Jamestown, TN Homes

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  /11

  $50,000

  Sold Mar 20, 2026

  308 Pennycuff Ave, Jamestown, TN 38556

  • 2 Beds
  • 1 Bath
  • 648 Sq Ft
  • Built 1930

  Last Sold Summary

  • 29% Below List Price
  • $77/SF
  • 1 Day On Market

  Current Estimated Value $58,867

  Last Listing Agent Rhonda Darrow Home Touch Realty, LLC

  308 Pennycuff Ave, Jamestown, TN 38556
• 

  

  

  /13

  Est $153,000

  Not Listed For Sale

  550 Walking Horse Trail, Jamestown, TN 38556

  • Built 1985

  550 Walking Horse Trail, Jamestown, TN 38556

  Last Sold Summary

  • 9% Below List Price
  • $161/SF
  • 0 Days On Market

  • Last Sold Price $167,500
  • Jun 13, 2024

  Last Listing Agent Lisa Garrett Mitchell Real Estate & Auction Co.
• 

  

  /2

  $190,000

  • Land
  • 20.01 Acres
  • $9,495 per Acre

  4169 Gatewood Ford Rd, Jamestown, TN 38556

  ---More photos coming soon---Unrestricted 20-Acre Homestead - Private Plateau Retreat Escape to the heart of the Cumberland Plateau with this pristine 20.00-acre tract in Jamestown, TN. Located just north of Gate Wood Ford Road, this property offers the ultimate blank canvas for your Tennessee dream--whether that's a private family estate, a self-sufficient homestead, or a weekend getaway for

  

  Lisa Garrett

  Mitchell Real Estate & Auction Co.

  (931) 485-5087

  4169 Gatewood Ford Rd, Jamestown, TN 38556
• 

  

  

  /12

  $119,000

  Sold Dec 17, 2025

  n/a Allardt Hwy, Jamestown, TN 38556

  • Land
  • 7.48 Acres
  • $15,909 per Acre

  Last Sold Summary

  • 1% Below List Price
  • 0 Days On Market

  Last Listing Agent Rhonda Darrow Home Touch Realty LLC

  n/a Allardt Hwy, Jamestown, TN 38556
• 

  

  

  /24

  Est $393,721

  Not Listed For Sale

  1559 Hollis Poore Rd, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Built 2004

  1559 Hollis Poore Rd, Jamestown, TN 38556

  Last Sold Summary

  • 5% Above List Price
  • $321/SF
  • 111 Days On Market

  • Last Sold Price $375,000
  • May 01, 2025

  Last Listing Agent Rhonda Darrow Home Touch Realty
• 

  

  /18

  $249,900

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  803 Old Poplar Cove Rd, Jamestown, TN 38556

  2 HOMES FOR THE PRICE OF ONE !!!! Brand New Construction, a beautiful western style 1 bedroom 1 bath home and a 2 Bedroom 1 bath completely remodeled mobile home located just outside the city limits of Jamestown, beautiful custom cabinets, very spacious living area, large utility room, the mobile home is 2 bedroom 1 bath that is remodeled from top to bottom, perfect for in-laws or multiple

  

  Todd Stephens

  Crye-Leike Brown Executive Realty

  (931) 272-3480

  803 Old Poplar Cove Rd, Jamestown, TN 38556
• 

  

  /53

  $380,000

  Sold Sep 12, 2025

  345 Spruce Creek Dr, Jamestown, TN 38556

  • 2 Beds
  • 2 Baths
  • 1,369 Sq Ft
  • Built 1998

  Last Sold Summary

  • 14% Below List Price
  • $278/SF
  • 122 Days On Market

  Current Estimated Value $396,296

  Last Listing Agent Deborah Mountain Bestway Realty

  345 Spruce Creek Dr, Jamestown, TN 38556
• 

  

