Jamestown, KY Homes for Sale with Acreage

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  /55

  $379,900

  $15K PRICE DROP

  570 Little Indian Dr, Jamestown, KY 42629

  Welcome to your perfect getaway or full-time residence! This 3 bedroom, 2 bathroom home offers comfort, convenience, and incredible outdoor living-all in a unique, private setting just minutes from the water. Built in 2016 and maintained in pristine, move-in ready condition, this 1,152 sq ft home comes fully furnished, making it truly turnkey. Inside, you'll find a warm and inviting interior

  Rachel Bernard The Realty Firm

  570 Little Indian Dr, Jamestown, KY 42629
• 

  

  

  /29

  $75,000

  $4K PRICE DROP

  • Land
  • 1.73 Acres
  • $43,353 per Acre

  Lot 16 Twin Creeks Loop, Jamestown, KY 42629

  Ever dreamed of owning a true slice of paradise where the world simply disappears? This isn't just another building lot; it's the largest and most prestigious homesite in the subdivision, designed for those who value absolute peace and quiet. Nestled behind a natural screen of majestic, mature trees, the build site offers total seclusion and "room to roam." But the true magic happens when you

  Torsten Langguth Prosperity Real Estate

  Lot 16 Twin Creeks Loop, Jamestown, KY 42629
• 

  

  

  /4

  $45,500

  • Land
  • 1 Acre
  • $45,500 per Acre

  22 & 23 Cherry Loop, Jamestown, KY 42629

  Your Bardominum building site near Lake Cumberland. Gorgeous level to gently rolling 1acre of land just minutes from Jamestown Resort & Marina. Moderate restrictions..NO HOA. Paved roads, city water, electric and fiberoptic for fast internet.... Near several launching ramps. Two lots... 22 & 23 in Cherry Hill. Call for details.

  Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

  22 & 23 Cherry Loop, Jamestown, KY 42629
• 

  

  

  /5

  $120,000

  $30K PRICE DROP

  • Land
  • 2 Acres
  • $60,000 per Acre

  Tract 4-5 Clayton Rd, Jamestown, KY 42629

  2-acre unrestricted lot in the heart of Jamestown with city water and sewer access! This level lot offers privacy yet walking distance to shopping, restaurants, the library and city park. Here's your opportunity knocking. Great location for a residential home or big enough for apartments.

  Shelly Stoyell PCS Real Estate

  Tract 4-5 Clayton Rd, Jamestown, KY 42629
• 

  

  /2

  $45,200

  • Land
  • 1.13 Acres
  • $40,000 per Acre

  30 Leveridge Ct, Jamestown, KY 42629

  This lot has a beautiful creek that runs along the back border. Only 9 lots left in this beautiful 68-acre development. Paved Streets 1-13 acres available. All lots are heavily wooded. Restrictions allow for barndominiums, detached garages or buildings to accommodate boats and RV's. Located within a few miles of Jamestown Marina, State Dock Marina and Halcomb's Landing boat launch. Watch for

  Shelly Stoyell PCS Real Estate

  30 Leveridge Ct, Jamestown, KY 42629
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  /106

  $724,900

  Open Sat 12PM - 2PM $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,200 Sq Ft

  176 Wetland Dr, Jamestown, KY 42629

  Rare Cumberland River Farm Opportunity - 26 Private Acres! Welcome to your own slice of paradise in the breathtaking Cumberland River Valley! This exceptional one-owner property offers 26 acres of level, picturesque land with a setting that is truly second to none. Whether you're looking for a private retreat, working farm, hunting property, or forever home, this one has it all. The land features

  Ashly Smith Lake Cumberland Real Estate Professionals

  176 Wetland Dr, Jamestown, KY 42629
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  /63

  $375,000

  $24K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  554 N Main St, Jamestown, KY 42629

