OFF MARKET

Listed by Christopher Cummings • Cummings & Co. Bought with Cummings & Co.

Off Market Nov 2024 for $640K

$760,652

Est. refi paymentEst. refi $4,191/mo

•

3,280

sq ft

660 Dalewood Rd, Jamaica, VT 05343

About this home

Incredible opportunity to have your very own turnkey Stratton Mountain escape! Located on a quiet road, 3.5 miles from the Village, this lovely home has generated a treasure trove of memories for the owner's family for the last several years. Enter from the comfort of the attached garage into a generous mudroom, and head up to the main level where you'll find a well appointed chef's kitchen and large adjacent dining area. Kick back and relax in the ambiance of your spacious living room with soaring cathedral ceilings, huge windows and efficient fireplace insert. Ensuite primary on the main level, a second ensuite primary and two more bedrooms on the finished lower level provide plenty of room to spread out. Bonus room located above the garage. Large wraparound deck for dining al fresco, or enjoy the Stratton mountaintop view with a favorite beverage in the warm embrace of your hot tub. There is also a whole house generator to ensure your continued comfort during the rare power outages. Detached second garage. Offered fully furnished.

Single-familyProperty Type

1996Year Built

1.6 acresLot Size

$232Est. Price/Sq.Ft.

1 car garageParking

Listed by Christopher Cummings • Cummings & Co

Bought with Christopher Cummings • Cummings & Co

Redfin checked: a minute ago

•Source:PrimeMLS #4997275

Redfin Estimate

$760,652

$121K since sold in November 2024$12K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.2% lower than the average sale price ($811K) of 6 comparable homes.

SOLD JUL 17, 2026
$799,000
A
4 beds3.5 baths3,078 sq ft
63 Raspberry Hill Rd, Winhall, VT 05340
SOLD AUG 28, 2026
$615,000
B
3 beds3.5 baths2,678 sq ft
177 Alwin Ln, Jamaica, VT 05343
SOLD JUN 26, 2026
$799,000
C
4 beds3 baths2,797 sq ft
13 Betty Johnson Ln, Winhall, VT 05340
SOLD SEP 1, 2026
$1,310,000
D
4 beds2.5 baths2,814 sq ft
19 Maple Hill Rd, Winhall, VT 05340
SOLD AUG 17, 2026
$580,000
E
4 beds3 baths3,700 sq ft
53 Country Ln, West Wardsboro, VT 05360
SOLD AUG 25, 2026
$765,000
F
3 beds4 baths3,086 sq ft
145 Leon Stocker Dr, Stratton, VT 05360

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Earn from this home

Refinance

Est. cash available

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Rent

$2,962/mo

Redfin rental estimate

List your home for rent

Market trends in 05343, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.7%

+0.2% MoM

Median sale price

$450K

$67K MoM

Avg. days on market

58d

8 days MoM

Recently sold homes

4 MoM

New listings for sale

$995,000
5 beds4.5 baths3,363 sq ft
1189 Cole Pond Rd, Jamaica, VT 05343
See all

Provided by Redfin

Sale history for 660 Dalewood Rd

Date

Event

Price

PrimeMLS #4997275

Nov 13, 2024

Sold

$640,000

$195/sq ft

Oct 17, 2024

Contingent

—

Sep 18, 2024

Relisted

—

Aug 16, 2024

Contingent

—

Aug 12, 2024

Price Changed

$696,911

$212/sq ft

Jul 8, 2024

Price Changed

$769,900

$235/sq ft

May 24, 2024

Listed

$819,900

$250/sq ft

PrimeMLS #4191376

Aug 23, 2013

Sold

$410,000

$125/sq ft

Oct 10, 2012

Listed

$429,900

$131/sq ft

Located on the backside of Stratton Mountain off the Access Road and minutes to the Sun Bowl, this property is an exceptional value. The house was designed by a prominent local builder especially for the current owners. Walk in the front door to a foyer and then a large living area to the left, open floor plan, vaulted living/dining area with massive field stone fireplace. The modern kitchen/breakfast bar is in pristine condition. The master bedroom suite is located on the first level. Climb a short flight of stairs to a TV/game room on the second level. Walk downstairs to 2 bedrooms and additional master suite, perfect for family and guests and convenient Laundry Room. The one car attached garage offers additional storage space. This welcoming home is in immaculate condition, and offers the Stratton experience at a lower cost both in price and real estate taxes. Come take a look! Furnishings are an option.

