OFF MARKET

Listed by Laura Beckwith • Josiah Allen Real Estate, Inc. Bought with Four Seasons Sotheby's Int'l Realty.

Off Market Aug 2023 for $1.3M

$1,525,772

•

4,160

sq ft

63 Sykes Hollow Rd, Rupert, VT 05776

About this home

Nearby Dorset and quietly located on Sykes Hollow Road, this Expansive Modern New Englander offers the wonders of beautiful natural light on three floors with open floor plan inspiring true indoor-outdoor living. All of the living areas featured in this residence boast walk out to airy life screened or covered porches, decks and feature large window walls taking in the vista's of open grounds, babbling stream, deciduous woodland and Mettowee Valley's rolling hills! There is a large fenced protective area for dogs as well. Built just prior to 2020, this house is in fantastic condition boasting plank pine flooring through out the main level and primary suite. .. the island kitchen joins the butlers pantry with beverage bar and comfortably transitions to the combination living/dining great room where the corner wood burning fireplace is enjoyed by all! The primary suite is spacious and delightfully luxurious with walk-in closets, soaking tub, double vanity and full walk in shower. The guest wing is separate off a large vaulted landing. The lower level offers a wonderful walk out family room, office space, over flow room, bath and expansive laundry. The new Barn and shed allows for a work shop, toy's and so much more with studio second walk out floor available. 12.75 tucked away acres provide privacy without isolation. .. Breathe in fresh air, avoid traffic noise, walk around the grounds, enjoy the gardens. .. gaze upon pastoral views. 7 minutes to the Dorset Green, it's home!

Single-familyProperty Type

2017Year Built

12.75 acresLot Size

$367Est. Price/Sq.Ft.

3 car garageParking

Listed by Laura Beckwith • Josiah Allen Real Estate, Inc.

Bought with Carol O'Connor • Four Seasons Sotheby's Int'l Realty

Redfin checked: a few seconds ago

•Source:PrimeMLS #4957076

Redfin Estimate

$1,525,772

$201K since sold in August 2023$218K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 53.2% higher than the average sale price ($996K) of 6 comparable homes.

SOLD APR 30, 2026
$475,000
A
3 beds2.5 baths2,939 sq ft
1688 Waite Hill Rd, Pawlet, VT 05761
SOLD JUL 15, 2026
$2,200,000
B
4 beds3.5 baths4,265 sq ft
7537 Main St, Manchester Center, VT 05255
SOLD JUL 30, 2026
$1,200,000
C
3 beds2.5 baths2,736 sq ft
12 Beattie Ln, Manchester, VT 05255
SOLD AUG 4, 2026
$776,000
D
4 beds3.5 baths4,282 sq ft
267 Eagle Rdg, Dorset, VT 05251
SOLD JUN 15, 2026
$650,000
E
4 beds4 baths3,161 sq ft
413 Dutch Hill Rd, Danby, VT 05739
SOLD MAY 1, 2026
$675,000
F
3 beds2.5 baths2,400 sq ft
201 Owls Head Hill Ln, Dorset, VT 05251-0000

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Rent

$2,702/mo

Redfin rental estimate

List your home for rent

Market trends in 05761, VT

Last updated August 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

95.2%

0.0% MoM

Median sale price

$347K

$78 MoM

Avg. days on market

132d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

FOR SALE BY OWNER
$140,000
2 beds1 bath— sq ft
128 Bear Mountain Camp Rd, West Rupert, VT 05776
See all

Provided by Redfin

Sale history for 63 Sykes Hollow Rd

Date

Event

Price

PrimeMLS #4957076

Aug 23, 2023

Sold

$1,325,000

$319/sq ft

Jun 18, 2023

Pending

—

Jun 14, 2023

Listed

$1,325,000

$319/sq ft

PrimeMLS #4703350

Feb 18, 2020

Sold

$795,000

$191/sq ft

Jan 16, 2020

Pending

—

Dec 30, 2019

Contingent

—

Jun 27, 2018

Listed

$825,000

$198/sq ft

+26

Sykes Hollow Contemporary residence that has been custom designed and masterfully crafted for today's open concept living. The twelve acre site takes advantage of the distant mountain and meadow views as seen from a traditional wrap around deck which leads to the light filled living room with a cozy corner fireplace. The kitchen and adjoining pantry/wet bar is a cook's dream with high end appliances, granite counter tops, custom cabinetry and a breakfast nook. A spacious master bedroom takes advantage of the views from banks of windows and features an adjoining luxurious bath and over sized walk in closet. Two guest rooms and another bath complete the second story. A large lower level has potential for a media or family room. Newly constructed 20'x32' barn offering two floors and totaling 1280 sq. ft. 2nd floor accessible with a small ramp and doors for wheeled equipment storage. This property is minutes from Dorset and is located 4 miles north of the Dorset Village Green in the picturesque Mettowee Valley.

