149 Main Street, Windsor, VT 05089
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

$249,200

Trulia Estimate
as of May 12, 2026
Est. Refi. Payment $1,716/mo*
Refinance Your Home

$249,200

Trulia Estimate
as of May 12, 2026
Est. Refi. Payment $1,716/mo*
Refinance Your Home
2 Beds
2.5 Baths
2,009 sqft

Homes for sale near 149 Main Street

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 5 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

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from June 27, 2024

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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

DatePriceEventSource
06/26/2024$110,000Sold
PrimeMLS #4986683
03/29/2024$157,000PriceChange
PrimeMLS #4986683
03/03/2024$162,500Listed For SalePrimeMLS #4986683
08/01/2003$55,000Sold
N/A
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Property Tax and Assessment

Year2024
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
14 Central Street, Windsor, VT
0.09
Single-Family Home
$210,000
08/06/25
1
1.5
1,056
3 Fitch Court, Windsor, VT
0.38
Single-Family Home
$229,000
06/25/25
2
2
1,665
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
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

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 9 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 92 % Say yards are well-kept

  • 90 % Say it's walkable to grocery stores

  • 83 % Say car is needed

  • 78 % Say it's walkable to restaurants

  • 67 % Say parking is easy

  • 67 % Say people would walk alone at night

  • 64 % Say streets are well-lit

  • 64 % Say it's quiet

  • 64 % Say there are sidewalks

  • 64 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 52 % Say neighbors are friendly

  • 36 % Say they plan to stay for at least 5 years

  • 20 % Say there are community events

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."
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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 2026-05-11 14:19:54 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.

Homes for rent near 149 Main Street

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Off Market Homes Near 149 Main Street

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149 Main Street, Windsor, VT 05089 is a 2 bedroom, 3 bathroom, 2,009 sqft single-family home built in 1795. This property is not currently available for sale. 149 Main Street was last sold on Jun 26, 2024 for $110,000 (30% lower than the asking price of $157,000). The current Trulia Estimate for 149 Main Street is $249,200.