Prestonsburg, KY Homes

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  /6

  $23,000 Sold Feb 07, 2026

  0 Shop Branch Right Fork Bull Creek Unit 127089, Prestonsburg, KY 41653

  • Land
  • 13 Acres
  • $1,769 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 12 Days On Market

  Last Listing Agent Priscella Amburgey Re/Max Legacy Group-Paintsville

  0 Shop Branch Right Fork Bull Creek Unit 127089, Prestonsburg, KY 41653
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  /33

  Est $409,952 Not Listed For Sale

  15 S Circle Dr, Prestonsburg, KY 41653

  • 2 Beds
  • 2 Baths
  • 3,043 Sq Ft
  • Built 1990

  15 S Circle Dr, Prestonsburg, KY 41653

  Last Sold Summary

  • 6% Above List Price
  • $127/SF
  • 298 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Olivia Davis RE/MAX
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  /17

  $140,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft

  8107 State Road Fork, Prestonsburg, KY 41653

  Nestled in a quiet, rural setting, this property features a 3 bedroom, 1 bath home with a little over 1,000 sq. ft. of living space, ready for your personal touch or vision and 67 +/- acres. This is a rare opportunity to own a sizable tract of land with a home already in place. **Property lines and acreage to be determined by purchaser**

  Rachael Nicole Johnson Century 21 American Way Realty

  8107 State Road Fork, Prestonsburg, KY 41653
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  /23

  $155,000 Sold Apr 11, 2025

  70 N Roberts Dr, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $127/SF
  • 9 Days On Market

  Current Estimated Value $163,829

  Last Listing Agent Carolyn Hager RE/MAX Elite Realty

  70 N Roberts Dr, Prestonsburg, KY 41653
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  /7

  Est $106,989 Not Listed For Sale

  1125 S Highland Ave, Prestonsburg, KY 41653

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • Built 1961

  1125 S Highland Ave, Prestonsburg, KY 41653

  Last Sold Summary

  • 19% Above List Price
  • $87/SF
  • 12 Days On Market

  Last Sold Price $90,000

  Last Listing Agent Ashley Carroll EAST KENTUCKY REALTY
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  /20

  $55,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  47 New Castle Ln, Prestonsburg, KY 41653

  Charming 3-bedroom, 2-bath single-wide home conveniently located in Prestonsburg, just minutes from downtown! This property offers both comfort and accessibility, featuring a handicap ramp for easy entry and covered front and back porches—perfect for relaxing or entertaining. Situated on a 0.31-acre lot, the home includes a fully fenced front yard, ideal for pets or outdoor enjoyment. A detached

  Joe D. Marson Re/Max Legacy Group

  47 New Castle Ln, Prestonsburg, KY 41653
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  /2

  $770,000 Sold Jan 08, 2026

  00 Three Story Caves Subdivision Lots 1-14, Prestonsburg, KY 41653

  • Land
  • 9.21 Acres
  • $83,605 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Rachael Nicole Johnson Century 21 American Way Realty

  00 Three Story Caves Subdivision Lots 1-14, Prestonsburg, KY 41653
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  /39

  Est $160,905 Not Listed For Sale

  516 Riverside Dr, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • Built 1950

  516 Riverside Dr, Prestonsburg, KY 41653

  Last Sold Summary

  • 12% Above List Price
  • $88/SF
  • 2 Days On Market

  Last Sold Price $144,300

  Last Listing Agent Blake Liles The Agency
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  /22

  $129,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  152 S Roberts Dr, Prestonsburg, KY 41653

  Say hello to your new home! Look at this Beautiful 3-bed, 2-bath home with over 1,500 sq ft of comfortable living space. Brand new Metal roof. This home Features a spacious covered front porch perfect for relaxing or entertaining. The large fenced yard offers privacy, a huge shade tree and plenty of room for outdoor activities, while the carport and concrete driveway provide convenient parking.

