Winter Garden Homes with Garden View

Winter Garden Homes with Garden View

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County, where vibrant history meets modern living. With its picturesque downtown, adorned with historic buildings and lush greenery, Winter Garden is a delightful blend of small-town charm and contemporary conveniences. The city is known for its friendly community, top-notch schools, and an array of recreational activities, making it a perfect place for families and individuals alike.

One of the standout features of Winter Garden is its stunning homes with garden views. Imagine waking up each morning to the gentle rustle of leaves and the vibrant colors of blooming flowers just outside your window. These homes are designed to enhance your connection with nature, offering serene outdoor spaces where you can unwind, entertain, or simply enjoy the beauty of Florida’s flora. Many properties boast spacious backyards, perfect for gardening enthusiasts or those who simply want a private oasis to relax in.

The city is also home to the West Orange Trail, a scenic 22-mile stretch that invites outdoor enthusiasts to explore on foot or by bike. Whether you’re strolling through the historic downtown or enjoying a weekend farmers’ market, you’ll quickly discover why Winter Garden is a sought-after destination for prospective homeowners.

With a variety of homes featuring garden views, Winter Garden offers a unique opportunity to embrace a lifestyle that harmonizes comfort, beauty, and community. Come discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Winter Garden Homes with Garden View

921 Westcliffe Drive, Winter Garden
$570,000
4 Beds ⋅ 3 Baths ⋅ Fullers Lndg B SubDv. ⋅ 34787 Zip Code
Discover the luxury of space in this beautifully maintained former Maronda Homes model, nestled on a cul de sac in Winter Garden. Set on a generous half acre lot with mature trees and custom landscaping, this home offers over 2,354 square feet of living space with four bedrooms, two and a half bathrooms, a dedicated office, and an upstairs bonus loft. A striking two story foyer welcomes you with natural light, while a separate dining room and an office with French doors add elegance and versatility. The spacious living room features custom built in details and flows seamlessly into a kitchen with warm wood cabinetry, stainless steel appliances, a center island, and a water filtration system. Upstairs, the primary suite provides a relaxing retreat with dual sinks, a soaking tub, and a separate shower. Sliding glass doors lead to a backyard patio and an expansive lawn enclosed with vinyl fencing, offering a beautiful setting for outdoor dining, entertaining, and quiet afternoons beneath mature shade trees. Thoughtful improvements include a roof replaced in July 2022, HVAC systems installed in 2022, and a new water heater in 2026. The garage features an 18 SEER air conditioning system installed in 2020 and an epoxy floor completed in 2023. Exterior painting approximately two years ago adds to the home’s cared for appeal. Approximately ten minutes from Plant Street’s charming shops and dining, with convenient access to Walt Disney World and Universal Orlando, this inviting home combines spacious living with the best of the Winter Garden lifestyle.

921 Westcliffe 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
324 E Fullers Cross Road, Winter Garden
$520,000
3 Beds ⋅ 2 Baths ⋅ Magnolia Wood Third Addition SubDv. ⋅ 34787 Zip Code
Welcome to this inviting 3-bedroom, 2-bath home in the desirable Winter Garden Golf Cart District. NEW ROOF to be completed by the end of October. Situated on a 0.40 acre, fully fenced lot with a electric gated entrance. This property offers space, privacy, and plenty of opportunities to enjoy the Florida lifestyle. Relax by the private pool, entertain guests on the screened lanai, or enjoy the ample backyard space with gorgeous oak trees. This home features two living spaces, offering ample room and a wood-burning fireplace. An enclosed under-air back porch provides extra space for a den, office, or loft. Two storage sheds with electricity offer convenient room for tools, equipment, and outdoor essentials. Save on irrigation with the dedicated well. Conveniently located near shopping, dining, parks, and major roadways, this home combines outdoor living with everyday convenience in the heart of Winter Garden. Don't miss this opportunity to enjoy the space, features, and location this property has to offer!

324 E Fullers Cross Road, Winter Garden
1316 Southern Sun Drive, Oakland
$1,050,000
5 Beds ⋅ 4 Baths ⋅ Hull Island SubDv. ⋅ 34787 Zip Code
Discover a private retreat in Hull Island at Oakland, an intimate community of limited residences offering a peaceful, exclusive feel near charming downtown Winter Garden and the celebrated West Orange Trail. Enjoy community amenities and a dock for taking in sunrise along Lake Apopka. With no immediate rear neighbors or neighbors on one side, this home backs to a conservation area for added privacy and a natural backdrop. Featuring 5 bedrooms, 4 full bathrooms and 3,658 square feet, the home offers an open kitchen, a versatile loft and a primary suite with its own screened porch overlooking nature. A rear patio with pavers and a covered screened enclosure creates an inviting setting for relaxing and entertaining. Room to gather, space to unwind and a setting to enjoy. Schedule your private showing.

