Vintage homes for sale & real estate in Orange County, FL

564 homes + 1 early access

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
TWO HOMES ON ONE LOT – GREAT INVESTMENT OPPORTUNITY Unique property featuring two separate homes on the same lot, each with its own independent address and completely separate utilities. Main House * 3 bedrooms * 1 full bathroom * Kitchen * Living space * Independent address * Separate utilities Second House * 2 bedrooms * 1 full bathroom * Kitchen * Living space * Independent address * Separate utilities The two homes provide separate living spaces and are ideal for an extended family, multi-generational living, or rental income. OPTIONAL MOBILE HOME – $6,000 ADDITIONAL The property also includes a mobile home/RV that can be p

$390,000

3 beds1 bath2,160 sq ft

793 Eldridge St, Orlando, FL 32803

Separate utilities • Two separate homes • Independent address

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Exceptional builder and investor opportunity in a desirable location! This property offers a rare combination of an existing single-family residence and functional in-ground pool situated on an oversized lot with multiple potential redevelopment strategies. The existing home is in need of significant renovation and may provide an opportunity for a buyer to reimagine the structure as a potential duplex, subject to zoning and governmental approvals, or pursue a tear-down and explore the potential to divide the lot into two buildable parcels. The functional in-ground pool adds additional value and flexibility for a renovation-minded buyer or could potentially be incorporated into a future deve

$450,000

3 beds2 baths1,301 sq ft

5034 Old Cheney Hwy, Orlando, FL 32807

In-ground pool • Buildable parcels • Oversized lot

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Opportunity is knocking at 914 W South Street, Orlando, FL 32805! This property is more than just a 2-bedroom, 1-bath home it also includes an adjacent vacant lot, giving investors, builders, and buyers the chance to maximize the value of one purchase. The existing home offers renovation, rental, or resale potential, while the neighboring lot opens the door for possible new construction or future development. No impact fee, potentially creating additional savings for the next owner. Located just minutes from Camping World Stadium, Downtown Orlando, major highways, dining, entertainment, and employment centers, this location offers convenient access to everything Central Orlando has to enjoy

$350,000

2 beds1 bath720 sq ft

914 W South St, Orlando, FL 32805

Rental potential • Future development • New construction

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Welcome to this beautifully renovated bungalow in the heart of Orlando, tucked away near Lake Walker. Built in the mid-1950s with solid block construction, this charming home combines classic character with modern updates and a comfortable open floor plan. Step inside to a freshly painted interior featuring luxury vinyl flooring throughout. The open kitchen and living area is perfect for everyday living and entertaining, with quartz countertops, a breakfast bar, stainless steel appliances, and plenty of cabinet space. A bright dining area provides the perfect place to enjoy meals with family and friends. The two spacious bedrooms with plenty of room for larger bedroom furniture. The updated

