Chester County, TN Homes

/19
$257,000
- 3 Beds
- 3 Baths
- 3,054 Sq Ft
4925 State Route 225, Henderson, TN 38340

This 3,054 sq. ft. brick home offers plenty of space inside and out, all situated on 2.05 acres! Featuring 3 bedrooms with the potential for a 4th and 3 full baths, this home has a spacious eat-in kitchen, separate dining room, and inviting living room with fireplace. The oversized primary suite offers plenty of room to relax and includes a private bath with a whirlpool tub and separate shower.

Tiffany Jones

Tiffany Jones Realty Group

4925 State Route 225, Henderson, TN 38340
/6
$1,050 Per Month
- 2 Beds
- 1 Bath
- Apartment for Rent
320 Samantha Cove, Henderson, TN 38340

Discover your serene retreat in this 2 bedroom, 1 bathroom duplex, boasting a peaceful atmosphere and convenient location. The interior boasts sleek LVP flooring in the living room, bathroom, and kitchen, plus fresh paint throughout. The kitchen is equipped with appliances for effortless meal prep. Ample parking space is available, and lawn maintenance is included for added convenience. This is a

Brooke Redmon Benton Action Realty

320 Samantha Cove, Henderson, TN 38340
/18
$400,000

Sold Oct 29, 2025

1450 Busby Ln, Henderson, TN 38340
- Land
- 91.7 Acres
- $4,362 per Acre
Last Sold Summary
- 21% Below List Price
- 153 Days On Market
Last Listing Agent Robert Eatman Hickman Realty Group Inc.-Jack

1450 Busby Ln, Henderson, TN 38340

/27
Est $249,218

Not Listed For Sale

195 Simmons St, Henderson, TN 38340
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
- Built 2015
195 Simmons St, Henderson, TN 38340

Last Sold Summary
- 252 Days On Market
Last Listing Agent Destiny Burns Stellar Realty Group

/2
$37,500
- Land
- 0 Sq Ft
00 Barham Ave, Henderson, TN 38340

Great lot to build your dream home in Chester County. Great schools and family friendly community. Call Melanie at 731.879.9655

Melanie Malone

Crye-Leike Elite

00 Barham Ave, Henderson, TN 38340
/2
$30,000

Sold Nov 05, 2025

4875 Clifford Rd, Luray, TN 38352
- Land
- 6.28 Acres
- $4,777 per Acre
Last Sold Summary
Current Estimated Value $99,598

Last Listing Agent Brandi Ragan Ragan Realty Group

4875 Clifford Rd, Luray, TN 38352

/14
Est $234,572

Not Listed For Sale

870 Simmons Rd, Henderson, TN 38340
- 3 Beds
- 2 Baths
- 1,358 Sq Ft
- Built 2009
870 Simmons Rd, Henderson, TN 38340

Last Sold Summary
- 69 Days On Market
Last Listing Agent Aaliyah Cupples Stellar Realty Group

/8
$42,000
- Land
- 2.12 Acres
- $19,811 per Acre
Lot 8 Greystone Cove, Henderson, TN 38340

Greystone Estates presents Lot 8! This beautiful 3.12-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

Destiny Burns

Stellar Realty Group

Lot 8 Greystone Cove, Henderson, TN 38340
/14
$235,000

Sold Sep 10, 2025

1280 Mockingbird Rd, Medon, TN 38356
- 2 Beds
- 2 Baths
- 1,388 Sq Ft
- Built 1995
Last Sold Summary
- 3% Above List Price
- $169/SF
- 0 Days On Market
Current Estimated Value $231,953

Last Listing Agent Brandi Isom RE/MAX Realty Source

1280 Mockingbird Rd, Medon, TN 38356

/29
Est $226,667

Not Listed For Sale

948 Sand Ave, Henderson, TN 38340
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
- Built 1979
948 Sand Ave, Henderson, TN 38340

Last Sold Summary
- 6 Days On Market
Last Listing Agent Linda Carter Casey Realtors

