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Chester County, TN - homes for sale
143 of 143 results displayed
- New
$191,500Active2 beds 1 baths432 Galbraith Avenue, Henderson, TN 38340
MLS# 2603544Listed by: CASEY REALTORS - New
$255,000Active3 beds 2 baths3190 Plainview Road, Henderson, TN 38340
MLS# 2603542Listed by: COLDWELL BANKER SOUTHERN REALTY - New
$224,900Active3 beds 2 baths137 Fourth Street, Henderson, TN 38340
MLS# 2603526Listed by: CASEY REALTORS - New
$70,000Active3 beds 2 baths2,009 sq. ft.425B Second St, Henderson, TN 38340
MLS# 3302409Listed by: EXIT REALTY BLUES CITY - New
$64,500Active3 Acres1295 Weaver Thomas Road, Henderson, TN 38340
MLS# 2603447Listed by: CASEY REALTORS - New
$419,900Active3 beds 3 baths1615 Holly Springs Road, Henderson, TN 38340
MLS# 2603438Listed by: RAGAN REALTY GROUP - New
$255,000Active3 beds 2 baths200 Westwood Cove, Henderson, TN 38340
MLS# 2603427Listed by: CRYE-LEIKE ELITE - New
$224,000Active3 beds 2 baths1,471 sq. ft.460 Kendyl Cv, Henderson, TN 38340
MLS# 3298153Listed by: REZULTS REALTY, LLC 
$145,000Pending2 beds 1 baths3280 Pleasant Springs Road, Pinson, TN 38366
MLS# 2603371Listed by: COLDWELL BANKER SOUTHERN REALTY
$249,900Active3 beds 2 baths8800 100 HWY, Jacks Creek, TN 38347
MLS# 10226392Listed by: WEICHERT, REALTORS - CRUNK REA
$179,900Pending36.3 Acres00 Moss Loop, Enville, TN 38332
MLS# 2603361Listed by: PORCHLIGHT REALTY WEST TN
$51,900Pending3 beds 2 baths167 W Third Street, Henderson, TN 38340
MLS# 2603321Listed by: COLDWELL BANKER MCKEE REALTY
$415,000Pending3 beds 3 baths25 Max Lott Lane, Henderson, TN 38340
MLS# 2603294Listed by: STELLAR REALTY GROUP
$135,000Active3 beds 2 baths1,484 sq. ft.5885 State Route 225, Henderson, TN 38340
MLS# 3278521Listed by: SELL YOUR HOME SERVICES, LLC
$225,000Pending4 beds 2 baths2215 State Route 22a S, Jacks Creek, TN 38347
MLS# 2603242Listed by: RE/MAX REALTY SOURCE
$249,000Active2 beds 1 baths470 North Avenue, Henderson, TN 38340
MLS# 2603206Listed by: STELLAR REALTY GROUP
$674,999Active141 Acres00 State Route 22a S, Henderson, TN 38340
MLS# 2603198Listed by: BUY DIRT AUCTIONS & REALTY
$239,900Pending3 beds 2 baths347 E 4th Street, Henderson, TN 38340
MLS# 2603196Listed by: NEXTHOME 383 REAL ESTATE
$258,000Active3 beds 2 baths3045 Clifford Road, Luray, TN 38352
MLS# 2603191Listed by: BLUE SUEDE REALTY
$218,400Pending2 beds 2 baths30 Roby Road, Reagan, TN 38368
MLS# 2603184Listed by: RE/MAX REALTY SOURCE
$249,900Active4 beds 2 baths130 Simmons Street, Henderson, TN 38340
MLS# 2603178Listed by: CASEY REALTORS
$337,500Active3 beds 2 baths2,363 sq. ft.1160 Wilson School Road, Henderson, TN 38340
MLS# 2603155Listed by: RE/MAX REALTY SOURCE
