Vintage homes for sale & real estate in Kentucky, KY

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ABOUT THIS HOME
Vintage Home for sale in Kentucky, KY:
Located in the heart of Louisville's highly desirable Highlands neighborhood, this exceptional four-plex is a rare opportunity on one of the city's most iconic streets within one of its strongest rental markets. This stately three-story brick property features four spacious units ranging from one to three bedrooms, each offering unique character with features such as sunrooms, butler's pantries, and mudrooms. Additional amenities include a full basement with laundry, a large fenced backyard, and three rear garages. The sellers recently inherited the property and have limited historical knowledge beyond its long-standing history as a stable, income-producing rental with very low vacancy. Rec

$695,000

8 beds5 baths5,200 sq ft

2114 Bonnycastle Ave, Louisville, KY 40205

Full basement • Three rear garages • Four-plex

Homepage Realty

ABOUT THIS HOME
Vintage Home for sale in Kentucky, KY:
This remodeled 4-bedroom, 2.5-bathroom home perfectly blends modern sophistication with serene country living. The heart of the home features a sleek, updated kitchen fully equipped with stainless steel appliances, ideal for both daily meals and weekend entertaining. Whether you're enjoying the quiet views from your expansive yard or relaxing in the stylishly refreshed interior, this property offers the space and quality you’ve been searching for. Don't miss this rare opportunity to own a move-in-ready gem in a tranquil Allen County setting!

$321,000

4 beds2.5 baths2,012 sq ft

48 Pope Trammel Rd, Scottsville, KY 42164

Move-in-ready • Expansive yard • Updated kitchen

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Kentucky, KY:
Step into a piece of Mason County history. Built in 1900, this 3 bed, 2 bath two-story farmhouse has known only four owners in its lifetime - and it's ready for its fifth. Sitting on 1.45 acres, the layout is as thoughtful as the setting: the front porch faces due east for morning sunrises, while the back patio faces due west for evening sunsets. Inside, the rooms are generously sized and a flexible first-floor room offers an easy path to a 4th bedroom. The metal roof means low long-term maintenance, and recent updates include new windows, a new front door, new concrete sidewalks, and a new front porch floor. The primary shower has also been updated and the main stairwell and foyer with its

$379,000

3 beds2 baths2,272 sq ft

132 W Maple Leaf Rd, Maysville, KY 41056

Metal roof • Front porch • New front door

ABOUT THIS HOME
Vintage Home for sale in Kentucky, KY:
This brick home is conveniently located just minutes from all the shopping and resturants the city of Harlan has to offer! Inside you will find spacious rooms, beautiful hardwood floors, good storage space and a wood burning fire place for those chilly nights just to name a few features this home has to offer! Come see it in person, you just may not want to leave!!

$115,900

3 beds1 bath1,221 sq ft

116 Wolf Hollow Rd, Baxter, KY 40806

Brick home • Good storage space • Hardwood floors

ABOUT THIS HOME
Vintage Home for sale in Kentucky, KY:
Instant cash flow and a stress-free addition to any portfolio. This updated 2 bed, 1 bath home comes with a year lease already in place, delivering immediate income from day one. Well-maintained and tenant occupied, it's a dependable, turnkey investment with minimal oversight required. Opportunities like this—clean, cash producing, and ready to go—don't come around often.

$54,900

2 beds1 bath950 sq ft

2108 Wilson Ave, Louisville, KY 40210

4,200 sq ft lot • Built 1900 • Listed 187 days

Real Estate Go To

Property at 115 Grandview Dr, Cynthiana, KY 41031, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths3,446 sq ft