  A staple in Jamestown since the 1930s, this offers exceptional curb appeal and a fantastic location. It features an inviting covered front and side porch, providing a welcoming entry. Inside, you'll find original hardwood floors, a clawfoot tub, and exquisite woodworking that highlight the home's historical charm. Over the years, tasteful updates have been made, preserving the unique character of

  Shelly Stoyell PCS Real Estate

  554 N Main St, Jamestown, KY 42629
• 

  

  /4

  $15,000

  • Land
  • 1.89 Acres
  • $7,937 per Acre

  86 Peninsula, Jamestown, KY 42629

  Looking for a nice big (1.95 Ac.) building site for your new home at Lake Cumberland? Check this one out. The Peninsula Development is a gated community just a few minutes away from Pleasant Hill Boat Ramp and Historic Jamestown. Call today for more info!!!

  Josh McKinley Mckinley Real Estate Group

  86 Peninsula, Jamestown, KY 42629
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  /48

  $749,900

  • 3 Beds
  • 4 Baths
  • 2,830 Sq Ft

  106 Airport Rd, Jamestown, KY 42629

  Welcome to 106 Airport Road in Jamestown, Kentucky—a custom-built 2023 barndominium situated on approximately 3.36 acres within the Jamestown city limits. Constructed by SBC LLC, this property combines quality craftsmanship, spacious living, and an exceptional garage setup, all within minutes of Lake Cumberland and Safe Harbor Marina. The home offers approximately 2,830 square feet of finished

  Ashley Stearnes CENTURY 21 Advantage Realty

  106 Airport Rd, Jamestown, KY 42629
• 

  

  /79

  $799,900

  • 3 Baths
  • 4,661 Sq Ft

  2367 U S 127 Business, Jamestown, KY 42629

  Mini Indy: A Premier Go-Kart and Family Fun Center Welcome to Mini Indy, an exhilarating go-kart and family fun center situated just off Highway 127 in Jamestown, Kentucky. This unique property spans 3.3 acres and boasts a 60x80 steel building housing over 50 arcade games, a concessions area complete with a beer license, and a thrilling 960-foot go-kart track with 11 go-karts ready to go. For

  Mary Dotson CENTURY 21 Advantage Realty

  2367 U S 127 Business, Jamestown, KY 42629
• 

  

  /30

  $200,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  228 Cooper Rd, Jamestown, KY 42629

  Lake life meets peaceful country living in this charming Jamestown retreat just MINUTES from beautiful Lake Cumberland! If you’ve been dreaming of a place where you can relax, spread out, and enjoy the outdoors, this 3 bedroom, 2 full bathroom home checks all the right boxes! Situated on a permanent foundation and tucked away in a quiet rural setting, this home offers the perfect blend of

  Morgan Austin EXIT REALTY BLUEGRASS

  228 Cooper Rd, Jamestown, KY 42629
• 

  

  /24

  $479,900

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  8790 S Highway 127, Jamestown, KY 42629

  Experience the perfect blend of luxury, recreation, and privacy in this stunning 3,000 sq. ft. custom barndominium nestled on 1.8 serene, wooded acres and backing up to the beauty of Lake Cumberland. Designed for both elegant living and lake life, this exceptional property also could be a permanent residence or an Airbnb, featuring 1,500 sq. ft. of beautifully finished living space paired with an

  Christy Estep CENTURY 21 Advantage Realty

  8790 S Highway 127, Jamestown, KY 42629
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  /35

  $319,000

  • 3 Beds
  • 2.5 Baths
  • 2,208 Sq Ft

  2390 W Highway 92, Jamestown, KY 42629

  One doesn't just buy a home like this, it becomes a part of you, and you become a part of the history that surrounds this great place. Known locally and the "Phelps Acres" home, this gorgeous 151 year old home was built on land that was conveyed to the Phelps family via a land grant for the elder Phelps' service in the American Revolution. In 1875 this amazing home purportedly replaced earlier

