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$550,000
Bray J W F Add 01 SubDv. 34787 Zip Code
Prime Vacant Land in the Heart of Downtown Winter Garden. Rare opportunity to own a 16,338 sq. ft. vacant lot perfect to build a custom home, two single family homes or a duplex. in the picturesque downtown Winter Garden area. Just a short walk to Plant Street, this property is ideally situated near the vibrant heart of the city, offering unmatched convenience and charm. This spacious lot provides endless possibilities in one of Central Florida’s most sought-after communities. Downtown Winter Garden is known for its welcoming atmosphere, featuring award-winning restaurants, boutique shops, theaters, local events, and a lively cultural scene. Enjoy walkability, historic character, and modern amenities all in one location. Whether you envision a private residence or an investment opportunity, this property offers an exceptional chance to build in a thriving area.

47 Oak Street, Winter Garden

$515,000
3 Beds 3 Baths Waterleigh Ph 2a SubDv. 34787 Zip Code
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence with a bonus room/office, built in 2018 and thoughtfully designed for both comfort and functionality. From the moment you step inside, you’ll appreciate the open-concept layout and high ceilings that create a light, airy feel—perfect for hosting gatherings or enjoying quiet evenings at home. This move-in-ready home features brand-new carpet throughout the upstairs and all bedrooms, along with fresh interior paint (December 2025) and new exterior paint (May 2025), giving it a clean, modern feel throughout. Upstairs, all three bedrooms and two full bathrooms give you a private retreat, highlighted by a spacious primary suite with a walk-in closet featuring custom built-ins designed to keep everything organized and within reach. Enjoy Florida living year-round on the covered outdoor patio, ideal for morning coffee or winding down at the end of the day. A separate laundry room adds everyday convenience, while HOA-maintained landscaping allows you to spend more time enjoying your home and less time on upkeep. Located in a vibrant community offering parks, a resort-style pool, and clubhouse, this home combines lifestyle, comfort, and convenience in one exceptional package. Don’t miss your chance to make this inviting Winter Garden home your own.

16330 Brisk Breeze Alley, Winter Garden

$640,000
4 Beds 3 Baths Black Lake Preserve SubDv. 34787 Zip Code
WINTER GARDEN most desirable gated community of the Black Lake Preserve with the playground, walking trails ... in a small, friendly community with just 92 homes. Unbeatable location, walking to school, just minutes to Historic Downtown Winter Garden’s shops, dining, parks, with easy access to Florida’s Turnpike, FL-429, and SR 408, walking to the SunRidge Elementary and Middle Schools. Downtown Orlando and world-famous theme parks. Built in 2016 with an open floor plan. A formal living/office space on the right and a dining room on the left after entering through the front door. The open kitchen with granite countertops and beautiful backsplash, stainless steel appliances including a gas cooktop, upgraded 48” stylish cabinets, and a spacious walk-in pantry. The open floor plan offers plenty of space for your family room. The master suite with great natural lighting, an extra-large walk-in closet, double sinks, and a garden tub with a separate step-in shower. The 3 additional bedrooms are on the other side of the home, along with a full bathroom plus a guest bathroom in front of the house and a spacious laundry room. Call the listing agent to schedule a tour and start making memories in your new HOME SWEET HOME!

14517 Black Lake Preserve Street, Winter Garden

$555,000
4 Beds 4 Baths Waterleigh Ph 4b & 4c SubDv. 34787 Zip Code
Welcome to this stunning Clearden model, offering 4 bedrooms and 3.5 bathrooms in one of Horizon West’s most desirable neighborhoods — Waterleigh! The thoughtful floor plan features a spacious primary suite upstairs, along with two guest bedrooms and a versatile loft area, perfect for a home office or playroom. Downstairs, you’ll find a guest suite with a private bath, ideal for visitors or multigenerational living. The modern kitchen boasts stainless steel appliances, granite countertops, and opens to a large family room, creating the perfect space for entertaining. The primary bathroom includes dual vanities with granite tops and a large walk-in closet. This home also includes the Smart Home Package, offering convenience and peace of mind with the latest in home automation technology. Located in the resort-style Waterleigh community, residents enjoy exceptional amenities including two beautiful clubhouses, two resort-style pools, two fitness centers, mini golf, tennis courts, beach volleyball, dog park, and scenic lakefront picnic areas with BBQs. Experience the perfect blend of comfort, style, and Florida lifestyle living at its best — schedule your private showing today!

