OFF MARKET

Listed by Krista Mosher • Killington Pico Realty. Bought with Ski Country Real Estate.

Off market jan 2025 for $1.6M

$2,053,362

Est. refi paymentEst. refi $10,806/mo

•

5,272

sq ft

230 Winding Way, Killington, VT 05751

About this home

This exquisite 3-bedroom, 2 sizeable bonus guest rooms, and 4.5-bathroom residence is an impeccably designed and maintained masterpiece of craftsmanship and luxury. Winding Way is an elegant mountain home nestled on 10 private acres in the scenic beauty of Killington, Vermont, just minutes from world-class skiing and mountain biking. Boasting unparalleled views of Killington and Pico from multiple vantage points, an immaculate floor to ceiling stone fireplace and vaulted ceilings, walls of windows that flood the home with natural light and plenty of open space for guests. Perfect for culinary enthusiasts and entertaining guests, the gourmet kitchen features top of the line appliances including a sub-zero refrigerator, Bosch dishwasher, industrial Viking stove, Vermont Verde marble countertops and custom cabinetry as well as an elevated fireplace for ultimate ambiance. A fully equipped butler’s pantry, expansive dining room and cold pantry make dinner parties and entertaining a dream. The two ensuites feature Vermont Danby white marble, luxurious steam showers, jacuzzi tubs and radiantly heated floors for full relaxation after a day on the slopes, or you can decompress while playing pool on the billiards table. An expansive mud room directly attached to the one-car garage makes it easy to store your gear, keeping it warm and dry for your next epic day. Call today to schedule a private tour to experience the luxury, craftsmanship, and stunning views that define this property.

Single-familyProperty Type

1985Year Built

10.1 acresLot Size

$389Est. Price/Sq.Ft.

1 car garageParking

Listed by Krista Mosher • Killington Pico Realty

Bought with Katie McFadden • Ski Country Real Estate

Redfin checked: a minute ago

•Source:PrimeMLS #4986558

Redfin Estimate

$2,053,362

$403K since sold in January 2025$18K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 159.5% higher than the average sale price ($791K) of 6 comparable homes.

SOLD SEP 25, 2026
$375,000
A
3 beds2.5 baths2,276 sq ft
8 Charter Hill Dr, Rutland, VT 05701
SOLD JUN 12, 2026
$1,275,000
B
3 beds4.5 baths2,867 sq ft
520 Barrows Towne Rd, Killington, VT 05751
SOLD OCT 9, 2026
$885,000
C
3 beds3.5 baths2,112 sq ft
142 Old Coach Rd, Killington, VT 05751
SOLD OCT 13, 2026
$662,500
D
3 beds2.5 baths3,390 sq ft
314 Killington Ave, Rutland, VT 05701
SOLD AUG 14, 2026
$1,100,000
E
3 beds2.5 baths2,152 sq ft
72 Telefon Trl, Killington, VT 05751
SOLD OCT 16, 2026
$450,000
F
3 beds3 baths1,786 sq ft
393 Tanglewood Dr, Killington, VT 05751

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Earn from this home

Refinance

Est. cash available

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Rent

$1,849/mo

Redfin rental estimate

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Market trends in 05751, VT

Last updated October 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

$435,000
1 bed2 baths927 sq ft
112 High Ridge Rd Unit D 13, Killington, VT 05751
$559,000
4 beds3 baths1,776 sq ft
303 Winding Way, Killington, VT 05751
$429,000
3 beds2 baths881 sq ft
697 E Mountain Rd Unit A 4, Killington, VT 05751
3D WALKTHROUGH
$399,000
2 beds1 bath652 sq ft
907 E Mountain Rd Unit H-4, Killington, VT 05751
$799,000
3 beds2 baths1,344 sq ft
777 Roaring Brook Rd, Killington, VT 05751
See all

Provided by Redfin

Sale history for 230 Winding Way

Tax history for 230 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

10.1 Acres

Year renovated

—

Sq. Ft.