$324,500Pending3 beds 2 baths2,237 sq. ft.1280 Wilson School Road, Henderson, TN 38340
MLS# 2603144Listed by: RE/MAX REALTY SOURCE
$699,000Active4 beds 4 baths3,314 sq. ft.215 Benson Rd, Reagan, TN 38368
MLS# 3260351Listed by: CLEAR CHOICE REALTY
$750,000Active7 Acres3695 Us Highway 45 N, Henderson, TN 38340
MLS# 2603127Listed by: CRYE-LEIKE ELITE
$183,350Pending48.25 Acres4600 Silerton Road, Henderson, TN 38340
MLS# 2603106Listed by: CASEY REALTORS
$241,900Active3 beds 2 baths1,678 sq. ft.618 Mifflin Avenue, Henderson, TN 38340
MLS# 2603098Listed by: CRYE-LEIKE ELITE
$576,500Active0 Acres00 E State Route 100 E (tract 3), Henderson, TN 38340
MLS# 2603073Listed by: BUY DIRT AUCTIONS & REALTY
$377,000Active0 Acres00 Highway 100 E (tract 2), Henderson, TN 38340
MLS# 2603074Listed by: BUY DIRT AUCTIONS & REALTY
$225,250Active0 Acres00 Highway 100 E (tract 1), Henderson, TN 38340
MLS# 2603076Listed by: BUY DIRT AUCTIONS & REALTY
$269,900Pending4 beds 2 baths170 LEAPWOOD DR, Enville, TN 38332-2024
MLS# 10224816Listed by: 2 RIVERS REALTY, LLC
$579,900Active3 beds 3 baths4,486 sq. ft.3290 Silerton Road, Henderson, TN 38340
MLS# 2602945Listed by: RE/MAX REALTY SOURCE
$234,900Active3 beds 3 baths610 Mifflin Avenue, Henderson, TN 38340
MLS# 2602931Listed by: CRYE-LEIKE ELITE
$169,900Active50.1 Acres0 Arl Bailey Road, Finger, TN 38334
MLS# 3247974Listed by: SELL YOUR HOME SERVICES, LLC
$141,500Active15.71 Acres0 Old Lula Road, Reagan, TN 38368
MLS# 2602912Listed by: RE/MAX REALTY SOURCE
$65,500Active7.28 Acres00 Old Lula Road, Reagan, TN 38368
MLS# 2602913Listed by: RE/MAX REALTY SOURCE
$245,000Active3 beds 2 baths1,850 sq. ft.320 Benson Rd, Reagan, TN 38368
MLS# 3246905Listed by: RE/MAX UNLIMITED
$213,000Active3 beds 2 baths30640 Highway 125 N, Henderson, TN 38340
MLS# 2602887Listed by: BHGRE CONNER JACKSON
$150,000Pending2 beds 1 baths304 Mifflin Avenue, Henderson, TN 38340
MLS# 2602874Listed by: RE/MAX REALTY SOURCE
$1,700,000Active112 Acres1120 Pleasant Ridge Road, Finger, TN 38334
MLS# 2602901Listed by: CRYE-LEIKE ELITE
$58,000Active2 AcresHILL AVE, Henderson, TN 38340
MLS# 10224186Listed by: MOLLY MOORE REALTY
$349,900Active5 beds 4 baths5,779 sq. ft.450 North Avenue, Henderson, TN 38340
MLS# 2602838Listed by: STELLAR REALTY GROUP
$250,000Pending3 beds 2 baths125 Benson Lane, Luray, TN 38352
MLS# 2602768Listed by: HALTOM REAL ESTATE GROUP
$37,500Active0 Acres00 Barham Avenue, Henderson, TN 38340
MLS# 2602717Listed by: CRYE-LEIKE ELITE
$139,900Pending3 beds 1 baths1,368 sq. ft.334 Baughn Street, Henderson, TN 38340
MLS# 2602704Listed by: CASEY REALTORS
$349,900Active2 beds 2 baths2,100 sq. ft.1380 Harrison Lane, Pinson, TN 38366
MLS# 2602689Listed by: SOUTHERN LIFESTYLE PROPERTIES
