Is a car needed in Jamaica, VT?

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

Do kids play outside in Jamaica, VT?

As of early 2026, 100% of users say kids play outside

Are yards well-kept in Jamaica, VT?

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

Does Jamaica, VT have sidewalks?

As of early 2026, 67% of users say there are sidewalks

Is there wildlife in Jamaica, VT?

As of early 2026, 67% of users say there's wildlife

Is Jamaica, VT walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Is parking easy in Jamaica, VT?

As of early 2026, 50% of users say parking is easy

Is Jamaica, VT quiet?

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

Are there community events in Jamaica, VT?

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

Are neighbors friendly in Jamaica, VT?

As of early 2026, 33% of users say neighbors are friendly

FOR SALE

FOR SALE BY OWNER

20 ACRES

2766 Windham Hill Rd
Windham, VT 05359

3 Beds
3 Baths
2,400 sqft (on 20 acres)

$524,000

$549,999

Est. Mortgage $3,622/mo*

Get Pre-Qualified

$524,000

$549,999

Est. Mortgage $3,622/mo*

Get Pre-Qualified

3 Beds

3 Baths

2,400 sqft

(on 20 acres)

Home Highlights

Parking

Garage

Outdoor

Deck

Climate Control

Heating only

Price/Sqft

$218

Listed

66 days ago

Local Information

Map ViewExplore the area around 2766 Windham Hill Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

Historic Southern Vermont Homestead. Post & Beam 3 BR/3BA plus loft Farmhouse with 2 car post & beam garage/barn, and versatile detached barn. Easily converted to have an 1.5BR/1BA rental or in law suite. Two beautifully updated full baths and new hot water heater. Northern walls insulated. In addition to the 4 zone furnace, there are 2 wood stoves plus a propane stove that looks like a "wood" stove", but runs without electricity if needed, to lower seasonal heating footprint. Upgraded electrical wiring in key areas. There is a newer 16x34 foot barn with water access and electric. Spread across almost 20 private acres, the property delivers sweeping rural views, pastures for homesteading, and is located on desirable Windham Hill Road with abundant lawn, mature flower gardens, fruit trees and bushes, perennial food garden, and three fields separated by mixed wood, and thousands of linear feet of centuries old stone walls and paths. Buyer Agents Welcome.

Home Details for 2766 Windham Hill Rd

Interior Features
Interior Details BasementAtticIn-law unitNumber of Rooms: 11Types of Rooms: Dining Room, Family Room, Laundry Room, Mud Room, Pantry, Workshop, Sun Room
Heating & Cooling Heating: Baseboard, Other, Stove, Oil, Propane Butane, Wood PelletHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2Floors: Softwood, Other, Hardwood, Laminate
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features
Exterior Home Features Roof: MetalDeckExterior: Stone, Wood, MetalGardenLawn
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached, Off Street

Days on Market
Days on Market: 66 days on Trulia

Property Information
Year Built Year Built: 1800
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Price & Status
Price Price Per Sqft: $218

Lot Information
Lot Area: 20.00 acres

Market trends in Jamaica

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

4MoM

Price History for 2766 Windham Hill Rd

Date	Price	Event	Source
07/23/2026	$524,000	PriceChange	N/A
Price Change $25,999 (-5%)
06/21/2026	$549,999	PriceChange	N/A
Price Change $49,001 (-8%)
06/15/2026	$599,000	PriceChange	N/A
Price Change $50,000 (-8%)
06/03/2026	$649,000	PriceChange	N/A
Price Change $50,000 (-7%)
05/26/2026	$699,000	Listed For Sale	N/A

08/11/2025		ListingRemoved	N/A

06/11/2025	$799,000	PriceChange	N/A
Price Change $50,000 (-6%)
06/02/2025	$849,000	Listed For Sale	N/A

08/17/2016	$240,000	Sold	PrimeMLS #4499310
Recording Date 08/17/2016 County Transfer Tax N/A Total Transfer Tax N/A
05/17/2008	$61,690	ListingRemoved	Agent Provided

04/04/2008	$61,690	Listed For Sale	Agent Provided

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Property Tax and Assessment

Year	2024
Tax
Assessment	$342,500

Home facts updated by county records

Comparable Sales for 2766 Windham Hill Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
956 Old Cheney Road, Windham, VT	0.98	Single-Family Home	$625,000	01/15/26	2	2	2,144
466 Wheeler Road, Windham, VT	1.33	Single-Family Home	$390,000	10/03/25	3	2	1,554
1905 Turkey Mountain Road, Jamaica, VT	2.02	Single-Family Home	$484,000	07/01/26	3	2.5	2,584
3091 State Route 121, West Townshend, VT	1.83	Single-Family Home	$364,000	08/28/25	4	2	2,000
70 Worden Lane, West Townshend, VT	2.62	Single-Family Home	$305,000	10/02/25	3	1.5	1,602
756 Turkey Mountain Road, Jamaica, VT	2.79	Single-Family Home	$300,000	03/16/26	3	2	1,468
98 Gleason Farm Lane, Jamaica, VT	3.26	Single-Family Home	$586,750	04/30/26	3	3	2,700
199 Turkey Mountain Road, Jamaica, VT	3.29	Single-Family Home	$480,000	05/21/26	3	2.5	2,254
64 Gleason Farm Lane, Jamaica, VT	3.30	Single-Family Home	$555,000	02/26/26	3	2.5	2,033
69 Chapin Lane, Jamaica, VT	3.31	Single-Family Home	$530,000	08/08/25	4	3	2,052

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

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OFF MARKET
Est. $242,200
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OFF MARKET
Est. $1,353,200
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OFF MARKET
Est. $43,800
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PrimeMLS, Closed
OFF MARKET
Est. $157,300
445 Wheeler Road,
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12.5 ACRES
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Off Robin Hill Road,
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PrimeMLS, Active
OFF MARKET
1995 Back Windham Road,
Townshend, VT 05353
PrimeMLS, Closed

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 2766 Windham 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 Jamaica

At least 1 Trulia users voted on each feature.

100 % Say car is needed
100 % Say kids play outside
100 % Say yards are well-kept
67 % Say there are sidewalks
67 % Say there's wildlife
50 % Say it's walkable to grocery stores
50 % Say parking is easy
50 % Say it's quiet
50 % Say there are community events
33 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

This property is for sale by owner and Zillow, Inc. is displaying it at the owner’s request. It is not subject to a listing agreement with Zillow, Inc. or its affiliates.

2766 Windham Hill Rd, Windham, VT 05359 is a 3 bedroom, 3 bathroom, 2,400 sqft single-family home built in 1800. This property is currently available for sale and was listed on May 26, 2026.

2766 Windham Hill Rd
Windham, VT 05359

$524,000