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, 90% 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, 78% of users say it's walkable to restaurants

Is parking easy in Windsor, VT?

As of early 2026, 67% of users say parking is easy

Would people walk alone at night in Windsor, VT?

As of early 2026, 67% of users say people would walk alone at night

Are the streets well-lit in Windsor, VT?

As of early 2026, 64% of users say streets are well-lit

Is Windsor, VT quiet?

As of early 2026, 64% of users say it's quiet

Does Windsor, VT have sidewalks?

As of early 2026, 64% of users say there are sidewalks

Do kids play outside in Windsor, VT?

As of early 2026, 64% of users say kids play outside

Does Windsor, VT show holiday spirit?

As of early 2026, 60% of users say there's holiday spirit

Is there wildlife in Windsor, VT?

As of early 2026, 60% of users say there's wildlife

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

Listed by Blue Slate Realty, Blue Slate Realty, (802) 318-2647 . Bought with BHG Masiello Keene

338 US Route 5 South
Windsor, VT 05089

6 Beds
2 Baths
2,504 sqft (on 0.65 acres)

$246,200

Trulia Estimate

as of Jun 17, 2026

$246,200

Trulia Estimate

as of Jun 17, 2026

6 Beds

2 Baths

2,504 sqft

(on 0.65 acres)

Local Information

-- mins to

Commute Destination

Last check for updates: about 7 hours ago

Listed by Blue Slate Realty

Blue Slate Realty, (802) 318-2647

Bought with: Jessica Samples, BHG Masiello Keene, (603) 352-5433

Source: PrimeMLS, MLS#5040488

Description

Imagine waking to the soft glow of dawn filtering through the windows of your charming three-story farmhouse, nestled in the heart of Vermont’s historic birthplace. As you sip coffee in the sunlit kitchen, the Connecticut River glimmers across the street, promising a day of serenity. This -bedroom, 2-bath home, brimming with character, becomes your sanctuary. Upstairs, the tranquil bedrooms offer restful retreats, while the convenient laundry room keeps life humming smoothly. Transform the expansive bonus rooms into a lively playspace or cozy den for movie nights. The third-floor loft, with its kitchenette and sweeping bonus space, becomes your haven for creative pursuits—an art studio, yoga retreat, or a cozy guest suite for visiting friends. Weekends are filled with possibility. Your mornings begin with a stroll through the yard, where stone pathways wind through gardens, perfect for quiet reflection or playful moments with family. You tinker in the large attached barn, now a workshop for woodworking or a rustic venue for hosting farm-to-table dinners under string lights. The nearby towns of Lebanon and Claremont buzz with farmers’ markets and quaint shops, just a short drive away, while Dartmouth’s medical facility ensures peace of mind. When winter blankets the landscape, you head to nearby ski areas for powdery adventures. Showings begin Saturday, May 17.

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 July 21, 2025

Home Highlights

Parking

Open Parking

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

180+ days ago

Home Details for 338 US Route 5 South

Active Status
MLS Status: Closed

Interior Features
Interior Details Basement: Bulkhead,Concrete Floor,Interior Stairs,Unfinished,Interior EntryNumber of Rooms: 11
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 2504 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Refrigerator, Electric StoveRefrigerator
Heating & Cooling Heating: OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Window: Skylight(s)Flooring: Laminate, Wood, Vinyl Plank
Levels, Entrance, & Accessibility Stories: 3Levels: 3Floors: Laminate, Wood, Vinyl Plank
View No View
Security Security: Carbon Monoxide Detector(s), Smoke Detector(s)

Exterior Features
Exterior Home Features Roof: MetalPatio / Porch: Covered PorchFoundation: Stone
Parking & Garage No CarportNo GarageHas Open ParkingParking: Gravel,Driveway
Frontage Road Frontage: TBD, PublicResponsible for Road Maintenance: Public Maintained Road
Water & Sewer Sewer: 1000 Gallon
Finished Area Finished Area (above surface): 2504 Square Feet

Property Information
Year Built Year Built: 1840
Property Type / Style Property Type: ResidentialProperty Subtype: FarmStructure Type: FarmhouseArchitecture: Farmhouse
Building Construction Materials: Clapboard Exterior, Wood SidingNot a New Construction

Price & Status
Price List Price: $240,000

Location
Direction & Address City: Windsor

Building
Building Area Building Area: 3590 Square Feet

Lot Information
Lot Area: 0.65 acres

Miscellaneous
BasementMls Number: 5040488Above Grade Unfinished Area: 2504Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 1086Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price History for 338 US Route 5 South

