Winter Garden Homes with Pool Amenities

Winter Garden Homes with Pool Amenities

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes, vibrant community, and rich history, Winter Garden offers a delightful blend of small-town charm and modern conveniences. With its historic downtown area featuring quaint shops, local eateries, and a scenic waterfront, residents enjoy a lifestyle that’s both relaxed and engaging.

One of the standout features of Winter Garden is its beautiful year-round weather, making it an ideal location for those who appreciate outdoor living. The city boasts an array of recreational opportunities, from lush parks to scenic trails, perfect for walking, biking, or simply enjoying a sunny afternoon.

For homebuyers seeking the ultimate in comfort and leisure, Winter Garden offers an impressive selection of homes with pool amenities. Imagine lounging by your private pool on a warm Florida day, hosting summer barbecues, or enjoying a tranquil evening swim under the stars. These homes are designed with relaxation in mind, often featuring spacious backyards, elegant landscaping, and inviting outdoor spaces that seamlessly blend with the indoor living areas.

Whether you’re a first-time buyer or looking to upgrade, Winter Garden’s real estate market presents a variety of options to suit your lifestyle. With its family-friendly atmosphere, excellent schools, and proximity to Orlando’s attractions, Winter Garden is not just a place to live; it’s a place to thrive. Discover your dream home with a pool in this idyllic community today!

Newest Winter Garden Homes with Pool Amenities

4 Beds ⋅ 4 Baths ⋅ Oakland Park South SubDv. ⋅ 34787 Zip Code

LAKE APOPKA VIEWS FROM THE UPSTAIRS BALCONY. DIRECT ACCESS TO THE WEST ORANGE TRAIL. GOLF CART RIDES TO DOWNTOWN WINTER GARDEN. OVERSIZED THREE-CAR GARAGE. FENCED BACKYARD ADDED IN 2025. CUSTOM PRIMARY CLOSET SYSTEM. CUSTOM BACKYARD DECK. PLANTATION SHUTTERS THROUGHOUT. LOW-MAINTENANCE OUTDOOR SPACE. Start the morning with coffee on the upstairs balcony overlooking Lake Apopka, spend the afternoon biking or walking the West Orange Trail, and take the golf cart into Downtown Winter Garden for dinner, the farmers market, or an evening on Plant Street. Located in Oakland Park, this RockWell Homes Lincoln floor plan offers spacious living with a layout designed for both everyday life and entertaining. The builder included quartz countertops, luxury vinyl plank flooring, and a covered lanai. The primary suite features a custom closet system designed to maximize storage and organization. The oversized three-car garage provides plenty of room for vehicles, storage, bikes, golf carts, and recreational equipment, and the garage floor has been finished with a durable epoxy coating. The owners have also added plantation shutters throughout, a custom backyard deck, French drains to improve drainage around the property, and a fenced backyard completed in 2025. The backyard has no grass to water or mow, creating an easy-to-maintain outdoor space while still providing privacy and room to relax or entertain. Oakland Park is connected to the West Orange Trail and positioned between Oakland and Historic Downtown Winter Garden. Residents can easily enjoy Plant Street’s restaurants, shops, farmers market, community events, and the surrounding golf cart district, all while coming home to a quieter neighborhood setting with views of Lake Apopka.

1234 Canyon Creek Trail, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Seacliff. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. Go down the hallway and you’ll find a powder room and laundry room tucked behind the stairwell leading up to the second floor. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and a walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk in closet. As we head upstairs, you are greeted with a loft area and all three bedrooms. Two bedrooms share a upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. Like all homes in Waterleigh, the Seacliff includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11833 Shine View Lane, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Bellmore. This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a spacious walk in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom. This home features a space to fit all your needs. Like all homes in Waterleigh, the Bellmore includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11923 Shine View Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code

Welcome to this well-maintained home in the highly desirable Orchard Hills community of Horizon West. Enjoy NO CDD fee, a LOW HOA that includes lawn care, and an A-rated school zone. Built in 2017, this thoughtfully designed house offers approximately 2500 sqft with 3 bedrooms + 1 downstairs den/office(convertible to a 4th bedroom) + 1 upstairs loft/retreat + 3 full bathrooms. The modern bright, open floor plan is perfect for both everyday living and entertaining. Upgrades include gorgeous wood-look tile flooring throughout the main living areas and the primary bedroom, plus an upgraded kitchen featuring 42" cabinets and beautiful quartz countertops. For ultimate flexibility, the main level downstairs hosts a full bathroom adjacent to a private office/den which easily serves as a 4th bedroom or guest suite. Upstairs, the expansive primary bedroom boasts a walk-in closet, dual sinks, separate tub and shower, and a private wraparound balcony. Additional highlights include a multi-functional Loft upstairs, a 2.5-car garage and an extra-long driveway that provides plenty of parking. Only 4 mins to Keene's Crossing Elementary and middle school, around 12 mins to Windermere High School and Windermere Preparatory School. Orchard Hills is an amazing community features clubhouse, resort-style pool, state-of-the-art fitness, recreation room, playground, dog park, walking/biking trails, playgrounds, sports field, and a picnic area with grills. Only a few mins to shopping centers, including Hamlin Shopping Center, Stoneybrook West Village, Winter Garden Village, Winter Garden Hospital. 10 mins to Orange County National Golf Center and Lodge. Short drive to Disney World, downtown Winter Garden, Windermere and Orlando. Schedule a showing Today!

