Vintage homes for sale & real estate in Chester County, TN

15 homes

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ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Spacious 3,780 sq. ft. home featuring 4 bedrooms and 2.5 baths with plenty of extra space throughout. The main level offers 3 bedrooms, 2 full baths, and a large bonus room on the back of the home—perfect for a family room or game area. Upstairs includes an additional bedroom, half bath, and a generous storage area. The fenced backyard includes a storm shelter and is ideal for pets or outdoor entertaining. Conveniently located in town, close to shopping, schools, and amenities.

$294,900

4 beds2.5 baths3,780 sq ft

524 Hill Ave, Henderson, TN 38340

Close to schools • Large bonus room • Storm shelter

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Home comes with a Home Warranty. Welcome to 5060 Enville Rd. Henderson, TN. This charming 3bed 2bath farmhouse seamlessly blends comfort with rustic appeal. This home highlights a huge master bedroom perfect for your retreat after a busy day, a brand new roof that ensures years of worry-free living, 2 acres of beautiful landscape, a poultry coop and a workshop with electricity ready for any DIY projects. Whether you dream of starting a mini-homestead, need ample space for tools and toys, or simply crave the tranquility of country life, this property delivers it all. Call to schedule your private tour today!

$215,500

3 beds2 baths1,600 sq ft

5060 Enville Rd, Henderson, TN 38340

Brand new roof • Poultry coop • 2 acre lot

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Charming 2-Bed, 2-Bath Home in Henderson, Tennessee! Welcome to this well-maintained home featuring an open floor plan and luxury vinyl plank flooring throughout. The kitchen comes fully equipped with stainless steel appliances—including a built-in microwave, dishwasher, refrigerator, and electric oven with cooktop—plus new custom cabinetry. Enjoy the convenience of a dedicated laundry area, ample pantry space, and a desirable corner lot location. This move-in-ready home perfectly blends comfort and convenience—schedule your showing today!

$179,900

2 beds2 baths1,203 sq ft

462 Mifflin Ave, Henderson, TN 38340

Custom cabinetry • Open floor plan • Built-in microwave

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Calling all investors! Possibilities are endless. Home is in need of extensive repairs. 3 bedrooms, 1 and half bath, laundry room, storm shelter, and a big backyard.

$45,000

3 beds1.5 baths1,152 sq ft

132 Whitley Ave, Henderson, TN 38340

Big backyard • Laundry room • Storm shelter

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Are you looking for a large tract of land with lots of road frontage? Look no further than this 175 acre tract of land located on both sides of Highway 22. Property has at over 5000 ft of road frontage. Land is mainly wooded. Jacks Creek runs behind the implement shed. This property also has a dwelling, but home is inhabitable at this time. There is also a well on the property. New survey was recently done of the property. There is also a 40x40 implement shed on the property that was built in 2017. Property is being sold As-IS. Video on BST Realty Youtube channel.

$619,900

3 beds3 baths1,575 sq ft

495 Tn-22 Alt Hwy, Jacks Creek, TN 38347

40x40 implement shed • Well on the property • 175 acre tract

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1675 Emerson Rd, Henderson, TN 38340, 2 beds, 2 baths

$185,000

2 beds2 baths1,168 sq ft

1675 Emerson Rd, Henderson, TN 38340

Property at 328 Baughn St, Henderson, TN 38340, 2 beds, 1 bath

$99,900

2 beds1 bath768 sq ft

328 Baughn St, Henderson, TN 38340

Property at 129 N Carolina Ave, Henderson, TN 38340, 3 beds, 2 baths

$165,777

3 beds2 baths2,366 sq ft

129 N Carolina Ave, Henderson, TN 38340

Property at 263 North Ave, Henderson, TN 38340, 3 beds, 2 baths

$229,900

3 beds2 baths1,697 sq ft

263 North Ave, Henderson, TN 38340

Property at 320 Rabbit Ranch Rd, Henderson, TN 38340, 4 beds, 2 baths

$525,000

4 beds2 baths2,744 sq ft

320 Rabbit Ranch Rd, Henderson, TN 38340

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1341 Old Jacks Creek Rd, Henderson, TN 38340, 3 beds, 1.5 baths

