Homes for Sale in 38556

• 

  

  

  /8

  $245,000

  • 3 Beds
  • 1.5 Baths
  • 700 Sq Ft

  2800 Leatherwood Ford Rd, Jamestown, TN 38556

  Prime Location Near Big South Fork!Discover over 7 unrestricted acres just minutes from the Big South Fork National River & Recreation Area. with highway frontage and approximately 3+ acres of cleared pasture, this property combines convenience with scenic rural charm.The land features two existing structures: a single-wide mobile home and a large metal garage/barn. Fenced pastures make

  Cindy Stedman Allardt Real Estate Association LLC

  2800 Leatherwood Ford Rd, Jamestown, TN 38556
• 

  

  

  /33

  $536,900

  • 4 Beds
  • 3 Baths
  • 2,028 Sq Ft

  68 Buffalo Cove Ln, Jamestown, TN 38556

  Welcome home to this nearly new 4-bedroom, 3-bath basement rancher set on 5 beautiful acres, offering privacy, space, and modern comfort. Built just 5 years ago, this home features a spacious open-concept layout centered around a large island kitchen with custom cabinetry, perfect for everyday living and entertaining. The main-level primary suite includes dual his-and-hers closets and a luxurious

  Rick Gross CENTURY 21 Legacy

  68 Buffalo Cove Ln, Jamestown, TN 38556
• 

  

  

  /39

  $225,000

  • 2 Beds
  • 1 Bath
  • 1,688 Sq Ft

  106 Windcrest Dr, Jamestown, TN 38556

  1.08 acres, 2 Bedrooms Live the good life! Welcome to 106 Westwind in Jamestown, TN--where peaceful living meets outdoor adventure. Nestled in a quiet setting, this property is perfect for nature lovers and those seeking a slower pace surrounded by the beauty of the Upper Cumberland.Located just minutes from the Big South Fork National River & Recreation Area and Pickett State Park, you'll

  Margo Carroll Weichert, Realtors-The Webb Agency

  106 Windcrest Dr, Jamestown, TN 38556
• 

  

  

  /25

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  318 Sadie St, Jamestown, TN 38556

  Priced to sell! Welcome to this Remodeled 3 bedroom, 2 bath home and a garage is ideally situated in the heart of town, offering both convenience and comfort. As you step inside, you'll be greeted by an open concept living space, featuring modern finishes and abundance of natural light. The home has been remodeled. The HVAC is only a couple of months old. The spacious living room flows into a

  Christopher Todd Stephens Mitchell Real Estate & Auction

  318 Sadie St, Jamestown, TN 38556
• 

  

  /2

  $229,900

  • 3 Beds
  • 1.5 Baths
  • 1,541 Sq Ft

  1340 Old Allardt Rd, Jamestown, TN 38556

  Nice spacious brick home with 3bdr 1 1/2 bathroom, family room with wood burning insert. Home is located on .53 acre just minutes to Jamestown. Bathroom currently under construction adding a stand up shower. Large building for storage, shed in back does not sell with property.

  Deborah Mountain Bestway Realty

  1340 Old Allardt Rd, Jamestown, TN 38556
• 

  

  /21

  $110,000

  • Land
  • 1.14 Acres
  • $96,491 per Acre

  0 Eagle Unit 1323153, Jamestown, TN 38556

  Wonderful bluff lot in the gated equestrian community of The Highlands. Bluff lot, wooded, great building site. Enjoy the use of 2 stalls and paddocks that come with the purchase in the owners barns. Also, paddocks for rent for $150.00 a month. 3000 acres included with 45 miles of private equestrian trails included for your use. Come ride and leave the barn and ground maintenance up to the staff.

  Glenda Levin Mitchell Real Estate & Auction

  0 Eagle Unit 1323153, Jamestown, TN 38556
• 

  

  /27

  $429,900

  • 2 Beds
  • 3 Baths
  • 1,680 Sq Ft

  1225 Louvaine Rd, Jamestown, TN 38556

  Located in Ridgetop Acres adjacent to the Big South Fork is this 2 bedroom/3 bath home on 2.76 acs. Home has a cabin like feel with all wood and laminate floors and walls. 2 bonus rooms could easily be converted to use as bedrooms. Exterior is vinyl with a metal roof. Spacious 2 car garage with circular driveway and RV pad. Literally ride from your home into the Big South Fork Park.

