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

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ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
* * * * $ 10,000.00 Seller's credit * * * * Welcome to 1050 Herman Ave, a beautifully fully remodeled home in the heart of Orlando’s desirable 32803 area! This charming home has been completely refreshed with modern finishes, creating a stylish, bright, and move-in-ready space. NEW Roof, NEW Windows, NEW A/C. Step inside to an inviting, open, and airy atmosphere with beautifully updated living areas and a remodeled kitchen designed for both everyday living and entertaining. Thoughtful updates throughout give this home a clean, contemporary feel while maintaining its original charm and character. Outside, enjoy a spacious yard with plenty of possibilities for entertaining, relax

$459,900

2 beds2 baths1,288 sq ft

1050 Herman Ave, Orlando, FL 32803

Spacious yard • Remodeled kitchen • 6,758 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Hot Oakland opportunity. Motivated seller, bring all offers. This two-bed, one-bath on a no HOA lot puts you minutes to John’s Lake boat access and the West Orange Trail, plus a short hop to downtown Winter Garden dining and shops. Fix and flip, hold as a rental, or tear down and build new. The upside is real and the seller is ready. Quiet small-town setting with outdoor perks and growth around you. Don’t wait. Opportunities at this price and location move fast.

$199,000

2 beds1 bath722 sq ft

320 W Sadler Ave, Oakland, FL 34760

West orange trail • No hoa lot • Outdoor perks

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
LIGHT HANDY-MAN SPECIAL LOCATED IN THE PINE HILLS AREA. FRONT PROPERTY IS A 3 BEDROOM/1 BATHROOM WITH 1,152SQFT. BACK HOUSE IS A 1 BEDROOM/1 BATHROOM WITH 600SQFT. BOTH UNITS WERE RENOVATED IN 2019/2020. CALL WITH ANY QUESTIONS!!!

$245,000

4 beds2 baths1,632 sq ft

4727 Abaca St, Orlando, FL 32808

9,621 sq ft lot • Garage • Built 1957

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
This historic 2-Bedroom 1-Bathroom Bungalow is located in one of Downtown Orlando’s most desirable neighborhoods. The 1925 Bungalow comes with a rare asset. It has a detached 1970 1-Bedroom 1-Bathroom guesthouse offering exceptional flexibility for additional rental income, hosting guests, or multigenerational living. These opportunities do not come on the market often so snap this one up! The detached Cottage is features a separate OUC electrical meter, separate internet and qualifies for the City's long term and/or short term rental. Improvements to the property include new roofs on both structures (2023) and the Bungalow has been repiped water service line to the City meter (2025)

$550,000

3 beds2 baths1,484 sq ft

1407 E Ridgewood St, Orlando, FL 32803

Detached adu • Detached cottage • New roofs

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Enjoy convenient, low maintenance living in this spacious 1 bedroom, 1 bath poolside condo, centrally located walking distance of Downtown Orlando. This refresh first floor unit features an updated kitchen with new appliances, cabinets and countertops along with plenty of storage throughout. The bathroom has a relaxing whirlpool tub. Step outside and enjoy easy access to the community pool and clubhouse, complete with convenient laundry facilities. Take a stroll through the well-maintained grounds or unwind on the recently renovated dock while enjoying peaceful views of the lake. Convenient location, updated features and resort-style surroundings make this condo a wonderful place to call ho

