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

What is 149 Main Street estimated to be worth?

Trulia's estimated value for 149 Main Street in Windsor, VT is $266,700 .

What is the price history for 149 Main Street?

149 Main Street in Windsor, VT last sold for $110,000 in June 2024.

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 .

Does 149 Main Street have air conditioning?

Yes, 149 Main Street in Windsor, VT has air conditioning.

Does 149 Main Street have laundry facilities?

Yes, 149 Main Street in Windsor, VT has laundry facilities.

OFF MARKET

Listed by Amy Messina, Town and Country Realty, (802) 674-6311 . Bought with KW Vermont Woodstock

149 Main Street
Windsor, VT 05089

2 Beds
2.5 Baths
2,009 sqft

$266,700

Trulia Estimate

as of Aug 11, 2026

$266,700

Trulia Estimate

as of Aug 11, 2026

2 Beds

2.5 Baths

2,009 sqft

Local Information

Map ViewExplore the area around 149 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

1795

Living Area

2,009 sqft

Price/Sqft

$133

Parking

Garage

Last check for updates: about 12 hours ago

Listed by Amy Messina

Town and Country Realty, (802) 674-6311

Bought with: Evan Russell, KW Vermont Woodstock, (802) 654-8500

Source: PrimeMLS, MLS#4986683

About this House

Behind the gated picket fence, is a 1795 dwelling waiting to be restored to its former beauty. Beautiful wooden beams and wood floors. Upon entering the dwelling, there is a good sized living room on the left, and bedroom to the right. There are rooms in the back of the first floor [including a ½ bath] which potentially could be converted a den or into a large kitchen with a dining area which would overlook the back deck, lawn and plantings. The second floor includes a kitchen, one bedroom, and a full bath with a tub. The lower level includes closet/storage space, two large rooms which could be completely finished for a family room, a playroom, or for additional storage. Walking out of the lower level, takes you onto a good-sized deck for relaxing, and outdoor dining. At the far back of the lawn, which also has plantings, is the garage which has room for a small workshop. The property is walking distance to restaurants, shops and banks and a short distance to a shopping center. License To Sell in place. If you are thinking of home ownership, appreciate older homes, with character and charm, consider this opportunity.

149 Main Street, Windsor, VT 05089 is a 2 bedroom, 3 bathroom, 2,009 sqft single-family home built in 1795. It last sold for $110,000 on Jun 26, 2024 (30% below the $157,000 asking price). It is currently off market. The Trulia Estimate is $266,700, with a rent estimate of $2,732/month.

Home Details for 149 Main Street

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Concrete Floor,Full,Unfinished,Walkout,Interior Access,Exterior Entry,Basement Stairs,Interior EntryNumber of Rooms: 8
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 2009 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Electric Cooktop, Refrigerator, Electric Water Heater, Owned Water HeaterLaundry: Laundry Hook-upsRefrigerator
Heating & Cooling Heating: Oil,Forced AirNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric Electric: Circuit Breakers, Other
Windows, Doors, Floors & Walls Flooring: Other, Wood
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Other, Wood
View No View

Exterior Features
Exterior Home Features Roof: ShingleFencing: PartialExterior: DeckFoundation: Concrete
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Right-Of-Way (ROW),On Street,Detached
Frontage Road Frontage: PublicNot on Waterfront
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 73
Finished Area Finished Area (above surface): 1165 Square FeetFinished Area (below surface): 844 Square Feet

Property Information
Year Built Year Built: 1795
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building Construction Materials: Wood FrameNot a New Construction
Property Information Usage of Home: Residential

Price & Status
Price List Price: $157,000
Status Change & Dates Possession Timing: Close Of Escrow

Location
Direction & Address City: Windsor
School Information Elementary School: Windsor State Street SchoolHigh School: Windsor High School

Building
Building Area Building Area: 2009 Square Feet

Lot Information
Lot Area: 9583.2 sqft

Miscellaneous
BasementMls Number: 4986683Above Grade Unfinished Area: 1165Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price History for 149 Main Street

