Winchester, KY Homes

• 

  

  

  /70

  Est $544,361 Not Listed For Sale

  519 Right Angle Rd, Winchester, KY 40391

  • 6 Beds
  • 3 Baths
  • 3,712 Sq Ft
  • Built 2000

  519 Right Angle Rd, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $143/SF
  • 186 Days On Market

  Last Sold Price $530,000

  Last Listing Agent The Prather Team - Michael Prather Keller Williams Bluegrass Realty
• 

  

  

  /28

  $298,900

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft

  24 N Burns Ave, Winchester, KY 40391

  Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

  Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  

  /25

  $223,000 Sold Nov 04, 2025

  204 Crawford Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 1 Day On Market

  Current Estimated Value $223,008

  Last Listing Agent Tisha Monte Bluegrass Properties Group

  204 Crawford Ct, Winchester, KY 40391
• 

  

  

  /69

  Est $368,739 Not Listed For Sale

  3975 Wills Rupard Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft
  • Built 1986

  3975 Wills Rupard Rd, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $108/SF
  • 218 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Tonya Morrow KY Local
• 

  

  

  /36

  $345,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  208 Citation Ct, Winchester, KY 40391

  One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. Great for downsizing or first time homeowner! The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under.

  Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
• 

  

  /29

  $227,500 Sold Sep 11, 2025

  301 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,220 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 0 Days On Market

  Current Estimated Value $225,733

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  301 Cabin Creek Heights, Winchester, KY 40391
• 

  

  /45

  Est $402,673 Not Listed For Sale

  1600 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,846 Sq Ft
  • Built 2012

  1600 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 34% Above List Price
  • $105/SF
  • 147 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Joyce Ratliff Tom Goebel & Company
• 

  

  /33

  $299,500

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

  211 Lindsey Ct, Winchester, KY 40391

  Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been

  Lesley Ward Biederman Real Estate

  211 Lindsey Ct, Winchester, KY 40391
• 

  /2

  $125,000 Sold May 23, 2025

  265 Duclair Dr, Winchester, KY 40391

  • Land
  • 1.01 Acres
  • $123,762 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  265 Duclair Dr, Winchester, KY 40391
• 

  

  /56

  Est $642,198 Not Listed For Sale

  9953 Ironworks Rd, Winchester, KY 40391

  • 6 Beds
  • 2.5 Baths
  • 3,800 Sq Ft
  • Built 2003

  9953 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Below List Price
  • $171/SF
  • 7 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Tara Smith Keller Williams Commonwealth
• 

  

  /45

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  120 Pilot View Rd, Winchester, KY 40391

  Charming 1930 farmhouse that perfectly blends timeless character with modern updates, situated on 5 beautiful acres. This fully remodeled home offers 3 bedrooms, 2.5 baths, and a spacious bonus room currently used as a home office. Inside, you'll find a formal dining room, updated living spaces, and a large laundry room where the washer and dryer convey. Major improvements include a new roof

  Jennifer Parsons RE/MAX Elite Lexington

  120 Pilot View Rd, Winchester, KY 40391
• 

  

  /41

  $279,900 Sold Aug 12, 2025

  225 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft
  • Built 2006

  Last Sold Summary

  • $155/SF
  • 8 Days On Market

  Current Estimated Value $285,906

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  225 Prescott Ln, Winchester, KY 40391
• 

  

  /17

  Est $492,552 Not Listed For Sale

  1026 Crowe Ridge Rd, Winchester, KY 40391

  • 1 Bath
  • Built 1945

  1026 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $407/SF
  • 56 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Sophia Herald Herald Real Estate
• 

  

  /70

  $335,000 Pending

  • 6 Beds
  • 4 Baths
  • 3,544 Sq Ft

  297 S Main St, Winchester, KY 40391

  Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

  Silvia Torres Tru Life Real Estate

  297 S Main St, Winchester, KY 40391
• 

  

  /49

  $442,500 Sold Apr 18, 2025

  321 Frontier Way, Winchester, KY 40391

  • 6 Beds
  • 3.5 Baths
  • 3,882 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $114/SF
  • 134 Days On Market

  Current Estimated Value $448,624

  Last Listing Agent Olivia White Deborah Ball Realty

  321 Frontier Way, Winchester, KY 40391
• 

  

  /26

  Est $325,763 Not Listed For Sale

  11705 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,668 Sq Ft
  • Built 1988

  11705 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 48% Above List Price
  • $82/SF
  • 81 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Matthew J. Reffett Re/Max Legacy Group - Paintsville
• 

  

  /38

  $359,900 New Construction

  • 4 Beds
  • 4.5 Baths

  3600 Crowe Ridge Rd, Winchester, KY 40391

  Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 20' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

  Maggie Napier Napier Realtors

  3600 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /24

  $185,000 Sold Jun 23, 2025

  605 Dixiana Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1990

  Last Sold Summary

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

  Current Estimated Value $193,900

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  605 Dixiana Dr, Winchester, KY 40391
• 

  

