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:
Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private . 21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating invi

$850,000

3 beds3 baths2,488 sq ft

2345 Brookshire Ave, Winter Park, FL 32792

Private lot • New landscaping • Flagstone entry

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Welcome to this delightful 3-bedroom, 1-bathroom home located in the heart of East Orlando! This property is perfect for first-time homebuyers or investors seeking a great opportunity. Modern Upgrades: Enjoy a newer roof, a 5-year-old AC unit, and a newer water heater, ensuring peace of mind and energy efficiency. Bright & Airy: The home boasts newer windows that allow for plenty of natural light, creating a warm and inviting atmosphere. Stylish Kitchen & Bathroom: Both the kitchen and bathroom have been tastefully upgraded, featuring modern fixtures and finishes. No HOA: Enjoy the freedom of homeownership without the restrictions of an HOA. Solar Panels: The property is equippe

$280,000

3 beds1 bath825 sq ft

2331 Nansen Ave, Orlando, FL 32817

Upgraded bathroom • 5 year old ac unit • Newer roof

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
HONEY, STOP THE CAR! This is not your typical Orlando property! Featuring multiple living spaces, incredible flexibility, and your very own private outdoor retreat, this is one you’ll want to see in person. The main residence features 2 bedrooms with comfortable living areas and plenty of opportunity to make the space your own. What really sets this property apart is the additional in-law suite, creating extra space that could be ideal for extended family, guests, a private home office, or additional accommodations. The property also includes an RV with even more additional living space, making this a setup that is hard to find at this price point. Step outside and discover an outdoor

$219,000

1 bed1 bath472 sq ft

2301 Drake Dr, Orlando, FL 32810

In-law suite • Outdoor oasis • Rv living space

COMING SOONFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Does LOCATION matter to you? Then come on out to this beautiful Eastbrook Winter Park home on a large corner lot. Fenced Yard with a large screened back porch!! This house is centrally located to the Orlando Airport, downtown Orlando area, Park Avenue and University of Central Florida close to stores, restaurants and gyms. It has been very well maintained. Spacious and move in ready . Plumbing, electrical and water heater were all updated in 2019. Property features a spacious laundry room with plenty of space for storage. Bathrooms have been remodeled. Backyard is completely fenced and large enough to keep an RV, trailer and more. House has been remodeled to either occupy the whole house or

$395,000

4 beds3 baths1,421 sq ft

3416 Arbutus Ln, Winter Park, FL 32792

Large corner lot • Fenced yard • Centrally located

SHORT SALE

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Short Sale. * * Short sale, third party approval required * * Welcome home to 4324 Aetna Dr, a fully remodeled 2 bed, 1 bath home in Orlando. The layout gives you more room than you'd expect. A huge bonus room can be an oversized primary suite, a cozy den, or a quiet home office. The whole home was remodeled in late 2024. Luxury vinyl plank flooring runs throughout, and the kitchen has shaker cabinets and quartz countertops. The bathroom was fully redone, and impact windows add comfort and peace of mind. The roof and water heater were also replaced in 2024, so the big things are already taken care of. The home is minutes from W Colonial Dr, SR-408, I-4, and downtown Orlando, with shop

$224,999

3 beds1 bath884 sq ft

4324 Aetna, Orlando, FL 32808

Huge bonus room • Quartz countertops • Fully remodeled

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

$311,000

3 beds2 baths1,100 sq ft

701 23rd St, Orlando, FL 32805

Property at 642 20th St, Orlando, FL 32805, 2 beds, 1 bath

$219,900

2 beds1 bath908 sq ft

642 20th St, Orlando, FL 32805

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

$664,000

3 beds3 baths1,794 sq ft

900 Carver St, Winter Park, FL 32789

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

$400,000

2 beds2 baths1,215 sq ft

1601 Bryn Mawr St, Orlando, FL 32804

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

$575,000

5 beds3 baths2,771 sq ft

4511 Longworth Dr, Orlando, FL 32812

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 1819 Lake Sue Dr, Orlando, FL 32803, 3 beds, 2 baths

$699,000

3 beds2 baths1,620 sq ft

1819 Lake Sue Dr, Orlando, FL 32803

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

$400,000

3 beds2 baths1,247 sq ft

2829 Lake Margaret Dr, 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 3000 Rogan Rd, Orlando, FL 32812, 3 beds, 1.5 baths

