OFF MARKET

Listed by Peggy Steves • Four Seasons Sotheby's Int'l Realty. Bought with Kelley Real Estate, Inc.

Off market apr 2021 for $450K

$943,352

Est. refi paymentEst. refi $3,020/mo

•

3,726

sq ft

122 Winding Way, Killington, VT 05751

About this home

This one of a kind home offers everything a family is looking for, whether it is your primary residence or your second home close to Killington and Pico ski resorts. This home features a spacious 43’ X 32’ great room for the entire family to gather and watch movies or play a game of pool. The propane fireplace keeps the space very warm and cozy in the winter months. The great room also features an oversized work space for everyone’s computer. Ideal for working from home or home schooling. The master bedroom has a long hallway that leads to its seclusion. Awaiting after a long day on the slopes is a hot tub room to enjoy and relax. The kitchen offers a large dining area, which leads directly onto the deck for additional entertaining. Also, this home has two large walk-in pantries for all of your kitchen appliances and more. The lower level offers an efficiency kitchen, living room, full bath and large bedroom that could sleep many. Your guests will love having their own space on the lower level or this could be used as lucrative rental space. The best feature of this home in addition to the three-car heated garage and whole house generator is the over 1000 square feet of sunny, south-facing decks with views of Killington and Pico mountains. If you are looking for a home with lots of room for family and friends and just minutes to ski slopes, golf, hiking, and mountain biking then you will want to see this home. Call today for an appointment.

Single-familyProperty Type

1972Year Built

1.25 acresLot Size

$253Est. Price/Sq.Ft.

3 car garageParking

Listed by Peggy Steves • Four Seasons Sotheby's Int'l Realty

Bought with Sean Williams • Kelley Real Estate, Inc.

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4846084

Redfin Estimate

$943,352

$493K since sold in April 2021$18K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 48.5% higher than the average sale price ($635K) of 6 comparable homes.

SOLD SEP 2, 2026
$760,000
A
4 beds4 baths2,392 sq ft
102 Spring Gln, Killington, VT 05751
SOLD SEP 11, 2026
$500,000
B
4 beds2.5 baths2,019 sq ft
1724 Sangamon Rd, Pittsford, VT 05763
SOLD JUN 12, 2026
$1,275,000
C
3 beds4.5 baths2,867 sq ft
520 Barrows Towne Rd, Killington, VT 05751
SOLD SEP 25, 2026
$699,000
D
6 beds3.5 baths2,496 sq ft
144 Floral Dr, Killington, VT 05751
SOLD MAR 11, 2026
$42,000
E
4 beds3 baths2,468 sq ft
1678 Sangamon Rd, Pittsford, VT 05763
SOLD FEB 13, 2026
$535,000
F
4 beds2.5 baths2,407 sq ft
505 Cedarwood Rd, Stockbridge, VT 05772

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Earn from this home

Refinance

Est. cash available

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Rent

$2,548/mo

Redfin rental estimate

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Market trends in 05751, VT

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.6%

0.3% MoM

Median sale price

$501K

$15K MoM

Avg. days on market

51d

8 days MoM

Recently sold homes

2 MoM

New listings for sale

NEW 18 HRS AGO
$1,049,000
3 beds4 baths3,201 sq ft
202 Burke Holw Unit D2, Killington, VT 05751
$649,000
3 beds2 baths1,300 sq ft
51 E Glade at Sunrise Unit B2, Killington, VT 05751
$900,000
5 beds3 baths3,537 sq ft
219 Alpine Dr, Killington, VT 05751
$989,000
3 beds2 baths2,278 sq ft
57 Doubleday Hill Rd, Killington, VT 05751
3D & VIDEO TOUR
$810,000
3 beds3 baths3,258 sq ft
183 Southview Path, Killington, VT 05751
$585,000
3 beds1.5 baths1,168 sq ft
768 E Mountain Rd Unit C2, Killington, VT 05751
See all

Provided by Redfin

Sale history for 122 Winding Way

Date

Event

Price

PrimeMLS #4846084

Apr 30, 2021

Sold

$450,000

$121/sq ft

Feb 15, 2021

Pending

—

Feb 3, 2021

Listed

$425,000

$114/sq ft

PrimeMLS #4683299

Aug 17, 2018

Sold

$360,000

$97/sq ft

Jun 18, 2018

Contingent

—

Mar 29, 2018

Listed

$379,000

$102/sq ft

+22

This expansive contemporary home started life in 1972 as a classic Austrian-style chalet with vaulted ceilings and exposed beams. After several renovations and the 2009 addition of a 3-car garage with an enormous great room above, this spectacular property offers something for everyone today. For the chef in the household, the kitchen features stainless appliances, tile floors, attractive pine ceilings and a convenient peninsula-style island. A brand new hot tub room, located off the master bedroom suite is the perfect place to relax any time of year. The spacious great room is ideal for entertaining and with a second full kitchen on the lower level, there is potential for an in-law suite or a lucrative AirBnB rental. Over 1000 square feet of sunny, south-facing decks with views of Killington and Pico add to the allure of this very special residence. If you're looking for a largely updated home with room for friends and family and just minutes to skiing, golf and mountain biking, you'll want to see this property. Call today for an appointment.

PrimeMLS #1

Dec 29, 2016

Price Changed

$429,000

$115/sq ft

PrimeMLS #807102

Oct 26, 2001

Sold

$159,000

$43/sq ft

Sep 1, 2001

Delisted

—

Jun 3, 2001

Listed

$159,000

$43/sq ft

Tax history for 122 Winding Way

*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

1.5

Stories

Lot width

—

Lot depth

—

Lot size

1.25 Acres

Year renovated

—

Sq. Ft.

