Jamestown, KY Homes

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  /89

  $599,000

  • 2 Beds
  • 3 Baths
  • 2,909 Sq Ft

  8860 U S 127, Jamestown, KY 42629

  Marina within minutes!!!! Welcome to "Bourbon Brown," a secluded lake cabin tucked into "Little Gold Diggers Cove on Lake Cumberland. This charming 2-bedroom, 3-bath retreat offers 1,893 sq ft of gross living area plus an additional 1,016 sq ft finished walk-out basement, creating generous space for both everyday living and entertaining. Built with durable 2×6 framing and Fiber Cement siding, the

  

  Penny Cartwright

  Platinum Home Realty

  (270) 544-0730

  8860 U S 127, Jamestown, KY 42629
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  /33

  $280,000 Sold Oct 28, 2025

  651 & 671 S Main St, Jamestown, KY 42629

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft

  Last Sold Summary

  • 56% Above List Price
  • $249/SF
  • 83 Days On Market

  Current Estimated Value $153,723

  Last Listing Agent The Dream Team Real Estate Professionals - Dreama Bolin Lake Cumberland Real Estate Professionals

  651 & 671 S Main St, Jamestown, KY 42629
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  /39

  Est $333,684 Not Listed For Sale

  280 E Cumberland Ave, Jamestown, KY 42629

  • 3 Beds
  • 3 Baths
  • 3,030 Sq Ft
  • Built 2005

  280 E Cumberland Ave, Jamestown, KY 42629

  Last Sold Summary

  • 24% Above List Price
  • $89/SF
  • 226 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Vicki Hines Keller Williams Bluegrass Realty - Lake Cumberland
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  /72

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  51 Morning Dove Dr, Jamestown, KY 42629

  LAKEVIEW LIVING at its finest—this is the one buyers wait for. Ideally positioned between Jamestown Marina and Lake Cumberland State Dock, this stunning 1.5-story log cabin offers the perfect blend of rustic charm, modern upgrades, and unforgettable views overlooking Clifty Creek. Step inside to an inviting open-concept main level featuring a warm and welcoming living area, spacious dining space,

  Darren Gossage Weichert Realtors Ford Brothers, Inc.

  51 Morning Dove Dr, Jamestown, KY 42629
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  /44

  $274,000 Sold Aug 11, 2025

  547 Lakeview Dr, Jamestown, KY 42629

  • 4 Beds
  • 2 Baths
  • 2,044 Sq Ft
  • Built 1997

  Last Sold Summary

  • 21% Below List Price
  • $134/SF
  • 161 Days On Market

  Current Estimated Value $287,169

  Last Listing Agent Torsten Langguth Prosperity Real Estate

  547 Lakeview Dr, Jamestown, KY 42629
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  /68

  Est $287,754 Not Listed For Sale

  1363 Harbor Springs Rd, Jamestown, KY 42629

  • 2 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  1363 Harbor Springs Rd, Jamestown, KY 42629

  Last Sold Summary

  • 9% Above List Price
  • $207/SF
  • 2 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Kimberly Byrom Lake Cumberland Properties, Ltd. Co.
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  /28

  $550,000

  • 8 Beds
  • 8 Baths

  786 Ray Man Rd, Jamestown, KY 42629

  Incredible Investment Opportunity in Wolf Creek Dam area! Are you looking for a property with endless possibilities? This modern motel offers a rare chance to own a prime piece of real estate in one of the most sought-after lake areas. Sitting on over 3 acres and featuring 8 fully furnished rooms, this property is truly one of a kind. Property Highlights: • 8 rooms - each with double queen beds •

  Rachel Bernard The Realty Firm

  786 Ray Man Rd, Jamestown, KY 42629
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  /2

  $16,000 Sold Dec 01, 2025

  Lots 101 & 102 Captains Point, Jamestown, KY 42629

  • Land
  • 2 Acres
  • $8,000 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Darren Gossage Weichert Realtors Ford Brothers, Inc.