Year

Property tax

Land + Additions

Assessment*

2025

$10,645 (+15.3%)

$75,400 + $413,800

$489,200

2024

$9,237 (+45.3%)

$75,400 + $413,800

$489,200

2023

$6,359 (−17.3%)

$75,400 + $300,200

$375,600

2022

$7,690 (−2.2%)

$75,400 + $300,200

$375,600

2021

$7,861 (+1.6%)

$75,400 + $300,200

$375,600

2020

$7,740 (+3.0%)

$75,400 + $300,200

$375,600

2019

$7,513 (−0.1%)

$75,400 + $300,200

$375,600

2018

$7,523 (+57.0%)

$75,400 + $298,800

$374,200

2017

$4,792 (+0.7%)

$74,900 + $205,300

$280,200

2016

$4,757 (+0.3%)

$74,900 + $205,300

$280,200

2015

$4,743 (−0.5%)

$74,900 + $205,300

$280,200

2014

$4,766

$74,900 + $198,200

$273,100

2013

$74,900 + $198,200

$273,100

Tax history for 660 Dalewood Rd

Year

Property tax

Land + Additions

Assessment*

2025

$10,645 (+15.3%)

$75,400 + $413,800

$489,200

2024

$9,237 (+45.3%)

$75,400 + $413,800

$489,200

2023

$6,359 (−17.3%)

$75,400 + $300,200

$375,600

2022

$7,690 (−2.2%)

$75,400 + $300,200

$375,600

2021

$7,861 (+1.6%)

$75,400 + $300,200

$375,600

2020

$7,740 (+3.0%)

$75,400 + $300,200

$375,600

2019

$7,513 (−0.1%)

$75,400 + $300,200

$375,600

2018

$7,523 (+57.0%)

$75,400 + $298,800

$374,200

2017

$4,792 (+0.7%)

$74,900 + $205,300

$280,200

2016

$4,757 (+0.3%)

$74,900 + $205,300

$280,200

2015

$4,743 (−0.5%)

$74,900 + $205,300

$280,200

2014

$4,766

$74,900 + $198,200

$273,100

2013

$74,900 + $198,200

$273,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.6 Acres

Year renovated

—

Sq. Ft.

1,832

Year built

1996

Style

Single Family Residential

County

Windham County

APN

32410110391

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 8, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 1

Interior

Bathroom Information
# of Baths (full): 3
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Finished, Insulated, Interior Access

Other Interior Features
# of Rooms: 8

Exterior

Building Information
Architectural Style: Contemporary
Construction Status: Existing
Construction Materials: Wood Frame, Clapboard Exterior
Approximate Sq. Ft. Total Finished: 3280
Approximate Sq. Ft. Total: 3280
Foundation: Concrete
Roof: Shingle - Architectural

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot Features: Landscaped, Open, Rolling

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1996

Financial

Tax Information
Tax Year: 2023
Gross Amount Tax: 9044.45
SPAN Number: 324-101-10391

Other Tax Information
Page Deed: 528 - 529

Utilities

Heating & Cooling Information
Heat: Baseboard, Hot Water
Heat Fuel: Gas - Liquid Propane Bottle

Sewer Information
1000 Gallon, Leach Field - Conventionl

Electric Information
200 Amp, Circuit Breaker(s), Generator

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: High Speed Intrnt -Avail
Cable

Location

Road Information
Road Frontage: Yes
Road Frontage Length: 236
Dirt, Gravel, Public

Other Location Information
Directions: From Stratton access road turn L onto Upper Taylor Hill, continue on Pikes Falls Rd. for 2.2 mi. and turn L on Dalewood Rd.; follow .7 mi. to property on the R. From Rte. 30 in center of Jamaica turn L on Pikes Falls Rd. Go 4.6 mi. and turn R on Dalewood Rd. Follow .7 mi. to property on R.

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 1,832
Stories: 1.0
Lot Size: 1.6 acres
Style: Single Family Residential
Year Built: 1996
Year Renovated: —
County: Windham County
APN: 32410110391

Home facts updated by county records on Jul 8, 2026

Other

Misc. Information
Seasonal: Yes

Around this home

Schools

Leland & Gray Uhsd #34

Public 6-12 • Assigned • 10.3mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

8 days above 85° expected this year, 18 days in 30 years

3/10 Wind Factor

6% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Jamaica, VT • 05343

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.2 hours in June and 3.5 hours in December, placing it below the U.S. average for solar exposure.

8.2 hrs

3.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$723,000 – $875,000

Sell confidently with a local market expert in Jamaica. 3 minutes to get started.

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New listings for sale in 05343

$995,000

5 beds4.5 baths3,363 sq ft

1189 Cole Pond Rd, Jamaica, VT 05343

Home values near 660 Dalewood Rd

Data from public records.

Address	Redfin Estimate
629 Dalewood Rd, Jamaica, VT 4 Beds \| 2 Baths \| 1766 Sq. Ft.	$519,845
886 Dalewood Rd, Jamaica, VT 3 Beds \| 2.5 Baths \| 1536 Sq. Ft.	$668,179

Address	Redfin Estimate
614 Dalewood Rd, Jamaica, VT 3 Beds \| 2 Baths \| 2096 Sq. Ft.	$595,918
511 Dalewood Rd, Jamaica, VT 4 Beds \| 2 Baths \| 2100 Sq. Ft.	$529,739

Address	Redfin Estimate
843 Dalewood Rd, Jamaica, VT 3 Beds \| 3.5 Baths \| 2078 Sq. Ft.	$571,385
544 Dalewood Rd, Jamaica, VT 5 Beds \| 4.5 Baths \| 2600 Sq. Ft.	$767,695

Property information provided by PrimeMLS when last listed in 2024. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05343, VT

Sale history for 660 Dalewood Rd

Tax history for 660 Dalewood Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05343

Home values near 660 Dalewood Rd

More real estate resources