17098 Water Spring Boulevard, Winter Garden

$715,000
4 Beds 4 Baths Encore At Ovation-Ph 3 SubDv. 34787 Zip Code
***Lease agreement in place until March 2027*** This beautifully furnished single-family home offers a luxurious living experience with 4 bedrooms and 3.5 bathrooms, meticulously built in 2022. The property boasts a 2-car garage and a spacious loft, ideal for versatile uses. The kitchen is adorned with top-of-the-line stainless steel appliances, while the windows are elegantly adorned with stylish treatments. The master bedroom is a sanctuary with dual walk-in closets providing ample storage space. The laundry room is both practical and stylish, featuring a sink and modern washer and dryer for added convenience. Nestled in a vibrant new community, residents can indulge in a range of amenities including a clubhouse, pool, and a dog park. The property's prime location offers easy access to Disney World and major highways, ensuring seamless travel experiences. Whether as a lucrative long-term investment or a cherished primary residence, this listing promises a contemporary and comfortable living environment with sought-after features and an enviable location.

13706 Werrington Drive, Winter Garden

$1,499,999
4 Beds 3 Baths J L Dillard Sub 3 SubDv. 34787 Zip Code
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

241 N Dillard Street, Winter Garden

$298,000
3 Beds 2 Baths Southern Pines Condo SubDv. 34787 Zip Code
Welcome to this amazing unit, nestled within the gated community of Southern Pines in the sought after area of Winter Garden , Florida; this beautiful 3 bedrooms 2 bathrooms condo is located in the second floor and has an open concept kitchen with a Dinning- living combo area, also an additional space for an office or a play area , the unit also has a split bedroom plan , with a spacious primary bedroom and an ensuite, also two additional bedroom at the other side of the unit, with an additional full bathroom . This incredible community has a so much in amenities; a real lifestyle for the residents , such as community pool and spa , a very well equipped fitness center, a club house with many areas for family entertainment, tennis court, playground, a car wash area and an indoor basketball / racquetball court. This condominium is located a short drive from the Winter Garden Village shopping area , as well as Downtown Winter garden, with easy access to all main Highways making the commute easier. The Disney World parks are just 9 miles away; this community is definitely a place where families will experience great enjoyment; don't miss the chance to call this unit your NEW HOME!!

330 Southern Pecan Circle Unit 208, Winter Garden

$119,000
Mary Jean Sub SubDv. 34787 Zip Code
Build your dream home or investment property! Owner is willing to turn over the plans for a single family home for you to start the project right away and potentially saving you thousands. Quiet street with lots of mature oak trees and new construction in the area. 5 min from the iconic downtown Winter Garden, 3 minutes away from gorgeous Lake Apopka, and less than a mile from the 429. You will enjoy super convenient access to SR 429, SR 50, Florida's Turnpike, and the SR 408. Disney, Universal, downtown Orlando, and the Orlando Eye are easy drives. The neighborhood is not part of an HOA, so no annual association fees are due. Public Water/Sewer/Electric connections are available. Don't miss this opportunity. Make an offer now!

188 Mary Street, Winter Garden

$999,000
4 Beds 4 Baths Northlake/Ovation Ph 1 SubDv. 34787 Zip Code
Welcome to this stunning brand-new single-story home, perfectly located in the sought-after Horizon West community in Winter Garden. This 4-bedroom, 3-bath residence with a 2-car garage combines modern design, energy efficiency, and a lifestyle of comfort and elegance. Step inside and be amazed by the bright open-concept floorplan, highlighted by natural light and a fresh, modern color palette. The chef’s kitchen is a true showstopper with 42-inch shaker cabinets in light tones, gorgeous quartz countertops, a large island ideal for gatherings, and premium stainless steel appliances—including refrigerator, range, dishwasher, microwave, washer, and dryer. The home’s efficient construction ensures comfort and savings, while the spacious lanai invites you to relax and enjoy serene views of the Star Lake and lush conservation area—your private piece of paradise, right in your backyard. Opportunities like this don’t last long in Horizon West! Don’t miss your chance to own this extraordinary single-story lakeside retreat. Schedule your private showing today and make this dream home yours!