  Ken Hill Patriot Realty - Auction LLC

  2390 W Highway 92, Jamestown, KY 42629
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  /63

  $559,800

  $135K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,500 Sq Ft

  1655 Kentucky 92, Jamestown, KY 42629

  Just minutes away from Lake Cumberland and the Jamestown Resort & Marina, this 3500 sq. ft. building is brimming with potential. Boasting two bathrooms and an ample parking area. Building would be a great residence with a little work or could be used as retail. The property's prime location and curb appeal make it a standout opportunity. On top of that, there's a 5-unit efficiency style

  Darren Gossage Weichert Realtors Ford Brothers, Inc.

  1655 Kentucky 92, Jamestown, KY 42629
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  /14

  $45,000

  $5K PRICE DROP

  • Land
  • 1.5 Acres
  • $30,000 per Acre

  93 Laurel Rd, Jamestown, KY 42629

  Fox Point offers peace and calmness, but still has those great lake views that everyone is seeking. Hard to find a gem like this 1.5 acres, wooded. This would be a great place to build your dream home or vacation get away on Lake Cumberland. 4.5 miles to Lily Creek Boat Ramp, 6 miles to Jamestown Marina, 7 miles to Clifty Creek boat launching area, and 13 miles to Lake Cumberland State Dock. Only

  Ryne Tolar Lake And Land Realty Inc

  93 Laurel Rd, Jamestown, KY 42629
• 

  /2

  $489,900

  • 6 Beds
  • 5 Baths
  • 4,788 Sq Ft

  100 Sunset Dr, Jamestown, KY 42629

  Discover an outstanding investment opportunity in Jamestown, Kentucky! Situated on 7.41 beautiful acres, this fully rented multi-unit property has a strong rental history and offers immediate income potential. The property features three separate rental units. Two units offer 2 bedrooms and 1.5 bathrooms, while the third unit includes 2 bedrooms and 1 bathroom. Each unit is individually metered

  Ryne Tolar Lake And Land Realty Inc

  100 Sunset Dr, Jamestown, KY 42629
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  /119

  $669,000

  Open Sun 12PM - 2PM $30K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 5,235 Sq Ft

  135 Laurel Rd, Jamestown, KY 42629

  Seller offering up to $10,000 toward buyer updates, improvements, furnishings, or closing costs with an acceptable full-price offer for this spacious custom-built lake home, designed for comfort, style, and plenty of room to gather. Offered with two additional lakeview lots (Lots #2 and #3), this property totals approximately 1.67 acres, providing extra space, privacy, and long-term flexibility

  Torsten Langguth Prosperity Real Estate

  135 Laurel Rd, Jamestown, KY 42629
• 

  

  /44

  $399,900

  • 3 Beds
  • 4 Baths
  • 2,463 Sq Ft

  67 Balcony Bend Rd, Jamestown, KY 42629

  Welcome to this charming Lake Cumberland retreat nestled on 1.12 private, wooded acres in a quiet lake community with no HOA. This property offers all the benefits of a 5 bedroom footprint at a highly competitive price point... 3 traditional bedrooms and 2 additional lower-level flex rooms furnished as bedrooms. Surrounded by mature trees and scenic beauty, this inviting home offers the perfect

  Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

  67 Balcony Bend Rd, Jamestown, KY 42629
• 

  

  /91

  $410,000

  $79K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft

  1089 Warner Ridge Rd, Jamestown, KY 42629

  This beautiful 10 acre property offers everything you need for country living, featuring a barn with a full loft and stairs, concrete floors, water & electric, a feed and tack room, a turnout lot. The farmhouse, barn, and garages all have city water, and a circle driveway leads to the charming 3 bedroom, one bath home, which has been updated with refinished hardwood floors, new plumbing HVAC,

  Shelly Stoyell PCS Real Estate

  1089 Warner Ridge Rd, Jamestown, KY 42629
• 

  

  /3

  $18,000

  $1K PRICE DROP

  • Land
  • 1.2 Acres
  • $15,000 per Acre

  Lot 62 & 63 Captain's Point Subdivision, Jamestown, KY 42629

  Lots 62 & 63 of the Captain's Point Subdivision. Consist of 1.2 acres.

