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 44 Kennedy Dr N estimated to be worth?

Trulia's estimated value for 44 Kennedy Dr N in Windsor, VT is $230,200 .

What is the price history for 44 Kennedy Dr N?

44 Kennedy Dr N in Windsor, VT last sold for $61,500 in January 1999.

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 44 Kennedy Dr N?

The lot at 44 Kennedy Dr N in Windsor, VT is about 0.24 acres (10,454 sq ft).

Does 44 Kennedy Dr N have a garage?

Yes, 44 Kennedy Dr N in Windsor, VT has a garage.

OFF MARKET

$230,200

Trulia Estimate

3 Beds
1 Bath
1,008 sqft

44 Kennedy Dr N, Windsor, VT 05089

Est. Refi. Payment $1,695/mo*

Refinance Your Home

Currently Off Market - Sold Jan 19, 1999 for $61,500

Home Value

Trulia Estimate

$230K

Since last month

$7K (+3.1%)

Since last year

$5K (+2.4%)

Since last sale

$169K (+274.3%)

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 +78% in the last 10 years

Month	Estimated value
2026
September 2026	$230K
August 2026	$223K
July 2026	$219K
June 2026	$226K
May 2026	$221K
April 2026	$216K
March 2026	$220K
February 2026	$209K
January 2026	$206K
2025
December 2025	$210K
November 2025	$220K
October 2025	$222K
September 2025	$225K
August 2025	$226K
July 2025	$242K
June 2025	$246K
May 2025	$216K
April 2025	$211K
March 2025	$204K
February 2025	$198K
January 2025	$199K
2024
December 2024	$213K
November 2024	$213K
October 2024	$205K
September 2024	$206K
August 2024	$208K
July 2024	$212K
June 2024	$211K
May 2024	$205K
April 2024	$197K
March 2024	$193K
February 2024	$178K
January 2024	$184K
2023
December 2023	$183K
November 2023	$182K
October 2023	$184K
September 2023	$188K
August 2023	$189K
July 2023	$193K
June 2023	$173K
May 2023	$196K
April 2023	$190K
March 2023	$185K
February 2023	$180K
January 2023	$179K
2022
December 2022	$180K
November 2022	$183K
October 2022	$183K
September 2022	$183K
August 2022	$183K
July 2022	$185K
June 2022	$184K
May 2022	$182K
April 2022	$175K
March 2022	$168K
February 2022	$158K
January 2022	$157K
2021
December 2021	$161K
November 2021	$161K
October 2021	$162K
September 2021	$160K
August 2021	$162K
July 2021	$165K
June 2021	$168K
May 2021	$168K
April 2021	$163K
March 2021	$145K
February 2021	$150K
January 2021	$145K
2020
December 2020	$142K
November 2020	$137K
October 2020	$129K
September 2020	$128K
August 2020	$136K
July 2020	$133K
June 2020	$131K
May 2020	$125K
April 2020	$130K
March 2020	$136K
February 2020	$135K
January 2020	$136K
2019
December 2019	$138K
November 2019	$136K
October 2019	$136K
September 2019	$139K
August 2019	$139K
July 2019	$140K
June 2019	$138K
May 2019	$138K
April 2019	$138K
March 2019	$132K
February 2019	$131K
January 2019	$127K
2018
December 2018	$128K
November 2018	$128K
October 2018	$130K
September 2018	$130K
August 2018	$130K
July 2018	$128K
June 2018	$128K
May 2018	$131K
April 2018	$129K
March 2018	$129K
February 2018	$130K
January 2018	$128K
2017
December 2017	$132K
November 2017	$127K
October 2017	$127K
September 2017	$126K
August 2017	$125K
July 2017	$127K
June 2017	$128K
May 2017	$130K
April 2017	$132K
March 2017	$130K
February 2017	$127K
January 2017	$127K
2016
December 2016	$126K
November 2016	$127K
October 2016	$128K
September 2016	$129K

