29 Ascutney St, Windsor, VT 05089
OFF MARKET

29 Ascutney St
Windsor, VT 05089

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

$518,400

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $3,519/mo*
Refinance Your Home

$518,400

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $3,519/mo*
Refinance Your Home
6 Beds
4 Baths
3,592 sqft
(on 0.61 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 29 Ascutney St

DatePriceEventSource
04/08/2022$410,000Sold
PrimeMLS #4860808
02/10/2022$425,000ContingentPrimeMLS #4860808
07/25/2021$425,000PriceChange
PrimeMLS #4860908
05/14/2021$475,000Listed For SalePrimeMLS #4860808
04/10/2013$100,000Sold
N/A
07/19/2012$179,000PriceChange
Agent Provided
07/18/2012$199,500PriceChange
Agent Provided
02/07/2012$179,000PriceChange
Agent Provided
10/01/2011$194,900PriceChange
Agent Provided
08/20/2011$199,500PriceChange
Agent Provided
08/06/2011$198,500PriceChange
Agent Provided
03/24/2011$199,500Listed For SaleAgent Provided
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax
Assessment$367,170
Home facts updated by county records

Comparable Sales for 29 Ascutney St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
30 Union Street, Windsor, VT
0.28
Single-Family Home
$350,000
05/30/25
4
4.5
3,990
70-74 State Street, Windsor, VT
0.29
Single-Family Home
$115,000
12/10/25
5
3.5
4,011
3 Fitch Court, Windsor, VT
0.05
Single-Family Home
$229,000
06/25/25
2
2
1,665
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
42 Elm Street, Windsor, VT
0.41
Single-Family Home
$275,000
06/09/25
3
2
1,264
338 US Route 5 South, Windsor, VT
0.67
Single-Family Home
$240,000
07/21/25
6
2
2,504
3 Cherry Street, Windsor, VT
0.29
Single-Family Home
$259,000
05/01/26
3
1
1,176

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 29 Ascutney St.

What Locals Say about Windsor

At least 9 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 92 % Say yards are well-kept

  • 90 % Say it's walkable to grocery stores

  • 83 % Say car is needed

  • 78 % Say it's walkable to restaurants

  • 67 % Say parking is easy

  • 67 % Say people would walk alone at night

  • 64 % Say streets are well-lit

  • 64 % Say it's quiet

  • 64 % Say there are sidewalks

  • 64 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature

Homes for sale near 29 Ascutney St

Skip to last item
Skip to first item

Off Market Homes Near 29 Ascutney St

Skip to last item
Skip to first item

Homes for rent near 29 Ascutney St

Skip to last item
Skip to first item
29 Ascutney St, Windsor, VT 05089 is a 6 bedroom, 4 bathroom, 3,592 sqft single-family home built in 1880. This property is not currently available for sale. 29 Ascutney St was last sold on Apr 8, 2022 for $410,000. The current Trulia Estimate for 29 Ascutney St is $518,400.