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Fentress County TN Homes for Sale with Acreage

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  • /28

    $389,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    1468 Taylor Place Rd, Jamestown, TN 38556

    New construction! This beautiful 3-bedroom, 2-bath home offers over 1,550+ sq ft of thoughtfully designed living space, all on one level with a durable slab foundation. Featuring an open floor plan with a spacious kitchen and great room, this home is perfect for modern living and entertaining. The primary suite provides a private retreat with a large bath and walk-in closet. Situated on 1.51

    Agent Photo

    Todd Stephens

    Crye-Leike Brown Executive Realty

    (931) 281-6146

    1468 Taylor Place Rd, Jamestown, TN 38556
  • /60

    $375,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1978 Oloff Smith Rd, Allardt, TN 38504

    Do you love country living with the convenience of a modern well equipped manufactured home that is in wonderful condition. It has new flooring in many parts of the house and nice carpet in the bedrooms. Garden tub and walk in shower in the master bath and a full bathroom convenient to the other bedrooms. Separate dining room with eat in island in the modern kitchen. Large laundry and mud room

    Glenda Levin Mitchell Real Estate & Auction

    1978 Oloff Smith Rd, Allardt, TN 38504
  • /57

    $825,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,204 Sq Ft

    399 Annabelle Way, Jamestown, TN 38556

    Nestled on a private 2.07-acre cul-de-sac lot in Jamestown, TN, this exceptional luxury home offers a rare blend of refined living and natural beauty. Surrounded by mature trees and backing up to a peaceful greenbelt of forest acreage, the property features a serene creek and waterfall--creating a tranquil backyard retreat. Designed for both everyday living and entertaining, the home features a

    Wade Delk Blackwater Realty

    399 Annabelle Way, Jamestown, TN 38556
  • /39

    $49,900

    • Land
    • 5.52 Acres
    • $9,040 per Acre

    0 Hilltop Ln Unit 25449753, Wilder, TN 38589

    This beautiful 5.52-acre tract offers a peaceful, natural setting with mostly level terrain and a great mix of trees throughout. The property is fully wooded, featuring several mature hardwoods that provide shade, privacy, and character. A gentle gully adds interest to the landscape and could be an excellent spot to create a pond or water feature if desired. Electric and fiber-optic internet are

    Kimberly Rocha Freedom Realty Company Inc.

    0 Hilltop Ln Unit 25449753, Wilder, TN 38589
  • /36

    $799,900

    • Land
    • 243 Acres
    • $3,292 per Acre

    0 Boatland Rd, Jamestown, TN 38556

    Introducing a remarkable 243 +/- acres in Fentress County, Tennessee! The East Fork Obey River Paradise offers the ultimate recreational escape! With the East Fork of the Obey River forming its eastern boundary, the property provides direct access to outstanding water recreation, including rafting, kayaking, and excellent fishing opportunities! Whether you're seeking adventure or a spot to enjoy

    Brian Whitt Arrowhead Land Company

    0 Boatland Rd, Jamestown, TN 38556
  • /25

    $64,900

    • Land
    • 5.52 Acres
    • $11,757 per Acre

    911 Parkstown Extension, Wilder, TN 38589

    Escape to the mountains with this gorgeous 5.52 acre tract located on the Tennessees scenic Cumberland mountain plateau in the Wilder Mountain community. Property features a newly surveyed parcel with a long winding private driveway and gated entrance, and adjoins Panther Branch Creek and is situated between two well established homes no HOA but restrictions are in place no mobile homes, or tiny

    Kimberly Rocha Freedom Realty Company Inc.

    911 Parkstown Extension, Wilder, TN 38589
  • /10

    $45,900

    • Land
    • 5.71 Acres
    • $8,039 per Acre

    Ln, Wilder, TN 38589

    Fantastic 5.7 acres fully wooded with a trail, easily made into a driveway. The property has a nice gentle slope, perfect for homesteading. Minimal restrictions, no trailers, great for homesteading and an annual $200 road fee to keep the gravel roads well maintained.

    Kimberly Rocha Freedom Realty Company Inc.

