5 Roundtree Road

Closed 5/15/18

Closed

Last Sold Price

$329,000

4 beds4 baths1,710 sqft

5 Roundtree Rd, Winhall, VT 05340

Single FamilyProperty Type

1.05 acresLot Size

1965Year Built

$192/sq ftPrice per sq ft

$100/moHOA Fees

Description

This appealing Alpine vacation home will surprise you with its adaptability to different lifestyles. As a delightful and bright 4 bedroom, 3 1/2 bath single family residence, it offers a main level with cathedral ceiling Great Room, updated kitchen with breakfast bar, expansive deck onto a secluded sun dappled backyard, and 2 bedrooms en suite. The entry level has an air lock mudroom, renovated family room, full bath, convenient galley kitchen for overflow entertainment and 2 guest bedrooms one with...This appealing Alpine vacation home will surprise you with its adaptability to different lifestyles. As a delightful and bright 4 bedroom, 3 1/2 bath single family residence, it offers a main level with cathedral ceiling Great Room, updated kitchen with breakfast bar, expansive deck onto a secluded sun dappled backyard, and 2 bedrooms en suite. The entry level has an air lock mudroom, renovated family room, full bath, convenient galley kitchen for overflow entertainment and 2 guest bedrooms one with half bath. The entry level can also be an inlaw or one of the few rental apartments in the resort with a lock out interior stairway linking the two levels. Enjoy all the spaces as family and friends mingle and mix. Or define your privacy. This charming chalet will serve you well as times and needs change. Located on a short cul de sac in sought after North Brookwood neighbor home with shuttle bus service & Sports Club bond included this special property is offered furnished.

Sold By Four Seasons Sotheby's Int'l Realty

Listing closed: 05/15/2018 12:00 AM • Source: New England Real Estate Network, MLS#: 4507323

Recent comparable sales

Median sold price

$849,000

Avg days on market

118

Sale-to-list ratio

94.8%

1/46

$849,000

Sold 12/04/25

4
Bedrooms: 4
Bathrooms: 2,028
Square Feet: 0.89
Acres

7 North Brookwood Road, Winhall, VT 05340

1/33

$950,000

Sold 12/06/24

4
Bedrooms: 4
Bathrooms: 3,658
Square Feet: 1
Acres

154 High Meadow Road, Unit C17, Winhall, VT 05340

1/37

$960,000

Sold 05/22/26

4
Bedrooms: 4
Bathrooms: 2,280
Square Feet: 1.42
Acres

17 Roundtree Road, Winhall, VT 05340

1/47

$1,270,000

Sold 03/20/26

4
Bedrooms: 4
Bathrooms: 4,640
Square Feet: 20.8
Acres

33 Forest Haunts Road, Winhall, VT 05343

1/27

$795,000

Sold 08/21/25

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Bedrooms: 3
Bathrooms: 1,624
Square Feet: 0.97
Acres

5 Founders Hill Road, Winhall, VT 05340

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Sold 10/28/25

4
Bedrooms: 2
Bathrooms: 1,908
Square Feet: 1.16
Acres

6 Roundtree Road, Winhall, VT 05340

1/39

$725,000

Sold 10/02/26

4
Bedrooms: 4
Bathrooms: 3,520
Square Feet: 2.39
Acres

12 Stratton Ridge Road, Winhall, VT 05340

1/61

$817,500

Sold 12/13/24

4
Bedrooms: 4
Bathrooms: 3,772
Square Feet: 2.95
Acres

53 Stratton View Road, Winhall, VT 05340

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$1,700,000

Sold 11/22/24

4
Bedrooms: 4
Bathrooms: 4,777
Square Feet: 1
Acres

4 Stone House Road, Winhall, VT 05340

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Principal and Interest

$1,756

Property Taxes

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Property Information for 5 Roundtree Road

Property Details

Taxes: $6,967 / year
MLS Type: Residential / Single Family
County: Bennington County
Development / Subdivision: Stratton Resort
Parking: None
Zoning: REC

Building Information

Stories: 2
Year Built: 1965
Lot Size: 1.05 AC / 45,738 SF

Summary

Location and General Information

Area Description: Mountain, Near Public Transportatn
City: Winhall

County: VT-Bennington
Directions: From Bondville Route 30 take Mountain Road, right onto North Brookwood, 2nd road on right. 2nd driveway on left.
Latitude: 43.11696254659
Longitude: -72.914109089761
Road Frontage: Yes
Seasonal: No
State: VT
Street Designation: Road
Zip: 05340