1316 Southern Sun Drive, Oakland
13557 Parkfield Way, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Encore At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location!  Minutes from Walt Disney World and all that Winter Garden has to offer with the new hospitals, stores, restaurants, downtown Winter Garden, Horizon West and the list goes on! Single stories are hard to come by and this MI Home is waiting for you!  It sits on a gorgeous conservation lot with no neighbors on one side. Sit on the front porch or the back patio and enjoy the good life!  Walk to the pool, fitness center and dog park. The perfect community to walk or bike.  This 4 bedroom 3 bath rare find single story is move in ready-well maintained, built in 2021, quartz countertops, NEW AC, huge walk-in closet in the primary bedroom, a popular 3 way split floor plan, and ample room for entertaining with the dining room and large family room.  The home is stunning with its gorgeous wooded and pond view. Lawn Care is included in the HOA leaving you time to enjoy all Central Florida has to offer!  Schedule your showing today!

13557 Parkfield Way, Winter Garden
776 Orange Belt Loop, Winter Garden
$710,000
3 Beds ⋅ 2 Baths ⋅ Heritage/Plant Street SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location is everything in this highly sought-after Golf Cart District of Downtown Winter Garden, where location and lifestyle come together! Situated right off the scenic West Orange Trail, this home places you just moments from the charm, restaurants, shopping, and entertainment of historic Downtown Winter Garden. Best of all, this is a golf-cart-approved area, making it easy to enjoy everything this vibrant community has to offer without getting in the car. From the moment you arrive, you'll appreciate the lush landscaping, paver driveway, and charming front porch. Step inside to a welcoming foyer, with two spacious secondary bedrooms and a full bathroom conveniently located at the front of the home. Continue into the heart of the home, where the open-concept family room, dining area, and stunning gourmet kitchen create the perfect space for everyday living and entertaining. The kitchen features gas cooking, a wall oven, oversized island with sink, abundant upgraded cabinetry extending to the tall ceilings, a spacious walk-in pantry, and a convenient built-in drop zone. The home also offers a separate laundry room complete with washer and dryer and a laundry tub for added convenience. Privately tucked away at the rear of the home, the spacious primary suite provides a peaceful retreat. The spa-inspired primary bathroom features a large glass-enclosed shower, dual-sink vanity, separate water closet, and generous walk-in closet. Step outside to the screened-in lanai, complete with an electric retractable screen wall, creating an ideal setting for relaxing, entertaining, or enjoying Florida's beautiful weather. Additional features include a whole-home water filtration system, adding another level of comfort and convenience. And the location truly sets this home apart. Enjoy easy access to the 35-mile West Orange Trail, while being just minutes from Downtown Winter Garden's award-winning restaurants, charming local shops, Crooked Can Brewery, and the renowned Winter Garden Farmers Market. You'll love the genuine hometown atmosphere and the convenience of being able to experience so much of it by golf cart. With HOA dues that include lawn maintenance, this home offers a low-maintenance lifestyle in one of Winter Garden's most desirable areas. Homes in the Golf Cart District rarely come available and are highly sought after. Don't miss the opportunity to make this exceptional Downtown Winter Garden home your own!

776 Orange Belt Loop, Winter Garden
14501 Grove Resort Avenue Unit 3703, Winter Garden
$178,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to Your Premier Vacation Gateway at The Grove Resort & Water Park! Located just minutes from Walt Disney World and Orlando’s world-class attractions, this fully furnished 2-bedroom, 2-bathroom condo-hotel unit (#3703) offers the perfect blend of vacation luxury and income-generating potential! ***PRIME CENTRAL VIEW: Positioned directly facing the lush central garden and courtyard, providing a peaceful, scenic backdrop and elevated tropical views right from your private space. ***UNRIVALED RESORT AMENITIES: Guests and owners enjoy full access to the renowned Surfari Water Park, dual water slides, lazy river, FlowRider® surf simulator, zero-entry pools, spa, game room, and multiple on-site dining options. ***TURNKEY & HASSLE-FREE: Professionally managed with on-site rental program options, making personal vacation stays and short-term rentals seamless.*** Whether you're seeking a vacation home, a smart investment property, or a hybrid of both, Unit #3703 delivers unbeatable lifestyle and convenience in the heart of Central Florida's tourism corridor. Schedule your showing today!!

14501 Grove Resort Avenue Unit 3703, Winter Garden
8091 Bowery Drive, Winter Garden
$585,000
4 Beds ⋅ 3 Baths ⋅ Lake Hancock Preserve SubDv. ⋅ 34787 Zip Code
Discover refined living in this beautifully appointed corner-lot residence in desirable Horizon West. Designed with elegance and everyday comfort in mind, this exceptional home features a spacious open floor plan, split-bedroom design, 4 bedrooms, 3 full baths, and a versatile den. The gourmet kitchen showcases 48-inch cabinetry, a beautiful glass-front display cabinet, and granite countertops, creating a nice space for both everyday living and entertaining. The corner setting provides abundant natural light and enhanced privacy, while the HOA includes lawn maintenance for added convenience. Ideally located near Publix, Walmart, Starbucks, restaurants, cafés, Cinepolis Luxury Cinemas, Urban Air Trampoline Park, and highly rated schools. Convenient access to Hwy 429 and Hwy 535.

