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Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!

5 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!

105 Pine Street, Windermere

$925,000

Freshly remodeled and full of charm, this one-story home lives light, bright, and effortlessly easy. White oak floors flow from room to room like a warm welcome, setting the stage for airy spaces and sun-drenched corners. At the heart of the home, the family room opens wide with vaulted ceilings, a cozy fireplace, and windows that pull the outdoors in. The kitchen feels like the place everyone wants to gather, with a wraparound breakfast bar, quartz countertops, a wine fridge, and a cheerful breakfast nook that soaks in the morning light. Just beyond, a spacious dining room offers the ideal spot for long dinners, holiday celebrations, or spreading out homework and craft projects. A bonus room with plantation shutters adds an extra dash of flexibility — office, playroom, studio, you choose. The magic continues outside. French doors from the primary suite open straight to the pool, giving the whole space a resort-like feel. The oversized, solar-heated pool sits amid a lush, fenced backyard. A covered lanai waits for afternoon lounging, weekend barbecues, or quiet mornings with coffee and birdsong. Practical touches shine just as brightly, including an abundance of windows, a sunny laundry room near the primary suite, a functional open layout, and a 2-car garage offering storage and everyday convenience. Walk or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience. Move-in ready and filled with character, this home delivers a blend of comfort, beauty, and easy Florida living.

3 Beds ⋅ 2 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Freshly remodeled and full of charm, this one-story home lives light, bright, and effortlessly easy. White oak floors flow from room to room like a warm welcome, setting the stage for airy spaces and sun-drenched corners. At the heart of the home, the family room opens wide with vaulted ceilings, a cozy fireplace, and windows that pull the outdoors in. The kitchen feels like the place everyone wants to gather, with a wraparound breakfast bar, quartz countertops, a wine fridge, and a cheerful breakfast nook that soaks in the morning light. Just beyond, a spacious dining room offers the ideal spot for long dinners, holiday celebrations, or spreading out homework and craft projects. A bonus room with plantation shutters adds an extra dash of flexibility — office, playroom, studio, you choose. The magic continues outside. French doors from the primary suite open straight to the pool, giving the whole space a resort-like feel. The oversized, solar-heated pool sits amid a lush, fenced backyard. A covered lanai waits for afternoon lounging, weekend barbecues, or quiet mornings with coffee and birdsong. Practical touches shine just as brightly, including an abundance of windows, a sunny laundry room near the primary suite, a functional open layout, and a 2-car garage offering storage and everyday convenience. Walk or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience. Move-in ready and filled with character, this home delivers a blend of comfort, beauty, and easy Florida living.

1209 Main Street, Windermere

$880,000

Property is currently under contract; seller will consider backup offers Approximately 3,000 sq ft home in a desirable Windermere location within FEMA Flood Zone X. Buyer is responsible for verifying all measurements, dimensions, and square footage The residence offers a flexible layout with multiple living areas and is fully livable, presenting an excellent opportunity for buyers seeking long-term value and equity potential in one of Central Florida’s most established and highly regarded residential markets. Nearby Schools & Community Amenities Conveniently located near Windermere Elementary School on Park Avenue and the Windermere Recreation Center (Butler Bay), which offers lake access, a boardwalk, playground, picnic areas, and open green space along the Butler Chain of Lakes. Luxury Market Areas & Subdivision Context The Property is surrounded by well-established luxury residential communities with home values frequently exceeding $1,000,000. Nearby communities include Isleworth, Casabella at Windermere, and the Butler Bay / Windermere Club area, reinforcing the strong market fundamentals and long-term desirability of the Park Avenue corridor. Recreation, Shopping & Location Benefits The property offers easy access to area golf courses, parks, walking trails, marinas, and everyday conveniences. Located minutes from dining, shopping, and entertainment along International Drive, with convenient connections to major roadways serving Windermere, Orlando, and surrounding communities. Recent price improvement reflects the seller’s decision to position the property competitively within the current Windermere market Showings available upon request

5 Beds ⋅ 4 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Property is currently under contract; seller will consider backup offers Approximately 3,000 sq ft home in a desirable Windermere location within FEMA Flood Zone X. Buyer is responsible for verifying all measurements, dimensions, and square footage The residence offers a flexible layout with multiple living areas and is fully livable, presenting an excellent opportunity for buyers seeking long-term value and equity potential in one of Central Florida’s most established and highly regarded residential markets. Nearby Schools & Community Amenities Conveniently located near Windermere Elementary School on Park Avenue and the Windermere Recreation Center (Butler Bay), which offers lake access, a boardwalk, playground, picnic areas, and open green space along the Butler Chain of Lakes. Luxury Market Areas & Subdivision Context The Property is surrounded by well-established luxury residential communities with home values frequently exceeding $1,000,000. Nearby communities include Isleworth, Casabella at Windermere, and the Butler Bay / Windermere Club area, reinforcing the strong market fundamentals and long-term desirability of the Park Avenue corridor. Recreation, Shopping & Location Benefits The property offers easy access to area golf courses, parks, walking trails, marinas, and everyday conveniences. Located minutes from dining, shopping, and entertainment along International Drive, with convenient connections to major roadways serving Windermere, Orlando, and surrounding communities. Recent price improvement reflects the seller’s decision to position the property competitively within the current Windermere market Showings available upon request

11472 Park Avenue Ne, Windermere

$520,000

Almost half an acre located on Main Street in the Town of Windermere

Windermere SubDv. ⋅ 34786 Zip Code

Almost half an acre located on Main Street in the Town of Windermere

2 Chase Road, Windermere

$201,500

Welcome to Windermere. *NEW ROOF INSTALLED DEC 2024* This spacious home features 3 bedrooms, 2.5 bathrooms, and a den. The primary bedroom is downstairs and offers 2 walk in closets, dual vanities, and walk in shower. The den has a walk in closet and could easily be converted to a fourth bedroom - it only needs a door! Enjoy the soaring ceilings with solar tubes for natural light. With no rear neighbor you have a private view from your Florida room. Your 2nd and 3rd bedroom are upstairs and share a full bath. The upstairs overlook has a railing and is open with a view of the downstairs living space. For your storage needs there is a walk in attic as well as large linen closet. This community HOA includes irrigation, cable, internet, lawncare, exterior paint, and amenities for a low monthly fee of $284. The featured amenities in Windermere are the pool, clubhouse, boat/RV storage, and lake access. Windermere has easy access to the paved 46 mile Withlacoochee State Trail for outdoor enthusiasts.

3 Beds ⋅ 3 Baths ⋅ Windermere SubDv. ⋅ 34453 Zip Code

Welcome to Windermere. *NEW ROOF INSTALLED DEC 2024* This spacious home features 3 bedrooms, 2.5 bathrooms, and a den. The primary bedroom is downstairs and offers 2 walk in closets, dual vanities, and walk in shower. The den has a walk in closet and could easily be converted to a fourth bedroom - it only needs a door! Enjoy the soaring ceilings with solar tubes for natural light. With no rear neighbor you have a private view from your Florida room. Your 2nd and 3rd bedroom are upstairs and share a full bath. The upstairs overlook has a railing and is open with a view of the downstairs living space. For your storage needs there is a walk in attic as well as large linen closet. This community HOA includes irrigation, cable, internet, lawncare, exterior paint, and amenities for a low monthly fee of $284. The featured amenities in Windermere are the pool, clubhouse, boat/RV storage, and lake access. Windermere has easy access to the paved 46 mile Withlacoochee State Trail for outdoor enthusiasts.

821 Inverie Drive, Inverness