  Mary Wright RE/MAX Freedom

  152 S Roberts Dr, Prestonsburg, KY 41653
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  /3

  $315,000 Sold Jan 20, 2026

  00 Ridgewood Dr Lots #R19 20 22-26, Prestonsburg, KY 41653

  • Land
  • 2.8 Acres
  • $112,500 per Acre

  Last Sold Summary

  Last Listing Agent Rachael Nicole Johnson Century 21 American Way Realty

  00 Ridgewood Dr Lots #R19 20 22-26, Prestonsburg, KY 41653
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  /23

  Est $170,391 Not Listed For Sale

  318 E Graham St, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 1930

  318 E Graham St, Prestonsburg, KY 41653

  Last Sold Summary

  • 10% Above List Price
  • $78/SF
  • 1 Day On Market

  Last Sold Price $155,000

  Last Listing Agent Carolyn Hager RE/MAX
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  /2

  $85,000

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  17 Music St, Prestonsburg, KY 41653

  Welcome to 17 Music Street in Prestonsburg, KY - a wonderful opportunity to own a home in a convenient and established location. Whether you're a first-time buyer, downsizing, or looking to invest, this property offers comfort, functionality, and small-town charm. Inside, you'll find a welcoming layout designed for everyday living. The living spaces provide a comfortable setting for relaxing or

  Hunter Miller GSP Homes

  17 Music St, Prestonsburg, KY 41653
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  /45

  $365,000 Sold Oct 28, 2025

  60 Bevins St, Prestonsburg, KY 41653

  • 3 Beds
  • 2.5 Baths
  • 2,448 Sq Ft
  • Built 2014

  Last Sold Summary

  • 2% Above List Price
  • $149/SF
  • 14 Days On Market

  Current Estimated Value $116,931

  Last Listing Agent Mary Wright Re/Max Freedom

  60 Bevins St, Prestonsburg, KY 41653
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  /9

  Est $130,900 Not Listed For Sale

  195 W Graham St, Prestonsburg, KY 41653

  • 2 Beds
  • 1 Bath
  • 1,180 Sq Ft
  • Built 1965

  195 W Graham St, Prestonsburg, KY 41653

  Last Sold Summary

  • 25% Above List Price
  • $89/SF
  • 22 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Stephanie Wallace Century 21 American Way Realty
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  /53

  $167,000

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1320 Riverside Dr, Prestonsburg, KY 41653

  Super excited to announce this gem! A completely remodeled 3 bed, 2 bath home, move-in ready! Enjoy a polished interior, with all new flooring and paint. A beautiful gas Fireplace in the Livingroom for cozy nights at home. An attached 1-car garage, and an absolutely great location right in town. Modern finishes, open layout, and move-in ease—everything you want, all in one perfect package. Don't

  Mary Wright Re/Max Freedom

  1320 Riverside Dr, Prestonsburg, KY 41653
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  /33

  $250,000 Sold Jan 23, 2026

  2911 Ky Rt 1428, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 2,268 Sq Ft
  • Built 1992

  Last Sold Summary

  • 22% Below List Price
  • $110/SF
  • 147 Days On Market

  Last Listing Agent Ellen Harris Century 21 American Way Realty

  2911 Ky Rt 1428, Prestonsburg, KY 41653
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  /63

  Est $316,040 Not Listed For Sale

  508 Trimble Branch, Prestonsburg, KY 41653

  • 5 Beds
  • 3 Baths
  • 2,793 Sq Ft
  • Built 1961

  508 Trimble Branch, Prestonsburg, KY 41653

  Last Sold Summary

  • 1% Below List Price
  • $114/SF
  • 35 Days On Market

  Last Sold Price $318,000

  Last Listing Agent Leslie Terry Century 21 American Way Realty
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  /4

  $48,000

  • Land
  • 0.35 Acre
  • $137,143 per Acre

  C35 Crestwood Dr, Prestonsburg, KY 41653

  Residential Lot for Sale-Crestwood Subdivision, Don't miss this rare opportunity to own a 0.35 acre residential lot in the highly sought - after Crestwood Subdivision! Nestled next to the golf course and offering breathtaking scenic mountaintop views, this property is the perfect canvas to build your dream home. Enjoy the serenity of a quiet neighborhood while being just minutes from downtown

  Joe D. Marson Re/Max Legacy Group

  C35 Crestwood Dr, Prestonsburg, KY 41653
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  /30

  $121,500 Sold Dec 15, 2025

  961 S Highland Ave, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • Built 1956

  Last Sold Summary

  • 7% Below List Price
  • $72/SF
  • 49 Days On Market

  Current Estimated Value $119,427

  Last Listing Agent Mary Wright Re/Max Freedom

  961 S Highland Ave, Prestonsburg, KY 41653
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  /10

  Est $96,135 Not Listed For Sale

  222 S Highland Ave, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • Built 1940

  222 S Highland Ave, Prestonsburg, KY 41653

  Last Sold Summary

  • 32% Above List Price
  • $59/SF
  • 115 Days On Market

  Last Sold Price $73,000

  Last Listing Agent Karen Stone Century 21 American Way Realty
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  /14

  $29,950 Pending

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  121 Cr-1058, Prestonsburg, KY 41653

  One story home with carport and garage!!! The cute home located in Prestonsburg is ready to be loved and could be YOURS!!!! Call to schedule your showing TODAY!!!

