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

20 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Home needs doors, trim and cabinets to finish remodeling. Chicken houses are not in use presently but could be used as chicken farm, hydroponics, or livestock. Water and electricity is working in farm houses and they also can be heated with propane.

$755,000

3 beds2 baths1,740 sq ft

2108 Mckendree Chapel Rd, Franklin, KY 42134

Hydroponics • Heated with propane • 30 acre lot

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Experience true country living on 9 peaceful acres while staying only 15 minutes from town. This property offers the best of both worlds: privacy, quiet, and open land, yet still close enough for grocery delivery and DoorDash. A screened in front porch welcomes you with mature shade trees and the perfect spot for morning coffee. Outside, you will find a new livestock barn, a separate shop, and a large garden plot ready for planting. Enjoy summers by the above ground pool with a huge partially covered deck that is ideal for entertaining or relaxing in total tranquility. The roof and siding were replaced in 2021 for added peace of mind. Inside, the home features a new dining room addition fil

$399,900

3 beds2 baths1,422 sq ft

2639 Bracken Prices Mill Rd, Franklin, KY 42134

Bright dining room • Screened porch • New barn

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Welcome to country living at 881 Dinwiddie Road in Franklin, Kentucky! Originally built in 1936, this well-maintained home has been completely and tastefully renovated for modern living while maintaining its charm. Enjoy a generous amount of living space with an oversized family room, a living room, a heated/cooled sunroom, and a separate dining room. The family room and living room each feature a fireplace—one freestanding, and one original. The main floor includes a primary bedroom and full bath, along with an additional bedroom and a half bath off of the dining room. Upstairs features a third bedroom and a full bath, with bonus space that could serve as a pass-through bedroom if ne

$399,900

3 beds2.5 baths2,616 sq ft

881 Dinwiddie Rd, Franklin, KY 42134

Separate dining room • Stylish kitchen • Original fireplace

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Rare find just steps from historic downtown Franklin — 311 W Madison St presents a versatile investment opportunity in a high-traffic, high-visibility location. Whether you’re an investor seeking a strong rental asset, a developer with vision, or an entrepreneur ready to convert to a commercial use, this property delivers location, potential, and value. Situated on a deep lot with easy access to restaurants, shopping, offices, and community amenities, this home offers flexible possibilities including: ? Income-producing rental ? Office, studio, or service-based business ? Rehab/flip with strong ROI potential ? Mixed-use conversion (subject to zoning) Classic character w

$230,000

3 beds1 bath1,540 sq ft

311 W Madison St, Franklin, KY 42134

6,098 sq ft lot • Built 1850 • Listed 11 days

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Completely Renovated Home on 2 Acres Just Minutes From Downtown Franklin! Discover the perfect blend of convenience, privacy, and brand-new updates at 908 W Cedar St in Franklin, KY. Located less than 2 minutes from the square, 30 minutes to Bowling Green, and 50 minutes to downtown Nashville, this fully renovated home offers modern living with an unbeatable location. Sitting on 2 beautiful acres, the property features a freshly painted workshop/barn, plenty of open space, and a peaceful wooded grove that brings privacy and frequent wildlife sightings. Inside, this home has been completely transformed from top to bottom. Updates include: New subfloor New HVAC New electrical throughout New

$399,900

3 beds3 baths1,992 sq ft

908 W Cedar St, Franklin, KY 42134

New pex plumbing • Fully renovated home • New hvac

Property at 608 Brevard St, Franklin, KY 42134, 2 beds, 2 baths

$169,900

2 beds2 baths1,078 sq ft

608 Brevard St, Franklin, KY 42134

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 625 Brevard St, Franklin, KY 42134, 3 beds, 1 bath