896

Year built

1930

Style

Single Family Residential

County

Rutland County

APN

58818510114

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 23, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 1
Direct Entry, Garage, On-Site, Other, Attached

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Interior
Finished

Other Interior Features
# of Rooms: 13
Flooring: Hardwood, Marble, Tile
Cathedral Ceiling, Dining Area, Fireplace - Wood, Fireplaces - 2, Kitchen Island, Kitchen/Dining, Master Bedroom With Bath, Vaulted Ceiling, Walk-in Pantry, Laundry - 1st Floor

Equipment & Appliance Information
Water Heater - Off Boiler

Room 1 Information
Mudroom
Mudroom
Dimensions: 13 X 14
Level: 1

Room 2 Information
Rec Room
Dimensions: 22 X 18
Level: 1

Room 3 Information
Master Bedroom
Dimensions: 21 X 13
Level: 1

Room 4 Information
Full Bath
Dimensions: 13 X 12
Level: 1

Room 5 Information
Full Bath
Dimensions: 7 X 9
Level: 1

Room 6 Information
Bedroom
Bedroom
Dimensions: 12 X 19
Level: 1

Room 7 Information
Foyer
Dimensions: 16 X 14
Level: 2

Room 8 Information
Great Room
Dimensions: 34 X 28
Level: 2

Room 9 Information
Dining Room
Dimensions: 16 X 11
Level: 1

Room 10 Information
Eat-In Kitchen
Dimensions: 20 X 33
Level: 2

Room 11 Information
Full Bath
Dimensions: 11 X 5
Level: 2

Room 12 Information
Bonus Room
Dimensions: 12 X 11
Level: 2

Room 13 Information
Bonus Room
Dimensions: 12 X 11
Level: 2

Room 14 Information
1/2 Bath
Dimensions: 5 X 5
Level: 2

Room 15 Information
Loft
Dimensions: 16 X 11
Level: 3

Room 16 Information
Master Bedroom Suite
Dimensions: 16 X 14
Level: 3

Room 17 Information
Full Bath
Dimensions: 10 X 15
Level: 3

Room 18 Information
Loft
Dimensions: 11 X 20
Level: 3

Exterior

Building Information
Architectural Style: Contemporary
Construction Status: Existing
Construction Materials: Shake Siding
Approximate Sq. Ft. Total Finished: 5272
Approximate Sq. Ft. Total: 5272
Color: Brown
Foundation: Poured Concrete
Roof: Shingle - Asphalt

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot Features: Mountain View

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1985

Financial

Tax Information
Tax Year: 2024
Gross Amount Tax: 18417.63
SPAN Number: 588-185-10114

Other Tax Information
Page Deed: 383-386

Utilities

Heating & Cooling Information
Heat: Baseboard, Radiant Floor

Sewer Information
Private

Electric Information
Electric Company: Green Mountain Power
100 Amp

Water Information
Water Source: Drilled Well, Private

Other Utilities Information
Internet: Internet - Cable
Fuel Company: CV Oil
Cable

Location

School Information
Elementary School: Killington Elementary School
Elementary School: Killington Elementary School
Middle/Jr School: Woodstock Union Middle School
School - High: Woodstock Union High School

Road Information
Road Frontage: Yes
Road Frontage Length: 648

Other Location Information
Directions: Route 100 to Doubleday Hill, veer left onto Rustic Dr. then veer right onto Winding Way. Property is on the right hand side - see the skis and house number on the tree at the beginning of the driveway.

Public facts

Beds: 2
Baths: 1.5
Sq. Ft.: 896
Stories: 2.0
Lot Size: 10.1 acres
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Rutland County
APN: 58818510114

Home facts updated by county records on Oct 23, 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, 16 days in 30 years

2/10 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

$1.95M – $2.36M

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

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Home values near 230 Winding Way

Data from public records.

Address	Redfin Estimate
303 Winding Way, Killington, VT 4 Beds \| 3 Baths \| 1776 Sq. Ft.	$557,914
122 Winding Way, Killington, VT 4 Beds \| 3 Baths \| 3726 Sq. Ft.	$974,270

Address	Redfin Estimate
220 Winding Way, Killington, VT 3 Beds \| 2.5 Baths \| - Sq. Ft.	$746,565
150 Winding Way, Killington, VT 3 Beds \| 2 Baths \| 1460 Sq. Ft.	$541,333

Address	Redfin Estimate
94 Winding Way, Killington, VT 2 Beds \| 2.5 Baths \| 2245 Sq. Ft.	$618,456
15 Winding Way, Killington, VT 4 Beds \| 1.5 Baths \| 2402 Sq. Ft.	$707,148

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

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