Vintage homes for sale & real estate in Shelby County, KY

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ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
A landmark Kentucky estate of extraordinary provenance, 10053 Shelbyville Road offers approximately 55 acres along one of the region's most coveted corridors near the Jefferson/Shelby County line. Built in the early 1800s, near the formation of the Commonwealth, the historic main residence is listed on the historic registry and is believed to be among the oldest homes in Kentucky, with the property recognized as one of the state's longest continuously farmed landholdings. The estate features a 5,336 sq, ft, main residence, an approximately 2,000 sq. ft. guest house, and expansive grounds suited for equestrian use, private farming, a family compound, or long-term legacy ownership. Rarely doe

$14,000,000

6 beds3 baths5,336 sq ft

10053 Shelbyville Rd, Simpsonville, KY 40067

Equestrian use • Private farming • Expansive grounds

Semonin Realtors

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Historic horse farm, located in the heart of Saddlebred country, and minutes from downtown Shelbyville features a beautifully renovated brick Federal style estate and superb equestrian horse facility. Built circa 1850, this home features modern updated amenities yet retains the charm of the age. Features include original hardwood flooring, six fireplaces, Living and Dining rooms with beautiful pocket doors, an expansive Foyer, and fabulous chandeliers in every room. The remodeled kitchen includes custom birchwood cabinetry, Dacor gas oven, warming drawer, and Butlers pantry with a wine cooler and ice maker. The second floor Primary suite features a large dressing room, remodeled bathroom wi

$2,950,000

3 beds2.5 baths5,416 sq ft

1615 Harrington Mill Rd, Shelbyville, KY 40065

Six fireplaces • Expansive foyer • Historic horse farm

simpler.realestate

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
If you are looking to step back in time or a good producing farm, just take a minute and look at this combination, hosting 184 acres , with incredible views and privacy located on Bardstown Trail. Home, build in the early 1800's, hosts approx. 4500 sq ft of living space with large rooms and tall ceilings, 2-foot-thick walls and detail woodwork not seen in today's homes. Homes could have 5 bedrooms, bath, family room, parlor and kitchen There are several fireplaces and hardwood floors everywhere. Home has updates to the heating and electricity and roof, but with your imagination bring it back to the showplace it was built to share. The property has an awesome brick machinery barn with o

$2,300,000

5 beds1 bath4,500 sq ft

1298 Bardstown, Waddy, KY 40076

Privacy • 184 acres • Incredible views

HOME LAND of Kentucky

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Some houses have a little more personality than others. 108 First Street is one of them. Start your morning on the front porch with a cup of coffee and the sounds of Simpsonville waking up around you. Church bells across the street, a short walk to the farmers market, and Simpsonville Park just down the road give this home a location that is hard to duplicate. Inside, the character continues. This well-maintained older home has the details you hope to find, including beautiful original trim, solid-core doors, and a story-and-a-half layout that gives the home plenty of personality without sacrificing function. The kitchen has been renovated, the laundry is conveniently located on the main fl

$335,000

3 beds2 baths1,788 sq ft

108 1st St, Simpsonville, KY 40067

Solid-core doors • Front porch • Renovated kitchen

Torrey Smith Realty Co., LLC

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Welcome to 689 Graefenburg Road, where a classic Cape Cod sits beside the creek on a quiet stretch of road that used to be US 60, before the highway was rebuilt and moved up the hill. The traffic went with it. What stayed behind is a peaceful country road through Graefenburg, one of Shelby County's oldest settlements, with Waddy, Shelbyville, and Frankfort all an easy drive away. This home has been owned by the same family since the 1970s, and that kind of steady care shows. The big-ticket items are already done: new roof and siding in 2012, replacement windows in 2015, a new furnace in 2020, and the air conditioner replaced in 2012. The bathroom was updated with a walk-in shower in 2023. A