$199,900

3 beds1 bath943 sq ft

625 Brevard St, Franklin, KY 42134

Property at 1021 Henson Rd, Bowling Green, KY 42104, 2 beds, 1.5 baths

$250,000

2 beds1.5 baths1,352 sq ft

1021 Henson Rd, Bowling Green, KY 42104

Property at 102 Schweizer Rd, Franklin, KY 42134, 3 beds, 1 bath

$224,000

3 beds1 bath1,109 sq ft

102 Schweizer Rd, Franklin, KY 42134

Property at 301 N College St, Franklin, KY 42134, 2 beds, 1 bath

$239,500

2 beds1 bath1,542 sq ft

301 N College St, Franklin, KY 42134

Property at 300 S College St, Franklin, KY 42134, 3 beds, 2 baths

$274,900

3 beds2 baths1,952 sq ft

300 S College St, Franklin, KY 42134

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 417 Morris St, Franklin, KY 42134, 2 beds, 1 bath

$189,900

2 beds1 bath887 sq ft

417 Morris St, Franklin, KY 42134

Property at 231 S College St, Franklin, KY 42134, 4 beds, 4.5 baths

$339,900

4 beds4.5 baths3,347 sq ft

231 S College St, Franklin, KY 42134

Property at 501 S College St, Franklin, KY 42134, 3 beds, 2 baths

$235,000

3 beds2 baths1,650 sq ft

501 S College St, Franklin, KY 42134

Property at 810 Western Dr, Franklin, KY 42134, 4 beds, 2 baths

$290,000

4 beds2 baths1,806 sq ft

810 Western Dr, Franklin, KY 42134

Property at 521 E Cedar St, Franklin, KY 42134, 3 beds, 1 bath

$207,500

3 beds1 bath1,938 sq ft

521 E Cedar St, Franklin, KY 42134

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 301 W Cedar St, Franklin, KY 42134, 4 beds, 3 baths

$399,900

4 beds3 baths2,544 sq ft

301 W Cedar St, Franklin, KY 42134

Property at 5320 Morgantown Rd, Franklin, KY 42134, 1 bath

$2,795,375

— beds1 bath1,384 sq ft

5320 Morgantown Rd, Franklin, KY 42134

Property at 1014 W Cedar St, Franklin, KY 42134

$67,950

— beds— baths— sq ft

1014 W Cedar St, Franklin, KY 42134

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 548 Vances Mill Rd, Franklin, KY 42134

$260,000

— beds— baths— sq ft

548 Vances Mill Rd, Franklin, KY 42134

Listing provided by REALTRACS as Distributed by MLS Grid

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Country living with character! Pre-civil war historic farmhouse- Horse Farm- Vacation Rental. The opportunities abound. One-of-a-kind property that included a gourmet kitchen, dreamy screen porch, soaking tub in master bath, open air side deck, and recently added fire pit area. The home features mini split air units in each room for individual comfort. Chimney in living room was rebuild/rebricked, living room floor recently replaced and crawl space encapsulated. Sunsets await you to enjoy this peaceful country setting. The large, freshly painted barn includes 8 horse stalls, workshop, and ventilated hay loft. A short walk into the woods leads to the winding creek. This beautiful escape is t

$1,250,000

3 beds2 baths2,424 sq ft

2060 Luther Herald Rd, Franklin, KY 42134

Soaking tub • Gourmet kitchen • Fire pit area

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Simpson County, TN:
Welcome to 620 Cooks Road in Portland, Tennessee, where peaceful country living meets modern comfort. This charming three-bedroom, two-bath brick home sits on a spacious lot surrounded by mature trees and open skies, offering both privacy and convenience. Inside, natural light fills the rooms, highlighting the fresh flooring, crown molding, and cozy fireplace. The living area flows easily into a bright kitchen featuring granite countertops, a large center island, pendant lighting, and crisp white cabinets. The dining area overlooks the yard, making it perfect for casual meals or family gatherings. The primary suite offers a quiet retreat with a private bath, while the additional bedrooms pr

$535,000

4 beds3 baths2,750 sq ft

620 Cook Rd, Portland, TN 37148

Large center island • Private bath • Crisp white cabinets

Listing provided by REALTRACS as Distributed by MLS Grid

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Back on the market with no fault of it's own! Nestled in the heart of Auburn sits this charming historical home on a corner lot boasting 5 bedrooms, 4 bathrooms, and over 3,200 square feet! This home is a perfect blend of history with a modern touch including older architecture and a tastefully updated kitchen, along with custom tiled bathrooms, newer paint, newer flooring, and so much more! Conveniently located across the street from Auburn Elementary, and has an attached 2-car carport and side covered porch. There is SO much to say about this home, come see for yourself! * Some photos are virtually staged *

