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 5 Jacob St estimated to be worth?

Trulia's estimated value for 5 Jacob St in Windsor, VT is $296,600 .

What is the price history for 5 Jacob St?

5 Jacob St in Windsor, VT last sold for $135,000 in June 2017.

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 .

How big is the lot at 5 Jacob St?

The lot at 5 Jacob St in Windsor, VT is about 0.08 acres (3,485 sq ft).

Does 5 Jacob St have parking?

Yes, 5 Jacob St in Windsor, VT has on-site parking.

OFF MARKET

$296,600

Trulia Estimate

4 Beds
1.5 Baths
1,900 sqft

5 Jacob St, Windsor, VT 05089

Est. Refi. Payment $2,068/mo*

Refinance Your Home

Currently Off Market - Sold Jun 9, 2017 for $135,000

Home Value

Trulia Estimate

$297K

Since last month

$2K (-0.6%)

Since last year

$6K (-2.1%)

Since last sale

$163K (+120.7%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +99% in the last 10 years

Month	Estimated value
2026
August 2026	$298K
July 2026	$300K
June 2026	$309K
May 2026	$303K
April 2026	$292K
March 2026	$298K
February 2026	$288K
January 2026	$274K
2025
December 2025	$273K
November 2025	$291K
October 2025	$288K
September 2025	$301K
August 2025	$304K
July 2025	$312K
June 2025	$315K
May 2025	$312K
April 2025	$302K
March 2025	$293K
February 2025	$288K
January 2025	$289K
2024
December 2024	$293K
November 2024	$296K
October 2024	$275K
September 2024	$276K
August 2024	$271K
July 2024	$271K
June 2024	$273K
May 2024	$271K
April 2024	$258K
March 2024	$252K
February 2024	$243K
January 2024	$244K
2023
December 2023	$248K
November 2023	$250K
October 2023	$254K
September 2023	$256K
August 2023	$258K
July 2023	$260K
June 2023	$254K
May 2023	$250K
April 2023	$246K
March 2023	$240K
February 2023	$233K
January 2023	$230K
2022
December 2022	$231K
November 2022	$235K
October 2022	$236K
September 2022	$238K
August 2022	$238K
July 2022	$241K
June 2022	$240K
May 2022	$238K
April 2022	$232K
March 2022	$227K
February 2022	$220K
January 2022	$219K
2021
December 2021	$217K
November 2021	$216K
October 2021	$214K
September 2021	$212K
August 2021	$212K
July 2021	$211K
June 2021	$209K
May 2021	$202K
April 2021	$198K
March 2021	$186K
February 2021	$191K
January 2021	$191K
2020
December 2020	$185K
November 2020	$181K
October 2020	$162K
September 2020	$177K
August 2020	$175K
July 2020	$165K
June 2020	$152K
May 2020	$147K
April 2020	$147K
March 2020	$147K
February 2020	$146K
January 2020	$146K
2019
December 2019	$146K
November 2019	$145K
October 2019	$145K
September 2019	$144K
August 2019	$143K
July 2019	$142K
June 2019	$142K
May 2019	$142K
April 2019	$141K
March 2019	$133K
February 2019	$132K
January 2019	$135K
2018
December 2018	$140K
November 2018	$142K
October 2018	$142K
September 2018	$141K
August 2018	$141K
July 2018	$140K
June 2018	$140K
May 2018	$140K
April 2018	$140K
March 2018	$140K
February 2018	$139K
January 2018	$138K
2017
December 2017	$136K
November 2017	$136K
October 2017	$137K
September 2017	$137K
August 2017	$136K
July 2017	$136K
June 2017	$135K
May 2017	$143K
April 2017	$143K
March 2017	$143K
February 2017	$158K
January 2017	$137K
2016
December 2016	$137K
November 2016	$138K
October 2016	$137K
September 2016	$137K
August 2016	$149K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
66 Union Street, Windsor, VT	0.34	Single-Family Home	$219,000	09/02/25	3	2	1,743
68 Jarvis Street, Windsor, VT	0.49	Single-Family Home	$165,000	01/23/26	3	1	1,602
5 Clough Avenue, Windsor, VT	0.36	Single-Family Home	$60,000	12/18/25	3	1	1,392
31 Maple Street, Windsor, VT	0.39	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
10 McKenzie Drive, Windsor, VT	0.34	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
70-74 State Street, Windsor, VT	0.02	Single-Family Home	$115,000	12/10/25	5	3.5	4,011
74 Union Street, Windsor, VT	0.36	Single-Family Home	$319,000	07/23/26	4	2	2,142
33 Central St, Windsor, VT	0.35	Single-Family Home	$35,000	09/08/25	3	2	1,436
38 Jarvis Street, Windsor, VT	0.44	Single-Family Home	$139,000	06/10/26	1	1	768
4 Bavier Avenue, Windsor, VT	0.86	Single-Family Home	$226,000	08/07/26	3	1	2,088