    Ln, Wilder, TN 38589
  • /21

    $41,900

    • Land
    • 8.01 Acres
    • $5,231 per Acre

    0 W Bobcat Ln Unit 26106437, Wilder, TN 38589

    Beautiful 8.01-acre wooded mountain property offering a true in the mountains feel with gently rolling terrain. A seasonal creek runs through the property and it adjoins Big Piney Creek, adding to the natural landscape and outdoor appeal. The property includes an existing driveway and a cleared homesite, making it ready for your planswhether a weekend getaway or a future build. The wooded setting

    Kimberly Rocha Freedom Realty Company Inc.

    0 W Bobcat Ln Unit 26106437, Wilder, TN 38589
  • /27

    $340,000

    • Land
    • 66.25 Acres
    • $5,132 per Acre

    523 Honey Creek Loop Rd, Allardt, TN 38504

    This 66 +/- -acre tract sits on the Fentress and Scott County line in the heart of the Cumberland Plateau, offering direct access to one of Tennessee's most renowned outdoor recreation regions. The property is less than 1.5 miles from Big South Fork National River and Recreation Area and only moments from Honey Creek Overlook, Burnt Mill Bridge, and Honey Creek Horse Camp, where hundreds of miles

    Matt Carr National Land Realty

    523 Honey Creek Loop Rd, Allardt, TN 38504
  • /68

    $325,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,233 Sq Ft

    126 Indian Village Ln, Wilder, TN 38589

    Escape to your own private retreat with this spacious 4 bedroom 2 bath home tucked away on a beautiful 5.3 wooded acres on a quiet cul de sac. This home offers exceptional privacy, peaceful surroundings, and plenty of room to relax or entertain. Step inside to a bright, open layout with all appliances included and an oversized tub to unwind after a long day. A large deck overlooks the surrounding

    Kimberly Rocha Freedom Realty Co. Inc.

    126 Indian Village Ln, Wilder, TN 38589
  • /10

    $34,900

    • Land
    • 5.9 Acres
    • $5,915 per Acre

    0 Wilson Ridge Rd, Jamestown, TN 38556

    Off Grid paradise, 5.9 acres of desirable hunting land or recreational land. No amenities such as electric or city water are available. Heavily wooded, really untouched, like stepping back in time! Absolutely stunning property

    Kimberly Rocha Freedom Realty Company Inc.

    0 Wilson Ridge Rd, Jamestown, TN 38556
  • /14

    $325,000

    • Land
    • 34.75 Acres
    • $9,353 per Acre

    1354 E Obey Ln, Wilder, TN 38589

    Discover this rare find, 34.75 beautiful wooded acres offering privacy, natural beauty and rare river frontage. The property has ample gravel road frontage of 2785 feet, adjoins gorgeous East Obey River frontage of 1272 feet and even a natural spring fed pond. Features include a homesite, a permitted 2 bedroom septic system installed, gravel driveway, gate, and a 200 amp electrical service. No

    Kimberly Rocha Freedom Realty Company Inc.

    1354 E Obey Ln, Wilder, TN 38589
  • /16

    $69,900

    • Land
    • 5.09 Acres
    • $13,733 per Acre

    638 Flat Top View Ln, Wilder, TN 38589

    Escape to the beauty of the Cumberland Plateau in the scenic Wilder Mountain area. This fabulous tract is build ready with some of the hard work already done: The gravel driveway is installed, the homesite area cleared and ready, electric is on site and a well already in place. This gently rolling land is easy to build on and gives you plenty of space for a garden, animals , cabin or estate in

    Kimberly Rocha Freedom Realty Co. Inc.