$189,900

3 beds1.5 baths1,526 sq ft

1341 Old Jacks Creek Rd, Henderson, TN 38340

Property at 511 White Ave, Henderson, TN 38340, 3 beds, 3 baths

$295,000

3 beds3 baths2,312 sq ft

511 White Ave, Henderson, TN 38340

Property at 1295 Mayfield Rd, Henderson, TN 38340, 3 beds, 1.5 baths

$157,400

3 beds1.5 baths960 sq ft

1295 Mayfield Rd, Henderson, TN 38340

Property at 180 State Rte 22a S, Jacks Creek, TN 38347, 3 beds, 2 baths

$174,900

3 beds2 baths1,536 sq ft

180 State Rte 22a S, Jacks Creek, TN 38347

Property at 2160 Jones Rd, Luray, TN 38352, 2 beds

$59,900

2 beds— baths1,864 sq ft

2160 Jones Rd, Luray, TN 38352

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ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Investor special! Duplex in Lana area on Lambuth Blvd, next to University of Memphis, with brand-new roof, all new windows, new deck, and fresh exterior paint. Interior has been demoed—ready for you to design as a duplex or convert into a single-family home. Prime location near downtown, close to all the restaurants like Blacksmith, Rock n Dough pizza, Hub city Brewery, Lift Wellness Centre, Grubbs, schools, and shopping. This Solid brick home with unfinished basement and new electrical and plumbing wouldn't last longer!

$149,000

2 beds— baths1,650 sq ft

425 Lambuth Blvd, Jackson, TN 38301

6,750 sq ft lot • 2 parking spots • Built 1931

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Comfortable 3 bedrooms, 2 full bathrooms in approximately 1,240 sq ft of living area. Built in 1945, offering character and solid bones. Lot size approximately 0.53 acres Recent updates: New Roof-2025, HVAC in 2017, Convenient off-street parking (5 spaces noted) and home sits on a corner lot. Great opportunity for first-time homebuyer or investor — move-in ready with many updates already completed. Located in the heart of Jackson (zip 38301)

$85,000

3 beds1.5 baths1,240 sq ft

131 Whitehall St, Jackson, TN 38301

Hvac • Off-street parking • New roof

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
124 Glendale Street, a freshly updated 3-bedroom, 2-bath, 1,700sqft home that's move-in ready. The roof is only about 5 years old, and the HVAC system and furnace were both replaced roughly 2-3 years ago. The windows were updated just 3 years ago as well, which helps keep energy costs down. The dining room floor was replaced about 3 years ago, the kitchen was updated around the same time, and the bathroom received a refresh just 2 years ago. Plumbing and electrical has been replaced in the last 5 years. Conveniently located in Jackson's 38301 area, the home is close to downtown restaurants, shopping, parks, and everyday essentials. It's also near Arlington Elementary, North Parkway Middle,

$179,900

3 beds2 baths1,697 sq ft

124 Glendale St, Jackson, TN 38301

Updated windows • Updated kitchen • Replaced plumbing

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
This adorable 2 bedroom, 1 bathroom home is a delight, featuring a formal dining room perfect for special occasions and an updated kitchen equipped with appliances for easy cooking. Outside, enjoy additional amenities like a double carport canopy for protected parking, a spacious 2-car shop for hobbies or storage, and a separate storage building for extra organization. Best of all, this property includes TWO extra lots, offering endless possibilities for expansion, gardening, or simply enjoying extra outdoor space!

$139,900

2 beds1 bath— sq ft

431 Bethel Purdy Rd, Bethel Springs, TN 38315-3532

Formal dining room • Two extra lots • Updated kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Answer the call of country living with this charming 2-bedroom, 1-bath retreat in Bethel Springs, TN! Sitting on nearly an acre, this cozy gem has been given a fresh glow-up with new paint, new flooring, a brand-new touch screen cooktop, and a sleek mini-split system for all-season comfort. The bonus shop/garage is perfect for projects, storage, or hobbies, while the spacious yard invites gardening, play, or future expansion. Whether you’re starting out, settling down, or investing smart, this country home is ready to impress!

