Is parking easy in Stockbridge, VT?

As of early 2026, 100% of users say parking is easy

Is Stockbridge, VT dog-friendly?

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

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

As of early 2026, 100% of users say they plan to stay for at least 5 years

Does Stockbridge, VT show holiday spirit?

As of early 2026, 100% of users say there's holiday spirit

Are yards well-kept in Stockbridge, VT?

As of early 2026, 100% of users say yards are well-kept

Would people walk alone at night in Stockbridge, VT?

As of early 2026, 100% of users say people would walk alone at night

Is there wildlife in Stockbridge, VT?

As of early 2026, 100% of users say there's wildlife

Is a car needed in Stockbridge, VT?

As of early 2026, 100% of users say car is needed

Are neighbors friendly in Stockbridge, VT?

As of early 2026, 80% of users say neighbors are friendly

Is Stockbridge, VT quiet?

As of early 2026, 50% of users say it's quiet

Do kids play outside in Stockbridge, VT?

As of early 2026, 50% of users say kids play outside

Are there community events in Stockbridge, VT?

As of early 2026, 50% of users say there are community events

What is the price history for 259-05089 259?

259-05089 259 in Windsor, VT last sold for $53,000 in February 2005.

Is Windsor a buyer's or seller's market?

Windsor is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 259-05089 259?

The closest schools to 259-05089 259 in Windsor, VT are Barstow Memorial School (Pre-K/Elementary/Middle, rated 6/10), Stafford Technical Center (High), Stockbridge Central School (Pre-K/Elementary).

How big is the lot at 259-05089 259?

The lot at 259-05089 259 in Windsor, VT is about 2.5 acres .

OFF MARKET

259-05089 259
Windsor, VT 05089

Studio

Studio

(on 2.50 acres)

Local Information

Map ViewExplore the area around 259-05089 259.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

2.5 acres

About this House

This single-family home is located at 259-05089 259, Windsor, VT. 259-05089 259 is in Windsor, VT and in ZIP code 05089. This property has a lot size of 2.50 acres.

259-05089 259, Windsor, VT 05089 is a studio single-family home. It last sold for $53,000 on Feb 25, 2005. It is currently off market. The Trulia Estimate rent is $3,002/month.

Home Details for 259-05089 259

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 2.50 acres

Price History for 259-05089 259

Date	Price	Event	Source
02/25/2005	$53,000	Sold	N/A
Recording Date 02/25/2005 Contract Date 02/22/2005 County Transfer Tax N/A Total Transfer Tax $663

Market trends in Stockbridge

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	$9,600

Home facts updated by county records

Comparable Sales for 259-05089 259

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
681 South Hill Road, Pittsfield, VT	0.49	Single-Family Home	$2,150,000	04/03/26	3	4.5	4,671
161 Graysville Drive, Pittsfield, VT	0.72	Single-Family Home	$675,000	05/20/26	3	2.5	1,936
620 Route 100, Pittsfield, VT	1.21	Single-Family Home	$25,000	08/11/25		-	-
436 River View Trail, Pittsfield, VT	1.37	Single-Family Home	$810,000	09/05/25	3	2	3,635
26 Fiddlehead Lane, Pittsfield, VT	1.68	Single-Family Home	$550,000	10/24/25	3	1.5	1,512
18 Cricket Hill Rd, Killington, VT	2.68	Single-Family Home	$40,000	09/26/25		-	-
30 Ridge Road, Killington, VT	2.67	Single-Family Home	$550,000	06/03/26	5	2	1,738
430 Hawk Mountain Road, Pittsfield, VT	2.94	Single-Family Home	$575,000	01/14/26	3	3.5	2,404
32 Forsha Rd, Pittsfield, VT	3.29	Single-Family Home	$139,500	07/09/26		-	-
520 Barrows Towne Road, Killington, VT	3.09	Single-Family Home	$1,275,000	06/12/26	3	4.5	2,867

Nearby homes

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

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SOLD
DEC 30, 2025
$155,000
Lot 10 South Hill Road,
Stockbridge, VT 05772
PrimeMLS, Closed
OFF MARKET
Est. $693,600
3 bd
3 ba
2,756 sqft
853 South Hill Road,
Pittsfield, VT 05762
PrimeMLS, Closed
OFF MARKET
Lot 10-088 Old Log Road,
Stockbridge, VT 05772
PrimeMLS, Closed
SOLD
APR 3, 2026
$2,150,000
3 bd
4.5 ba
4,671 sqft
681 South Hill Road,
Pittsfield, VT 05762
PrimeMLS, Closed
OFF MARKET
905 South Hill Road,
Stockbridge, VT 05772
PrimeMLS, Closed
SOLD
MAY 20, 2026
$675,000
3 bd
2.5 ba
1,936 sqft
161 Graysville Drive,
Pittsfield, VT 05762
PrimeMLS, Closed
OFF MARKET
Est. $234,700
3 bd
1 ba
1,188 sqft
1087 Route 100,
Pittsfield, VT 05762
PrimeMLS, Closed
OFF MARKET
Est. $429,200
2 bd
1 ba
2,128 sqft
2074 Route 100,
Pittsfield, VT 05762
PrimeMLS, Closed
OFF MARKET
Lot 1-25 Madison Brook Lane,
Stockbridge, VT 05772
PrimeMLS, Closed
OFF MARKET
Lot 1-26 Madison Brook Lane #1-26,
Stockbridge, VT 05772
PrimeMLS, Closed
OFF MARKET
1-26 Madison Brook Lane #1-26,
Stockbridge, VT 05772
PrimeMLS, Closed
OFF MARKET
Est. $159,200
1 bd
1 ba
510 sqft
2358 Route 100 Road #201,
Pittsfield, VT 05762
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 259-05089 259.

