Downtown -- Winchester KY Real Estate

Included below are homes for sale in Downtown, a neighborhood in Winchester, KY. Downtown is located in the city of Winchester, in Montgomery County.  These Downtown real estate listings are updated daily from the Lexington KY MLS (LBAR).

Want more information about any of these Downtown homes for sale? Just click the "Request More Info" or "Schedule a Showing" button when viewing the details of that property.  As Winchester real estate experts, we not only have access to the property disclosures and past sales history of each property, but the local knowledge to help you interpret them. We can also provide you with dates and prices of nearby homes recently sold in Winchester, and more.

Also, please consider registering for a free account -- doing so will enable you to receive automatic email notifications when new homes come on the market in Downtown.

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$349,000
Bedrooms: 5
Baths: 4
Approx Sq Ft: 4419
418 Boone Avenue
Winchester, KY 40391
MLS #: 20002341
Subdivision: downtown
NEW PRICE! Historic home near Winchester Country Club with many improvements is waiting for you. The home offers lovely woodwork, stairway, sliding doors and...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Tom Goebel & Company
$249,000
Bedrooms: 5
Baths: 2
Approx Sq Ft: 3160
261 S Main Street (Pending)
Winchester, KY 40391
MLS #: 20012628
Subdivision: downtown
This is your opportunity to own a historical home (circa 1880 The J.W. Stapleton House). The sellers have painstakingly retained the unique original charm, but...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Bluegrass Sotheby's International Realty
$248,552
Bedrooms: 5
Baths: 3
Approx Sq Ft: 4033
7 French Avenue
Winchester, KY 40391
MLS #: 20007550
Subdivision: downtown
Stunning century old home with welcoming front porch! Warm hardwood floors guide you throughout well maintained home. Owners have modernized while preserving...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Re/Max Creative Realty
$244,900
Bedrooms: 3
Baths: 2
Approx Sq Ft: 2639
603 Boone Avenue
Winchester, KY 40391
MLS #: 20007135
Subdivision: downtown
Situated on coveted Boone Avenue with nearly an acre lot, and within easy walking distance to the Winchester Country Club and everything downtown Winchester...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Freedom Realty & Property Management
$200,000
Bedrooms: 4
Baths: 2
Approx Sq Ft: 2800
117 S Burns Avenue
Winchester, KY 40391
MLS #: 20013265
Subdivision: downtown
Beautiful red brick bungalow that has it all! This home has been well kept and offers a lot of interior space along with an amazing outdoor area as well. It...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Milestone Realty Consultants
$189,000
Bedrooms: 4
Baths: 3
Approx Sq Ft: 2769
8 French Avenue
Winchester, KY 40391
MLS #: 20008653
Subdivision: downtown
OH MY!! Gorgeous stately older home located in the historic part of Winchester. All the charm of yesteryear but all the conveniences for today's lifestyle....
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Re/Max Creative, Winchester
$184,900
Bedrooms: 3
Baths: 1
Approx Sq Ft: 1926
302 W Lexington Avenue
Winchester, KY 40391
MLS #: 20011366
Subdivision: downtown
Price REDUCED!! No more front porch envy as you have the opportunity to make this craftsman-style bungalow your very own. This beautiful home is a living piece...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Keller Williams Greater Lexington
$112,500
Bedrooms: 4
Baths: 1
Approx Sq Ft: 1984
16 Buckner Street
Winchester, KY 40391
MLS #: 20011472
Subdivision: downtown
New Price-New Pics-Must See!! At Recent Appraisal Value! Take a look at this quaint home with historical character and generous amounts of space with 12 foot...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Century 21 Advantage Realty
$107,500
Bedrooms: 3
Baths: 2
Approx Sq Ft: 1554
60 Flanagan Street (Pending)
Winchester, KY 40391
MLS #: 20004677
Subdivision: downtown
With record low interest rates, take advantage of keeping your monthly payment less than you can rent for! As the ideal starter home or investment property,...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Freedom Realty & Property Management
$97,900
Bedrooms: 4
Baths: 3
Approx Sq Ft: 2400
359 E Washington Street (Pending)
Winchester, KY 40391
MLS #: 1908002
Subdivision: downtown
This is a great investment property! It is currently set up as two separate living quarters. They need the finishing touches, but are well on their way to...
Contact Brad Johnson at (859) 333-9912 to inquire about this property.
Listing provided courtesy of Woods Realty Group
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