OFF MARKET

Listed by Betsy Cetron • Stratton Real Estate. Bought with Four Seasons Sotheby's Int'l Realty.

Off market dec 2018 for $215K

$509,812

•

1,700

sq ft

14 Deepwoods Rd, Winhall, VT 05340

About this home

Single-familyProperty Type

1978Year Built

1.2 acresLot Size

$300Est. Price/Sq.Ft.

Listed by Betsy Cetron • Stratton Real Estate

Bought with Courtney Leggett • Four Seasons Sotheby's Int'l Realty

Redfin checked: a few seconds ago

•Source:PrimeMLS #4676944

Redfin Estimate

$509,812

$295K since sold in December 2018$12K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.4% lower than the average sale price ($512K) of 5 comparable homes.

SOLD SEP 4, 2026
$540,000
A
3 beds2 baths1,809 sq ft
185 Kelleher Rd Unit 10-00-99, Dorset, VT 05251
SOLD APR 23, 2026
$450,000
B
3 beds2.5 baths1,392 sq ft
354 New Ireland Rd, Manchester Center, VT 05255
SOLD OCT 23, 2026
$468,000
C
3 beds2 baths1,830 sq ft
292 Forest Mountain Rd, Peru, VT 05152
SOLD OCT 23, 2026
$417,500
D
2 beds2.5 baths1,490 sq ft
7330 Main St, Manchester Center, VT 05255
SOLD APR 16, 2026
$685,000
E
3 beds2 baths1,743 sq ft
158 Upland Downs Rd, Manchester Center, VT 05255

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

Earn from this home

Rent

$2,724/mo

Redfin rental estimate

List your home for rent

Market trends in 05255, VT

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

97.2%

0.9% MoM

Median sale price

$674K

$176K MoM

Avg. days on market

112d

14 days MoM

Recently sold homes

2 MoM

New listings for sale

$6,950,000
8 beds9 baths8,690 sq ft
95 Winhall Hollow Rd, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 14 Deepwoods Rd

Date

Event

Price

PrimeMLS #4676944

Dec 7, 2018

Sold

$215,000

$126/sq ft

Oct 9, 2018

Contingent

—

Sep 24, 2018

Price Changed

$239,000

$141/sq ft

Sep 24, 2018

Price Changed

$245,000

$144/sq ft

Aug 3, 2018

Price Changed

$249,000

$146/sq ft

Feb 15, 2018

Listed

$259,000

$152/sq ft

PrimeMLS #4375627

Feb 23, 2016

Sold

$215,000

$126/sq ft

Jan 18, 2016

Contingent

—

Dec 22, 2015

Price Changed

$229,900

$135/sq ft

Dec 22, 2015

Relisted

—

Jul 1, 2015

Delisted

—

Feb 3, 2015

Listed

$245,000

$144/sq ft

+26

Very cute and exceptionally well maintained chalet conveniently located between Manchester and Bromley & Stratton Mountains. 2nd floor living/ dining room with brick fireplace, updated kitchen and master bedroom and bath. Lower level has a nice mud room/entry, family room with brick fp and 2 more bedrooms and bath. Designer paint, quality furnishings, wide board floors which all add to the charm of this cute chalet. Central air a summer time plus! Sold furnished.

PrimeMLS #3076487

Apr 5, 2010

Sold

$221,700

$130/sq ft

Dec 21, 2009

Listed

$239,000

$141/sq ft

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

77112451177

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 15, 2020.

Property details

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2

Basement Information
Basement: Yes
Basement Access: Interior
Crawl Space

Other Interior Features
# of Rooms: 7
Flooring: Softwood, Tile, Vinyl
Water Heater: Electric
Cathedral Ceiling, Dining Area, Fireplace - Screens/Equip, Fireplace - Wood, Fireplaces - 2, Living/Dining, Wood Stove Insert, Laundry - 1st Floor

Equipment & Appliance Information
Dishwasher, Dryer, Exhaust Hood, Range - Gas, Refrigerator, Washer
Air Conditioner, Smoke Detectr-Battery Powered

Room 1 Information
Living Room
Living Room
Dimensions: 14 x 14
Level: 2

Room 2 Information
Dining Room
Dimensions: 14x 14
Level: 2

Room 3 Information
Kitchen
Dimensions: 14 x 10
Level: 2

Room 4 Information
Master Bedroom
Dimensions: 14 x 16
Level: 2

Room 5 Information
Family Room
Dimensions: 12 x 24
Level: 1

Room 6 Information
Bedroom
Bedroom
Dimensions: 10 x 14
Level: 1

Room 7 Information
Bedroom
Dimensions: 14 x 10
Level: 1

Room 8 Information
Mudroom
Dimensions: 8 x8
Level: 1

Room 9 Information
Loft
Dimensions: 10 x 14
Level: 3

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 1700
Approximate Sq. Ft. Total: 1700
Color: brown
Deck, Window Screens, Windows - Double Pane, Windows - Energy Star
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt
Exterior: Stucco, Wood Siding

Driveway
Gravel

Lot, Zoning, & Easement Information
Pond Site, Secluded, Subdivision, View, Wooded

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1978

Financial

Tax Information
Tax Year: 2018
Gross Amount Tax: 3615
SPAN Number: 77112451177

Other Tax Information
Page Deed: 307

Utilities

Heating & Cooling Information
Cooling: Wall AC Units
Heat: Forced Air
Heat Fuel: Kerosene, Oil

Sewer Information
Septic

Electric Information
220 Plug

Water Information
Drilled Well

Other Utilities Information
Cable Company: Comcast
Cable, Cable - At Site, Internet - Cable

Location

School Information
School District: Bennington/Rutland
Elementary School: Choice
Elementary School: Choice
Middle/Jr School: Choice

Road Information
Road Frontage: Yes
Road Frontage Length: 200
Gravel, Public

Other Location Information
Directions: Second house on right on Deepwoods Road -- Long Driveway -- Number out front

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Bennington County
APN: 77112451177

Home facts updated by county records on Aug 15, 2020

Around this home

Schools

K - 12
Preschool & daycare

Some nearby schools may not be within this home's attendance zone. Please check the school district website to verify.

