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32789 Zip Code Real Estate & Homes near Historic District

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$429,900
4 Beds 2 Baths Olympia Heights Annex SubDv. 32789 Zip Code
Under contract-accepting backup offers. Welcome to one of Orlando's most beloved neighborhoods, where tree-lined streets, golf course views, and a true sense of community create the lifestyle buyers are searching for. Perfectly positioned across from the 5th tee of historic Dubsdread Golf Course, this beautifully renovated home places you in the heart of the Dubsdread bubble—just minutes from the dining, shopping, and charm of both College Park and Winter Park. Set on an oversized .22-acre lot, this move-in-ready residence offers over 1,500 square feet of thoughtfully updated living space, blending classic character with today's most desired upgrades. Inside, you'll find refinished original hardwood floors, a fully renovated kitchen featuring stunning quartz countertops, new cabinetry, and new stainless steel appliances, plus two completely renovated bathrooms with fresh, timeless finishes. A 2023 rear addition adds valuable living space, while the inviting Florida room and screened porch provide the perfect spots to enjoy morning coffee, entertain friends, or unwind after a round of golf. Beyond the cosmetic improvements, the heavy lifting has already been done. Enjoy peace of mind with updated plumbing (2026) including removal of cast iron piping, updated electrical (2026), roof (2020), tankless water heater (2023), and energy-efficient windows (2023). Homes in the Dubsdread District rarely offer this combination of location, charm, lot size, and major renovations. Whether you're drawn to the golf course views, the walkable neighborhood feel, or the proximity to Orlando's best restaurants, parks, and entertainment, this home delivers the lifestyle that makes this area one of Orlando's most desirable places to call home. Move-in ready, extensively updated, and perfectly located—schedule your private showing today!

2249 Minnesota Avenue, Winter Park

$735,000
3 Beds 2 Baths Winter Park SubDv. 32789 Zip Code
Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.