  /33

  Est $305,001 Not Listed For Sale

  510 Wills Rupard Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,592 Sq Ft
  • Built 1990

  510 Wills Rupard Rd, Winchester, KY 40391

  Last Sold Summary

  • 69% Above List Price
  • $114/SF
  • 2 Days On Market

  Last Sold Price $181,000

  Last Listing Agent Joe Marcum CENTURY 21 Advantage Realty
• 

  

  /34

  $325,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,776 Sq Ft

  213 Orchid Ct, Winchester, KY 40391

  Kasey McCarty 5.23 Real Estate

  213 Orchid Ct, Winchester, KY 40391
• 

  

  /39

  $340,000 Sold Oct 10, 2025

  219 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $116/SF
  • 48 Days On Market

  Current Estimated Value $342,213

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, Winchester, KY 40391
• 

  

  /33

  Est $270,726 Not Listed For Sale

  7344 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1925

  7344 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 24% Above List Price
  • $156/SF
  • 2 Days On Market

  Last Sold Price $219,000

  Last Listing Agent Jason Rainey Executive Real Estate, LLC
• 

  

  /50

  $359,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  175 Overlooking Dr, Winchester, KY 40391

  Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversized rear deck and enjoy the countryside views. This 3-bedroom, 2-bathroom home features Living Room, Dining Room, Family Room, has two cozy fireplaces for your entertainment. Home has a full partially finished basement with a large recreation room and plenty of space to add additional rooms if needed. To

  Keith Wilson Coldwell Banker McMahan

  175 Overlooking Dr, Winchester, KY 40391
• 

  

  /58

  $850,000 Sold Jun 27, 2025

  2158 Venable Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1988

  Last Sold Summary

  • $285/SF
  • 1 Day On Market

  Current Estimated Value $844,083

  Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

  2158 Venable Rd, Winchester, KY 40391
• 

  

  /82

  Est $353,966 Not Listed For Sale

  380 L E Junction Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,173 Sq Ft
  • Built 1976

  380 L E Junction Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $102/SF
  • 13 Days On Market

  Last Sold Price $324,000

  Last Listing Agent Davin Smith Caswell Prewitt Realty, Inc
• 

  

  /67

  $325,000

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /69

  $282,500 Sold Sep 30, 2025

  227 Cross Brook Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 9 Days On Market

  Current Estimated Value $283,032

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  227 Cross Brook Ln, Winchester, KY 40391
• 

  

  /51

  Est $476,392 Not Listed For Sale

  5600 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • Built 1992

  5600 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $162/SF
  • 62 Days On Market

  Last Sold Price $460,000

  Last Listing Agent Kymberly McCreary Keller Williams Commonwealth
• 

  

  /34

  $300,000

  • 2 Beds
  • 1 Bath
  • 1,531 Sq Ft

  1508 Ford Hampton Rd, Winchester, KY 40391

  Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

  Michelle Blackburn RE/MAX Creative, Winchester

  1508 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /75

  $289,900 Sold Aug 11, 2025

  126 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • Built 1992

  Last Sold Summary

  • $203/SF
  • 0 Days On Market

  Current Estimated Value $288,858

  Last Listing Agent Jennifer Guyton White Realty, LLC

  126 Ashley Dr, Winchester, KY 40391
• 

  

  /38

  Est $368,631 Not Listed For Sale

  3070 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,866 Sq Ft
  • Built 1998

  3070 Goshen Rd, Winchester, KY 40391

  Last Sold Summary

  • $128/SF
  • 2 Days On Market

  Last Sold Price $367,000

  Last Listing Agent Kevin Bradley Keller Williams Legacy Group
• 

  

  /51

  $775,000

  • 5 Beds
  • 3.5 Baths
  • 2,904 Sq Ft

  1783 Gay Evans Rd, Winchester, KY 40391

  Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

  Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
• 

  

  /58

  $345,000 Sold Nov 14, 2025

  205 Chardonnay Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 59 Days On Market

  Current Estimated Value $356,712

  Last Listing Agent Janna Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
• 

  

  /32

  Est $282,257 Not Listed For Sale

  810 Howard Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 2001

  810 Howard Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $210/SF
  • 17 Days On Market

  Last Sold Price $264,900

  Last Listing Agent Serena Cassidy Coldwell Banker McMahan
• 

  

  /30

  $215,000 Pending

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

  2721 Pretty Run Rd, Winchester, KY 40391

  Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
• 

  

  /27

  $210,000 Sold Sep 04, 2025

  305 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $215,899

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
• 

  

  /53

  Est $286,317 Not Listed For Sale

  1489 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,126 Sq Ft
  • Built 1995

  1489 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $244/SF
  • 45 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Sabina Chambers Semonin Realty
• 

  

  /100

  $1,789,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /44

  $320,000 Sold Nov 21, 2025

  104 Teakwood Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 24 Days On Market

  Current Estimated Value $319,295

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
• 

  

  /23

  Est $321,675 Not Listed For Sale

  440 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 2004

  440 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 31% Above List Price
  • $151/SF
  • 3 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Louis Baldwin Threshold Real Estate Services

Showing Results 81 - 120, Page 3 of 18