  Will Childers WTC Realty LLC

  Lot 62 & 63 Captain's Point Subdivision, Jamestown, KY 42629
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  /33

  $365,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,256 Sq Ft

  495 Pumpkin Creek Cir, Jamestown, KY 42629

  Situated on Pumpkin Creek Circle, this cabin offers an unbeatable location near Lake Cumberland State Resort Park and just minutes from Rowena Landing. Enjoy quick access to the water, nearby trails, and all the recreational opportunities that make Lake Cumberland one of the top lake destinations in the country. Ideal for both personal use or investment...short term rentals are welcome. Whatever

  Tina Clay CENTURY 21 Advantage Realty

  495 Pumpkin Creek Cir, Jamestown, KY 42629
• 

  

  /33

  $179,900

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  290 Denmark Ln, Jamestown, KY 42629

  Looking for room to spread out without sacrificing convenience? This beautiful 3 bedroom, 2 bathroom home offers 1,792 square feet of comfortable living space on 2 private, usable acres, creating the perfect blend of peaceful country living and everyday convenience. Just minutes from town and only 8 miles to both Lake Cumberland and the Cumberland River, this property is ideal for those who love

  Elliot Burton Golden Rule - Wilson Real Estate & Auction #2 LLC

  290 Denmark Ln, Jamestown, KY 42629
• 

  

  /19

  $154,000

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,784 Sq Ft

  266 Brown Rd, Jamestown, KY 42629

  Kasey Grayum Country Folks Realty & Auction, Inc.

  266 Brown Rd, Jamestown, KY 42629
• 

  

  /31

  $240,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  2440 S Highway 379, Jamestown, KY 42629

  Seize the opportunity to own a well-established Airbnb river retreat! Spanning 1.41 acres, this property is situated just 1 mile from Helm's Landing launch ramp and the Creelsboro store. Revel in the dual benefits of a revenue-generating home and a personal vacation haven—it's a logical choice! The retreat features 3 bedrooms, 2 full baths, and a spacious living room complete with a fireplace.

  Shelly Stoyell PCS Real Estate

  2440 S Highway 379, Jamestown, KY 42629
• 

  

  /44

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 3,226 Sq Ft

  1125 S Highway 2284, Jamestown, KY 42629

  Discover the perfect blend of country living and multi-generational convenience in the beautiful Lake Cumberland area! Situated on 17.62 acres m/l, this spacious 3-bedroom, 2.5-bath home offers an ideal setup for two families with separate entrances to both the main level and the fully finished basement. The lower level features its own kitchen, separate washer and dryer hookups, and private

  Simon Wilson Golden Rule - Wilson Real Estate and Auction #1, LLC

  1125 S Highway 2284, Jamestown, KY 42629
• 

  

  /5

  $71,000

  • Land
  • 2.39 Acres
  • $29,707 per Acre

  40 Dogwood Hollow Rd, Jamestown, KY 42629

  Only 9 lots left in this beautiful 68-acre development. Paved roads 1-13 acres available. All lots are heavily wooded. Restrictions allow for barndominiums, detached garages or buildings to accommodate boats and RV's. Located within a few miles of Jamestown Marina, State Dock Marina and Halcomb's Landing boat launch. Watch for resident wildlife when driving through. Come check it out, you'll love

  Shelly Stoyell PCS Real Estate

  40 Dogwood Hollow Rd, Jamestown, KY 42629
• 

  

  /3

  $800,000

  • Land
  • 3 Acres
  • $266,667 per Acre

  1142 N Main St, Jamestown, KY 42629

  Larry Sanner In The Loop Realty

  1142 N Main St, Jamestown, KY 42629
• 

  

  /9

  $299,900

  • Land
  • 25.08 Acres
  • $11,958 per Acre

  3 Nelson Mill Rd, Jamestown, KY 42629

  Over 25 acres of open land that is ideal for development, farming, or other use. There are no zoning requirements. Offered 'As Is'.