  Troy Gammon Southern Star Realty

  1225 Louvaine Rd, Jamestown, TN 38556
• 

  

  /6

  $150,000

  • Land
  • 1.88 Acres
  • $79,787 per Acre

  478 Spruce Creek Dr, Jamestown, TN 38556

  Located in Spruce Creek Acres, this ready‑to‑build lot gives you the freedom to camp, ride, and begin shaping for the home or getaway you've always imagined.The property is already set up with an RV hookup, a 2‑bedroom septic system, water, electric, and Wi‑Fi. It's fully fenced—mostly with attractive wood fencing—and includes a 2‑stall barn with tack and hay

  Cindy Stedman Allardt Real Estate Association LLC

  478 Spruce Creek Dr, Jamestown, TN 38556
• 

  

  /28

  $49,900

  • Land
  • 6.56 Acres
  • $7,607 per Acre

  LOT 46 Cheyenne Dr, Jamestown, TN 38556

  6.56 surveyed ac in a high prestige gated community (Rockcastle) located in the hills of TN with mtn views and privacy and security. Modest restrictions on file – in docs. Stream, level lot to a gentle roll terrain, several building sites with much potential, over 375 ft of paved road frontage, electric – telephone – high speed internet available – fiber optics to connect into, well developed

  Debra Dodd No. 1 Quality Realty-celina

  LOT 46 Cheyenne Dr, Jamestown, TN 38556
• 

  

  /15

  $619,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  1230 Darrow Ridge Rd, Jamestown, TN 38556

  BRAND NEW BUILD completed end of APRIL 2026. 1732 square foot 3 bed 2 bath home sitting on 5 pristine ACRES of cleared land for pasture DOTTED with mature trees for character. Perfect Equestrian property situated in the Equestrian community of RIDGE TOP ACRES. 8 to 10 miles of community horse trail system with one trail that takes you directly into the BIG SOUTH FORK NATIONAL PARK showcasing 220

  Steve Diskin Burks Diskin Real Estate

  1230 Darrow Ridge Rd, Jamestown, TN 38556
• 

  

  /3

  $285,000

  • Land
  • 17.06 Acres
  • $16,706 per Acre

  3490 Leatherwood Ford Rd, Jamestown, TN 38556

  Here's a once-in-a-lifetime opportunity to own 17 stunning acres bordering the Big South Fork NRRA! Enjoy direct access to the Cumberland Valley Trailhead and an SCTA horse trail that connects to the neighborhood trail system. With approximately 5 acres of cleared pasture and a beautiful 4-rail wood fence along the road, this property is the ideal setting to build your dream home or farm. Water

  Cindy Stedman Allardt Real Estate Association LLC

  3490 Leatherwood Ford Rd, Jamestown, TN 38556
• 

  

  /7

  $18,995

  • Land
  • 1.01 Acres
  • $18,807 per Acre

  299 Fair Oaks Ln, Jamestown, TN 38556

  A all wooded 1.01 +/- acre that is a good home site there is suppose to be a septic already installed but no records could be found has water and electric available at rd.The only restrictions found was a 20 ft. easement for utilities

  Bart Neely Bestway Realty

  299 Fair Oaks Ln, Jamestown, TN 38556
• 

  

  /28

  $168,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  957 Allardt Hwy, Jamestown, TN 38556

  This 1,008 sq ft home is wonderfully updated and ready for its next owner or investor. Featuring 2 bedrooms, 1 bath, and a flexible bonus room ideal for an office or extra guest space, this property is a high potential rental or residence. Enjoy total peace of mind with a new roof (Nov 2025) and new HVAC and stove (Sept 2025). The level, private lot features a U-shaped driveway for easy parking

  Andy Peterson eXp Realty, LLC

  957 Allardt Hwy, Jamestown, TN 38556
• 

  