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
61 Kennedy Drive, Windsor, VT	0.09	Single-Family Home	$273,000	08/07/26	3	1	1,008
2085 US Route 5 South, Windsor, VT	0.09	Single-Family Home	$327,000	09/26/25	3	1	1,560
173 Orchard Lane, Windsor, VT	1.07	Single-Family Home	$312,000	09/14/26	3	1	2,388
1118 NH Route 12A, Cornish, NH	0.59	Single-Family Home	$600,000	12/02/25	3	4	4,186
96 Dairy Lane, Windsor, VT	1.00	Single-Family Home	$400,000	12/19/25	4	2.5	2,272
16 Day Street, Windsor, VT	2.13	Single-Family Home	$94,900	12/04/25	2	1	660
21 Bavier Avenue, Windsor, VT	2.01	Single-Family Home	$256,500	11/14/25	3	1	1,232
5 Clough Avenue, Windsor, VT	2.26	Single-Family Home	$60,000	12/18/25	3	1	1,392
3 Cherry Street, Windsor, VT	2.19	Single-Family Home	$259,000	05/01/26	3	1	1,176
920 Town House Road, Cornish, NH	1.80	Single-Family Home	$355,000	10/24/25	2	1	1,092

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
59 Weston Heights, Windsor, VT 05089	0.03	$265,300	4	1	1,008	Off Market
2125 Route 5 South, Windsor, VT 05089	0.05	$255,600	3	1	1,654	Off Market
61 Kennedy Drive, Windsor, VT 05089	0.09	$273,000	3	1	1,008	Recently Sold
2085 US Route 5 South, Windsor, VT 05089	0.09	$337,600	3	1	1,560	Off Market
1528 Route 5 South, Windsor, VT 05089	0.57	$1,659,100	6	6	9,352	Off Market
1118 NH Route 12A, Cornish, NH 03745	0.59	$600,000	3	4	4,186	Recently Sold
1223 Route 5 South, Windsor, VT 05089	0.92	$132,100	3	2	1,344	Off Market
96 Dairy Lane, Windsor, VT 05089	1.00	$400,000	4	2.5	2,272	Recently Sold
1124 Route 5 S, Windsor, VT 05089	1.03	$415,100	4	4	2,656	Off Market
39 Dairy Lane, Windsor, VT 05089	1.06	$370,400	2	1.5	1,296	Off Market
173 Orchard Lane, Windsor, VT 05089	1.07	$312,000	3	1	2,388	Recently Sold
28 Bishops Loop, Windsor, VT 05089	1.09	$219,100	3	1.5	1,352	Off Market

Local Information

Map ViewExplore the area around 44 Kennedy Dr N.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1942

1,008 sqft

$228/sqft

Garage

About this House

Updated 1942 1-1/2 story Cape style with new, large covered front porch, back deck and detached garage

44 Kennedy Dr N, Windsor, VT 05089 is a 3 bedroom, 1 bathroom, 1,008 sqft single-family home built in 1942. It last sold for $61,500 on Jan 19, 1999. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $230,200, with a rent estimate of $2,449/month.

Home Details for 44 Kennedy Dr N

Interior Features
Interior Details BasementAdditional StorageNumber of Rooms: 6Types of Rooms: OfficeStorage
Heating & Cooling Heating: Baseboard, Forced Air, Gas, Wood PelletHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood, Laminate
Appliances & Utilities Cable ReadyMicrowaveRefrigerator
Windows, Doors, Floors & Walls Double Paned Windows

Exterior Features
Exterior Home Features Roof: Asphalt, MetalDeckExterior: VinylGardenLawnPorch
Parking & Garage GarageParking Spaces: 3Parking: Garage Detached, Off Street

Property Information
Year Built Year Built: 1942
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information
Lot Area: 10454 sqft

Price and Tax history

Date	Event	Price
Jan 19, 1999 Source: N/A	Sold	$61,500

Year	Property tax	Tax assessment
2025	$4,759	$184,980

Additional Cost

Market trends in Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

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 44 Kennedy Dr N

What is 44 Kennedy Dr N estimated to be worth?
Trulia's estimated value for 44 Kennedy Dr N in Windsor, VT is $230,200.
What is the price history for 44 Kennedy Dr N?
44 Kennedy Dr N in Windsor, VT last sold for $61,500 in January 1999.
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 44 Kennedy Dr N?
The lot at 44 Kennedy Dr N in Windsor, VT is about 0.24 acres (10,454 sq ft).
Does 44 Kennedy Dr N have a garage?
Yes, 44 Kennedy Dr N in Windsor, VT has a garage.