SOLD AUG 20, 2026

Listed by Heidi Zizza • Four Seasons Sotheby's Int'l Realty. Bought with Deerfield Valley Real Estate.

Sold on aug 2026

$369,000

•

2,168

sq ft

88 Happy Haven Rd, Wilmington, VT 05363

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About this home

Sweet Country Retreat Near Mount Snow & The Hermitage Club Tucked away on a quiet private road in the heart of Wilmington, this charming country home offers the perfect blend of privacy, comfort, and four-season Vermont living. Just minutes from Mount Snow and the exclusive Hermitage Club, this spacious property is an ideal mountain getaway, full-time residence, or investment opportunity. Featuring five generous bedrooms, 2 bathrooms, Vaulted open concept living and incredible sun filled interior! This home provides plenty of space for family and friends to gather after a day on the slopes, trails, or nearby lakes. A walk-out lower level includes a separate second unit, offering flexibility for guest accommodations, multigenerational living, rental income, or a private home office. Outside, the property truly shines. Stunning perennial gardens burst with color throughout the seasons, creating a picturesque setting that complements the natural beauty of Southern Vermont. Relax on the deck, enjoy the peaceful surroundings, and take in the serenity of this special location. Whether you're seeking a ski home, vacation retreat, or year-round residence, this inviting Wilmington property offers space, versatility, and classic Vermont charm in an unbeatable location near some of the region's most sought-after mountain amenities.

Single-familyProperty Type

1971Year Built

1.02 acresLot Size

$170Price/Sq.Ft.

Listed by Heidi Zizza • Four Seasons Sotheby's Int'l Realty

Bought with Gwynne Fitzgerald • Deerfield Valley Real Estate

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5095088

Redfin Estimate

$377,880

$8,880 since sold in August 2026$11K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.3% lower than the average sale price ($417K) of 6 comparable homes.

SOLD AUG 17, 2026
$349,000
A
6 beds2 baths1,920 sq ft
247 VT Route 100, Wilmington, VT 05363
SOLD JUN 5, 2026
$301,000
B
4 beds2 baths1,750 sq ft
91 Happy Haven Rd, Wilmington, VT 05363
SOLD AUG 7, 2026
$399,000
C
4 beds2 baths2,128 sq ft
44 Howes Loop, Wilmington, VT 05363
SOLD OCT 2, 2026
$465,000
D
3 beds2 baths2,070 sq ft
18 Quail Ct, Wilmington, VT 05363
SOLD SEP 24, 2026
$535,000
E
4 beds2 baths1,440 sq ft
67 Heritage Dr, Dover, VT 05356
SOLD JUN 3, 2026
$450,000
F
5 beds3.5 baths2,240 sq ft
47 Ives Rd, Wilmington, VT 05363

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Market trends in 05363, VT

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

99.0%

0.4% MoM

Median sale price

$397K

$13K MoM

Avg. days on market

78d

32 days MoM

Recently sold homes

1 MoM

New listings for sale

$699,000
3 beds3 baths2,340 sq ft
12 Three Streams Way Unit A-11, Wilmington, VT 05363
$539,000
3 beds2 baths1,655 sq ft
3 Valley Vw, Wilmington, VT 05363
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Sale and tax history for 88 Happy Haven Rd

Sale History
Tax History

Date

Event

Price

PrimeMLS #5095088

Aug 20, 2026

Sold

$369,000

$170/sq ft

Jul 19, 2026

Contingent

—

Jun 16, 2026

Listed

$389,900

$180/sq ft

PrimeMLS #4815363

Oct 26, 2020

Sold

$220,000

$101/sq ft

Aug 8, 2020

Contingent

—

Jul 29, 2020

Price Changed

$229,000

$106/sq ft

Jul 8, 2020

Listed

$239,000

$110/sq ft

+22

Sweet chalet on a country road. Interior features first floor great room, open concept kitchen, living and dining, 2 bedrooms, bath and a sleeping loft. Oak floors in the great room, large windows with natural light, vaulted ceilings with some exposed beams, windows overlooking the large back deck and beautifully landscaped yard w/ impeccably maintained vegetable and flower gardens. Wrap around side deck with plenty of room for entertaining. Walkout lower level 2 bedroom apartment, fully furnished and equipped for use as an Airbnb with an excellent rental history. Landscaped path to lower level deck and private entry. Close to the Village of Wilmington, Mount Snow and The Hermitage Club at Haystack Mountain offering both winter and summer activities.