  /6

  $150,000

  • Land
  • 11 Acres
  • $13,636 per Acre

  0 Fairgrounds Rd Unit 1255783, Jamestown, TN 38556

  A great 11 surveyed acres sitting just outside Jamestown city limits property does back up to Alvin C York High School property is level with several building sites and has a creek that runs through the property a must see

  Bart Neely Bestway Realty

  0 Fairgrounds Rd Unit 1255783, Jamestown, TN 38556
• 

  

  /3

  $99,000

  • Land
  • 7.62 Acres
  • $12,992 per Acre

  0 Flat Rock Unit Lot 6, Jamestown, TN 38556

  Escape to your own slice of countryside paradise with this stunning 7.62-acre tract located in sought-after horse country. Featuring breathtaking views, this property is already equipped with well water and electric, saving you time and expense. Choose from several beautiful building sites to create your ideal home. Wander the existing trails that guide you to a peaceful creek along the back of

  Lesley McNeal RE/MAX Finest

  0 Flat Rock Unit Lot 6, Jamestown, TN 38556
• 

  

  /11

  $129,000

  • Land
  • 35,283 Sq Ft
  • $159,259 per Acre

  Lot 4 Cliffmont, Jamestown, TN 38556

  Lot 4 on .81 acres located in the Exquisite Highlands at Big South Fork. Subdivision has Gated Entrance, Paved Roads, Underground Utilities, Miles of Adjacent Horse Trails with Breath Taking Bluff views. Community Barn with Stalls and Paddocks with Run-In are available at additional cost. Several Lots to choose from. Come Visit for a Tour. $129,000.

  Erica Styles Allardt Real Estate Association LLC

  Lot 4 Cliffmont, Jamestown, TN 38556
• 

  

  /54

  $770,000

  • 2 Beds
  • 2 Baths
  • 2,400 Sq Ft

  232 Wild Cat Rd, Jamestown, TN 38556

  Tucked at the end of a peaceful cul-de-sac in the Spruce Creek Equestrian Community with direct access to neighborhood trails and trails into the Big South Fork right from your property, this beautiful 2BR 2BA cabin features 2400sf of living space & a 3 car attached Heated & Cooled garage, sitting on 5.77 acres fully fenced. Home boasts covered front and back porch, master suite on the main level

  Erica Styles Allardt Real Estate Association LLC

  232 Wild Cat Rd, Jamestown, TN 38556
• 

  

  /31

  $254,929

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft

  1300 Perimeter Dr, Jamestown, TN 38556

  Motivated seller. This property is on a corner lot in a park-like setting within the Whispering Winds Lake Community which offers access for fishing, kayaking, canoeing, and boating. This ranch home with a walk-out bsmt has had all of your major concerns updated! HVAC, roof, garage door, appliances, leaf guards, sidewalk, and front/back doors are just a few examples. Walking up, you have

  Heather Skender-Newton Skender-Newton Realty

  1300 Perimeter Dr, Jamestown, TN 38556
• 

  

  /12

  $119,000

  • Land
  • 1.67 Acres
  • $71,257 per Acre

  0 Lots 8 & 9 Eagle Bluff Unit 1218031, Jamestown, TN 38556

  Lot 8 & 9 on 1.67 acres located in the Exquisite Highlands at Big South Fork. Subdivision has Gated Entrance, Paved Roads, Underground Utilities, Miles of Adjacent Horse Trails with Breath Taking Bluff views. Community Barn with Stalls and Paddocks with Run-In are available at additional cost. Several Lots to choose from. Come Visit for a Tour.

  Cindy Stedman Allardt Real Estate Association LLC

  0 Lots 8 & 9 Eagle Bluff Unit 1218031, Jamestown, TN 38556
• 

  

  /15

  $74,900

  • Land
  • 10 Acres
  • $7,490 per Acre

  0 Apache Rd Unit 20, Jamestown, TN 38556

  10.00 surveyed ac in a high prestige gated community (Rockcastle) located in the hills of TN with mtn views with privacy and security. Modest restrictions on file – in docs. Level lot with a gentle roll terrain, several building sites to select from, over 350+ ft of gravel road frontage, electric – telephone – high speed internet available to connect into, Approx 1000 to 1200 elevation, MTN

