MoveWithTrott.com Search Results

BACK TO THE MARKET! THE PREVIOUS BUYER WAS UNABLE TO SECURE FINANCING. Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes- Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends. The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere. The home's aluminum wiring has been remediated throughout, with the exception of the kitchen. ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019

3 Beds ⋅ 3 Baths ⋅ O6421738 MLS

BACK TO THE MARKET! THE PREVIOUS BUYER WAS UNABLE TO SECURE FINANCING. Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes- Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends. The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere. The home's aluminum wiring has been remediated throughout, with the exception of the kitchen. ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019

2053 Woody Drive, Windermere

$1,295,000

No detail overlooked in this beautifully reimagined 6BR/5BA estate in the sought-after lakefront community of Windermere Downs! Fully renovated and expanded with high-caliber craftsmanship, this home offers the ultimate Central Florida lifestyle. The lower level boasts rich tongue-and-groove ceilings, hardwood floors, plantation shutters, double-pane vinyl windows, and bright natural light. The expansive primary suite features a custom 10’x20’ walk-in closet and spa-like bathroom. Every bedroom enjoys en-suite bath access, including the private 780 sq ft upper-level suite with stunning Lake Down sunset views. The spacious kitchen and breakfast nook anchor the home, flowing into a living room with a stunning floor-to-ceiling picture window and French doors that open to your backyard oasis. Step outside to a private resort-style paradise complete with a sport pool, sun shelf, earth-toned pavers, summer kitchen, fire pit, and remodeled pool bath. Major mechanical updates ensure total peace of mind: Spray foam insulation (2025), main HVAC (2019-2023), new water heater, upgraded plumbing, lighting, and interior laundry room. Enjoy deeded access to the Butler Chain of Lakes via Windermere Downs’ crown jewel private beach lot on Lake Down, plus tennis/pickleball courts and park spaces. Unbeatable location—10 mins to Turnpike/408/429 and 25 mins to Disney, MCO Airport, and Downtown Orlando!

6 Beds ⋅ 5 Baths ⋅ O6443475 MLS

No detail overlooked in this beautifully reimagined 6BR/5BA estate in the sought-after lakefront community of Windermere Downs! Fully renovated and expanded with high-caliber craftsmanship, this home offers the ultimate Central Florida lifestyle. The lower level boasts rich tongue-and-groove ceilings, hardwood floors, plantation shutters, double-pane vinyl windows, and bright natural light. The expansive primary suite features a custom 10’x20’ walk-in closet and spa-like bathroom. Every bedroom enjoys en-suite bath access, including the private 780 sq ft upper-level suite with stunning Lake Down sunset views. The spacious kitchen and breakfast nook anchor the home, flowing into a living room with a stunning floor-to-ceiling picture window and French doors that open to your backyard oasis. Step outside to a private resort-style paradise complete with a sport pool, sun shelf, earth-toned pavers, summer kitchen, fire pit, and remodeled pool bath. Major mechanical updates ensure total peace of mind: Spray foam insulation (2025), main HVAC (2019-2023), new water heater, upgraded plumbing, lighting, and interior laundry room. Enjoy deeded access to the Butler Chain of Lakes via Windermere Downs’ crown jewel private beach lot on Lake Down, plus tennis/pickleball courts and park spaces. Unbeatable location—10 mins to Turnpike/408/429 and 25 mins to Disney, MCO Airport, and Downtown Orlando!

9668 Woodmont Place, Windermere

$1,025,000

Experience refined living at 1804 Maple Leaf Drive, an impeccably maintained corner-lot residence nestled in the highly sought-after community of Windermere Downs. Offering nearly 3,000 square feet of thoughtful design, this light-filled home features hardwood floors, solid wood cabinetry, and an inviting layout perfect for both entertaining and everyday comfort. With 4 spacious bedrooms, 3.5 bathrooms, and a dedicated home office, the floor plan provides exceptional flexibility and style. A 2019 roof adds peace of mind, while the outdoor retreat creates a private oasis ideal for relaxation and gatherings. Windermere Downs offers exceptional lifestyle amenities, featuring the only community lakefront lot on Lake Down with deeded Butler Chain of Lakes access for all homeowners. Enjoy a sand beach, a dock with gazebo, and a private boat ramp for launching watercrafts. The community also includes two tennis courts (one lined for pickleball) and multiple playgrounds, making it a true haven for recreation and outdoor living. Just minutes from the East-West Expressway, Disney, Universal, and premier dining and shopping, this home perfectly blends luxury, convenience, and timeless appeal.