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
64 State Street, Windsor, VT 05089	0.03	$425,000	Studio	-	3,700	Recently Sold
70-74 State Street, Windsor, VT 05089	0.02	$115,000	5	3.5	4,011	Recently Sold
18 Pine Street, Windsor, VT 05089	0.06	$403,700	3	1.5	2,273	Off Market
40 Village Green, Windsor, VT 05089	0.10	$395,200	6	5	3,176	Off Market
100 State Street, Windsor, VT 05089	0.12	$245,200	6	1.5	2,880	Off Market
2 Pine Street, Windsor, VT 05089	0.12	$500,000	6	4	4,933	For Sale
102-104 State Street, Windsor, VT 05089	0.13	$294,300	7	4	3,894	Off Market
108 Main Street, Windsor, VT 05089	0.22	$345,600	5	4	4,096	Off Market
14 Central Street, Windsor, VT 05089	0.27	$217,800	1	1.5	1,056	Off Market
2 Ascutney Street, Windsor, VT 05089	0.26	$314,300	3	1.5	1,364	Off Market
149 Main Street, Windsor, VT 05089	0.30	$257,300	2	2.5	2,009	Off Market
30 Union Street, Windsor, VT 05089	0.30	$365,300	4	4.5	3,990	Off Market

Local Information

Map ViewExplore the area around 5 Jacob St.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1800

Living Area

1,900 sqft

Price/Sqft

$156

About this House

Prices are starting to FALL! This home won't be on market for long.... Built in 1880, it gives you the feel and comfort of an older home, with all the modern convenience updates, including roof, windows and furnace. There are 4 bedrooms, 1.5 bathrooms, an office, a TV room, living room, dining room, and expansive kitchen with pantry. You will feel welcomed by the 3 season porch on the front, and the charm each room will offer as you stroll around on hardwood floors. Washer and dryer on the main level make for easy access, and a back door to the quaint yard with a beautiful SnowDrift Crab Apple. Time for you to make this your home sweet home!

5 Jacob St, Windsor, VT 05089 is a 4 bedroom, 2 bathroom, 1,900 sqft single-family home built in 1800. It last sold for $135,000 on Jun 9, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $296,600, with a rent estimate of $2,684/month.

Home Details for 5 Jacob St

Interior Features
Heating & Cooling Heating: OilHeating Fuel: Oil
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DishwasherRefrigerator

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Vinyl
Parking & Garage Parking Spaces: 2

Property Information
Year Built Year Built: 1800
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 3484 sqft

Price and Tax history

Date	Event	Price
Jun 9, 2017 Source: PrimeMLS #4501024	Sold	$135,000
Apr 19, 2017 Source: Agent Provided	Pending	$149,000
Mar 21, 2017 Source: Agent Provided	Listed For Sale	$149,000
Dec 1, 2016 Source: Agent Provided	ListingRemoved	$143,000
Sep 27, 2016 Source: Agent Provided	PriceChange	$143,000 Price decreased by 7%
Jun 29, 2016 Source: Agent Provided	Listed For Sale	$153,000
Dec 29, 2005 Source: N/A	Sold	$104,500
Jun 1, 2001 Source: N/A	Sold	$79,900
Jul 8, 1998 Source: N/A	Sold	$69,900

Year	Property tax	Tax assessment
2025	$5,710	$221,910

Additional Cost

Market trends in Windsor

Last updated July 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

Around this home

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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Frequently asked questions about 5 Jacob St

What is 5 Jacob St estimated to be worth?
Trulia's estimated value for 5 Jacob St in Windsor, VT is $296,600.
What is the price history for 5 Jacob St?
5 Jacob St in Windsor, VT last sold for $135,000 in June 2017.
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.
How big is the lot at 5 Jacob St?
The lot at 5 Jacob St in Windsor, VT is about 0.08 acres (3,485 sq ft).
Does 5 Jacob St have parking?
Yes, 5 Jacob St in Windsor, VT has on-site parking.