SOLD OCT 29, 2026

Listed by Marni Rieger • KW Vermont-Killington (Cell: 802-353-1604). Bought with Four Seasons Sotheby's Int'l Realty.

Sold on oct 2026

$500,000

•

1,680

sq ft

105 Upper Round Top Ext, Plymouth, VT 05056

Track this home’s value and nearby sales activity

About this home

MINUTES TO KILLINGTON, OKEMO OR WOODSTOCK! IMMEDIATE ACCESS TO SNOWMOBILING AND HIKING/MOUNTAIN BIKING FROM YOUR DOOR! This totally renovated open concept 4 bedroom/ 2 bath contemporary chalet is being sold beautifully furnished and totally turn key! Move right in and begin to enjoy this fabulous home. The home offers a spacious floor plan perfect for entertaining. Walk in the home to a brand new mudroom with plenty of storage. Great kitchen that flows into an open dining and living area with wall of glass to enjoy the tranquil views. Living area has handsome stone hearth and gas fireplace. The lower level has an extra living/ hang out room for family and friends to stretch out. Large deck with hot tub. Relax by the firepit at night and soak in the stars and no light pollution! Sweet seasonal mountain views! Strong rental potential, excellent investment in the heart of ski and snowmobile country! Two snowmobiles convey with the sale.

Single-familyProperty Type

1975Year Built

0.44 acresLot Size

$298Price/Sq.Ft.

$46/moHOA Dues

Listed by Marni Rieger • KW Vermont-Killington

Contact: Cell: 802-353-1604

Bought with Merisa Sherman • Four Seasons Sotheby's Int'l Realty

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5107650

Redfin Estimate

$498,889

$1,111 since sold in October 2026$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.8% lower than the average sale price ($513K) of 6 comparable homes.

SOLD JUL 31, 2026
$860,000
A
4 beds2 baths1,848 sq ft
309 Ladyslipper Ln, Killington, VT 05751
SOLD OCT 16, 2026
$550,000
B
4 beds2.5 baths1,898 sq ft
106 Upper Loop, Ludlow, VT 05149
SOLD FEB 27, 2026
$550,500
C
3 beds2 baths1,728 sq ft
405 Soaring Hawk Rd, Plymouth, VT 05056
SOLD OCT 12, 2026
$339,000
D
3 beds2 baths1,694 sq ft
343 Dublin Rd, Plymouth, VT 05056
SOLD OCT 2, 2026
$330,000
E
3 beds2 baths1,645 sq ft
6 Irving Hts, Rutland, VT 05701
SOLD OCT 16, 2026
$450,000
F
3 beds3 baths1,786 sq ft
393 Tanglewood Dr, Killington, VT 05751

Claim this home to receive a free report every month with insights on the changing estimate.

Market trends in 05056, VT

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

91.8%

3.3% MoM

Median sale price

$575K

$18K MoM

Avg. days on market

141d

140 days MoM

Recently sold homes

1 MoM

Provided by Redfin

Homeowner tools

View owner dashboard

Track your estimate and nearby sale activity

Edit home facts

Review property details and add renovations

Manage photos

Update home photos or make them private

Rental estimate

Est. $2,682 per month, based on comparable rentals

Sale and tax history for 105 Upper Round Top Ext

Sale History
Tax History

Date

Event

Price

PrimeMLS #5107650

Oct 29, 2026

Sold

$500,000

$298/sq ft

Sep 7, 2026

Contingent

—

Sep 1, 2026

Listed

$499,000

$297/sq ft

PrimeMLS #4813029

Aug 25, 2020

Sold

$343,000

$204/sq ft

Jul 24, 2020

Contingent

—

Jun 24, 2020

Listed

$349,000

$208/sq ft

+33

MINUTES TO KILLINGTON, OKEMO OR WOODSTOCK! IMMEDIATE ACCESS TO SNOWMOBILING AND HIKING FROM YOUR DOOR! This totally renovated open concept 4 bedroom/ 2 bath contemporary chalet is being sold beautifully furnished and totally turn key! Move right in and begin to enjoy this fabulous home. The home offers a spacious floor plan perfect for entertaining. Walk in the home to a brand new mudroom with plenty of storage. Great kitchen that flows into an open dining and living area with wall of glass to enjoy the tranquil views. Living area has handsome stone hearth and gas fireplace. The lower level has an extra living/ hang out room for family and friends to stretch out. Large deck with huge hot tub. Relax by the firepit at night and soak in the stars and no light pollution! Sweet seasonal mountain views! Strong rental potential, excellent investment in the heart of ski and snowmobile country!