738 S Pennsylvania Avenue, Winter Park

$1,589,000
4 Beds 3 Baths Virginia Heights SubDv. 32789 Zip Code
Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history of Winter Park, and within true walking distance of Rollins College, Park Avenue, and all the lively bustle of downtown Winter Park. Better yet, enjoy deeded lake access from the neighborhood lakefront park just a 3-minute walk from your front door, where neighbors gather for social events, holiday parties, and relaxing lake views. With a sprawling green lawn, dock, kayak/canoe storage racks, and picnic tables, the perfect daily retreat is just steps away. The home is move-in ready and bursting with charm, with over 2800 SF of thoughtfully designed space for everyday living and entertaining. The ideal, split-bedroom floorplan includes 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace (piped for gas), dining room with a built-in lighted bar, large family room, and over 400 SF of covered lanai space overlooking the pool & backyard paradise. The oversized primary suite is truly special, with room for a sitting area, tons of built-in storage, and a mirrored barn door that opens to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large zero-entry marble shower, custom mahogany-topped vanity, maple board-and-batten walls, brass fixtures, and cypress vaulted ceilings, plus 2 walk-in closets and a third storage closet at the bedroom entrance. The sunny family room extends to the rear of the home, where French doors are equipped with retractable screen doors for enjoying the breeze indoors and out, in true Key-West style. Past the French doors, a travertine lanai stretches across the back of the home and overlooks a lagoon-style pool and travertine deck, with surrounding palms and lush tropical landscaping to create the perfect backyard oasis. The kitchen features Thermador appliances, with a gas cooktop and a brand new vent hood framed by a new marble backsplash, and new pendant lighting over the breakfast bar. Both secondary bedrooms have French doors that open to the covered lanai, and en-suite bathrooms. Other conveniences include a whole-house sound system with interior and exterior speakers, custom laundry room (renovated in 2021), and 2-car garage with built-in storage. Move-in ready, the home was completely replumbed in July 2025, with a new gas water heater, partial roof replacement (all new flat roof in Aug 2025), up-to-date electrical, and (2) recently serviced 2019 HVAC units with UV lights. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$1,565,000
4 Beds 3 Baths Virginia Heights SubDv. 32789 Zip Code
Experience the charm and comfort of this one-story, Key West-style pool home, nestled on a brick-lined street and canopied by majestic oaks in the highly sought-after Virginia Heights neighborhood. Within true walking distance of Rollins College and Park Avenue, and in the Audubon K-8 school district, this home was thoughtfully designed for everyday living and entertaining. The 2,662 SF home features a split-bedroom floorplan with 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace piped for gas, dining room with a built-in lighted bar, a large family room, and a 400 SF covered lanai overlooking the pool & backyard paradise. The oversized primary suite is truly a retreat, with a sitting area plus a cozy window bench spanning a wall of windows with built-in cabinetry and shelves for ample storage. A mirrored barn door slides open to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large, zero-entry marble shower, mahogany-topped custom-crafted vanity, maple board-and-batten walls, brass fixtures, cypress vaulted ceilings, and windows overlooking the sparkling pool, with convenient top-down bottom-up privacy shades. Enjoy 2 walk-in closets, plus a third closet at the primary suite entrance that offers easy-access housing for the home’s AV equipment. The sunny family room, lined with built-ins and a custom-designed “wall of books,” extends to the back of the home. French doors with hidden screens open to the private backyard oasis, showcasing a travertine lanai, lagoon-style pool, and travertine deck surrounded by palms and lush tropical landscaping. At the heart of the home sits the kitchen with Thermador appliances— gas cooktop, built-in oven, convection oven/microwave, and dishwasher— and a breakfast bar, plus a brand new vent hood framed by a new marble backsplash, and new under-cabinet and pendant lighting. Both secondary bedrooms have French doors that open to the covered lanai, while the rear left bedroom offers a private, en-suite bathroom renovated in 2021, wrapped in marble and brass with coil-heated floors and a custom Kohler air-jet soaking tub. Other conveniences include a whole-house sound system with speakers in every room as well as the rear lanai, and a custom laundry room (renovated in 2021) that leads to a 2-car garage with built-in storage. Virginia Heights is truly a special neighborhood, offering residents deeded access to a private lakefront park that's just a 3-minute walk from this home. This hidden park was deeded to the property owners of Virginia Heights in 1922, and includes a dock on College Point directly across from Rollins College, canoe/kayak racks, tables for airy picnics in the lake breeze, and a sprawling green lawn where neighbors gather for social events, holiday parties, or just to enjoy the lake view. A part of the beloved culture and history of Winter Park, this unique property is just minutes from Rollins, the shops and restaurants of Park Avenue, and all the lively bustle of downtown Winter Park. Recent upgrades include a complete replumb and new gas water heater (July 2025), a partial roof replacement (all new flat roof), landscape clean-up/refresh, fresh paint inside and out, and all new lighting and ceiling fans throughout. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$1,175,000
3 Beds 2 Baths College Place Rep SubDv. 32789 Zip Code
Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter. Nestled in the heart of the historic College Quarter, this beautifully preserved 1925 Craftsman home offers timeless character, modern livability, and a rare bonus: a separate Spanish/Moorish-style garage apartment with its own unique architectural flair. The main house features 3 bedrooms, 2 bathrooms, and 1,867 square feet of inviting living space. Classic elements like original heart of pine floors and period finishes can easily blend in well with additional interior updating. Although the house has the history, the flow of the layout works well with today’s modern living and entertaining style. Additionally, just behind the main home, is a 504-square-foot garage apartment which offers a living space, kitchenette, bedroom and bathroom. It has striking interior details, such as hand-hewn pecky cypress beams, heavy plaster work, keyhole shaped doors and hand-wrought ironwork and a cozy fireplace. The apartment space is —a perfect guest retreat, income-producing rental, or private home office. The property also comes with deeded lake access to scenic Lake Virginia, part of the coveted Winter Park Chain of Lakes. The proximity to downtown Winter Park is just a short stroll, through tree-lined brick streets to Park Avenue’s shops and restaurants, as well as Rollins College, which is just a street away. Whether you're seeking historic character, walkable charm, or lakeside living, this unique Winter Park property delivers it all! 4-Point inspection was completed, please see attachments for survey and for home details.

835 Antonette Avenue, Winter Park

$1,595,000
3 Beds 3 Baths Cloister Grove Sub SubDv. 32789 Zip Code
Nestled in the heart of The Vias, this Mediterranean masterpiece encompasses 3,217 square feet of beauty and elegance for your enjoyment of living. Dating back to 1953, this iconic home rests on a corner lot, offering captivating views of Lake Knowles. A stately entrance greets you with a large open living and dining space adorned with a beautiful gas fireplace and hardwood floors. Continue your journey through the first floor to find your incredible gourmet kitchen accompanied by custom cabinetry, Viking gas range, marble backsplash, quartz countertops, stainless steel appliances, a warming drawer, oversized walk-in pantry and an abundance of natural light illuminating the space well. The main floor features a guest suite, a full bath, a spacious laundry room and an office that leads to the private backyard. The owner’s suite beckons you with its grandeur and features French doors that lead to a large, covered balcony overlooking Lake Knowles and an en-suite bath boasting a glass-enclosed shower, dual vanities, two custom walk-in closets, and a clawfoot tub where you can soak and take in some of the best views Winter Park has to offer. A second private staircase leads to an additional guest en suite, providing seclusion and luxurious living quarters for your family or guests. The enclosed backyard offers low-maintenance landscaping and also features a gas generator for additional peace of mind. Revel in the glorious views of the sunrise over Lake Knowles and enjoy being situated ideally, just a short golf cart ride from Park Avenue shops and restaurants, the Winter Park Racquet Club, and near Kraft Azalea Garden, Phelps Park and the Winter Park YMCA. An exclusive respite, this home represents the epitome of Winter Park living at its finest.