17552 Lake Star Road, Winter Garden

$869,990
5 Beds 4 Baths Tilden Place/Winter Garden SubDv. 34787 Zip Code
Beautifully upgraded home located in the desirable gated community of Tilden Place in the heart of Horizon West. This home showcases one of the builder’s highest-level design upgrade packages, featuring premium cabinetry, upgraded flooring, elegant finishes, crown molding, designer lighting, and a gourmet kitchen with luxury selections throughout. The fully fenced backyard provides privacy and is perfect for entertaining, pets, or outdoor living. Outstanding location just minutes from Hamlin Town Center, offering convenient access to shopping, dining, entertainment, Cinepolis Luxury Cinemas, Publix, Walgreens, and major roadways including SR-429. Nearby restaurants include The French Cafe, Bosphorous Turkish Cuisine, Agave Azul Cocina Mexicana, Ford’s Garage, Gochujang Korean BBQ, Capone’s Coal Fired Pizza, Teak Neighborhood Grill, Jeremiah’s Italian Ice, Kelly’s Homemade Ice Cream, Starbucks, and Home State Brewing Co. Zoned for highly sought-after schools:Keenes Crossing Elementary School, Bridgewater Middle School, Windermere High School, Foundation Academy – Tilden Campus; The Goddard School of Winter Garden, Cranium Academy, StarChild Academy of Winter Garden. Easy access to Walt Disney World, Flamingo Crossings, Winter Garden Village, Orlando Health Horizon West Hospital, and the future Horizon West growth corridor. Don’t miss this exceptional opportunity to own one of Horizon West’s finest homes in a gated community with premium builder upgrades. Schedule your private tour today and experience everything this beautiful home.

14327 Wabasso Loop, Winter Garden

$799,900
Acreage & Unrec SubDv. 34787 Zip Code
Serene 5 acre property! Zoned for residential and agricultural use. Whether you envision building your dream home, farming or simply enjoying the peaceful landscape, this land offers country living without sacrificing city amenities. For those looking for a turnkey solution, the property is also available as a to-be-built custom home opportunity with Lionshead Homes, allowing buyers to design and build a luxury residence tailored to their lifestyle. Conveniently located just 7 minutes to Publix at Hamlin or Publix at Stoneybrook. Shopping, dining, medical offices, hospitals, movie theater are all close by! Disney World 20 minutes. Orlando International Airport 35 min. Contact us for additional information and take the first step towards owning your slice of rural paradise!

9940 Black Bear Lane, Winter Garden

$989,000
4 Beds 4 Baths Summerlake Reserve SubDv. 34787 Zip Code
We present an impeccable, newly built home in brand-new condition, ready to welcome you and your family with comfort, modernity, and style. Located in the sought-after Summerlake Reserve community in Horizon West, this home surprises with every detail. Upon arrival, the charming porch with its well-kept garden gives you a taste of what lies ahead. Upon entering, the integrated living, dining, and kitchen areas create a feeling of spaciousness and warmth, perfect for those who value open, well-lit spaces. Large sliding doors allow for abundant natural light and connect the interior with the exterior. With high ceilings of almost 3 meters, the home exudes elegance and sophistication. The kitchen is a true highlight: equipped with modern appliances, high-end wood cabinetry, a large central island, and a spacious pantry—ideal for those who love cooking and entertaining. The four bedrooms are spacious, well-appointed, and designed to offer maximum comfort. There are three and a half bathrooms, all with quality finishes and tasteful furnishings. The laundry room offers a functional space and is already equipped to make daily life easier. The garage accommodates three cars and has an automatic gate, ensuring convenience and security. All this in a prime location, close to schools, shops, restaurants, and all the amenities that make Horizon West one of the most valued areas in Florida. If you're looking for a new, modern home in a complete community, this is the perfect opportunity. Schedule your visit and come see for yourself!

9493 Emerald Berry Drive, Winter Garden

$2,700,000
Lake Avalon Groves Rep SubDv. 34787 Zip Code
Probably the finest site for a huge estate home in Orange County! No need to move almost an hour away to Montverde just to find enough land to build your private estate or Equestrian estate when this gem is minutes to Windermere and everywhere you want to be. This highly sought after 10 acre property in the Lake Avalon rural settlement, is a declining citrus grove and sits on the highest elevation in West Orange County, which affords it incredible views in every direction. If you build a two story home on the property with a balcony situated just right, you can see all the way to Orlando, Windermere, and the nightly Walt Disney World fireworks. There is a contract in place for reclaimed water for irrigation and a clean well on the property for drinking water. This dream property is just minutes from the thriving downtown Winter Garden Village, Hamlin center, downtown Windermere and minutes to the 429 expressway to downtown Orlando, Disney, and all major shopping , dining, and attractions. This lot is a rare find! There is nothing like it on the market, and there never will be again, as quality parcels of country real estate are disappearing. Don't miss your chance to own your dream piece of country paradise!