  Jason Szaks EXIT TOWN & COUNTRY REALTORS

  121 Cr-1058, Prestonsburg, KY 41653
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  /25

  $99,000 Sold Dec 11, 2025

  00 Pruitt St, Prestonsburg, KY 41653

  • Land
  • 75 Acres
  • $1,320 per Acre

  Last Sold Summary

  • 34% Below List Price
  • 157 Days On Market

  Last Listing Agent Lana Mulkey Re/Max Legacy Group

  00 Pruitt St, Prestonsburg, KY 41653
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  /14

  Est $197,309 Not Listed For Sale

  177 E Dingus St, Prestonsburg, KY 41653

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1920

  177 E Dingus St, Prestonsburg, KY 41653

  Last Sold Summary

  • 19% Above List Price
  • $95/SF
  • 2 Days On Market

  Last Sold Price $166,000

  Last Listing Agent Ellen Harris Century 21 American Way Realty
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  /29

  $99,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  66 Haywood Ln, Prestonsburg, KY 41653

  Beautifully maintained 2 bedrooms, 2 baths, double wide just off US 23, inside Prestonsburg city limits. It is conveniently located to the Pikeville area. Concrete driveway, 2 car portable carport, front covered porch, walk-in closet, and rear stoop,

  Brenda Gooslin AAA Real Estate Services

  66 Haywood Ln, Prestonsburg, KY 41653
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  /33

  $132,000 Sold Jun 03, 2025

  106 Waddle Ln, Prestonsburg, KY 41653

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1992

  Last Sold Summary

  • 9% Below List Price
  • $79/SF
  • 149 Days On Market

  Last Listing Agent Jessica Holcomb Blu Horizon Real Estate

  106 Waddle Ln, Prestonsburg, KY 41653
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  /13

  Est $388,646 Not Listed For Sale

  246 N Arnold Ave, Prestonsburg, KY 41653

  • 3 Beds
  • 1.5 Baths
  • 3,024 Sq Ft
  • Built 1937

  246 N Arnold Ave, Prestonsburg, KY 41653

  Last Sold Summary

  • 5% Below List Price
  • $135/SF
  • 51 Days On Market

  Last Sold Price $409,000

  Last Listing Agent Ellen Harris Century 21 American Way Realty
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  /4

  $69,000

  • Land
  • 0.45 Acre
  • $153,333 per Acre

  76 C Crestwood Dr, Prestonsburg, KY 41653

  Lot 76 C located in beautiful views of Stonecrest Golf Course. 19,653 sq ft .45 acres.

  Amy Michelle Watkins Re/Max Freedom

  76 C Crestwood Dr, Prestonsburg, KY 41653
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  /45

  $185,000 Sold Mar 09, 2026

  366 N Highland Ave, Prestonsburg, KY 41653

  • 6 Beds
  • 4 Baths
  • 2,600 Sq Ft
  • Built 1950

  Last Sold Summary

  • 26% Below List Price
  • $71/SF
  • 286 Days On Market

  Current Estimated Value $303,744

  Last Listing Agent Cliff Bennett Better Homes & Gardens Real Estate-Redd, Brown & Williams

  366 N Highland Ave, Prestonsburg, KY 41653
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  /44

  Est $273,280 Not Listed For Sale

  752 N Arnold Ave, Prestonsburg, KY 41653

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1960

  752 N Arnold Ave, Prestonsburg, KY 41653

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 46 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Ellen Harris Century 21 American Way Realty
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  /4

  $62,000 Pending

  • Land
  • 6 Acres
  • $10,333 per Acre

  160 Fannin Ln, Prestonsburg, KY 41653

  Ready to build a home!! This 6 Acres of private land is located at the end of the blacktop road.

