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1915 E Concord Street, Orlando
$425,000
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

206 N Highland Avenue, Winter Garden
$1,100,000
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

72 N Park Avenue Unit 8, Winter Garden
$1,149,000
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

1008 E Ridgewood St, Orlando
$1,050,000
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

131 Oak Laurel Drive, Winter Garden
$799,000
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