    638 Flat Top View Ln, Wilder, TN 38589
  • /50

    $760,000

    • 3 Beds
    • 3 Baths
    • 1,790 Sq Ft

    2025 Allardt-Tinch Rd, Jamestown, TN 38556

    MOTIVATED SELLER - PRICED BELOW APPRAISED VALUE! Custom 2022-built homestead on 40.62 UNRESTRICTED ACRES in the heart of Tennessee horse country with privacy, infrastructure, and high-speed fiber internet already in place. Located at the end of a 1,000' private driveway, this low-maintenance property offers a rare combination of seclusion and convenience--just 10 minutes to town, 7 miles to East

    Stephanie Cross United Country Real Estate/Tennessee Real Properties

    2025 Allardt-Tinch Rd, Jamestown, TN 38556
  • /23

    $169,000

    • Land
    • 40 Acres
    • $4,225 per Acre

    0 Dry Creek Rd, Jamestown, TN 38556

    This 40 +/- acre wooded hillside property in Fentress County, Tennessee offers a great combination of natural beauty and recreational potential! Tucked away in a quiet part of the region, this tract provides a secluded setting that feels removed while still being accessible. The land is primarily wooded and features a natural change in elevation, sitting higher along the southern portion before

    Brian Whitt Arrowhead Land Company

    0 Dry Creek Rd, Jamestown, TN 38556
  • /22

    $324,900

    $75K PRICE DROP
    • Land
    • 35 Acres
    • $9,283 per Acre

    0 Sam Smith Rd Unit LotWP001 23395947, Allardt, TN 38504

    This stunning 35-acre property offers an exceptional combination of natural beauty and amenities. With gorgeous mountain views, approximately 15 acres of rolling pasture, and a peaceful stocked pond, the land is perfectly suited for a private homestead, recreational retreat, or small farm. The property boasts approximately 2,100 feet of road frontage across two roads, with utilities available

    Sean Maxwell Whitetail Properties Real Estate

    0 Sam Smith Rd Unit LotWP001 23395947, Allardt, TN 38504
  • /18

    $67,900

    • Land
    • 5.92 Acres
    • $11,470 per Acre

    0 Hood Ln Unit 23582805, Wilder, TN 38589

    Experience the natural beauty and serene lifestyle of Wilder Mountain, ideally located in the heart of the Cumberland Plateau. This almost 6 acres of gently rolling, wooded property presents a great opportunity to create your ideal retreatwhether thats a secluded estate home, a cozy mountain cabin, or a homestead to be proud of. The land offers ample acreage with plenty of room for barns,

    Kimberly Rocha Freedom Realty Company Inc.

    0 Hood Ln Unit 23582805, Wilder, TN 38589
  • /10

    $33,500

    • Land
    • 6.83 Acres
    • $4,905 per Acre

    0 Wilson Ridge Rd, Jamestown, TN 38556

    Off Grid paradise, 6.83 acres of desirable hunting land or recreational land. No amenities such as electric or city water are available. Heavily wooded, really untouched, like stepping back in time! Absolutely stunning property

    Kimberly Rocha Freedom Realty Company Inc.

    0 Wilson Ridge Rd, Jamestown, TN 38556
  • /26

    $68,500

    $1K PRICE DROP
    • Land
    • 5.39 Acres
    • $12,709 per Acre

    0 Valley View Cir Unit 22837501, Wilder, TN 38589

    This parcel is a bluff view and has a driveway already for your dream home. Very rural and private area of Wilder Mountain. Off Hillcamp Road. Sign on property. Lots of wildlife on private gravel road. Annual road maintenance fee of $200, but no homeowners association great for your on or off grid home. Deed restrictions are in place to keep property values.

    Kimberly Rocha Freedom Realty Company Inc.

    0 Valley View Cir Unit 22837501, Wilder, TN 38589
  • /111

    $5,250,000

    • 3 Beds
    • 2 Baths
    • 3,501 Sq Ft

    2965 S York Hwy, Jamestown, TN 38556

    A Rare Business & Real Estate Offering – 68 Acres in Fentress County, TNHighland Manor Winery, established in 1980, holds the distinction of being Tennessee’s oldest winery. Paired with Sawbriar Brewing, Fentress County’s first tap room, this property represents a unique dual-brand enterprise at the forefront of Tennessee’s food and beverage scene. Together, they deliver award-winning wines,

    Stephanie Cross United Country Real Estate / Tennessee Real Properties

    2965 S York Hwy, Jamestown, TN 38556
  • /7

    $49,900

    • Land
    • 6.18 Acres
    • $8,074 per Acre

    0 Panther Falls Rd, Wilder, TN 38589

    Perched on the scenic Cumberland Plateau this 6.18 acre parcel offers breathtaking mountain views and the soothing sounds of a waterfall you can hear right from your deck. The terrain is steep, adding to the dramatic vistas, with nature unfolding in every direction. No HOA, minimal restrictions and road fees help maintain year round access. Whether youre envisioning a secluded getaway cabin or a

    Kimberly Rocha Freedom Realty Company Inc.