  Stephanie Wallace Century 21 American Way Realty

  160 Fannin Ln, Prestonsburg, KY 41653
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  /23

  $335,000 Sold Oct 14, 2025

  1000 Mays Branch, Prestonsburg, KY 41653

  • 3 Beds
  • 3 Baths
  • 2,513 Sq Ft
  • Built 1977

  Last Sold Summary

  • $133/SF
  • 4 Days On Market

  Current Estimated Value $332,266

  Last Listing Agent Joe D. Marson Re/Max Legacy Group

  1000 Mays Branch, Prestonsburg, KY 41653
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  /13

  Est $345,633 Not Listed For Sale

  414 Mays Branch, Prestonsburg, KY 41653

  • 4 Beds
  • 3 Baths
  • 3,155 Sq Ft
  • Built 1980

  414 Mays Branch, Prestonsburg, KY 41653

  Last Sold Summary

  • 3% Below List Price
  • $113/SF
  • 1 Day On Market

  Last Sold Price $355,000

  Last Listing Agent Stephanie Wallace Century 21 American Way Realty
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  /25

  $300,000

  • Land
  • 32 Acres
  • $9,375 per Acre

  2209 Kentucky Route 3385, Prestonsburg, KY 41653

  Looking to get away from it all? This property has it all--multiple riding trails, a pond, a gas well that provides free gas for one residence, building sites, two (2) mobile home hookup sites, and endless hunting potential! If you're looking for an investment opportunity, this is it! Perfect location for cabins, campsites, or a campground! The property on the right side of Ky 3885 is in

  Rita Fitch Realty One USA, INC

  2209 Kentucky Route 3385, Prestonsburg, KY 41653
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  /2

  $170,000 Sold Sep 30, 2025

  21 Bingham St Unit 2, Prestonsburg, KY 41653

  • 6 Beds
  • 4 Baths
  • 2,464 Sq Ft
  • Built 1994

  Last Sold Summary

  • $69/SF
  • 0 Days On Market

  Last Listing Agent Teresa Preston Better Homes & Gardens Real Estate-Redd, Brown & Williams

  21 Bingham St Unit 2, Prestonsburg, KY 41653
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  /24

  Est $409,374 Not Listed For Sale

  1140 Crestwood Dr, Prestonsburg, KY 41653

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2005

  1140 Crestwood Dr, Prestonsburg, KY 41653

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 88 Days On Market

  Last Sold Price $424,000

  Last Listing Agent Stephanie Wallace Century 21 American Way Realty
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  /15

  $125,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  9 S Stanley Ave, Prestonsburg, KY 41653

  Beautiful 3-bed, 2-bath home with over 1,500 sq ft of comfortable living space. This home Features a spacious covered front porch perfect for relaxing or entertaining. This inviting home combines comfort, functionality, and outdoor space — a perfect place to call home! Recently renovated , complete with all-new plumbing and full bathroom remodel. Strategically situated in Prestonsburg, this

  Joshua M. Blevins Re/Max Freedom

  9 S Stanley Ave, Prestonsburg, KY 41653
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  /2

  $111,000 Sold Jul 17, 2025

  145 Sycamore Hollow Rd, Prestonsburg, KY 41653

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1980

  Last Sold Summary

  • 11% Below List Price
  • $105/SF
  • 61 Days On Market

  Last Listing Agent S Lynn Keyland Plum Tree Realty

  145 Sycamore Hollow Rd, Prestonsburg, KY 41653
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  /58

  Est $318,263 Not Listed For Sale

  100 Lawson St, Prestonsburg, KY 41653

  • 4 Beds
  • 3 Baths
  • 2,802 Sq Ft
  • Built 1976

  100 Lawson St, Prestonsburg, KY 41653

  Last Sold Summary

  • 6% Above List Price
  • $107/SF
  • 65 Days On Market

  Last Sold Price $299,000

  Last Listing Agent Janice Kidd RE/MAX
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  /11

  $335,000

  • 4 Beds
  • 4 Baths
  • 2,184 Sq Ft

  5050 Ky Route 114, Prestonsburg, KY 41653

  Rare opportunity to own a versatile quad-plex situated on approximately 11 acres with significant upside potential. Property features four residential rental units, plus additional unoccupied square footage on the lower level equal to the current residential footprint, offering excellent potential for conversion into additional rental units or use as office, retail, or service-based business

  Joe D. Marson Re/Max Legacy Group

  5050 Ky Route 114, Prestonsburg, KY 41653
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  /36

  $374,000 Sold Dec 09, 2025

  725 Mays Branch Rd, Prestonsburg, KY 41653

  • 3 Beds
  • 3.5 Baths
  • 2,331 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $160/SF
  • 75 Days On Market

  Last Listing Agent Ellen Harris Century 21 American Way Realty

  725 Mays Branch Rd, Prestonsburg, KY 41653

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