  Debra Dodd No 1 Quality Realty

  0 Apache Rd Unit 20, Jamestown, TN 38556
• 

  

  /10

  $50,000

  • Land
  • 13.13 Acres
  • $3,808 per Acre

  0 Pawnee Ln Unit 1304574, Jamestown, TN 38556

  13.13 Wooded Acres at Cul-de-Sac in Rockcastle Beautiful 13.13-acre wooded tract located in the desirable Rockcastle subdivision, offering the perfect setting to build your dream home in a peaceful country environment. Recently surveyed and situated at the end of a cul-de-sac, this property provides added privacy, natural beauty, and plenty of space for your custom home, cabin, or private

  Donna Baisley Baisley Hometown Realty, LLC

  0 Pawnee Ln Unit 1304574, Jamestown, TN 38556
• 

  

  /11

  $165,000

  • Land
  • 3.27 Acres
  • $50,459 per Acre

  170 Saddle Dr, Jamestown, TN 38556

  Build your dream home or vacation retreat on this stunning 3.27±-acre property in the highly desirable. RV pad with water, electric and septic already installed. Spruce Creek Acres community. Enjoy direct access to private neighborhood riding trails that flow seamlessly into the Big South Fork National River & Recreation Area, offering unparalleled horseback riding and scenic hiking. Minutes

  Cindy Stedman Allardt Real Estate Association LLC

  170 Saddle Dr, Jamestown, TN 38556
• 

  

  /28

  $145,000

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  1100 N York Hwy, Jamestown, TN 38556

  Close to town 3 bd rm 2 bth home with nice yard and lots of storage room.

  Patrick Flowers Bestway Realty

  1100 N York Hwy, Jamestown, TN 38556
• 

  

  /33

  $235,900

  • Land
  • 16.28 Acres
  • $14,490 per Acre

  1090 Old Sunbright Rd, Jamestown, TN 38556

  Dreaming of the perfect place to build your Tennessee home? You've found it! This beautiful UNRESTRICTED property offers the ideal mix of cleared, flat, and wooded land—perfect for your dream home, barndominium, or mobile/modular home. Enjoy stunning views, space for farm animals or horses, and multiple build sites. Features include a circle driveway, electric, water, septic, and full RV

  Delvon Stults The Heartland Real Estate Co., Llc

  1090 Old Sunbright Rd, Jamestown, TN 38556
• 

  

  /15

  $109,900

  • Land
  • 51.63 Acres
  • $2,129 per Acre

  0 Choctaw Unit 1334766, Jamestown, TN 38556

  Looking to live off the grid and embrace privacy and seclusion? This expansive wooded tract offers the perfect opportunity to create your own private retreat. With light restrictions and multiple potential building sites, the property is ideal for a family compound or a peaceful homestead. Enjoy abundant wildlife and the option to live simply and sustainably, surrounded by nature. Whether you're

  Rhonda Darrow Home Touch Realty, LLC

  0 Choctaw Unit 1334766, Jamestown, TN 38556
• 

  

  /4

  $39,900

  • Land
  • 3.57 Acres
  • $11,176 per Acre

  0 Panther Branch Rd Unit 1312723, Jamestown, TN 38556

  Look for unrestricted acreage to build your dream home? Corner acreage of 3.57 wooded acres. Minutes to all amenities, but far enough from the city lights & traffic.

  Rhonda Darrow Home Touch Realty, LLC

  0 Panther Branch Rd Unit 1312723, Jamestown, TN 38556
• 

  

  /26

  $625,000

  • Land
  • 152 Acres
  • $4,112 per Acre

  150 AC Prong of Clear, Jamestown, TN 38556

  Opportunity of a lifetime! This sprawling 150-acre UNRESTRICTED property in Jamestown offers endless potential and is a rare find. With an easement already in place for access, this incredible land is loaded with value, featuring tons of marketable timber and rock. Adding to its allure, the beautiful North Prong Clear Fork Creek winds through the property, creating serene waterfront views and an

  Elijah Castelli Elevate Real Estate

  150 AC Prong of Clear, Jamestown, TN 38556
• 

  

