Vintage homes for sale & real estate in Winter Garden, FL

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ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Welcome home to 40 W Smith St. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's market, West Orange Trail, and the famed Crooked Can Brewery. This prime location home is nestles in the heart of downtown Winter Garden with easy access to local shops, restaurants, parks, and the vibrant community events that define this sought-after area. Original architectural details reflects the home's 1920's heritage, offering a unique blend of past and present. Some of modern hi

$750,000

4 beds2 baths2,225 sq ft

40 W Smith St, Winter Garden, FL 34787

West orange trail • Crooked can brewery • Historic home

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural zoning create one of Winter Garden’s last truly rare, low-density communities. Welcome to this fully remodeled, modern lakefront retreat on the shores of Lake Avalon, offering the perfect balance of sophistication, privacy, and convenience. Situated on almost 1.5 acres of fenced, irrigated land, this stunning single-story home features 3 bedrooms, 3.5 baths, and approximately 2,400 sq. ft. of living space with an attached 2-car garage—all meticulously updated with high-end finishes throughout. Step inside to an open, airy floor plan filled with natural light and luxury vinyl wood flooring t

$1,175,000

3 beds3.5 baths2,400 sq ft

17661 Davenport Rd, Winter Garden, FL 34787

Lakefront living • Private pathway • Spa style bathroom

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Completely Renovated 4BR/2BA Home – Walk to Downtown Winter Garden located just steps from the vibrant heart of Downtown Winter Garden. This move-in-ready property has been thoughtfully renovated from top to bottom, offering modern comfort and timeless style. 4 spacious bedrooms and 2 full bathrooms Fully renovated with new roof, plumbing, HVAC, and electrical systems Custom finishes throughout, including designer lighting, flooring, and fixtures Open-concept living and dining areas perfect for entertaining Prime location within walking distance to Plant Street shops, restaurants, farmers market, and West Orange Trail Whether you're looking for a stylish family home or a prime inves

$749,000

4 beds2 baths1,720 sq ft

229 N Highland Ave, Winter Garden, FL 34787

Renovated • Corner unit • Prime location

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner o

$1,800,000

3 beds2.5 baths3,507 sq ft

241 N Dillard St, Winter Garden, FL 34787

Triple lot • Golf cart district • 0.64 acre lot

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Investor special or perfect project home just steps from historic Downtown Winter Garden! This 2-bedroom, 1-bath bungalow sits on a generous lot and offers tons of potential for renovation or redevelopment. Bring your vision to life—restore its original charm or reimagine the space entirely. The location can’t be beat—walk or bike to the West Orange Trail, popular shops, restaurants, and the weekly farmers market. With its prime downtown location and solid bones, 329 W Bay Street is a rare opportunity to create your dream home or next investment property in one of Central Florida’s most sought-after communities.

$420,000

2 beds1 bath1,004 sq ft

329 W Bay St, Winter Garden, FL 34787

Generous lot • Rare opportunity • West orange trail

Property at 515 9th St, Winter Garden, FL 34787, 3 beds, 2 baths

$287,900

3 beds2 baths770 sq ft

515 9th St, Winter Garden, FL 34787

Property at 515 N Boyd St, Winter Garden, FL 34787, 5 beds, 4 baths

$900,000

5 beds4 baths3,152 sq ft

515 N Boyd St, Winter Garden, FL 34787

Property at 636 Coke Ave, Winter Garden, FL 34787, 2 beds, 1 bath

$339,999

2 beds1 bath914 sq ft

636 Coke Ave, Winter Garden, FL 34787

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ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
CANAL FRONTAGE ON 2 SIDES! Extremely RARE in the TOWN OF WINDERMERE, a single story 3/2 in a CUL-DE-SAC, on a PAVED STREET with a DOCK and CANALS ON 2 SIDES giving DIRECT ACCESS to LAKE DOWN AND WASEON BAY and the ENTIRE BUTLER CHAIN BEYOND. This lovingly maintained home is move-in ready, ready for your personal touches, or the ideal lot for your waterfront dream home. Extensive landscaping with abundant flowering plants and a covered front porch provide a warm welcome to this spacious ranch home. A foyer divides the kitchen and living spaces from the bedroom wing. The kitchen features solid surface countertops, wood cabinets and a breakfast nook with views of Lake Down. A large formal dini

$1,195,000

3 beds2 baths2,152 sq ft

2 Oakdale St, Windermere, FL 34786

Natural gas home • Sauna • Covered dock

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an . 8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite

$1,650,000

6 beds7.5 baths5,614 sq ft

620 N Tubb St, Oakland, FL 34760

Tall windows • 10 ceilings • Florida room

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still remains, giving this home a charm that simply can’t be recreated. The family room feels like a cozy tale come to life with its high ceilings, original wood floors, beadboard ceiling, and brick fireplace—the kind of spot that begs for gatherings, laughter, and quiet evenings by the fire. Sunlight pours through an abundance of windows, making every corner feel warm and cheerful. A sunny dinette awaits weekend breakfasts, while the formal living room offers a refined space for hosting or u