  Lots 101 & 102 Captains Point, Jamestown, KY 42629
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  /9

  Est $115,365 Not Listed For Sale

  185 Jefferson St, Jamestown, KY 42629

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  185 Jefferson St, Jamestown, KY 42629

  Last Sold Summary

  • 66% Above List Price
  • $72/SF
  • 164 Days On Market

  Last Sold Price $69,500

  Last Listing Agent Darren Gossage Weichert Realtors Ford Brothers, Inc.
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  /46

  $365,000

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

  495 Pumpkin Creek Cir, Jamestown, KY 42629

  Barbara McWhorter The Realty Firm - Byrdstown

  495 Pumpkin Creek Cir, Jamestown, KY 42629
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  /68

  $154,000 Sold Mar 20, 2026

  145 State Park Rd Unit S4, Jamestown, KY 42629

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  Last Sold Summary

  • 17% Below List Price
  • $171/SF
  • 75 Days On Market

  Last Listing Agent Scotty Carter Lake Cumberland Real Estate Professionals

  145 State Park Rd Unit S4, Jamestown, KY 42629
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  /53

  Est $424,291 Not Listed For Sale

  629 Highway 1058, Jamestown, KY 42629

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1971

  629 Highway 1058, Jamestown, KY 42629

  Last Sold Summary

  • 25% Above List Price
  • $233/SF
  • 397 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Robert Corder CENTURY 21 Advantage Realty
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  /57

  $499,990

  • 3 Beds
  • 3 Baths
  • 4,110 Sq Ft

  398 Carriage Ln, Jamestown, KY 42629

  Located at 398 Carriage Lane in Jamestown, KY, this well-maintained home offers over 4,000 finished square feet of living space (more or less) and is situated on approximately .59 acres in the private, gated Oaks community. The home features 3 bedrooms with an additional room in the finished basement currently being used as a bedroom with a closet, along with 3 full bathrooms. The main level

  Ashley Stearnes CENTURY 21 Advantage Realty

  398 Carriage Ln, Jamestown, KY 42629
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  /2

  $272,000 Sold Apr 28, 2025

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,668 Sq Ft
  • Built 1995

  Last Sold Summary

  • $102/SF

  Current Estimated Value $253,626

  Last Listing Agent Lula Jean Burton RE/MAX LakeTime Realty

  Unlisted Address
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  /14

  Est $254,581 Not Listed For Sale

  416 Golf Trail Rd, Jamestown, KY 42629

  • 3 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 2000

  416 Golf Trail Rd, Jamestown, KY 42629

  Last Sold Summary

  • 38% Above List Price
  • $82/SF
  • 19 Days On Market

  Last Sold Price $184,000

  Last Listing Agent Lisa Coffey Weichert Realtors Ford Brothers, Inc.
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  /55

  $395,000

  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
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  /38

  $275,000 Sold Jul 01, 2025

  111 Safe Harbor Ln, Jamestown, KY 42629

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $196/SF
  • 118 Days On Market

  Current Estimated Value $340,844

  Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

  111 Safe Harbor Ln, Jamestown, KY 42629
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  /46

  Est $253,874 Not Listed For Sale

  356 W Cumberland Ave, Jamestown, KY 42629

  • 3 Beds
  • 2.5 Baths
  • 1,708 Sq Ft

  356 W Cumberland Ave, Jamestown, KY 42629

  Last Sold Summary

  • 24% Above List Price
  • $120/SF
  • 51 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.
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  /76

  $349,999

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

  139 Payton Ln, Jamestown, KY 42629

  Claim your own piece of paradise down a quiet gravel lane in Russell County, Kentucky. Privacy and seclusion is yours in this quaint lake cottage, nestled in dense woods high above the convergence of Wolf Creek, Lily Creek and Caney Creek on Lake Cumberland. This home has been gently loved for decades by the current owners. The roof of the house was replaced in summer, 2025. The detached two-car

  Charlotte Ikerd Key Players Real Estate

  139 Payton Ln, Jamestown, KY 42629
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  /17

  $80,000 Sold Jun 18, 2025

  0 Unit 25008827, Jamestown, KY 42629

  • 2 Beds
  • 1 Bath
  • 500 Sq Ft

  Last Sold Summary

  • 11% Below List Price
  • $160/SF
  • 6 Days On Market

  Last Listing Agent Darren Gossage Weichert Realtors Ford Brothers, Inc.