1250 Via Capri, Winter Park

$785,000
4 Beds 3 Baths Fairbanks Park SubDv. 32789 Zip Code
ZONED R-2. GREAT POTENTIAL INCOME GENERATOR!! This historic beauty is spacious and features a FULL APARTMENT ON TOP OF THE GARAGE. This apartment offers a private entrance so would be a fabulous, income producing unit or a great space for the in-laws or adult children needing a little more privacy. The options are endless. We’ve even heard buyers suggest a game room, gym, separate office, or man cave for the hunter in your life to hang their trophies. We love the enthusiasm. The open front porch is quite welcoming thanks to the side garage entry. No big garage door taking away from your curb appeal! Step inside to see the cozy living room with gas fireplace and to your right, a guest bedroom currently stages as an office. Head back to the large dining space then continue on to the lovely kitchen which is updated with white cabinets, stainless steel appliances, and granite counters. Enjoy a gas stove for the chefs in the home. To the right of the kitchen you will find a full sized bathroom, the 2nd bedroom and the master with en suite bathroom. You may be surprised to find such a spacious bathroom in a 1925 home! There are dual sinks and lots of cabinet storage, a jetted soaking tub, large walk-in shower and designer walk-in closet. The back of the home offers a huge desk area along with a pantry and the washer and dryer closet. This bonus space would make the perfect playroom or game room but again…endless possibilities to accommodate a creative homeowner. Step out the back door to a foyer which offers an additional storage closet and gives you the option of heading to the oversized two car garage or up the stairs to the garage apartment. This apartment has it’s own A/C unit and is laid out as an L shaped loft. You walk in to the bedroom area then turn left to the living area and the kitchen is in the corner. All a great, open floor plan. The door on the right leads to the full bathroom with its shower/tub combo. You’ll notice the space is light and bright thanks to the windows and French doors which lead to the long balcony. This PRIME location is in the heart of the highly sought after city of Winter Park. You’re less than a mile from Park Ave and all of its high ends shops and variety of restaurants. You’re walking distance from fabulous city parks and Rollins College. The Winter Park boat tour, art festivals, farmer’s market, etc etc are all a short walk from this unique gem of a home. Not to mention the easy access to I-4, the shops and restuarants on 1792 which lead to Maitland and downtown Orlando AND the Winter Park Village which is wrapping up a modern renovation. It’s truly the best of the best!!

1000 S Kentucky Avenue, Winter Park

$905,000
2 Beds 3 Baths Sylvan Lake Shores SubDv. 32789 Zip Code
"THE TRIANGLE HOUSE" New Roof, freshly painted outside, 2 airconditioners 1 new last year. 2 gas fireplaces, one in the master bedroom, the other in the living area. Creme Mafil floors and countertops. High ceilings throughout and a spectacular lot make a special setting for this sophisticated home. Mature landscaping gives privacy and beauty to a wonderful setting on a beautiful brick street in the heart of Winter Park. The street is extremely quiet with little or no traffic as it is a circle that only residents go down. . Large living and dining area opens to a well-planned kitchen with creme marfil floors, a kitchen bar and creme marfil countertops, and custom kitchen cabinetry. The first floor boasts a full bath with shower, laundry room, living area and dining area, counter bar area, and bay windows. Beautiful wood stairs with stainless steel and glass handrails and large windows lead to the second floor. Beautiful wood and glass sliding doors lead into the master suite. The large master bedroom, bath, dressing area, and office give privacy to the owners. Leading into the master suite, are beautiful opaque glass doors that add beauty and also privacy. The oversized master suite has a fireplace, stained glass window, and a spectacular bathroom and closet area. The master shower is oversized and off the bathroom is a private office that could be changed into a nursery exercise room, or private area. The Second Om suite has a jacuzzi tub and a beautiful stained-glass window over the jacuzzi area. Nice closet space and a view over to the lake. It is located on a brick street in desirable and friendly old Winter Park nationhood walking distance to Rollins, Park Ave and the chain of lakes restaurants, and shopping. The home has new air-conditioning on the first floor, a whole house generator, a gas stove and fireplaces, and a new lawn. Savannah's walled garden is perfect for cozy entertaining. This is a lovely home with a lot of flare!

1500 Harris Circle, Winter Park

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