$245,000

3 beds1 bath1,750 sq ft

689 Graefenburg Rd, Waddy, KY 40076

New furnace • Walk-in shower • New roof

Torrey Smith Realty Co., LLC

Property at 8576 Cropper Rd, Pleasureville, KY 40057, 3 beds, 1 bath

$169,000

3 beds1 bath1,447 sq ft

8576 Cropper Rd, Pleasureville, KY 40057

Abbot Realty & Auction

Property at 1701 Martin Nethery Rd, Waddy, KY 40076, 3 beds, 2 baths

$337,000

3 beds2 baths1,850 sq ft

1701 Martin Nethery Rd, Waddy, KY 40076

Property at 1219 Taylor Wood Rd, Simpsonville, KY 40067, 4 beds, 2 baths

$985,000

4 beds2 baths2,625 sq ft

1219 Taylor Wood Rd, Simpsonville, KY 40067

Segrest Flaherty Realtors LLC

Property at 302 Eminence Pike, Shelbyville, KY 40065, 5 beds, 3.5 baths

$899,500

5 beds3.5 baths4,266 sq ft

302 Eminence Pike, Shelbyville, KY 40065

Legacy Home REALTORS

Property at 575 Moody Pike, Shelbyville, KY 40065, 4 beds, 3.5 baths

$1,249,900

4 beds3.5 baths5,500 sq ft

575 Moody Pike, Shelbyville, KY 40065

EXP Realty LLC

Property at 4148 Bagdad Rd, Bagdad, KY 40003, 4 beds, 1.5 baths

$369,000

4 beds1.5 baths2,014 sq ft

4148 Bagdad Rd, Bagdad, KY 40003

Semonin Realtors

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ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
FIVE-PROPERTY INVESTMENT PACKAGE, SOLD TOGETHER FOR $625,000. Expand your rental portfolio with four properties in Frankfort and one in Harrodsburg, offering 11 total bedrooms and combined monthly rent of $5,750. The package includes 104 Adair Street, 615 Richardson Lane, 966 Fifth Avenue, and 524 Devils Hollow in Frankfort, plus 463 Linden Avenue in Harrodsburg. The listed address represents one property within the package, and the asking price includes all five. The rent roll is available in the listing documents, with photos of all five properties included in the photo gallery. Properties are not offered individually. With this being a package, showings will only be available for serious

$625,000

3 beds1 bath1,200 sq ft

615 Richardson Ln, Frankfort, KY 40601

0.57 acre lot • Built 1111 • Listed 2 days

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Welcome to 709 Reed Drive, a classic brick ranch in Frankfort's Cloverdale neighborhood offering plenty of space, a great backyard, and tons of potential! Step inside to a living room filled with natural light from three large windows, plus an eat-in kitchen with a fireplace and room to gather. The main level features beautiful hardwood flooring and so many possibilities to make this space your own! Even better? The HVAC system was replaced this year, and the roof was replaced in 2023, giving you peace of mind with two major updates already taken care of! Bring your vision for the cosmetic updates while enjoying the benefits of these big-ticket improvements. Downstairs, the full unfinished

$269,000

3 beds1.5 baths1,431 sq ft

709 Reed Dr, Frankfort, KY 40601

Hardwood flooring • Hvac system replaced • Natural light

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Nice three bedrooms, bath, living room, eat in kitchen with appliance, family room, patio, large fenced yard and storage building. Hardwood flooring.

$229,900

3 beds1 bath1,506 sq ft

104 Spruce Dr, Frankfort, KY 40601

Fenced yard • Living room • Eat in kitchen

OPEN SAT, 2PM TO 4PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Secluded, Private and Convenient. Enjoy country living with city convenience at 14515 Old Taylorsville Road! Situated on 4.8 acres in a beautiful, private setting, this three-bedroom, two-full-bath ranch offers comfortable single-level living and plenty of room to enjoy the outdoors. Relax on the large deck with your morning coffee, gather with friends, or simply unwind in the peaceful surroundings. There is a detached garage with 3 garage spaces.

$440,000

3 beds2 baths1,590 sq ft

14515 Old Taylorsville Rd, Louisville, KY 40299

Large deck • Private setting • Detached garage

Keller Williams Collective

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Incredible opportunity to own this recently remodeled home in Oldham County. Inside, you will find two bedrooms, comfortable living room, roomy dining room off of the kitchen, and full bathroom on the first floor. The second floor has an additional bedroom with bonus space. The basement, with its separate door access, has many possibilities. Outside, you will find a spacious back yard off of the newly built deck, perfect for entertaining or relaxing. In terms of updates, the roof, furnace, and A/C were all just fully replaced. The entire house has been freshly painted throughout, including the entire basement. The floors and light fixtures have been replaced. The kitchen has a full remodel,

