165 State St, Windsor, VT 05089
OFF MARKET

165 State St
Windsor, VT 05089

  • 6 Beds
  • 3.5 Baths
  • 4,182 sqft (on 4.70 acres)

$719,700

Trulia Estimate
as of Aug 13, 2026

$719,700

Trulia Estimate
as of Aug 13, 2026
6 Beds
3.5 Baths
4,182 sqft
(on 4.70 acres)

Home Value

Trulia Estimate
$720K
Since last month
Decreased$42K (-5.5%)
Since last year
Decreased$54K (-7%)
Since last sale
Increased$500K (+227.1%)
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 +61% in the last 10 years
MonthEstimated value
2026
August 2026$720K
July 2026$731K
June 2026$761K
May 2026$750K
April 2026$726K
March 2026$724K
February 2026$701K
January 2026$697K
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
70-74 State Street, Windsor, VT
0.44
Single-Family Home
$115,000
12/10/25
5
3.5
4,011
74 Union Street, Windsor, VT
0.34
Single-Family Home
$319,000
07/23/26
4
2
2,142
66 Union Street, Windsor, VT
0.36
Single-Family Home
$219,000
09/02/25
3
2
1,743
672 County Road, Windsor, VT
0.72
Single-Family Home
$340,000
09/05/25
3
2
1,500
9 Main Street, Windsor, VT
0.71
Single-Family Home
$200,001
08/28/25
4
1.5
2,310
31 Maple Street, Windsor, VT
0.62
Single-Family Home
$215,000
10/06/25
3
1.5
1,900
32 Clough Avenue, Windsor, VT
0.55
Single-Family Home
$292,500
08/28/25
3
1.5
1,606
10 McKenzie Drive, Windsor, VT
0.47
Single-Family Home
$271,000
11/13/25
3
1.5
1,320
3 Cherry Street, Windsor, VT
0.45
Single-Family Home
$259,000
05/01/26
3
1
1,176
4 Bavier Avenue, Windsor, VT
0.66
Single-Family Home
$226,000
08/07/26
3
1
2,088

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
18 County Road, Windsor, VT 05089
0.10
$343,200
3
2
1,400
Off Market
153 State Street, Windsor, VT 05089
0.09
$265,600
4
1.5
1,600
Off Market
17 Dewey Avenue, Windsor, VT 05089
0.12
$125,200
3
1
1,523
Off Market
2 Ascutney Street, Windsor, VT 05089
0.20
$315,700
3
1.5
1,364
Off Market
32 Ascutney Street, Windsor, VT 05089
0.27
$382,700
4
3
1,998
Off Market
102-104 State Street, Windsor, VT 05089
0.32
$300,900
7
4
3,894
Off Market
100 State Street, Windsor, VT 05089
0.33
$253,500
6
1.5
2,880
Off Market
74 Union Street, Windsor, VT 05089
0.34
$319,000
4
2
2,142
Recently Sold
3 Fitch Court, Windsor, VT 05089
0.34
$239,500
2
2
1,665
Off Market
66 Union Street, Windsor, VT 05089
0.36
$227,900
3
2
1,743
Off Market
70-74 State Street, Windsor, VT 05089
0.44
$115,000
5
3.5
4,011
Recently Sold
18 Pine Street, Windsor, VT 05089
0.47
$407,300
3
1.5
2,273
Off Market

Local Information

  • Map ViewExplore the area around 165 State St.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1916
Lot Size
4.7 acres
Living Area
4,182 sqft
Price/Sqft
$172
Parking
Garage

About this House

They don't build houses like this anymore. This amazing colonial revival house has been updated to like-new condition while maintaining the period charm. High ceilings, wood floors, custom built-ins, chandeliers, this house has it all. The recently remodeled kitchen features custom cabinetry reproduced in the style of existing woodwork in the house. Completely private location just minutes from the town center, and within 30 minutes of Dartmouth College and downtown Woodstock. Fabulous mountain views!
165 State St, Windsor, VT 05089 is a 6 bedroom, 5 bathroom, 4,182 sqft single-family home built in 1916. It last sold for $220,000 on Jul 28, 1998. It is currently off market. The Trulia Estimate is $719,700, with a rent estimate of $3,799/month.

Home Details for 165 State St

Interior Features

Heating & Cooling
Heating: Radiant, Stove, OilHeating Fuel: Radiant
Interior Details
Number of Rooms: 8Types of Rooms: Dining Room
Appliances & Utilities
RefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: Wood
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1916
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 4.70 acres

Price and Tax history

DateEventPrice
Jun 25, 2020
Source: Agent Provided
ListingRemoved
$410,000
Jun 25, 2019
Source: Agent Provided
Listed For Sale
$410,000
Dec 13, 2016
Source: Agent Provided
ListingRemoved
$460,000
Dec 12, 2015
Source: Agent Provided
Listed For Sale
$460,000
Oct 4, 2015
Source: Agent Provided
ListingRemoved
$460,000

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
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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."
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Apartments for Rent

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Homes for sale near 165 State St

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Off Market Homes Near 165 State St

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Frequently asked questions about 165 State St

  • What is 165 State St estimated to be worth?
    Trulia's estimated value for 165 State St in Windsor, VT is $719,700.
  • What is the price history for 165 State St?
    165 State St in Windsor, VT last sold for $220,000 in July 1998.
  • 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 165 State St?
    The lot at 165 State St in Windsor, VT is about 4.7 acres.
  • Does 165 State St have a garage?
    Yes, 165 State St in Windsor, VT has a garage.