OFF MARKET

Listed by Jeff Olson • BHHS Vermont Realty Group/Middlebury. Bought with Coldwell Banker Hickok and Boardman.

Off Market Jul 2022 for $608K

$725,397

Est. refi paymentEst. refi $3,869/mo

•

4,240

sq ft

20 Windy Rdg, Chittenden, VT 05737

About this home

Lovely, well-kept home that is part post and beam and part contemporary and built with high-quality materials. There are 3 bedrooms and 3 baths and PLENTY of space. This home and location will be heaven for outdoor enthusiasts--Mountain Top Resort and its great Nordic skiing are just up the road, and Killington and Pico are twenty minutes by car. Oh, and did we mention the Long Trail and a multitude of Green Mountain National Forest hiking/hunting/snowmobiling opportunities? Plus great fishing and kayaking at the nearby Chittenden Reservoir. You will love the large rear deck with Green Mountain views and the oversize garage for cars, toys, and space for your projects. A shed will contain your mower, gardening tools, bikes, and more. Bonus #1: The property come with a generator to keep things running in an outage. Bonus #2: Superb internet speed for entertainment and ease of working remotely. You want to get away from it all in comfort? Look no further. Note: Showings start 4/18/22

Single-familyProperty Type

1984Year Built

2.5 acresLot Size

$171Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Jeff Olson • BHHS Vermont Realty Group/Middlebury

Bought with C. Robin Hall • Coldwell Banker Hickok and Boardman

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4905431

Redfin Estimate

$725,397

$117K since sold in July 2022$21K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 43.5% higher than the average sale price ($505K) of 6 comparable homes.

SOLD AUG 7, 2026
$1,001,000
A
4 beds4.5 baths5,453 sq ft
127 Wynnridge Dr, Rutland, VT 05701
SOLD JUN 12, 2026
$581,950
B
3 beds3 baths2,372 sq ft
148 Pinnacle Ridge Rd, Rutland, VT 05701
SOLD JUL 13, 2026
$542,500
C
4 beds2.5 baths2,016 sq ft
16 Night Pasture Ln, S Chittenden, VT 05701
SOLD FEB 25, 2026
$480,000
D
3 beds2.5 baths2,184 sq ft
20 Pasquale Ln, Chittenden, VT 05737
SOLD MAR 11, 2026
$42,000
E
4 beds3 baths2,468 sq ft
1678 Sangamon Rd, Pittsford, VT 05763
SOLD JUL 2, 2026
$385,000
F
3 beds2.5 baths2,362 sq ft
180 David Rd, Rutland, VT 05701

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,457/mo

Redfin rental estimate

List your home for rent

Market trends in 05737, VT

Last updated July 2026

Sale-to-List Price

100.0%

0.0% MoM

Median sale price

$185K

$0 MoM

Avg. days on market

17d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

$449,000
3 beds2 baths1,320 sq ft
9 Birch Hill Rd, Chittenden, VT 05737
See all

Provided by Redfin

Sale history for 20 Windy Rdg

Date

Event

Price

PrimeMLS #4905431

Jul 6, 2022

Sold

$608,000

$143/sq ft

May 8, 2022

Pending

—

Apr 16, 2022

Listed

$625,000

$147/sq ft

PrimeMLS #4812962

Aug 25, 2020

Sold

$419,000

$99/sq ft

Jul 18, 2020

Contingent

—

Jun 25, 2020

Listed

$419,000

$99/sq ft

+19

Quality custom built Post and Beam country home with spacious rooms, natural light and a view. The many extras include a master suite with a balcony for watching the sun set, bathroom with Jacuzzi and a walk in closet for starters, 15'x32' deck with ramp and lovely yard for gardening. Welcome home to a 28'x32' two car garage with a work shop and direct entrance to a large mudroom, office space and exercise room. The first floor has a living room with a wood burning fireplace as well as an open hobby/play room with a beautiful wooden spiral staircase to the master bedroom suite above. A kitchen with an island and access to the front porch, dining room, den and half bathroom complete the first floor. Two more bedrooms and another full bathroom are down the hall from the master bedroom suite. This house has more than enough storage on each level, deck is off dining room, an outside shower, two heating systems, Kohler generator, storage shed and a great location - all within minutes to Killington, Rutland and Barstow School. What a great place to call home!