$315,000

3 beds1.5 baths1,220 sq ft

109 Franklin Ave, La Grange, KY 40031

0.26 acre lot • Parking • Built 1946

Gatewood Properties of Kentucky

ABOUT THIS HOME
Vintage Home for sale in Shelby County, KY:
Welcome to 11905 Wetherby Ave, a beautifully renovated 3-bedroom, 1-bath ranch nestled in a quiet, established neighborhood just off Evergreen Road in the heart of Middletown. This move-in ready home offers modern updates while maintaining the comfort and functionality of single-level living. Inside, you'll find a bright, inviting layout with stylish finishes throughout. The spacious backyard provides plenty of room for entertaining, gardening, pets, or simply relaxing outdoors, while the attached 1-car garage adds everyday convenience. Centrally located near shopping, dining, parks, schools, and major highways, this home combines peaceful neighborhood living with easy access to everything

$250,000

3 beds1 bath960 sq ft

11905 Wetherby Ave, Middletown, KY 40243

Easy access • Renovated • Spacious backyard

EXP Realty LLC

Property at 4838 Hickory Ridge Rd, Waddy, KY 40076, 3 beds, 2 baths

$359,900

3 beds2 baths1,700 sq ft

4838 Hickory Ridge Rd, Waddy, KY 40076

Property at 410 Harvest Dr, Taylorsville, KY 40071, 3 beds, 1.5 baths

$264,900

3 beds1.5 baths1,342 sq ft

410 Harvest Dr, Taylorsville, KY 40071

RE/MAX Premier Properties

Property at 219 Merriweather Ave, Eminence, KY 40019, 3 beds, 1 bath

$175,000

3 beds1 bath1,094 sq ft

219 Merriweather Ave, Eminence, KY 40019

Caperton Realty

Property at 11706 Herrick Ln, Middletown, KY 40243, 3 beds, 2 baths

$365,100

3 beds2 baths1,760 sq ft

11706 Herrick Ln, Middletown, KY 40243

Housing Associates

Property at 1911 Old Lawrenceburg Rd, Frankfort, KY 40601, 3 beds, 2 baths

$330,000

3 beds2 baths1,842 sq ft

1911 Old Lawrenceburg Rd, Frankfort, KY 40601

Keller Williams Louisville

Property at 12901 Westport Rd, Louisville, KY 40245, 5 beds, 3 baths

$650,000

5 beds3 baths3,182 sq ft

12901 Westport Rd, Louisville, KY 40245

Kentucky Select Properties

Property at 399 Ewing St, Frankfort, KY 40601, 3 beds, 3 baths

$375,000

3 beds3 baths2,569 sq ft

399 Ewing St, Frankfort, KY 40601

Property at 247 Elm St, Eminence, KY 40019, 2 beds, 1 bath

$175,000

2 beds1 bath1,200 sq ft

247 Elm St, Eminence, KY 40019

KY Homes and Farms Real Estate

Property at 7400 Abbott Ln, Crestwood, KY 40014, 4 beds, 3 baths

$539,000

4 beds3 baths3,004 sq ft

7400 Abbott Ln, Crestwood, KY 40014

DREAM J P Pirtle REALTORS

Property at 540 W Broadway St, Eminence, KY 40019, 2 beds, 1 bath

$175,000

2 beds1 bath855 sq ft

540 W Broadway St, Eminence, KY 40019

Caperton Realty

Property at 201 Van Buren Rd, Mount Eden, KY 40046, 3 beds, 1 bath

$315,000

3 beds1 bath1,975 sq ft

201 Van Buren Rd, Mount Eden, KY 40046

Brown Realty

Property at 3921 W Highway 22, Crestwood, KY 40014, 3 beds, 2 baths

$359,000

3 beds2 baths1,434 sq ft

3921 W Highway 22, Crestwood, KY 40014

OPTL Realty

Property at 12601 N Osage Rd, Anchorage, KY 40223, 4 beds, 3.5 baths

$1,349,900

4 beds3.5 baths4,926 sq ft

12601 N Osage Rd, Anchorage, KY 40223

Homepage Realty

Property at 334 S Bardstown Rd, Mount Washington, KY 40047, 4 beds, 2 baths

$385,000

4 beds2 baths2,148 sq ft

334 S Bardstown Rd, Mount Washington, KY 40047

Semonin Realtors

Vintage Homes for Sale in Shelby County

There are currently 11 vintage homes for sale in Shelby County at a median listing price of $363K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Shelby County stay on the market for 54 days and receive 1 offers. This map is refreshed with the newest listings in Shelby County every 15 minutes.

In the past month, 64 homes have been sold in Shelby County. In addition to houses in Shelby County, there were also 7 condos, 6 townhouses, and 2 multi-family units for sale in Shelby County last month. Find your dream home in Shelby 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 Shelby County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Shelby County. If you're looking to sell your home in the Shelby County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Shelby 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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