$267,500

5 beds4 baths3,247 sq ft

614 Maple St, Auburn, KY 42206

Historical home • Attached carport • Side covered porch

ABOUT THIS HOME
Vintage Home for sale in Simpson County, TN:
Amazing opportunity to own a piece of history with almost 8 acres of flat usable land and a pond! Complete privacy - surrounded by woods on all 4 sides! Main part of the house is original historical log home with a concrete cellar. Home has 4 bedrooms and 2 full bathrooms. Owner suite with private bath/walk in closet is on the first floor. Only upstairs bedroom is oversized and could be 2 bedrooms. There is a building approximately 25x40 that had a separate meter with water already ran. It would make a great income producer if you got it approved as a DADU or Peerspace rental. Meter was pulled for non-use so needs a CEMC inspection to put back. Water runs to building, but winterized so tu

$439,900

4 beds2 baths2,170 sq ft

5444 E Robertson Rd, Orlinda, TN 37141

7.76 acre lot • 10 parking spots • Built 1924

Listing provided by REALTRACS as Distributed by MLS Grid

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
beautifully restored home built in 1886. Three large bedrooms, one downstairs and 2 upstairs. There is a common half bathroom downstairs, plus an ensuite bathroom in the downstairs bedroom. Upstairs, the two bedrooms share a common bathroom. The large back yard is suitable for a garden. The huge front porch is ideal for whiling away the lazy afternoons. Downstairs boasts a living room, a dining area and a kitchen with granite countertops! This well insulated home has modern mini-splits for the ultimate in comfort. Located in the highly sought after South Warren school district, at a price point that won& apos; t break the bank!

$260,000

3 beds1 bath2,231 sq ft

143 Main St, Woodburn, KY 42170

Modern mini-splits • Huge front porch • Common half bathroom

ABOUT THIS HOME
Vintage Home for sale in Simpson County, KY:
Located just off Main St and an easy walk to Downtown Auburn this home offers a large yard and a lot of interior space. The front porch is fully enclosed; the family room has laminate floors and a fireplace. It has two main level bedrooms, and the upstairs is mostly finished for an additional bedroom and office/living room. There are two outside storage buildings and a concrete pad for a carport or garage. This home needs some work but has good potential.

$139,900

2 beds2 baths1,615 sq ft

242 S Lincoln St, Auburn, KY 42206

Laminate floors • Concrete pad • Large yard

Property at 2944 Woodburn Allen Springs Rd, Bowling Green, KY 42104, 3 beds, 1.5 baths

$278,900

3 beds1.5 baths1,944 sq ft

2944 Woodburn Allen Springs Rd, Bowling Green, KY 42104

Property at 204 Wilson Ave, Auburn, KY 42206, 3 beds, 2 baths

$245,000

3 beds2 baths1,353 sq ft

204 Wilson Ave, Auburn, KY 42206

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1200 N Church St, Portland, TN 37148, 2 beds, 1 bath

$149,000

2 beds1 bath1,556 sq ft

1200 N Church St, Portland, TN 37148

Listing provided by REALTRACS as Distributed by MLS Grid

Vintage Homes for Sale in Simpson County

There are currently 20 vintage homes for sale in Simpson County at a median listing price of $292K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Simpson County stay on the market for 107 days and receive 1 offers. This map is refreshed with the newest listings in Simpson County every 15 minutes.

In the past month, 13 homes have been sold in Simpson County. In addition to houses in Simpson County, there were also 0 condos, 1 townhouse, and 4 multi-family units for sale in Simpson County last month. Find your dream home in Simpson 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 Simpson County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Simpson County. If you're looking to sell your home in the Simpson County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Simpson County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Simpson County, KY

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Simpson County, KY

How to buy a house in Simpson County, KY

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Kentucky

Based on information submitted to the MLS GRID as of Sat Dec 13 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.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.