Manchester Elementary/Middle School

Public PreK-8 • 3.4mi

5/10

Burr & Burton Academy

Public 9-12 • 4.8mi

Dorset Elementary School

Public PreK-8 • 3.9mi

8/10

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

1/10 Heat Factor

4 days above 86° expected this year, 9 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

Winhall, VT • 05340

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

8.3 hrs

3.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$485,000 – $587,000

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

Nearby similar homes

$875,000

3 beds2 baths1,600 sq ft

447 Rock Bottom Ln, Peru, VT 05255

Private acres • National forest • Catamount trail

VIDEO TOUR

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Studio1 bath950 sq ft

109 Winhall Hollow Rd, Winhall, VT 05340

23.5-acre property • Spacious deck • 23.5 acre lot

$605,000

3 beds2 baths2,288 sq ft

1 Beaver St, Winhall, VT 05340

Spacious living room • Corner lot • Nice yard

$750,000

4 beds5.5 baths4,502 sq ft

3373 Main St, Manchester, VT 05254

Mountain views • Exposed beams • Custom built-ins

$565,000

4 beds2.5 baths2,399 sq ft

1131 Route 30, Dorset, VT 05251

Picturesque acres • 1.5 acre lot • 2 garage spots

3D & VIDEO TOUR

$975,000

4 beds3 baths3,548 sq ft

259 Beechnut Dr, Peru, VT 05152

Log home • Private acres • Wraparound porch

New listings for sale in 05340

$6,950,000

8 beds9 baths8,690 sq ft

95 Winhall Hollow Rd, Winhall, VT 05340

23 acres • Sweeping views • Completely renovated

Home values near 14 Deepwoods Rd

Data from public records.

Address	Redfin Estimate
7 Deepwoods Road, Winhall, VT 3 Beds \| 2 Baths \| 1800 Sq. Ft.	$688,676
14 Deep Woods Road, Manchester Center, VT 3 Beds \| 2 Baths \| 1456 Sq. Ft.	$440,836
16 Deep Woods Road, Manchester Center, VT 3 Beds \| 2 Baths \| 1200 Sq. Ft.	$427,130
19 Valley View Road, Winhall, VT 4 Beds \| 3 Baths \| 3766 Sq. Ft.	$1,064,599
2 Deep Woods Circle, Manchester Center, VT 4 Beds \| 2 Baths \| 1736 Sq. Ft.	$459,477
17 Valley View Road, Winhall, VT 4 Beds \| 4.5 Baths \| 4315 Sq. Ft.	$1,680,456
5 Old Snow Valley Road, Winhall, VT 3 Beds \| 3 Baths \| 1028 Sq. Ft.	$384,978

Address	Redfin Estimate
26 Deepwoods Road, Winhall, VT 5 Beds \| 2 Baths \| 1828 Sq. Ft.	$559,143
17 Deep Woods Road, Manchester Center, VT 4 Beds \| 2 Baths \| 1848 Sq. Ft.	$542,148
2 Old Beaver Pond Road, Winhall, VT 3 Beds \| 2 Baths \| 986 Sq. Ft.	$412,538
6 Deep Woods Road, Manchester Center, VT 3 Beds \| 1.5 Baths \| 1116 Sq. Ft.	$291,121
25 Deep Woods Circle, Manchester Center, VT 3 Beds \| 2 Baths \| 1201 Sq. Ft.	$519,794
21 Valley View Road, Winhall, VT 5 Beds \| 4.5 Baths \| 6512 Sq. Ft.	$1,626,364
6 Deep Woods Road #4, Winhall, VT 3 Beds \| 1.5 Baths \| 1116 Sq. Ft.	$356,183

Address	Redfin Estimate
25 Deepwoods Circle, Winhall, VT 3 Beds \| 2.5 Baths \| 2133 Sq. Ft.	$814,757
11 Little York Road, Winhall, VT 3 Beds \| 2.5 Baths \| 1952 Sq. Ft.	$617,682
26 Deep Woods Road, Manchester Center, VT 5 Beds \| 2 Baths \| 1476 Sq. Ft.	$493,542
9 Deep Woods Road, Manchester Center, VT 3 Beds \| 2.5 Baths \| 3115 Sq. Ft.	$658,328
24 Deep Woods Road, Manchester Center, VT 4 Beds \| 2 Baths \| 1260 Sq. Ft.	$428,295
7 Deep Woods Road, Manchester Center, VT 3 Beds \| 2 Baths \| 1592 Sq. Ft.	$531,809
6 Old Snow Valley Road, Winhall, VT 2 Beds \| 2 Baths \| 1416 Sq. Ft.	$360,088

Property information provided by PrimeMLS when last listed in 2018. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05255, VT

Sale history for 14 Deepwoods Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05340

Home values near 14 Deepwoods Rd

More real estate resources