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

—

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Bennington County

APN

537-169-10548

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Dec 16, 2021.

Agricultural District

This district recognizes the productive value of the lands in the Mettawee Valley and the importance of agriculture to the town’s economy, character and way of life. It is the intent of this district to allow for a range of working land and open space uses, as well as opportunities for the natural-resource based, farm-based and agricultural-support businesses that are integral to maintaining a viable rural economy. The purpose of this district is to implement the goals and policies of the Rupert Town Plan. Specifically the town plan calls for these regulations to: Allow for resourced-based industries in appropriate locations - to include an adequate land base for farming and forestry, needed support services and value-added production; Support the efficient use of land; and Incorporate standards that minimize the fragmentation of important agricultural land and forested wildlife habitat.

Permitted uses

Include but are not limited to:

Agriculture
Housing-Group
Housing-Single unit
Housing-Multiple units
Mixed use
Timberland

Property details

Parking

Parking & Garage
Garage Capacity: 3
Location: Attached
Auto Open, Direct Entry, Heated, Barn
Driveway, Garage, Covered

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2
# of Baths (3/4): 1
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Finished, Full, Storage Space, Walkout

Other Interior Features
# of Rooms: 12
Level B: Family Room, Level B: Laundry Room, Level B: Other
Flooring: Carpet, Softwood, Vinyl Plank
Water Heater: Domestic, Gas - Liquid Propane Bottle
Fireplace - Wood, Fireplaces - 1, Kitchen/Dining, Kitchen/Living, Living/Dining, Soaking Tub, Storage - Indoor, Walk-in Closet, Walk-in Pantry

Equipment & Appliance Information
Dishwasher, Dryer, Exhaust Hood, Freezer, Mini Fridge, Range - Gas, Refrigerator, Washer, Wine Cooler, Exhaust Fan

Room 1 Information
Living/Dining
Living/Dining
Dimensions: 23 X 19 approx
Level: 1

Room 2 Information
Kitchen/Dining
Dimensions: 23 X 14 approx
Level: 1

Room 3 Information
Mudroom
Dimensions: 14 X 8
Level: 1

Room 4 Information
Porch
Dimensions: 15'4" X 11'6 " approx
Level: 1

Room 5 Information
Foyer
Dimensions: 18 X 13 approx
Level: 1

Room 6 Information
Other
Other
Dimensions: 9'5" X 6 approx
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 23'2" X 16'7" approx
Level: 2

Room 8 Information
Full Bath
Dimensions: 19 X 9 approx
Level: 1

Room 9 Information
Bedroom
Dimensions: 16'5" X 11'1" approx
Level: 2

Room 10 Information
Bedroom
Dimensions: 11'10" X 12'6" approx
Level: 2

Room 11 Information
Loft
Dimensions: 24 X 20 stairs in landing
Level: 2

Room 12 Information
Family Room
Dimensions: 21'5" X 19 walk out approx
Level: Basement

Room 13 Information
Other
Dimensions: 14 X 11 walk out approx
Level: Basement

Room 14 Information
Laundry Room
Dimensions: 17'5" X 9'7" approx
Level: Basement

Room 15 Information
Other
Dimensions: 14'5" X 10 approx
Level: Basement

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 4160
Approximate Sq. Ft. Total: 4282
Color: Grey
Barn, Deck, Fence - Dog, Garden Space, Natural Shade, Patio, Porch - Screened, Shed
Construction: Wood Frame
Foundation: Poured Concrete
Roof: Shingle - Asphalt
Exterior: Clapboard

Driveway
Circular, Gravel

Lot, Zoning, & Easement Information
Lot: 007
Easements: Yes
Country Setting, Open, Sloping, Stream, View, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 2017