  /27

  Est $326,474

  Not Listed For Sale

  4875 S York Hwy, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1959

  4875 S York Hwy, Jamestown, TN 38556

  Last Sold Summary

  • 3% Below List Price
  • $190/SF
  • 189 Days On Market

  • Last Sold Price $335,000
  • Nov 24, 2023

  Last Listing Agent Annette Renaud Crye-Leike Brown Realty
• 

  

  /30

  $269,000

  $6K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  105 River Ln, Jamestown, TN 38556

  Fully renovated River Cabin with 2 bedrooms plus a flexible 3rd room (ideal as a bedroom, office, or guest space), perfect for a new owner or Airbnb. Just 700 yards from the East Obey River and Compton Bottoms boat landing, with quick access to East Port Marina and Dale Hollow Lake. The cabin offers 2 full baths, two living rooms with accent fireplaces, and two spacious porches. The upper porch

  

  Adam Pipkin

  Tennessee Life Real Estate Professionals

  (931) 419-5505

  105 River Ln, Jamestown, TN 38556
• 

  

  /27

  $279,000

  Sold Aug 15, 2025

  1754 Glenobey Rd, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1995

  Last Sold Summary

  • $221/SF
  • 12 Days On Market

  Current Estimated Value $300,063

  Last Listing Agent Todd Stephens Crye-Leike Brown Executive Realty

  1754 Glenobey Rd, Jamestown, TN 38556
• 

  

  /33

  Est $405,398

  Not Listed For Sale

  1080 Old Sunbright Rd, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 3,585 Sq Ft
  • Built 1981

  1080 Old Sunbright Rd, Jamestown, TN 38556

  Last Sold Summary

  • 14% Above List Price
  • $99/SF
  • 426 Days On Market

  • Last Sold Price $355,000
  • Jun 14, 2023

  Last Listing Agent Todd Stephens Crye-Leike Brown Executive Realty
• 

  

  /15

  $189,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  242 Joe Barnett Rd, Jamestown, TN 38556

  Remodeled like New! This 3 bedroom home has been remodeled, new flooring, plumbing, paint, cabinets, water heater, HVAC unit and more. The home has a nice fireplace in living room. Additional acreage available. Call today!

  

  Lisa Garrett

  MITCHELL REAL ESTATE, LLC

  (931) 536-9155

  242 Joe Barnett Rd, Jamestown, TN 38556
• 

  

  /8

  $250,000

  Sold Jan 28, 2026

  1185 Spruce Creek Dr, Jamestown, TN 38556

  • Land
  • 15 Acres
  • $16,667 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 201 Days On Market

  Last Listing Agent Steve Diskin Burks Diskin Real Estate

  1185 Spruce Creek Dr, Jamestown, TN 38556
• 

  

  /30

  Est $120,300

  Not Listed For Sale

  148 George Young Rd, Jamestown, TN 38556

  • 1 Bed
  • 1 Bath
  • 360 Sq Ft
  • Built 2020

  148 George Young Rd, Jamestown, TN 38556

  Last Sold Summary

  • 35% Above List Price
  • $247/SF
  • 60 Days On Market

  • Last Sold Price $89,000
  • Feb 16, 2024

  Last Listing Agent Rhonda Darrow Southern Star Realty
• 

  

  /15

  $79,500

  • Land
  • 1.34 Acres
  • $59,328 per Acre

  115 Legacy Way, Jamestown, TN 38556

  Semi-cleared lot located in a desirable equestrian subdivision featuring private riding trails throughout the community. Conveniently situated just minutes from East Fork Stables and a short drive to the renowned Big South Fork National River and Recreation Area with over 150 miles of scenic riding trails. A great opportunity to build your dream home, barn, or weekend getaway in the heart of

  

  Melissa Wolff

  Home Touch Realty, LLC

  (931) 240-5868

  115 Legacy Way, Jamestown, TN 38556
• 

  /2

  $599,900

  Sold Jul 17, 2025

  634 Cowboy Way, Jamestown, TN 38556

  • 3 Beds
  • 3 Baths
  • 1,792 Sq Ft
  • Built 2020

  Last Sold Summary

  • $335/SF
  • 0 Days On Market

  Current Estimated Value $608,953

  Last Listing Agent Other Other Non Realtor Other Non Member Office

  634 Cowboy Way, Jamestown, TN 38556
• 

  