PrimeMLS #2804382

Jan 15, 2010

Sold

$215,000

$128/sq ft

Oct 16, 2009

Listed

$239,000

$142/sq ft

Slopside at Bear Creek Mtn Club, and minutes to Killington, Okemo and Woodstock!This wonderful chalet has loads of light and cathedral ceilings, a spacious open concept floor plan perfect for entertaining, a great room upstairs and lower rec room both with woodstoves, huge wraparound deck and more!Bring your snowmobiles, VAST trails are near by!Seasonal mountain views, beautiful tranquil setting. A great spot for primary or retreat home!Super location to enjoy all this area of Vt has to offer!

Year

Property tax

Land + Additions

Assessment*

2025

$4,578 (+13.0%)

$46,200 + $135,110

$181,310

2024

$4,051 (+23.7%)

$46,200 + $135,110

$181,310

2023

$3,274 (−18.3%)

$46,200 + $135,110

$181,310

2022

$4,006 (+7.3%)

$46,200 + $135,110

$181,310

2021

$3,735 (−5.0%)

$46,200 + $135,110

$181,310

2020

$3,933 (+0.3%)

$46,200 + $135,110

$181,310

2019

$3,923 (+2.3%)

$46,200 + $135,110

$181,310

2018

$3,835 (−1.6%)

$53,280 + $135,090

$188,370

2016

$3,896 (−1.3%)

$53,280 + $135,090

$188,370

2015

$3,948 (+5.1%)

$72,500 + $131,170

$203,670

2014

$3,758

$72,500 + $131,170

$203,670

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.44 Acres

Year renovated

—

Sq. Ft.

1,884

Year built

1975

Style

Single Family Residential

County

Windsor County

APN

48615310145

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 2, 2026.

Property details

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Walkout
Climate Controlled, Concrete, Concrete Floor, Finished

Other Interior Features
# of Rooms: 8
Flooring: Ceramic Tile, Laminate, Wood

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

Exterior

Building Information
Architectural Style: Chalet, Contemporary, Walkout Lower Level
Construction Status: Existing
Construction Materials: Stone Exterior, Wood Frame, Wood Siding
Approximate Sq. Ft. Total Finished: 1680
Approximate Sq. Ft. Total: 1680
Roof: Metal, Standing Seam

Driveway
Crushed Stone, Gravel

Lot, Zoning, & Easement Information
Lot Features: Country Setting, Mountain View, Recreational, Ski Area, Ski Trailside, Subdivision, Trail/Near Trail, View, Walking Trails, Wooded, Mountain, Near Country Club, Near Golf Course, Near Paths, Near Snowmobile Trails, Rural, Near ATV Trail

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1975

Financial

Tax Information
Tax Year: 2026
Gross Amount Tax: 5928.29
SPAN Number: 486-153-10145

Other Tax Information
Page Deed: 439

Utilities

Heating & Cooling Information
Cooling: Other
Heat: Propane, Electric, Stove - Gas

Sewer Information
Private, Septic

Electric Information
Electric Company: GMP
200 Amp, Circuit Breaker(s)

Water Information
Water Source: Community

Other Utilities Information
Internet: High Speed Intrnt -AtSite
Cable Company: VTEL or Xfinity
Fuel Company: CV Oil
Phone Company: VTEL
Cable - At Site, Telephone At Site

Location

Homeowners Association
Fee: 550
Yearly
Other, Plowing, Water

School Information
School District: Windsor Central
Elementary School: Choice
Elementary School: Choice
Middle/Jr School: Woodstock Union Middle Sch
School - High: Woodstock Senior UHSD #4

Road Information
Road Frontage Type: Association, Dirt, Gravel, Private Road, Privately Maintained
Road Frontage: TBD

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 1,884
Stories: 1.0
Lot Size: 0.44 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: Windsor County
APN: 48615310145

Home facts updated by county records on Sep 2, 2026

Other

Misc. Information
Resort: Yes

Documents & Disclosures
Documents Available: Deed, Property Disclosure

Listing Information
Sale Includes: Furnishings

Around this home

Schools

Killington Elementary School

Public PreK-6 • Assigned • 8.1mi

9/10

Provided by GreatSchools

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 87° expected this year, 16 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

Plymouth, VT • 05056

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

44/ 100

Low sunlight

Sunscore

There appears to be significant shading by surrounding buildings, terrain, and vegetation.

6 hrs

0.7 hr

JuneDecember

Provided by Shadowmap

Estimated sale price

$474,000 – $574,000

Sell confidently with a local market expert in Plymouth.