Financial

Tax Information
Tax Year: 23
Gross Amount Tax: 14475.24
SPAN Number: 537-169-10548

Other Tax Information
Page Deed: 290-293

Utilities

Heating & Cooling Information
Cooling: Mini Split
Heat: Baseboard, Multi Zone, Radiant Floor
Heat Fuel: Gas - Liquid Propane Bottle

Sewer Information
1000 Gallon, Leach Field, Private, Septic

Electric Information
Electric Company: Green Mountain Power
200 Amp

Water Information
Drilled Well

Other Utilities Information
Cable Company: Comcast
Phone Company: VTeL
Cable - At Site, Internet - Cable, Internet - Fiber Optic, Telephone Available

Location

School Information
School District: Rupert School District
Elementary School: Mettowee Community School
Elementary School: Mettowee Community School
Middle/Jr School: Choice

Neighborhood Information
Near Country Club, Near Shopping, Near Skiing, Near Snowmobile Trails

Road Information
Public, Unpaved, Easement/ROW

Other Location Information
Directions: North of Dorset Green, Route 30 to Sykes Hollow Road...over bridge, first drive on Left take driveway to the Left. Lower Barn drive, upper House Circular drive.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Bennington County
APN: 537-169-10548

Home facts updated by county records on Dec 16, 2021

Other

Documents & Disclosures
Documents Available: Deed, Plot Plan, State Wastewater Permit, Survey

Around this home

Schools

Mettawee Community School Unified School District #47

Public PreK-6 • Assigned • 7.0mi

5/10

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

2/10 Heat Factor

7 days above 88° expected this year, 16 days in 30 years

3/10 Wind Factor

5% 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

Rupert, VT • 05776

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 8.4 hours in June and 3.4 hours in December, placing it below the U.S. average for solar exposure.

8.4 hrs

3.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.45M – $1.76M

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

Nearby similar homes

$565,000

3 beds3 baths2,372 sq ft

289 Lamb Hill Rd, Wells, VT 05774

$975,000

3 beds2 baths2,403 sq ft

99 Holly's Way, West Rupert, VT 05776

$599,000

4 beds3 baths2,886 sq ft

209 Kelley Hill Rd, Danby, VT 05739

$515,000

3 beds2 baths1,528 sq ft

335 Tinmouth Rd, Danby, VT 05739

$639,000

4 beds3 baths3,272 sq ft

1174 N Main St, Danby, VT 05739

$550,000

3 beds2 baths2,009 sq ft

1625 Barnumville Rd, Manchester Center, VT 05255

New listings for sale in 05776

FOR SALE BY OWNER

$140,000

2 beds1 bath— sq ft

128 Bear Mountain Camp Rd, West Rupert, VT 05776

Home values near 63 Sykes Hollow Rd

Data from public records.

Address	Redfin Estimate
513 Sykes Hollow Road, Pawlet, VT 3 Beds \| 1 Baths \| 1764 Sq. Ft.	$331,082
14 Sykes Hollow Road, Rupert, VT 3 Beds \| 2 Baths \| 1845 Sq. Ft.	$635,387

Address	Redfin Estimate
369 Sykes Hollow Road, Rupert, VT 4 Beds \| 3 Baths \| 2800 Sq. Ft.	$2,149,156
694 Sykes Hollow Road, Rupert, VT - Beds \| - Baths \| - Sq. Ft.	$592,426

Address	Redfin Estimate
694 Sykes Hollow Road, Pawlet, VT 3 Beds \| 2.5 Baths \| 2259 Sq. Ft.	$936,101
65 Sykes Hollow Road, Rupert, VT 3 Beds \| 3.5 Baths \| 4325 Sq. Ft.	$1,447,793

Property information provided by PrimeMLS when last listed in 2023. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Bennington County	Agents near me	Brattleboro, VT homes for sale	Bennington County Housing Market
Houses for sale near me	Burlington, VT homes for sale	South Burlington, VT homes for sale
Land for sale near me	Stowe, VT homes for sale	Rutland, VT homes for sale
Open Houses near me	Woodstock, VT homes for sale	Bennington County Property Records
Condos for sale near me	Montpelier, VT homes for sale	VT New Listings

Columbia County homes for sale
Saratoga County homes for sale
Berkshire County homes for sale

Wilmington homes for sale
Manchester homes for sale
Bennington homes for sale