$285,000

2 beds1 bath810 sq ft

3612 Wells St, Orlando, FL 32805

Quartz countertops • Renovated bungalow • Breakfast bar

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS P

$3,950,000

4 beds2 baths1,652 sq ft

540 N Pennsylvania Ave, Winter Park, FL 32789

R-3 zoned • 0.45 acre lot • Parking

Property at 1239 19th St, Orlando, FL 32805, 7 beds, 4 baths

$699,000

7 beds4 baths2,356 sq ft

1239 19th St, Orlando, FL 32805

Property at 8506 Dot Ln, Orlando, FL 32809, 3 beds, 2 baths

$250,000

3 beds2 baths1,325 sq ft

8506 Dot Ln, Orlando, FL 32809

Property at 5119 Divot Ct, Orlando, FL 32808, 4 beds, 2 baths

$277,000

4 beds2 baths1,193 sq ft

5119 Divot Ct, Orlando, FL 32808

Property at 1216 Golden Ln, Orlando, FL 32804, 3 beds, 2 baths

$749,000

3 beds2 baths2,168 sq ft

1216 Golden Ln, Orlando, FL 32804

Property at 2227 Howard Dr, Winter Park, FL 32789, 3 beds, 2.5 baths

$1,100,000

3 beds2.5 baths2,196 sq ft

2227 Howard Dr, Winter Park, FL 32789

Property at 5501 Perrine Dr, Orlando, FL 32808, 3 beds, 2 baths

$236,900

3 beds2 baths1,614 sq ft

5501 Perrine Dr, Orlando, FL 32808

Property at 1115 N Powers Dr, Orlando, FL 32818, 4 beds, 2 baths

$306,910

4 beds2 baths1,495 sq ft

1115 N Powers Dr, Orlando, FL 32818

Property at 1401 Yates St, Orlando, FL 32804, 2 beds, 1 bath

$5,000

2 beds1 bath924 sq ft

1401 Yates St, Orlando, FL 32804

Property at 1812 Janice Ave, Orlando, FL 32803, 2 beds, 1 bath

$383,000

2 beds1 bath945 sq ft

1812 Janice Ave, Orlando, FL 32803

Property at 2620 Marble Ave, Orlando, FL 32803, 3 beds, 3 baths

$679,000

3 beds3 baths1,664 sq ft

2620 Marble Ave, Orlando, FL 32803

Property at 1221 Dorchester St, Orlando, FL 32803, 6 beds, 5.5 baths

$2,295,000

6 beds5.5 baths3,781 sq ft

1221 Dorchester St, Orlando, FL 32803

Property at 3101 Flowertree Rd, Belle Isle, FL 32812, 4 beds, 3 baths

$527,500

4 beds3 baths1,680 sq ft

3101 Flowertree Rd, Belle Isle, FL 32812

Property at 5518 Riviera Dr, Orlando, FL 32808, 3 beds, 2 baths

$260,000

3 beds2 baths1,276 sq ft

5518 Riviera Dr, Orlando, FL 32808

Property at 1212 Elmwood St, Orlando, FL 32801, 4 beds, 3 baths

$715,000

4 beds3 baths2,116 sq ft

1212 Elmwood St, Orlando, FL 32801

Property at 5423 Ashmeade Rd, Orlando, FL 32810, 4 beds, 2.5 baths

$230,000

4 beds2.5 baths2,180 sq ft

5423 Ashmeade Rd, Orlando, FL 32810

Property at 2102 Harrison Ave, Orlando, FL 32804, 5 beds, 2.5 baths

$749,900

5 beds2.5 baths1,776 sq ft

2102 Harrison Ave, Orlando, FL 32804

Property at 5609 Perrine Dr, Orlando, FL 32808, 4 beds, 2 baths

$265,000

4 beds2 baths1,718 sq ft

5609 Perrine Dr, Orlando, FL 32808

Property at 611 Butler St, Windermere, FL 34786, 3 beds, 2 baths

$775,000

3 beds2 baths1,774 sq ft

611 Butler St, Windermere, FL 34786

Property at 46 E Princeton St, Orlando, FL 32804, 4 beds, 3 baths

$575,000

4 beds3 baths2,016 sq ft

46 E Princeton St, Orlando, FL 32804

Property at 2333 Westminster Ct, Winter Park, FL 32789, 4 beds, 2 baths

$649,900

4 beds2 baths1,877 sq ft

2333 Westminster Ct, Winter Park, FL 32789

Property at 3942 Wells St N, Orlando, FL 32805, 3 beds, 2 baths

$279,000

3 beds2 baths1,110 sq ft

3942 Wells St N, Orlando, FL 32805

Property at 204 Garden Ave, Orlando, FL 32805, 3 beds, 2 baths

$249,999

3 beds2 baths1,040 sq ft

204 Garden Ave, Orlando, FL 32805

Property at 628 Forest St, Windermere, FL 34786, 1 bed, 1 bath

$700,000

1 bed1 bath750 sq ft

628 Forest St, Windermere, FL 34786

Property at 1031 Waltham Ave, Orlando, FL 32809, 3 beds, 2 baths

$400,000

3 beds2 baths1,210 sq ft

1031 Waltham Ave, Orlando, FL 32809

Property at 2821 W Amelia St, Orlando, FL 32805, 3 beds, 2 baths

$289,900

3 beds2 baths1,109 sq ft

2821 W Amelia St, Orlando, FL 32805

Property at 1202 Oranole Rd, Maitland, FL 32751, 3 beds, 2 baths

$404,800

3 beds2 baths1,750 sq ft

1202 Oranole Rd, Maitland, FL 32751

Property at 1627 E Concord St, Orlando, FL 32803, 4 beds, 2 baths

$560,000

4 beds2 baths1,524 sq ft

1627 E Concord St, Orlando, FL 32803

Property at 508 Brechin Dr, Winter Park, FL 32792, 3 beds, 2 baths

$629,000

3 beds2 baths1,783 sq ft

508 Brechin Dr, Winter Park, FL 32792

Property at 120 Primrose Ct, Orlando, FL 32803, 3 beds, 3 baths

$438,000

3 beds3 baths1,520 sq ft

120 Primrose Ct, Orlando, FL 32803

Property at 1017 N Glenwood Ave, Orlando, FL 32803, 3 beds, 2 baths

$485,000

3 beds2 baths1,248 sq ft

1017 N Glenwood Ave, Orlando, FL 32803

Property at 3120 Tradewinds Trl, Orlando, FL 32805, 4 beds, 2 baths

$385,000

4 beds2 baths1,737 sq ft

3120 Tradewinds Trl, Orlando, FL 32805

Property at 471 Holt Ave, Winter Park, FL 32789, 4 beds, 3 baths

$975,000

4 beds3 baths2,528 sq ft

471 Holt Ave, Winter Park, FL 32789

Property at 128 Wisteria Ave, Orlando, FL 32806, 4 beds, 3.5 baths

$849,900

4 beds3.5 baths2,346 sq ft

128 Wisteria Ave, Orlando, FL 32806

Property at 7719 Udine Ave, Orlando, FL 32819, 3 beds, 2 baths

$275,000

3 beds2 baths1,014 sq ft

7719 Udine Ave, Orlando, FL 32819

Property at 1601 Bryn Mawr St, Orlando, FL 32804, 2 beds, 2 baths

$425,000

2 beds2 baths1,215 sq ft

1601 Bryn Mawr St, Orlando, FL 32804

Property at 900 Carver St, Winter Park, FL 32789, 3 beds, 3 baths

$689,000

3 beds3 baths1,794 sq ft

900 Carver St, Winter Park, FL 32789

Viewing page 2 of 14

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of Georgia MLS. Real estate listings held by brokerage firms other than Redfin are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers. Information deemed reliable but not guaranteed. Copyright 2026 Georgia MLS. All rights reserved.

Based on information submitted to the MLS GRID as of Mon Sep 21 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 Orange County

There are currently 565 vintage homes for sale in Orange County at a median listing price of $435K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Orange County stay on the market for 76 days and receive 2 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 1359 homes have been sold in Orange County. In addition to houses in Orange County, there were also 1895 condos, 1047 townhouses, and 59 multi-family units for sale in Orange County last month. Find your dream home in Orange County 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 Orange County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Orange County. If you're looking to sell your home in the Orange County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Orange County 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 Orange County, FL

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Orange County, FL

How to buy a house in Orange County, 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

16 Redfin agents serving Orange County

340

Deals*

4.8

Satisfaction

2129

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.