  0 Unit 25008827, Jamestown, KY 42629
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  /78

  Est $295,698 Not Listed For Sale

  258 K L G Dr, Jamestown, KY 42629

  • 3 Beds
  • 2.5 Baths
  • 1,719 Sq Ft
  • Built 2005

  258 K L G Dr, Jamestown, KY 42629

  Last Sold Summary

  • 1% Below List Price
  • $175/SF
  • 42 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Lula Jean Burton RE/MAX
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  /57

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft

  186 Lily Creek Resort Rd, Jamestown, KY 42629

  If you've been searching for a truly one-of-a-kind home in the Lake Cumberland area, this is it. Completed at the end of 2024, this custom-built property still feels brand new. Lightly lived in and meticulously maintained, offering that sought-after new construction look, feel, and even smell. Situated in the desirable Lily Creek Resort community in Jamestown, Kentucky, this property also

  Matthew Fouch Keller Williams Commonwealth - Somerset

  186 Lily Creek Resort Rd, Jamestown, KY 42629
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  /13

  $12,500 Sold Dec 29, 2025

  1112 Golf Trail, Jamestown, KY 42629

  • Land
  • 0.95 Acre
  • $13,158 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 27 Days On Market

  Last Listing Agent Kim Arehart Weichert Realtors Ford Brothers, Inc.

  1112 Golf Trail, Jamestown, KY 42629
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  /47

  Est $286,123 Not Listed For Sale

  4932 S Highway 379, Jamestown, KY 42629

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 1935

  4932 S Highway 379, Jamestown, KY 42629

  Last Sold Summary

  • 8% Above List Price
  • $116/SF
  • 91 Days On Market

  Last Sold Price $265,900

  Last Listing Agent Brooke Cooper CENTURY 21 Advantage Realty
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  /67

  $368,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  141 Cherokee Springs Ct, Jamestown, KY 42629

  Earn instant equity with this beautiful home, priced well-below appraised value! Comparable to a new-build in many ways, this immaculate, custom-built house is one of the best choices on the market! And lake lovers will appreciate the location—only two minutes from Lake Cumberland's Pleasant Hill Boat Ramp. This beautifully maintained 4-bed, 2.5-bath home has recent updates including stunning

  Charlotte Ikerd Key Players Real Estate

  141 Cherokee Springs Ct, Jamestown, KY 42629
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  /40

  $157,000 Sold Aug 08, 2025

  1023 Harbor Springs Rd, Jamestown, KY 42629

  • 2 Beds
  • 1 Bath
  • 1,440 Sq Ft

  Last Sold Summary

  • 21% Below List Price
  • $109/SF
  • 47 Days On Market

  Current Estimated Value $184,634

  Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

  1023 Harbor Springs Rd, Jamestown, KY 42629
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  /39

  Est $192,356 Not Listed For Sale

  803 Melson Ridge Rd, Jamestown, KY 42629

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  803 Melson Ridge Rd, Jamestown, KY 42629

  Last Sold Summary

  • 3% Above List Price
  • $194/SF
  • 27 Days On Market

  Last Sold Price $186,000

  Last Listing Agent Gina Hill Keller Williams Bluegrass Realty - Lake Cumberland
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  /80

  $635,000

  • 5 Beds
  • 4 Baths
  • 3,324 Sq Ft

  893 Lilly Creek Ln, Jamestown, KY 42629

  Experience luxury lake living at its finest in this beautifully furnished, upscale lake house on stunning Lake Cumberland in South Central KY. Situated just across the lane from the shoreline, this home offers a serene lake setting combined with high-end comfort and style. Thoughtfully furnished with quality décor, this retreat is completely turnkey... ready for relaxing weekends, memorable

  Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

  893 Lilly Creek Ln, Jamestown, KY 42629
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  /68

  $270,000 Sold Sep 19, 2025

  216 Tall Timbers Dr, Jamestown, KY 42629

  • 3 Beds
  • 2.5 Baths
  • 1,659 Sq Ft
  • Built 1996

  Last Sold Summary

  • 23% Below List Price
  • $163/SF
  • 58 Days On Market

  Current Estimated Value $283,714

  Last Listing Agent Debbie Loy Wilson Lake Cumberland Properties, Ltd. Co.

