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Windsor, VT Multifamily Homes & Duplexes for Sale

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  • 358 Us Route 5 S, Windsor, VT 05089
    358 Us Route 5 S, Windsor, VT 05089
    358 Us Route 5 S, Windsor, VT 05089
    /36

    $325,000

    • 2,452 Sq Ft

    358 Us Route 5 S, Windsor, VT 05089

    Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

    Daniel Preston KW Vermont Woodstock

    358 Us Route 5 S, Windsor, VT 05089
  • 1185 U S 5 S, Windsor, VT 05089
    1185 U S 5 S, Windsor, VT 05089
    1185 U S 5 S, Windsor, VT 05089
    /3

    $590,000

    • 17 Beds
    • 2,768 Sq Ft

    1185 U S 5 S, Windsor, VT 05089

    Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable

    Katie Ladue Gilbert KW Vermont Woodstock

    1185 U S 5 S, Windsor, VT 05089
  • 102-104 State St, Windsor, VT 05089
    102-104 State St, Windsor, VT 05089
    /2

    $379,000

    • 7 Beds
    • 4 Baths
    • 3,894 Sq Ft

    102-104 State St, Windsor, VT 05089

    INVESTMENT PROPERTY. 4 UNITS, 1 1-bedroom unit & 3 2-bedroom units. Separate basement for each unit. Recent improvement includes, new roof, replaced plywood, foam board and membrane, at a cost of $70,600.00. Heat is separate pellet stoves for each unit, also an oil-fired steam system if needed for backup. Electric is separate, tenants pay electric. Landlord pays heat. Minimum of 48-hour required

    Don Chabot Town and Country Realty

    102-104 State St, Windsor, VT 05089
Vermont Windsor

Multi-Family Homes & Duplexes for Sale in Windsor, VT

Why Live in Windsor

Windsor, nestled in the shadow of Mount Ascutney and along the Connecticut River, is a historic township with around 3,500 residents. Known as the "birthplace of Vermont," it offers a mix of outdoor recreation, shops, and dining options in its small downtown area. The neighborhood has seen an influx of younger residents since 2020, drawn by the remote work lifestyle. Homes vary from late 1700s and mid-1800s builds to Cape Cods and ranch-style homes from the 1930s to 1950s. Properties range from smaller lots in town to expansive country lots with dense woods or open farmland. Windsor's crime rate is lower than the national average. Outdoor enthusiasts can enjoy Paradise Park's trails, Mount Ascutney's revived recreational facilities, and canoeing or kayaking with Great River Outfitters. Downtown Windsor features Artisans Park with Harpoon Brewery, Silo Distillery, and more, while Windsor Station Restaurant and Barroom offers a unique dining experience in an old train depot. The Autumn Moon Festival and a year-round farmers market add to the local charm. Windsor School serves pre-kindergarten through 12th grade. The town is well-connected with Interstate 91, U.S. Route 5, and daily Amtrak service, with Claremont, New Hampshire, just 10 miles away.
Learn more about living in Windsor

Home Trends in Windsor, VT

On average, homes in Windsor, VT sell after 58 days on the market compared to the national average of 50 days. The median sale price for homes in Windsor, VT over the last 12 months is $275,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$275,000
Median Single Family Sale Price
$274,000
Median Townhouse Sale Price
$821,500
Average Price Per Sq Ft
$211
Number of Homes for Sale
7
Last 12 months Home Sales
31
Months of Supply
2.70
Median List Price
$289,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Finance a Home How to Sell a Home

In Windsor, there are currently 3 multi-family homes for sale, providing an appealing investment opportunity for buyers. With multi-family homes priced between $325,000 to $590,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Windsor is $289,000, while the average sale price is $351,500, offering insights into the local housing market. On average, multi-family homes spend 58 days listed before being sold. Multi-family homes include a variety of property types, from duplexes, triplexes, and fourplexes, to apartment complexes, all within a single building divided to accommodate multiple families living separately. These multi-family properties for sale offer investors the chance to generate rental income. Whether you're considering a duplex for a beginner investment or an apartment complex for a more substantial venture, there are investment properties available to meet your requirements. Explore the range of multi-family homes for sale in Windsor, VT.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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