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

606 homes + 1 early access

Sort:

Recommended

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can walk to highly rated Brookshire Elem and Winter Park High. The open-plan living space has beautiful travertine tile floors flowing through the kitchen, dining room, and living room. Renovated in 2026, the kitchen offers quartz counter tops, new appliances, under cabinet lighting, custom tile backsplash, and pendant lights. Flowing from the kitchen to the dining room and through to the living room, this open floor plan is sure to please. Double French doors open from the sunny living room to the spacious backyard. The oversi

$675,000

4 beds2 baths1,509 sq ft

2260 Coldstream Dr, Winter Park, FL 32792

Tree lined street • Renovated kitchen • Quartz counter tops

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Welcome to 1740 S Rio Grande Ave, a 3-bedroom, 1-bath home offering an excellent opportunity to renovate, personalize, or add to your investment portfolio. The home is currently in livable condition and features a functional floor plan with all three bedrooms under air and included within the home’s original city-recognized under-air square footage. The property is ready for its next owner to bring their vision and make cosmetic improvements to unlock its full potential. Conveniently located near Downtown Orlando, Camping World Stadium, shopping, dining, major roadways, and public transportation, providing easy access throughout the Orlando area. Whether you're looking for your next r

$210,000

3 beds1 bath962 sq ft

1740 S Rio Grande Ave, Orlando, FL 32805

Easy access • Livable condition • Conveniently located

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
RARE FIND! Fully Renovated Home with Private In-Law Suite + Separate Entrance! Beautifully renovated throughout, this 4-bedroom, 3-bathroom residence offers 1,683 SF of versatile living space in Orlando’s highly desirable 32806 ZIP code. The standout feature is the fully independent private in-law suite, complete with its own full bathroom and separate entrance. Ideal for an in-law suite, guest quarters, private office, studio, or flexible living space. The main home features 3 bright bedrooms and 2 fully updated bathrooms, complemented by an open-concept layout and modern finishes throughout. The completely renovated kitchen features quartz countertops, stainless steel appliances,

$434,990

4 beds3 baths1,683 sq ft

3338 Ontario Ave, Orlando, FL 32806

Private in-law suite • Generous corner lot • No hoa fees

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
NEW PRICE – $459,999! Take another look at this charming Orlando home in the heart of desirable Ivanhoe Village. Built in 1944 and nestled along a picturesque brick-lined street, this distinctive 2-bedroom, 1-bath home offers 1,337 square feet filled with vintage character, personality, and possibility. Step inside and discover a whimsical French-inspired aesthetic featuring crystal chandeliers, warm wood floors, and abundant natural light. The combined living and dining area creates an inviting space for gatherings, while a separate family room offers a comfortable retreat. The kitchen features bright cabinetry, granite countertops, a gas range, and a dedicated laundry room. Step out

$459,999

2 beds1 bath1,337 sq ft

1619 New York Ave, Orlando, FL 32803

Covered paver patio • No hoa • 3,964 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Unique opportunity in historic Eatonville! Situated on approximately 0.29 acres at the corner of Lemon Street and Moseley Avenue, this distinctive property combines C-3 commercial zoning, two existing structures and frontage along two streets—creating an exciting opportunity for the buyer with vision. One residence is currently tenant occupied, offering an existing improvement while future possibilities are explored. The property encompasses historic Lots 5 and 6 of Calhoun's Subdivision and offers a versatile setting that may appeal to investors, entrepreneurs, developers or owner-users. Imagine the possibilities for this highly visible corner—from a future commercial concept o