  Gary Justice The Solutions Group KY, LLC

  3 Nelson Mill Rd, Jamestown, KY 42629
• 

  

  /35

  $299,900

  New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,275 Sq Ft

  131 Pumpkin Creek Cir, Jamestown, KY 42629

  Situated on Pumpkin Creek Circle, this cabin offers an unbeatable location near Lake Cumberland State Resort Park and just minutes from Rowena Landing. Enjoy quick access to the water, nearby trails, and all the recreational opportunities that make Lake Cumberland one of the top lake destinations in the country. Ideal for both personal use or investment...short term rentals are welcome. Whatever

  Tina Clay CENTURY 21 Advantage Realty

  131 Pumpkin Creek Cir, Jamestown, KY 42629
• 

  

  /98

  $475,000

  $20K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 6,048 Sq Ft

  223 Lakeview Dr, Jamestown, KY 42629

  Welcome to refined living in the highly sought-after Lily Creek Resort in Jamestown. This exceptional brick and vinyl residence offers an impressive blend of space, comfort, and thoughtful design—perfect for those who appreciate both elegance and functionality. With over 6,000 square feet of finished living space, this meticulously maintained home is designed for both everyday living and

  Elaine Rowlett Southern Nest Realty, LLC

  223 Lakeview Dr, Jamestown, KY 42629
• 

  

  /70

  $599,000

  Open Sat 8AM - 10AM $51K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,954 Sq Ft

  255 Lantern Way, Jamestown, KY 42629

  Welcome to Lake Cumberlands newest SHOW STOPPER! Better than new and thoughtfully designed, this 2023 modern craftsman blends luxury finishes, smart design, and timeless character right here in the heart of Jamestown, KY in the highly sought after gated community- The Oaks! Offering 4 bedrooms and 3 full baths. The main level features 10' ceilings, 8' doors, and European oak engineered hardwood

  Heather Flanagan Keller Williams Legacy Group

  255 Lantern Way, Jamestown, KY 42629
• 

  

  /60

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  5029 S Highway 379, Jamestown, KY 42629

  Welcome to your own slice of Kentucky paradise in Creelsboro, just minutes from the charm of Jamestown. Located conveniently along the Cumberland River this home is between two public launch ramps Helm's Landing and Winfreys Ferry. Nestled on 9+ acres of fully fenced, gently rolling farmland, this property is the perfect blend of comfort, function, and rural beauty. Designed with both everyday

  Heather Flanagan Keller Williams Legacy Group

  5029 S Highway 379, Jamestown, KY 42629
• 

  

  /6

  $29,900

  • Land
  • 1.1 Acres
  • $27,182 per Acre

  26 Arrowhead Ln, Jamestown, KY 42629

  What a beautiful piece of ground within 1 mile of Pleasant Hill Boat Ramp. 3 lots totaling 1.1 +/- acre bordering a seasonal small creek off Arrowhead Lane. Can build a dream home or can put 2-3 tiny homes and put on airBnB. Lots 26, 27, & 28

  Tina Clay CENTURY 21 Advantage Realty

  26 Arrowhead Ln, Jamestown, KY 42629
• 

  

  /6

  $135,000

  • Land
  • 4.45 Acres
  • $30,337 per Acre

  35 Leveridge Ct, Jamestown, KY 42629

  Only 9 lots left in this beautiful 68-acre development. Paved streets. 1-13 acres available. All lots are heavily wooded. Restrictions allow for barndominiums, detached garages or buildings to accommodate boats and RV's. Located within a few miles of Jamestown Marina, State Dock Marina and Halcomb's Landing boat launch. Please watch for resident wildlife when driving through. Come check it out,

