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

514 homes

Sort:

Recommended

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
One or more photo(s) has been virtually staged. Completely remodeled 4-bedroom home in the heart of College Park! This Mid-Century Modern gem has been fully updated from top to bottom, featuring a new permitted roof, new HVAC, updated plumbing and electrical, new energy-efficient water heater, stainless steel appliances, soft-close cabinets, a large kitchen island, fresh landscaping, and more. Every detail has been thoughtfully designed for comfort, efficiency, and style. Step inside to discover a Modern Contemporary interior with an open-concept layout, luxury vinyl plank flooring, fresh interior and exterior paint, and designer lighting throughout. The chef’s kitchen boasts quart

$569,990

4 beds2 baths1,893 sq ft

1429 Yates St, Orlando, FL 32804

Updated electrical • New hvac • New permitted roof

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Classic Craftsman charm meets modern comfort in this beautifully updated 3-bedroom, 3-bath home in the heart of Thornton Park, just steps from all downtown Orlando has to offer. A welcoming front porch with a bold red door and views of majestic oak trees set the tone for the warm, inviting interiors. Inside, light-filled living spaces feature rich hardwood floors, crown molding, built-in storage, and a striking updated fireplace. The stylish kitchen blends timeless character with modern convenience, offering a farmhouse sink, granite counters, stainless steel appliances, and a brand-new tankless water heater. The spacious primary suite includes a spa shower, huge walk-in closet, and gorgeou

$685,000

3 beds2.5 baths2,103 sq ft

705 E Pine St, Orlando, FL 32801

Updated fireplace • Huge walk-in closet • Spa shower

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Welcome to this stunning home in Coytown, one of Orlando’s most desirable established neighborhoods just east of Colonialtown and minutes from Mills 50, Winter Park, Leu Gardens, Baldwin Park, and Audubon Park. Zoned for Audubon Park K-8 School and Winter Park High School. This solid block home with crawl-space construction seamlessly blends timeless mid-century character with a designer-curated modern renovation completed in Summer 2025. Reimagined by an interior designer, the home showcases very chic, cohesive finishes throughout: crisp white walls, warm wood tones, brushed gold accents, and curated lighting that creates a refined yet inviting atmosphere. The open-concept layout

$555,000

3 beds2 baths1,263 sq ft

2639 Betty St, Orlando, FL 32803

Quartz countertops • Updated bathrooms • Brand-new kitchen

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
LOCATED IN THE WASHINGTON SHORES AREA. HOUSE IS A 3 BEDROOM/2 BATHROOMS WITH 1,128 SQFT. LOCATED CLOSE TO SCHOOLS, SHOPS, RESTURANTS, AND MAIN HIGHWAYS. ROOF IS FROM 2018. NEW FLOORING, PAINT AND KITCHEN CABINETS WITH GRANITE COUNTER-TOPS. CALL WITH ANY QUESTIONS.

$250,000

3 beds2 baths1,128 sq ft

830 Wooden Blvd, Orlando, FL 32805

Close to schools • New flooring • Kitchen cabinets

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
This home PAYS FOR ITSELF * details in the description. Discover timeless elegance in this beautiful 4-bedroom, 3.5+ bathroom historic property nestled in the sought-after Lake Cherokee neighborhood on the same block as infamous Honeymoon Row. This property has stories to tell and has been in the spotlight too—it was featured in printed publications and two TV commercials! A main house with original details from 1911 showcases 3 beds/2.5 baths plus Florida room over 3 stories, an updated open floor plan, upgraded metal roof & modernized HVAC, windows, electrical, and plumbing. The kitchen is a stunner, featuring quartz countertops, a gas range with leather vent hood, stainless