$125,000

2 beds1 bath— sq ft

1907 Elmer Cox Rd, Bethel Springs, TN 38315

Fresh glow-up • Mini-split system • New flooring

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Step into the charm of this beautifully updated early-1900s Victorian situated on a generous corner lot in the heart of Jackson. With its classic wraparound porch, architectural gables, and bold exterior colors, this home delivers the character buyers want—paired with the modern updates they expect. Inside, you'll find high ceilings, wide moldings, original hardwood floors, and multiple large rooms that offer flexible living and dining spaces. The front rooms are filled with natural light from tall windows and feature fresh interior paint, updated lighting, and preserved architectural details. The remodeled kitchen is a standout, offering new cabinetry, butcher-block countertops, stai

$349,900

5 beds3 baths3,546 sq ft

1072 N Highland Ave, Jackson, TN 38301

Architectural gables • Remodeled kitchen • Farmhouse sink

Property at 2884 Sandy Flat Rd, Bethel Springs, TN 38315, 4 beds, 1.5 baths

$289,000

4 beds1.5 baths1,778 sq ft

2884 Sandy Flat Rd, Bethel Springs, TN 38315

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 516 Greenwood Ave, Jackson, TN 38301, 2 beds, 1 bath

$79,000

2 beds1 bath900 sq ft

516 Greenwood Ave, Jackson, TN 38301

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 152 Seavers Rd, Jackson, TN 38301, 2 beds, 1 bath

$179,900

2 beds1 bath1,355 sq ft

152 Seavers Rd, Jackson, TN 38301

Property at 381 Chester Levee Rd, Jackson, TN 38301, 3 beds, 2 baths

$235,000

3 beds2 baths1,798 sq ft

381 Chester Levee Rd, Jackson, TN 38301

Property at 48 Old Henderson Rd, Pinson, TN 38366, 4 beds, 2 baths

$139,900

4 beds2 baths1,508 sq ft

48 Old Henderson Rd, Pinson, TN 38366

Property at 107 Newton St, Jackson, TN 38301, 3 beds, 3 baths

$260,000

3 beds3 baths1,751 sq ft

107 Newton St, Jackson, TN 38301

Property at 123 Woodhaven Dr, Jackson, TN 38301, 4 beds, 4 baths

$439,900

4 beds4 baths3,778 sq ft

123 Woodhaven Dr, Jackson, TN 38301

Property at 240 S Oak St, Adamsville, TN 38310, 3 beds, 1 bath

$199,000

3 beds1 bath— sq ft

240 S Oak St, Adamsville, TN 38310

Property at 402 Fairmont Ave, Jackson, TN 38301, 3 beds, 1 bath

$99,000

3 beds1 bath1,528 sq ft

402 Fairmont Ave, Jackson, TN 38301

Property at 559 N Cumberland St, Jackson, TN 38301, 3 beds, 1 bath

$47,000

3 beds1 bath1,147 sq ft

559 N Cumberland St, Jackson, TN 38301

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 124 Taylor St, Jackson, TN 38301, 3 beds, 1 bath

$43,900

3 beds1 bath1,232 sq ft

124 Taylor St, Jackson, TN 38301

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 133 Division Ave, Jackson, TN 38301, 3 beds, 2 baths

$229,900

3 beds2 baths2,008 sq ft

133 Division Ave, Jackson, TN 38301

Property at 322 Arlington Ave, Jackson, TN 38301, 4 beds, 3 baths

$179,000

4 beds3 baths2,024 sq ft

322 Arlington Ave, Jackson, TN 38301

Property at 8069 Old Stage Rd, Adamsville, TN 38310

$85,000

— beds— baths— sq ft

8069 Old Stage Rd, Adamsville, TN 38310

Listing provided by REALTRACS as Distributed by MLS Grid

Vintage Homes for Sale in Chester County

There are currently 15 vintage homes for sale in Chester County at a median listing price of $269K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester County stay on the market for 88 days. This map is refreshed with the newest listings in Chester County every 15 minutes.

In the past month, 12 homes have been sold in Chester County. In addition to houses in Chester County, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Chester County last month. Find your dream home in Chester 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 Chester County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester County. If you're looking to sell your home in the Chester County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester 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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Based on information submitted to the MLS GRID as of Sat Nov 29 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.

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