  /16

  Est $110,750

  Not Listed For Sale

  4601 S York Hwy, Jamestown, TN 38556

  • 3 Beds
  • 1 Bath
  • 1,212 Sq Ft
  • Built 1960

  4601 S York Hwy, Jamestown, TN 38556

  Last Sold Summary

  • 48% Above List Price
  • $62/SF
  • 131 Days On Market

  • Last Sold Price $75,000
  • Sep 20, 2024

  Last Listing Agent Todd Stephens Crye-Leike Brown Executive Realty
• 

  

  /9

  $69,900

  • Land
  • 5.61 Acres
  • $12,460 per Acre

  0 Ridge Top Dr Unit 11655632, Jamestown, TN 38556

  MUST SEE !! Beautiful 5.61 acres of land to build on with park-like features-creek and cave located at the back of the property as well as riding trails from your property. This land is located in the equestrian community of Ridge Top and features several miles of exclusive horse-only trails with direct riding trails into Big South Fork National Park, providing access to 200+ miles of scenic

  

  Lisa Garrett

  MITCHELL REAL ESTATE, LLC

  (931) 377-2375

  0 Ridge Top Dr Unit 11655632, Jamestown, TN 38556
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  /39

  $8,000

  Sold Jun 09, 2025

  Lot 27 N Star Rd, Jamestown, TN 38556

  • Land
  • 1.06 Acres
  • $7,547 per Acre

  Last Sold Summary

  • 68% Below List Price
  • 179 Days On Market

  Last Listing Agent Debra Dodd No 1 Quality Realty

  Lot 27 N Star Rd, Jamestown, TN 38556
• 

  

  /3

  Not Listed For Sale

  349 Lakewood Dr, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 2,052 Sq Ft
  • Built 1997

  349 Lakewood Dr, Jamestown, TN 38556

  Last Sold Summary

  • $106/SF

  • Last Sold Price $217,000
  • May 30, 2023

  Last Listing Agent Chris Dalton Highlands Elite Real Estate LLC - Crvl
• 

  

  /14

  $29,900

  • Land
  • 1.03 Acres
  • $29,029 per Acre

  0 Georgee Road Lot 14, Jamestown, TN 38556

  Beautiful1.03 acres located in great location. The utilities are at the road and high speed internet available. Call today!

  

  Lisa Garrett

  Mitchell Real Estate & Auction

  (931) 888-3108

  0 Georgee Road Lot 14, Jamestown, TN 38556
• 

  

  /31

  $289,900

  Sold Dec 03, 2025

  121 Willow Lake Dr, Jamestown, TN 38556

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $181/SF
  • 166 Days On Market

  Current Estimated Value $294,719

  Last Listing Agent Todd Stephens Crye-Leike Brown Executive Realty

  121 Willow Lake Dr, Jamestown, TN 38556
• 

  

  /19

  Est $443,852

  Not Listed For Sale

  165 Hundred Oaks Loop, Jamestown, TN 38556

  • 4 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 1999

  165 Hundred Oaks Loop, Jamestown, TN 38556

  Last Sold Summary

  • 17% Above List Price
  • $178/SF
  • 28 Days On Market

  • Last Sold Price $380,000
  • Sep 26, 2024

  Last Listing Agent Steve Diskin Burks Diskin Real Estate
• 

  

  /8

  $75,000

  $50K PRICE DROP

  • Land
  • 1.39 Acres
  • $53,957 per Acre

  0 Cliffmont Unit 1326632, Jamestown, TN 38556

  Nice level to rolling building lot in the Highlands partial clear with driveway and cleared area in place for a home. Also available at additional cost is hay storage & pasture turn out. Private riding trails within development, or trail to the BSF for additional riding trails or East Forks stables. Build your home today and start riding til your heart is content. Very motivated seller..