14699 Magnolia Ridge Loop, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Waterleigh presents the Bellake. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. The kitchen overlooks the dining and great room, while having view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, plentiful cabinet and counter space and stainless steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play and half bathroom. As we head up to the second floor, we are greeted with Bedroom one which includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well. This home features a two car garage located at the rear of the home complete with drop zone as you enter the home. Like all homes in Waterleigh, the Bellake includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16810 Hobe Sound Court, Winter Garden

6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code

Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Li SubDv. ⋅ 34787 Zip Code

**Spacious 3-bedroom, 3-bathroom fully-furnished condo located on the fourth floor of the beautiful Grove Resort and Water Park! This condo has a full kitchen, full washer and dryer, large primary bedroom with sitting area, large primary bathroom with dual sinks and separate shower and tub, a second bedroom with its own ensuite bathroom, and a third bedroom and bathroom. The screened-in balcony overlooks the central fountain area, so the location is only a short stroll away from any amenities! You have the Surfari water park with a large heated pool, lazy river, water slides, splash area, and the Flowrider surfing experience! The Longboard Bar and Grill is located inside the water park for delicious meals, snacks and drinks! Or visit the Springs Pools area which has three further pools, and the relaxing hot tub! Located next to the Valencia Restaurant, the outdoor bar is also located there, and the 24/7 gym! Take a stroll down to Lake Austin and try your hand at fishing, kayaking, or paddle a swan boat!! For indoor fun visit Flip Flops, the 6000 sf games arcade with glow-in-the-dark mini golf!! For your convenience for food, gifts and sundries, we have the Marketplace, located at the Front Desk area. A free daily shuttle to the Disney parks is also provided for owners and guests. Enjoy ownership of a vacation condo, while having the onsite management company place bookings in your unit while you are not there! It is a completely hands-free experience! Call now for more details!!**

14501 Grove Resort Avenue Unit 3401, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Experience refined living in this exceptional 5-bedroom, 3-full and 2-half bath residence nestled in one of Winter Garden's most desirable communities. Thoughtfully designed with an open-concept floor plan, the expansive great room seamlessly connects to the gourmet kitchen, creating an inviting space for both everyday living and elegant entertaining. The first-floor primary suite offers a private retreat, complete with a spacious layout and spa-inspired bathroom. The primary bath connects to your California style closet and laundry room. Throughout the home, you'll appreciate upscale finishes, including designer lighting, elegant flooring, stone countertops, stainless steel appliances, and architectural details that elevate every space. New carpets and a new Kitchen Aid refrigerator installed in July 2026. Large windows fill the home with natural light, enhancing the bright and airy atmosphere. Four additional bedrooms located upstairs with jack and jill style bathrooms. This home has two bonus areas for maximum entertaining potential, comfort and functionality. This home is also equipped with a whole house water softener, Tesla charger and Govee lights. The backyard is set for entertainment with your summer kitchen, firepit and turf grass. Ideally located near premier shopping, dining, entertainment, parks, and top-rated schools, this home combines luxury, convenience, and timeless style in the heart of Winter Garden. A rare opportunity to own a beautifully appointed turn-key ready home in an exceptional location.

1664 Holcomb Creek St., Winter Garden

3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to The Regina II in Northlake at Ovation, where modern design meets everyday convenience. This thoughtfully crafted home offers spacious living areas perfect for both relaxing and entertaining. Nestled in the highly sought-after Winter Garden area, this home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. This low maintenance townhome includes a detached two car garage with private fenced courtyard space. The open kitchen boasts plenty of modern upgrades from the AW Collection Coastal such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings. The main living areas feature wood look luxury vinyl plank flooring and the bedrooms include upgraded carpet for comfort, plus find upgraded 8' doors throughout the home. Enjoy the neighborhood amenities including a community pool, clubhouse, shaded playground, and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17398 Sweet Moro Drive, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden

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