4 Beds ⋅ 4 Baths ⋅ O6364182 MLS

Experience refined living at 1804 Maple Leaf Drive, an impeccably maintained corner-lot residence nestled in the highly sought-after community of Windermere Downs. Offering nearly 3,000 square feet of thoughtful design, this light-filled home features hardwood floors, solid wood cabinetry, and an inviting layout perfect for both entertaining and everyday comfort. With 4 spacious bedrooms, 3.5 bathrooms, and a dedicated home office, the floor plan provides exceptional flexibility and style. A 2019 roof adds peace of mind, while the outdoor retreat creates a private oasis ideal for relaxation and gatherings. Windermere Downs offers exceptional lifestyle amenities, featuring the only community lakefront lot on Lake Down with deeded Butler Chain of Lakes access for all homeowners. Enjoy a sand beach, a dock with gazebo, and a private boat ramp for launching watercrafts. The community also includes two tennis courts (one lined for pickleball) and multiple playgrounds, making it a true haven for recreation and outdoor living. Just minutes from the East-West Expressway, Disney, Universal, and premier dining and shopping, this home perfectly blends luxury, convenience, and timeless appeal.

1804 Maple Leaf Drive, Windermere

$700,000

Seller says SELL! Listed $20,000 BELOW APPRAISED value!!! Discover this exquisite 3-bedroom, 3.5-bathroom pool home nestled on a lush 1/3-acre lot in the prestigious Windermere Downs community. Spanning 3,100 square feet, this property combines sophisticated design, functionality, and beautiful indoor-outdoor living spaces. Upon entry, you’re greeted by luxury vinyl flooring that flows through a spacious, open floor plan. The heart of the home is the modern chef’s kitchen, featuring butcher block countertops, premium appliances and abundant storage. Perfect for entertaining, this kitchen flows seamlessly into the living and dining areas, where large windows and three sets of French doors provide panoramic views of the courtyard and screened-in pool area. The living room exudes warmth with its impressive stone fireplace, creating a cozy atmosphere. Upstairs you will find the primary suite that offers privacy and luxury, complete with a decorative fireplace surrounded by custom-built cabinetry. Its en-suite bath features dual vanities, a claw soaking tub, and a walk-in shower, providing a spa-like escape. The best part, is the Sun Room, just outside of the Primary Bedroom, flooded by light due to its 180 degree view with windows overlooking the pool, courtyard, and lush green surroundings. Outside, the screened-in pool is a tranquil oasis surrounded by mature landscaping, creating a sense of seclusion. A gardening shed, which could double as a charming playhouse, sits nearby, offering versatile space amid lush greenery. The expansive courtyard and pool area, surrounded by carefully curated plantings, are designed with privacy in mind, allowing you to enjoy Florida’s beautiful weather in peace. Last but not least, don't forget about the 3 car garage and extended driveway which is perfect for car enthusiasts. Windermere Downs is an avid boating community with a private boat ramp! Neighborhood amenities include tennis courts, pickleball courts, playgrounds, and private lake access. This prime location sets you about 10 minutes from the 408, the 429, and easy access to the turnpike-the accessibility of Central Florida's many attractions are minutes away. Seize the opportunity to make this exquisite Windermere property your forever home!