  Shelly Stoyell PCS Real Estate

  35 Leveridge Ct, Jamestown, KY 42629
• 

  

  /91

  $449,000

  $36K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,120 Sq Ft

  935 Clifty Creek Rd, Jamestown, KY 42629

  Lake Cumberland Log Home | 3,120 Sq Ft | Minutes to Two Boat Ramps. Whether you're searching for a full-time residence, weekend getaway, or family retreat, this one-of-a-kind log home offers the perfect combination of craftsmanship, space, and location. Situated just minutes from both Clifty Creek Boat Ramp and Holcomb's Landing at Wolf Creek Dam, you'll enjoy quick and convenient access to some

  Whitney Marcum Lake Cumberland Properties, Ltd. Co.

  935 Clifty Creek Rd, Jamestown, KY 42629
• 

  

  /35

  $380,000

  New Construction $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,256 Sq Ft

  223 Pumpkin Creek Cir, Jamestown, KY 42629

  Situated on Pumpkin Creek Circle, this cabin offers an unbeatable location near Lake Cumberland State Resort Park and just minutes from Rowena Landing. Enjoy quick access to the water, nearby trails, and all the recreational opportunities that make Lake Cumberland one of the top lake destinations in the country. Ideal for both personal use or investment...short term rentals are welcome. Whatever

  Tina Clay CENTURY 21 Advantage Realty

  223 Pumpkin Creek Cir, Jamestown, KY 42629
• 

  

  /33

  $380,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,256 Sq Ft

  443 Pumpkin Creek Rd, Jamestown, KY 42629

  Lot#15 1.175 Acres +/- Situated on Pumpkin Creek Circle, this cabin offers an unbeatable location near Lake Cumberland State Resort Park and just minutes from Rowena Landing. Enjoy quick access to the water, nearby trails, and all the recreational opportunities that make Lake Cumberland one of the top lake destinations in the country. Ideal for both personal use or investment...short term rentals

  Tina Clay CENTURY 21 Advantage Realty

  443 Pumpkin Creek Rd, Jamestown, KY 42629
• 

  

  /5

  $89,000

  • Land
  • 1.49 Acres
  • $59,732 per Acre

  7 Sunset Dr, Jamestown, KY 42629

  Beautiful Private Wooded Lake View Lot 1.49 acres on Pumpkin Creek, Jamestown, KY

  Anthony Gigilo ListWithFreedom.com

  7 Sunset Dr, Jamestown, KY 42629
• 

  

  /27

  $599,000

  • Land
  • 3.31 Acres
  • $180,967 per Acre

  000 Litton Dr, Jamestown, KY 42629

  Here's your chance to own an absolutely AMAZING 3.31-acre property with stunning lake views! Tucked away in the beautiful Lilly Creek Cove of Lake Cumberland, this spot is perfect for building the dream home you've always envisioned, complete with panoramic views of the water. Enjoy the perfect mix of seclusion while being just a stone's throw from Jamestown and the bustling Jamestown Marina.

  Darren Gossage Weichert Realtors Ford Brothers, Inc.

  000 Litton Dr, Jamestown, KY 42629
• 

  

  /47

  $380,000

  New Construction $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,256 Sq Ft

  255 Pumpkin Creek Cir, Jamestown, KY 42629

  Situated on Pumpkin Creek Circle, this cabin offers an unbeatable location near Lake Cumberland State Resort Park and just minutes from Rowena Landing. Enjoy quick access to the water, nearby trails, and all the recreational opportunities that make Lake Cumberland one of the top lake destinations in the country. Ideal for both personal use or investment...short term rentals are welcome. Whatever

  Tina Clay CENTURY 21 Advantage Realty

  255 Pumpkin Creek Cir, Jamestown, KY 42629

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