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

Listed by Linda Benoit, Highland Realty, (802) 780-7535 . Bought with KW Vermont Woodstock

9 Main Street
Windsor, VT 05089

4 Beds
1.5 Baths
2,310 sqft (on 0.40 acres)

$317,800

Trulia Estimate

as of Aug 6, 2026

Est. Refi. Payment $2,248/mo*

Refinance Your Home

$317,800

Trulia Estimate

as of Aug 6, 2026

Est. Refi. Payment $2,248/mo*

Refinance Your Home

4 Beds

1.5 Baths

2,310 sqft

(on 0.40 acres)

Local Information

Map ViewExplore the area around 9 Main Street.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1890

Lot Size

0.4 acres

Living Area

2,310 sqft

Price/Sqft

$138

Parking

Garage

Last check for updates: about 6 hours ago

Listed by Linda Benoit

Highland Realty, (802) 780-7535

Bought with: Allison Griep, KW Vermont Woodstock, (802) 654-8500

Source: PrimeMLS, MLS#5052179

About this House

A Grand Old Home Full of Character and Potential What a beauty this home once was—and can be again! Brimming with historic charm, this spacious residence is just waiting for someone to restore it to its full glory. From the high ceilings and rich pecan woodwork to the elegant crown moldings and soapstone countertops, the original details create a timeless backdrop for your vision. The main level features a classic layout with first-floor laundry, a charming pantry, and generous living spaces perfect for modern living or a thoughtful restoration. Located within walking distance of local shops and restaurants, you’ll enjoy the convenience of in-town living with the tranquility of a quiet neighborhood. Just a short drive to the Upper Valley and close to several ski areas, this property is perfectly situated for year-round enjoyment. If you’re looking for a home with history, character, and incredible potential—this is it. And don't forget to see the hidden yard setback behind the garage. Lots of room for gardening, firepit, playset, pool.....whatever you desire! Property is in the First Look Program - offers from primary home buyers only for the first 30 days.

9 Main Street, Windsor, VT 05089 is a 4 bedroom, 2 bathroom, 2,310 sqft single-family home built in 1890. It last sold for the $199,900 asking price on Aug 28, 2025. It is currently off market. The Trulia Estimate is $317,800, with a rent estimate of $3,252/month.

Home Details for 9 Main Street

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Unfinished,Interior EntryNumber of Rooms: 8
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 2310 Square Feet
Appliances & Utilities Utilities: Cable Available, Propane, Phone Available
Heating & Cooling Heating: Propane,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Propane
Gas & Electric Electric: Circuit Breakers
Levels, Entrance, & Accessibility Stories: 2Levels: Two
View No View

Exterior Features
Exterior Home Features Roof: Asphalt ShingleFoundation: Stone
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Paved,Driveway,Detached
Frontage Road Frontage: Public
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 78
Finished Area Finished Area (above surface): 2310 Square Feet

Property Information
Year Built Year Built: 1890
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian
Building Construction Materials: Wood Frame, Wood SidingNot a New Construction

Price & Status
Price List Price: $199,900

Location
Direction & Address City: Windsor
School Information Elementary School District: WindsorJr High / Middle School District: WindsorHigh School District: Windsor

Building
Building Area Building Area: 3450 Square Feet

Lot Information
Lot Area: 0.40 acres

Listing Info
Special Conditions: In Foreclosure

Miscellaneous
BasementMls Number: 5052179Above Grade Unfinished Area: 2310Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 1140Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price History for 9 Main Street

Date	Price	Event	Source
08/28/2025	$200,001	Sold	PrimeMLS #5052179
Recording Date 08/28/2025 County Transfer Tax N/A Total Transfer Tax N/A
05/29/2025	$295,631	Sold	N/A
Recording Date 05/29/2025 Contract Date 03/13/2025 County Transfer Tax N/A Total Transfer Tax N/A
11/06/2001	$125,000	Sold	N/A
Recording Date 11/06/2001 Contract Date 11/02/2001 County Transfer Tax N/A Total Transfer Tax $813
12/13/1993	$92,000	Sold	N/A
Recording Date 12/13/1993 Contract Date 12/10/1993 County Transfer Tax N/A Total Transfer Tax $460

