OFF MARKET

Listed by Kaitlyn Hummel • Prestige Real Estate of Killington. Bought with Prestige Real Estate of Killington.

Off market dec 2024 for $340K

$417,272

Est. refi paymentEst. refi $2,261/mo

•

1,776

sq ft

303 Winding Way, Killington, VT 05751

About this home

Nestled at the top of a quiet dead-end road, this 4-bedroom, 2-bathroom single-family home sits on a generous +/- 1.23-acre lot offering privacy and seasonal mountain views. With spacious interiors and a serene setting, this property is brimming with potential for those ready to roll up their sleeves. Whether you're seeking a renovation project or envisioning creating your dream home, the possibilities are endless. This property is being sold "as is, " presenting a unique opportunity for investors or handy homeowners to unlock its full value. Don't miss your chance to own a piece of Vermont's beauty—schedule your viewing today!

Single-familyProperty Type

1970Year Built

1.23 acresLot Size

$235Est. Price/Sq.Ft.

Listed by Kaitlyn Hummel • Prestige Real Estate of Killington

Bought with Kaitlyn Hummel • Prestige Real Estate of Killington

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5023127

Redfin Estimate

$417,272

$77K since sold in December 2024$9,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 38.4% lower than the average sale price ($678K) of 6 comparable homes.

SOLD SEP 11, 2026
$500,000
A
4 beds2.5 baths2,019 sq ft
1724 Sangamon Rd, Pittsford, VT 05763
SOLD OCT 16, 2026
$450,000
B
3 beds3 baths1,786 sq ft
393 Tanglewood Dr, Killington, VT 05751
SOLD SEP 2, 2026
$760,000
C
4 beds4 baths2,392 sq ft
102 Spring Gln, Killington, VT 05751
SOLD NOV 21, 2025
$395,200
D
4 beds3 baths1,869 sq ft
33 Terra Ln, Mendon, VT 05701
SOLD JUL 31, 2026
$860,000
E
4 beds2 baths1,848 sq ft
309 Ladyslipper Ln, Killington, VT 05751
SOLD AUG 14, 2026
$1,100,000
F
3 beds2.5 baths2,152 sq ft
72 Telefon Trl, Killington, VT 05751

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Earn from this home

Refinance

Est. cash available

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Rent

$3,321/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

$50,000
Studio1 bath418 sq ft
228 E Mountain Rd Unit A HCP 159 II (HARRISON), Killington, VT 05751
$1,049,000
3 beds4 baths3,201 sq ft
202 Burke Holw Unit D2, Killington, VT 05751
See all

Provided by Redfin

Sale history for 303 Winding Way

Date

Event

Price

PrimeMLS #4

Oct 5, 2026

Price Changed

$579,900

$327/sq ft

Sep 28, 2026

Price Changed

$589,900

$332/sq ft

Sep 23, 2026

Price Changed

$599,900

$338/sq ft

Sep 2, 2026

Price Changed

$615,900

$347/sq ft

Aug 27, 2026

Price Changed

$624,900

$352/sq ft

Aug 12, 2026

Price Changed

$649,500

$366/sq ft

Jul 9, 2026

Price Changed

$629,000

$354/sq ft

Jun 17, 2026

Price Changed

$549,900

$310/sq ft

PrimeMLS #3

May 6, 2026

Price Changed

$569,000

$320/sq ft

Apr 25, 2026

Price Changed

$574,000

$323/sq ft

Apr 7, 2026

Price Changed

$579,000

$326/sq ft

PrimeMLS #2

Nov 6, 2025

Price Changed

$574,500

$323/sq ft

Oct 31, 2025

Price Changed

$584,500

$329/sq ft

Oct 23, 2025

Price Changed

$599,900

$338/sq ft

Oct 10, 2025

Price Changed

$619,900

$349/sq ft

Sep 29, 2025

Price Changed

$644,900

$363/sq ft

Aug 26, 2025

Price Changed

$589,900

$332/sq ft

PrimeMLS #1

Feb 26, 2025

Price Changed

$459,900

$259/sq ft

Feb 23, 2025

Price Changed

$474,900

$267/sq ft

PrimeMLS #5023127

Dec 24, 2024

Sold

$340,000

$191/sq ft

Nov 28, 2024

Contingent

—

Nov 25, 2024

Listed

$360,000

$203/sq ft

Tax history for 303 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

—

Stories

—

Lot width

—

Lot depth

—

Lot size

1.23 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Rutland County

APN

58818510199

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Interior

Virtual Tour

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

Other Interior Features
# of Rooms: 6
Flooring: Carpet, Combination, Laminate
Dining Area, Natural Light, Vaulted Ceiling, Laundry - 2nd Floor

Equipment & Appliance Information
Dishwasher, Dryer, Microwave, Refrigerator, Washer, Stove - Gas, Water Heater - Electric

Exterior

Building Information
Architectural Style: Contemporary, Multi-Level, Walkout Lower Level
Construction Status: Existing
Construction Materials: Wood Frame
Approximate Sq. Ft. Total Finished: 1776
Approximate Sq. Ft. Total: 1776
Deck
Foundation: Concrete
Roof: Shingle - Asphalt

Driveway
Dirt

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

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1970

Financial

Tax Information
Tax Year: 2024
Gross Amount Tax: 7226.79
SPAN Number: 588-185-10199

Other Tax Information
Page Deed: 19-22

Utilities

Heating & Cooling Information
Heat: Baseboard, Electric, Stove - Gas

Sewer Information
Septic

Electric Information
Circuit Breaker(s)

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: None, Unknown
Gas - LP/Bottle

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: TBD

Other Location Information
Directions: Route 100 to Doubleday Hill Road, slight left turn onto Winding way, .2 miles keep right onto Winding way, property will be in .3 miles on your left.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 1.23 acres
Style: Other
Year Built: —
Year Renovated: —
County: Rutland County
APN: 58818510199

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Killington Elementary School

Public PreK-6 • Assigned • 4.4mi

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

82/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Killington. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

7.5 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$397,000 – $480,000

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

Nearby similar homes

VIDEO TOUR

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Land— sq ft

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New listings for sale in 05751

$50,000

Studio1 bath418 sq ft

228 E Mountain Rd Unit A HCP 159 II (HARRISON), Killington, VT 05751

$1,049,000

3 beds4 baths3,201 sq ft

202 Burke Holw Unit D2, Killington, VT 05751

Home values near 303 Winding Way

Data from public records.

Address	Redfin Estimate
220 Winding Way, Killington, VT 3 Beds \| 2.5 Baths \| - Sq. Ft.	$735,187
150 Winding Way, Killington, VT 3 Beds \| 2 Baths \| 1460 Sq. Ft.	$539,807

Address	Redfin Estimate
94 Winding Way, Killington, VT 2 Beds \| 2.5 Baths \| 2245 Sq. Ft.	$613,838
230 Winding Way, Killington, VT 3 Beds \| 4.5 Baths \| 5272 Sq. Ft.	$2,061,293

Address	Redfin Estimate
122 Winding Way, Killington, VT 4 Beds \| 3 Baths \| 3726 Sq. Ft.	$971,254
Winding Way, Killington, VT - Beds \| - Baths \| - Sq. Ft.	—

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

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05751, VT

Sale history for 303 Winding Way

Tax history for 303 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 303 Winding Way

More real estate resources