2,362

Year built

1966

Style

Single Family Residential

County

Rutland County

APN

58818510203

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 3
Location: Attached
Heated

Interior

Bathroom Information
# of Baths (full): 3

Other Interior Features
# of Rooms: 10
Flooring: Carpet, Combination, Laminate, Tile
Water Heater: Gas - Liquid Propane Bottle
Cathedral Ceiling, Ceiling Fan, Dining Area, Hot Tub, In-Law Suite, Kitchen/Dining, Master Bedroom With Bath, Natural Light, Vaulted Ceiling, Walk-in Pantry

Equipment & Appliance Information
Dishwasher, Microwave, Range - Gas, Refrigerator
Window AC, Stove-Gas, Generator - Standby

Room 1 Information
Kitchen
Kitchen
Level: 1

Room 2 Information
Family Room
Level: 1

Room 3 Information
Bedroom
Level: 1

Room 4 Information
Full Bath
Level: 1

Room 5 Information
Laundry Room
Level: 1

Room 6 Information
Kitchen/Dining
Kitchen/Dining
Level: 2

Room 7 Information
Living Room
Level: 2

Room 8 Information
Master Bedroom Suite
Level: 2

Room 9 Information
Full Bath
Level: 2

Room 10 Information
Other
Level: 2

Room 11 Information
Full Bath
Level: 2

Room 12 Information
Great Room
Level: 2

Room 13 Information
Full Bath
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 3726
Approximate Sq. Ft. Total: 3726
Deck, Garden Space, Outbuilding
Construction: Post and Beam, Wood Frame
Foundation: Concrete
Roof: Metal, Standing Seam
Exterior: Wood Siding

Driveway
Crushed Stone

Lot, Zoning, & Easement Information
Mountain View

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1972

Financial

Tax Information
Tax Year: 2020
Gross Amount Tax: 6937.83
SPAN Number: 588-185-10203
Taxes TBD: Yes

Other Tax Information
Page Deed: 567-571

Utilities

Heating & Cooling Information
Cooling: Wall AC Units
Heat: Direct Vent
Heat Fuel: Gas - Liquid Propane Bottle

Sewer Information
Septic

Electric Information
Circuit Breaker(s)

Water Information
Drilled Well

Other Utilities Information
Cable, Internet - Cable

Location

Road Information
Road Frontage: Yes
Road Frontage Length: 152
Gravel, Public

Other Location Information
Directions: US 4/Woodstock Ave from Rutland, turn left onto VT-100 East, Turn Right onto Doubleday Hill Road, then first left, follow and then turn right onto Winding Way. House is second on the right.

Public facts

Beds: 3
Baths: 1.5
Sq. Ft.: 2,362
Stories: 1.0
Lot Size: 1.25 acres
Style: Single Family Residential
Year Built: 1966
Year Renovated: —
County: Rutland County
APN: 58818510203

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Killington Elementary School

Public PreK-6 • Assigned • 4.3mi

9/10

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

7 days above 86° expected this year, 18 days in 30 years

3/10 Wind Factor

4% chance of strong winds in next 30 years

1/10 Air Factor

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

Provided by First Street

Historical weather

Killington, VT • 05751

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 3.2 hours in December, placing it below the U.S. average for solar exposure.

8.3 hrs

3.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$897,000 – $1.09M

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

Nearby similar homes

$140,000

Land— sq ft

220 Middle Rd, North Chittenden, VT 05763

$345,000

3 beds2 baths1,729 sq ft

15 Victor Pl, Rutland, VT 05701

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3 beds3 baths2,697 sq ft

1641 W Hill Rd, Rochester, VT 05767

$599,000

Studio0.5 baths2,971 sq ft

3471 Route 4, Killington, VT 05751

$445,000

4 beds1.5 baths3,499 sq ft

32 North St, Rutland, VT 05701

$498,000

4 beds2 baths1,344 sq ft

120 Rustic Dr, Killington, VT 05751

New listings for sale in 05751

NEW 18 HRS AGO

$1,049,000

3 beds4 baths3,201 sq ft

202 Burke Holw Unit D2, Killington, VT 05751

$649,000

3 beds2 baths1,300 sq ft

51 E Glade at Sunrise Unit B2, Killington, VT 05751

$900,000

5 beds3 baths3,537 sq ft

219 Alpine Dr, Killington, VT 05751

$989,000

3 beds2 baths2,278 sq ft

57 Doubleday Hill Rd, Killington, VT 05751

3D & VIDEO TOUR

$810,000

3 beds3 baths3,258 sq ft

183 Southview Path, Killington, VT 05751

$585,000

3 beds1.5 baths1,168 sq ft

768 E Mountain Rd Unit C2, Killington, VT 05751

Home values near 122 Winding Way

Data from public records.

Address	Redfin Estimate
220 Winding Way, Killington, VT 3 Beds \| 2.5 Baths \| - Sq. Ft.	$733,842
Winding Way, Killington, VT - Beds \| - Baths \| - Sq. Ft.	—

Address	Redfin Estimate
94 Winding Way, Killington, VT 2 Beds \| 2.5 Baths \| 2245 Sq. Ft.	$613,550
15 Winding Way, Killington, VT 4 Beds \| 1.5 Baths \| 2402 Sq. Ft.	$612,249

Address	Redfin Estimate
150 Winding Way, Killington, VT 3 Beds \| 2 Baths \| 1460 Sq. Ft.	$529,523
21 Jordan Dr, Killington, VT 3 Beds \| 1 Baths \| 1266 Sq. Ft.	$420,326

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

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About this home

Redfin Estimate

Earn from this home

Market trends in 05751, VT

Sale history for 122 Winding Way

Tax history for 122 Winding Way

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05751

Home values near 122 Winding Way

More real estate resources