Winter Garden Homes with HOA

Winter Garden Homes with HOA

Welcome to Winter Garden, Florida—a charming city that beautifully marries the warmth of small-town living with the vibrancy of modern amenities. Nestled just a short drive from the bustling heart of Orlando, Winter Garden boasts a rich history, stunning landscapes, and a welcoming community atmosphere that makes it an ideal place to call home.

One of the standout features of Winter Garden is its picturesque downtown area, where you can stroll along tree-lined streets, explore boutique shops, and savor delicious cuisine at local eateries. The city is also home to the West Orange Trail, a scenic path perfect for walking, biking, or simply enjoying the great outdoors. With its lush parks and beautiful lakes, Winter Garden offers plenty of opportunities for recreational activities and family fun.

For those considering a move to this delightful city, many homes are part of homeowners associations (HOA), ensuring that neighborhoods are well-maintained and fostering a strong sense of community. These HOA-managed properties often come with amenities such as community pools, fitness centers, and organized events, providing residents with a lifestyle that balances convenience and camaraderie.

Whether you’re seeking a cozy single-family home, a modern townhouse, or a luxurious estate, Winter Garden offers a diverse range of housing options to suit various tastes and budgets. Experience the charm, community spirit, and vibrant lifestyle that Winter Garden has to offer—your dream home awaits!

Newest Winter Garden Homes with HOA

480 W Plant Street, Winter Garden
$785,000
2 Beds ⋅ 3 Baths ⋅ O6453345 MLS ⋅ Na BLDG.
In the heart of Historic Downtown Winter Garden, this three-story townhome in Park Place offers a rare blend of architectural character, flexible living spaces, and an exceptional walkable lifestyle. Step inside and discover this well-executed floor plan that lives much larger than its square footage suggests. Soaring 20-foot ceilings, expansive windows, open stair railings, and a custom loft create an impressive sense of space and natural light with an airy feel. The second-floor living area is the centerpiece anchoring the home, featuring custom German Schmear limewashed brick, detailed trim work, a built-in entertainment center, and sliding glass doors that open to a Juliet balcony overlooking downtown. The thoughtfully designed kitchen offers an oversized island with dine-in seating, white wood cabinetry with glass insets, stainless steel Samsung appliances, designer lighting, plantation shutters, and a convenient built-in workspace. Only two of these Park Place floor plans exist. One of the home's most unique features is the custom loft overlooking Plant Street and the West Orange Trail. Complete with a built-in ladder and bench seating, it's an inviting space to read, work, or simply enjoy the view. The first floor offers a private guest suite or study with an en-suite bath and walk-in closet. With special-use permits issued for select Park Place Plant St units, commercial zoning on this level lets you add a professional workspace. Upstairs, the third-floor owner's retreat provides privacy, a spacious walk-in closet, walk-in shower, and additional storage. Lovingly maintained by its original owner for seven years, this home offers low-maintenance, lock-and-leave living in one of Downtown Winter Garden's most desirable locations. The location is hard to beat. Step outside and you're in the heart of what makes Downtown Winter Garden special. Walk to the Saturday farmers market, enjoy the restaurants and shops along Plant Street, hop on the West Orange Trail, or meet friends for dinner without ever getting in your car. Rare in character, remarkable in design, and irreplaceable in location, 480 W. Plant Street is more than a beautiful home. It’s an invitation to fall in love with where you live.

480 W Plant Street, Winter Garden
Winter Garden
$530,000
3 Beds ⋅ 4 Baths ⋅ O6453863 MLS
Welcome to modern Hamlin living in this beautiful END-UNIT townhome in highly desirable Winter Garden! Built in 2025 and offering 3 bedrooms, 3.5 bathrooms and over 2,000 square feet across three thoughtfully designed levels, this home combines the space and privacy of a single-family layout with the convenience of low-maintenance townhome living. One of the best features of this floor plan is that ALL THREE BEDROOMS ARE PRIVATE SUITES with their own bathrooms. The first-floor suite is ideal for guests, a home office, multigenerational living or anyone wanting additional separation and privacy. The second floor is the heart of the home, featuring a bright, open-concept kitchen, dining and living area with 42-inch cabinetry, white quartz countertops, stainless steel GE appliances and modern luxury vinyl plank flooring. Step outside to the covered lanai for an additional spot to relax or unwind. Upstairs, the spacious primary suite offers a private retreat along with the home's third bedroom suite. As an END UNIT, this home enjoys additional privacy with no neighbor on one side, plus added natural light. A two-car attached garage provides plenty of storage and everyday convenience, while the abundance of additional parking directly in front of the home makes hosting friends and family refreshingly easy. And then there's the LOCATION. Parkview at Hamlin puts you in the middle of one of Winter Garden's most convenient and sought-after areas, surrounded by restaurants, shopping, groceries, entertainment and everyday essentials. With SR 429 just minutes away, commuting throughout Central Florida is a breeze while still enjoying everything the Hamlin and Horizon West area has to offer. Modern, spacious, exceptionally well located and barely a year old—this is the kind of rental that truly feels like home. Schedule your showing and come see what makes this end-unit Hamlin townhome stand out.