  

  Melissa Wolff

  Home Touch Realty, LLC

  (931) 369-4412

  0 Cliffmont Unit 1326632, Jamestown, TN 38556
• 

  

  /59

  $205,000

  Sold Jul 25, 2025

  0 S York Hwy, Jamestown, TN 38556

  • Land
  • 11.84 Acres
  • $17,314 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 19 Days On Market

  Last Listing Agent Lisa Garrett Mitchell Real Estate & Auction LLC

  0 S York Hwy, Jamestown, TN 38556
• 

  

  /21

  Est $292,585

  Not Listed For Sale

  414 Sutton Rd, Jamestown, TN 38556

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 2004

  414 Sutton Rd, Jamestown, TN 38556

  Last Sold Summary

  • 6% Above List Price
  • $232/SF

  • Last Sold Price $275,000
  • Jun 30, 2023

  Last Listing Agent Tracy King Your Home Sold Guaranteed Real
• 

  

  /40

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,796 Sq Ft

  1065 Star Point Rd, Jamestown, TN 38556

  Beautiful 3 bedroom 2 bath ranch home on 5+ unrestricted ALL FENCED acres that in a great neighborhood just north of Jamestown, not far from Big South Fork National Park and East Fork Stables, home is excellent condition, new flooring custom cabinets, large bonus room with gas fireplace, property is fenced with nice horse barn with attached equipment shed and tack room with power and water,long

  

  Todd Stephens

  Crye-Leike Brown Executive Rea

  (931) 429-3963

  1065 Star Point Rd, Jamestown, TN 38556
• 

  

  /25

  $225,000

  Sold Aug 25, 2025

  2520 S York Hwy, Jamestown, TN 38556

  • 3 Beds
  • 1 Bath
  • 1,194 Sq Ft
  • Built 1981

  Last Sold Summary

  • 10% Below List Price
  • $188/SF
  • 82 Days On Market

  Current Estimated Value $238,206

  Last Listing Agent Rhonda Darrow Home Touch Realty

  2520 S York Hwy, Jamestown, TN 38556
• 

  

  /29

  Est $184,946

  Not Listed For Sale

  1070 Roanoke Rd, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 988 Sq Ft
  • Built 2007

  1070 Roanoke Rd, Jamestown, TN 38556

  Last Sold Summary

  • 9% Above List Price
  • $172/SF

  • Last Sold Price $170,000
  • Jul 07, 2023

  Last Listing Agent Elijah Castelli Elevate Real Estate
• 

  

  /35

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  103 N Duncan St, Jamestown, TN 38556

  Beautiful New Construction Home! This 3 bedroom, 2 bathroom home has a large open floor plan with split bedrooms for privacy, and nice cathedral ceilings. The kitchen has custom cabinets with quartz countertops and island, and The primary bedroom has a large walk-in closet and a walk-in shower. This home offers a large laundry room, and the big front and back porches are perfect for relaxing and

  

  Lisa Garrett

  Mitchell Real Estate & Auction Co.

  (931) 616-3501

  103 N Duncan St, Jamestown, TN 38556
• 

  

  /28

  $325,000

  Sold Jun 17, 2025

  357 Annabelle Way, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $210/SF
  • 78 Days On Market

  Last Listing Agent Lisa Garrett Mitchell Real Estate & Auction LLC

  357 Annabelle Way, Jamestown, TN 38556
• 

  

  /54

  Est $341,059

  Not Listed For Sale

  3410 Rugby Pike, Jamestown, TN 38556

  • 3 Beds
  • 1 Bath
  • 3,140 Sq Ft
  • Built 1972

  3410 Rugby Pike, Jamestown, TN 38556

  Last Sold Summary

  • 26% Above List Price
  • $86/SF
  • 3 Days On Market

  • Last Sold Price $270,000
  • Jul 17, 2023
• 

  