/31
$70,000

Pending
- 3 Beds
- 2 Baths
- 2,009 Sq Ft
425B Second St, Henderson, TN 38340

Rare investment opportunity in the heart of Henderson! This historic home sits on approximately 1.2 acres in an established neighborhood and offers tremendous potential. The home was damaged by fire several years ago and is being sold as-is, but much of the structure remains, making it a strong candidate for restoration by the right contractor. The oversized lot also presents excellent

Joshua Trammell

EXIT Realty Blues City

425B Second St, Henderson, TN 38340
/3
$35,000

Sold Sep 03, 2025

0 LOT 2 W 3rd St, Henderson, TN 38340
- Land
- 0 Sq Ft
Last Sold Summary
- 3% Below List Price
- 0 Days On Market
Last Listing Agent Linda Carter Casey Realtors

0 LOT 2 W 3rd St, Henderson, TN 38340

/15
Est $298,868

Not Listed For Sale

540 Moss Loop, Enville, TN 38332
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 2009
540 Moss Loop, Enville, TN 38332

Last Sold Summary
- 158 Days On Market
Last Listing Agent Brandi Isom RE/MAX Realty Source

/2
$50,000
- Land
- 6.35 Acres
- $7,874 per Acre
0 Old Sobby Rd, Bethel Springs, TN 38315

Beautiful wooded acreage, perfect for building your perfect country dreamhome! Land is directly across from 130 Old Sobby Road that is listed for sale. MLS #2502842

Brandi Isom

RE/MAX Realty Source

0 Old Sobby Rd, Bethel Springs, TN 38315
/5
$20,000

Sold Aug 14, 2026

Lot 21 Timberwood Cove, Henderson, TN 38340
- Land
- 1.3 Acres
- $15,385 per Acre
Last Sold Summary
- 43% Below List Price
- 348 Days On Market
Last Listing Agent Zach Hannis Casey Realtors

Lot 21 Timberwood Cove, Henderson, TN 38340

/25
Est $221,027

Not Listed For Sale

75 Bray Ln, Beech Bluff, TN 38313
- 3 Beds
- 2 Baths
- 1,238 Sq Ft
- Built 2009
75 Bray Ln, Beech Bluff, TN 38313

Last Sold Summary
- 29 Days On Market
Last Listing Agent Destiny Burns Stellar Realty Group

/38
$579,900

Open Sun 2PM - 4PM $20K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,642 Sq Ft
3290 Silerton Rd, Henderson, TN 38340

Exquisite custom built home in Chester County with 3 car garage on 10 acres! This open floorplan offers a chefs dream kitchen with high end stainless appliances, large great room for entertaining with corner gas fireplace, tankless water heater, upgraded sprayed foam insulation for efficiency, lots of outdoor entertaining areas including covered front and back porches and side court yard area. So

Ben Roberts

RE/MAX Realty Source

3290 Silerton Rd, Henderson, TN 38340
/34
$310,000

Sold Jul 27, 2026

185 Leath Ln, Finger, TN 38334
- 3 Beds
- 2.5 Baths
- 2,156 Sq Ft
- Built 2006
Last Sold Summary
- 10% Below List Price
- $144/SF
- 79 Days On Market
Current Estimated Value $335,732

Last Listing Agent Melanie Cromwell BST Realty

185 Leath Ln, Finger, TN 38334

/23
Est $250,525

Not Listed For Sale

290 Bray Ln, Beech Bluff, TN 38313
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
- Built 2009
290 Bray Ln, Beech Bluff, TN 38313

Last Sold Summary
- 30 Days On Market

/9
$19,900
- Land
- 1 Acre
- $19,900 per Acre
285 Cedar Brook Ln, Henderson, TN 38340

Build the home you've been dreaming of in beautiful Hidden Hills Estates! This 1-acre building lot offers the perfect setting for a basement home, with a gentle slope that creates ideal elevation and design opportunities. Tucked at the back of the property, Tar Creek runs behind the lot, adding a peaceful natural backdrop and enhancing the privacy this homesite provides. Wildlife is

Brandi Isom

RE/MAX Realty Source

285 Cedar Brook Ln, Henderson, TN 38340
/34
$205,000

Sold Oct 06, 2025

175 S State Route 22a S St, Jacks Creek, TN 38347
- 3 Beds
- 2 Baths
- 2,146 Sq Ft
- Built 1900
Last Sold Summary
- 37% Below List Price
- $96/SF
Current Estimated Value $178,269

