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Winchester, KY Multifamily Homes & Duplexes for Sale

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  • /37

    $1,595,000

    • 37 Beds
    • 19.5 Baths
    • 26,124 Sq Ft

    2 N Main St, Winchester, KY 40391

    Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule!The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

    Blanca Cheung Tsubaki Group, LLC

    2 N Main St, Winchester, KY 40391
  • /3

    $251,000

    • 6 Beds
    • 3 Baths
    • 2,302 Sq Ft

    133 S Highland St, Winchester, KY 40391

    16 Central Ave, Winchester, KY 40391Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close

    David Espinosa Bluegrass Realty Pros, Inc

    133 S Highland St, Winchester, KY 40391
  • /3

    $290,000

    • 6 Beds
    • 4 Baths
    • 2,511 Sq Ft

    16 Central Ave, Winchester, KY 40391

    16 Central Ave, Winchester, KY 40391Excellent multi-family investment opportunity in a convenient Winchester location! This 11⁄2-story property features two spacious rental units, offering strong income potential. The first unit boasts 4 bedrooms and 3 bathrooms, providing ample space for larger households. The second unit includes 2 bedrooms and 1 bathroom, perfect for smaller families or

    David Espinosa Bluegrass Realty Pros, Inc

    16 Central Ave, Winchester, KY 40391
  • /3

    $426,000

    • 5 Beds
    • 4 Baths

    1028 W Lexington Ave, Winchester, KY 40391

    1028 W Lexington Ave, Winchester, KY 40391Investor's dream in the heart of Winchester! This 11⁄2-story property features four rental units, offering a great mix of layouts to appeal to a variety of tenants. The main unit includes 2 bedrooms and 1 bathroom, while the remaining three units each offer 1 bedroom and 1 bathroom, providing consistent rental income potential. With its established

    David Espinosa Bluegrass Realty Pros, Inc

    1028 W Lexington Ave, Winchester, KY 40391
  • /19

    $270,000

    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft

    211 College St, Winchester, KY 40391

    Welcome to 211 College Street in Winchester, KY — a fantastic investment opportunity located just minutes from downtown! This charming duplex is currently being used as a rental and offers two spacious units, each featuring 2 bedrooms and 1 full bathroom. It also has a detached 1-car garage. With a strong rental history and separate entrances, this property is ideal for investors seeking

    David Espinosa Bluegrass Realty Pros, Inc

    211 College St, Winchester, KY 40391
  • /6

    $388,000

    • 5 Beds
    • 3 Baths
    • 2,762 Sq Ft

    101 E Lexington Ave, Winchester, KY 40391

    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.

    David Espinosa Bluegrass Realty Pros, Inc

    101 E Lexington Ave, Winchester, KY 40391
  • /4

    $650,000

    • 8 Beds
    • 5 Baths
    • 3,834 Sq Ft

    202 S Maple St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This 5-unit has 3 - 2 bed 1 bath units,1 - 1 bed 1 bath unit and a studio. 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.

    David Espinosa Bluegrass Realty Pros, Inc

    202 S Maple St, Winchester, KY 40391
  • /2

    $255,000

    • 4 Beds
    • 2 Baths
    • 2,732 Sq Ft

    206 S Maple St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 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.

    David Espinosa Bluegrass Realty Pros, Inc

    206 S Maple St, Winchester, KY 40391
  • /12

    $295,000

    • 6 Beds
    • 4 Baths
    • 3,035 Sq Ft

    117 Linden Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 3 bed 2 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.

    David Espinosa Bluegrass Realty Pros, Inc

    117 Linden Ave, Winchester, KY 40391
  • /14

    $292,000

    • 6 Beds
    • 2 Baths
    • 3,196 Sq Ft

    124 S Burns Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This duplex has a 3 bed 1 bath unit and a 3 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.

    David Espinosa Bluegrass Realty Pros, Inc

    124 S Burns Ave, Winchester, KY 40391
  • /3

    $221,000

    • 4 Beds
    • 2 Baths
    • 2,600 Sq Ft

    223 W Hickman St, Winchester, KY 40391

    Here's your chance to own a nice investment property. This duplex has a 2 bed 1 bath unit and a 2 bed one 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.

    David Espinosa Bluegrass Realty Pros, Inc

    223 W Hickman St, Winchester, KY 40391
  • /9

    $274,000

    • 5 Beds
    • 3 Baths
    • 2,384 Sq Ft

    135 Winn Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This duplex has a 3 bed 2 bath unit and a 2 bed one 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.

    David Espinosa Bluegrass Realty Pros, Inc

    135 Winn Ave, Winchester, KY 40391
  • /17

    $1,350,000

    16 Linden Ave, Winchester, KY 40391

    Income-Producing 16-Unit Apartment complex in the Heart of WinchesterTurn-key opportunity on North Maple Avenue—just minutes from Downtown Winchester and a quick 20-minute drive to Lexington via I-64. Consisting of sixteen one-bed/one-bath apartments on a 0.34-acre lot with 20 parking spaces, the property has a 2022 new roof, new vinyl siding added in 2023, and several fully

    Patrick Doyle National Real Estate

    16 Linden Ave, Winchester, KY 40391
  • /79

    $239,900

    • 4 Beds
    • 2 Baths
    • 3,295 Sq Ft

    133 S Burns Ave, Winchester, KY 40391

    Beautiful, Old-World style in the heart of Winchester! From the red, domed porch roof to the arched doorways and multiple fireplaces, this home is full of character and class. Being sold as-is, but with many renovations and updates already done to maintain and restore the charm of this old beauty including a new shingle roof (2024), replaced porch boards, and a fresh coat of interior paint. The

    Josh Wood Freedom Realty & Property Management

    133 S Burns Ave, Winchester, KY 40391
  • /2

    $5,646,000

    • 2 Beds
    • 3 Baths
    • 37,192 Sq Ft

    175 Chatham Place, Winchester, KY 40391

    36 Townhomes ,located behind Lowes,Winchester,Ky.Great rental property, owner will do some owner financing

    Garry Milton Milton and Associates Real Estate

    175 Chatham Place, Winchester, KY 40391

Why Live in Winchester

Winchester, KY, the largest city in Clark County, is known for its vibrant community and unique local flavors, including the birthplace of beer cheese and Ale-8-One soda. Main Street is the hub for dining, featuring popular spots like La Trattoria and Loma’s, and the Beer Cheese Trail, which includes around 15 restaurants with signature beer cheese recipes. The city offers practical amenities with nearby grocery stores like Kroger and Walmart Supercenter, and retail options such as TJ Maxx and Lowe’s. Housing in Winchester includes Victorian-era inspired homes and newer subdivisions, with properties often featuring gravel driveways and spacious lawns suitable for gardens. Clark County Public Schools provide strong academic programs, including AP and dual enrollment courses at George Rogers Clark High School. For outdoor activities, residents enjoy Legacy Grove Park, College Park, and Lykins Park, which offer facilities for basketball, tennis, hiking, and disc golf. Winchester hosts annual events like the Beer Cheese Festival and the Daniel Boone Pioneer Festival, attracting visitors with arts, crafts, and food. The Bluegrass Heritage Museum showcases the history of Central Kentucky. Commuting is convenient with Winchester located 16 miles from Lexington and 20 miles from Richmond. The city has a cooperative community spirit, bolstered by investments from younger residents and a thriving local economy.

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$240,000
Median Single Family Sale Price
$259,950
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$159
Number of Homes for Sale
81
Last 12 months Home Sales
303
Months of Supply
3.20
Median List Price
$260,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
2%
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