Public Records

Oct 12, 2006

Sold

$465,000

$110/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$7,522 (+3.2%)

$92,300 + $308,300

$400,600

2024

$7,290 (+14.2%)

$92,300 + $308,300

$400,600

2023

$6,386 (−26.8%)

$92,300 + $308,300

$400,600

2022

$8,723 (+0.8%)

$92,300 + $308,300

$400,600

2021

$8,654 (+7.2%)

$92,300 + $308,300

$400,600

2020

$8,074 (+6.3%)

$92,300 + $308,300

$400,600

2019

$7,599 (−5.5%)

$92,300 + $308,300

$400,600

2018

$8,038 (+5.6%)

$92,300 + $308,300

$400,600

2017

$7,615 (+4.9%)

$92,300 + $308,300

$400,600

2016

$7,258 (−2.7%)

$106,100 + $271,400

$377,500

2015

$7,462 (+109.4%)

$106,100 + $271,400

$377,500

2014

$3,564 (+497.0%)

$106,100 + $286,600

$392,700

2011

$597

$106,100 + $286,600

$392,700

Tax history for 20 Windy Rdg

Year

Property tax

Land + Additions

Assessment*

2025

$7,522 (+3.2%)

$92,300 + $308,300

$400,600

2024

$7,290 (+14.2%)

$92,300 + $308,300

$400,600

2023

$6,386 (−26.8%)

$92,300 + $308,300

$400,600

2022

$8,723 (+0.8%)

$92,300 + $308,300

$400,600

2021

$8,654 (+7.2%)

$92,300 + $308,300

$400,600

2020

$8,074 (+6.3%)

$92,300 + $308,300

$400,600

2019

$7,599 (−5.5%)

$92,300 + $308,300

$400,600

2018

$8,038 (+5.6%)

$92,300 + $308,300

$400,600

2017

$7,615 (+4.9%)

$92,300 + $308,300

$400,600

2016

$7,258 (−2.7%)

$106,100 + $271,400

$377,500

2015

$7,462 (+109.4%)

$106,100 + $271,400

$377,500

2014

$3,564 (+497.0%)

$106,100 + $286,600

$392,700

2011

$597

$106,100 + $286,600

$392,700

*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

2.5 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Rutland County

APN

14704610025

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Under
Heated
Parking Spaces 6+

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Interior
Stairs - Interior, Walkout, Interior Access

Other Interior Features
# of Rooms: 7
Level B: Exercise Room, Level B: Laundry Room, Level B: Media Room
Flooring: Carpet, Laminate, Tile, Wood
Water Heater: Off Boiler
Blinds, Ceiling Fan, Fireplaces - 1, Kitchen Island, Natural Light, Soaking Tub, Laundry - Basement, Smart Thermostat

Equipment & Appliance Information
Dishwasher, Dryer, Microwave, Refrigerator, Washer, Stove - Gas
Generator - Standby

Room 1 Information
Kitchen
Kitchen
Dimensions: 14' x 12'4"
Level: 1

Room 2 Information
Dining Room
Dimensions: 11'9" x 11'3"
Level: 1

Room 3 Information
Den
Dimensions: 14'4" x 13'10"
Level: 1

Room 4 Information
Living Room
Dimensions: 26'5" x 15'
Level: 1

Room 5 Information
Family Room
Dimensions: 19' x 14'6"
Level: 1

Room 6 Information
Bedroom
Bedroom
Dimensions: 17'4" x 15
Level: 2

Room 7 Information
Bedroom
Dimensions: 14'8" x 13'11"
Level: 2

Room 8 Information
Bedroom
Dimensions: 10'9" x 14'8"
Level: 2

Room 9 Information
Laundry Room
Dimensions: 16'7" x 6'
Level: Basement

Room 10 Information
Exercise Room
Dimensions: 17' x 10'6"
Level: Basement

Room 11 Information
Media Room
Dimensions: 12'11" x 15'4"
Level: Basement

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 4240
Approximate Sq. Ft. Total: 5984
Deck, Porch - Covered, Shed
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt
Exterior: Clapboard