    0 Panther Falls Rd, Wilder, TN 38589
  • /46

    $51,900

    $3K PRICE INCREASE
    • Land
    • 5.59 Acres
    • $9,284 per Acre

    6030 E Obey Ln, Wilder, TN 38589

    Discover the perfect blend of natural beauty and convenience on this 5.59 acre parcel with mountain views all around. A driveway is already in place and the property features a 200 amp electrical service and a completed soil test saving you time and expense as you prepare to build your dream home or getaway cabin. The land has very unique rock outcroppings, including one remarkable formation

    Kimberly Rocha Freedom Realty Company Inc.

    6030 E Obey Ln, Wilder, TN 38589
  • /39

    $54,900

    • Land
    • 5.58 Acres
    • $9,839 per Acre

    0 Hood Ln Unit 22915588, Wilder, TN 38589

    Welcome to Wilder Mountain in the heart of the beautiful Cumberland Plateau where peace, privacy, and possibility all come together. This nearly level, park-like property feels more like your own private nature preserve than a vacant lot. Towering hardwoods, open understory, and gentle terrain create a setting that's both breathtaking and incredibly usable.With an impressive 628 feet of

    Kimberly Rocha Freedom Realty Company Inc.

    0 Hood Ln Unit 22915588, Wilder, TN 38589
  • /77

    $89,000

    $61K PRICE DROP
    • Land
    • 9.31 Acres
    • $9,560 per Acre

    1023 Flat Rock Rd, Jamestown, TN 38556

    UNRESTRICTED - Endless Possibilities on 9.31 Acres! Escape to this peaceful 9.31-acre property offering privacy, natural beauty, and total freedom with no restrictions. A newly installed driveway and gated entrance lead to a charming 272 sq ft off-grid cabin with a 3/12 shingled roof-perfect for off-grid living, a weekend retreat, hunting cabin, Airbnb getaway, or a base while you build your

    Kimberly Rocha Freedom Realty Company Inc.

    1023 Flat Rock Rd, Jamestown, TN 38556
  • /24

    $179,900

    • Land
    • 17.6 Acres
    • $10,222 per Acre

    285 Purple Iris Ln, Wilder, TN 38589

    Beautiful wooded property on the Cumberland Plateau with stunning panoramic views. Located at the end of a cul de sac for maximum privacy, this tract features natural rock outcroppings and frontage on Big Piney Creed, with state owned land across the creek for lasting seclusion. No HOA, minimal restrictions, and an annual $200 road maintenance fee. Driveway already installed and perk tested for a

    Kimberly Rocha Freedom Realty Company Inc.

    285 Purple Iris Ln, Wilder, TN 38589
  • /42

    $429,900

    $9K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,584 Sq Ft

    317 Georgee Rd, Jamestown, TN 38556

    Welcome to 317 Georgee Rd - where privacy, comfort, and outdoor living come together beautifully. Situated on an impressive 1.25 acres, this well maintained property offers the kind of peaceful setting that's hard to find. Tucked away from the hustle and bustle, you'll immediately appreciate the privacy, mature landscaping, and thoughtfully designed outdoor spaces. The backyard is truly made for

    Gage Dople Wallace

    317 Georgee Rd, Jamestown, TN 38556
  • /59

    $575,000

    • 1 Bed
    • 1 Bath
    • 350 Sq Ft

    145 Horse Haven Rd, Allardt, TN 38504

    Public Remarks: Custom Built Cabarn on 8.82ac located in White Oak Equestrian Subdivision. Horse Lover Steal!! Access to the Big South Fork NR&RA is adjacent to property. Ride onto the O&W horse trail within minutes and let your journey begin. Includes everything you need for great riding vacations. There are also neighborhood horse and hiking trails. The 8.82 acres consist of 5 lots. The 1350 sf