175 S State Route 22a S St, Jacks Creek, TN 38347

/36
Est $274,309

Not Listed For Sale

280 Bray Ln, Beech Bluff, TN 38313
- 3 Beds
- 2 Baths
- 1,545 Sq Ft
- Built 2009
280 Bray Ln, Beech Bluff, TN 38313

Last Sold Summary
- 76 Days On Market
Last Listing Agent Non-TVAR Agent Non-TVAR Agency

/13
$225,550
- Land
- 45.11 Acres
- $5,000 per Acre
0 Highway 22 A, Enville, TN 38332

Escape to Tennessee Country Living on this 45.11 parcel situated in Enville, TN. Ideally located just 20 miles from Lexington, Henderson, and Savannah, TN, this property offers no restrictions and lies outside city limits, giving you the perfect chance to make your dreams come true. Part of tract has already been cleared and ready to build on. Soil mapping has been done. Call today!

Lori Yarbro

Evans Real Estate

0 Highway 22 A, Enville, TN 38332
/20
$158,000

Sold Jun 30, 2026

11350 State Route 100 E, Reagan, TN 38368
- 1 Bed
- 1 Bath
- 1,387 Sq Ft
- Built 2004
Last Sold Summary
- 15% Below List Price
- $114/SF
- 52 Days On Market
Current Estimated Value $176,257

Last Listing Agent Jennifer Greer Greer Real Estate Group

11350 State Route 100 E, Reagan, TN 38368

/51
Est $258,519

Not Listed For Sale

280 Bray Rd, Beech Bluff, TN 38313
- Studio
- 1,518 Sq Ft
- Built 2009
280 Bray Rd, Beech Bluff, TN 38313

Last Sold Summary
- 49 Days On Market
Last Listing Agent Chris Miller Crye-Leike Elite

/82
$574,900
- 3 Beds
- 2.5 Baths
- 3,786 Sq Ft
231 Mitchell St, Henderson, TN 38340

Imagine starting your morning with a cup of coffee on the back patio, overlooking the beautiful flower gardens. This backyard is truly something special—you'll feel like you've been transported to the English countryside. Peaceful, picturesque, and full of charm, it's the perfect place to slow down and enjoy the beauty around you.

Destiny Burns

Stellar Realty Group

231 Mitchell St, Henderson, TN 38340
/23
$235,000

Sold Feb 13, 2026

337 Morning View Cove, Henderson, TN 38340
- 3 Beds
- 2 Baths
- 1,393 Sq Ft
- Built 1999
Last Sold Summary
- 4% Below List Price
- $169/SF
- 36 Days On Market
Current Estimated Value $237,775

Last Listing Agent Jennifer Scott RE/MAX Realty Source

337 Morning View Cove, Henderson, TN 38340

/40
Est $163,800

Not Listed For Sale

10680 State Route 22a S, Enville, TN 38332
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1979
10680 State Route 22a S, Enville, TN 38332

Last Sold Summary
- 11 Days On Market
Last Listing Agent Katie Hughes Tiffany Jones Realty Group

/35
$480,000
- Land
- 143.34 Acres
- $3,349 per Acre
0 Highway 22 A, Enville, TN 38332

Don’t miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient access to Lexington, Henderson, and Adamsville while still providing the privacy, nature, and wide-open space buyers are looking for. With electricity available at the road and multiple ideal building sites, this property is

Lori Yarbro

Evans Real Estate

0 Highway 22 A, Enville, TN 38332
/31
$213,000

Sold Aug 14, 2026

5195 Tennessee 200, Henderson, TN 38340
- 3 Beds
- 2 Baths
- 1,306 Sq Ft
- Built 1963
Last Sold Summary
- 20% Below List Price
- $163/SF
- 41 Days On Market
Last Listing Agent Jennifer Stevens Coldwell Banker Southern Realty

5195 Tennessee 200, Henderson, TN 38340

/33
Est $261,189

Not Listed For Sale

360 Jacks Creek St, Henderson, TN 38340
- 3 Beds
- 2.5 Baths
- 2,050 Sq Ft
- Built 1989
360 Jacks Creek St, Henderson, TN 38340

