features is its exceptional location directly across from the Horizon West retail and dining center, placing everyday conveniences just moments from your doorstep. Enjoy easy access to Starbucks, New York Beer Project, Walgreens, and a variety of nearby shopping, dining, and entertainment options. The ability to walk or bike to neighborhood favorites adds to the appeal of this vibrant community. Residents of Watermark enjoy an impressive collection of resort-style amenities, including a community swimming pool with splash pad, clubhouse, fitness center, tennis courts, playgrounds, and scenic walking trails, offering recreation and relaxation just minutes from home. Ideally situated near Hamlin Town Center, Orange County National Golf Center, major roadways including SR 429, and Walt Disney World, this home provides convenient access to everything that makes Horizon West one of Central Florida's most desirable places to live. Experience the perfect combination of location, lifestyle, and modern comfort at 9279 Grand Island Way. Welcome home!

9279 Grand Island Way, Winter Garden
9662 Waterway Passage Drive, Winter Garden
$515,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2a SubDv. ⋅ 34787 Zip Code
SELLER IS OFFERING 5K IN UPGRADE CONCESSIONS for whatever your heart desires. BEST Price in the neighborhood! Premium CORNER lot w/ community green space (play areas for the little ones). This is one of the few larger lots (7,809 sq ft) in the community. You won't find a better deal in Waterleigh! ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- This 3/2.5 + LOFT home is the perfect buy. You know the old saying, buy the smaller house in the big expensive neighborhood. Some neighbors' homes are valued at over a million dollars. Your property will benefit from the increasing value. Well, this is it. Offering 2,014 square feet of living space, it is the perfect size for a growing family without all the heavy cleaning! -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- As an added bonus, the HOA includes landscaping, allowing for truly low-maintenance living. Beyond the home itself, you'll fall in love with the incredible resort-style amenities this sought-after community has to offer, including multiple pools, fitness centers, tennis courts, sand volleyball court, mini golf course, playgrounds, scenic walking trails, community dock and a vibrant calendar of community events throughout the year. Everyday conveniences are just a golf cart ride away, including Publix, Jersey Mike's, a nail salon & Kiddie Academy. --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- This golf cart-friendly community was designed to make life easy, fun, and connected. Located in the highly desirable Horizon West area and zoned for Atwater Bay Elementary, you'll be just minutes from shopping, dining, entertainment, and outdoor recreation. Enjoy the charm of historic Downtown Winter Garden, the scenic West Orange Trail, and easy access to Orlando's world-famous attractions and theme parks. This home offers more than just beautiful living spaces, it offers a lifestyle. Why wait months to build when you can move right into a highly upgraded, turnkey home today?

9662 Waterway Passage Drive, Winter Garden
13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden
15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden
16742 Oakboro Street, Winter Garden
$519,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this better-than-new 4-bedroom, 2.5-bathroom home in the highly desirable Waterleigh community of Horizon West! Built in 2020, this thoughtfully upgraded home offers 2,014 square feet of living space, an inviting open-concept layout ideal for entertaining, and the convenience of a first-floor primary suite featuring a custom closet. The kitchen boasts granite countertops, stainless steel appliances, a touch-activated pull-down faucet, and a spacious butler’s pantry offering abundant storage. Additional owner upgrades include matte black hardware and ceiling fans throughout, smart light switches and fans, and a Fisher & Paykel washer and dryer. Enjoy Florida living year-round on the screened-in lanai, with added peace of mind from the upgraded fenced yard featuring two gates and puppy pickets, a complete gutter system, and electrical wiring ready for a whole-house generator. The garage is equipped with overhead storage and is EV-ready with an installed Tesla charger. Waterleigh residents enjoy an exceptional array of amenities, including two resort-style clubhouses and pools, two fitness centers, putt-putt golf, beach volleyball, tennis, a lake-view picnic area, a dog park, and more. With its desirable location, modern conveniences, and extensive upgrades, this home offers a wonderful opportunity to enjoy the best of the Waterleigh lifestyle!