$885,000

2 beds1.5 baths2,115 sq ft

416 Magnolia St, Windermere, FL 34786

Brick fireplace • Sunny dinette • Original wood floors

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
C2 Zoning + Residential! Discover a unique lakefront opportunity on Lake Apopka featuring both a spacious residential home and versatile C2 zoning—ideal for a wide range of commercial uses. This property is perfect for an experienced buyer looking to restore a classic lakefront charmer, or for a small business owner seeking room to expand. It also offers tremendous potential for anyone with a creative vision for a new lakefront venture. Inside, the home offers plenty of character, including an updated kitchen with 3 ovens, large island and lots of storage, real wood floors and a walk-out basement. The home has one full bathroom and bedroom on the main floor. Second Floor has 3 bedro

$749,000

4 beds1 bath3,602 sq ft

3828 Walker Rd, Apopka, FL 32703

C2 zoning • Enclosed carport • Dock

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
Lake Minnehaha living at its finest. Set on 1.15 acres with no HOA, this beautifully updated and expanded property offers 4,755 sqft of refined lakefront comfort. The original 1950 home was fully remodeled in 2019 with a new roof in 2020, then elevated again with a 2023 addition that seamlessly blends modern style with the home’s classic charm. The main residence features 3,930 sqft, 3 bedrooms, 2 baths, a flexible Florida room/office, a massive home gym right off the primary suite and a very generous his and her walk in closet. The newly added 1,170-sqft living area enhances the flow of the home with updated finishes and a generator providing added convenience and security. A detache

$1,800,000

5 beds4 baths4,755 sq ft

12434 Lakeshore Dr, Clermont, FL 34711

Fully remodeled • Updated finishes • Massive home gym

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Winter Garden, FL:
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintai

$375,000

3 beds2 baths1,338 sq ft

507 W Oakland Ave, Oakland, FL 34760

Flexible space • Neighborhood park • Breakfast bar

Property at 11002 Lake Butler Blvd, Windermere, FL 34786, 5 beds, 7 baths

$4,200,000

5 beds7 baths6,248 sq ft

11002 Lake Butler Blvd, Windermere, FL 34786

Property at 18715 County Road 455, Clermont, FL 34715, 5 beds, 3.5 baths

$999,999

5 beds3.5 baths3,654 sq ft

18715 County Road 455, Clermont, FL 34715

Property at 311 E 8th Ave, Windermere, FL 34786, 5 beds, 4 baths

$1,660,000

5 beds4 baths3,805 sq ft

311 E 8th Ave, Windermere, FL 34786

Property at 2121 Woodland Dr, Apopka, FL 32703, 3 beds, 1 bath

$289,999

3 beds1 bath1,008 sq ft

2121 Woodland Dr, Apopka, FL 32703

Property at 770 Broone, Clermont, FL 34711, 2 beds, 2 baths

$249,999

2 beds2 baths— sq ft

770 Broone, Clermont, FL 34711

(305) 914-7653

Property at Undisclosed address, Ocoee, FL 34761, 3 beds, 2 baths

$1,000,000

3 beds2 baths1,676 sq ft

Undisclosed address, Ocoee, FL 34761

Property at 16724 Highland Ave, Montverde, FL 34756, 3 beds, 1.5 baths

$415,000

3 beds1.5 baths1,293 sq ft

16724 Highland Ave, Montverde, FL 34756

Property at 12550 Lakeshore Dr, Clermont, FL 34711, 5 beds, 4 baths

$1,399,000

5 beds4 baths4,056 sq ft

12550 Lakeshore Dr, Clermont, FL 34711

Property at 307 E Orlando Ave, Ocoee, FL 34761

$239,000

— beds— baths— sq ft

307 E Orlando Ave, Ocoee, FL 34761

Property at 2505 Fishermans Paradise Rd, Apopka, FL 32703

$1,425,000

— beds— baths— sq ft

2505 Fishermans Paradise Rd, Apopka, FL 32703

Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Winter Garden

There are currently 8 vintage homes for sale in Winter Garden at a median listing price of $650K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Garden stay on the market for 70 days and receive 1 offers. Popular neighborhoods include Lake Avalon Groves, Village of Bridgewater, Signature Lakes, Stoneybrook West, and Bella Collina. This map is refreshed with the newest listings in Winter Garden every 15 minutes.

In the past month, 56 homes have been sold in Winter Garden. In addition to houses in Winter Garden, there were also 23 condos, 30 townhouses, and 1 multi-family unit for sale in Winter Garden last month. Winter Garden is a minimally walkable city in Orange County with a Walk Score of 30. Winter Garden is home to approximately 33,581 people and 9,677 jobs. Find your dream home in Winter Garden using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Garden are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Garden. Our Winter Garden real estate stats and trends will give you more information about home buying and selling trends in Winter Garden. If you're looking to sell your home in the Winter Garden area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Garden with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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