  216 Tall Timbers Dr, Jamestown, KY 42629
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  /92

  Est $643,985 Not Listed For Sale

  230 Five Points Dr, Russell Springs, KY 42642

  • 5 Beds
  • 4.5 Baths
  • 4,565 Sq Ft
  • Built 2007

  230 Five Points Dr, Russell Springs, KY 42642

  Last Sold Summary

  • 8% Below List Price
  • $153/SF
  • 20 Days On Market

  Last Sold Price $699,000

  Last Listing Agent Kaye Hudson CENTURY 21 Advantage Realty
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  /70

  $329,000

  • 5 Beds
  • 2 Baths
  • 2,340 Sq Ft

  65 Wooldridge Rd, Jamestown, KY 42629

  Discover this absolute stunning 5-bedroom, 2-bath home, offering endless possibilities as a short-term rental or primary residence. Located just 5 miles from the breathtaking Lake Cumberland and conveniently close to town, this spacious 2,500 sq ft property blends original charm with modern upgrades. The owners mastered the task of transforming a vintage structure (formerly a church) into a

  Jill Johnson Eagle Realty & Development LLC

  65 Wooldridge Rd, Jamestown, KY 42629
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  /31

  $130,000 Sold Sep 30, 2025

  289 E Cumberland Ave, Jamestown, KY 42629

  • 4 Beds
  • 1 Bath
  • 1,428 Sq Ft

  Last Sold Summary

  • 23% Below List Price
  • $91/SF
  • 89 Days On Market

  Current Estimated Value $142,444

  Last Listing Agent Debbie Loy Wilson Lake Cumberland Properties, Ltd. Co.

  289 E Cumberland Ave, Jamestown, KY 42629
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  /13

  Not Listed For Sale

  90 Deer Trail Cir, Jamestown, KY 42629

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • Built 2022

  90 Deer Trail Cir, Jamestown, KY 42629

  Last Sold Summary

  • $116/SF
  • 0 Days On Market

  Last Sold Price $139,000

  Last Listing Agent Darren Gossage Weichert Realtors Ford Brothers, Inc.
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  /35

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  66 Deer Run Ln, Jamestown, KY 42629

  Well-maintained single-story ranch home, located 2.6 miles from Safe Harbour Jametown marina on beautiful Lake Cumberland. 3 bedrooms, 2 full baths, full laundry hookups. Open concept, great room, dining room and kitchen makes this home feel much bigger than the square footage with indicate. All bedrooms have large closets, the primary bedroom has an on-suite bath complete with a custom tiled

  Aaron Schork Champion Properties

  66 Deer Run Ln, Jamestown, KY 42629
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  /7

  $12,666 Sold Oct 20, 2025

  1 Cherry Loop, Jamestown, KY 42629

  • Land
  • 0.48 Acre
  • $26,388 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 123 Days On Market

  Last Listing Agent Troy Coffey Golden Rule - Wilson Real Estate & Auction #2 LLC

  1 Cherry Loop, Jamestown, KY 42629
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  /64

  Est $236,757 Not Listed For Sale

  2326 Kentucky 55, Jamestown, KY 42629

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1986

  2326 Kentucky 55, Jamestown, KY 42629

  Last Sold Summary

  • 1% Below List Price
  • $150/SF
  • 11 Days On Market

  Last Sold Price $239,500

  Last Listing Agent Kimberly Byrom Lake Cumberland Properties, Ltd. Co.
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  /99

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  169 Onyx Ridge Rd, Jamestown, KY 42629

  Discover this stunning 3-bedroom, 2-bath luxury cabin, perfectly situated just 5 minutes from Halcomb's Landing and Wolf Creek Dam—one of the best launch ramps on Lake Cumberland. Thoughtfully designed to sleep up to 8 guests, this fully furnished retreat features high-end finishes and professional décor throughout. Relax in style with two outdoor soaking tubs offering breathtaking views or

  Shelly Stoyell PCS Real Estate

  169 Onyx Ridge Rd, Jamestown, KY 42629
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  /62

  $200,000 Sold Jul 11, 2025

  265 E Cumberland Ave, Jamestown, KY 42629

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1996

  Last Sold Summary

  • 13% Below List Price
  • $137/SF
  • 16 Days On Market

  Last Listing Agent Debbie Loy Wilson Lake Cumberland Properties, Ltd. Co.

  265 E Cumberland Ave, Jamestown, KY 42629
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  /30

  Not Listed For Sale

  Lot 45 Pine View Cir, Jamestown, KY 42629

  Lot 45 Pine View Cir, Jamestown, KY 42629

  Last Sold Summary

  • 3 Days On Market

  Last Sold Price $35,000

  Last Listing Agent Shelly Stoyell PCS Real Estate
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  /63

  $399,000

  • 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

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