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Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code

Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden

$415,000

Tucked into the heart of Colonial Town South, 1915 East Concord Street is a 1937 bungalow that pairs original character with a comprehensive list of modern updates, offering buyers a rare combination of historic charm and move-in-ready confidence. The 1,438 square foot home features 3 bedrooms and 3 bathrooms on a 0.16 acre lot, with original hardwood floors running throughout and a bright front Florida sunroom that adds flexible living space. The kitchen is outfitted with stainless steel appliances, an inside laundry room adds everyday convenience, and a large, fully fenced backyard offers room to enjoy Florida living outdoors. A comprehensive list of updates gives buyers confidence from day one, including a 2023 roof, 2017 HVAC system, 2026 tankless water heater, and 2022 main water line. The home was tented in April 2024, and the front windows were replaced in 2025 with PGT Impact windows carrying a transferable 10-year warranty. Colonial Town South offers a rare blend of historic character and everyday convenience, just minutes from the Mills 50 District, East End Market, and Ivanhoe Village, with local breweries, boutiques, and some of Orlando's best dining nearby. Also close to Downtown Orlando, Thornton Park, and Lake Eola, this is one of Orlando's most sought-after historic neighborhoods.

3 Beds ⋅ 3 Baths ⋅ East View Park SubDv. ⋅ 32803 Zip Code

Tucked into the heart of Colonial Town South, 1915 East Concord Street is a 1937 bungalow that pairs original character with a comprehensive list of modern updates, offering buyers a rare combination of historic charm and move-in-ready confidence. The 1,438 square foot home features 3 bedrooms and 3 bathrooms on a 0.16 acre lot, with original hardwood floors running throughout and a bright front Florida sunroom that adds flexible living space. The kitchen is outfitted with stainless steel appliances, an inside laundry room adds everyday convenience, and a large, fully fenced backyard offers room to enjoy Florida living outdoors. A comprehensive list of updates gives buyers confidence from day one, including a 2023 roof, 2017 HVAC system, 2026 tankless water heater, and 2022 main water line. The home was tented in April 2024, and the front windows were replaced in 2025 with PGT Impact windows carrying a transferable 10-year warranty. Colonial Town South offers a rare blend of historic character and everyday convenience, just minutes from the Mills 50 District, East End Market, and Ivanhoe Village, with local breweries, boutiques, and some of Orlando's best dining nearby. Also close to Downtown Orlando, Thornton Park, and Lake Eola, this is one of Orlando's most sought-after historic neighborhoods.

1915 E Concord Street, Orlando

$1,050,000

Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.

3 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code

Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.

206 N Highland Avenue, Winter Garden

$1,099,000

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

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

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden

$1,050,000

UNIQUE OPPORTUNITY FOR MULTI-GENERATIONAL LIVING IN THE HEART OF DOWNTOWN ORLANDO! Designed for those seeking a primary residence with exceptional flexibility, this one-of-a-kind home offers two complete living spaces under one roof, allowing everyone to enjoy both connection and independence. The main residence features 4 bedrooms, 2 bathrooms, a spacious family room, full kitchen, and laundry room, while the private lower-level residence offers 2 bedrooms, 1 bathroom, a full kitchen, expansive living room, dining area, laundry room, and its own private entrance. Two kitchens, two laundry areas, generous living spaces, and separate accommodations create an incredibly versatile home that can adapt as your needs change. And then there is the lifestyle! Just a short stroll from iconic Lake Eola, experience the very best of Downtown Orlando living. Start your mornings walking around the lake, grab coffee at a neighborhood café, spend weekends at the Farmers Market, and enjoy concerts, festivals, outdoor activities, swan boat rides, and year-round events just moments from your front door. Explore vibrant dining, rooftop lounges, craft breweries, boutique shopping and nightlife, along with the Dr. Phillips Center for the Performing Arts, Kia Center, Inter&Co Stadium, and the Central Business District. With convenient access to SunRail and major highways, this is urban living at its finest in the heart of The City Beautiful. While this home shines as a primary residence, its versatility creates even more possibilities. The property is properly zoned for short-term rentals, and the current owner has successfully welcomed repeat guests while using the property as a primary residence. Live on either level while generating income from the other, lease one residence long-term, or simply enjoy the additional space for guests, a home office, hobbies, or whatever fits your lifestyle. Additional highlights include a remodeled main-floor kitchen and bathrooms, beautifully renovated lower-level residence, roof approximately nine years old, and transferable termite bond for added peace of mind. Opportunities like this are exceptionally rare. Few properties combine a prime Downtown Orlando location, true multi-generational living, two complete living spaces, and the flexibility for future income potential. Whether you're searching for a forever home, need independent living spaces under one roof, or simply want a residence capable of evolving with your lifestyle, 1008 E. Ridgewood Street offers something truly difficult to duplicate. Schedule your private showing today!