  /23

  $310,000

  • 3 Beds
  • 1.5 Baths
  • 1,104 Sq Ft

  875 S Fork Dr, Jamestown, TN 38556

  Sweet home in a horse community, on trail, with a detached garage/ workshop space and 3 stall barn on 1.5 acres. NO HOA here. Half bath in the large master bedroom. Kitchen has a pantry and lovely wood cabinets. Nice front and back covered porches. Fenced front yard. Guest bathroom remodeled last year in 2025. New ramp on back porch. Buyer is responsible for all measurements. Enclosed electrified

  Kathy Brown Wallace

  875 S Fork Dr, Jamestown, TN 38556
• 

  

  /33

  $94,000

  • Land
  • 7.08 Acres
  • $13,277 per Acre

  0 Tomahawk Unit 73, Jamestown, TN 38556

  7.08 surveyed ac located approx 1000 to 1300 elevation giving this lot a lovely stare of mtn views & the valley for miles. Easy access off a private road onto an Improved driveway, modest restrictions, Electric – telephone – Internet & Fiber Optics is available from the road, loads of wildlife, loads of privacy, mature timber in the wooded area & loads of fresh air. Building site has been

  Debra Dodd No 1 Quality Realty

  0 Tomahawk Unit 73, Jamestown, TN 38556
• 

  

  /35

  $219,900

  • 2 Beds
  • 1 Bath
  • 1,212 Sq Ft

  925 Unity Church Rd, Jamestown, TN 38556

  Adorable and full of potential, this charming 2-bedroom, 1-bath home offers comfort, versatility, and room to grow. A spacious bonus room provides endless possibilities--perfect for a third bedroom, home office, or family room to suit your needs. Inside, you'll love the gleaming -inch hardwood flooring and custom wood kitchen cabinets, complete with an island and all appliances conveying. The

  Rhonda Darrow Home Touch Realty LLC

  925 Unity Church Rd, Jamestown, TN 38556
• 

  

  /18

  $39,990

  • Land
  • 6.56 Acres
  • $6,096 per Acre

  0 Cheynne Dr Unit 1325451, Jamestown, TN 38556

  6.56 acers located in the impressive, Rockcastle gated community. Gorgeous mountain views to enjoy along with privacy and security. Modest restrictions on file - in docs. Several building sites with tons of potential, Electric - telephone - high speed internet available - fiber optics to connect into, well developed area, gated with security gate entrance, loads of wildlife and nature. Approx 5

  Beth Rains North Cumberland Realty, LLC

  0 Cheynne Dr Unit 1325451, Jamestown, TN 38556
• 

  

  /24

  $49,900

  • Land
  • 6.56 Acres
  • $7,607 per Acre

  0 Cheyenne Dr Unit RTC3066556, Jamestown, TN 38556

  6.56 surveyed ac in a high prestige gated community (Rockcastle) located in the hills of TN with mtn views and privacy and security. Modest restrictions on file – in docs. Stream, level lot to a gentle roll terrain, several building sites with much potential, over 375 ft of paved road frontage, electric – telephone – high speed internet available – fiber optics to connect into, well developed

  Debra Dodd No 1 Quality Realty

  0 Cheyenne Dr Unit RTC3066556, Jamestown, TN 38556
• 

  

  /39

  $279,000

  • 4 Beds
  • 2 Baths
  • 2,052 Sq Ft

  111 Guffey Ln, Jamestown, TN 38556

  Charming brick ranch on 1.44 acres in a peaceful country setting! Situated on a spacious corner lot, this unrestricted property is ideal for a mini-farm and offers endless possibilities. The land features a fenced backyard, a separate fenced pasture, and a 36x32 pole barn—perfect for animals, equipment, or hobbies. Start your mornings on the covered front porch and enjoy the quiet surroundings.

  Donna Baisley Baisley Hometown Realty, LLC

  111 Guffey Ln, Jamestown, TN 38556
• 

  

  /58

  $118,733

  • Land
  • 11.61 Acres
  • $10,227 per Acre

  Lot 4 Shotgun Annie Rd, Jamestown, TN 38556

  11.61 surveyed totally wooded tract of land located in a rural - country location. Lovely area with loads of wildlife and fresh air. Modest restrictions but there is NO HOA. Mostly level terrain to a gentle roll. Over 600 paved road frontage with easy accessing the property. Underground electric, telephone, public water, internet, cell phone coverage & fiber optic available. Mtn views & views.