Date	Price	Event	Source
07/21/2025	$240,000	Sold	PrimeMLS #5040488
Recording Date 07/21/2025 County Transfer Tax N/A Total Transfer Tax N/A
05/21/2025	$240,000	Contingent	PrimeMLS #5040488

05/13/2025	$240,000	PriceChange	PrimeMLS #5040488
Price Change $55,000 (-19%)
03/27/2025	$295,000	PriceChange	N/A
Price Change $15,000 (-5%)
03/20/2025	$310,000	Listed For Sale	N/A

09/18/2024	$100,000	Sold	PrimeMLS #4992919
Recording Date 09/18/2024 County Transfer Tax N/A Total Transfer Tax N/A
07/17/2024	$110,000	PriceChange	PrimeMLS #4992919
Price Change $15,000 (-12%)
05/31/2024	$125,000	PriceChange	PrimeMLS #4992919
Price Change $25,000 (-17%)
05/29/2024	$150,000	PriceChange	PrimeMLS #4992919
Price Change $15,000 (-9%)
05/21/2024	$165,000	PriceChange	PrimeMLS #4992919
Price Change $10,000 (-6%)
04/26/2024	$175,000	Listed For Sale	PrimeMLS #4992919

10/20/2006	$140,000	Sold	N/A
Recording Date 10/20/2006 Contract Date 10/19/2006 County Transfer Tax N/A Total Transfer Tax $1,000

Market trends in Windsor

Last updated May 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	$124,830

Home facts updated by county records

Homeowner tools

Estimated monthly rent$3,402/mo

List your home for rent

Comparable Sales for 338 US Route 5 South

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
32 Clough Avenue, Windsor, VT	0.40	Single-Family Home	$292,500	08/28/25	3	1.5	1,606
31 Maple Street, Windsor, VT	0.43	Single-Family Home	$215,000	10/06/25	3	1.5	1,900
3 Fitch Court, Windsor, VT	0.63	Single-Family Home	$229,000	06/25/25	2	2	1,665
10 McKenzie Drive, Windsor, VT	0.51	Single-Family Home	$271,000	11/13/25	3	1.5	1,320
66 Union Street, Windsor, VT	0.60	Single-Family Home	$219,000	09/02/25	3	2	1,743
9 Main Street, Windsor, VT	1.11	Single-Family Home	$200,001	08/28/25	4	1.5	2,310
1 Dorrance Street, Windsor, VT	0.65	Single-Family Home	$315,000	11/21/25	2	1.5	1,649
3 Cherry Street, Windsor, VT	0.56	Single-Family Home	$259,000	05/01/26	3	1	1,176

Nearby homes

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

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NEW
COMING SOON 6/18
4.96 ACRES
$1,399,000
4 bd
3.5 ba
3,720 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Coming Soon
OFF MARKET
357 Route 5,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
AUG 26, 2025
$305,000
3 bd
5 ba
1,754 sqft
8 Old Mill Pond Road,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $278,300
3 bd
4 ba
2,052 sqft
4 Old Mill Pond Road #4,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $329,800
4 bd
1.5 ba
1,800 sqft
6 Buena Vista Court,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
AUG 28, 2025
$292,500
3 bd
1.5 ba
1,606 sqft
32 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $231,700
3 bd
1 ba
1,024 sqft
17 Maple Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
OCT 6, 2025
$215,000
3 bd
1.5 ba
1,900 sqft
31 Maple Street,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $285,500
4 bd
2 ba
3,266 sqft
17 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed
OFF MARKET
Est. $187,400
2 bd
1 ba
1,115 sqft
25.5 Union Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
DEC 18, 2025
$60,000
3 bd
1 ba
1,392 sqft
5 Clough Avenue,
Windsor, VT 05089
PrimeMLS, Closed

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Additional Cost

Assigned Schools

These are the assigned schools for 338 US Route 5 South.