PrimeMLS #3009915

Oct 15, 2001

Sold

$110,000

$51/sq ft

Aug 8, 2001

Listed

$114,000

$53/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$3,956 (−0.6%)

$40,000 + $253,360

$293,360

2024

$3,981 (+4.3%)

$40,000 + $253,360

$293,360

2023

$3,816 (−20.3%)

$25,000 + $190,000

$215,000

2022

$4,788 (+1.3%)

$25,000 + $190,000

$215,000

2021

$4,728 (−16.1%)

$25,000 + $190,000

$215,000

2020

$5,638 (+13.0%)

$25,000 + $190,000

$215,000

2019

$4,989 (+8.2%)

2018

$4,611 (+9.4%)

2017

$4,213 (+1.2%)

2016

$4,164 (−0.4%)

2015

$4,180 (+590.9%)

2014

$605

2013

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1.02 Acres

Year renovated

—

Sq. Ft.

2,168

Year built

1970

Style

Other

County

Windham County

APN

76224212883

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 23, 2026.

Property details

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 2

Basement Information
Basement: Yes
Basement Access: Walkout
Apartments, Exterior Access, Finished, Interior Access, Stairs - Interior, Walkout

Other Interior Features
# of Rooms: 8

Exterior

Building Information
Architectural Style: Chalet
Construction Status: Existing
Construction Materials: Wood Frame
Approximate Sq. Ft. Total Finished: 2168
Approximate Sq. Ft. Total: 2266
Color: Sage
Roof: Metal

Driveway
Dirt

Lot, Zoning, & Easement Information
Lot Features: Country Setting, Near Shopping, Near Skiing, Neighborhood, Near School(s), Private

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 1971

Financial

Tax Information
Tax Year: 2025
Gross Amount Tax: 5544.2
SPAN Number: 762-242-12883

Other Tax Information
Page Deed: 6-8

Utilities

Heating & Cooling Information
Heat: Oil

Sewer Information
Septic

Electric Information
Electric Company: GMP
100 Amp

Water Information
Water Source: On-Site Well Exists

Other Utilities Information
Internet: High Speed Intrnt -Avail
Fuel Company: Nido
Cable - Available

Location

Road Information
Road Frontage Type: Gravel, Private Road
Road Frontage: Yes
Road Frontage Length: 100

Other Location Information
Directions: Rte 100 to Happy Haven

Public facts

Beds: 5
Baths: 2.0
Sq. Ft.: 2,168
Stories: 2.0
Lot Size: 1.02 acres
Style: Other
Year Built: 1970
Year Renovated: —
County: Windham County
APN: 76224212883

Home facts updated by county records on Sep 23, 2026

Other

Documents & Disclosures
Documents Available: Other

Around this home

Schools

Deerfield Valley Elementary School

Public PreK-5 • Assigned • 0.3mi

8/10

Twin Valley Middle High School

Public 6-12 • Assigned • 7.1mi

3/10

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

8 days above 86° expected this year, 19 days in 30 years

4/10 Wind Factor

8% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Wilmington, VT • 05363

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

$359,000 – $435,000

Sell confidently with a local market expert in Wilmington.

Nearby similar homes

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New listings for sale in 05363

$699,000

3 beds3 baths2,340 sq ft

12 Three Streams Way Unit A-11, Wilmington, VT 05363

Finished basement • Gourmet kitchen • Gas fired wood stove

$539,000

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Renovated chalet • Large rear deck • Soaking tub

Home values near 88 Happy Haven Rd

Data from public records.

Address	Redfin Estimate
122 Happy Haven Road, Wilmington, VT 3 Beds \| 1 Baths \| 1008 Sq. Ft.	$250,196
75 Happy Haven Road, Wilmington, VT 4 Beds \| 2.5 Baths \| 2756 Sq. Ft.	$456,177

Address	Redfin Estimate
104 Happy Haven Road, Wilmington, VT 4 Beds \| 2 Baths \| 1938 Sq. Ft.	$405,247
59 Happy Haven Road, Wilmington, VT 3 Beds \| 2 Baths \| 2000 Sq. Ft.	$391,881

Address	Redfin Estimate
114 Happy Haven Road, Wilmington, VT 4 Beds \| 1.5 Baths \| 2330 Sq. Ft.	$428,185
99 Happy Haven Road, Wilmington, VT 6 Beds \| 3 Baths \| 2482 Sq. Ft.	$460,920

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

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GreatSchools Ratings provided by GreatSchools.org.

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88 Happy Haven Rd, Wilmington, VT 05363

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