  Debra Dodd No. 1 Quality Realty-celina

  Lot 4 Shotgun Annie Rd, Jamestown, TN 38556
• 

  

  /49

  $2,882,045

  • 4 Beds
  • 6 Baths
  • 7,088 Sq Ft

  347 Charit Trail, Jamestown, TN 38556

  **The Pinnacle of Equestrian Luxury**Welcome to the crown jewel of Rock House Ranches - where world class equestrian living meets timeless mountain luxury. This 4-bedroom, 3.5-bath estate spans over 6,397 sq ft of refined craftsmanship, highlighted by 8' solid hand-scraped Amish hardwood flooring, Shaw designer carpet, and travertine stone finishes throughout. As you walk through this grand

  347 Charit Trail, Jamestown, TN 38556
• 

  

  /20

  $110,000

  • Land
  • 30,927 Sq Ft
  • $154,930 per Acre

  0 Eagle Unit 18, Jamestown, TN 38556

  Wonderful buildable level lot in the gated community of The Highlands Of Big South Fork. You can't find a better lot in the Highlands, and there are not many left. It is close to the owners barns and the lot comes with 2 stalls/paddocks anbd tack room in the owners barsn. Also, turn out pastures are available at a small monthly charge. No where else in Fentress county can you have access to 50

  Glenda Levin Mitchell Real Estate & Auction LLC

  0 Eagle Unit 18, Jamestown, TN 38556
• 

  

  /5

  $120,000

  • Land
  • 11.63 Acres
  • $10,318 per Acre

  0 Lot 13 Stirrup Ln, Jamestown, TN 38556

  Hunter's Ridge Equestrian Subdivision is a gated community offering peaceful country living with easy access to Jamestown, Crossville, and Cookeville. This gently rolling 11.63-acre lot provides ample space—ideal for building your dream home and accommodating horses. Restrictions apply. Conveniently located just off Highway 127, the subdivision is close to East Fork Stables, with the renowned Big

  Cindy Stedman Allardt Real Estate Association LLC

  0 Lot 13 Stirrup Ln, Jamestown, TN 38556
• 

  

  /4

  $28,500

  • Land
  • 1.73 Acres
  • $16,474 per Acre

  0 Old Wolf River Rd, Jamestown, TN 38556

  Wooded surveyed 1.73 +/- acres in great location for all of the amenities in the City of Jamestown, close to Pine Haven Elementary and York High School. Utilities available along road frontage, power line easement across on one side of property. No restrictions, Just minutes to the access onto Hwy 127. All three lots combined is 5.03 acres and can be bought altogether

  Deborah Mountain Bestway Realty

  0 Old Wolf River Rd, Jamestown, TN 38556
• 

  

  /15

  $109,900

  • Land
  • 51.63 Acres
  • $2,129 per Acre

  n/a Choctaw Dr, Jamestown, TN 38556

  Looking to live off the grid and embrace privacy and seclusion? This expansive wooded tract offers the perfect opportunity to create your own private retreat. With light restrictions and multiple potential building sites, the property is ideal for a family compound or a peaceful homestead. Enjoy abundant wildlife and the option to live simply and sustainably, surrounded by nature. Whether you're

  Rhonda Darrow Home Touch Realty LLC

  n/a Choctaw Dr, Jamestown, TN 38556
• 

  

  /4

  $39,900

  • Land
  • 3.57 Acres
  • $11,176 per Acre

  0 Panther Branch Rd Unit RTC2976916, Jamestown, TN 38556

  Look for unrestricted acreage to build your dream home? Corner acreage of 3.57 wooded acres. Minutes to all amenities, but far enough from the city lights & traffic.

  Rhonda Darrow Home Touch Realty

  0 Panther Branch Rd Unit RTC2976916, Jamestown, TN 38556

Showing Results 281 - 320, Page 8 of 9