Vintage homes for sale & real estate in 34787, FL

13 homes

Sort:

Recommended

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
This Downtown Winter Garden stunner has continued to evolve with thoughtful, high-value upgrades that make it even more exceptional today. Located in the much sought after golf cart district and just steps from Plant Street’s restaurants, markets, and year-round events, this home blends timeless character with modern convenience in a way few properties can match. Originally reimagined with a full professional remodel in 2023 — including brand-new roof, windows, electrical, plumbing, insulation, luxury vinyl plank flooring, Bosch appliances, Carrara quartz surfaces, and a magnificent, redesigned kitchen. Additional upgrades include a newly constructed one-car garage with parking

$849,900

4 beds2.5 baths2,331 sq ft

368 N Boyd St, Winter Garden, FL 34787

Whole-home generator • Professional remodel • Golf cart district

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
PHENOMENAL Double corner LOT NO HOA, newer updates INCLUDE: brand new AC, new roof, Re-Plumb, house/ Electrical Panel/rewired. Updated kitchen and bathrooms, Located off the Kitchen is the Dining room area which is open to the Living Room area. The master Bathrooms is completely updated features a standing shower. The Laundry is located inside. The carport/workshop is spacious to hold 2 cars and storage. Enjoy the nice-sized Backyard with a that is big enough for the whole family. You don't want to miss this opportunity to make this house your home! very nice WORKSHOP * * VALUE IS IN THE both property/land

$411,000

4 beds2 baths1,434 sq ft

689 Bethune Ave, Winter Garden, FL 34787

Double corner lot • Nice-sized backyard • Updated bathrooms

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the front are being sold seperate.

$800,000

4 beds2 baths2,868 sq ft

214 S Woodland St, Winter Garden, FL 34787

0.86 acre lot • 3 parking spots • Pool

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature

$289,000

2 beds2 baths825 sq ft

1701 E Bay St, Winter Garden, FL 34787

6,748 sq ft lot • Built 1950 • Listed 73 days

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with

$544,900

3 beds2 baths1,273 sq ft

46 W Vining St, Winter Garden, FL 34787

Golf cart district • Inside laundry • 0.24 acre lot

Property at 721 S Woodland St, Winter Garden, FL 34787, 2 beds, 1 bath

$440,000

2 beds1 bath1,034 sq ft

721 S Woodland St, Winter Garden, FL 34787

Property at 20 E Division St, Winter Garden, FL 34787, 4 beds, 3 baths

$1,080,000

4 beds3 baths2,729 sq ft

20 E Division St, Winter Garden, FL 34787

Property at 17134 Lake Ingram Rd, Winter Garden, FL 34787, 4 beds, 2 baths

$625,000

4 beds2 baths1,924 sq ft

17134 Lake Ingram Rd, Winter Garden, FL 34787

Property at 721 Foster Ave, Winter Garden, FL 34787, 7 beds, 3 baths

$699,000

7 beds3 baths2,293 sq ft

721 Foster Ave, Winter Garden, FL 34787

Property at 15992 W Colonial Dr, Oakland, FL 34787, 41 beds, 75 baths

$3,200,000

41 beds75 baths17,021 sq ft

15992 W Colonial Dr, Oakland, FL 34787

Property at 634 Foster Ave, Winter Garden, FL 34787, 2 beds, 1 bath

$285,000

2 beds1 bath696 sq ft

634 Foster Ave, Winter Garden, FL 34787

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

$342,000

2 beds1 bath914 sq ft

636 Coke Ave, Winter Garden, FL 34787

Property at 205 Surprise Dr, Winter Garden, FL 34787, 4 beds, 2.5 baths

$1,200,000

4 beds2.5 baths2,171 sq ft

205 Surprise Dr, Winter Garden, FL 34787

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW 12 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Short Sale. SHORT SALE – SUBJECT TO THIRD-PARTY/LENDER APPROVAL. Beautifully updated 3-bedroom, 2-bath home renovated in 2023 with NO HOA! Situated on a spacious lot surrounded by mature trees, offering privacy and peaceful greenery views. The interior features ceramic tile flooring throughout, contemporary finishes, and an updated kitchen with quartz and granite countertops, wood cabinetry, and newer appliances that convey. Conveniently located in Apopka, just minutes from Lake Apopka, shopping, dining, and major roadways. Move-in ready and sold AS-IS. All offers and terms are subject to lender approval.

