Underwood Group
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
  • About
    1. My Team
    2. About Us
    3. Contact Us
    4. Reviews
  • Market Snapshot
  • Register
  • /
  • Sign In
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
    Beds Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
    Baths Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
  • List
  • Mixed
  • Map
City: Winchester, KY
Price Reduced
Map
26 Properties Available In Winchester

26 Properties Available In Winchester

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
KY >Winchester >
Market Insights
Image
Address
Price
Beds
Baths
Area
Status
MLS®
187 Hawthorne Drive, Winchester, KY 40391

187 Hawthorne Drive, Winchester, KY 40391

Listed by Keller Williams Commonwealth

$415,000

3
2
2,027 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
107 Hibiscus Lane, Winchester, KY 40391

107 Hibiscus Lane, Winchester, KY 40391

Listed by Keller Williams Commonwealth

$369,900

4
3
1,978 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
214 Center Drive, Winchester, KY 40391

214 Center Drive, Winchester, KY 40391

Listed by The Brokerage

$197,000

3
1
1,193 SqFt
Pending
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
520 College Street, Winchester, KY 40391

520 College Street, Winchester, KY 40391

Listed by McCallie Real Estate

$192,400

3
1
1,272 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
444 Wellington Way, Winchester, KY 40391

444 Wellington Way, Winchester, KY 40391

Listed by The Agency

$309,900

4
3
1,963 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
213 E Broadway Street, Winchester, KY 40391

213 E Broadway Street, Winchester, KY 40391

Listed by GSP Homes

$199,000

3
1
1,453 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
107 S Burns Avenue, Winchester, KY 40391

107 S Burns Avenue, Winchester, KY 40391

Listed by Christies International Real Estate Bluegrass

$359,900

4
2
2,352 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
600 College Street, Winchester, KY 40391

600 College Street, Winchester, KY 40391

Listed by The Brokerage

$215,000

3
2
1,737 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
1039 Cole Road, Winchester, KY 40391

1039 Cole Road, Winchester, KY 40391

Listed by RE/MAX Elite Realty

$895,000

4
3
30.42 Acres
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
6 French Avenue, Winchester, KY 40391

6 French Avenue, Winchester, KY 40391

Listed by Woods Realty Group

$296,000

4
2
1,953 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
209 E Washington Street, Winchester, KY 40391

209 E Washington Street, Winchester, KY 40391

Listed by RE/MAX Creative, Winchester

$159,000

3
1
1,249 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
119 Tower Lane, Winchester, KY 40391

119 Tower Lane, Winchester, KY 40391

Listed by Wever Realty LLC

$220,000

3
1
1,272 SqFt
Pending
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
16 Denny Avenue, Winchester, KY 40391

16 Denny Avenue, Winchester, KY 40391

Listed by HomeFirst Real Estate

$58,500

3
1
1,152 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
1780 Stoner-Ephesus Road, Winchester, KY 40391

1780 Stoner-Ephesus Road, Winchester, KY 40391

Listed by Dream Maker Realty, LLC

$488,000

4
3
2,496 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
11 Stoney Brook Drive #1, Winchester, KY 40391

11 Stoney Brook Drive #1, Winchester, KY 40391

Listed by Milton and Associates Real Estate

$349,000

3
2
1,990 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
322 Calmes Boulevard, Winchester, KY 40391

322 Calmes Boulevard, Winchester, KY 40391

Listed by Dream Maker Realty, LLC

$379,000

3
3
2,204 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
528 Estes Drive, Winchester, KY 40391

528 Estes Drive, Winchester, KY 40391

Listed by Freedom Realty & Property Management

$219,900

3
2
1,904 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
65 Fitch Avenue, Winchester, KY 40391

65 Fitch Avenue, Winchester, KY 40391

Listed by Ensor Real Estate, LLC

$139,900

3
2
1,680 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
309 Gallahadion Court, Winchester, KY 40391

309 Gallahadion Court, Winchester, KY 40391

Listed by RE/MAX Creative, Winchester

$349,000

3
3
1,945 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
209 Boone Avenue, Winchester, KY 40391

209 Boone Avenue, Winchester, KY 40391

Listed by Lois Ann Disponett Real Est

$255,000

3
3
2,260 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
38 N Burns Avenue, Winchester, KY 40391

38 N Burns Avenue, Winchester, KY 40391

Listed by RE/MAX Creative Realty

$299,000

4
3
2,310 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
4664 Lexington Road, Winchester, KY 40391

4664 Lexington Road, Winchester, KY 40391

Listed by Block + Lot Homes

$2,500,000

8
8
13,433 SqFt
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
1320 Fulton Road, Winchester, KY 40391

1320 Fulton Road, Winchester, KY 40391

Listed by KY Realty Co

$435,000

--
--
0.22 Acres
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
345 Providence Lane, Winchester, KY 40391

345 Providence Lane, Winchester, KY 40391

Listed by Keller Williams Legacy Group

$875,000

--
--
120 Acres
Active
Imagine MLS / Bluegrass Association of REALTORS (LBAR)
  • 1
  • 2

explore listings in Winchester

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
site logo
  • Home
  • About
    1. My Team
    2. About Us
    3. Contact Us
    4. Reviews
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Market Snapshot
  • Sell
    1. Sell My Home
    2. Home Valuation
Underwood Group
Terra Long Underwood

+1(859) 707-7366 tlongrealestate@gmail.com

1908 Bryant Rd STE 250, Lexington, Kentucky 40509, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
site logo
  • Home
  • About
    1. My Team
    2. About Us
    3. Contact Us
    4. Reviews
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Market Snapshot
  • Sell
    1. Sell My Home
    2. Home Valuation
Underwood Group
Terra Long Underwood

+1(859) 707-7366 tlongrealestate@gmail.com

1908 Bryant Rd STE 250, Lexington, Kentucky 40509, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.