    Don Guy Triple C Realty & Auction, LLC

    145 Horse Haven Rd, Allardt, TN 38504
  • /34

    $499,000

    $200K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 880 Sq Ft

    8225 Red Hill Rd, Jamestown, TN 38556

    New construction barndominium on 7.75 acres m/l with Wolf River frontage and stunning views of the rolling acres and Tennessee hills. The main level offers a finished flex space with half bath, ideal for a bedroom or office, plus approx. 1300 sq ft of open barn space with stall. The upper level features an open kitchen/living area with electric fireplace and large windows, full bath with laundry,

    Kelly Latham ReMax Country Living, LLC

    8225 Red Hill Rd, Jamestown, TN 38556
  • /39

    $399,000

    • 2 Beds
    • 2 Baths
    • 984 Sq Ft

    813 Bluebird Ridge Rd, Jamestown, TN 38556

    Nestled in the heart of equestrian country, this 2.01-acre tract in Ridge Top Acres offers the perfect blend of potential and peaceful country living. With just a bit more clearing and some fencing, this property will truly shine for horse enthusiasts or those seeking space to roam. Ideally located adjacent to Big South Fork Park, you'll enjoy endless riding trails and outdoor adventure right at

    Rhonda Darrow Home Touch Realty

    813 Bluebird Ridge Rd, Jamestown, TN 38556
  • /16

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    684 Spruce Creek Dr, Jamestown, TN 38556

    Two cozy cabins in Equestrian community with riding trails right off the property! Trails have direct access into Big South Fork Recreation Area to ride hundreds of miles through creeks, woods, waterfalls, rock structures. Can live in one cabin and rent out other! Rental history available. Larger cabin is 888 sq ft. 2 br 1 ba. With high ceilings and beautiful modern kitchen. Stainless steel

    Daniel Demers Sell Your Home Services, LLC

    684 Spruce Creek Dr, Jamestown, TN 38556
  • /52

    $625,000

    $25K PRICE INCREASE
    • 3 Beds
    • 4 Baths
    • 4,320 Sq Ft

    3251 Rugby Pike, Jamestown, TN 38556

    MOTIVATED SELLER! Located in the heart of Tennessee horse, Country, and Rich in the history of bygone times, this house can easily become the home you have always dreamed of. Positioned halfway between Jamestown and Rugby, Tennessee this 9.2 +/- acres property features a 3 bd/4 bath home w/ attached 2 car garage, a detached garage/workshop w/ wood furnace, a stocked pond, and fruit trees, such as

    Dusty Wells 1 Source Realty Pros

    3251 Rugby Pike, Jamestown, TN 38556
  • /49

    $639,900

    $45K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,989 Sq Ft

    105 Charity Ln, Jamestown, TN 38556

    BRAND NEW $22,000 ROOF & FLASHING installed 1/20/2026. STUNNING Traditional Styled home situated on 4.86 acres amongst the trees. Wrap around ASPHALT driveway. LARGE covered front porch with TREX decking, Mixture of Brick & HARDIE PLANK LAP SIDING Exterior. Mixture of flooring being HARDWOOD, TILE & CARPET. Generous open BONUS room above the garage heated & Cooled. Separate Laundry room. MANY

    Steve Diskin Burks Diskin Real Estate

    105 Charity Ln, Jamestown, TN 38556
  • /50

    $599,000

    • 2 Beds
    • 3 Baths
    • 3,886 Sq Ft

    617 Cheyenne Dr, Jamestown, TN 38556

    617 Cheyenne Drive, Jamestown, TN, +/- 3886 square feet, 2 bed, 3 bath, wtih walk out basement. This home is Tucked away in the woods at the end of a beautiful private drive. This stunning custom lodge-style home offers the perfect combination of peaceful seclusion and everyday convenience. Don't let the private setting fool you -- you're only about 10 minutes from Jamestown with easy access to

