Winter Garden Homes with Maintenance Amenities

Winter Garden Homes with Maintenance Amenities

Welcome to Winter Garden, Florida – a vibrant city that beautifully blends historic charm with modern conveniences. Nestled in Orange County, this picturesque locale is known for its lush landscapes, friendly community, and a rich history that dates back to the late 1800s. With its stunning downtown area, filled with quaint shops, delightful eateries, and a lively farmers market, Winter Garden offers a unique lifestyle that appeals to both families and retirees alike.

One of the standout features of living in Winter Garden is the availability of homes with maintenance amenities. Imagine coming home to a beautifully maintained property where lawn care, landscaping, and exterior upkeep are taken care of for you. This means more time to enjoy the many recreational activities that Winter Garden has to offer, from exploring the scenic West Orange Trail to unwinding at the local parks and gardens.

The community is also home to a variety of residential options, ranging from charming single-family homes to modern townhouses, all designed with your comfort in mind. Many of these residences are part of well-planned communities that provide additional amenities such as swimming pools, fitness centers, and clubhouses, ensuring that residents can enjoy a resort-like lifestyle right at their doorstep.

Whether you’re seeking a peaceful retreat or an active lifestyle, Winter Garden is the perfect place to call home. With its warm climate, welcoming atmosphere, and a strong sense of community, you’ll find that life in Winter Garden is simply delightful. Come discover why so many choose to make this enchanting city their home!

Newest Winter Garden Homes with Maintenance Amenities

8943 Lakeshore Pointe Drive, Winter Garden
$639,900
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Phase I SubDv. ⋅ 34787 Zip Code
ONE OF THE PRETTIEST LOCATIONS AND VIEWS IN LAKESHORE!! SHOWS BETTER THAN A MODEL WITH TOO MANY UPGRADES TO LIST!!! LOCATION, LOCATION, LOCATION!!! FROM THE TIME YOU ARRIVE, YOU WILL IMMEDIATELY FALL IN LOVE WITH THE OVERSIZED FRONT PORCH, WATERVIEW OF THE COMMUNITY FOUNTAIN, AND MORE THAN ENOUGH ROOM TO ENJOY OUTDOOR LIVING! THIS LUXURIOUS TOLL BROTHERS DANTE ITALIANATE FLOORPLAN HAS IT ALL! THIS HOME HAS AN OPEN CONCEPT WITH HIGH CEILINGS, LOTS OF WINDOWS ALLOWING FOR NATURAL LIGHT, HUGE SLIDING DOORS WHICH LEAD TO A PRIVATE BRICK PAVERED COURTYARD AND A COVERED WALKWAY TO YOUR TWO CAR GARAGE. WALK INTO YOUR SPACIOUS KITCHEN WHICH INCLUDES A MASSIVE ISLAND AND AN ADDITIONAL BREAKFAST BAR, BOTH WITH UPGRADED QUARTZ COUNTERTOPS. YOU WILL LOVE YOUR NEW KITCHEN WHICH INCLUDES AN UPGRADED CABINET PACKAGE ADDING ADDITIONAL CABINETS FOR AMPLE SPACE, 42" CABINETS, CROWN MOLDING, STAINLESS APPLIANCES AND NATURAL GAS FOR COOKING. MANY ENERGY SAVING FEATURES INCLUDING TANKLESS WATER HEATER, FOAM INSULATION, SOLID CONCRETE BLOCK WALLS FROM THE FOUNDATION THROUGH THE ATTIC AND MORE. ENJOY RESORT STYLE AMENITIES WHICH INCLUDE A POOL, FITNESS CENTER, CLUBHOUSE WITH BREATHTAKING LAKE AND GOLF COURSE VIEWS, KAYAK AND PADDLE BOARD LAUNCH, TWO PLAYGROUNDS, FIREPIT, SUMMER KITCHEN, HAMMOCKS AND DOG PARK. LAKESHORE PRESERVE IS LOCATED IN THE HAMLIN AREA, ONLY TEN MINUTES FROM MAJOR TOURIST ATTRACTIONS. YOU WILL ALSO FIND NEW SCHOOLS, NEW RESTAURANTS, NEW HOSPITAL, PLENTY OF SHOPPING AND ENJOY THE NEW CINEPOLIS RECENTLY BUILT - EASY ACCESS TO ALL THAT CENTRAL FLORIDA HAS!! SCHEDULE YOUR APPOINTMENT TODAY, YOU WILL NOT BE DISAPPOINTED!!!