$535,000Active4 beds 2 baths100 Valleyview Drive, Henderson, TN 38340
MLS# 2602672Listed by: CASEY REALTORS
$219,900Active3 beds 2 baths248 E 3rd Street, Henderson, TN 38340
MLS# 2602636Listed by: CASEY REALTORS
$2,100,000Active4 beds 5 baths4,570 sq. ft.60 Proctor Rd, Henderson, TN 38340
MLS# 3230940Listed by: HICKMAN REALTY GROUP INC
$200,000Active65.9 Acres2800 Plainview Road, Henderson, TN 38340
MLS# 3230998Listed by: CRYE-LEIKE ELITE REALTORS
$199,900Active3 beds 1 baths1,272 sq. ft.454 White Ave, Henderson, TN 38340
MLS# 3230112Listed by: UNITED COUNTRY - COLUMBIA REALTY & AUCTION
$364,900Pending3 beds 2 baths359 Meadow Brook Drive, Henderson, TN 38340
MLS# 2602589Listed by: RE/MAX REALTY SOURCE
$348,000Active3 beds 2 baths521 Crook Avenue, Henderson, TN 38340
MLS# 2602585Listed by: CASEY REALTORS
$119,900Active29.86 Acres000 Cagle Trail, Henderson, TN 38340
MLS# 2602588Listed by: CASEY REALTORS
$424,000Active105 Acres935 BIG ROCK TRL, Henderson, TN 38340
MLS# 10223047Listed by: CRYE-LEIKE, INC., REALTORS
$279,900Pending3 beds 3 baths255 Mitchell Lane, Henderson, TN 38340
MLS# 2602566Listed by: CASEY REALTORS
$834,900Active6 beds 5 baths5,831 sq. ft.746 Oneal Lane, Henderson, TN 38340
MLS# 2602558Listed by: STELLAR REALTY GROUP
$179,950Active3 beds 1 baths478 Woods Drive, Henderson, TN 38340
MLS# 2602542Listed by: CASEY REALTORS
$385,923Active3 beds 2 baths1155 Ludell Ross Road, Enville, TN 38332
MLS# 2602496Listed by: RE/MAX REALTY SOURCE
$315,000Pending3 beds 2 baths746 Mason Avenue, Henderson, TN 38340
MLS# 2602430Listed by: COLDWELL BANKER SOUTHERN REALTY
$325,000Active45.72 Acres320 Peddy Vestal Loop, Henderson, TN 38340
MLS# 2602417Listed by: COLDWELL BANKER SOUTHERN REALTY
$225,000Pending3 beds 2 baths5195 Tn-200, Henderson, TN 38340
MLS# 2602418Listed by: COLDWELL BANKER SOUTHERN REALTY
$199,900Pending4 beds 2 baths1770 Sweet Lips Road, Henderson, TN 38340
MLS# 2602401Listed by: PHILLIPS REALTY GROUP
$239,900Pending4 beds 2 baths484 White Avenue, Henderson, TN 38340
MLS# 2602355Listed by: CRYE-LEIKE ELITE
$399,000Active3 beds 3 baths2,036 sq. ft.1555 Short Road, Pinson, TN 38366
MLS# 2602353Listed by: TOTAL REALTY SOURCE- Open Sun, 1 to 3pm
$195,000Active3 beds 2 baths318 Mifflin Avenue, Henderson, TN 38340
MLS# 2602322Listed by: RE/MAX REALTY SOURCE 
$450,000Active3 beds 2 baths1555 Us Highway 45 S Highway, Henderson, TN 38340
MLS# 2602307Listed by: CASEY REALTORS
$200,000Active65.9 Acres0 Plainview Road, Henderson, TN 38340
MLS# 2602224Listed by: CRYE-LEIKE ELITE
$420,000Active5 beds 2 baths3,051 sq. ft.100 Mary Kate Ln, Henderson, TN 38340
MLS# 3208441Listed by: CRYE-LEIKE ELITE REALTORS
$599,900Active151 Acres00 Garland Road, Henderson, TN 38340