3 Beds ⋅ 4 Baths ⋅ O6256640 MLS

Seller says SELL! Listed $20,000 BELOW APPRAISED value!!! Discover this exquisite 3-bedroom, 3.5-bathroom pool home nestled on a lush 1/3-acre lot in the prestigious Windermere Downs community. Spanning 3,100 square feet, this property combines sophisticated design, functionality, and beautiful indoor-outdoor living spaces. Upon entry, you’re greeted by luxury vinyl flooring that flows through a spacious, open floor plan. The heart of the home is the modern chef’s kitchen, featuring butcher block countertops, premium appliances and abundant storage. Perfect for entertaining, this kitchen flows seamlessly into the living and dining areas, where large windows and three sets of French doors provide panoramic views of the courtyard and screened-in pool area. The living room exudes warmth with its impressive stone fireplace, creating a cozy atmosphere. Upstairs you will find the primary suite that offers privacy and luxury, complete with a decorative fireplace surrounded by custom-built cabinetry. Its en-suite bath features dual vanities, a claw soaking tub, and a walk-in shower, providing a spa-like escape. The best part, is the Sun Room, just outside of the Primary Bedroom, flooded by light due to its 180 degree view with windows overlooking the pool, courtyard, and lush green surroundings. Outside, the screened-in pool is a tranquil oasis surrounded by mature landscaping, creating a sense of seclusion. A gardening shed, which could double as a charming playhouse, sits nearby, offering versatile space amid lush greenery. The expansive courtyard and pool area, surrounded by carefully curated plantings, are designed with privacy in mind, allowing you to enjoy Florida’s beautiful weather in peace. Last but not least, don't forget about the 3 car garage and extended driveway which is perfect for car enthusiasts. Windermere Downs is an avid boating community with a private boat ramp! Neighborhood amenities include tennis courts, pickleball courts, playgrounds, and private lake access. This prime location sets you about 10 minutes from the 408, the 429, and easy access to the turnpike-the accessibility of Central Florida's many attractions are minutes away. Seize the opportunity to make this exquisite Windermere property your forever home!

9792 Wild Oak Drive, Windermere

$710,000

Nestled in the sought-after community of Windermere Downs, this California-contemporary home sits on a large wooded corner lot with ACCESS to the BUTLER CHAIN OF LAKES. A dramatic two-story stone fireplace anchors the open layout, featuring a downstairs primary suite plus a flexible second bedroom or office. The designer kitchen offers solid-wood cabinetry, granite counters, and stainless-steel built-ins, opening to bright dining and living areas. Ready for its next chapter, this home offers endless potential to bring your lake-access dream vision to life. Enjoy a generous rear deck, outdoor shower, and fenced backyard in a community known for tennis, boating, and a beautiful private sandy beach. Private documents include rough builder sketches for a renovation, addition, and outdoor oasis.

4 Beds ⋅ 3 Baths ⋅ O6349778 MLS

Nestled in the sought-after community of Windermere Downs, this California-contemporary home sits on a large wooded corner lot with ACCESS to the BUTLER CHAIN OF LAKES. A dramatic two-story stone fireplace anchors the open layout, featuring a downstairs primary suite plus a flexible second bedroom or office. The designer kitchen offers solid-wood cabinetry, granite counters, and stainless-steel built-ins, opening to bright dining and living areas. Ready for its next chapter, this home offers endless potential to bring your lake-access dream vision to life. Enjoy a generous rear deck, outdoor shower, and fenced backyard in a community known for tennis, boating, and a beautiful private sandy beach. Private documents include rough builder sketches for a renovation, addition, and outdoor oasis.

9631 Hollyglen Place, Windermere

$670,000

Direct Lake Butler Chain of Lakes Access by Private Community Ramp on Lake Down - Windermere Downs is a Fantastic Active Golf Cart Friendly Community with Tennis & Pickleball Courts, Multiple Kids Play Areas - Walking & Dog Friendly - A Waterfront Community Park with Fishing Pier & Private Boat Ramp to Lake Down & The Butler Chain of Lakes - 3 Bed 2 Bath - Open Concept Split Plan - Fresh Paint - New Wide Plank Flooring - Fireplace - 2 Car Garage - Stainless Steel Appliances - Enclosed Porch for Additional Living Space - Large fenced yard - Washer / Dryer included - Owner financing available

3 Beds ⋅ 2 Baths ⋅ O6346978 MLS

Direct Lake Butler Chain of Lakes Access by Private Community Ramp on Lake Down - Windermere Downs is a Fantastic Active Golf Cart Friendly Community with Tennis & Pickleball Courts, Multiple Kids Play Areas - Walking & Dog Friendly - A Waterfront Community Park with Fishing Pier & Private Boat Ramp to Lake Down & The Butler Chain of Lakes - 3 Bed 2 Bath - Open Concept Split Plan - Fresh Paint - New Wide Plank Flooring - Fireplace - 2 Car Garage - Stainless Steel Appliances - Enclosed Porch for Additional Living Space - Large fenced yard - Washer / Dryer included - Owner financing available

2015 Woody Drive, Windermere

How much is your home worth?

How much is your home worth?