Taxes and HOA Information

Fee: $100.00
Fee Frequency: Monthly

SPAN Number: 771-245-11077
Tax - Gross Amount: $6,966.68
Tax Year: 2015
Taxes TBD: No

School Information

School - High: Choice
School - District: Winhall School District

School - Elementary: Choice
School - Middle/Jr: Choice

Parking

Garage: No
Garage Capacity: .00

Driveway: Gravel

Property

Lot Information

Lot - Sqft: 45738.0
Lot Size Acres: 1.05

Road Frontage Length: 110.0
Square Feet Apx Finished Above Grade: 900.0
Square Feet Apx Finished AG Source: Public Records
Square Feet Apx Finished Below Grade: 810.0
Square Feet Apx Finished BG Source: Public Records
Square Feet Apx Tot BG Source: Public Records
Square Feet Apx Total: 1710.0
Square Feet Apx Tot Below Grade: 810.0
Square Feet Apx Total Finished: 1710.0
Square Feet Apx Unfinished Above Grade: 0.0
Square Feet Apx Unfinished Below Grade: 0.0

Property and Assessments

Current Use: No
Property Class: Residential

Property Type: Single Family
Flood Zone: No
Foundation: Slab w/ Frost Wall
Resort: Yes
Surveyed: Yes
Year Built: 1965

Utilities

Electric Company: Green Mountain Power
Cable Company: Comcast

Electric: Circuit Breaker(s)
Sewer: Community
Utilities: Cable

Interior and Exterior Features

Exterior Features

Features - Accessibility: 1st Floor 1/2 Bathroom, 1st Floor Bedroom, 1st Floor Full Bathroom
Features - Exterior: Deck

Roads: Association, Cul-de-Sac, Gravel
Roof: Standing Seam

Interior Features

Appliances: Dishwasher, Disposal, Dryer, Exhaust Hood, Microwave, Range - Electric, Refrigerator, Washer
Basement: No

Basement Description: None
Baths - Total: 4
Baths - Full: 3
Half Baths: 1
One Quarter Baths: 0
Three Quarter Bath: 0
Rooms - Total: 8
Rooms: Level 1: Level 1: Bedroom, Level 1: Bath - Full, Level 1: Bath - 1/2, Level 1: Family Room, Level 1: Mudroom, Level 1: Other
Rooms: Level 2: Level 2: Bedroom, Level 2: Bath - Full, Level 2: Dining Room, Level 2: Kitchen, Level 2: Living Room, Level 2: Master Bedroom
Bedrooms - Total: 4
Equipment: Smoke Detector, Smoke Detectr-Hard Wired
Features - Interior: Cathedral Ceiling, Fireplace - Wood, Fireplaces - 1, Furnished, In-Law/Accessory Dwelling, Living/Dining, Master BR w/ BA, Natural Woodwork, Security Door(s), Skylight, Laundry - 1st Floor
Flooring: Softwood, Tile, Vinyl
Heat Fuel: Electric
Heating: Baseboard, Multi Zone
Cooling: Multi Zone
Total Stories: 2