17902 Seidner Road, Winter Garden

$2,500,000
34787 Zip Code
Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with approximately 844 linear feet of lakefront property on Lake Roper. Home could also be rebuilt as a multigen and could be larger if needed with ample room for multiple garage spaces as well (example of possible home and floor plan attached in photos). This is a RARE OPPORTUNITY to acquire this much lakefront property and land but be in close proximity to city center, major thoroughfares, restaurants, theme parks, international airports. Example photos of possible home and floor plan provided by custom home builder, David Konkol Custom Homes.

13377 Lake Butler Boulevard, Winter Garden

$635,000
4 Beds 3 Baths Silverleaf Reserve At Hamlin SubDv. 34787 Zip Code
JUST REDUCED - SELLER MOTIVATED! Step right into the highly sought-after Winter Garden lifestyle with this beautiful 4-bedroom, 3-bathroom home in the premier Silverleaf Reserve community. Designed to impress, the expansive open floor plan boasts soaring high ceilings and an abundance of natural light, creating a seamless flow for entertaining and daily living. The modern kitchen is equipped with sleek stainless steel appliances and opens directly into the spacious main living areas. Retreat to your primary suite, a true sanctuary featuring a massive walk-in closet and a luxurious spa-like bathroom designed for ultimate relaxation. Outside, enjoy the beautiful Florida weather year-round on your covered lanai, which overlooks a private, landscaped backyard. Location is everything, and this property delivers unparalleled convenience—you are just a few blocks away from highly rated Hamlin Elementary and Middle Schools, the vibrant dining, shopping, and entertainment at Hamlin Town Center, and major highways for a quick, stress-free commute throughout the Orlando area. This home offers the perfect blend of modern comfort, space, and prime accessibility. Turnkey properties in this neighborhood are in high demand and move fast. Call today to schedule your private showing before this exceptional opportunity is gone!

16271 Silver Grove Blvd, Winter Garden

$2,999,000
Fries Winter Garden SubDv. 34787 Zip Code
COMMERCIAL property in downtown WINTER GARDEN! Located directly on PLANT STREET in the Historic District Overlay this property offers great exposure. It is currently zoned C-1 and has many permitted uses such as retail establishments, eating and drinking establishments, office & studios, financial institutions, private club, personal service, church and more. Permitted use list available upon request. Total property consist of over 3300 square feet and almost 2700 square feet of interior space. Property is split up unit two units. The first unit is approximately 1050 interior space offering a main retail area measuring 25x22, an office 9x14 and additional room 18x8. There is additional walkway space and two restrooms. The second unit is approximately 2050 interior space offering a 31x14 retail space, and additional spaces measuring 6x14, 8x12,10x17,18x24 and 7x15. There is additional walkway space and one restroom plus rear entrance/exit ability. ENJOY the downtown Winter Garden life.

18 & 20 E Plant Street, Winter Garden

$160,000
. SubDv. 34787 Zip Code
Business for Sale Only - Exceptional opportunity to own a well-established beauty Salon in the heart of Winter Garden. Great Located. This Beauty Salon offers unbeatable visibility and foot traffic, making it a high-demand business with strong revenue potential. Key Features: Turnkey Operation: Fully equipped with modern chairs, mirrors, workstations, and a reception area. High-traffic, constant flow of customers. Established Clientele: has built a solid reputation and loyal customer base. This business is perfect for an owner-operator or an investor looking to step into a thriving market with significant foot traffic. With its prime location and steady clientele, this is poised for continued growth. Call to set an appointment.

120 S Dillard Street, Winter Garden

$2,550,000
4 Beds 5 Baths Lake Avalon Groves Rep SubDv. 34787 Zip Code
Pre-Construction. To be built. 4633 sq ft of living space, set on a sprawling 2.5 acre lot. Choose from this 4 Bedroom, 4.5 Bathroom, 4 Car Garage Custom Home or Lionshead Homes will design an alternative floor plan just for you! The property exudes tranquility with its lush mature landscape, offering ample room for a pool, outdoor activities, gardening, or farm animals. Inside, the home features a modern layout with luxurious finishes, a spacious kitchen, formal and informal dining, office, game room and a lavish Master Suite which features double tray ceilings, his and her closests, large shower and a freestanding tub. Outside, the large lot provides privacy and a peaceful escape, while still being conveniently close to Winter Garden’s vibrant amenities, including shopping, dining and top-rated schools. Ideal for Homeowners seeking a rural escape without compromising accessibility. Alternative floor plans for this homesite are available upon request.

