29 Ascutney St, Windsor, VT 05089
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Property image
OFF MARKET

29 Ascutney St
Windsor, VT 05089

  • 6 Beds
  • 4 Baths
  • 3,592 sqft (on 0.61 acres)

$521,600

Trulia Estimate
as of Aug 23, 2026

$521,600

Trulia Estimate
as of Aug 23, 2026
6 Beds
4 Baths
3,592 sqft
(on 0.61 acres)

Home Value

Trulia Estimate
$522K
Since last month
Decreased$300 (-0.1%)
Since last year
Decreased$3K (-0.5%)
Since last sale
Increased$112K (+27.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +240% in the last 10 years
MonthEstimated value
2026
August 2026$522K
July 2026$522K
June 2026$526K
May 2026$518K
April 2026$515K
March 2026$517K
February 2026$502K
January 2026$501K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
74 Union Street, Windsor, VT
0.06
Single-Family Home
$319,000
07/23/26
4
2
2,142
70-74 State Street, Windsor, VT
0.29
Single-Family Home
$115,000
12/10/25
5
3.5
4,011
32 Clough Avenue, Windsor, VT
0.27
Single-Family Home
$292,500
08/28/25
3
1.5
1,606
31 Maple Street, Windsor, VT
0.33
Single-Family Home
$215,000
10/06/25
3
1.5
1,900
10 McKenzie Drive, Windsor, VT
0.18
Single-Family Home
$271,000
11/13/25
3
1.5
1,320
66 Union Street, Windsor, VT
0.07
Single-Family Home
$219,000
09/02/25
3
2
1,743
93 Belaski Road, Windsor, VT
0.35
Single-Family Home
$565,000
08/17/26
3
3
2,368
3 Cherry Street, Windsor, VT
0.29
Single-Family Home
$259,000
05/01/26
3
1
1,176
9 Main Street, Windsor, VT
0.66
Single-Family Home
$200,001
08/28/25
4
1.5
2,310
1 Dorrance Street, Windsor, VT
0.53
Single-Family Home
$315,000
11/21/25
2
1.5
1,649

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
3 Fitch Court, Windsor, VT 05089
0.05
$238,500
2
2
1,665
Off Market
66 Union Street, Windsor, VT 05089
0.07
$226,800
3
2
1,743
Off Market
74 Union Street, Windsor, VT 05089
0.06
$319,000
4
2
2,142
Recently Sold
32 Ascutney Street, Windsor, VT 05089
0.05
$381,500
4
3
1,998
Off Market
2 Ascutney Street, Windsor, VT 05089
0.15
$314,300
3
1.5
1,364
Off Market
10 McKenzie Drive, Windsor, VT 05089
0.17
$271,000
3
1.5
1,320
Recently Sold
102-104 State Street, Windsor, VT 05089
0.21
$299,400
7
4
3,894
Off Market
17 Dewey Avenue, Windsor, VT 05089
0.18
$125,200
3
1
1,523
Off Market
100 State Street, Windsor, VT 05089
0.21
$252,500
6
1.5
2,880
Off Market
17 Clough Avenue, Windsor, VT 05089
0.21
$284,800
4
2
3,266
Off Market
25.5 Union Street, Windsor, VT 05089
0.25
$187,800
2
1
1,115
Off Market
153 State Street, Windsor, VT 05089
0.23
$267,800
4
1.5
1,600
Off Market

Local Information

  • Map ViewExplore the area around 29 Ascutney St.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1880
Lot Size
0.61 acres
Living Area
3,592 sqft
Price/Sqft
$145

About this House

This could be a great buy for someone looking to live in one unit and collect rent on other units to help with mortgage payments. Great opportunity to own a 4 unit historic building in Windsor. Brick exterior, some new roof in 2007. New boiler in 2008. Front 2 units need some updates, rear two units need work. Most electric has been updated. Nice yard with detached garage, storage. Close to Schools and Kennedy Pond. Walk to downtown!. Subject to estate obtaining the license to sell Brokered And Advertised By: Century 21 Energy Shield Realty/Lebanon Listing Agent: William Sahlman
29 Ascutney St, Windsor, VT 05089 is a 6 bedroom, 4 bathroom, 3,592 sqft single-family home built in 1880. It last sold for $410,000 on Apr 8, 2022. It is currently off market. The Trulia Estimate is $521,600, with a rent estimate of $4,500/month.

Home Details for 29 Ascutney St

Interior Features

Heating & Cooling
Heating: OilHeating Fuel: Oil

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick
Parking & Garage
Parking Space: 1

Property Information

Year Built
Year Built: 1880
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 4

Lot Information

Lot Area: 0.61 acres

Price and Tax history

DateEventPrice
Apr 8, 2022
Source: PrimeMLS #4860808
Sold
$410,000
Feb 10, 2022
Source: PrimeMLS #4860808
Contingent
$425,000
Jul 25, 2021
Source: PrimeMLS #4860908
PriceChange
$425,000
Price decreased by 11%
May 14, 2021
Source: PrimeMLS #4860808
Listed For Sale
$475,000
Apr 10, 2013
Source: N/A
Sold
$100,000

Market trends in Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
6

Around this home

What Locals Say about Windsor

At least 10 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 92 % Say yards are well-kept

  • 91 % Say it's walkable to grocery stores

  • 83 % Say car is needed

  • 80 % Say it's walkable to restaurants

  • 69 % Say people would walk alone at night

  • 64 % Say there's holiday spirit

  • 64 % Say kids play outside

  • 64 % Say there are sidewalks

  • 64 % Say streets are well-lit

  • 60 % Say there's wildlife

  • 60 % Say parking is easy

  • 58 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 36 % Say they plan to stay for at least 5 years

  • 20 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Brianna W.
    "It’s small but fun. It’s got a local salon, pizza chef, and a hospital, fire/police department, and a school all within a mile of each other."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 29 Ascutney St

  • What is 29 Ascutney St estimated to be worth?
    Trulia's estimated value for 29 Ascutney St in Windsor, VT is $521,600.
  • What is the price history for 29 Ascutney St?
    29 Ascutney St in Windsor, VT last sold for $410,000 in April 2022.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Windsor?
    Residents describe Windsor, VT as dog-friendly, well-kept, and walkable to grocery stores. See recently sold homes in Windsor, VT.
  • How big is the lot at 29 Ascutney St?
    The lot at 29 Ascutney St in Windsor, VT is about 0.26 acres (11,326 sq ft).
  • Does 29 Ascutney St have parking?
    Yes, 29 Ascutney St in Windsor, VT has on-site parking.

Apartments for Rent

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Off Market Homes Near 29 Ascutney St

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