8943 Lakeshore Pointe Drive, Winter Garden
14501 Grove Resort Avenue Unit 2539, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
BEST-PRICED UNIT CURRENTLY AVAILABLE AT THE GROVE RESORT! This 5th-floor Birch residence is located in desirable Tower 2, the newest tower at The Grove and featuring the resort's most updated décor and finishes. Enjoy a peaceful garden view from this fully furnished resort residence just minutes from Walt Disney World. The Grove Resort & Water Park offers an exceptional combination of vacation ownership and resort amenities, including Surfari Water Park, multiple pools, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, market and coffee shop, and on-site resort management. An outstanding opportunity for buyers looking for an entry point into one of Orlando's most established condo-hotel resorts at the best price currently offered. Financial information and ownership details available upon request.

14501 Grove Resort Avenue Unit 2539, 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
1032 Galston Alley, Winter Garden
$1,625,000
6 Beds ⋅ 5 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Built by RCB Custom Homes as the builder’s personal residence, this exceptional 5-bedroom, 5-bath residence offers 3,506 square feet of thoughtfully designed luxury in the highly desirable Oakland Park neighborhood. Completely remodeled within the past two years, no detail was overlooked in creating a home that is as refined as it is comfortable. Beautiful new hardwood flooring, custom wood beams, designer wallpaper, upscale tile selections, custom cabinetry, premium appliances, and an antique barn wood fireplace treatment create distinctive character throughout. Custom automated blinds and a complete repaint add the finishing touches to this beautifully curated home. Designed for both everyday living and entertaining, the home features inviting screened front and side porches, with an outdoor kitchen. The premium lot faces a long green park with views of Lake Apopka, adjacent to the community clubhouse & amenities . Beyond the beautiful finishes are the exceptional behind-the-scenes upgrades that truly set this home apart, including a whole-home generator, spray foam insulation for impressive energy efficiency, an expansive climate-controlled attic offering valuable conditioned storage, and wiring in place for a future water treatment system. Enjoy all that Oakland Park has to offer, including two community pools and a prime location within the golf cart district. A complete list of upgrades and improvements is available upon request. This is a rare opportunity to own a meticulously remodeled custom residence where luxury, craftsmanship, comfort, and thoughtful design come together.