MLS# 2602172Listed by: HICKMAN REALTY GROUP INC.-JACK
$455,000Active119 Acres000 Stewart Cementery Lane, Enville, TN 38332
MLS# 2602142Listed by: CASEY REALTORS
$210,000Pending3 beds 2 baths2,046 sq. ft.7435 State Route 100 E, Jacks Creek, TN 38347
MLS# 2602065Listed by: RE/MAX REALTY SOURCE
$480,000Active143.34 Acres0 Hwy 22a S, Enville, TN 38332
MLS# 3183906Listed by: EVANS REAL ESTATE
$95,000Active10.3 Acres0 Enville Road, Henderson, TN 38340
MLS# 3183286Listed by: THE HOMESTEAD GROUP
$220,000Active13.7 Acres250 Cedar Trails Lane, Jacks Creek, TN 38347
MLS# 2601898Listed by: RE/MAX REALTY SOURCE
$85,000Active22 Acres225 State Route, Henderson, TN 38340
MLS# 2601879Listed by: COLDWELL BANKER SOUTHERN REALTY
$319,900Pending3 beds 2 baths766 Mason Avenue, Henderson, TN 38340
MLS# 2601857Listed by: CRYE-LEIKE ELITE
$319,000Active23 Acres00 Williams Road, Henderson, TN 38340
MLS# 2601816Listed by: PORCHLIGHT REALTY WEST TN
$244,900Pending3 beds 2 baths3180 State Route 200, Henderson, TN 38340
MLS# 2601708Listed by: CASEY REALTORS
$245,000Active3 beds 2 baths2,452 sq. ft.320 Benson Road, Reagan, TN 38368
MLS# 2601667Listed by: RE/MAX UNLIMITED
$525,000Active4 beds 2 baths940 OLD LULA RD, Reagan, TN 38368
MLS# 10218645Listed by: UC RIVER CITY REALTY
$49,900Active5.5 Acres00 Moss Loop, Enville, TN 38332
MLS# 2601430Listed by: CRYE-LEIKE ELITE
$285,000Active4 beds 3 baths2985 Sand Mt Road, Enville, TN 38332
MLS# 2601411Listed by: RE/MAX REALTY SOURCE
$744,000Active5 beds 4 baths25 Oak Ridge Drive, Henderson, TN 38340
MLS# 2601343Listed by: CRYE-LEIKE ELITE
$275,000Active156 Acres0 N Old Cave Springs Road, Henderson, TN 38340
MLS# 2601327Listed by: PORCHLIGHT REALTY WEST TN
$188,000Pending3 beds 2 baths473 Galbraith Avenue, Henderson, TN 38340
MLS# 2601262Listed by: PORCHLIGHT REALTY WEST TN
$896,000Active5 beds 5 baths7,126 sq. ft.575 Homestead Lane, Henderson, TN 38340
MLS# 2601184Listed by: STELLAR REALTY GROUP
$60,000Active10.81 AcresTRACT 3 HWY 22A HWY, Jacks Creek, TN 38347
MLS# 10217053Listed by: 2 CRANES REALTY
$60,000Active13.42 AcresTRACT 9 HWY 22A HWY, Jacks Creek, TN 38347
MLS# 10217059Listed by: 2 CRANES REALTY
$199,999Pending3 beds 2 baths5085 HARDIN GRAVEYARD RD, Enville, TN 38332
MLS# 10216963Listed by: UC RIVER CITY REALTY
$159,900Pending2 beds 1 baths337 Hill Avenue, Henderson, TN 38340
MLS# 2601101Listed by: COLDWELL BANKER SOUTHERN REALTY
$159,900Pending3 beds 2 baths730 Old Montezuma Road, Henderson, TN 38340
MLS# 2601063Listed by: STELLAR REALTY GROUP
$94,900Active12 Acres5030 Sand Mountain Rd, Enville, TN 38332
MLS# 3147736Listed by: REAL BROKER
$869,900Active4 beds 3 baths495 Knuckles Road, Henderson, TN 38340
MLS# 2600907Listed by: CASEY REALTORS
