Is Windsor, VT dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Are yards well-kept in Windsor, VT?

As of early 2026, 92% of users say yards are well-kept

Is Windsor, VT walkable to grocery stores?

As of early 2026, 91% of users say it's walkable to grocery stores

Is a car needed in Windsor, VT?

As of early 2026, 83% of users say car is needed

Is Windsor, VT walkable to restaurants?

As of early 2026, 80% of users say it's walkable to restaurants

Would people walk alone at night in Windsor, VT?

As of early 2026, 69% of users say people would walk alone at night

Does Windsor, VT show holiday spirit?

As of early 2026, 64% of users say there's holiday spirit

Do kids play outside in Windsor, VT?

As of early 2026, 64% of users say kids play outside

Does Windsor, VT have sidewalks?

As of early 2026, 64% of users say there are sidewalks

Are the streets well-lit in Windsor, VT?

As of early 2026, 64% of users say streets are well-lit

Is there wildlife in Windsor, VT?

As of early 2026, 60% of users say there's wildlife

Is parking easy in Windsor, VT?

As of early 2026, 60% of users say parking is easy

Is Windsor, VT quiet?

As of early 2026, 58% of users say it's quiet

Are neighbors friendly in Windsor, VT?

As of early 2026, 52% of users say neighbors are friendly

Do residents of Windsor, VT plan to stay at least 5 years?

As of early 2026, 36% of users say they plan to stay for at least 5 years

Are there community events in Windsor, VT?

As of early 2026, 20% of users say there are community events

OFF MARKET

61 Herbert Hill Rd
Windsor, VT 05089

3 Beds
3 Baths
2,088 sqft (on 33 acres)

$630,400

Trulia Estimate

as of Jul 13, 2026

$630,400

Trulia Estimate

as of Jul 13, 2026

3 Beds

3 Baths

2,088 sqft

(on 33 acres)

Local Information

Map ViewExplore the area around 61 Herbert Hill Rd.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

What a gem!This impeccably maintained home is a pleasure to see! Very light, bright and well laid out. Main living area includes a fantastic new kitchen, opening onto family/dining room, a large living room with fireplace overlooking an over-sized deck, with hardwood floors throughout. The upper level includes a spacious master suite overlooking Kimball Brook which borders the property and and a luxurious full bath. There are two more bedrooms with a private bath also on this level. The lower level is a walk-out and ready to finish. Wonderfully landscaped with the brook right here. Private, yet close to town. Come take a look.

61 Herbert Hill Rd, Windsor, VT 05089 is a 3 bedroom, 3 bathroom, 2,088 sqft single-family home built in 1989. It last sold for $276,500 on Mar 2, 2016. It is currently off market. The Trulia Estimate is $630,400, with a rent estimate of $3,469/month.

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 61 Herbert Hill Rd

Interior Features
Heating & Cooling Heating: Baseboard, OilHeating Fuel: Baseboard
Interior Details Additional StorageTypes of Rooms: Dining RoomStorageCeiling Fan
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility Floors: Carpet, Hardwood, Linoleum Vinyl

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: Wood
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1989
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Lot Information
Lot Area: 33.00 acres

Price History for 61 Herbert Hill Rd

Date	Price	Event	Source
03/02/2016	$276,500	Sold	N/A
Recording Date 03/02/2016 Contract Date 02/26/2016 County Transfer Tax N/A Total Transfer Tax $3
11/06/2015	$279,000	Listed For Sale	Agent Provided

06/07/2012	$260,000	Sold	N/A
Recording Date 06/07/2012 Contract Date 06/05/2012 County Transfer Tax N/A Total Transfer Tax N/A
04/18/2012	$279,000	Listed For Sale	Agent Provided

12/02/2005	$264,200	Sold	N/A
Recording Date 12/02/2005 Contract Date 11/29/2005 County Transfer Tax N/A Total Transfer Tax $2,553

