Winchester, KY Homes

• 

  

  

  /31

  Est $243,405

  Not Listed For Sale

  121 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 2002

  121 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 70 Days On Market
• 

  

  /2

  $490,000

  $60K PRICE DROP

  • Land
  • 1.53 Acres
  • $320,261 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
• 

  

  

  /44

  $315,000

  Sold Jun 27, 2025

  43 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,459 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 70 Days On Market

  Current Estimated Value $357,052

  Last Listing Agent Chad Bowman The Brokerage

  43 Skylark Dr, Winchester, KY 40391
• 

  

  

  /23

  Est $281,309

  Not Listed For Sale

  302 Salem Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 2001

  302 Salem Ave, Winchester, KY 40391

  Last Sold Summary

  • 34 Days On Market
• 

  

  /2

  $150,000

  • Land
  • 2.16 Acres
  • $69,444 per Acre

  120 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  120 Knox Ct, Winchester, KY 40391
• 

  

  /28

  $265,000

  Sold Jul 02, 2025

  609 Clintonville Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,305 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $275,210

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  609 Clintonville Rd, Winchester, KY 40391
• 

  

  /17

  Est $290,496

  Not Listed For Sale

  218 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 2005

  218 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market
• 

  

  /63

  $1,149,000

  $30K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
• 

  

  /12

  $9,000

  Sold Sep 18, 2025

  406 W Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,428 Sq Ft
  • Built 1945

  Last Sold Summary

  • 10% Below List Price
  • $6/SF
  • 19 Days On Market

  Current Estimated Value $129,193

  Last Listing Agent Jack Rookard Rookard Real Estate Consultants

  406 W Washington St, Winchester, KY 40391
• 

  

  /20

  Est $255,729

  Not Listed For Sale

  208 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 2002

  208 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /37

  $233,000

  • 3 Beds
  • 2 Baths
  • 1,261 Sq Ft

  14 Cook Ave, Winchester, KY 40391

  Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a

  Janna Chalfant Smith United Real Estate Bluegrass

  14 Cook Ave, Winchester, KY 40391
• 

  

  /26

  $175,000

  Sold Apr 22, 2026

  10 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1988

  Last Sold Summary

  • $189/SF
  • 7 Days On Market

  Current Estimated Value $176,648

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  10 Pocahontas Trail, Winchester, KY 40391
• 

  

  /32

  Est $261,361

  Not Listed For Sale

  200 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2002

  200 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  

  /39

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  13 Lakeview Dr, Winchester, KY 40391

  Seller has accepted an offer with a 48 hour kickout clause. Beautifully updated brick ranch with a partially finished basement offering 3 bedrooms and 2 full baths! The main level features a welcoming living room with a masonry gas log fireplace that opens into the updated kitchen complete with island bar seating, eat-in dining area, and access to the screened-in deck, perfect for relaxing or

  Michelle Blackburn RE/MAX Creative, Winchester

  13 Lakeview Dr, Winchester, KY 40391
• 

  

  /79

  $425,000

  Sold Feb 23, 2026

  1410 Dry Fork Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  Last Sold Summary

  • 15% Below List Price
  • $399/SF
  • 78 Days On Market

  Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
• 

  

  /37

  Est $317,538

  Not Listed For Sale

  311 Fern Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1999

  311 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  169 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  169 Duclair Dr, Winchester, KY 40391
• 

  

  /24

  $188,000

  Sold Jan 29, 2026

  27 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $114/SF
  • 112 Days On Market

  Current Estimated Value $195,491

  Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
• 

  

  /49

  Est $313,514

  Not Listed For Sale

  317 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1999

  317 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /11

  $143,000

  $12K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  19 3rd St, Winchester, KY 40391

  3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square

  Anthony Gigilo ListWithFreedom.com

  19 3rd St, Winchester, KY 40391
• 

  

  /26

  $165,000

  Sold Apr 23, 2026

  52 Judy Ann Ct, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1981

  Last Sold Summary

  • $126/SF
  • 0 Days On Market

  Current Estimated Value $168,983

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  52 Judy Ann Ct, Winchester, KY 40391
• 

  

  /75

  Est $300,254

  Not Listed For Sale

  314 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1999

  314 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market
• 

  