115 Grandview Dr, Cynthiana, KY 41031

Property at 3003 Dixie Hwy, Shively, KY 40216, 6 beds, 1.5 baths

$309,000

6 beds1.5 baths2,448 sq ft

3003 Dixie Hwy, Shively, KY 40216

J. Michael Jones & Associates

Property at 1311 E 13th St, Bowling Green, KY 42101, 4 beds, 2 baths

$179,900

4 beds2 baths1,316 sq ft

1311 E 13th St, Bowling Green, KY 42101

Property at 2891 State Route 469, Keaton, KY 41226, 4 beds, 2 baths

$325,000

4 beds2 baths1,972 sq ft

2891 State Route 469, Keaton, KY 41226

Property at 851 Ivy Ave, Frankfort, KY 40601, 4 beds, 2.5 baths

$369,000

4 beds2.5 baths1,760 sq ft

851 Ivy Ave, Frankfort, KY 40601

Property at 821 Runnels Br, Littcarr, KY 41834, 3 beds, 1 bath

$54,999

3 beds1 bath1,020 sq ft

821 Runnels Br, Littcarr, KY 41834

Property at 717 Cleveland Ave, Glasgow, KY 42141, 4 beds, 2.5 baths

$199,000

4 beds2.5 baths2,341 sq ft

717 Cleveland Ave, Glasgow, KY 42141

Property at 106 Crestwood Ave, Louisville, KY 40206, 4 beds, 4 baths

$510,000

4 beds4 baths2,584 sq ft

106 Crestwood Ave, Louisville, KY 40206

Sun Residential

Property at 218 & 220 S Clay St, Louisville, KY 40202

$2,100,000

Studio— baths5,948 sq ft

218 & 220 S Clay St, Louisville, KY 40202

Lenihan Sotheby's Int'l Realty

Property at 1382 Ouerbacker Ct, Louisville, KY 40208

$469,000

Studio— baths3,320 sq ft

1382 Ouerbacker Ct, Louisville, KY 40208

Colliers

Property at 218 Mammoth Cave St, Cave City, KY 42127, 3 beds, 2 baths

$315,000

3 beds2 baths3,226 sq ft

218 Mammoth Cave St, Cave City, KY 42127

Property at 1814 Standard Ave, Louisville, KY 40210, 4 beds, 1 bath

$135,000

4 beds1 bath1,120 sq ft

1814 Standard Ave, Louisville, KY 40210

Lifestyl Louisville

Property at 1922 Rowan St, Louisville, KY 40203, 2 beds, 1 bath

$45,000

2 beds1 bath1,027 sq ft

1922 Rowan St, Louisville, KY 40203

Semonin Realtors

Property at 707 Dornell St, Owensboro, KY 42301, 3 beds, 1 bath

$99,999

3 beds1 bath800 sq ft

707 Dornell St, Owensboro, KY 42301

Property at 2008 W Jefferson St, Louisville, KY 40203, 6 beds, 5 baths

$199,000

6 beds5 baths5,446 sq ft

2008 W Jefferson St, Louisville, KY 40203

Homepage Realty

Property at 201 York Ln, Danville, KY 40422, 4 beds, 2 baths

$399,900

4 beds2 baths1,849 sq ft

201 York Ln, Danville, KY 40422

Property at 6166 Greenwich Pike, Lexington, KY 40511, 5 beds, 2.5 baths

$5,900,000

5 beds2.5 baths2,629 sq ft

6166 Greenwich Pike, Lexington, KY 40511

Property at 311 W Madison St, Franklin, KY 42134, 2 beds, 1 bath

$189,000

2 beds1 bath1,540 sq ft

311 W Madison St, Franklin, KY 42134

Property at 333 N 29th St, Louisville, KY 40212, 8 beds, 4 baths

$145,000

8 beds4 baths2,432 sq ft

333 N 29th St, Louisville, KY 40212

Real Broker, LLC

Property at 3014 Poplar Hill Rd, Liberty, KY 42539, 4 beds, 4 baths

$294,000

4 beds4 baths2,578 sq ft

3014 Poplar Hill Rd, Liberty, KY 42539

Property at 1926 Wrocklage Ave, Louisville, KY 40205, 3 beds, 1 bath

$315,000

3 beds1 bath1,294 sq ft

1926 Wrocklage Ave, Louisville, KY 40205

Kentucky Select Properties

Property at 1034 Patterson St, Newport, KY 41071, 4 beds, 1 bath

$214,500

4 beds1 bath1,326 sq ft

1034 Patterson St, Newport, KY 41071

Property at 701 Ervin Ter, Dayton, KY 41074, 4 beds, 2 baths

$384,900

4 beds2 baths2,034 sq ft

701 Ervin Ter, Dayton, KY 41074

Property at 1716 Gallagher St, Louisville, KY 40210, 3 beds, 1 bath

$89,999

3 beds1 bath1,113 sq ft

1716 Gallagher St, Louisville, KY 40210

The Collective Realty Co.

Property at 1140 S 3rd St, Louisville, KY 40203

$350,000

Studio— baths3,000 sq ft

1140 S 3rd St, Louisville, KY 40203

United Real Estate Louisville

Property at 615 S 44th St, Louisville, KY 40211

$2,695,000

Studio— baths42,686 sq ft

615 S 44th St, Louisville, KY 40211

Colliers

Property at 405 Lawrence St, Brandenburg, KY 40108, 5 beds, 2 baths

$329,900

5 beds2 baths2,259 sq ft

405 Lawrence St, Brandenburg, KY 40108

NextHome Chism Realty

Property at 678 Princeton Rd, Madisonville, KY 42431, 3 beds, 1 bath

$135,000

3 beds1 bath1,592 sq ft

678 Princeton Rd, Madisonville, KY 42431

Property at 260 Reed Ave, Madisonville, KY 42431, 3 beds, 2 baths

$199,900

3 beds2 baths2,400 sq ft

260 Reed Ave, Madisonville, KY 42431

Property at 415 Chestnut St, Lexington, KY 40508, 2 beds, 1 bath

$114,900

2 beds1 bath3,780 sq ft

415 Chestnut St, Lexington, KY 40508

Property at 609 Crestview Ln, Morehead, KY 40351, 4 beds, 3 baths

$390,000

4 beds3 baths2,824 sq ft

609 Crestview Ln, Morehead, KY 40351

Property at 207 York St, Lexington, KY 40508, 1 bed, 1 bath

$160,000

1 bed1 bath618 sq ft

207 York St, Lexington, KY 40508

Property at 3229 Garland Ave, Louisville, KY 40211, 3 beds, 1 bath

$73,000

3 beds1 bath1,080 sq ft

3229 Garland Ave, Louisville, KY 40211

Right Choice Realty Inc.

Property at 110 Pearl Street St, Fulton, KY 42041, 5 beds, 1.5 baths

$155,000

5 beds1.5 baths2,518 sq ft

110 Pearl Street St, Fulton, KY 42041

Property at 87 Winns 2nd St, Pikeville, KY 41501, 3 beds, 2 baths

$109,000

3 beds2 baths1,150 sq ft

87 Winns 2nd St, Pikeville, KY 41501

Property at 42 Mockingbird Valley Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$445,500

3 beds2.5 baths2,961 sq ft

42 Mockingbird Valley Rd, Winchester, KY 40391

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Vintage Homes for Sale in Kentucky

There are currently 3108 vintage homes for sale in Kentucky. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. This map is refreshed with the newest listings in Kentucky every 15 minutes.

Find your dream vintage homes in Kentucky 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 Kentucky are local experts and are ready to answer your questions about properties , neighborhoods, schools, and the newest listings for sale in Kentucky. If you're looking to sell your home in the Kentucky area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Kentucky with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

Popular Cities in Kentucky

Popular Searches in Kentucky, KY

Based on information submitted to the MLS GRID as of Mon Sep 21 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.

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