$157,500

1 bed1 bath644 sq ft

320 Lakeview St #108, Orlando, FL 32804

Whirlpool tub • Updated kitchen • $553 HOA

Property at 4201 Monarch Dr, Orlando, FL 32812, 3 beds, 1 bath

$275,000

3 beds1 bath888 sq ft

4201 Monarch Dr, Orlando, FL 32812

Property at 212 W 1st Ave, Windermere, FL 34786, 4 beds, 2 baths

$1,498,000

4 beds2 baths2,627 sq ft

212 W 1st Ave, Windermere, FL 34786

Property at 4321 Lake Lawne Ave, Orlando, FL 32808, 2 beds, 1 bath

$195,000

2 beds1 bath914 sq ft

4321 Lake Lawne Ave, Orlando, FL 32808

Property at 2418 E Jersey Ave, Orlando, FL 32806, 2 beds, 2 baths

$369,900

2 beds2 baths1,750 sq ft

2418 E Jersey Ave, Orlando, FL 32806

Property at 6809 Willoughby Ln, Belle Isle, FL 32812, 3 beds, 2 baths

$650,000

3 beds2 baths1,675 sq ft

6809 Willoughby Ln, Belle Isle, FL 32812

Property at 1008 Berwyn Rd, Orlando, FL 32806, 3 beds, 2 baths

$489,900

3 beds2 baths1,446 sq ft

1008 Berwyn Rd, Orlando, FL 32806

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

$324,000

4 beds2 baths1,114 sq ft

7008 Tripoli Way, Orlando, FL 32822

Property at 3107 Lake Margaret Dr, Orlando, FL 32806, 3 beds, 2 baths

$549,000

3 beds2 baths1,905 sq ft

3107 Lake Margaret Dr, Orlando, FL 32806

Property at 4821 Shoshone St, Orlando, FL 32819, 3 beds, 2 baths

$292,500

3 beds2 baths1,130 sq ft

4821 Shoshone St, Orlando, FL 32819

Property at 3637 N Orange Blossom Trl, Orlando, FL 32804, 4 beds, 4 baths

$700,000

4 beds4 baths2,496 sq ft

3637 N Orange Blossom Trl, Orlando, FL 32804

Property at 208 3rd St, Winter Garden, FL 34787, 8 beds, 3 baths

$435,000

8 beds3 baths1,750 sq ft

208 3rd St, Winter Garden, FL 34787

Property at 1220 Howell Branch Rd, Winter Park, FL 32789, 3 beds, 2 baths

$999,500

3 beds2 baths1,487 sq ft

1220 Howell Branch Rd, Winter Park, FL 32789

Property at 1905 Arlington St, Orlando, FL 32805, 3 beds, 2 baths

$350,000

3 beds2 baths1,778 sq ft

1905 Arlington St, Orlando, FL 32805

Property at 3126 S Osceola Ave, Orlando, FL 32806, 3 beds, 2.5 baths

$545,000

3 beds2.5 baths2,739 sq ft

3126 S Osceola Ave, Orlando, FL 32806

Property at 1911 W Amelia St, Orlando, FL 32805, 3 beds, 2 baths

$415,000

3 beds2 baths2,037 sq ft

1911 W Amelia St, Orlando, FL 32805

Property at 3318 Debbie Dr, Orlando, FL 32806, 3 beds, 2 baths

$428,000

3 beds2 baths1,318 sq ft

3318 Debbie Dr, Orlando, FL 32806

Property at 368 N Boyd St, Winter Garden, FL 34787, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,331 sq ft

368 N Boyd St, Winter Garden, FL 34787

Property at 2506 Delaney Ave, Orlando, FL 32806, 4 beds, 2.5 baths

$489,000

4 beds2.5 baths1,933 sq ft

2506 Delaney Ave, Orlando, FL 32806

Property at 540 N Pennsylvania Ave, Winter Park, FL 32789, 4 beds, 2 baths

$3,950,000

4 beds2 baths1,652 sq ft

540 N Pennsylvania Ave, Winter Park, FL 32789

Property at 3271 Robinson St, Zellwood, FL 32798, 3 beds, 2 baths

$340,000

3 beds2 baths1,469 sq ft

3271 Robinson St, Zellwood, FL 32798

Property at 2511 Kilgore St, Orlando, FL 32803, 3 beds, 1 bath

$385,000

3 beds1 bath1,147 sq ft

2511 Kilgore St, Orlando, FL 32803

Property at 918 S Goldwyn Ave, Orlando, FL 32805, 2 beds, 1 bath

$190,000

2 beds1 bath888 sq ft

918 S Goldwyn Ave, Orlando, FL 32805

Property at 1955 Eland Ave, Winter Park, FL 32789, 3 beds, 2 baths

$410,000

3 beds2 baths1,494 sq ft

1955 Eland Ave, Winter Park, FL 32789

Property at 1427 Bryn Mawr St, Orlando, FL 32804, 3 beds, 2 baths

$495,000

3 beds2 baths1,617 sq ft

1427 Bryn Mawr St, Orlando, FL 32804

Property at 3126 Kelvington Dr, Orlando, FL 32810, 3 beds, 2 baths

$249,990

3 beds2 baths1,074 sq ft

3126 Kelvington Dr, Orlando, FL 32810

Property at 3625 Cochran St, Apopka, FL 32703, 4 beds, 2 baths

$289,900

4 beds2 baths1,368 sq ft

3625 Cochran St, Apopka, FL 32703

Property at 2434 Trace Ave, Belle Isle, FL 32809, 3 beds, 2 baths

$460,000

3 beds2 baths1,551 sq ft

2434 Trace Ave, Belle Isle, FL 32809

Property at 2410 Lando Ln, Orlando, FL 32806, 4 beds, 2 baths

$449,000

4 beds2 baths1,635 sq ft

2410 Lando Ln, Orlando, FL 32806

Property at 1600 Roosevelt Ave, Orlando, FL 32804, 3 beds, 1 bath

$299,000

3 beds1 bath1,364 sq ft

1600 Roosevelt Ave, Orlando, FL 32804

Property at 425 S Observatory Dr, Orlando, FL 32835, 3 beds, 2 baths

$299,900

3 beds2 baths1,300 sq ft

425 S Observatory Dr, Orlando, FL 32835

Property at 6601 Harvey St, Orlando, FL 32809, 4 beds, 2 baths

$375,000

4 beds2 baths1,322 sq ft

6601 Harvey St, Orlando, FL 32809

Property at 1502 Montcalm St, Orlando, FL 32806, 3 beds, 2 baths

$430,000

3 beds2 baths1,383 sq ft

1502 Montcalm St, Orlando, FL 32806

Property at 250 W 7th St, Apopka, FL 32703, 2 beds, 1 bath

$195,500

2 beds1 bath972 sq ft

250 W 7th St, Apopka, FL 32703

Property at 317 W King St, Orlando, FL 32804, 3 beds, 2 baths

$619,000

3 beds2 baths1,722 sq ft

317 W King St, Orlando, FL 32804

Property at 509 Hillside Ave, Orlando, FL 32803, 4 beds, 2 baths

$529,000

4 beds2 baths1,492 sq ft

509 Hillside Ave, Orlando, FL 32803

Property at 901 Baltimore Dr, Orlando, FL 32810, 3 beds, 3 baths

$390,000

3 beds3 baths1,484 sq ft

901 Baltimore Dr, Orlando, FL 32810

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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 Fri Oct 09 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 590 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 79 days and receive 1 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 1283 homes have been sold in Orange County. In addition to houses in Orange County, there were also 1905 condos, 1021 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.

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