$1,395,000

4 beds4 baths3,326 sq ft

515 Lake Ave, Orlando, FL 32801

Custom cabinetry • Quartz countertops • Historic property

Property at 915 W Princeton St, Orlando, FL 32804, 4 beds, 1.5 baths

$410,000

4 beds1.5 baths1,280 sq ft

915 W Princeton St, Orlando, FL 32804

Property at 1725 Fairview Shores Dr, Orlando, FL 32804

$2,250,000

0 beds— baths16,191 sq ft

1725 Fairview Shores Dr, Orlando, FL 32804

Property at 225 E New Hampshire St #6, Orlando, FL 32804, 2 beds, 1 bath

$199,998

2 beds1 bath572 sq ft

225 E New Hampshire St #6, Orlando, FL 32804

Property at 6157 Medford Dr, Orlando, FL 32808, 3 beds, 2 baths

$365,000

3 beds2 baths1,797 sq ft

6157 Medford Dr, Orlando, FL 32808

Property at 8314 Calais Cir, Orlando, FL 32825, 3 beds, 2 baths

$317,750

3 beds2 baths1,212 sq ft

8314 Calais Cir, Orlando, FL 32825

Property at 508 Topaz Way, Orlando, FL 32806, 4 beds, 2 baths

$399,900

4 beds2 baths1,556 sq ft

508 Topaz Way, Orlando, FL 32806

Property at 843 Palm Dr, Orlando, FL 32803, 3 beds, 2 baths

$475,000

3 beds2 baths1,170 sq ft

843 Palm Dr, Orlando, FL 32803

Property at 225 E New Hampshire St #10, Orlando, FL 32804, 2 beds, 1 bath

$199,998

2 beds1 bath572 sq ft

225 E New Hampshire St #10, Orlando, FL 32804

Property at 4490 Simmons Rd, Orlando, FL 32812, 2 beds, 2 baths

$319,000

2 beds2 baths1,334 sq ft

4490 Simmons Rd, Orlando, FL 32812

Property at 727 Park Lake Cir, Orlando, FL 32803, 5 beds, 4.5 baths

$1,469,100

5 beds4.5 baths3,046 sq ft

727 Park Lake Cir, Orlando, FL 32803

Property at 417 N Tampa Ave, Orlando, FL 32805, 4 beds, 2.5 baths

$350,000

4 beds2.5 baths1,715 sq ft

417 N Tampa Ave, Orlando, FL 32805

Property at 6021 Yucatan Dr, Orlando, FL 32807, 2 beds, 1 bath

$285,000

2 beds1 bath766 sq ft

6021 Yucatan Dr, Orlando, FL 32807

Property at 2600 Reef Ct, Orlando, FL 32805, 3 beds, 2 baths

$499,000

3 beds2 baths2,504 sq ft

2600 Reef Ct, Orlando, FL 32805

Property at 3223 N Orange Ave, Orlando, FL 32803, 3 beds, 2 baths

$625,000

3 beds2 baths1,882 sq ft

3223 N Orange Ave, Orlando, FL 32803

Property at 79 W Harding St, Orlando, FL 32806, 2 beds, 1 bath

$410,000

2 beds1 bath1,031 sq ft

79 W Harding St, Orlando, FL 32806

Property at 6103 Bolling Dr, Orlando, FL 32808, 3 beds, 1 bath

$195,000

3 beds1 bath965 sq ft

6103 Bolling Dr, Orlando, FL 32808

Property at 1144 Palma Dr, Orlando, FL 32805, 3 beds, 2 baths

$549,999

3 beds2 baths1,760 sq ft

1144 Palma Dr, Orlando, FL 32805

Property at 912 Bradshaw Ter, Orlando, FL 32806, 3 beds, 1 bath

$324,500

3 beds1 bath974 sq ft

912 Bradshaw Ter, Orlando, FL 32806

Property at 346 Hillman Ave, Orlando, FL 32803, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths2,983 sq ft

346 Hillman Ave, Orlando, FL 32803

Property at 2500 Nancy St, Orlando, FL 32806, 4 beds, 3.5 baths

$630,000

4 beds3.5 baths2,170 sq ft

2500 Nancy St, Orlando, FL 32806

Property at 1104 Kasper Dr, Orlando, FL 32806, 3 beds, 2 baths

$569,000

3 beds2 baths1,537 sq ft

1104 Kasper Dr, Orlando, FL 32806

Property at 38 E Yale St, Orlando, FL 32804, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths2,307 sq ft

38 E Yale St, Orlando, FL 32804

Property at 225 E New Hampshire St #14, Orlando, FL 32804, 2 beds, 1 bath

$199,998

2 beds1 bath572 sq ft

225 E New Hampshire St #14, Orlando, FL 32804

Property at 812 E Harwood St, Orlando, FL 32803, 4 beds, 3 baths

$649,900

4 beds3 baths2,163 sq ft

812 E Harwood St, Orlando, FL 32803

Property at 940 Alba Dr, Orlando, FL 32804, 4 beds, 3 baths

$799,900

4 beds3 baths2,470 sq ft

940 Alba Dr, Orlando, FL 32804

Property at 213 Phillips Pl, Orlando, FL 32806, 3 beds, 2.5 baths

$988,000

3 beds2.5 baths2,927 sq ft

213 Phillips Pl, Orlando, FL 32806

Property at 4309 S Rio Grande Ave, Orlando, FL 32839, 2 beds, 1 bath

$220,000

2 beds1 bath1,188 sq ft

4309 S Rio Grande Ave, Orlando, FL 32839

Property at 10 S Semoran Blvd, Orlando, FL 32807, 3 beds, 2 baths

$895,000

3 beds2 baths1,498 sq ft

10 S Semoran Blvd, Orlando, FL 32807

Property at 1400 Shady Lane Dr, Orlando, FL 32804, 2 beds, 1 bath

$339,500

2 beds1 bath768 sq ft

1400 Shady Lane Dr, Orlando, FL 32804

Property at 500 Mary Jess Rd, Orlando, FL 32839, 3 beds, 2 baths

$299,990

3 beds2 baths1,402 sq ft

500 Mary Jess Rd, Orlando, FL 32839

Property at 823 E Amelia St, Orlando, FL 32803, 3 beds, 3 baths

$625,000

3 beds3 baths1,838 sq ft

823 E Amelia St, Orlando, FL 32803

Property at 740 Baffie Ave, Winter Park, FL 32789, 3 beds, 2 baths

$445,000

3 beds2 baths1,456 sq ft

740 Baffie Ave, Winter Park, FL 32789

Property at 1007 Early Ave, Winter Park, FL 32789, 3 beds, 2 baths

$425,000

3 beds2 baths1,721 sq ft

1007 Early Ave, Winter Park, FL 32789

Property at 241 N Dillard St, Winter Garden, FL 34787, 3 beds, 2.5 baths

$1,800,000

3 beds2.5 baths3,507 sq ft

241 N Dillard St, Winter Garden, FL 34787

Property at 259 Blossom Ln, Winter Park, FL 32789, 3 beds, 2 baths

$499,000

3 beds2 baths1,354 sq ft

259 Blossom Ln, Winter Park, FL 32789

Property at 915 Garden Dr, Winter Park, FL 32789, 3 beds, 3 baths

$900,000

3 beds3 baths2,456 sq ft

915 Garden Dr, Winter Park, FL 32789

Viewing page 5 of 9

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 2025 Georgia MLS. All rights reserved.

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 Orange County

There are currently 514 vintage homes for sale in Orange County at a median listing price of $434K. 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 85 days and receive 1 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 1321 homes have been sold in Orange County. In addition to houses in Orange County, there were also 1892 condos, 949 townhouses, and 43 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

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

Why Redfin?

Community Impact

Diversity & Inclusion

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.