Driveway
Paved

Lot, Zoning, & Easement Information
Easements: Unknown
Hilly, Open, Sloping

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1984
Water View: No
Water View: N
Waterfront: No
Water Body Access: No

Financial

Assessment Information
Assessment Amount: 400600
Assessment Year: 2017

Tax Information
Tax Year: 2021
Tax Year Notes: 2021-22
Gross Amount Tax: 8654.16
SPAN Number: 147-046-10025

Other Tax Information
Page Deed: 432

Financing Information
Possible Options: Cash, Conventional, FHA, VA

Utilities

Heating & Cooling Information
Heat: Baseboard, Furnace - Pellet
Heat Fuel: Oil, Pellet

Sewer Information
Septic

Electric Information
Electric Company: Green Mountain Power
Circuit Breaker(s)

Water Information
Drilled Well

Other Utilities Information
Cable - At Site, Telephone Available

Location

School Information
School District: Barstow Joint School District
Elementary School: Barstow Memorial School
Elementary School: Barstow Memorial School
Middle/Jr School: Barstow Memorial School

Neighborhood Information
Mountain, Near Skiing, Near Snowmobile Trails, Rural

Road Information
Road Frontage: TBD
Privately Maintained

Other Location Information
Directions: From Route 7 in Pittsford, head east on Sangamon Road. Turn north (left) on Chittenden Road. Turn left on Mountain Top Road; Windy Ridge is the third right.

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 2.5 acres
Style: Other
Year Built: —
Year Renovated: —
County: Rutland County
APN: 14704610025

Home facts updated by county records on Jul 15, 2026

Other

Water Body Information
Flood Zone: Unknown

Around this home

Schools

Barstow Memorial School

Public PreK-8 • Assigned • 1.2mi

6/10

Otter Valley Uhsd #8

Public 7-12 • Assigned • 6.5mi

2/10

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

4 days above 86° expected this year, 9 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

Chittenden, VT • 05737

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$690,000 – $835,000

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

Nearby similar homes

$140,000

Land— sq ft

220 Middle Rd, North Chittenden, VT 05763

$315,000

3 beds1 bath1,344 sq ft

135 Harrington Ave, Rutland, VT 05701

VIDEO TOUR

$4,500,000

20 beds20.5 baths15,684 sq ft

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Land— sq ft

29.5 Hillside Rd, Rutland, VT 05701

$345,000

3 beds1.5 baths1,212 sq ft

29 Clinton Ave, Rutland, VT 05701

$515,000

4 beds3 baths2,486 sq ft

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New listings for sale in 05737

$449,000

3 beds2 baths1,320 sq ft

9 Birch Hill Rd, Chittenden, VT 05737

Home values near 20 Windy Rdg

Data from public records.

Address	Redfin Estimate
19 Horton Hill, Chittenden, VT 3 Beds \| 2 Baths \| 1992 Sq. Ft.	$550,988
22 Horton Hill, Chittenden, VT 3 Beds \| 3 Baths \| 2974 Sq. Ft.	$722,766

Address	Redfin Estimate
47 Blue Ridge Road, Chittenden, VT 4 Beds \| 3.5 Baths \| 3400 Sq. Ft.	$631,237
8 Horton Hill, Chittenden, VT 3 Beds \| 2.5 Baths \| 1764 Sq. Ft.	$638,179

Address	Redfin Estimate
54 Blue Ridge Road, Chittenden, VT 2 Beds \| 3 Baths \| 1446 Sq. Ft.	$326,314
58 Blue Ridge Road, Chittenden, VT 4 Beds \| 2 Baths \| 1902 Sq. Ft.	$271,611

Property information provided by PrimeMLS when last listed in 2022. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05737, VT

Sale history for 20 Windy Rdg

Tax history for 20 Windy Rdg

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05737

Home values near 20 Windy Rdg

More real estate resources