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 Stockbridge

At least 1 Trulia users voted on each feature.

100 % Say parking is easy
100 % Say it's dog friendly
100 % Say they plan to stay for at least 5 years
100 % Say there's holiday spirit
100 % Say yards are well-kept
100 % Say people would walk alone at night
100 % Say there's wildlife
100 % Say car is needed
80 % Say neighbors are friendly
50 % Say it's quiet
50 % Say kids play outside
50 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Dlugosz1
Resident
2y ago
"On VAST trail which gives access via snowmobile to neighborhood and restaurants gas stations and other areas"
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LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 259-05089 259

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3.82 ACRES
$950,000
3 bd
3.5 ba
3,807 sqft
91 Bombadil Path,
Pittsfield, VT 05762
PrimeMLS, Active
0.9 ACRES
$575,000
5 bd
3 ba
2,384 sqft
89 Townsend Brook Road,
Pittsfield, VT 05762
PrimeMLS, Active
1.3 ACRES
$619,900
3 bd
1 ba
1,692 sqft
221 Fiddlehead Lane,
Pittsfield, VT 05762
PrimeMLS, Active
2.6 ACRES
$1,395,000
3 bd
3.5 ba
3,248 sqft
58 Knoll Drive,
Killington, VT 05751
PrimeMLS, Active
10.2 ACRES
$1,250,000
4 bd
4.5 ba
6,324 sqft
838 Cricket Hill Road,
Killington, VT 05751
PrimeMLS, Active
1.23 ACRES
$629,000
4 bd
3 ba
1,772 sqft
303 Winding Way,
Killington, VT 05751
PrimeMLS, Active
5 ACRES
$979,000
4 bd
3.5 ba
3,380 sqft
243 Cricket Hill Road,
Killington, VT 05751
PrimeMLS, Active
NEW - 14 HRS AGO
1.1 ACRES
$748,000
3 bd
2 ba
2,284 sqft
176 Doubleday Hill Road,
Killington, VT 05751
PrimeMLS, Active
COMING SOON 8/10
61.3 ACRES
$695,000
4 bd
1 ba
1,816 sqft
340 Upper Michigan Road,
Pittsfield, VT 05762
PrimeMLS, Coming Soon
1 ACRE
$850,000
3 bd
2.5 ba
3,000 sqft
1354 State Route 100,
Stockbridge, VT 05772
Continental Real Estate Group, Inc.
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Off Market Homes Near 259-05089 259

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SOLD
JUL 17, 2026
$696,500
5 bd
3 ba
2,504 sqft
165 Silver Spring Hill Road,
Pittsfield, VT 05762
PrimeMLS, Closed
SOLD
JUL 9, 2026
$139,500
32 Forsha Rd,
Pittsfield, VT 05762
SOLD
JUL 9, 2026
$72,500
300 Cahill Rd,
Pittsfield, VT 05762
SOLD
JUN 12, 2026
$1,275,000
3 bd
4.5 ba
2,867 sqft
520 Barrows Towne Road,
Killington, VT 05751
PrimeMLS, Closed
SOLD
JUN 3, 2026
$550,000
5 bd
2 ba
1,738 sqft
30 Ridge Road,
Killington, VT 05751
PrimeMLS, Closed
SOLD
JUN 1, 2026
$149,999
00 Blackmer Boulevard,
Stockbridge, VT 05772
PrimeMLS, Closed
SOLD
MAY 20, 2026
$675,000
3 bd
2.5 ba
1,936 sqft
161 Graysville Drive,
Pittsfield, VT 05762
PrimeMLS, Closed
SOLD
APR 23, 2026
$1,300,000
832 Route 100,
Killington, VT 05751
SOLD
APR 17, 2026
$1,300,000
3 bd
2.5 ba
3,067 sqft
832 US Route 100N,
Killington, VT 05751
PrimeMLS, Closed
SOLD
APR 14, 2026
$381,000
2 bd
1 ba
1,092 sqft
1782 Blackmer Boulevard,
Stockbridge, VT 05772
PrimeMLS, Closed
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Windsor
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Frequently asked questions about 259-05089 259

What is the price history for 259-05089 259?
259-05089 259 in Windsor, VT last sold for $53,000 in February 2005.
Is Windsor a buyer's or seller's market?
Windsor is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 259-05089 259?
The closest schools to 259-05089 259 in Windsor, VT are Barstow Memorial School (Pre-K/Elementary/Middle, rated 6/10), Stafford Technical Center (High), Stockbridge Central School (Pre-K/Elementary).
How big is the lot at 259-05089 259?
The lot at 259-05089 259 in Windsor, VT is about 2.5 acres.

259-05089 259
Windsor, VT 05089