8091 Bowery Drive, Winter Garden
128 N Highland Avenue, Winter Garden
$965,000
4 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to a piece of history, right in the Winter Garden's golf cart district! This stunning Craftsman bungalow is nestled in the Historic District, where timeless character meets extensive modern updates. Set on a 0.34-acre lot beneath grandfather oaks, this home creates an atmosphere that feels peaceful while placing you just steps from the energy of downtown. From the moment you arrive, you're greeted by a gravel driveway(2021) that leads to the front of the property, while outdoor lighting (2021) creates a welcoming glow as the sun goes down. Step through the beautiful leaded glass front door into a home filled with warmth and character. Rich heart pine floors, 9-foot ceilings, and crown molding create a timeless backdrop that is sure to make everyone feel at home.The front living and dining area provides a comfortable place to entertain or settle in with loved ones. Nearby, a flexible room can function as a bedroom or home office, and includes its own half bath, giving you the freedom to shape the space around your family's needs. At the center of the home, the farmhouse-inspired kitchen includes real wood cabinetry, granite countertops, and a convenient side entry to make everything from everyday cooking to hosting dinners feel effortless. The side entrance also makes bringing in groceries especially convenient. Down the hall, two bedrooms create comfortable retreats and share a guest bathroom with subway tile detailing. The guest bathroom tub drain line was replaced in 2025, while extensive flooring and subfloor improvements completed throughout the home provide a refreshed foundation from room to room. Upstairs, you’ll find the new flooring that was installed in 2025, along with recessed lighting (2018), and a bright and inviting loft space with flexibility for a reading area or home office. The primary bedroom was remodeled in 2025 and includes a custom built-in closet for exceptional organization. The upstairs bathroom was also remodeled in 2025, creating a beautifully updated space to begin and end your day. The home has received extensive upgrades, providing the new owners with peace of mind that this home was truly cared for. Upgrades include a downstairs HVAC system (2023), a replacement of the downstairs ductwork (2025), foundation support installed beneath the rear half of the home with concrete footers (2024), and a new water heater (2025). The home's exterior has been refreshed as well, including Artificial turf (2021) for easy upkeep, new exterior paint (Dec, 2024) and a new roof (2023). Heading outside, you're bound to love the private fenced in backyard space. Whether you're imagining weekend gatherings, letting little ones play, or simply enjoying a quiet afternoon outdoors, there's room to create the backyard you've always wanted. The detached 25' x 25' garage and workshop adds another layer of flexibility, complete with 100-amp electrical service. For a hobbyist, craftsman, or anyone who needs additional storage and workspace, this building can become whatever your lifestyle requires.This is a home with character you simply can't recreate, paired with the extensive updates and improvements. And perhaps best of all, you're living in the heart of Historic Downtown Winter Garden, where morning walks, farmers markets, local dining, shopping, live entertainment, and community events can become part of your daily routine. Don't wait on this amazing home, schedule your private showing TODAY!

128 N Highland Avenue, Winter Garden
14501 Grove Resort Avenue Unit 3201, Winter Garden
$245,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
FULLY FURNISHED/TURNKEY LUXURIOUS 3/3 Corner Unit at The Grove Resort & Spa, Orlando Welcome to your dream oasis at The Grove Resort & Spa Orlando! This magnificent corner unit boasts the LARGEST floor plan available, featuring 3 spacious bedrooms and 3 elegant bathrooms. Experience the ultimate blend of comfort and luxury in this stunning condo-hotel located just six miles from Walt Disney World® Theme Parks, The Grove Resort & Spa offers unparalleled access to Orlando’s world-famous attractions. Enjoy daily transportation to Walt Disney World®, Universal Orlando, and SeaWorld, making it effortless to explore all that Orlando has to provide. Indulge in a variety of resort amenities designed for both relaxation and adventure. The Surfari Water Park features thrilling water slides, a lazy river, and the exhilarating FlowRider® Double surf simulator. Unwind at The Springs Pools, with three full-sized pools, an oversized hot tub, and poolside bar service. At Lake Austin, engage in catch-and-release fishing, paddle boating, or simply savor the serene views of the surrounding nature preserve. Stay active with a fully-equipped fitness center and scenic jogging paths. Families will love Flip Flop’s Family Fun Center, offering the latest arcade games and a glow-in-the-dark mini golf course. This corner unit is designed with a modern touch, offering a spacious open-plan living area, a gourmet kitchen, and stylish furnishings throughout. Each bedroom is a private retreat, complete with luxurious bedding and ample storage. Owning a unit at The Grove Resort & Spa offers not only a luxurious vacation spot but also a fantastic stress-free investment opportunity. Don’t miss the opportunity to own a piece of paradise at The Grove Resort & Spa, where every day feels like a vacation. Contact us today to schedule a private viewing and experience the exceptional lifestyle that awaits you.

14501 Grove Resort Avenue Unit 3201, Winter Garden
1720 Lake Roberts Landing Drive, Winter Garden
$1,399,999
5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code
Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden
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