125 Highfield Dr, Windsor, VT 05089
Views to Ascutney
1 BR Caretakers apartment
OFF MARKET

125 Highfield Dr
Windsor, VT 05089

  • 2 Beds
  • 3 Baths
  • 2,320 sqft (on 11.20 acres)

$803,000

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $5,460/mo*

$803,000

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $5,460/mo*
2 Beds
3 Baths
2,320 sqft
(on 11.20 acres)

Home Value

Trulia Estimate
$803K
Since last month
Increased$15K (+1.9%)
Since last year
Decreased$23K (-2.7%)
Since last sale
Increased$450K (+128.7%)
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 +111% in the last 10 years
MonthEstimated value
2026
August 2026$800K
July 2026$785K
June 2026$816K
May 2026$793K
April 2026$774K
March 2026$772K
February 2026$784K
January 2026$773K
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
0.19
Single-Family Home
$637,500
02/27/26
3
3
3,490
0.22
Single-Family Home
$1,150,000
11/20/25
3
3.5
2,424
0.26
Single-Family Home
$405,000
08/25/25
4
4
3,012
1.35
Single-Family Home
$1,200,000
11/21/25
4
3
2,252
0.81
Single-Family Home
$987,500
07/26/26
1
1.5
1,369
1.44
Single-Family Home
$705,000
09/08/25
3
3
2,032
1.10
Single-Family Home
$1,925,000
06/26/26
4
3.5
5,173
1.15
Single-Family Home
$900,000
10/02/25
4
3.5
3,830
1.46
Single-Family Home
$485,000
08/21/26
5
3
3,120
1.83
Single-Family Home
$720,000
11/08/25
3
2
2,727

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
0.19
$637,500
3
3
3,490
Recently Sold
0.22
$1,150,000
3
3.5
2,424
Recently Sold
0.50
$614,800
3
1.5
2,004
Off Market
0.63
$1,325,000
2
1.5
1,817
For Sale
0.72
$1,610,900
3
3.5
2,943
Off Market
0.81
$987,500
1
1.5
1,369
Recently Sold
0.84
$659,200
2
2
1,600
Off Market
0.82
$347,000
3
1
1,620
Recently Sold
0.99
$966,800
4
4
4,000
Off Market
1.03
$1,450,000
3
1.5
1,360
For Sale
1.10
$1,925,000
4
3.5
5,173
Recently Sold
1.15
$929,700
4
3.5
3,830
Off Market

Local Information

  • Map ViewExplore the area around 125 Highfield Dr.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
11.2 acres
Living Area
2,320 sqft
Price/Sqft
$346

About this House

Horse Property! Newer Cape with large sunny rooms.2 BR 2.5 Ba with easy to finish 2nd floor offering room for 2 more bedrooms and possible bath.(permits required) Attached heated tack room (w/half bath) leads to 10 stall barn. 11 Open acres, fenced with 3 run in sheds.Very comfortable 1 b/r apt with kitchen and 3/4 Ba. Great location for riding Brokered And Advertised By: Dark Horse Realty Property Services Listing Agent: Dana Waters
125 Highfield Dr, Windsor, VT 05089 is a 2 bedroom, 3 bathroom, 2,320 sqft single-family home built in 1999. It last sold for $350,000 on May 31, 2013. It is currently off market. The Trulia Estimate is $803,000, with a rent estimate of $3,701/month.

Home Details for 125 Highfield Dr

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Interior Features

Interior Details
In-law unitCeiling Fan
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Lot Information

Lot Area: 11.20 acres

Price and Tax history

DateEventPrice
May 31, 2013
Source: N/A
Sold
$350,000
Nov 20, 2012
Source: Agent Provided
Listed For Sale
$399,000
Apr 19, 2012
Source: Agent Provided
ListingRemoved
$499,000
Jun 9, 2011
Source: Agent Provided
Listed For Sale
$499,000
Feb 13, 2011
Source: Agent Provided
ListingRemoved
$595,000

Market trends in West Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
12
1
MoM

What Locals Say about West Windsor

At least 2 Trulia users voted on each feature.
  • 100 % Say parking is easy

  • 100 % Say kids play outside

  • 100 % Say people would walk alone at night

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 75 % Say there are community events

  • 75 % Say there's holiday spirit

  • 67 % Say it's dog friendly

  • 50 % Say neighbors are friendly

  • 33 % Say it's walkable to restaurants

  • 33 % Say streets are well-lit

  • 25 % Say there are sidewalks

  • 25 % Say it's walkable to grocery stores

  • 25 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 125 Highfield Dr

  • What is 125 Highfield Dr estimated to be worth?
    Trulia's estimated value for 125 Highfield Dr in Windsor, VT is $803,000.
  • What is the price history for 125 Highfield Dr?
    125 Highfield Dr in Windsor, VT last sold for $350,000 in May 2013.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 125 Highfield Dr?
    The closest schools to 125 Highfield Dr in Windsor, VT are Albert Bridge School (West Windsor) (Pre-K/Elementary), Windsor School (K-12, rated 4/10).
  • Does 125 Highfield Dr have laundry facilities?
    Yes, 125 Highfield Dr in Windsor, VT has in-unit laundry.
  • How big is the lot at 125 Highfield Dr?
    The lot at 125 Highfield Dr in Windsor, VT is about 11.2 acres.

Apartments for Rent

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Off Market Homes Near 125 Highfield Dr

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Homes for sale near 125 Highfield Dr

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