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	$288,010

Home facts updated by county records

Comparable Sales for 9 Main Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
74 Union Street, Windsor, VT	0.71	Single-Family Home	$319,000	07/23/26	4	2	2,142
70-74 State Street, Windsor, VT	0.37	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
31 Maple Street, Windsor, VT	0.69	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
32 Clough Avenue, Windsor, VT	0.82	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
66 Union Street, Windsor, VT	0.68	Single-Family Home	$219,000	09/02/25	3	2	1,743
68 Jarvis Street, Windsor, VT	0.60	Single-Family Home	$165,000	01/23/26	3	1	1,602
58 Morningside Drive, Windsor, VT	0.67	Single-Family Home	$395,900	11/13/25	3	1.5	1,680
10 McKenzie Drive, Windsor, VT	0.68	Single-Family Home	$271,000	11/13/25	3	1.5	1,320

Nearby homes

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

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OFF MARKET
Est. $221,500
3 bd
1 ba
1,248 sqft
19 Coolidge Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $460,400
4 bd
2 ba
3,146 sqft
25 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $541,200
4 bd
3 ba
3,024 sqft
29 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $908,400
9 bd
8.5 ba
6,232 sqft
26 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $339,200
3 bd
1.5 ba
1,700 sqft
25 Hemlock Drive,
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
FOR SALE
$442,999
3 bd
2 ba
1,961 sqft
6 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
OFF MARKET
Est. $406,700
3 bd
1.5 ba
2,273 sqft
18 Pine Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $405,400
6 bd
5 ba
3,176 sqft
40 Village Green,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $225,800
5 bd
2 ba
2,304 sqft
2460 Route 5N,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 5, 2026
$425,000
3,700 sqft
64 State Street,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 9 Main Street.

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
6y 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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$1,325/mo
1 bd
1 ba
9 State Street | 9 State St,
Windsor, VT 05089
$1,325 - $1,350/mo
1 bd
1 ba
24 State Street | 24 State St,
Windsor, VT 05089
$1,425/mo
1 bd
1 ba
112-114 State St #114A,
Windsor, VT 05089
$1,300/mo
1 bd
1 ba
2326 US Route 5 N #1A,
Windsor, VT 05089
$1,895/mo
3 bd
1 ba
8 Union St #4,
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
See more homes for rent in
Windsor
Take a look

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Homes for sale near 9 Main Street

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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
OPEN SUN, 11-1PM
11 ACRES
$575,000
4 bd
3 ba
2,229 sqft
511 Route 12A,
Cornish, NH 03745
PrimeMLS, Active
$109,000
1 bd
1 ba
504 sqft
52 Jarvis 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
NEW
OPEN SAT, 10-12PM
2.51 ACRES
$279,000
2 bd
1 ba
783 sqft
15 Rt. 5 North,
Windsor, VT 05089
PrimeMLS, Active
$99,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
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Off Market Homes Near 9 Main Street

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SOLD
JUL 27, 2026
$425,000
27 Route 12,
Hartland, VT 05048
SOLD
JUL 23, 2026
$319,000
4 bd
2 ba
2,142 sqft
74 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
JUL 14, 2026
$374,000
2 bd
2 ba
1,192 sqft
39 Parsonage Road,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
JUL 13, 2026
$175,000
3 bd
2 ba
1,527 sqft
271 Tandy Brook Rd,
Cornish, NH 03745
SOLD
JUL 6, 2026
$260,000
00 Tandy Brook Road #12,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
JUL 1, 2026
$222,030
1214 State St,
Windsor, VT 05089
SOLD
JUN 30, 2026
$200,000
245 Orchard Ln,
Windsor, VT 05089
SOLD
MAY 21, 2026
$195,000
Hotel Rd,
Brownsville, VT 05037
SOLD
MAY 15, 2026
$459,000
4 bd
1.5 ba
2,349 sqft
579 Town House Road,
Cornish, NH 03745
PrimeMLS, Closed
SOLD
MAY 7, 2026
$185,000
195 Main St,
Windsor, VT 05089
See more homes for sale in
Windsor
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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-08-06 03:33:37 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

9 Main Street
Windsor, VT 05089

$317,800

$317,800