17144 Phil C Peters Road, Winter Garden

$975,000
Lake Avalon Groves Rep SubDv. 34787 Zip Code
Cleared and ready for your dream home! Welcome to 17144 Phil C Peters Road, a serene retreat nestled in Winter Garden, where country charm meets modern convenience. The large 2.5 acre property is high and dry with direct frontage on Phil C Peters Rd. The front of the property is dotted with a mature oaks, canopy and the middle and rear of the property is mostly open and flat providing plenty of space for a new custom home and potential barn, garage, garden, etc. Farm animals are welcome! This property is perfect for those craving space and tranquility while staying connected to city conveniences. Located just 5 minutes from shopping and dining in Hamlin and Stoneybrook West. Close proximity to top rated public and private schools. Property comes with impact fee credits and a newer well already onsite. Listing Broker is the owner of Lionshead Homes. Lionshead Homes will design and build your new custom dream home, if desired. Floor Plans available upon request.

17144 Phil C Peters Road, Winter Garden

$585,000
4 Beds 3 Baths Arrowhead Lakes SubDv. 34787 Zip Code
WATERFRONT--2 ACRES--NO HOA 7 Miles west of Disneys' main entrance...Winter Garden address with "A rated" schools listed on tax records. Close to many restaurants, shopping and other amenities. This is considered the 4 Corner Area because across Hwy 192 is Kissimmee, Hwy 27 is just a couple blocks west and if you go North it is Clermont and going south on Hwy 27 is Davenport. Piece of Paradise..Spacious..Upgraded...MOVE IN READY.. Expansive 2 car garage..workshop...storage...oversized.. Also approx 19X11 shed with an upper loft area ..The property is partially fenced. --..French doors open to a deck overlooks Lake Chapin in the rear of the property with fruit trees, banana trees, .. You will absolutely need to see to appreciate this home...even driving by, it is deceivingly large from just outside appearance.(almost 3400 Living sq ft). Beautifully maintained and Quality throughout.--Double Paned, tilt-out Windows with Marble sills--Well Maintained Bamboo Flooring (quality thicker boards ).Loads of Storage throughout and lighted closets...extra insulation in attic..Ceiling fans with wall controls and remotes..-French doors..-the list continues... A Central Kitchen that will delight the Chef --It has been thought out from past years of wants and needs and implemented. A WALL of Cabinetry..Corner Lazy susans upper and lower , pull out drawers ..under counter lights ..Convection oven and island cooktop with grill. Bar area opening into the Living room/ Dining room.. Split bedrooms plan and Master Suite has an extra room adjoining,which could be a exercise room, office, sitting room just to name a few. Large (approx 16x15) Suite has 3 solid core barn doors to close off the double walk in closet ROOMs and for the entrance door. Beautifully done Master Bath. (approx 13x9) Inside Laundry room with additional outlet for another refrigerator ..freezer. More than expansive (approx 16x13 sq ft) with a prestine pool table that can stay or go...your call.. This home makes a fantastic home for entertaining and/or family life with room to grow .. Come and see this home and you will want to make it yours..There is not another like it around. and it's so rare to find

14902 Arrena Road, Winter Garden

$1,250,000
Avalon Hills Sub SubDv. 34787 Zip Code
Discover 5.1 beautiful acres in Avalon Hills, an exclusive community featuring just 16 premium luxury home 5 acre lots. No need to move almost an hour away just to find some land and more privacy when this gem is minutes to Windermere and everywhere you want to be. This vacant land represents the essence of premium real estate, nestled at the end of a one-way street ending in a serene cul-de-sac bordered by State conservation land that will never be developed. Imagine crafting your dream home on the premier lot, perched on a gentle hill overlooking the entire neighborhood. The elevation advantage allows for breathtaking sunset views that you can relish right from your front door. Numerous mature oak trees throughout the property offer splendid options for integrating them into your home's design. While maintaining the tranquil country atmosphere, you'll still enjoy all the advantages of a Winter Garden zip code while paying Lake County taxes and still be minutes to Windermere and surrounding areas. Nearby luxury estates ensure your new home will fit seamlessly into this elegant neighborhood. It gets better, you will have the freedom to choose any builder you prefer. Minutes to Windermere, Hamlin, Winter Garden Village, and the 429 Expressway to Disney, Downtown Orlando, and all major shopping, restaurants, and attractions. This lot is truly a rare find, as there's nothing quite like it currently on the market. Don't miss this chance to own your piece of paradise! all measurements and zoning restrictions to be verified by the buyer/ buyers agent.

10133 Colt Lane, Winter Garden