Nearby similar homes

FOR SALE BY OWNER

$875,000

4 beds3.5 baths2,983 sq ft

790 Chapman Rd, Ludlow, VT 05149

Wood burning stove • Open concept living • Deck access

3D WALKTHROUGH

$750,000

3 beds2 baths2,004 sq ft

1326 Curtis Hollow Rd, Woodstock, VT 05091

Eat-in kitchen • Exposed beams • Cozy wood stove

$1,750,000

2 beds3 baths2,848 sq ft

182 Bearly Hi Way, Killington, VT 05751

Unmatched views • Two decks • Covered porch

$292,000

3 beds1 bath1,344 sq ft

135 Harrington Ave, Rutland, VT 05701

Thoroughly renovated • Back porch • Flexible space

VIDEO TOUR

$4,500,000

20 beds20.5 baths15,684 sq ft

54 Red Clover Ln, Mendon, VT 05701

Mountain views • Historic charm • Landscaped drive

3D WALKTHROUGH

$1,099,000

3 beds2 baths1,248 sq ft

52 Fishing Access Rd, Ludlow, VT 05149

Sweeping water views • Private decks • 1.11 acre lot

Home values near 105 Upper Round Top Ext

Data from public records.

Address	Redfin Estimate
139 Upper Round Top Road, Plymouth, VT 3 Beds \| 1.5 Baths \| 1440 Sq. Ft.	$295,703
182 Upper Round Top Road #182, Plymouth, VT 3 Beds \| 2 Baths \| - Sq. Ft.	$260,617
209 Upper Round Top Road, Plymouth, VT 4 Beds \| 2 Baths \| 3186 Sq. Ft.	$524,137
116 Upper Round Top Road #C, Plymouth, VT 3 Beds \| 2 Baths \| 1264 Sq. Ft.	$434,896
116 Upper Round Top Road #H, Plymouth, VT 3 Beds \| 2 Baths \| 1264 Sq. Ft.	$434,896
167 Upper Round Top Road, Plymouth, VT 5 Beds \| 2 Baths \| 1740 Sq. Ft.	$492,051
116 Upper Round Top Road #A, Plymouth, VT 3 Beds \| 2 Baths \| 1180 Sq. Ft.	$285,152

Address	Redfin Estimate
182 Upper Round Top Road #F, Plymouth, VT 3 Beds \| 2 Baths \| 1280 Sq. Ft.	$262,754
155 Upper Round Top Road, Plymouth, VT 3 Beds \| 2 Baths \| 1528 Sq. Ft.	$384,244
116 Upper Round Top Road #G, Plymouth, VT 3 Beds \| 2 Baths \| 1264 Sq. Ft.	$434,896
102 Upper Round Top Road #102, Plymouth, VT 4 Beds \| 2 Baths \| 1479 Sq. Ft.	$247,385
79 Upper Round Top Road, Plymouth, VT 4 Beds \| 2 Baths \| 1539 Sq. Ft.	$385,750
182 Upper Round Top Road #D, Plymouth, VT - Beds \| - Baths \| - Sq. Ft.	$458,892
182 Upper Round Top Road, Plymouth, VT 4 Beds \| 2 Baths \| 1479 Sq. Ft.	$354,211

Address	Redfin Estimate
116 Upper Round Top Road #D, Plymouth, VT 4 Beds \| 2 Baths \| 1264 Sq. Ft.	$432,801
183 Upper Round Top Road, Plymouth, VT 4 Beds \| 3 Baths \| 2898 Sq. Ft.	$644,680
116 Upper Round Top Road #F, Plymouth, VT 3 Beds \| 2 Baths \| 1264 Sq. Ft.	$434,896
165 Upper Round Top Road, Plymouth, VT 2 Beds \| 1.5 Baths \| 1248 Sq. Ft.	$298,623
116 Upper Round Top Road #B, Plymouth, VT 3 Beds \| 2 Baths \| 1180 Sq. Ft.	$236,409
116 Upper Round Top Road, Plymouth, VT 3 Beds \| 2 Baths \| 1264 Sq. Ft.	$291,893
116 Upper Round Top Road #B-2, Plymouth, VT 3 Beds \| 2 Baths \| 1424 Sq. Ft.	$297,453

Property information provided by PrimeMLS when last listed in 2026. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Windsor County	Agents near me	South Burlington, VT homes for sale	Windsor County Housing Market
Houses for sale near me	Burlington, VT homes for sale	Brattleboro, VT homes for sale
Land for sale near me	Stowe, VT homes for sale	Waterbury, VT homes for sale
Open Houses near me	Woodstock, VT homes for sale	Windsor County Property Records
Condos for sale near me	Montpelier, VT homes for sale	VT New Listings

105 Upper Round Top Ext, Plymouth, VT 05056

Is this your home?

About this home

Redfin Estimate

Market trends in 05056, VT

Homeowner tools

Sale and tax history for 105 Upper Round Top Ext

Public record

Property details

Interior

Exterior

Financial

Utilities

Location

Public facts

Other

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 105 Upper Round Top Ext

More real estate resources

Lebanon homes for sale
Woodstock homes for sale
Hanover homes for sale

Grafton County homes for sale
Hillsborough County homes for sale
Merrimack County homes for sale