Last Sold Summary
- 113 Days On Market
Last Listing Agent Linda Carter Casey Realtors

/42
$249,000

Pending
- 2 Beds
- 1 Bath
- 1,279 Sq Ft
470 North Ave, Henderson, TN 38340

This Charming Cottage is perfect for those seeking a Home with a heart. This beautiful Home features vintage details throughout, a cozy fireplace, original hardwood, stone counters, spacious backyard, plenty of natural light, hydrangeas, large front porch, and all the attention to details that will make you feel like you are living in a storybook! If you are looking for a beautiful Home that

Destiny Burns

Stellar Realty Group

470 North Ave, Henderson, TN 38340
/37
$245,000

Sold Sep 22, 2025

3605 Old Jacks Creek Rd, Henderson, TN 38340
- 3 Beds
- 2 Baths
- 1,485 Sq Ft
- Built 1979
Last Sold Summary
- 8% Below List Price
- $165/SF
- 95 Days On Market
Current Estimated Value $258,169

Last Listing Agent Sheila Darnell EXIT Realty Blues City

3605 Old Jacks Creek Rd, Henderson, TN 38340

/45
Est $459,898

Not Listed For Sale

215 Harris Ln, Henderson, TN 38340
- 4 Beds
- 2.5 Baths
- 2,614 Sq Ft
- Built 1990
215 Harris Ln, Henderson, TN 38340

Last Sold Summary
- 25 Days On Market
Last Listing Agent Tami Reid Hickman Realty Group Inc.-Jack

/23
$150,000

Pending
- 2 Beds
- 1 Bath
- 960 Sq Ft
304 Mifflin Ave, Henderson, TN 38340

Discover the perfect blend of convenience and affordability in this move-in-ready home just steps from Freed-Hardeman University and minutes from downtown Henderson. This inviting 2-bedroom, single-story home is ideal for anyone seeking an easy, low-maintenance lifestyle. Offering just under 1,000 square feet, the home features comfortable living areas and an eat-in kitchen with abundant cabinet

Brandi Isom

RE/MAX Realty Source

304 Mifflin Ave, Henderson, TN 38340
/3
$160,000

Sold Apr 23, 2026

00 Highway 45 S, Henderson, TN 38340
- Land
- 2.7 Acres
- $59,259 per Acre
Last Sold Summary
- 38% Below List Price
- 245 Days On Market
Last Listing Agent Craig Casey Casey Realtors

00 Highway 45 S, Henderson, TN 38340

/70
Est $526,368

Not Listed For Sale

5755 Old Jacks Creek Rd, Henderson, TN 38340
- 3 Beds
- 3.5 Baths
- 2,927 Sq Ft
- Built 2001
5755 Old Jacks Creek Rd, Henderson, TN 38340

Last Sold Summary
- 6 Days On Market
Last Listing Agent Destiny Burns Stellar Realty Group

/4
$42,000
- Land
- 1.65 Acres
- $25,455 per Acre
Lot 7 Greystone Cove, Henderson, TN 38340

Greystone Estates presents Lot 7! This beautiful 1.65-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

Destiny Burns

Stellar Realty Group

Lot 7 Greystone Cove, Henderson, TN 38340
/86
$1,800,000

Sold Aug 10, 2026

60 Proctor Rd, Henderson, TN 38340
- 4 Beds
- 5 Baths
- 4,570 Sq Ft
- Built 2024
Last Sold Summary
- 14% Below List Price
- $394/SF
- 26 Days On Market
Last Listing Agent Rachel Fullington Hickman Realty Group Inc.-Jack

60 Proctor Rd, Henderson, TN 38340

/31
Est $157,018

Not Listed For Sale

11555 State Route 22a S, Enville, TN 38332
- 3 Beds
- 2 Baths
- 1,604 Sq Ft
- Built 1959
11555 State Route 22a S, Enville, TN 38332

Last Sold Summary
- 123 Days On Market

Showing Results 1 - 40, Page 1 of 18

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Chester County, TN Homes

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