OFF MARKET

Listed by Betsy Cetron • Stratton Real Estate. Bought with Josiah Allen Real Estate, Manchester Branch Office.

Off Market Nov 2021 for $2.7M

$3,465,020

•

7,562

sq ft

69 Upper Taylor Hill Rd, Winhall, VT 05340

About this home

Stunning country home only minutes to Stratton's base area. Meticulously constructed with careful attention to details and materials it is privately sited on 11 + acres with dramatic views to Bromley, Magic & Okemo. Extensive landscaping. Great room with massive stone fireplace, soaring ceiling and windows to enjoy the expansive view. Kitchen offers all the amenities for the most discerning chef. Large walk-in pantry and large 900+ refrigerated walk in wine room. Quiet space in lovely den with fireplace. 6 ensuite bedrooms and 2 ensuite bunk rooms with custom built-in beds. Master suite has propane fireplace, access to enclosed porch and spa like bath. Large family room with fireplace and access to out door patio with hot tub plus additional game room. Lovely wood floors (Hickory, Pine, walnut) Large partially covered patio with built in grill and out door fireplace. Custom built shed to store wood, tools and toys. Partially furnished list to be provided. An Exceptional property at Stratton - offered for the first time.

Single-familyProperty Type

2009Year Built

11.55 acresLot Size

$458Est. Price/Sq.Ft.

3 car garageParking

Listed by Betsy Cetron • Stratton Real Estate

Bought with Joseph Cajzer • Josiah Allen Real Estate, Manchester Branch Office

Redfin checked: a minute ago

•Source:PrimeMLS #4848381

Redfin Estimate

$3,465,020

$765K since sold in November 2021$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 60.9% higher than the average sale price ($2.15M) of 6 comparable homes.

SOLD SEP 25, 2025
$2,250,000
A
8 beds8.5 baths6,471 sq ft
69 Upper Taylor Hill Rd Unit D, Winhall, VT 05340
SOLD MAY 22, 2026
$2,850,000
B
4 beds6 baths5,082 sq ft
41 Stark Farm Rd, Winhall, VT 05340
SOLD AUG 31, 2026
$1,100,000
C
3 beds4 baths2,745 sq ft
65 Lower Taylor Hill Rd, Winhall, VT 05340
SOLD MAR 31, 2026
$3,025,000
D
6 beds5 baths6,437 sq ft
67 High Meadow Rd, Winhall, VT 05340
SOLD FEB 12, 2026
$2,150,000
E
4 beds4.5 baths5,000 sq ft
16 Hunters Rdg, Winhall, VT 05340
SOLD APR 10, 2026
$1,550,000
F
5 beds4 baths4,000 sq ft
147 High Meadow Rd #147, Winhall, VT 05340

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Earn from this home

Rent

$2,899/mo

Redfin rental estimate

List your home for rent

Market trends in 05340, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.2%

+0.7% MoM

Median sale price

$799K

$64K MoM

Avg. days on market

80d

3 days MoM

Recently sold homes

1 MoM

New listings for sale

3D & VIDEO TOUR
$1,050,000
4 beds4 baths2,380 sq ft
20 W Branch Rd, Winhall, VT 05340
3D WALKTHROUGH
$749,000
3 beds2 baths976 sq ft
7 Woodrock Rd, Winhall, VT 05340
$1,325,000
4 beds3.5 baths3,400 sq ft
11 Round Tree Rd, Winhall, VT 05340
OPEN SAT, 12PM TO 2PM
$599,000
3 beds2 baths1,890 sq ft
33 Burnt Hill Rd, Winhall, VT 05340
$345,000
2 beds2 baths960 sq ft
19 Winhall Condo Rd #4, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 69 Upper Taylor Hill Rd

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

771-245-12238

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Apr 26, 2023.

Property details

Parking

Parking & Garage
Garage Capacity: 3
Location: Attached
Garage

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 8
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Climate Controlled, Finished, Stairs - Interior, Walkout, Interior Access, Exterior Access

Other Interior Features
# of Rooms: 14
Level B: Bedroom, Level B: Bonus Room, Level B: Family Room
Flooring: Carpet, Hardwood, Slate/Stone, Softwood, Tile, Wood
Water Heater: Free Standing, Owned
Blinds, Cathedral Ceiling, Dining Area, Draperies, Fireplace - Gas, Fireplace - Screens/Equip, Fireplace - Wood, Fireplaces - 3+, Furnished, Hot Tub, Kitchen Island, Kitchen/Dining, Living/Dining, Master Bedroom With Bath, Natural Woodwork, Security, Soaking Tub, Surrond Sound Wiring, Vaulted Ceiling, Walk-in Closet, Walk-in Pantry, Wet Bar, Whirlpool Tub, Window Treatment, Laundry - 1st Floor, Laundry - Basement

Equipment & Appliance Information
Cooktop - Gas, Dishwasher, Dryer - Energy Star, Exhaust Hood, Microwave, Mini Fridge, Oven - Double, Oven - Wall, Refrigerator-Energy Star, Washer - Energy Star, Warming Drawer
Security System, Generator - Standby