1032 Galston Alley, Winter Garden
72 N Park Avenue Unit 8, Winter Garden
$1,099,000
3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden
7301 Wild Blackberry Trail, Winter Garden
$2,400,000
6 Beds ⋅ 5 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. This statuesque Mediterranean home is perfectly placed along Hancock Lake for maximum lakefront enjoyment. Your private covered dock protects a 20’ +/- boat w/lift as well as the lifts for 2 jet skis. Motor boat or pontoon around the lake, bring your favorite fishing rod or ski on one of the nicest skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, one of a few lakefront properties in the neighborhood that have one, manicured gardening beds for your green thumb and room for outdoor activities and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry and a delightful custom salt pool showcasing a water slide, fiber optic lighting, solar heated spa and pool ledge. Enjoy the lake views then after sunset, pull down the projector screen for your favorite flick before watching the nightly fireworks show from the Disney park. The home's exterior and interior were freshly painted. Notice the wide baseboards and crown trim throughout. Spectacular front entrance with impressive light fixtures that accentuate the formal living and dining areas and frame your first glimpse of the lake. Impressive, upgraded Double Pane Low E sliding doors showcase the patio and lake then pocket to merge your spaces. The Kitchen is equipped with multiple food prep areas, generous walk-in pantry, and a central island workstation with seating for informal gatherings. A hallway behind the Kitchen shares the cabana bath and another first floor bedroom or den or office with a sliding door to the patio and a sizable walk-in closet. The first level’s primary suite has private patio access too and a lovely bay window styled seating area. (The previous owners used this primary as a media room complete with surround sound that remains intact). The loft also has new sliding doors to the screened balcony area overlooking the patio and lake along with projection equipment and bar/kitchen ideal for entertaining. The upper level contains a large ensuite with a private balcony, another ensuite, two bedrooms that share a hall bath and another bedroom with a private balcony overlooking the patio. The security system is located in the upstairs laundry room. Both A/C Systems, all patio doors, exterior balcony railings secured and LR/DR bamboo engineered hardwood flooring are updates you'll appreciate. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy. Plans for the new satellite elementary campus of Windemere Preparatory School are underway that will be located less than 2 miles from this home. ***Photos of fireworks and formal dining area are THE ONLY PHOTOS virtually staged.

7301 Wild Blackberry Trail, Winter Garden
14501 Grove Resort Avenue Unit 2703, Winter Garden
$295,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2703, Winter Garden
9572 Waterway Passage Drive, Winter Garden
$840,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Why wait for new construction when you can have the Florida lifestyle you want—already completed, upgraded, and ready to enjoy? Recent appraisal completed in 10/2026 valued the property at current asking price. Welcome to 9572 Waterway Passage, a beautifully upgraded D.R. Horton Cresswell in highly sought-after Waterleigh in Winter Garden. If you're considering new construction, this home offers something a brand-new build simply can't: a move-in-ready home with thousands of dollars in thoughtful improvements already completed and an outdoor living experience designed to be enjoyed from day one. Inside, you'll immediately notice the difference. Laminate flooring extends throughout the main living areas for a clean, modern look, while a dramatic geometric accent wall adds designer style to the loft and staircase. The spacious primary suite has been elevated into a true retreat with a fully customized walk-in closet and beautifully renovated en-suite bathroom. The guest bathroom has also been tastefully updated with contemporary finishes. But the real wow factor is outside. Step into your own private Florida oasis, complete with a sparkling pool and spa, fully equipped outdoor kitchen, built-in Bluetooth speakers, privacy landscaping and low-maintenance artificial turf. Permanent exterior lighting creates an inviting ambiance and showcases the home beautifully day and night. This isn't an outdoor space you'll have to imagine someday—it is already finished and ready for pool days, backyard gatherings and relaxing Florida evenings. And there's even more value where it matters: owned solar panels provide the potential for improved energy efficiency and reduced utility costs. For buyers comparing this home with new construction, consider what you're getting here: no waiting for construction to finish, no starting from scratch with landscaping and outdoor improvements, and no need to spend years adding the upgrades that make a house feel truly special. The major transformation has already been done for you. And you still get the Waterleigh lifestyle you've been looking for, with resort-style amenities, recreation, shopping, dining, entertainment and convenient access to major roadways—all in one of Winter Garden's most desirable communities. New construction gives you a blank canvas. This home gives you the finished vision. Beautifully upgraded. Fully equipped for entertaining. Designed for Florida living. 9572 Waterway Passage is the opportunity to stop waiting for the home you want and start enjoying it now. Schedule your private showing today and see why this may be the smarter alternative to starting over with new construction.

9572 Waterway Passage Drive, Winter Garden
15929 Moonlight Bay Street, Winter Garden
$565,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Property in a prime area right behind the Disney parks that lets you enjoy the parks' fireworks. In an excellent community to live in, just 1 block from one of the community pools, and inside are A1+ schools, so don't wait to come see your new home!

