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

466 homes

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NEW 32 MINS AGO

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Welcome to 5355 E Kaley Street, a 3-bedroom, 2-bath classic ranch-style home located in the desirable Conway community of Orlando. This solid 1956-built home offers 1,234 square feet of living space on a very large 10,497 square foot lot, combining classic elements and well designed updates. This cozy home features an updated kitchen, remodeled bathrooms, gorgeous original wood floors, a practical and efficient floor plan, and comfortable living areas ideal for everyday comforts. Step outside to a beautiful oasis including a screened pool and spacious backyard—perfect for Florida living, entertaining, or quiet evenings at home. Other recent improvements include roof replacement in 201

$365,000

3 beds2 baths1,234 sq ft

5355 E Kaley St, Orlando, FL 32812

Screened pool • Spacious backyard • Original wood floors

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Investor Special in Prime Orlando Location — Sold As-Is! Opportunity knocks in the heart of Orlando. This fixer-upper is ideal for investors, flippers, or buyers looking to create a solid rental property in a high-demand area. With the right vision and updates, this property offers strong upside and value-add potential. Sold AS-IS, this home is ready for renovation and priced accordingly—bring your contractor and your imagination. Whether you’re planning a fix-and-flip or a long-term rental, the bones and location make this a smart investment play. Situated just minutes from Downtown Orlando with quick access to SR-50, 408, and I-4, commuting and tenant appeal are major wi

$99,000

3 beds1 bath1,008 sq ft

2848 W Harwood St, Orlando, FL 32805

Strong upside • Value-add potential • Ready for renovation

NEW 31 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Tucked away on a quiet, dead-end street in the heart of * * College Park * * , this fully renovated * * 3 bedroom, 2 bathroom * * home is truly turnkey. Situated on a . 18-acre lot beneath a beautiful canopy of mature oak trees, the property features a * * heated saltwater pool and spa * * , expansive paver patio, screened covered porch, and a fully fenced backyard designed for everyday living and entertaining. Inside, the open layout is filled with natural light and showcases a custom kitchen with a large island, soft-close cabinetry, granite countertops, and stainless steel appliances, all flowing into the living and dining spaces. The primary suite offers a private bath, while

$525,000

3 beds2 baths1,080 sq ft

3518 Fairway Ln, Orlando, FL 32804

Custom kitchen • Large island • 7,706 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Spacious block home in the established Rio Grande Terrace neighborhood with no HOA. The main residence offers three bedrooms and two bathrooms, plus an attached fourth bedroom with a private exterior entrance and no interior access to the main living area, providing flexible space ideal for extended family, long-term guests, or a private office. Generous laundry room, ample storage, and a large backyard perfect for gatherings or future personalization. Conveniently located near Downtown Orlando with easy access to I-4, SR-408, shopping, dining, and local amenities.

$315,000

4 beds3 baths1,728 sq ft

1713 27th St, Orlando, FL 32805

Flexible space • Large backyard • 7,667 sq ft lot

NEW 30 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Orange County, FL:
Come Checkout, this fully Remodeled home. 3 Bedroom, 2 Bath. This Home has been Rewired (2022), New roof (2022), Water Proof Laminate Floor Throughout, Fully renovated Kitchen with Granite Counter Tops, white shaker Cabinets and Stainless Steel Bosh Appliances. Both Baths have been remodeled. Enjoy Outdoor Living with Fully Fenced Backyard and Resurfaced Sparkling Pool with a New Pump filter System, Timer and Light (2022). No HOA. Moving In Ready Come to See it!