  /42

  $349,500

  Pending

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

  221 W Hickman St, Winchester, KY 40391

  Step inside this beautifully remodeled historic home and you'll immediately understand why homes like this are so special. With loads of space, four bedrooms, and three full bathrooms, this home offers the character buyers love with the modern updates they need. Every detail has been thoughtfully refreshed while preserving the charm and warmth that make historic homes so hard to duplicate. From

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /25

  $375,000

  Sold Aug 29, 2025

  317 Hanover Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $121/SF
  • 8 Days On Market

  Current Estimated Value $383,893

  Last Listing Agent Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
• 

  

  /35

  Est $265,184

  Not Listed For Sale

  206 Moss Cir, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft
  • Built 1997

  206 Moss Cir, Winchester, KY 40391

  Last Sold Summary

  • 20 Days On Market
• 

  

  /20

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  122 Spruce Ct, Winchester, KY 40391

  Don't miss this move-in ready brick ranch home offering the perfect blend of comfort, style and convenience. Whether you're relaxing indoors or enjoying the outdoor space, this home is ready for its next owner to move right in and start making memories. Conveniently located near shopping, dining, schools, and major roadways, this updated ranch is a must-see. Don't miss your opportunity to own

  Peggy Baldridge HomeFirst Real Estate

  122 Spruce Ct, Winchester, KY 40391
• 

  

  /60

  $545,000

  Sold Oct 31, 2025

  445 Lynnway Dr, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft
  • Built 1993

  Last Sold Summary

  • $149/SF
  • 4 Days On Market

  Current Estimated Value $539,095

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
• 

  

  /35

  Est $293,928

  Not Listed For Sale

  1896 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,942 Sq Ft
  • Built 1960

  1896 Mount Sterling Rd, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market
• 

  

  /42

  $350,000

  $10K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,798 Sq Ft

  502 W Lexington Ave, Winchester, KY 40391

  Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units!

  Jason Townsend Kentucky Residential Real Estate, LLC

  502 W Lexington Ave, Winchester, KY 40391
• 

  

  /27

  $263,500

  Sold Apr 10, 2026

  222 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 121 Days On Market

  Current Estimated Value $265,930

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, Winchester, KY 40391
• 

  

  /35

  Est $412,025

  Not Listed For Sale

  2195 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft
  • Built 2000

  2195 Pretty Run Rd, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market
• 

  

  /34

  $349,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  405 Tremont Ln, Winchester, KY 40391

  Welcome to this beautifully maintained 4 bedroom, 2.5 bathroom home over 2,200 square feet of comfortable living space. Built in 2005, this two story home features a functional layout with the primary suite and laundry conveniently located on the main level. Step into fresh paint, undated vinyl flooring and a spacious living area complete with a cozy fireplace perfect for entertaining or

  Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, Winchester, KY 40391
• 

  

  /27

  $380,000

  Sold Nov 10, 2025

  5705 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $128/SF
  • 50 Days On Market

  Current Estimated Value $391,246

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /38

  Est $357,211

  Not Listed For Sale

  3635 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1920

  3635 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market
• 

  

  /59

  $274,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  403 Pueblo Ct, Winchester, KY 40391

  Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes

  Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, Winchester, KY 40391
• 

  

  /102

  $525,000

  Sold Dec 22, 2025

  1953 Cabin Creek Rd, Winchester, KY 40391

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $137/SF
  • 9 Days On Market

  Current Estimated Value $540,971

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /105

  Est $778,748

  Not Listed For Sale

  1039 Cole Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft
  • Built 1977

  1039 Cole Rd, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market
• 

  

  /19

  $250,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,445 Sq Ft

  130 E Broadway St, Winchester, KY 40391

  Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income

  Sarah May Mayca Property Solutions

  130 E Broadway St, Winchester, KY 40391
• 

  

  /114

  $635,000

  Sold Sep 30, 2025

  315 The Woods Ln, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $115/SF
  • 63 Days On Market

  Current Estimated Value $614,003

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
• 

  

  /44

  Est $382,194

  Not Listed For Sale

  207 Citation Ct, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,304 Sq Ft
  • Built 2005

  207 Citation Ct, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

Showing Results 401 - 440, Page 11 of 18