15929 Moonlight Bay Street, Winter Garden
200 Southern Pecan Circle Unit 104, Winter Garden
$290,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code
**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden
15725 Sweet Limetta Drive, Winter Garden
$649,900
3 Beds ⋅ 3 Baths ⋅ Highlands/Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Spacious single-story living in the heart of Horizon West! Offering 2,571 square feet, this beautifully upgraded 3-bedroom, 2.5-bath home features an oversized dedicated office and a thoughtfully designed open floor plan with impressive space for both everyday living and entertaining. From the covered front porch and brick-paver driveway to the 10-foot ceilings, 8-foot doors, and crown molding throughout, this home stands out from the moment you arrive. At the heart of the home is a showstopping gourmet kitchen featuring a massive 12-foot granite island, 42-inch cabinetry, gas range, walk-in pantry, and abundant prep and storage space. The kitchen flows seamlessly into the dining and living areas, where oversized triple sliding glass doors fill the space with natural light and extend the living area outdoors. The private primary suite features a spacious walk-in closet, dual vanities, and an oversized walk-in shower, while two generously sized secondary bedrooms share a convenient Jack-and-Jill bath. A large dedicated office provides exceptional flexibility for working from home, a study, hobby room, or additional living space. Outside, enjoy a covered brick-paver lanai complete with outdoor cabinetry, refrigerator, TV area, ceiling fan, and gas hookup, all overlooking a fully fenced backyard ready for year-round Florida living. Additional features include a tankless gas water heater, smart thermostat, smart garage door openers, and a two-car garage. Highlands at Summerlake residents enjoy community amenities including a pool, tennis courts, dog park, playgrounds, sports fields, picnic areas, and internet included with the HOA. Conveniently located near Hamlin Town Center, shopping, dining, schools, SR-429, and Walt Disney World. If you've been searching for the space of a larger home without the stairs, this is the one to see.

15725 Sweet Limetta Drive, Winter Garden
15709 Shorebird Lane, Winter Garden
$849,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Check out the 3D tour. Welcome to this stunning Toll Brothers Sanibel Spanish Colonial model, where timeless architecture meets modern luxury in the highly sought-after Lakeshore Preserve community. Distinguished by its elegant tile roof and thoughtfully designed floor plan, this exceptional home offers the perfect blend of sophistication, comfort, and functionality. Step inside to discover a massive great room that serves as the heart of the home—an inviting space designed for both everyday living and unforgettable entertaining. The gourmet kitchen is a chef's dream, featuring a natural gas range, quartz counters, oversized center island, abundant cabinetry, and seamless flow into the living and dining areas. Two expansive sliding glass doors, complete with custom blinds, open to a covered and screened lanai, creating the ideal indoor-outdoor living experience for relaxing or hosting guests year-round. The first floor also includes a versatile fourth bedroom or private home office with an adjacent full bathroom, providing flexibility for guests, multigenerational living, or remote work. Upstairs, the luxurious primary suite offers a peaceful retreat with large windows that fill the room with natural light. The spa-inspired primary bath features a soaking tub, separate walk-in shower, dual vanities, and twin walk-in closets. Two additional bedrooms, a spacious loft perfect for a media room or play area, and a convenient second-floor laundry room complete the upper level. Additional upgrades include a tankless water heater and a spacious two-car attached garage with a wireless door opener via remote app and has ample room for vehicles and storage. Living in Lakeshore Preserve means enjoying a low-maintenance lifestyle with HOA dues that include lawn care with annual mulch, internet, and cable. Residents also have access to an impressive collection of resort-style amenities, including a clubhouse, swimming pool, fitness center, playgrounds, sand volleyball courts, dog park, firepit, and kayak launch. Extra wide sidewalks allow for easy activities like running, biking, etc. Close to both Elementary as well as High Schools. Home includes a transferable, structural warranty from Toll Brothers builders (over 2 years left). Experience luxury living, exceptional amenities, and an unbeatable location in one of the area's most desirable communities.

15709 Shorebird Lane, Winter Garden
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