    Michelle Jones Eagle View Realty, LLC

    617 Cheyenne Dr, Jamestown, TN 38556
  • /60

    $695,000

    $5K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,600 Sq Ft

    1086 Pearl Hinds Rd, Jamestown, TN 38556

    Nestled on over 7 acres of mostly wooded land, this beautifully constructed brick home at 108 6 Pearl Hines Rd., Jamestown, Tennessee offers exceptional privacy, space, and versatility in a serene natural setting. With 3,600 square feet of thoughtfully designed living space, this property is ideal for both comfortable everyday living and entertaining. The home features three generously sized

    Dusty Wells 1 Source Realty Pros

    1086 Pearl Hinds Rd, Jamestown, TN 38556
  • /3

    $399,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,591 Sq Ft

    356 Annabelle Way, Jamestown, TN 38556

    A new construction home sitting on 1.98 surveyed acres home is 1591 S.F. with a 2 car garage features include 3 bedroom 2.5 baths granite counters stamped concrete front porch and deck encapsulated crawl space with moisture control tankless hot water and insulated siding with many more features a must see in a great area of Fentress Co.

    Bart Neely Bestway Realty

    356 Annabelle Way, Jamestown, TN 38556
  • /60

    $409,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,708 Sq Ft

    2510 Tinchtown Rd, Jamestown, TN 38556

    A remarkable 2 bedroom 2 full bath log home with a large wraparound porch and a 2 car garage 27x23 and a 405 s.f. apartment overhead, home features a large wood burning fireplace hardwood floors and a very large master bedroom the roof central H@A are less than 5 years old.The property is mainly wooded and features a small creek and a 40x40 pole barn a 16x20 storage shed that is a 2 story

    Bart Neely Bestway Realty

    2510 Tinchtown Rd, Jamestown, TN 38556
  • /59

    $395,900

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    101 Ridgepoint Rd, Jamestown, TN 38556

    This home is located in the beautiful equine community of Ridgetop in Jamestown, Tennessee. Home of the beautiful Big South Fork National Park and Recreation Area. People come from all over the United States to ride here. Over three acres of fenced property with no climb horse fence. Two 12x12 stalls in an enclosed barn and two open air stalls and a wash rack. Tack room and area for hay storage

    Glenda Levin Mitchell Real Estate & Auction

    101 Ridgepoint Rd, Jamestown, TN 38556
  • /58

    $444,000

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

    270 Maggie Valley Dr, Jamestown, TN 38556

    Privacy and nature at its finest! This spacious equestrian estate is tucked away at the end of the road on 7.6 +/- beautiful acres consisting of fenced pasture, wooded walking trails, and your own private creek and bluff with seasonal waterfall! All this beauty just 10 min from town! You are also aprox 10min to several Big south Fork NRRA trailheads, Pickett State park, and about 20min to East

    Erica Styles Allardt Real Estate Association LLC

    270 Maggie Valley Dr, Jamestown, TN 38556
  • /48

    $449,900

    $40K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,417 Sq Ft

    1128 Allardt Hwy, Jamestown, TN 38556

    This stone home has weather many a storms and just keeps standing strong, in immaculate condition, with so much character, recently updated with flooring, paint, lighting, drywall, cabinets, counter tops, appliances, and so much more you need to see it for yourself, built in flower planters on the front, concrete covered front & back porch. 2 bedroom 2 1/2 bath home with a spacious bonus room

    Rhonda Darrow Home Touch Realty, LLC

    1128 Allardt Hwy, Jamestown, TN 38556
  • /58

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,800 Sq Ft

    598 Ted Brooks Rd, Jamestown, TN 38556

    SPACIOUS LOG HOME is move in ready! All the beautiful items in home sell with home. Home is located at end of road in a pretty country setting, yet minutes to schools, stores and all the amenities the City of Jamestown has to offer. Open floor plan with cathedral ceiling, plentiful Custom Kitchen cabinets, including refrigerator , range/oven, microwave . dishwasher, garbage disposal . Spacious

    Deborah Mountain Bestway Realty

    598 Ted Brooks Rd, Jamestown, TN 38556

Showing Results 81 - 120, Page 3 of 10

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