Winter Garden
13846 Fresh Ivy Street, Winter Garden
$699,000
2 Beds ⋅ 3 Baths ⋅ O6453525 MLS
Beautifully appointed and thoughtfully designed, this home offers an exceptional opportunity to enjoy the Del Webb Oasis lifestyle—with the **seller covering the buyer's capital contribution fee PLUS six months of HOA dues!** From the moment you enter, you'll appreciate the attention to detail, sophisticated finishes, and inviting open-concept design. The beautifully appointed kitchen is a standout, featuring crisp white cabinetry, quartz countertops, stainless steel appliances, a gas cooktop, designer lighting, and an expansive center island with seating. The soft, coastal-inspired color palette, beautiful flooring, and thoughtfully selected finishes create a home that feels both elegant and comfortable. The kitchen flows effortlessly into the dining and living areas, making it equally suited for everyday living and entertaining. A dedicated private office or flex space offers additional versatility. Beyond the home itself, **Del Webb Oasis offers an exceptional 55+ lifestyle** with amenities designed for recreation, relaxation, and connection. At the heart of the community is a beautiful 12,000-square-foot clubhouse featuring an indoor/outdoor bar and tavern, coffee lounge, fitness center with Technogym equipment, yoga and movement studio, arts and crafts room, billiards, and gathering spaces. The on-site restaurant offers lunch and dinner on Wednesdays and Fridays, making it easy to meet friends and enjoy an evening out without leaving the neighborhood. Outdoors, residents enjoy a resort-style zero-entry pool with lap lanes, spa, poolside cabanas, pickleball and tennis courts, bocce ball, walking paths, and inviting social spaces. A full-time lifestyle director coordinates a vibrant calendar of neighborhood activities, clubs, fitness classes, trivia nights, social gatherings, and special events. Whether you want to stay active, explore new interests, or simply enjoy time with neighbors, there's always something happening. Ideally situated in Winter Garden, just minutes from Walt Disney World, shopping, dining, and major roadways, Del Webb Oasis offers the perfect combination of resort-style living and everyday convenience. **A beautifully finished home, an engaging community, and valuable seller-paid incentives—your next chapter starts here!**

13846 Fresh Ivy Street, Winter Garden
7183 Summerlake Groves Street, Winter Garden
$465,000
3 Beds ⋅ 3 Baths ⋅ O6450879 MLS
Located in the desirable Horizon West area of Winter Garden, this home features an open floor plan, neutral finishes, and a functional layout designed for comfortable everyday living. New landscaping enhances the home’s curb appeal, creating a fresh and inviting first impression. Inside, the open living spaces offer versatility for a variety of lifestyles, while newly carpeted bedrooms provide a comfortable retreat. Enjoy the Florida lifestyle with a covered lanai and fenced backyard, offering additional space to relax or entertain. Situated directly across the street from Orange County National Golf Center, this home offers a convenient location for golf enthusiasts and easy access to top-rated schools, Hamlin Town Center, shopping, dining, and Walt Disney World. Experience all that Winter Garden and Horizon West have to offer in this well-located home.

