Homes for Sale Near Windy Hill Middle in Winter Garden - 8 homes

Remarks: Five bedrooms, four and a half baths, and a three-car split garage inside a gated waterfront community on Johns Lake. This 2020-built home in Lakeview Preserve is built around space and flexibility. The kitchen anchors the main living area with stainless appliances, a large center island, and an open sightline into the family room and dining space. A downstairs primary suite sits privately off the family room with a spacious walk-in closet and an oversized ensuite bath. On the opposite end of the first floor, a guest bedroom with its own private ensuite makes the layout ideal for multigenerational living or overnight guests. The true split floor plan keeps everyone's space their own. Upstairs holds three more bedrooms, including a second primary with a walk-in closet and private ensuite bath. The remaining two bedrooms share a guest bathroom. Lakeview Preserve is a gated community on Johns Lake with a resort-style pool, fitness center, cabana, playground, splash pad, and a private community dock with a kayak launch. Conservation areas run throughout the neighborhood. You're minutes from Hamlin Town Center, the 429, AdventHealth Horizon West, and Stoneybrook West Village, with Historic Downtown Winter Garden and the West Orange Trail about eight miles away. Disney is a fifteen-minute drive. Rare to find this much square footage, this many ensuites, and gated lake access all in one address.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Brad Young (407-897-5400)

Remarks: Searching for a 4-bedroom home in Winter Garden with lake views, a private office, and a 3 car garage in a gated community? Welcome to 3439 Buoy Circle, a well maintained single family residence offering approximately 2,900 square feet, 4 bedrooms, a dedicated office, and 4.5 bathrooms, thoughtfully positioned to capture peaceful water views and stunning evening sunsets. Built by Taylor Morrison, this coveted Saint Croix floor plan features a well designed layout that blends comfort, privacy, and everyday functionality. Located within the gated Lakeside Preserve community on Johns Lake, this home offers a quiet residential setting with a scenic entrance that creates a sense of separation from major traffic corridors while remaining conveniently connected to daily essentials. The flexible floor plan supports modern living and includes a private office, ideal for working from home or creating a focused, dedicated space. Each bedroom features its own private full bathroom, along with an additional half bath for guests. The primary suite, bathroom, and walk-in closet span the full length of one side of the home, creating a spacious and well designed retreat with generous storage. The walk-in closet connects directly to the laundry room, adding ease and efficiency to daily routines. A standout feature is the 3 car garage, offering valuable space for vehicles, storage, recreational equipment, or hobbies. The homesite provides added privacy with only one immediate side neighbor, while the backyard is positioned to enjoy lake views and west-facing sunset exposure, creating a peaceful outdoor setting for relaxing or entertaining. Lakeside Preserve is a gated waterfront community featuring resort-style amenities, including a fitness center, pool, cabana, playground, and splash pad, along with direct access to Johns Lake with a kayak launch and dock. Natural conservation areas are thoughtfully woven throughout the neighborhood, enhancing both privacy and the overall setting. Residents enjoy close proximity to Hamlin Town Center, FL 429, AdventHealth Horizon West Hospital, Historic Downtown Winter Garden, the West Orange Trail, and the attractions of Walt Disney World, all within a short drive. This 4-bedroom home in Winter Garden offers a rare combination of lake views, ensuite bathrooms in every bedroom, a private office, and a 3 car garage within a gated waterfront community, delivering both everyday comfort and long term value in one of Central Florida’s most desirable areas. Information deemed reliable but not guaranteed. Buyer and buyer’s agent to verify all measurements, HOA information, school zoning, and property details..

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Patricia Solivan Lopez (407-218-2477)

Remarks: One or more photo(s) has been virtually staged. Welcome to 3276 Sailing Pier Ave. This beautifully maintained 3 bedroom, 2 bathroom residence also features a spacious office that can easily serve as a fourth bedroom, making it perfect for growing families, remote work, or hosting guests. Inside, you will find 9 foot ceilings that enhance the open, airy feel of the home, along with upgraded luxury vinyl plank flooring that adds both elegance and durability throughout the main living areas. The garage has been upgraded with durable epoxy flooring, providing a clean, polished look while also offering easy maintenance and long-lasting performance. The heart of the home is the stunning, light filled kitchen, designed with both functionality and style in mind, ideal for everyday living and entertaining. The oversized primary bedroom offers a relaxing retreat with ample space to unwind. Outside enjoy Florida living at its finest with a retractable screened in lanai, giving you the flexibility to enjoy fresh air or enclosed comfort year round. Located within a secure gated community, residents enjoy access to resort style amenities including a pool, playground, tennis courts, and a clubhouse, perfect for an active and social lifestyle. This home is ideally situated near the charm of downtown Winter Garden, where you can explore local shops, dining, and the popular Plant Street Market. Outdoor enthusiasts will love the nearby West Orange Trail, while convenient access to major roadways makes commuting to Orlando, theme parks, and surrounding areas quick and easy. Shopping, dining, and entertainment options are all just minutes away, making this location as practical as it is desirable.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Under contract-accepting backup offers. If you've ever dreamed of country living, but don't want to give up your conveniences, then welcome to your DREAM property in desirable Winter Garden! This spacious 2,571 sq ft custom home sits on 4.6 acres and includes a 3 stall horse barn with a tack room, as well as an additional 10x20 garage. The home has so much natural light and views out of every window. The kitchen has been recently updated and it's a showstopper! Relax in the sparkling pool and enormous outdoor entertainment space. Property like this is a rare find! Avalon Estates is located close to several shops and restaurants, the Florida turnpike, 429 and 408 expressways, 11 miles from Disney World, 12 miles from Universal Studios, and is an easy 23 miles from Orlando International Airport. Reserve a private viewing of this exceptional country home and begin building memories today. Pool built in 2023 with a state-of-the-art heating and cooling system.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Brad Bolton, Llc (407-797-8875)