  /30

  $199,900

  $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,222 Sq Ft

  Unlisted Address

  Beautiful Brick Home!!! Completely remodeled 3 bedroom 2 bath brick home located in the city limits, new flooring and paint throughout the home, custom kitchen,spaciuos living room, large bonus room, central heat and air with backup natural gas heat,water well also on the property, just down the street from a main intersection, Also the building next door could also possibly be purchased, priced

  

  Todd Stephens

  Crye-Leike Brown Executive Realty

  (931) 575-5442

  Unlisted Address
• 

  

  /36

  $270,000

  Sold Oct 16, 2025

  584 Trimmer Ln, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 2023

  Last Sold Summary

  • 91% Below List Price
  • $235/SF
  • 0 Days On Market

  Current Estimated Value $282,455

  Last Listing Agent Lisa Garrett Mitchell Real Estate & Auction Co.

  584 Trimmer Ln, Jamestown, TN 38556
• 

  

  /48

  Est $366,898

  Not Listed For Sale

  185 James George Rd, Jamestown, TN 38556

  • 3 Beds
  • 3 Baths
  • 1,968 Sq Ft
  • Built 2006

  185 James George Rd, Jamestown, TN 38556

  Last Sold Summary

  • 19% Above List Price
  • $156/SF
  • 104 Days On Market

  • Last Sold Price $307,500
  • Nov 07, 2024

  Last Listing Agent Heather Skender-Newton Skender-Newton Realty
• 

  

  /72

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 3,812 Sq Ft

  265 Falling Leaf Rd, Jamestown, TN 38556

  Your Tennessee Lakefront Dream Home awaits!!! This magnificent Craftsman Hillside-Walkout Custom Home sits on Beautiful Lake Tara in the mountains of Tennessee. The home is designed by Architect Donald Gardner, with 3800+ sq-ft. This 4-bedroom, 4 full bath home lets you easily get lost in the details. The home has a gorgeous stone entrance which leads you into the main living area. Upon entry you

  

  Todd Stephens

  Crye-Leike Brown Executive Realty

  (931) 391-3347

  265 Falling Leaf Rd, Jamestown, TN 38556
• 

  

  /50

  $585,000

  Sold Oct 14, 2025

  218 Wildcat Rd, Jamestown, TN 38556

  • 2 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 2013

  Last Sold Summary

  • 8% Below List Price
  • $366/SF
  • 155 Days On Market

  Current Estimated Value $602,592

  Last Listing Agent Glenda Levin Mitchell Real Estate & Auction

  218 Wildcat Rd, Jamestown, TN 38556
• 

  

  /17

  Est $269,426

  Not Listed For Sale

  112 James George Rd, Jamestown, TN 38556

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Built 2004

  112 James George Rd, Jamestown, TN 38556

  Last Sold Summary

  • 20% Above List Price
  • $173/SF
  • 162 Days On Market

  • Last Sold Price $225,000
  • Oct 03, 2024

  Last Listing Agent Aira Ilao ListWithFreedom.com
• 

  

  /15

  $74,900

  • Land
  • 1.93 Acres
  • $38,808 per Acre

  1.93ac Glenobey Rd, Jamestown, TN 38556

  Awesome building lot or investment lot with BREATHTAKING VIEWS, located just minutes from town and just north of East Fork Stables and near Dale Hollow Lake, you can't beat this lot at this price!!! Buyer to verify all information and measurements in order to make an informed offer.

  

  Todd Stephens

  Crye-Leike Brown Executive Rea

  (931) 345-3261

  1.93ac Glenobey Rd, Jamestown, TN 38556
• 

  /2

  $10,000

  Sold Jul 09, 2025

  0 Chapman Rd Unit 1287974, Jamestown, TN 38556

  • Land
  • 6,098 Sq Ft
  • $71,429 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 126 Days On Market

  Last Listing Agent Rhonda Darrow Home Touch Realty, LLC

  0 Chapman Rd Unit 1287974, Jamestown, TN 38556

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