Date	Price	Event	Source
06/26/2024	$110,000	Sold	PrimeMLS #4986683
Recording Date 06/26/2024 County Transfer Tax N/A Total Transfer Tax N/A
03/29/2024	$157,000	PriceChange	PrimeMLS #4986683
Price Change $5,500 (-3%)
03/03/2024	$162,500	Listed For Sale	PrimeMLS #4986683

08/01/2003	$55,000	Sold	N/A
Recording Date 08/01/2003 Contract Date 07/31/2003 County Transfer Tax N/A Total Transfer Tax $275

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	$158,180

Home facts updated by county records

Comparable Sales for 149 Main Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
31 Maple Street, Windsor, VT	0.21	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
70-74 State Street, Windsor, VT	0.29	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
10 McKenzie Drive, Windsor, VT	0.30	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
74 Union Street, Windsor, VT	0.43	Single-Family Home	$319,000	07/23/26	4	2	2,142
68 Jarvis Street, Windsor, VT	0.22	Single-Family Home	$165,000	01/23/26	3	1	1,602
66 Union Street, Windsor, VT	0.39	Single-Family Home	$219,000	09/02/25	3	2	1,743
32 Clough Avenue, Windsor, VT	0.40	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
9 Main Street, Windsor, VT	0.52	Single-Family Home	$200,001	08/28/25	4	1.5	2,310

Nearby homes

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

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OFF MARKET
Est. $243,900
3 bd
1 ba
1,331 sqft
159 Marcy Court,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $218,500
3,500 sqft
9 Durkee Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $219,000
1 bd
1.5 ba
1,056 sqft
14 Central Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $346,000
5 bd
4 ba
4,096 sqft
108 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
FOR SALE
$229,000
2 bd
1 ba
1,008 sqft
29 National Street,
Windsor, VT 05089
PrimeMLS, Active
SOLD
JAN 23, 2026
$165,000
3 bd
1 ba
1,602 sqft
68 Jarvis Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $366,600
4 bd
4.5 ba
3,990 sqft
30 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $245,500
2 ba
2,662 sqft
3-5 Foster Avenue,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
JUN 10, 2026
$139,000
1 bd
1 ba
768 sqft
38 Jarvis Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $222,900
3 bd
1.5 ba
1,900 sqft
31 Maple Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $277,800
2,662 sqft
36 River Street,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 149 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
$1,895/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
92 Cedar Hill Dr #f320a52c6,
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
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
Take a look

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Homes for sale near 149 Main Street

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0.48 ACRES
$500,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
$350,000
2 bd
1.5 ba
1,092 sqft
143 Ascutney 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
$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
$99,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
Windsor, VT 05089
PrimeMLS, Active
2.51 ACRES
$279,000
2 bd
1 ba
783 sqft
15 Rt. 5 North,
Windsor, VT 05089
PrimeMLS, Active
3.2 ACRES
$574,900
4 bd
3 ba
3,200 sqft
84 Old Barn Lane,
West Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 149 Main Street

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SOLD
AUG 7, 2026
$226,000
3 bd
1 ba
2,088 sqft
4 Bavier Avenue,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
AUG 7, 2026
$273,000
3 bd
1 ba
1,008 sqft
61 Kennedy Drive,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
JUL 24, 2026
$300,000
3 bd
3 ba
1,594 sqft
70 Mountains Edge Road #606,
Brownsville, VT 05037
PrimeMLS, Closed
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
JUN 24, 2026
$290,000
3 bd
2.5 ba
1,614 sqft
127 Mountains Edge Road #211,
Brownsville, VT 05037
PrimeMLS, Closed
See more homes for sale in
Windsor
Take a look

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Frequently asked questions about 149 Main Street

What is 149 Main Street estimated to be worth?
Trulia's estimated value for 149 Main Street in Windsor, VT is $266,700.
What is the price history for 149 Main Street?
149 Main Street in Windsor, VT last sold for $110,000 in June 2024.
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.
Does 149 Main Street have air conditioning?
Yes, 149 Main Street in Windsor, VT has air conditioning.
Does 149 Main Street have laundry facilities?
Yes, 149 Main Street in Windsor, VT has laundry facilities.

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 2026-08-10 14:54:39 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.

149 Main Street
Windsor, VT 05089

$266,700

$266,700