257 Herbert Hill Rd, Windsor, VT 05089
OFF MARKET

$519,700

Trulia Estimate
  • Studio

257 Herbert Hill Rd, Windsor, VT 05089

Refinance Your Home

Home Value

Trulia Estimate
$520K
Since last month
Decreased$6K (-1.1%)
Since last year
Increased$8K (+1.6%)
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 +83% in the last 10 years
MonthEstimated value
2026
August 2026$521K
August 2026$520K
July 2026$527K
June 2026$538K
May 2026$543K
April 2026$531K
March 2026$541K
February 2026$521K
January 2026$485K
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
16 Ascutney St, Windsor, VT
1.16
Single-Family Home
$227,940
05/04/26
-
-
16 Day Street, Windsor, VT
1.05
Single-Family Home
$94,900
12/04/25
2
1
660
26 Cherry St, Windsor, VT
1.07
Single-Family Home
$150,000
11/03/25
-
-
2505 County Road, Windsor, VT
1.56
Single-Family Home
$299,000
09/30/25
2
1
1,332
1 Dorrance Street, Windsor, VT
1.09
Single-Family Home
$315,000
11/21/25
2
1.5
1,649
4 Bavier Avenue, Windsor, VT
1.14
Single-Family Home
$226,000
08/07/26
3
1
2,088
3 Cherry Street, Windsor, VT
1.19
Single-Family Home
$259,000
05/01/26
3
1
1,176
21 Bavier Avenue, Windsor, VT
1.21
Single-Family Home
$256,500
11/14/25
3
1
1,232
74 Union Street, Windsor, VT
1.29
Single-Family Home
$319,000
07/23/26
4
2
2,142
5 Clough Avenue, Windsor, VT
1.42
Single-Family Home
$60,000
12/18/25
3
1
1,392

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
127 Mountains Edge Road #210, Brownsville, VT 05037
0.51
$323,500
3
3
1,605
Off Market
000 Marton Road, Windsor, VT 05089
0.55
$125,000
-
-
-
For Sale
1956 Rush Meadow Road, Reading, VT 05062
0.56
$950,000
Studio
-
1,757
For Sale
493 County Road #190000.493, Windsor, VT 05089
0.88
$278,400
2
1.5
975
Off Market
807 County Road, Windsor, VT 05089
0.93
$165,000
1
1
384
Off Market
672 County Road, Windsor, VT 05089
0.98
$351,700
3
2
1,500
Off Market
42 Elm Street, Windsor, VT 05089
1.03
$286,700
3
2
1,264
Off Market
18 County Road, Windsor, VT 05089
1.04
$346,600
3
2
1,400
Off Market
1471 County Road, Windsor, VT 05089
1.06
$300,200
4
2.5
2,196
Off Market
16 Day Street, Windsor, VT 05089
1.05
$94,900
2
1
660
Recently Sold
1 Dorrance Street, Windsor, VT 05089
1.09
$315,000
2
1.5
1,649
Recently Sold
21 Cherry Street, Windsor, VT 05089
1.09
$242,900
2
2
1,354
Off Market

Local Information

  • Map ViewExplore the area around 257 Herbert Hill Rd.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
32.9 acre lot

About this House

This single-family home is located at 257 Herbert Hill Rd, Windsor, VT. 257 Herbert Hill Rd is in Windsor, VT and in ZIP code 05089. This property has a lot size of 32.90 acres.
257 Herbert Hill Rd, Windsor, VT 05089 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $519,700, with a rent estimate of $3,103/month.

Home Details for 257 Herbert Hill Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 32.90 acres

Price and Tax history

YearProperty taxTax assessment
2025
$11,880
$461,750
Home facts updated by county records

Market trends in Windsor

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
3MoM

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 257 Herbert Hill Rd

  • What is 257 Herbert Hill Rd estimated to be worth?
    Trulia's estimated value for 257 Herbert Hill Rd in Windsor, VT is $519,700.
  • 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.
  • What are the closest schools to 257 Herbert Hill Rd?
    The closest schools to 257 Herbert Hill Rd in Windsor, VT are Albert Bridge School (West Windsor) (Pre-K/Elementary), Windsor School (K-12, rated 4/10).
  • How big is the lot at 257 Herbert Hill Rd?
    The lot at 257 Herbert Hill Rd in Windsor, VT is about 32.9 acres.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 257 Herbert Hill Rd

Skip to last item
Skip to first item

Homes for sale near 257 Herbert Hill Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item