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

OFF MARKET

369 Juniper Hill Rd
Windsor, VT 05089

1 Bed
1 Bath
1,354 sqft (on 2.90 acres)

$381,800

Trulia Estimate

as of Jul 12, 2026

$381,800

Trulia Estimate

as of Jul 12, 2026

1 Bed

1 Bath

1,354 sqft

(on 2.90 acres)

Local Information

Map ViewExplore the area around 369 Juniper Hill Rd.
Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Furnished spacious bedroom and shared bath and fully equipped shared kitchen. Beautiful view adjacent to Windsor town forest and close to all that the Upper Valley has to offer. All utilities and internet included. Must like the idea of community and have respect for others.

One year lease or month to month for slightly more.

369 Juniper Hill Rd, Windsor, VT 05089 is a 1 bedroom, 1 bathroom, 1,354 sqft single-family home built in 1850. It last sold for $325,000 on May 13, 2022. More recently, it was listed as a rental in March 2020 with an asking price of $650 per month. That rental listing was removed on February 27, 2021. It is currently off market. The Trulia Estimate is $381,800, with a rent estimate of $1,801/month.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 369 Juniper Hill Rd

Interior Features
Heating & Cooling Heating: Forced Air, GasHeating Fuel: Forced Air
Interior Details Types of Rooms: Dining Room
Appliances & Utilities DryerWasher
Levels, Entrance, & Accessibility Floors: Hardwood

Exterior Features
Exterior Home Features Roof: AsphaltExterior: WoodGarden
Parking & Garage Parking Space: 1Parking: Off Street

Property Information
Year Built Year Built: 1850
Property Type / Style Property Type: Single Family Home

Rental Terms, Policies & Fees
Furnished

Lot Information
Lot Area: 2.90 acres

Price History for 369 Juniper Hill Rd

Date	Price	Event	Source
05/13/2022	$325,000	Sold	PrimeMLS #4907482
Recording Date 05/13/2022 County Transfer Tax N/A Total Transfer Tax N/A
05/04/2022	$260,000	Contingent	PrimeMLS #4907482

04/29/2022	$260,000	Listed For Sale	PrimeMLS #4907482

02/27/2021		ListingRemoved	N/A

04/07/2020	$650	ListingRemoved	N/A

03/08/2020	$650	Listed For Rent	N/A

09/25/2019	$157,000	Sold	PrimeMLS #4744324
Recording Date 09/25/2019 County Transfer Tax N/A Total Transfer Tax N/A
12/01/2016	$159,000	ListingRemoved	Agent Provided

10/04/2016	$159,000	PriceChange	Agent Provided
Price Change $16,000 (-9%)
06/29/2016	$175,000	PriceChange	Agent Provided
Price Change $4,900 (-3%)
05/04/2016	$179,900	Listed For Sale	Agent Provided

01/14/2016	$199,900	ListingRemoved	Agent Provided

07/14/2015	$199,900	Listed For Sale	Agent Provided

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	$281,180

Home facts updated by county records

Comparable Sales for 369 Juniper Hill Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
58 Morningside Drive, Windsor, VT	0.28	Single-Family Home	$395,900	11/13/25	3	1.5	1,680
205 Channing Drive, Windsor, VT	0.48	Single-Family Home	$310,000	09/05/25	2	1.5	1,391
672 County Road, Windsor, VT	0.86	Single-Family Home	$340,000	09/05/25	3	2	1,500
255 Channing Drive, Windsor, VT	0.52	Single-Family Home	$350,000	08/29/25	3	2	1,196
473 Taylor Drive, Windsor, VT	0.60	Single-Family Home	$426,000	01/23/26	4	2.5	1,832
9 Main Street, Windsor, VT	0.53	Single-Family Home	$200,001	08/28/25	4	1.5	2,310
14 Central Street, Windsor, VT	0.96	Single-Family Home	$210,000	08/06/25	1	1.5	1,056
161 St Gaudens Road, Cornish, NH	1.17	Single-Family Home	$339,000	12/19/25	4	2	2,656
38 Jarvis Street, Windsor, VT	1.05	Single-Family Home	$139,000	06/10/26	1	1	768
223 Taylor Drive, Windsor, VT	0.80	Single-Family Home	$530,000	04/03/26	4	2.5	2,468

Nearby homes

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

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OFF MARKET
Est. $326,700
4 bd
2 ba
2,289 sqft
2446 US Route 5 North,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $234,600
5 bd
2 ba
2,304 sqft
2460 Route 5N,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $270,000
3 bd
1 ba
1,196 sqft
2156 Route 5 North,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
NOV 13, 2025
$395,900
3 bd
1.5 ba
1,680 sqft
58 Morningside Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $342,900
3 bd
1.5 ba
1,700 sqft
25 Hemlock Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $426,300
3 bd
2 ba
1,638 sqft
37 Morningside Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $323,600
3 bd
2 ba
1,242 sqft
69 Morningside Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $317,500
3 bd
1.5 ba
1,550 sqft
109 Morningside Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $370,700
3 bd
1 ba
2,160 sqft
39 Huntington Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $279,800
3 bd
1 ba
1,710 sqft
242 Huntington Drive,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $315,200
4 bd
1.5 ba
2,310 sqft
9 Main Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $319,000
2 bd
1.5 ba
1,391 sqft
205 Channing Drive,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 369 Juniper Hill Rd.

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
5y 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."
0
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Apartments for Rent

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NEW - 2 DAYS AGO
$1,325/mo
1 bd
1 ba
9 State St #3C,
Windsor, VT 05089
$1,350/mo
1 bd
1 ba
24 State St #1,
Windsor, VT 05089
$1,300/mo
1 bd
1 ba
2326 US Route 5 N #1A,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,450/mo
2 bd
1 ba
55 River St #B,
Windsor, VT 05089
$1,136/mo
Studio
1 ba
18 Union St #C,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
APPLY INSTANTLY
$1,800/mo
2 bd
1 ba
54 Westgate Rd #7,
Plainfield, NH 03781
APPLY INSTANTLY
PET FRIENDLY
$1,495/mo
1 bd
1 ba
51 River St #1,
Windsor, VT 05089
APPLY INSTANTLY
$1,950/mo
1 bd
1 ba
Address Not Disclosed,
Hartland, VT 05048
See more homes for rent in
Windsor
Take a look

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Homes for sale near 369 Juniper Hill Rd

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11 ACRES
$575,000
4 bd
3 ba
2,229 sqft
511 Route 12A,
Cornish, NH 03745
PrimeMLS, Active
$225,000
3 bd
1 ba
1,095 sqft
24 Cherry Street,
Windsor, VT 05089
PrimeMLS, Active
AUCTION
0.48 ACRES
$510,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
5.25 ACRES
$725,000
3 bd
2 ba
2,618 sqft
21 Squag City Road,
Cornish, NH 03745
PrimeMLS, Active
4.96 ACRES
$1,399,000
4 bd
3.5 ba
4,000 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Active
1.22 ACRES
$413,900
4 bd
2.5 ba
2,888 sqft
273 Route 5 North,
Windsor, VT 05089
PrimeMLS, Active
6.8 ACRES
$299,000
2 bd
1 ba
1,152 sqft
466 Estey Lane,
Windsor, VT 05089
PrimeMLS, Active
1.2 ACRES
$239,900
1 bd
1 ba
570 sqft
23 CHASE HILL Road,
Cornish, NH 03745
PrimeMLS, Active
$110,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look