7183 Summerlake Groves Street, Winter Garden
234 Woodfall Lane, Winter Garden
$1,219,170
5 Beds ⋅ 5 Baths ⋅ O6453589 MLS
Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. The new two-story Roseland home combines modern elegance with practical living, offering 5 bedrooms, an enclosed flex room, 4 full bathrooms, a powder room, and a 3-car garage. As you step through the double entry glass doors, you are immediately greeted by a striking foyer that rises to the second floor, setting the tone for the entire home. To one side, a spare bedroom en suite offers privacy for guests and loved ones on the first floor, while the formal dining room invites effortless entertaining. From there, you enter the heart of the home—a chef-inspired gourmet kitchen. Equipped with built-in KitchenAid stainless steel appliances, including double ovens, the kitchen is a dream for culinary enthusiasts. Soft-close cabinetry with clear glass uppers is paired with exquisite quartz countertops, creating a timeless and sophisticated look, while a spacious walk-in pantry ensures ample storage. The open-concept design effortlessly connects the kitchen to the gathering room and cafe, where soaring ceilings create an airy, light-filled space, perfect for both intimate gatherings and larger celebrations. The covered lanai offers a seamless transition to the outdoors, ideal for year-round entertaining. Also located on the first floor, is a “Multi-Gen Suite” offering a spacious bedroom with its own linen closet, walk-in closet, and attached bathroom complete with a glass enclosed shower and quartz countertops. Upstairs, the private owner’s suite spans one side of the home, creating a peaceful retreat. The owner’s retreat area, ideal for reading or unwinding, leads into the spa-inspired owner’s bath, where luxury knows no bounds. A frameless glass-enclosed shower, free standing tub, enclosed toilet, and double walk-in closets create a sanctuary of relaxation. The second floor also offers two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring both privacy and convenience, while a third bedroom enjoys its own en suite bath, providing an added level of comfort and luxury. The upstairs laundry room, with a utility sink and a brand new Whirlpool washer and dryer makes daily tasks a breeze. With an intelligently designed layout and meticulously curated finishes, this home offers the perfect balance of form, function, and style. It's the epitome of luxury living in a highly sought-after location, blending convenience, sophistication, and thoughtful design into a living experience like no other. Schedule a tour today!

234 Woodfall Lane, Winter Garden
5567 Cypress Hill Road, Winter Garden
$519,995
3 Beds ⋅ 2 Baths ⋅ O6453267 MLS
Stunning 3-bedroom, 2-bathroom home located in the beautiful and desirable Orchard Hills subdivision of Winter Garden, FL. This home boasts a split bedroom plan, offering privacy and space, with carpeted bedrooms for added comfort. The master suite features a garden tub, perfect for unwinding after a long day. The open floor-plan is ideal for entertaining, with wood look tiled living areas and modern fixtures adding a touch of elegance. The kitchen is equipped with stainless steel appliances, ready for your culinary adventures. The interior has been freshly painted, giving the home a clean and bright feel. Step outside to a manicured lawn and a fence enclosed backyard, perfect for outdoor activities. Not to mention lawn service is included in the rent! The screen enclosed rear patio is a great spot for relaxation, while the front porch offers a scenic pond view, adding to the home's charm. The property also includes a large interior laundry room and a two-car garage for your convenience. As part of a vibrant community, you'll have access to a community pool, fitness center, and clubhouse. This home is not just a place to live, but a lifestyle to enjoy. Come and experience the comfort and convenience this home has for you.

5567 Cypress Hill Road, Winter Garden
15633 Panther Lake Drive, Winter Garden
$2,395,000
4 Beds ⋅ 5 Baths ⋅ O6453209 MLS
**Organic Modern Design. Intelligently Connected. Effortlessly Luxurious.** Discover extraordinary lakefront living in Winter Garden's Lakeshore Preserve community. Reimagined with nearly $1 million in renovations, this stunning residence blends sophisticated design, intelligent technology, and five-star resort-inspired living. Featured in *The Local Magazine's 2026 Home Issue*, the home showcases organic modern design with European and Mediterranean influences. Limewash walls, graceful archways, wide-plank flooring, custom millwork, and designer lighting create a warm, sophisticated atmosphere. A sculptural staircase with sweeping curved walls and a dramatic cascading chandelier makes an unforgettable statement. The beautifully appointed kitchen features custom cabinetry, premium JennAir appliances, a double-stacked quartz island, quartz backsplash, and beverage refrigeration. A walk-in pantry and drop zone add functionality. The primary suite offers a spa-inspired bath with a freestanding soaking tub, programmable shower, and custom California Closets. Additional highlights include a designer laundry room, upstairs entertainment loft, and equipped home gym with sauna. What truly sets this home apart is its seamless integration of technology. Control4 automation connects customizable Philips Hue lighting, Sonos audio, motorized shades, smart thermostats, security, and other features, making everyday luxury feel effortless. Outdoors, an infinity-edge pool with cascading waterfall overlooks Panther Lake. A two-level pool deck, covered entertaining areas, outdoor fireplace, integrated speakers, and motorized lanai screens create a private resort experience. Architectural lighting and a mosquito misting system add comfort and ambiance. Additional features include a whole-house generator, climate-controlled garages, EV charging, extensive security, and a professional smart-home technology transfer service for the new owner. Lakeshore Preserve offers included lawn care and a convenient location near Walt Disney World and SR 429