$395,000

3 beds1.5 baths1,323 sq ft

3000 Rogan Rd, Orlando, FL 32812

Property at 323 E Amelia St, Orlando, FL 32801, 4 beds, 3.5 baths

$1,175,000

4 beds3.5 baths2,080 sq ft

323 E Amelia St, Orlando, FL 32801

Property at 3811 Wilts St, Orlando, FL 32805, 2 beds, 1 bath

$249,900

2 beds1 bath720 sq ft

3811 Wilts St, Orlando, FL 32805

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 772 Willie Mays Pkwy, Orlando, FL 32811, 2 beds, 1 bath

$199,990

2 beds1 bath682 sq ft

772 Willie Mays Pkwy, Orlando, FL 32811

Property at 325 W Newell St, Winter Garden, FL 34787, 2 beds, 2 baths

$585,000

2 beds2 baths1,051 sq ft

325 W Newell St, Winter Garden, FL 34787

Property at 4324 Elderberry Dr, Orlando, FL 32809, 4 beds, 2 baths

$345,000

4 beds2 baths1,044 sq ft

4324 Elderberry Dr, Orlando, FL 32809

Property at 5917 Wolf Rd, Orlando, FL 32808, 3 beds, 2 baths

$275,000

3 beds2 baths1,114 sq ft

5917 Wolf Rd, Orlando, FL 32808

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 1200 Austin Rd, Orlando, FL 32806, 3 beds, 2 baths

$699,000

3 beds2 baths2,154 sq ft

1200 Austin Rd, Orlando, FL 32806

Property at 5240 Alleman Dr, Orlando, FL 32809, 5 beds, 4.5 baths

$999,000

5 beds4.5 baths4,482 sq ft

5240 Alleman Dr, Orlando, FL 32809

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

$500,000

3 beds2 baths1,772 sq ft

5701 Padgett Cir, Orlando, FL 32839

Property at 3627 Arch St, Orlando, FL 32808, 3 beds, 2 baths

$330,000

3 beds2 baths1,353 sq ft

3627 Arch St, Orlando, FL 32808

Property at 913 Moss Ln, Winter Park, FL 32789, 3 beds, 2 baths

$950,000

3 beds2 baths1,887 sq ft

913 Moss Ln, Winter Park, FL 32789

Property at 1008 Keats Ave, Orlando, FL 32809, 3 beds, 2 baths

$350,000

3 beds2 baths1,698 sq ft

1008 Keats Ave, Orlando, FL 32809

Property at 236 Emory Pl, Orlando, FL 32804, 4 beds, 2 baths

$849,900

4 beds2 baths1,830 sq ft

236 Emory Pl, Orlando, FL 32804

Property at 10810 Genevieve St, Orlando, FL 32825, 3 beds, 2 baths

$389,998

3 beds2 baths1,476 sq ft

10810 Genevieve St, Orlando, FL 32825

Property at 804 W Concord St, Orlando, FL 32805, 6 beds, 6 baths

$1,049,000

6 beds6 baths3,686 sq ft

804 W Concord St, Orlando, FL 32805

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

$330,000

3 beds2 baths1,497 sq ft

6401 Ramir Rd, Orlando, FL 32810

Property at 2512 Healy Dr, Orlando, FL 32818, 3 beds, 2 baths

$339,999

3 beds2 baths1,825 sq ft

2512 Healy Dr, Orlando, FL 32818

Property at 311 E Morse Blvd Unit 1-5, Winter Park, FL 32789, 3 beds, 3 baths

$2,475,000

3 beds3 baths2,316 sq ft

311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

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 4107 Dublin St, Orlando, FL 32812, 3 beds, 2 baths

$349,000

3 beds2 baths1,190 sq ft

4107 Dublin St, Orlando, FL 32812

Property at 2917 Pickfair St, Orlando, FL 32803, 2 beds, 1 bath

$445,000

2 beds1 bath1,111 sq ft

2917 Pickfair St, Orlando, FL 32803

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 2918 Carl Ter, Orlando, FL 32804, 3 beds, 2 baths

$585,000

3 beds2 baths2,013 sq ft

2918 Carl Ter, Orlando, FL 32804

Property at 401 E Jersey St, Orlando, FL 32806, 3 beds, 2 baths

$435,000

3 beds2 baths1,344 sq ft

401 E Jersey St, Orlando, FL 32806

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Based on information submitted to the MLS GRID as of Tue Oct 06 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 591 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, 1248 homes have been sold in Orange County. In addition to houses in Orange County, there were also 1903 condos, 1018 townhouses, and 62 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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