Winchester KY Real Estate &

8 Properties Found

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Beds:
4
Baths:
4.00
Sq.Ft.:
2,072
Status:
NEW LISTING
MLS#:
26000922
Type:
Duplex
Subdivision:
Hale Heights
Lot size:
0.15 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Coldwell Banker McMahan 859-266-1800
View additional info

ADDITIONAL INFORMATION

Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees.

Beds:
8
Baths:
8.00
Sq.Ft.:
4,000
Status:
Active
MLS#:
26000777
Type:
Apartment
Subdivision:
Downtown
Lot size:
0.06 Acres
A broker reciprocity listing Courtesy: The Brokerage 859-983-7365
View additional info

ADDITIONAL INFORMATION

Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Ave, a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This multifamily property is ideally situated in historic downtown Winchester, within walking distance to shops, restaurants, and local attractions, making it highly desirable for renters seeking urban living with small-town charm. Just minutes from I-64 and only 25 minutes to Lexington and Hamburg Pavilion, this property provides easy access for commuters and investors alike. This is a fantastic opportunity to expand your portfolio with an income-producing asset in a growing market.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,007
Status:
Active
MLS#:
26000780
Type:
Triplex
Subdivision:
Downtown
Lot size:
0.16 Acres
Year built:
1930
A broker reciprocity listing Courtesy: The Brokerage 859-983-7365
View additional info

ADDITIONAL INFORMATION

INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered together, landlord does cover utility expenses. Please call with any questions, please do not disturb the tenants!

Beds:
12
Baths:
4.00
Sq.Ft.:
4,010
Status:
Active
MLS#:
26000197
Type:
Fourplex
Subdivision:
Downtown
Lot size:
0.41 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Marshall Lane Real Estate - Lexington 502-682-1226
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ADDITIONAL INFORMATION

Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units rent for $800 and $875. The two upper units have had the same tenants for a number of years. There is ample parking for tenants and guests.

Beds:
7
Baths:
3.00
Sq.Ft.:
3,393
Status:
Active
MLS#:
25508389
Type:
Duplex
Subdivision:
Downtown
Lot size:
0.16 Acres
Year built:
1940
A broker reciprocity listing Courtesy: KB Realty Group 606-263-0046
View additional info

ADDITIONAL INFORMATION

This investment property has strong rent potential to add to your portfolio. Property is conveniently located in the heart of Downtown Winchester and is zoned R-4. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Downstairs unit has 4 bedrooms and 2 full bathrooms, and its currently leased for $1,495 a month. The upstairs unit boasts 3 bedrooms and 1 full bathroom, and its ready for a tenant to move in. This property is nicely updated with low-maintenance flooring running throughout both units. You won't want to miss taking a look at this property today.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,683
Status:
Active
MLS#:
25507680
Type:
Duplex
Subdivision:
South Park Addition
Lot size:
0.19 Acres
Year built:
1930
A broker reciprocity listing Courtesy: The Agency 859-285-0614
View additional info

ADDITIONAL INFORMATION

This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

Beds:
8
Baths:
4.00
Sq.Ft.:
5,046
Status:
Active
MLS#:
25505825
Type:
Fourplex
Subdivision:
Burns Addition
Lot size:
6,098 Acres
Year built:
1912
A broker reciprocity listing Courtesy: Big Blue Realty 859-420-5477
View additional info

ADDITIONAL INFORMATION

Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new roof, updated interiors, and a clean, professional aesthetic ideal for long-term tenants with all the appliances included. Additional features include: Prime downtown location — walkable to shops, dining, and local attractions, 4 parking spots ( 1 for each unit), as well as, off street parking available. Strong rental potential in a growing market Zoned and ready for investment use

Beds:
5
Baths:
3.00
Sq.Ft.:
2,762
Status:
Active
MLS#:
25015191
Type:
Multi-Family
Subdivision:
South Park Addition
Lot size:
0.2 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Bluegrass Realty Pros, Inc 270-312-2943
View additional info

ADDITIONAL INFORMATION

Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

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Andrea D. Conner, License 221773, Xome Inc., License 239054, [email protected], 844-400-XOME (9663), 1795 Alysheba Way, Suite 102, Lexington, KY 40509


The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Lexington Bluegrass Multiple Listing Service. The Broker providing this data believes them to be correct but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2026 Lexington Bluegrass Multiple Listing Service. All rights reserved.