15633 Panther Lake Drive, Winter Garden
16549 Parable Way, Winter Garden
$545,000
4 Beds ⋅ 4 Baths ⋅ O6453528 MLS
Virtually Staged. 2023 build new house! Highly desirable Storey Grove community! NO CDD.Low HOA fee! Beautifully maintained 4-bedroom, 3.5-bath home in the highly desirable Storey Grove community! Featuring a thoughtfully designed floor plan with TWO Primary suites—one conveniently located on the FIRST floor and the other upstairs—this home offers exceptional flexibility for multi-generational living, extended family, or hosting guests. The functional and versatile layout provides comfortable living spaces ideal for both everyday living and entertaining. Enjoy the convenience of living in a family-friendly community with a community swimming pool and the added benefit of having elementary and middle schools right within the neighborhood—making daily school commutes easier for busy families. one of Storey Grove's most attractive features is its convenient location near Walt Disney World, offering easy access to world-famous theme parks, shopping, dining, and entertainment. With convenient access to major highways and everyday essentials, this home combines a desirable location with comfortable Florida living. Easy Access to Major Highways, Shopping, Dining, and Entertainment Don't miss this wonderful opportunity to enjoy comfort, flexibility, and convenience in the sought-after Storey Grove community, just minutes from the magic of Disney!

16549 Parable Way, Winter Garden
14501 Grove Resort Avenue Unit 3239, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ S5160379 MLS ⋅ Building 3 BLDG.
***Amazing opportunity to own a vacation condo at the beautiful Grove Resort and Water Park in Orlando! Ideal for SNOWBIRDS, you can stay in your unit up to 179 nights per year! Onsite rental management company rents out your unit on your behalf when you are not using it, yet when you stay you have full access to all the wonderful amenities at The Grove Resort! This 2-bedroom, 2-bathroom fully-furnished condo has a full kitchen, full washer and dryer, spacious living room with sleeper sofa, and screened-in balcony, with a pleasant view over the gardens. A short walk takes you to the Springs Pools area, with three heated pools, hot tub, the 24/7 gym, and the Valencia Restaurant. Just a few minutes stroll also takes you to the Surfari Water Park, with heated large pool and lazy river, water slides, splash area, the Flowrider surfing experience, and the Longboard Bar and Grill!! For further entertainment you have the 6000sf Flip Flops games arcade, with 9-hole mini-golf! A free shuttle goes daily to the Disney these parks, right outside the Marketplace convenience store and gift shop! Call now for more details!!***

14501 Grove Resort Avenue Unit 3239, Winter Garden
14503 Avenue Of The Rushes, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ O6450700 MLS
Pro Pics Coming Soon - 1st time on the market * Welcome to this beautiful and incredibly maintained home offering 4 bedrooms, 3.5 bathrooms, and approximately 3,315 square feet of living space in the desirable Signature Lakes community of Independence * Built in 2007, this spacious two-story home offers an inviting blend of comfort, style, and room to entertain * Attractive curb appeal, a welcoming covered entry, paver driveway, and tropical landscaping create a memorable first impression * Inside, the generous floor plan provides flexibility for everyday living, entertaining guests, and enjoying the Florida lifestyle * Step outside to the private screened pool area and create your own backyard retreat, perfect for relaxing and enjoying the sunshine year-round * Conveniently located near shopping, dining, major roadways, and the many amenities of Winter Garden, this property offers an excellent opportunity to enjoy the Central Florida lifestyle, with community recreation and outdoor activities. Community amenities include a clubhouse, 2 resort-style swimming pools, fitness facilities, tennis and basketball courts, playgrounds, parks, and community boat ramps and docks providing access to Lake Hancock.

14503 Avenue Of The Rushes, Winter Garden
13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ O6453203 MLS
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
14492 Sunbridge Circle, Winter Garden
$1,060,000
5 Beds ⋅ 4 Baths ⋅ S5160319 MLS
Welcome to the gated community of Bradford Creek in Winter Garden. This luxurious home has 5 bedrooms, 4 bathrooms and a 3-car garage. The kitchen features an over extended island, walk in pantry, 5-burner gas cooktop, top of the line appliances. Enjoy the oversized covered patio with friends and family. Great for entertaining. There are two ensuite bedrooms, one downstairs, and one upstairs, perfect for mother-in-law and/or guests. The downstairs ensuite is hidden behind a custom built secrete door with its private access to the backyard. The master bedroom is huge with 2 walk-in closets and a bathroom features dual rain shower heads. This home is top of the line with all modern accessories like Cat 6 Ethernet, tankless gas water heater, ring camera at front door and smart lights and much more. Come see for yourself.

14492 Sunbridge Circle, Winter Garden
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