Market trends in Windsor

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Property Tax and Assessment

Year	2024
Tax
Assessment	$411,430

Home facts updated by county records

Comparable Sales for 61 Herbert Hill Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
672 County Road, Windsor, VT	0.95	Single-Family Home	$340,000	09/05/25	3	2	1,500
1471 County Road, Windsor, VT	1.12	Single-Family Home	$290,000	08/25/25	4	2.5	2,196
1 Dorrance Street, Windsor, VT	0.95	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
66 Union Street, Windsor, VT	1.19	Single-Family Home	$219,000	09/02/25	3	2	1,743
32 Clough Avenue, Windsor, VT	1.30	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
3 Cherry Street, Windsor, VT	1.05	Single-Family Home	$259,000	05/01/26	3	1	1,176
6 Kiniry St, Windsor, VT	0.99	Single-Family Home	$176,000	07/28/25	3	1	1,400
21 Bavier Avenue, Windsor, VT	1.07	Single-Family Home	$256,500	11/14/25	3	1	1,232
10 McKenzie Drive, Windsor, VT	1.30	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
2787 Route 44, Windsor, VT	1.61	Single-Family Home	$278,000	07/21/25	3	1.5	1,936

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $327,000
3 bd
3 ba
1,605 sqft
127 Mountains Edge Road #210,
Brownsville, VT 05037
PrimeMLS, Closed
OFF MARKET
Est. $285,600
2 bd
1.5 ba
975 sqft
493 County Road #190000.493,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $283,700
3 bd
2 ba
1,264 sqft
42 Elm Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
DEC 4, 2025
$94,900
2 bd
1 ba
660 sqft
16 Day Street,
Windsor, VT 05089
PrimeMLS, Closed
FOR SALE
$225,000
3 bd
1 ba
1,095 sqft
24 Cherry Street,
Windsor, VT 05089
PrimeMLS, Active
SOLD
NOV 21, 2025
$315,000
2 bd
1.5 ba
1,649 sqft
1 Dorrance Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $339,400
3 bd
2 ba
1,400 sqft
18 County Road,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $248,900
2 bd
2 ba
1,354 sqft
21 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $167,300
1 bd
1 ba
384 sqft
807 County Road,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
OCT 6, 2025
$40,000
2 bd
1 ba
434 sqft
138 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $349,800
3 bd
2 ba
1,500 sqft
672 County Road,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $208,200
2 bd
2 ba
1,439 sqft
146 Ascutney Street,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 61 Herbert Hill Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
Resident
5y ago
"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
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Apartments for Rent

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NEW - 2 DAYS AGO
$1,325/mo
1 bd
1 ba
9 State St #3C,
Windsor, VT 05089
$1,350/mo
1 bd
1 ba
24 State St #1,
Windsor, VT 05089
$1,300/mo
1 bd
1 ba
2326 US Route 5 N #1A,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,450/mo
2 bd
1 ba
55 River St #B,
Windsor, VT 05089
$1,136/mo
Studio
1 ba
18 Union St #C,
Windsor, VT 05089
$1,500 - $1,700/mo
1-2 bd
1 ba
360 Tecumseh Road West | Tecumseh Rd W,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
289 County Rd #f320a52c6,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
65 State St #f320a52c6,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
APPLY INSTANTLY
PET FRIENDLY
$1,495/mo
1 bd
1 ba
51 River St #1,
Windsor, VT 05089
See more homes for rent in
Windsor
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Homes for sale near 61 Herbert Hill Rd

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$225,000
3 bd
1 ba
1,095 sqft
24 Cherry Street,
Windsor, VT 05089
PrimeMLS, Active
6.8 ACRES
$299,000
2 bd
1 ba
1,152 sqft
466 Estey Lane,
Windsor, VT 05089
PrimeMLS, Active
4.96 ACRES
$1,399,000
4 bd
3.5 ba
4,000 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Active
11 ACRES
$575,000
4 bd
3 ba
2,229 sqft
511 Route 12A,
Cornish, NH 03745
PrimeMLS, Active
AUCTION
0.48 ACRES
$510,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
3.2 ACRES
$599,000
4 bd
3 ba
3,200 sqft
84 Old Barn Lane,
West Windsor, VT 05089
PrimeMLS, Active
10.27 ACRES
$645,000
4 bd
2.5 ba
2,515 sqft
221 Dunkel Road,
West Windsor, VT 05089
PrimeMLS, Active
1.22 ACRES
$413,900
4 bd
2.5 ba
2,888 sqft
273 Route 5 North,
Windsor, VT 05089
PrimeMLS, Active
5.51 ACRES
$1,345,000
7 bd
5 ba
5,774 sqft
310 Pierce Hill Road,
Windsor, VT 05089
PrimeMLS, Active
26.72 ACRES
$1,325,000
4 bd
2 ba
2,554 sqft
325 Cemetery Road,
Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look