39 Whitcomb Hill Road
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$699,900

39 Whitcomb Hill Road
Strafford, VT 05070
Listed by Kate Cassidy · Four Seasons Sotheby's Int'l Realty
Bedrooms
3
Bathrooms
2
Living area
N/A
Year built
1960

About this home

Set high above the rolling hills of South Strafford, this charming multi-level New Englander offers the perfect blend of privacy, character, and breathtaking Vermont beauty. Situated on 40.87 acres with sweeping mountain views, this three-bedroom, two-bath home invites you to slow down and embrace four-season living. A welcoming wraparound porch overlooks open meadows and mature trees, creating the ideal setting for morning coffee, evening sunsets, or gathering with friends after a day on the trails or slopes. Inside, warm wood floors, exposed beams, and abundant natural light create a cozy yet spacious atmosphere. The thoughtfully updated kitchen features custom cabinetry, open shelving, and a functional center island, while the inviting living room offers oversized windows framing the surrounding landscape. The home’s multi-level layout provides comfortable separation of space, including serene bedrooms with peaceful woodland views and flexible work-from-home potential. Outside, a classic barn adds versatility for storage, hobbies, animals, or future creative use. Located in a wonderful community close to skiing, hiking trails, and a highly regarded school system, this property is ideal for those seeking a Vermont mountain retreat with privacy, charm, and year-round recreation. Whether you are searching for a full-time residence, country getaway, or homestead lifestyle property, this special offering captures the essence of Vermont living.

Property details

MLS #
5091374
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
77
On market date
N/A
Stories
N/A
Garage spaces
N/A
Lot size
40.87 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Bernice A. Ray School
9.41 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
497
Student:teacher ratio
10.8:1
District
Hanover School District
Middle
Frances C. Richmond School
9.15 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
349
Student:teacher ratio
9.2:1
District
Dresden School District
High
None found nearby

Mortgage calculator

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Est. monthly payment
$4,365/mo
$139,980 down
$559,920 loan
Principal & interest$3,632
Property tax (est.)$583
Home insurance (est.)$150

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Copyright 2026 PrimeMLS. 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 08/04/26.