16742 Oakboro Street, Winter Garden
1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden
1349 Castleport Road, Winter Garden
$749,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
SPACIOUS TWO-STORY HOME IN WINTER GARDEN – 5 BEDROOMS, 5 LIVING AREAS & MORE! Discover this beautiful two-story home in Winter Garden, offering an ideal combination of space, comfort, and convenience. Featuring 5 bedrooms, 3 full bathrooms, and 1 half bathroom, this property stands out with an impressive five additional living areas, providing plenty of room for entertaining, relaxing, working from home, or creating spaces tailored to your lifestyle. The open floor plan creates a welcoming atmosphere, complemented by spacious living and dining rooms perfect for gatherings with family and friends. The beautiful kitchen features solid wood cabinets, elegant stone countertops, and included appliances, combining style and functionality for everyday living. The primary bedroom offers a walk-in closet, while the remaining four bedrooms feature built-in closets for convenient storage. With generous interior space and a versatile layout, this home is an excellent option for buyers looking for room to grow or investors seeking an attractive rental property. Additional highlights include a two-car attached garage and a convenient location near a major road, providing easy access to nearby amenities, shopping, dining, and well-regarded schools. Don't miss this opportunity to own a spacious and versatile home in desirable Winter Garden!

1349 Castleport Road, Winter Garden
341 Southern Pecan Circle Unit 202, Winter Garden
$220,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
WINTER GARDEN GEM! NEW KITCHEN • NEW APPLIANCES • NO CARPET • PRIVATE GARAGE • RESORT-STYLE AMENITIES! Welcome to 341 Southern Pecan Circle, Unit 202, Winter Garden, FL 34787! Discover this beautifully updated, move-in-ready 1-bedroom, 1-bathroom condo featuring modern upgrades, open-concept living, a private garage, and outstanding resort-style community amenities in desirable Winter Garden, Central Florida! Step inside to enjoy bright, inviting living and dining areas filled with natural light, fresh interior paint, and NO CARPET THROUGHOUT! Attractive wood-look flooring enhances the living areas and bedroom, complemented by easy-to-maintain tile flooring in the kitchen and bathroom. The NEW KITCHEN showcases beautiful cabinetry, attractive countertops, a spacious breakfast bar, stainless steel appliances, and a NEW REFRIGERATOR AND MICROWAVE! The open layout provides an inviting space for everyday living and entertaining. The spacious bedroom offers generous closet space, while the UPDATED BATHROOM features attractive tile finishes and a convenient vanity. Additional conveniences include an IN-UNIT WASHER AND DRYER and a PRIVATE GARAGE for parking and extra storage. ENJOY RESORT-STYLE LIVING! This amenity-rich community features a sparkling swimming pool, fitness center (gym), basketball court, tennis courts, sand volleyball court, playground, and car wash station. The COMMUNITY CLUBHOUSE also offers a community kitchen, computer room, nursery room, and meeting room, providing excellent spaces for recreation, convenience, and community activities. DESIRABLE WINTER GARDEN LOCATION! Enjoy convenient access to shopping, dining, entertainment, parks, major roadways, and the greater Orlando area. IDEAL FOR LOW-MAINTENANCE LIVING OR INVESTMENT! Whether you're seeking a primary residence, seasonal retreat, convenient home for work or studies, or a potential rental investment, this updated Winter Garden condo offers comfort, functionality, and lifestyle amenities. Rental opportunities are subject to association rules and restrictions. NEW KITCHEN • NEW APPLIANCES • UPDATED BATHROOM • NO CARPET • PRIVATE GARAGE • IN-UNIT LAUNDRY • RESORT-STYLE AMENITIES! SCHEDULE YOUR PRIVATE SHOWING TODAY!

341 Southern Pecan Circle Unit 202, Winter Garden
9469 Meadow Hunt Way, Winter Garden
$485,000
4 Beds ⋅ 3 Baths ⋅ Watermark At Horizon West SubDv. ⋅ 34787 Zip Code
HOME AVAILABLE TO MOVE IN - This 4 bedroom 2.5 bath home is located in the highly desirable Hamlin Community has a GREAT SCHOOL ZONE in the Winter Garden Area!!! This recently built home features street front parking, open living space downstairs with plenty of room for entertaining, all dearooms upstairs and is wired to charge your lesla. Ine nome is minutes tom great senools, great eating at the namin center and in walking distance to the new development "The Mark". The community features clubhouse, dog park, pool, a playground, tennis court. The local snops reature a variety or restaurants, Danks, nealt orices, a rudiix grocery store, Anyume neness gym, and minutes trom Disney!