Winchester Real Estate

Winchester is located in Kentucky. Winchester, Kentucky has a population of 18,993. Winchester is less family-centric than the surrounding county with 25.63% of the households containing married families with children. The county average for households married with children is 25.74%.

The median household income in Winchester, Kentucky is $47,034. The median household income for the surrounding county is $59,294 compared to the national median of $69,021. The median age of people living in Winchester is 36.9 years.

Winchester Weather

The average high temperature in July is 85.8 degrees, with an average low temperature in January of 22 degrees. The average rainfall is approximately 45.8 inches per year, with 9.4 inches of snow per year.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $305,000
    19.3%
    change since last quarter
  • # Active listings

    205
    30-day change

Winchester Schools and Demographics

Education near Winchester, KY

City County
High School Graduates 86.63 89.23
College Degree - 2 year 8.6 9.97
College Degree - 4 year 19.04 20.05
Graduate Degree 4.07 5.81
Expenditures per Student 14,536 14,536
Students per Teacher 13.6 13.6

Elementary Schools near Winchester, KY

Grades Students P/T Ratio ZIP
Athens-Chilesburg Elementary School KG - 05 745 14.9 40509
Camargo Elementary School PK - 04 612 13.2 40353
Clark County Preschool PK - PK 296 24.7 40391
Clay City Elementary School PK - 05 535 16.7 40312
Mapleton Elementary School KG - 04 674 14.7 40353
Montgomery County Early Learning Center PK - PK 109 18.2 40353
Mount Sterling Elementary School KG - 04 635 15.1 40353
North Middletown Elementary School KG - 05 155 14.8 40357
Shearer Elementary School KG - 04 423 12 40391
Strode Station Elementary School KG - 04 613 12.4 40391
William G. Conkwright Elementary KG - 04 563 20 40391
Willis H. Justice Elementary School KG - 04 491 16.2 40391

Middle Schools near Winchester, KY

Grades Students P/T Ratio ZIP
Edythe Jones Hayes Middle School 06 - 08 1,095 15.6 40509
McNabb Middle School 07 - 08 718 16.2 40353
Mercer County 9th Grade Academy 09 - 09 224 16.2 40391
Montgomery County Intermediate School 05 - 06 712 15.6 40353
Rev. Henry E. Baker SR. Interm. School 05 - 06 858 19.5 40391
Robert D. Campbell Jr. High 07 - 08 801 18.2 40391
Willis H. Justice Elementary School KG - 05 0 13.7 40391

High Schools near Winchester, KY

Grades Students P/T Ratio ZIP
George Rogers Clark High School 09 - 12 1,672 18.2 40391
Montgomery County High School 09 - 12 1,338 18.4 40353

Ungraded Schools near Winchester, KY

Grades Students P/T Ratio ZIP
* Gateway Children's Services 07 - 12 18 9 40353
* Hillcrest Hall Treatment Center 09 - 12 12 12 40353
* Phoenix Academy 07 - 12 22 4.4 40391
* The Sterling School 09 - 12 51 11.3 40353
Clark County Area Technology Center UG - UG 0 40392
Hayes Pre-School UG - UG 93 30.5 40509
Montgomery County Accelerated Academy UG - UG 0 40353
Montgomery County Area Technology Center UG - UG 0 40353

Demographics near Winchester, KY

City County
Neighborhood Type Suburban
Population 18,993 36,716
Population Density 2,078 145
Median Age 36.9 41.5
People per Household 2.3 2.5
Median Household Income 47,034 59,294
Average Income per Capita 28,337 33,205

Real estate near Winchester