$270,000

3 beds2 baths1,188 sq ft

2350 Valley Dr, Apopka, FL 32703

Newer appliances • Greenery views • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Virtually Staged. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedicated boat dock, the property captures sweeping views across Wauseon Bay. The current home is in good condition and ready to move in. The interior showcases a refined yet comfortable cabin style with some modern flair and a open-concept layout, four bedrooms and thoughtfully updated living spaces. A beautifully appointed kitchen features custom cabinetry, quartz surfaces, and premium appliances, while restored hardwood flooring adds timeless character throughout. The primary s

$1,650,000

4 beds2 baths2,627 sq ft

212 W 1st Ave, Windermere, FL 34786

Custom cabinetry • Dedicated boat dock • Quartz surfaces

OPEN SAT, 11AM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
MONTVERDE LAKEFRONT HOME WITH DIRECT ACCESS TO PRIVATE LAKE FLORENCE! Bring your ideas and make this charming 2-bedroom, 2-bath lakefront home your own with some updates, or simply enjoy it as it is. Offering over 1,300 heated square feet, this home provides a comfortable layout with plenty of opportunity to add your own personal style and make it truly special. The cute kitchen is conveniently located just off the family room, creating a cozy gathering space for everyday living. A wood-burning fireplace adds warmth and character and is perfect for those cooler Florida evenings. The home also features a nice-sized indoor laundry room and a convenient two-car garage. Step out back to the con

$625,000

2 beds2 baths1,351 sq ft

17561 County Road 455, Montverde, FL 34756

Direct lakefrontage • Concrete patio • Indoor laundry room

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Welcome to this beautifully remodeled 3-bedroom, 2-bath home offering 1,368 square feet of stylish, move-in-ready living in the heart of Apopka! Every detail has been thoughtfully updated, blending modern finishes with everyday comfort. Major improvements include a 2022 roof and a water softener system, providing added value and peace of mind. Step inside to discover bright, inviting living spaces, an updated kitchen, renovated bathrooms, and a functional floor plan perfect for first-time homebuyers, downsizers, or investors. Conveniently located just minutes from shopping, dining, parks, and major roadways, you'll enjoy easy access to everyday essentials, including Winn-Dixie, ALDI, and Ap

$299,900

4 beds2 baths1,368 sq ft

3625 Cochran St, Apopka, FL 32703

Nearby magnolia park • Renovated bathrooms • Updated kitchen

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Virtually Staged. * * SANDY SHORES SANCTUARY * * A rare 1934 Windermere Landmark on the Butler Chain of Lakes. Rich in history and timeless charm, this one-of-a-kind canal-front home offers a rare opportunity to own a piece of Old Windermere. Privately nestled beneath a canopy of oak trees in the exclusive Sandy Shores enclave, one of Windermere's most private waterfront communities, this 5-bedroom, 3-bath residence offers direct canal access to Lake Butler. Blending historic charm with modern comfort, the home has been thoughtfully updated with a remodeled kitchen and bathrooms, 2024 HVAC systems, a 2017 roof, 2021 & 2017 water heaters, a 2020 septic drain field, and a 2026 well t

$1,275,000

5 beds3 baths2,831 sq ft

12085 Sandy Shores Dr, Windermere, FL 34786

Waterfront deck • Screened in porch • Canal front home

ABOUT THIS HOME
Vintage Home for sale in 34787, FL:
Wake up to the sunrise over one of Central Florida's most sought-after private lakes. This beautifully renovated lakefront cottage offers the rare opportunity to enjoy an exceptional waterfront lifestyle while owning a property with a proven history as a successful vacation rental. Whether you're looking for a weekend escape, full-time residence, or investment property, this home delivers the best of all three. Why You'll Love It: • 43 feet of private lake frontage on one of Florida's premier quality watersport lakes. • Private dock with covered boat lift—launch directly into some of the best skiing, wakeboarding, paddle boarding, fishing and sunset cruises in Central Florid

$569,000

2 beds1 bath900 sq ft

16533 Lowry Rd, Montverde, FL 34756

Lake frontage • Lakefront lifestyle • Screened in deck

Property at 650 S Lakewood Ave, Ocoee, FL 34761, 3 beds, 3 baths

$279,000

3 beds3 baths1,490 sq ft

650 S Lakewood Ave, Ocoee, FL 34761

Property at 1825 Demastus Ln, Ocoee, FL 34761, 3 beds, 2.5 baths

$949,000

3 beds2.5 baths2,360 sq ft

1825 Demastus Ln, Ocoee, FL 34761

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

$3,999,999

5 beds7 baths6,248 sq ft

11002 Lake Butler Blvd, Windermere, FL 34786

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

Based on information submitted to the MLS GRID as of Wed Aug 19 2026. 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 34787

There are currently 13 vintage homes for sale in 34787 at a median listing price of $594K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 34787 stay on the market for 71 days and receive 1 offers. This map is refreshed with the newest listings in 34787 every 15 minutes.

In the past month, 181 homes have been sold in 34787. In addition to houses in 34787, there were also 135 condos, 140 townhouses, and 5 multi-family units for sale in 34787 last month. Find your dream home in 34787 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 34787 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 34787. If you're looking to sell your home in the 34787 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 34787 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for 34787, FL

Nearby Zip Codes

Cities

Nearby Zip Codes with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in 34787, FL

How to buy a house in 34787, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

8 Redfin agents serving 34787

162

Deals*

4.8

Satisfaction

1365

Homes closed*

* Data from the last year

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.