6 Beds ⋅ 3 Baths ⋅ Eola Park Heights SubDv. ⋅ 32803 Zip Code

UNIQUE OPPORTUNITY FOR MULTI-GENERATIONAL LIVING IN THE HEART OF DOWNTOWN ORLANDO! Designed for those seeking a primary residence with exceptional flexibility, this one-of-a-kind home offers two complete living spaces under one roof, allowing everyone to enjoy both connection and independence. The main residence features 4 bedrooms, 2 bathrooms, a spacious family room, full kitchen, and laundry room, while the private lower-level residence offers 2 bedrooms, 1 bathroom, a full kitchen, expansive living room, dining area, laundry room, and its own private entrance. Two kitchens, two laundry areas, generous living spaces, and separate accommodations create an incredibly versatile home that can adapt as your needs change. And then there is the lifestyle! Just a short stroll from iconic Lake Eola, experience the very best of Downtown Orlando living. Start your mornings walking around the lake, grab coffee at a neighborhood café, spend weekends at the Farmers Market, and enjoy concerts, festivals, outdoor activities, swan boat rides, and year-round events just moments from your front door. Explore vibrant dining, rooftop lounges, craft breweries, boutique shopping and nightlife, along with the Dr. Phillips Center for the Performing Arts, Kia Center, Inter&Co Stadium, and the Central Business District. With convenient access to SunRail and major highways, this is urban living at its finest in the heart of The City Beautiful. While this home shines as a primary residence, its versatility creates even more possibilities. The property is properly zoned for short-term rentals, and the current owner has successfully welcomed repeat guests while using the property as a primary residence. Live on either level while generating income from the other, lease one residence long-term, or simply enjoy the additional space for guests, a home office, hobbies, or whatever fits your lifestyle. Additional highlights include a remodeled main-floor kitchen and bathrooms, beautifully renovated lower-level residence, roof approximately nine years old, and transferable termite bond for added peace of mind. Opportunities like this are exceptionally rare. Few properties combine a prime Downtown Orlando location, true multi-generational living, two complete living spaces, and the flexibility for future income potential. Whether you're searching for a forever home, need independent living spaces under one roof, or simply want a residence capable of evolving with your lifestyle, 1008 E. Ridgewood Street offers something truly difficult to duplicate. Schedule your private showing today!

1008 E Ridgewood St, Orlando

$1,095,000

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.

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

$799,000

131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an elevator that conveniently connects the first and second floors along with an oversized rear-entry two-car garage, a small balcony, and a convenient in-unit laundry closet. Inside, the open-concept main level boasts a gourmet kitchen with stainless steel appliances, a large island, and ample cabinetry. Premium finishes throughout include wood-look tile flooring, crown molding, and plantation shutters. The primary suite offers generous closet space and a spa-inspired bath with dual vanities, a soaker tub, and a walk-in shower. Thoughtful design and quality craftsmanship combine with a prime location just steps from downtown Winter Garden’s restaurants, shops, and the Plant Street Market, making this property an exceptional opportunity to enjoy upscale living in one of the area’s most sought-after neighborhoods.

3 Beds ⋅ 4 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code

131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an elevator that conveniently connects the first and second floors along with an oversized rear-entry two-car garage, a small balcony, and a convenient in-unit laundry closet. Inside, the open-concept main level boasts a gourmet kitchen with stainless steel appliances, a large island, and ample cabinetry. Premium finishes throughout include wood-look tile flooring, crown molding, and plantation shutters. The primary suite offers generous closet space and a spa-inspired bath with dual vanities, a soaker tub, and a walk-in shower. Thoughtful design and quality craftsmanship combine with a prime location just steps from downtown Winter Garden’s restaurants, shops, and the Plant Street Market, making this property an exceptional opportunity to enjoy upscale living in one of the area’s most sought-after neighborhoods.

131 Oak Laurel Drive, Winter Garden

$1,500,000

GATED LAKEFRONT HOUSE WITH PRIVATE BOAT DOCK AROUND SEAWORLD! This 3 Bed/ 2.5 Bath single family house features 4.44 ACRES LOT and nested in Lake Willas, one of Orlando HIDDEN GEM. The home boasts an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating a cohesive living space. Each floor has individual kitchen and laundry rooms. Unbeatable location with close proximity to Orlando theme parks, shoppings, restaurants and entertainment, airport, and downtown. All this and NO HOA. Schedule a private showing today and make this beautiful home your new residence or build your dream home at this remarkable LAKEFRONT LOT!

3 Beds ⋅ 3 Baths ⋅ Willis Camps Add 01 SubDv. ⋅ 32821 Zip Code

GATED LAKEFRONT HOUSE WITH PRIVATE BOAT DOCK AROUND SEAWORLD! This 3 Bed/ 2.5 Bath single family house features 4.44 ACRES LOT and nested in Lake Willas, one of Orlando HIDDEN GEM. The home boasts an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating a cohesive living space. Each floor has individual kitchen and laundry rooms. Unbeatable location with close proximity to Orlando theme parks, shoppings, restaurants and entertainment, airport, and downtown. All this and NO HOA. Schedule a private showing today and make this beautiful home your new residence or build your dream home at this remarkable LAKEFRONT LOT!

11424 Westwood Boulevard, Orlando

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