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Winchester, KY Multifamily Homes & Duplexes for Sale

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  • /13

    $245,000

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

    130 E Broadway St, Winchester, KY 40391

    Wonderful investment opportunity! Cash flowing triplex located in the heart of Winchester. One unit has just been renovated and is ready for a new tenant. The other two have longstanding tenants who pay every month. Great price for the rent potential!

    Andrew Jarvis Lifstyl Real Estate

    130 E Broadway St, Winchester, KY 40391
  • /15

    $600,000

    • 8 Beds
    • 4 Baths
    • 5,046 Sq Ft

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

    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

    Priya Patel-Rossetti Big Blue Realty

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
  • /13

    $257,500

    • 5 Beds
    • 3 Baths
    • 3,007 Sq Ft

    221 S Highland St, Winchester, KY 40391

    INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depreciation. 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

    Joshua Lynch The Brokerage

    221 S Highland St, Winchester, KY 40391
  • /29

    $424,900

    • 8 Beds
    • 8 Baths
    • 4,000 Sq Ft

    17 W Lexington Ave, Winchester, KY 40391

    Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Avenue — 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 turn-key multifamily property is ideally situated in historic downtown Winchester, within walking

    Joshua Lynch The Brokerage

    17 W Lexington Ave, Winchester, KY 40391
  • /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
  • /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
  • /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
$248,000
Median Single Family Sale Price
$260,000
Median Townhouse Sale Price
$194,500
Average Price Per Sq Ft
$161
Number of Homes for Sale
89
Last 12 months Home Sales
331
Months of Supply
3.20
Median List Price
$265,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
6%
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