Explore Winter Garden, FL Homes for Sale Between $1,000,000 to $1,250,000

Homes for Sale in Winter Garden, FL Between $1,000,000 to $1,250,000

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Welcome to your dedicated resource for Homes for Sale Between $1,000,000 to $1,250,000 in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $1,000,000 to $1,250,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Winter Garden, FL Homes for Sale Between $1,000,000 to $1,250,000

4 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.

64 N Park Avenue, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Watermark Ph 2a SubDv. ⋅ 34787 Zip Code

Located in the highly sought-after Watermark community in Winter Garden, this stunning 4-bedroom, 3 full bath, and 1 half bath home offers the perfect blend of luxury, comfort, and functionality. Step inside to find beautiful wood flooring, tile, and plush carpet thoughtfully placed throughout the home. The chef-inspired kitchen features gourmet stainless-steel appliances, ample cabinetry, and modern finishes—ideal for both everyday living and entertaining. Elegant details elevate the interior, including crown molding, upgraded baseboards throughout, and a tray ceiling in the spacious primary suite. The home also offers a versatile bonus room perfect for a media room, office, or playroom. The laundry room is equipped with built-in cabinets for added storage and convenience. A 2-car garage completes the home, while the community offers exceptional amenities and a prime location close to shopping, dining, and major roadways. Schedule your private showing today and experience the best of Winter Garden living!

9312 Holliston Creek Place, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code

WELCOME TO A TRULY EXCEPTIONAL HOME in the highly sought-after community of Lakeshore Preserve in Winter Garden, where luxury, comfort, and lifestyle come together seamlessly. This beautifully upgraded Toll Brothers Madeira floor plan offers 5 bedrooms, 4.5 bathrooms, and a 3-car tandem garage, and feels practically brand new, having been gently lived in by only a couple. This home features a private lot and a tranquil backyard, offering the peace and privacy many buyers desire while still enjoying all the benefits and conveniences of a vibrant community. From the moment you enter, the barrel ceiling foyer and soaring 10-foot ceilings create a grand yet inviting first impression. Natural light fills the open layout, drawing you into the heart of the home, a stunning gourmet kitchen designed for both everyday living and entertaining. Enjoy upgraded cabinetry, designer hardware and faucets, pull-out drawers, a wood plank backsplash accent wall, a spacious center island with breakfast bar, and a butler’s pantry for added functionality and elegance. The kitchen flows seamlessly into the family room, highlighted by a tray ceiling and pocket sliders that open to your private outdoor oasis. The extended screened lanai overlooks a gorgeous custom pool featuring a waterfall, LED illumination, and fully automated smart controls accessible from your phone, true resort-style living at home. The patio is pre-plumbed for an outdoor kitchen with water hookups, and the outdoor space is elevated with Shell Beach Tumbled Versailles Pattern pavers, a fully fenced yard, landscape lighting, a retaining wall, and an additional 10x10 paver patio for even more entertaining space. Downstairs, guests will appreciate a private bedroom and full bath, plus an additional half bath for convenience. Home theater speakers are pre-wired on both the first and second floors, adding built-in entertainment value. Upstairs, a spacious loft anchors the remaining bedrooms, creating the perfect second living area. The owner’s suite is a true retreat featuring dual vanities, a soaking tub, a glass-enclosed walk-in shower, and a custom built-in closet. Additional bedrooms include a Jack-and-Jill setup, a private en-suite, and a flexible room ideal for an office, gym, or craft space. Laundry is conveniently located upstairs. Bonus Magic: Enjoy nightly views of the Magic Kingdom fireworks right from your home. Families will appreciate the proximity to highly rated, A-rated schools, providing excellent educational opportunities just minutes away. Living in Lakeshore Preserve means access to resort-style amenities including a lakefront clubhouse, pool, fitness center, playgrounds, dog park, sand volleyball, canoeing, and community events: all in the heart of the Hamlin area, close to top shopping, dining, major highways, and everyday conveniences. This isn’t just a home: it’s a lifestyle!

15625 Sylvester Palm Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

Discover refined living in this impressive 5-bedroom, 4-bathroom Spanish-style estate home, beautifully positioned on a serene waterfront lot with peaceful conservation views and nightly Disney fireworks from your own backyard. This exceptional home blends elegance, comfort, and energy efficiency throughout its thoughtfully designed layout. Step through the grand, elegant entrance into a soaring cathedral-ceiling foyer that leads to spacious formal and casual gathering areas. The formal dining room sets the tone for entertaining, while the gourmet kitchen is a true showpiece—featuring an oversized island, dry bar, walk-in pantry, solid wood cabinets, granite countertops, elegant backsplash, and high-end stainless steel appliances. A striking stone accent wall with an electric fireplace adds warmth and style to the main living area, which opens through French doors to breathtaking water and conservation views. The first floor includes a comfortable guest bedroom with a walk-in closet, a full guest bath with convenient pool access, and a luxurious primary suite. The primary bedroom offers a huge walk-in closet, and a spa-inspired ensuite bathroom with garden tub, expansive walk-in shower with multiple rain shower heads, and dual vanities. Upstairs, a spacious loft with surround sound showcases elevated views of the water and conservation area—perfect for a media room or game space. On one side of the loft sits a private bedroom with its own full bath, ideal for guests or extended family. On the opposite side are two additional bedrooms connected by a Jack-and-Jill bathroom, providing comfort and privacy for everyone. Additional highlights include a tile roof, oversized garage, paver driveway, Smart thermostat, water softener and filtration system, and energy-efficient features for year-round comfort. Located in the highly desirable Watermark community, residents enjoy resort-style amenities including a sparkling pool, water park, cabanas, BBQ areas, playground, dog park, tennis and basketball courts, clubhouse with rooftop deck, weekly community activities, fitness center, and scenic walking trails. All of this—just minutes from top-rated schools, dining, shopping, Orange County National Golf Course, and Disney World. A perfect blend of elegance, comfort, and unmatched location—this waterfront estate is truly a must-see.

9207 Busaco Park Way, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code

PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.

205 Surprise Drive, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code

Seller Motivated , Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative glass cabinetry, ideal for both everyday living and entertaining. The gorgeous master suite includes a custom built-in walk-in closet, providing both style and functionality. With 6BR/5BA, there’s plenty of space for family and guests alike. Enjoy Florida living at its finest in your outdoor oasis, complete with a gazebo and a built-in fire pit seating area, perfect for relaxing evenings or weekend gatherings. The three-car split garage adds convenience and ample storage.Recently renovated and freshly painted, this home is truly move-in ready. Located in a wonderful community offering two sparkling pools and a playground, you’ll love the nearby amenities that make Winter Garden such a special place to live. Tour Today!

10067 Austrina Oak Loop, Winter Garden

Overstreet Crate SubDv. ⋅ 34787 Zip Code

VERY RARE FIND . EXCELLENT LOCATION IN WINTER GARDEN . CLOSE TO HWY 50 ON 9TH STREET . SITE APPROVED FOR 5400 SQ FOOT BLD MANY USES . COMES WITH BUILDING PLANS AS WELL , READY TO BUILD . GROUND LEASE OPTION IS ALSO AVAIABLE .

851 9th Street, Winter Garden

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

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