$79,900Active26.8 Acres0 Sweetlips Road, Henderson, TN 38340
MLS# 3137906Listed by: SELL YOUR HOME SERVICES, LLC
$249,900Active3 beds 2 baths1,512 sq. ft.341 Melodie Cir, Henderson, TN 38340
MLS# 3136958Listed by: PHILLIPS REALTY GROUP LLC
$64,900Active8.9 Acres8705 State Route 100 E, Jacks Creek, TN 38347
MLS# 2600795Listed by: NEXTHOME 383 REAL ESTATE
$335,000Pending3 beds 3 baths2,156 sq. ft.185 Leath Ln, Finger, TN 38334
MLS# 3135722Listed by: BST REALTY
$299,000Active4 beds 3 baths2925 State Route 100 W, Henderson, TN 38340
MLS# 2600758Listed by: RE/MAX REALTY SOURCE
$19,900Active1 Acres285 Cedar Brook Lane, Henderson, TN 38340
MLS# 2600722Listed by: RE/MAX REALTY SOURCE
$44,900Active4 Acres0 Tn-125, Henderson, TN 38340
MLS# 2600701Listed by: STELLAR REALTY GROUP
$226,250Active4 beds 2 baths241 Crook Avenue, Henderson, TN 38340
MLS# 2600473Listed by: COMPASS RE
$125,000Active3 beds 2 baths11704 LEAPWOOD ENVILLE RD, Enville, TN 38332
MLS# 10213530Listed by: WEICHERT, REALTORS - CRUNK REA
$210,000Pending4 beds 2 baths2,834 sq. ft.6525 State Route 225, Henderson, TN 38340
MLS# 2600284Listed by: STELLAR REALTY GROUP
$235,000Active3 beds 2 baths155 Whitley Avenue, Henderson, TN 38340
MLS# 2600239Listed by: WENDELL ALEXANDER REALTY
$1,300,000Active5 beds 4 baths280 Harris Lane, Henderson, TN 38340
MLS# 2600135Listed by: CASEY REALTORS
$389,900Active3 beds 2 baths2130 Hughes Road, Henderson, TN 38340
MLS# 2600066Listed by: HICKMAN REALTY GROUP INC.-JACK
$375,000Active60 Acres795 Hill Avenue, Henderson, TN 38340
MLS# 2600005Listed by: CRYE-LEIKE ELITE
$239,900Pending3 beds 2 baths707 Mifflin Avenue Extension, Henderson, TN 38340
MLS# 2505818Listed by: CRYE-LEIKE ELITE
$112,000Active3 beds 2 baths225 Capps Lane, Pinson, TN 38366
MLS# 2505798Listed by: CASEY REALTORS
$225,550Active45.11 Acres0 State Route 22a S, Enville, TN 38332
MLS# 3047408Listed by: EVANS REAL ESTATE
$42,995Active7.84 AcresHUGHES RD, Henderson, TN 38340
MLS# 10208864Listed by: FARM & HOME REALTY
$565,000Active217.58 Acres0 Garland Road, Henderson, TN 38340
MLS# 2505164Listed by: PORCHLIGHT REALTY WEST TN
$550,000Active4 beds 4 baths614 Oneal Lane, Henderson, TN 38340
MLS# 2504894Listed by: CASEY REALTORS
$349,999Active112.22 Acres7258 Hardin Graveyard Road, Enville, TN 38332
MLS# 2600152Listed by: LILLY REALTY
$269,000Active0 AcresX Cedarbrook Lane, Henderson, TN 38340
MLS# 2504574Listed by: EXIT REALTY BLUES CITY
$149,900Active0 Acres1170 Keene Road, Enville, TN 38332
MLS# 2504416Listed by: LILLY REALTY
$244,700Active3 beds 2 baths135 W THIRD ST, Henderson, TN 38340-1805
MLS# 10216352Listed by: MOLLY MOORE REALTY
$825,000Active-- beds -- baths5,952 sq. ft.115 Chalet Ln, Henderson, TN 38340