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

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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LGBTQ Local Legal Protections

Apartments for Rent

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$1,575/mo
2 bd
1 ba
45-47 Ascutney Blvd #4,
Windsor, VT 05089
$1,650/mo
2 bd
1 ba
75 Union St #3,
Windsor, VT 05089
$1,136/mo
Studio
1 ba
18 Union St #C,
Windsor, VT 05089
$1,450/mo
2 bd
1 ba
55 River St #B,
Windsor, VT 05089
$1,950/mo
3 bd
1 ba
8 Union St #4,
Windsor, VT 05089
$1,795/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
24 Durkee St #B,
Windsor, VT 05089
$1,750/mo
2 bd
1 ba
77 Union St #2,
Windsor, VT 05089
Contact for price
1-2 bd
1-2 ba
65 State St #f320a52c6,
Windsor, VT 05089
$1,500/mo
2 bd
1 ba
4-10 Central St,
Windsor, VT 05089
$2,250/mo
3 bd
1 ba
21-23 Maple St,
Windsor, VT 05089
APPLY INSTANTLY
PET FRIENDLY
$1,547/mo
1 bd
1 ba
51 River St #1,
Windsor, VT 05089
See more homes for rent in
Windsor
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Explore by feature - Washer/dryer

$1,675/mo
1 bd
1 ba
68 Ascutney St,
Windsor, VT 05089
$2,900/mo
3 bd
1 ba
69 Belknap Ln,
Windsor, VT 05089
$2,250/mo
3 bd
1 ba
21-23 Maple St,
Windsor, VT 05089
$1,795/mo
2 bd
1 ba
16-20 State St #B,
Windsor, VT 05089
$1,750/mo
2 bd
1 ba
77 Union St #2,
Windsor, VT 05089

Homes for sale near 338 US Route 5 South

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NEW
COMING SOON 6/18
4.96 ACRES
$1,399,000
4 bd
3.5 ba
3,720 sqft
145 The Plateau,
Windsor, VT 05089
PrimeMLS, Coming Soon
AUCTION
0.48 ACRES
$515,000
6 bd
4 ba
4,933 sqft
2 Pine Street,
Windsor, VT 05089
PrimeMLS, Active
$115,000
1 bd
1 ba
240 sqft
505 Back Mountain Road #14,
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
15.12 ACRES
$625,000
5 bd
3 ba
3,510 sqft
330 Parsonage Road,
Cornish, NH 03745
PrimeMLS, Active
3.2 ACRES
$599,000
4 bd
3 ba
3,200 sqft
84 Old Barn Lane,
West Windsor, VT 05089
PrimeMLS, Active
NEW - 2 DAYS AGO
5.25 ACRES
$725,000
3 bd
2 ba
2,618 sqft
21 Squag City Road,
Cornish, NH 03745
PrimeMLS, Active
1.53 ACRES
$474,800
3 bd
2 ba
1,480 sqft
586 Ski Tow Road,
Brownsville, VT 05037
PrimeMLS, Active
5.51 ACRES
$1,345,000
7 bd
5 ba
5,774 sqft
310 Pierce Hill Road,
Windsor, VT 05089
PrimeMLS, Active
See more homes for sale in
Windsor
Take a look

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Off Market Homes Near 338 US Route 5 South

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SOLD
JUN 10, 2026
$330,000
2 bd
2 ba
1,604 sqft
290 Village Lane,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
MAY 21, 2026
$195,000
Hotel Rd,
Brownsville, VT 05037
SOLD
MAY 15, 2026
$195,000
3 bd
1,604 sqft
295 Hotel Road #10/10A,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
MAY 1, 2026
$259,000
3 bd
1 ba
1,176 sqft
3 Cherry Street,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
APR 30, 2026
$142,500
3 bd
2 ba
1,549 sqft
66 Country Skyline Boulevard,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
APR 30, 2026
$230,000
3 bd
2 ba
1,434 sqft
19 SPRUCE PARK Drive #19,
Plainfield, NH 03781
PrimeMLS, Closed
SOLD
APR 23, 2026
$185,000
295 Hotel Rd,
Brownsville, VT 05037
SOLD
APR 22, 2026
$295,000
3 bd
3 ba
1,594 sqft
72 Mountains Edge Road #508,
Brownsville, VT 05037
PrimeMLS, Closed
SOLD
APR 17, 2026
$185,000
2 bd
1.5 ba
850 sqft
295 Hotel Road #15,
Windsor, VT 05089
PrimeMLS, Closed
SOLD
APR 8, 2026
$201,000
0 Town House Road #28,
Cornish, NH 03745
PrimeMLS, Closed
See more homes for sale in
Windsor
Take a look

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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 2026-06-17 05:16:43 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.

338 US Route 5 South, Windsor, VT 05089 is a 6 bedroom, 2 bathroom, 2,504 sqft single-family home built in 1840. This property is not currently available for sale. 338 US Route 5 South was last sold on Jul 21, 2025 for $240,000 (0% higher than the asking price of $240,000). The current Trulia Estimate for 338 US Route 5 South is $246,200.

338 US Route 5 South
Windsor, VT 05089

$246,200

$246,200

Local Information