9469 Meadow Hunt Way, Winter Garden
14825 Porter Road, Winter Garden
$609,998
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Phase 2a And 2b SubDv. ⋅ 34787 Zip Code
Virtually Staged. With 2,732 square feet, a spacious upstairs loft and a downstairs room ready to serve as a fourth bedroom, this Summerlake home gives you room to arrange life as you please. Three bedrooms and 2.5 baths. The open main floor has tile underfoot, plantation shutters and a stone accent wall in the living room. The kitchen offers a granite island with seating, dark wood cabinetry, tile backsplash, gas range and pendant lighting, and opens to the dining area. Sliders lead to a covered paver patio and a fenced backyard with a fire pit. Upstairs, the primary suite has a custom-fitted walk-in closet, double vanity, soaking tub and glass-enclosed shower. Stone-trimmed covered front porch, & a rear-entry garage. Summerlake amenities include a resort-style pool with splash pad, lakefront clubhouse, fitness center, tennis and basketball courts, playgrounds, dog park, fishing pier and walking trails. This home is conveniently located close to the amenities. Close to Hamlin Town Center, SR 429 and a short drive to the Parks.

14825 Porter Road, Winter Garden
7186 Wild Strawberry Run, Winter Garden
$750,000
4 Beds ⋅ 4 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed 4-bedroom, 3.5-bathroom home in the highly desirable Independence community of Winter Garden! Offering a thoughtful blend of space, comfort, and lifestyle, this home features an additional private office, a spacious bonus room, and a unique layout designed for both everyday living and entertaining. Step inside to discover generous living spaces, a modern kitchen perfect for gathering with family and friends, and a spacious primary suite designed for comfort and relaxation. The additional office provides an ideal space for working from home, while the large bonus room offers endless possibilities—a media room, game room, or second family lounge. The home features a convenient half-bath on the first floor, a Jack-and-Jill bathroom, and a detached garage located at the rear of the property, adding character and functionality to the home's layout. Outside, enjoy a nicely sized backyard with room to create your own private outdoor retreat, including the potential to add a pool (subject to applicable approvals). Whether you envision weekend barbecues, outdoor entertaining, or simply relaxing in your own space, the possibilities are yours to explore. What truly makes this location special is the lifestyle waiting right outside your door!Horizon West, offering amenities and outdoor spaces designed to bring recreation, relaxation, and community connection together. Residents can enjoy: Community swimming pools for cooling off and enjoying the Florida sunshine Clubhouses and fitness centers for recreation and wellness Scenic walking and biking trails for outdoor exercise Community parks and playgrounds for outdoor fun Sports courts and beautifully maintained green spaces for an active lifestyle The location is equally appealing, with convenient access to shopping, restaurants, cafés, schools, and everyday essentials. Explore nearby Hamlin and Winter Garden Village for additional dining, shopping, and entertainment options. And when it's time for adventure, Walt Disney World and Central Florida's world-famous attractions are within driving distance, making weekend outings and family fun easy to enjoy. Whether you're looking for room to grow, space to work from home, or a community that offers amenities beyond your front door, this home presents an opportunity to enjoy the best of the Winter Garden lifestyle. Enjoy the space. Embrace the community. Make Winter Garden home.

7186 Wild Strawberry Run, Winter Garden
10079 Austrina Oak Loop, Winter Garden
$880,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Enjoy spacious living, no rear neighbors, and Disney fireworks views in the sought-after Watermark community of Winter Garden! Built by Meritage Homes, this Maison floor plan offers 5 bedrooms, 3.5 bathrooms, and approximately 3,359 square feet of thoughtfully designed living space. A paver driveway and covered front porch create a welcoming first impression, leading into a foyer that opens to the second floor. The main level features a separate dining room and an open kitchen with a center island, pantry, and butler’s pantry. The kitchen connects seamlessly to the spacious family room, creating an inviting setting for everyday living and entertaining. A downstairs bedroom provides flexibility for guests or a home office, with a half bathroom conveniently nearby. Step outside to the covered lanai and enjoy the added privacy of having no rear neighbors, along with views of Disney fireworks. Upstairs, the spacious primary suite features two walk-in closets and an ensuite bathroom with dual vanities, a soaking tub, and a separate shower. Three additional bedrooms and two full bathrooms provide ample space, while the game room offers a versatile area for movies, hobbies, or relaxation. An upstairs laundry room adds everyday convenience, and the two-car garage provides parking and storage. Watermark offers an exceptional collection of resort-style amenities, including a swimming pool with a splash pad, clubhouse, fitness center, tennis courts, playground, park, and outdoor amphitheater. The community’s second-story viewing deck provides another inviting spot to enjoy Disney fireworks. Located in Winter Garden’s desirable Horizon West area near sought-after schools, this home offers convenient access to Hamlin’s shopping, dining, and entertainment, Walt Disney World, and SR-429. Discover a home that brings together generous living space, a versatile floor plan, and outstanding community amenities. Schedule your private showing today!

10079 Austrina Oak Loop, Winter Garden
Start Your Search

How much is your home worth?

Get instant property value now!