Chester County, TN homes for sale & real estate

102 homes

Sort:

Recommended

Lot 23 Timberwood Cv, Henderson, TN 38340
Lot 23 Timberwood Cv, Henderson, TN 38340
Lot 23 Timberwood Cv, Henderson, TN 38340
ABOUT THIS HOME
Chester County, TN Homes for Sale
Nice residential lot in great location! This 1.18 ac lot in Creekside Estates is waiting for your dream home!

$22,000

— beds— baths— sq ft

Lot 23 Timberwood Cv, Henderson, TN 38340

1.18 acre lot • Car-dependent

Lot 22 Timberwood Cv, Henderson, TN 38340
Lot 22 Timberwood Cv, Henderson, TN 38340
Lot 22 Timberwood Cv, Henderson, TN 38340
ABOUT THIS HOME
Chester County, TN Homes for Sale
Nice residential lot in great location! This 1.3 acre vacant lot in Creekside Estates is ready for your dream home!

$22,000

— beds— baths— sq ft

Lot 22 Timberwood Cv, Henderson, TN 38340

1.3 acre lot • Car-dependent

1450 Busby Ln, Henderson, TN 38340
1450 Busby Ln, Henderson, TN 38340
1450 Busby Ln, Henderson, TN 38340
ABOUT THIS HOME
Chester County, TN Homes for Sale
Rolling fields, open pasture, and scattered wooded areas create a diverse landscape that's both functional and beautiful. Whether you're looking to cultivate crops, raise animals, or simply enjoy wide-open spaces, this land offers both privacy and potential. Complete with a classic barn, perfect for storage, livestock, or conversion into a workshop, 2 active wells, and 3 manufactured trailers for potential rental income. Call me for details!

$503,500

— beds— baths— sq ft

1450 Busby Ln, Henderson, TN 38340

91.7 acre lot • Car-dependent

2865 Deanburg Rd, Medon, TN 38356
2865 Deanburg Rd, Medon, TN 38356
2865 Deanburg Rd, Medon, TN 38356
ABOUT THIS HOME
Chester County, TN Homes for Sale
Opportunity awaits on this 12.17-acre tract of unrestricted land—perfect for building, investing, or simply enjoying peaceful country living. With two scenic potential building sites—one overlooking the pond and another tucked just inside the woods—this property offers space and versatility for your vision. Hardwoods cover most of the acreage, adding privacy and natural beauty, while electricity is available at both homesites, saving you time and expense. Located only 15 minutes from Jackson and Henderson, and just 5 minutes from Chickasaw State Park, you'll love the balance of seclusion and convenience. Whether you're dreaming of a custom home, hobby farm, or quiet getawa

$94,000

— beds— baths— sq ft

2865 Deanburg Rd, Medon, TN 38356

12.17 acre lot • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

0 Tn-125, Henderson, TN 38340
0 Tn-125, Henderson, TN 38340
0 Tn-125, Henderson, TN 38340
ABOUT THIS HOME
Chester County, TN Homes for Sale
4 Acres of Country Charm Escape to the peace and quiet of the countryside with this beautiful 4-acre property featuring a serene pond, a rustic old barn, and a mix of open space and wooded areas. Perfect for a weekend retreat, future homesite, or hobby farm—this land offers endless potential in a tranquil setting. Plenty of hunting opportunity for the outdoorsman with deer tracks abundant. Located right beside Chickasaw State Forrest and right around the corner from the golf course! 4 Acres of Country Charm Escape to the peace and quiet of the countryside with this beautiful 4-acre property featuring a serene pond, a rustic old barn, and a mix of open space and wooded areas. Perfect

$52,900

— beds— baths— sq ft

0 Tn-125, Henderson, TN 38340

4 acre lot • Car-dependent

Property at 305 Smith Rd, Luray, TN 38352

$235,000

— beds— baths— sq ft

305 Smith Rd, Luray, TN 38352

Property at Tract 5 S State Route 22 A, Enville, TN 38332

$68,000

— beds— baths— sq ft

Tract 5 S State Route 22 A, Enville, TN 38332

Property at Tract 4 S State Route 22a, Enville, TN 38332

$62,000

— beds— baths— sq ft

Tract 4 S State Route 22a, Enville, TN 38332

Property at Tract 3 S State Route 22 A, Enville, TN 38332

$58,500

— beds— baths— sq ft

Tract 3 S State Route 22 A, Enville, TN 38332

Property at 000 Morgan St, Henderson, TN 38340

$199,900

— beds— baths— sq ft

000 Morgan St, Henderson, TN 38340

Property at 0 Meadowlands Ln, Henderson, TN 38340

$25,000

— beds— baths— sq ft

0 Meadowlands Ln, Henderson, TN 38340

Listing provided by REALTRACS as Distributed by MLS Grid

Property at Vida Rd, Beech Bluff, TN 38313

$16,500

— beds— baths— sq ft

Vida Rd, Beech Bluff, TN 38313

$59,999

— beds— baths— sq ft

0 Smith Rd, Luray, TN 38352

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 0 Roby Trl, Henderson, TN 38340

$469,385

— beds— baths— sq ft

0 Roby Trl, Henderson, TN 38340

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 285 Sherry Ln, Enville, TN 38332

$44,900

— beds— baths— sq ft

285 Sherry Ln, Enville, TN 38332

Property at 823 Us Highway 45 N, Henderson, TN 38340

$950,000

— beds— baths— sq ft

823 Us Highway 45 N, Henderson, TN 38340

Property at 817 Hill, Henderson, TN 38340

$372,000

— beds— baths— sq ft

817 Hill, Henderson, TN 38340

Property at 000 Sweetlips Rd, Henderson, TN 38340

$79,900

— beds— baths— sq ft

000 Sweetlips Rd, Henderson, TN 38340

Property at 00 Newsome Ave, Henderson, TN 38340

$750,000

— beds— baths— sq ft

00 Newsome Ave, Henderson, TN 38340

Property at 00 Deerfield Loop, Henderson, TN 38340

$20,000

— beds— baths— sq ft

00 Deerfield Loop, Henderson, TN 38340

Viewing page 3 of 3

Average home prices near Chester County, TN

Cities

Counties

Perry County homes for sale
$249,900
Madison County homes for sale
$325,000
Humphreys County homes for sale
$349,000

Chester County, TN real estate trends

All Home Types trends in Chester County, TN

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$232,500

+24.5% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Chester County, TN

$232,500

+24.5%

See more Chester County, TN market insights

More to explore in Chester County, TN

How to buy a house in Chester County, TN

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 Tennessee

Based on information submitted to the MLS GRID as of Tue Jul 22 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

Countries

United States

Canada

Updated January 2023: 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, TITLE FORWARD, 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

Rocket Mortgage is an affiliated business of Redfin. 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. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).

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.