Remarks: Welcome to the Lakeview Community! This stunning single-family residence features 5 spacious bedrooms, 4 full bathrooms, and a convenient half bath. The open-concept kitchen and living area, equipped with stainless steel appliances and modern touches, seamlessly connect to the backyard through full retractable sliding doors. The first floor includes a comfortable mother-in-law suite with a private bathroom and a versatile flex room for added convenience. Upstairs, you'll find 4 additional bedrooms, a laundry room, and a spacious great room perfect for family time or relaxation. Outside, enjoy a comfortable and contemporary gazebo, ideal for entertaining or unwinding. This home also showcases a modern lamp set and an advanced lighting system, adding elegance and ambiance to every corner. With its thoughtful design, enlarged kitchen, and modern light switches, this fantastic floorplan has everything your family needs!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Franklin Adrianza (786-241-2060)

Remarks: Encompassing five pristine acres, this exceptional compound offers a rare blend of privacy, craftsmanship, and refined outdoor living. Framed by mature oaks and approached by a picturesque, tree-lined drive, the property unfolds as a secluded retreat designed for casual entertaining and boundless enjoyment of serious hobbies and collections. At the heart is a 3,041-square-foot farmhouse rich in warmth and architectural character, offering 3 bedrooms, 2.5 bathrooms, a flex room, and a second-floor bonus space. Thoughtfully designed for function and lifestyle, the estate is further enhanced by a detached lakeside retreat—featuring a 4-car garage with 13-foot doors, multiple vehicle lifts, epoxy floors, and an integrated compressor system. An air- conditioned 2nd story storage area is accessed by elevator. The commercial kitchen, comfortable gathering area, and private lounge create a truly unique environment for entertaining and displaying prized possessions. Additional features include a 6-car pavilion and BBQ pergola with a stone fire pit. Structures are versatile - offering endless possibilities for collectors, creatives, or future expansion. The sweeping setting captures serene lake and sunset views, while a whole-property generator and security system provide comfort and peace of mind. With ample room to expand, the existing residence can serve as a guest home while a new primary estate is brought to life. Zoned for horses and ideally located just minutes from Hamlin Town Center, with convenient access to SR-429, Walt Disney World, and downtown Winter Garden, this is a rare opportunity to create a true legacy compound. All TV's included. Furnishings and other items may be available to purchase. See attachments for Feature Sheet.

Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)

Listing Agent: Judy Black (407-810-1803)

Remarks: A STUNNING, ENERGY-EFFICIENT HOME LOCATED IN ONE OF WINTER GARDEN’S MOST DESIRABLE GATED COMMUNITIES. Located at the highly desirable gated community of Lakeview Preserve, this 2021-built residence offers a rare combination of modern design, comfort, and quality of life in one of Central Florida’s fastest-growing and most appreciated areas. The home features 3 bedrooms and 2 bathrooms with a fully open and integrated floor plan that creates spacious, functional living areas filled with natural light, ideal for both everyday living and entertaining. A key highlight of this property is the installed solar panel system, providing meaningful energy savings, increased efficiency, and lower monthly utility costs, adding immediate value while aligning comfort with sustainability. Lakeview Preserve is a distinctive community surrounded by nature and thoughtfully designed to deliver leisure, security, and well-being. In addition to being a gated and well-maintained neighborhood, the community offers a full range of amenities, including a swimming pool, fitness center, clubhouse for various activities and events, a splash pad, lake access with designated kayaking areas, and inviting outdoor spaces that promote a relaxed and family-friendly atmosphere. The location is strategic, with convenient access to major roadways, highly rated schools, shopping, dining, and all that Winter Garden has to provide, making this property an excellent choice for both homeowners and investors seeking long-term value, strong demand, and consistent appreciation.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Simone De Souza Nunes Silva (689-837-5076)

Remarks: Under Construction. What's Special: Covered Extended Lanai | Close to Park | Dedicated Study | Garden View. New Construction - September Completion! Built by America's Most Trusted Home Builder. Welcome to the Caicos at 11283 Silver Trumpet Loop in Esplanade at McKinnon Groves! Step inside and enjoy an open concept living space filled with natural light that brings the heart of the home to life. At the front of the home, a secondary bedroom sits near a roomy laundry room and a private study with pocket doors, offering flexibility for work or guests. Tucked at the back of the home, the elegant primary suite creates a peaceful retreat and features a spacious walk-in closet, a dual sink vanity, and an expansive shower designed for everyday comfort and relaxation. Additional Highlights Include: tray ceiling package, a study with pocket doors in place of a flex room, a covered extended lanai, upgraded cabinetry and countertops. Photos are for representative purposes only. MLS#O6394269 - Esplanade at McKinnon Groves brings resort-style living to Winter Garden with beautifully designed open-concept homes set among natural views. This vibrant gated community offers a lifestyle centered on wellness, unique experiences, and signature amenities that make every day feel like a getaway. The Venue will feature a fitness center, movement studio, treatment room, lifestyle spaces, outdoor terrace seating, Bahama bar, and a resort pool with a spa and cabanas. You’ll also enjoy fireside seating, yoga and flex lawns, pickleball, tennis and bocce courts, a bark park, rose garden, and a trailhead connecting miles of equestrian and walking trails. Concierge services and year-round events elevate the experience even more. With zoning for Lake County public schools, this community blends everyday convenience with resort-style comfort!

Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)

Listing Agent: Michelle Campbell (407-756-5025)