$525,000

4 beds2 baths1,012 sq ft

307 Lemon St, Maitland, FL 32751

Existing improvement • 0.29 acre lot • 2 parking spots

Property at 3519 Calumet Dr, Orlando, FL 32810, 4 beds, 2 baths

$299,900

4 beds2 baths1,532 sq ft

3519 Calumet Dr, Orlando, FL 32810

Property at 208 Palmyra Dr, Orlando, FL 32807, 3 beds, 2 baths

$340,000

3 beds2 baths1,252 sq ft

208 Palmyra Dr, Orlando, FL 32807

Property at 813 Greenwood St, Orlando, FL 32801, 7 beds, 5 baths

$799,000

7 beds5 baths3,547 sq ft

813 Greenwood St, Orlando, FL 32801

Property at 5701 Padgett Cir, Orlando, FL 32839, 3 beds, 2 baths

$465,000

3 beds2 baths1,772 sq ft

5701 Padgett Cir, Orlando, FL 32839

Property at 7008 Tripoli Way, Orlando, FL 32822, 4 beds, 2 baths

$314,000

4 beds2 baths1,114 sq ft

7008 Tripoli Way, Orlando, FL 32822

Property at 5847 Harrington Dr, Orlando, FL 32808, 4 beds, 3 baths

$276,500

4 beds3 baths1,582 sq ft

5847 Harrington Dr, Orlando, FL 32808

Property at 804 W Concord St, Orlando, FL 32805, 5 beds, 5 baths

$1,049,000

5 beds5 baths3,686 sq ft

804 W Concord St, Orlando, FL 32805

Property at 1227 N Pine Hills Rd, Orlando, FL 32808, 2 beds, 1 bath

$199,900

2 beds1 bath1,220 sq ft

1227 N Pine Hills Rd, Orlando, FL 32808

Property at 8126 Castinango St, Orlando, FL 32817, 3 beds, 2 baths

$349,900

3 beds2 baths1,497 sq ft

8126 Castinango St, Orlando, FL 32817

Property at 3615 S Summerlin Ave, Orlando, FL 32806, 3 beds, 2 baths

$424,900

3 beds2 baths1,374 sq ft

3615 S Summerlin Ave, Orlando, FL 32806

Property at 2112 Vivada St, Orlando, FL 32803, 3 beds, 2 baths

$425,000

3 beds2 baths1,100 sq ft

2112 Vivada St, Orlando, FL 32803

Property at 1652 Berkshire Ave, Winter Park, FL 32789, 3 beds, 2 baths

$429,000

3 beds2 baths1,498 sq ft

1652 Berkshire Ave, Winter Park, FL 32789

Property at 4511 Longworth Dr, Orlando, FL 32812, 5 beds, 3 baths

$550,000

5 beds3 baths2,771 sq ft

4511 Longworth Dr, Orlando, FL 32812

Property at 3410 Calumet Dr, Orlando, FL 32810, 4 beds, 3 baths

$350,000

4 beds3 baths1,660 sq ft

3410 Calumet Dr, Orlando, FL 32810

Property at 1602 Overlook Rd, Belle Isle, FL 32809, 3 beds, 2 baths

$449,900

3 beds2 baths985 sq ft

1602 Overlook Rd, Belle Isle, FL 32809

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 113 Hope Cir, Orlando, FL 32811, 3 beds, 2 baths

$278,900

3 beds2 baths988 sq ft

113 Hope Cir, Orlando, FL 32811

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

$724,900

5 beds2.5 baths1,776 sq ft

2102 Harrison Ave, Orlando, FL 32804

Property at 1232 E Livingston St, Orlando, FL 32803, 3 beds, 2 baths

$565,000

3 beds2 baths1,566 sq ft

1232 E Livingston St, Orlando, FL 32803

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 1710 Oregon St, Orlando, FL 32803, 4 beds, 2.5 baths

$689,900

4 beds2.5 baths2,444 sq ft

1710 Oregon St, Orlando, FL 32803

Property at 701 23rd St, Orlando, FL 32805, 3 beds, 2 baths

$300,000

3 beds2 baths1,100 sq ft

701 23rd St, Orlando, FL 32805

Property at 1910 Curry Ford Rd, Orlando, FL 32806, 3 beds, 2 baths

$419,000

3 beds2 baths1,344 sq ft

1910 Curry Ford Rd, Orlando, FL 32806

Property at 113 W Division St, Winter Garden, FL 34787, 4 beds, 2 baths

$455,000

4 beds2 baths1,487 sq ft

113 W Division St, Winter Garden, FL 34787

Property at 4114 E Michigan St, Orlando, FL 32812, 4 beds, 4 baths

$475,000

4 beds4 baths1,993 sq ft

4114 E Michigan St, Orlando, FL 32812

Property at 311 E Morse Blvd Unit 4-5, Winter Park, FL 32789, 2 beds, 2 baths

$895,000

2 beds2 baths1,763 sq ft

311 E Morse Blvd Unit 4-5, Winter Park, FL 32789

Property at 610 Sweetbriar Rd, Orlando, FL 32806, 3 beds, 2 baths

$535,000

3 beds2 baths1,717 sq ft

610 Sweetbriar Rd, Orlando, FL 32806

Property at 2829 Lake Margaret Dr, Orlando, FL 32806, 3 beds, 2 baths

$395,000

3 beds2 baths1,247 sq ft

2829 Lake Margaret Dr, Orlando, FL 32806

Property at 731 W Princeton St, Orlando, FL 32804, 2 beds, 1 bath

$369,900

2 beds1 bath783 sq ft

731 W Princeton St, Orlando, FL 32804

Property at 3202 Tradewinds Trl, Orlando, FL 32805, 3 beds, 3 baths

$419,900

3 beds3 baths1,667 sq ft

3202 Tradewinds Trl, Orlando, FL 32805

Property at 914 26th St, Orlando, FL 32805, 2 beds, 1 bath

$184,500

2 beds1 bath748 sq ft

914 26th St, Orlando, FL 32805

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

$369,000

4 beds2 baths1,737 sq ft

3120 Tradewinds Trl, Orlando, FL 32805

Property at 6401 Ramir Rd, Orlando, FL 32810, 3 beds, 2 baths

$315,000

3 beds2 baths1,497 sq ft

6401 Ramir Rd, Orlando, FL 32810

Property at 6610 Bywood Dr, Orlando, FL 32810, 3 beds, 1 bath

$240,000

3 beds1 bath960 sq ft

6610 Bywood Dr, Orlando, FL 32810

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

$609,000

3 beds2 baths1,783 sq ft

508 Brechin Dr, Winter Park, FL 32792

Property at 816 E Jefferson St, Orlando, FL 32801, 3 beds, 2 baths

$430,000

3 beds2 baths1,138 sq ft

816 E Jefferson St, Orlando, FL 32801

Viewing page 6 of 15

Based on information submitted to the MLS GRID as of Wed Oct 28 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 607 vintage homes for sale in Orange County at a median listing price of $430K. 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 79 days and receive 1 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 1292 homes have been sold in Orange County. In addition to houses in Orange County, there were also 1907 condos, 1018 townhouses, and 63 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

14 Redfin agents serving Orange County

298

Deals*

4.8

Satisfaction

1830

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.