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

35 Main St
Windsor, VT 05089

3 Beds
2.5 Baths
2,586 sqft (on 0.26 acres)

$359,800

Trulia Estimate

as of Jul 13, 2026

$359,800

Trulia Estimate

as of Jul 13, 2026

3 Beds

2.5 Baths

2,586 sqft

(on 0.26 acres)

Local Information

Map ViewExplore the area around 35 Main St.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This stunning Gothic Revival home in the heart of downtown Windsor is seeking new owners to enjoy it just as much as these owners have. It's been lovingly cared for, with new heating systems, extensive plumbing and electrical work, replacement windows and roof updates as well. 35 Main Street welcomes you with a charm and elegance of the period; tin ceilings, built ins, and exquisite exterior architecture, but will leave you feeling comfortable knowing that it does not need complete updating. Explore the facets of this home, enjoy the beautiful kitchen, take in the landscaping this Spring, and relish in the fact that you can walk to the park, the downtown, and are still only minutes to I-91.

35 Main St, Windsor, VT 05089 is a 3 bedroom, 3 bathroom, 2,586 sqft single-family home built in 1850. It last sold for $205,000 on Aug 2, 2019. It is currently off market. The Trulia Estimate is $359,800, with a rent estimate of $3,103/month.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 35 Main St

Interior Features
Heating & Cooling Heating: Stove, Gas, Oil, Wood PelletHeating Fuel: Stove
Interior Details Types of Rooms: Walk In Closet, Dining Room, Family Room
Appliances & Utilities DryerRefrigeratorWasher
Levels, Entrance, & Accessibility Floors: Softwood, Carpet

Exterior Features
Exterior Home Features Roof: Asphalt, Slate
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1850
Property Type / Style Property Type: Single Family HomeArchitecture: Queen Anne / Victorian

Lot Information
Lot Area: 0.26 acres

Price History for 35 Main St

Date	Price	Event	Source
08/02/2019	$205,000	Sold	PrimeMLS #4733147
Recording Date 08/02/2019 County Transfer Tax N/A Total Transfer Tax N/A
04/17/2014	$170,000	Sold	N/A
Recording Date 04/17/2014 Contract Date 04/15/2014 County Transfer Tax N/A Total Transfer Tax N/A
02/06/2001	$44,500	Sold	N/A
Recording Date 02/06/2001 County Transfer Tax N/A Total Transfer Tax $223

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	$302,160

Home facts updated by county records

Comparable Sales for 35 Main St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
9 Main Street, Windsor, VT	0.12	Single-Family Home	$200,001	08/28/25	4	1.5	2,310
31 Maple Street, Windsor, VT	0.58	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
70-74 State Street, Windsor, VT	0.30	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
14 Central Street, Windsor, VT	0.31	Single-Family Home	$210,000	08/06/25	1	1.5	1,056
66 Union Street, Windsor, VT	0.60	Single-Family Home	$219,000	09/02/25	3	2	1,743
10 McKenzie Drive, Windsor, VT	0.59	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
32 Clough Avenue, Windsor, VT	0.72	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
33 Central St, Windsor, VT	0.40	Single-Family Home	$35,000	09/08/25	3	2	1,436
68 Jarvis Street, Windsor, VT	0.48	Single-Family Home	$165,000	01/23/26	3	1	1,602
51 Central St, Windsor, VT	0.49	Single-Family Home	$33,500	04/30/26	3	2	1,550

Nearby homes

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

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OFF MARKET
Est. $540,100
4 bd
3 ba
3,024 sqft
29 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $452,400
4 bd
2 ba
3,146 sqft
25 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $897,500
9 bd
8.5 ba
6,232 sqft
26 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $222,200
3 bd
1 ba
1,248 sqft
19 Coolidge Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $315,200
4 bd
1.5 ba
2,310 sqft
9 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
AUCTION
0.48 ACRES
$510,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
OFF MARKET
Est. $401,700
6 bd
5 ba
3,176 sqft
40 Village Green,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $409,000
3 bd
1.5 ba
2,273 sqft
18 Pine Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 5, 2026
$425,000
3,700 sqft
64 State Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $283,200
4 bd
1.5 ba
2,116 sqft
43 River Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $342,900
3 bd
1.5 ba
1,700 sqft
25 Hemlock Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $355,100
5 bd
4 ba
4,096 sqft
108 Main Street,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 35 Main St.

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."
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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
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 35 Main St

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AUCTION
0.48 ACRES
$510,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
11 ACRES
$575,000
4 bd
3 ba
2,229 sqft
511 Route 12A,
Cornish, NH 03745
PrimeMLS, Active
$225,000
3 bd
1 ba
1,095 sqft
24 Cherry Street,
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
5.25 ACRES
$725,000
3 bd
2 ba
2,618 sqft
21 Squag City Road,
Cornish, NH 03745
PrimeMLS, Active
1.22 ACRES
$413,900
4 bd
2.5 ba
2,888 sqft
273 Route 5 North,
Windsor, VT 05089
PrimeMLS, Active
1.2 ACRES
$239,900
1 bd
1 ba
570 sqft
23 CHASE HILL Road,
Cornish, NH 03745
PrimeMLS, Active
6.8 ACRES
$299,000
2 bd
1 ba
1,152 sqft
466 Estey Lane,
Windsor, VT 05089
PrimeMLS, Active
$110,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
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
See more homes for sale in
Windsor
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