Room Information

Room 1

Room Dimensions: 8.6 x 9
Room Level: 2

Room Type: Kitchen

Room 2

Room Dimensions: 12 x 9
Room Level: 2

Room Type: Dining Room

Room 3

Room Dimensions: 16 x 12.6
Room Level: 2

Room Type: Living Room

Room 4

Room Dimensions: 13 x 17
Room Level: 1

Room Type: Family Room

Room 5

Room Level: 1
Room Type: Mudroom

Room 7

Room Dimensions: 10.6 x 11.6
Room Level: 2

Room Type: Master Bedroom

Room 8

Room Dimensions: 12 x 11
Room Level: 2

Room Type: Bedroom

Room 9

Room Dimensions: 9 x 10
Room Level: 1

Room Type: Bedroom

Room 10

Room Dimensions: 9 x 10
Room Level: 1

Room Type: Bedroom

Room 13

Room Dimensions: 5 x 11
Room Level: 1

Room Type: Other

Room 14

Room Dimensions: 6 x 6
Room Level: 1

Room Type: Other

Room 16

Room Level: 1
Room Type: Bath - Full

Room 17

Room Level: 2
Room Type: Bath - Full

Room 18

Room Level: 2
Room Type: Bath - Full

Room 19

Room Level: 1
Room Type: Bath - 1/2

Property History for 5 Roundtree Road

Date	Event & Source	Price	Appreciation
May 15, 2018	Sold (Public Record) Public Record #624177762	$329,000	—
May 15, 2018	Sold New England Real Estate Network #4507323	$329,000	—
Mar 25, 2018	Pending New England Real Estate Network #4507323	—	—
Jul 28, 2016	Price Change New England Real Estate Network #4507323	$385,000	—
Jul 28, 2016	Listed (Active) New England Real Estate Network #4507323	$335,000	—

Date	Event & Source	Price
05/15/2018	Sold (Public Record) Public Record #624177762	$329,000
05/15/2018	Sold New England Real Estate Network #4507323	$329,000
03/25/2018	Pending New England Real Estate Network #4507323	—
07/28/2016	Price Change New England Real Estate Network #4507323	$385,000
07/28/2016	Listed (Active) New England Real Estate Network #4507323	$335,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 5 Roundtree Road

Taxable Value

Land

$163,600

Additions

$185,800

Total$349,400

Tax Record

2025

$7,306 ($609 / month)

Home Facts

Beds

Baths

Total Finished SqFt

900 SqFt

Above Grade Finished SqFt

900 SqFt

Unfinished Basement SqFt

810 SqFt

Lot Size

47,480 SqFt

Style

Single Family Residence

Year Built

1966

Year Renovated

1966

County

BENNINGTON

APN

(245)01250

Schools near 5 Roundtree Road


Rating	School	Type	Grades	Distance
NR	Stratton Mountain School	Private - Nearby school	6 to 12	1.6 mi
NR	Mountain School At Winhall	Private - Nearby school	K to 8	2.4 mi


Rating	School	Distance
NR	Stratton Mountain School Private6 to 12 Nearby school	1.6 mi
NR	Mountain School At Winhall PrivateK to 8 Nearby school	2.4 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 5 Roundtree Road, Winhall, VT 05340	$329,000	4	4	1,710	45,738
19 Roundtree Road, Winhall, VT 05340	$1,000,000	4	3	3,086	63,162
20 North Brookwood Road, Bondville, VT 05340	$569,000	4	4	2,312	56,628
77 Roundtree Road, Winhall, VT 05340	$150,900	–	–	–	43,560
79 Roundtree Road, Winhall, VT 05340	$615,000	4	1	3,200	43,560
16 Roundtree Road, Bondville, VT 05340	–	4	2.5	1,383	46,609
13 Roundtree Road, Winhall, VT 05340	$495,000	4	3	3,022	62,290
6 Roundtree Road, Winhall, VT 05340	$815,000	4	2	1,908	50,529
16 North Brookwood Road, Winhall, VT 05340	$569,000	8	6	4,600	56,628
14 Roundtree Road, Bondville, VT 05340	–	4	3	2,646	43,996
10 Roundtree Road, Winhall, VT 05340	$888,000	4	4	3,026	44,866
24 North Brookwood Road, Bondville, VT 05340	–	3	3	2,087	64,904
96 Roundtree Road, Winhall, VT 05340	$550,000	4	4	2,600	43,995
10 Windtree Road, Bondville, VT 05340	–	5	3	2,625	65,340
8 Windtree Road, Bondville, VT 05340	–	1	1.5	1,318	65,340
2 Roundtree Road, Bondville, VT 05340	$585,000	5	5	2,492	56,628

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Listing Courtesy of Four Seasons Sotheby's Int'l Realty

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 11/08/2026 10:52 AM

5 Roundtree Rd, Winhall, VT 05340

Winhall, VT

Property Details

Building Information

Summary

Property

Interior and Exterior Features

Room Information

Taxable Value

Land

Additions

Tax Record

2025

Home Facts

Beds

Baths

Total Finished SqFt

Above Grade Finished SqFt

Unfinished Basement SqFt

Lot Size

Style

Year Built

Year Renovated

County

APN

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