Room 1 Information
Great Room
Great Room
Dimensions: 24 x25
Level: 1

Room 2 Information
Dining Room
Dimensions: 17 x 19
Level: 1

Room 3 Information
Kitchen
Dimensions: 17 x 17
Level: 1

Room 4 Information
Den
Dimensions: 14 x 14
Level: 1

Room 5 Information
Master Bedroom Suite
Dimensions: 16 x 17
Level: 1

Room 6 Information
Mudroom
Mudroom
Dimensions: 11 x 15
Level: 1

Room 7 Information
Porch
Dimensions: 17 x 13
Level: 1

Room 8 Information
Porch
Dimensions: 18 x 15
Level: 1

Room 9 Information
Bedroom
Dimensions: 15 x 16
Level: 2

Room 10 Information
Bedroom
Dimensions: 13 x 15
Level: 2

Room 11 Information
Bedroom
Dimensions: 15 x 17
Level: 2

Room 12 Information
Bedroom
Dimensions: 16 x 17
Level: Basement

Room 13 Information
Bedroom
Dimensions: 16 x15
Level: Basement

Room 14 Information
Family Room
Dimensions: 25 x 26
Level: Basement

Room 15 Information
Bedroom
Dimensions: 12 x 14
Level: Basement

Room 16 Information
Bedroom
Dimensions: 12 x14
Level: Basement

Room 17 Information
Bonus Room
Dimensions: 12.5 x 18.5
Level: Basement

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 7562
Approximate Sq. Ft. Total: 7562
Color: Beige
Deck, Hot Tub, Outbuilding, Patio, Porch, Porch - Enclosed, Window Screens, Built in Gas Grill
Construction: Wood Frame
Foundation: Concrete
Roof: Metal, Shingle - Wood, Standing Seam
Exterior: Shingle, Stone, Wood, Wood Siding

Driveway
Gravel

Lot, Zoning, & Easement Information
Country Setting, Mountain View, Secluded, Sloping, View, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 2009

Financial

Tax Information
Tax Year: 2021
Gross Amount Tax: 36655.22
SPAN Number: 771-245-12238

Other Tax Information
Page Deed: 451

Utilities

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

Sewer Information
Septic

Electric Information
At Street, Generator

Water Information
Drilled Well, Private

Other Utilities Information
Cable Company: Comcast
Phone, Cable, Gas - LP/Bottle, Internet - Cable, Underground Utilities

Location

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

Road Information
Paved, Public

Other Location Information
Directions: Upper Taylor Hill Road - Left just past Hollow View Road, Right fork

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Bennington County
APN: 771-245-12238

Home facts updated by county records on Apr 25, 2023

Around this home

Schools

Mountain School At Winhall

Private K-8 • 1.3mi

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, 19 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

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 8.2 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

$3.29M – $3.99M

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

Nearby similar homes

$549,000

4 beds2.5 baths2,359 sq ft

116 Teacher Rd, Jamaica, VT 05343

VIDEO TOUR

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Studio1 bath950 sq ft

109 Winhall Hollow Rd, Winhall, VT 05340

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447 Rock Bottom Ln, Peru, VT 05255

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5 beds2 baths2,050 sq ft

1649 E Manchester Rd, Manchester Center, VT 05255

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13 Golden Triangle Rd, Winhall, VT 05340

OPEN SEP 7, 11AM TO 1PM

$850,000

4 beds3.5 baths3,154 sq ft

157 Old Sawmill Rd, Londonderry, VT 05148

New listings for sale in 05340

3D & VIDEO TOUR

$1,050,000

4 beds4 baths2,380 sq ft

20 W Branch Rd, Winhall, VT 05340

3D WALKTHROUGH

$749,000

3 beds2 baths976 sq ft

7 Woodrock Rd, Winhall, VT 05340

$1,325,000

4 beds3.5 baths3,400 sq ft

11 Round Tree Rd, Winhall, VT 05340

OPEN SAT, 12PM TO 2PMVIDEO TOUR

$599,000

3 beds2 baths1,890 sq ft

33 Burnt Hill Rd, Winhall, VT 05340

$345,000

2 beds2 baths960 sq ft

19 Winhall Condo Rd #4, Winhall, VT 05340

Home values near 69 Upper Taylor Hill Rd

Data from public records.

Address	Redfin Estimate
67 Upper Taylor Hill Road, Jamaica, VT 3 Beds \| 4 Baths \| 2644 Sq. Ft.	$918,416
67 Upper Taylor Hill Road, Winhall, VT 4 Beds \| 3 Baths \| 3552 Sq. Ft.	$924,303

Address	Redfin Estimate
69 Upper Taylor Hill Road, Winhall, VT 4 Beds \| 4.5 Baths \| 6471 Sq. Ft.	$2,837,478
69 Upper Taylor Hill Road #D, Winhall, VT 8 Beds \| 8.5 Baths \| 6471 Sq. Ft.	$2,799,506

Address	Redfin Estimate
57 Upper Taylor Hill Road, Winhall, VT 5 Beds \| 5.5 Baths \| 6479 Sq. Ft.	$1,910,059
119 Benson Fuller Drive, Winhall, VT 2 Beds \| 1 Baths \| 1596 Sq. Ft.	$449,098

Property information provided by PrimeMLS when last listed in 2021. This data may not match . Learn more.

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