$365,000

3 beds2 baths1,573 sq ft

1412 Lakecrest Dr, Apopka, FL 32703

Rewired • Granite counter tops • New roof

Property at 1308 W Princeton St, Orlando, FL 32804, 3 beds, 2 baths

$539,900

3 beds2 baths1,427 sq ft

1308 W Princeton St, Orlando, FL 32804

Property at 1214 Elinore Dr, Orlando, FL 32808, 4 beds, 2 baths

$344,900

4 beds2 baths1,838 sq ft

1214 Elinore Dr, Orlando, FL 32808

Property at 1214 Maverick Dr, Apopka, FL 32703, 4 beds, 2 baths

$315,000

4 beds2 baths1,504 sq ft

1214 Maverick Dr, Apopka, FL 32703

Property at 1746 Dormont Ln, Orlando, FL 32804, 2 beds, 2 baths

$540,000

2 beds2 baths1,537 sq ft

1746 Dormont Ln, Orlando, FL 32804

Property at 1518 Pinewood Dr, Winter Park, FL 32789, 3 beds, 2 baths

$499,900

3 beds2 baths1,197 sq ft

1518 Pinewood Dr, Winter Park, FL 32789

Property at 8120 Gondola Dr, Orlando, FL 32809, 4 beds, 3 baths

$550,000

4 beds3 baths1,405 sq ft

8120 Gondola Dr, Orlando, FL 32809

Property at 632 Cardinal St, Ocoee, FL 34761, 3 beds, 1.5 baths

$305,000

3 beds1.5 baths1,202 sq ft

632 Cardinal St, Ocoee, FL 34761

Property at 1402 S Lee Ave, Orlando, FL 32805, 3 beds, 1 bath

$260,000

3 beds1 bath1,108 sq ft

1402 S Lee Ave, Orlando, FL 32805

Property at 2707 Sea Breeze Ct, Orlando, FL 32805, 4 beds, 2 baths

$5,000

4 beds2 baths1,728 sq ft

2707 Sea Breeze Ct, Orlando, FL 32805

Property at 3707 Westwood Rd, Orlando, FL 32808, 3 beds, 1.5 baths

$180,000

3 beds1.5 baths1,139 sq ft

3707 Westwood Rd, Orlando, FL 32808

Property at 113 S Glenwood Ave, Orlando, FL 32803, 2 beds, 1 bath

$310,000

2 beds1 bath852 sq ft

113 S Glenwood Ave, Orlando, FL 32803

Property at 4601 Robbins Ave, Orlando, FL 32808, 3 beds, 2 baths

$315,000

3 beds2 baths1,444 sq ft

4601 Robbins Ave, Orlando, FL 32808

Property at 2800 Hargill Dr, Orlando, FL 32806, 4 beds, 3 baths

$554,000

4 beds3 baths1,929 sq ft

2800 Hargill Dr, Orlando, FL 32806

Property at 1800 Palm Ln, Orlando, FL 32803, 3 beds, 1 bath

$389,000

3 beds1 bath1,153 sq ft

1800 Palm Ln, Orlando, FL 32803

Property at 621 Westdale Ave, Orlando, FL 32805, 2 beds, 1 bath

$160,000

2 beds1 bath929 sq ft

621 Westdale Ave, Orlando, FL 32805

Property at 96 & 98 W Esther St, Orlando, FL 32806, 5 beds, 2 baths

$485,000

5 beds2 baths1,501 sq ft

96 & 98 W Esther St, Orlando, FL 32806

Property at 4615 S Fern Creek Ave, Orlando, FL 32806, 4 beds, 3 baths

$490,000

4 beds3 baths2,109 sq ft

4615 S Fern Creek Ave, Orlando, FL 32806

Property at 1336 College Pt, Winter Park, FL 32789, 4 beds, 4 baths

$4,595,000

4 beds4 baths3,181 sq ft

1336 College Pt, Winter Park, FL 32789

Property at 5770 Chipola Cir, Orlando, FL 32839, 4 beds, 3 baths

$349,900

4 beds3 baths2,657 sq ft

5770 Chipola Cir, Orlando, FL 32839

Property at 913 Emeralda Rd, Orlando, FL 32808, 4 beds, 1 bath

$179,900

4 beds1 bath1,287 sq ft

913 Emeralda Rd, Orlando, FL 32808

Property at 5605 Lejeune Dr, Orlando, FL 32808, 3 beds, 2 baths

$245,000

3 beds2 baths1,040 sq ft

5605 Lejeune Dr, Orlando, FL 32808

Property at 618 Piedmont St, Orlando, FL 32805, 2 beds, 1 bath

$219,000

2 beds1 bath989 sq ft

618 Piedmont St, Orlando, FL 32805

Property at 29 N Brown Ave, Orlando, FL 32801, 4 beds, 3.5 baths

$1,050,000

4 beds3.5 baths3,032 sq ft

29 N Brown Ave, Orlando, FL 32801

Property at 1213 Lindenwood Ln, Winter Park, FL 32792, 4 beds, 2 baths

$750,000

4 beds2 baths2,505 sq ft

1213 Lindenwood Ln, Winter Park, FL 32792

Property at 1724 Riley Ave, Orlando, FL 32805, 3 beds, 1 bath

$199,000

3 beds1 bath1,128 sq ft

1724 Riley Ave, Orlando, FL 32805

Property at 7413 Matchett Rd, Belle Isle, FL 32809, 3 beds, 3 baths

$385,000

3 beds3 baths1,616 sq ft

7413 Matchett Rd, Belle Isle, FL 32809

Property at 18 W Vining St, Winter Garden, FL 34787, 2 beds, 1 bath

$445,000

2 beds1 bath948 sq ft

18 W Vining St, Winter Garden, FL 34787

Property at 917 Romano Ave, Orlando, FL 32807, 3 beds, 2 baths

$319,900

3 beds2 baths1,074 sq ft

917 Romano Ave, Orlando, FL 32807

Property at 1602 Bren Lee Ct, Orlando, FL 32805, 3 beds, 2 baths

$225,900

3 beds2 baths1,190 sq ft

1602 Bren Lee Ct, Orlando, FL 32805

Property at 4410 Brandeis Ave, Orlando, FL 32839, 3 beds, 1.5 baths

$444,000

3 beds1.5 baths1,359 sq ft

4410 Brandeis Ave, Orlando, FL 32839

Property at 2811 Eastern Pkwy, Winter Park, FL 32789, 3 beds, 2 baths

$665,000

3 beds2 baths1,433 sq ft

2811 Eastern Pkwy, Winter Park, FL 32789

Property at 5910 Indian Hill Rd, Orlando, FL 32808, 3 beds, 2 baths

$289,990

3 beds2 baths1,606 sq ft

5910 Indian Hill Rd, Orlando, FL 32808

Property at 1614 Curry Ford Rd, Orlando, FL 32806, 3 beds, 2 baths

$489,900

3 beds2 baths1,102 sq ft

1614 Curry Ford Rd, Orlando, FL 32806

Property at 517 W Yale St, Orlando, FL 32804, 3 beds, 2 baths

$685,000

3 beds2 baths1,938 sq ft

517 W Yale St, Orlando, FL 32804

Property at 2330 Hickory Ln, Orlando, FL 32803, 3 beds, 2.5 baths

$775,000

3 beds2.5 baths2,107 sq ft

2330 Hickory Ln, Orlando, FL 32803

Property at 875 W Lyman Ave, Winter Park, FL 32789, 2 beds, 2 baths

$475,000

2 beds2 baths760 sq ft

875 W Lyman Ave, Winter Park, FL 32789

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Based on information submitted to the MLS GRID as of Wed Dec 31 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 466 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 87 days and receive 2 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 1151 homes have been sold in Orange County. In addition to houses in Orange County, there were also 1821 condos, 919 townhouses, and 42 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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