MLS# 2990470Listed by: EVANS REAL ESTATE
$42,000Active2.12 AcresLot 8 Greystone Cove, Henderson, TN 38340
MLS# 2504116Listed by: STELLAR REALTY GROUP
$42,000Active2.27 AcresLot 18 Greystone Cove, Henderson, TN 38340
MLS# 2504118Listed by: STELLAR REALTY GROUP
$42,000Active3.77 AcresLot 21 Greystone Cove, Henderson, TN 38340
MLS# 2504119Listed by: STELLAR REALTY GROUP
$42,000Active2.94 AcresLot 22 Greystone Cove, Henderson, TN 38340
MLS# 2504121Listed by: STELLAR REALTY GROUP
$42,000Active1.61 AcresLot 5 Greystone Cove, Henderson, TN 38340
MLS# 2504112Listed by: STELLAR REALTY GROUP
$42,000Active1.65 AcresLot 7 Greystone Cove, Henderson, TN 38340
MLS# 2504114Listed by: STELLAR REALTY GROUP
$35,750Active7.44 Acres000 Stewart Road, Henderson, TN 38340
MLS# 2504031Listed by: CASEY REALTORS
$549,000Active4 beds 5 baths5,710 sq. ft.50 Braund Road, Henderson, TN 38340
MLS# 2503967Listed by: STELLAR REALTY GROUP
$750,000Active5 beds 5 baths715 Roundtree Lane, Beech Bluff, TN 38313
MLS# 2503887Listed by: COLDWELL BANKER SOUTHERN REALTY
$48,000Active5.2 Acres00 Lofton Road, Enville, TN 38332
MLS# 2503847Listed by: CASEY REALTORS
$50,000Active6.35 Acres0 Old Sobby Road, Bethel Springs, TN 38315
MLS# 2503522Listed by: RE/MAX REALTY SOURCE
$157,400Active3 beds 2 baths1295 Mayfield Road, Henderson, TN 38340
MLS# 2502190Listed by: CASEY REALTORS
$31,500Active5 AcresMULLINS RD, Luray, TN 38352
MLS# 10189824Listed by: FARM & HOME REALTY
$21,900Pending1.3 AcresLot 21 Timberwood Cove, Henderson, TN 38340
MLS# 245733Listed by: CASEY REALTORS
$450,000Active157.68 AcresHWY 125 HWY, Henderson, TN 38340
MLS# 10179487Listed by: MORRIS AND MORRIS
$55,000Active2 beds 1 baths2160 Jones Road, Luray, TN 38352
MLS# 245782Listed by: CASEY REALTORS
$39,900Active5 Acres5 MULLINS RD, Luray, TN 38352
MLS# 10175487Listed by: FARM & HOME REALTY- $34,900Active5 Acres
2 MULLINS RD, Luray, TN 38352
MLS# 10175489Listed by: FARM & HOME REALTY - $29,900Active4.62 Acres
1 MULLINS RD, Luray, TN 38352
MLS# 10175490Listed by: FARM & HOME REALTY - $22,500Active2.79 Acres
6 MIDDLEFORK RD, Luray, TN 38352
MLS# 10175492Listed by: FARM & HOME REALTY 
$20,000Active1 Acres00 Deerfield Loop, Henderson, TN 38340
MLS# 242331Listed by: CASEY REALTORS
$85,000Active15 Acres3095 Lofton Ln, Enville, TN 38332
MLS# 2604014Listed by: 731 REALTY, LLC
$301,600Active30.16 Acres00 Woodland Drive, Henderson, TN 38340
MLS# 221896Listed by: CASEY REALTORS
$750,000Active1.38 Acres00 Newsome Ave, Henderson, TN 38340
MLS# 224789Listed by: CRYE-LEIKE ELITE
Local realty services provided by:CENTURY 21 Golden Service Realty & Auction, Inc., CENTURY 21 Premier, CENTURY 21 Home First Realtors
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.