Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers extra space to gather. A half bath is also located on the main level. Upstairs, the loft makes a great office, reading nook, or playroom. The lower level features a primary suite with a ¾ bath, two additional bedrooms, another ¾ bath, laundry, and a utility room. Step outside to the back deck and enjoy the countryside views, where you may even catch sight of cows grazing across the way. The North Adams Art Scene and Mass MoCA are just the start of what western Massachusetts and southern Vermont have to offer. Conveniently located near year-round recreation, including golfing, hiking, boating, biking, and snowmobiling, with skiing just minutes away at Mount Snow, Berkshire East, and Stratton. A warm and inviting move-in-ready property is ideal as a full-time residence or a Vermont getaway.
Active
Listed by:
Jennifer Densmore,
Deerfield Valley Real Estate 802-464-3055
Price cut: $20K (11/12)
$445,000
1587 Upper Holbrook Road, Whitingham, VT 05361
3beds
2,872sqft
Est.:
Single Family Residence
Built in 1989
3 Acres Lot
$438,500 Zestimate®
$155/sqft
$-- HOA
What's special
Cozy wood stoveDining areaBar areaCountryside viewsBeautiful acresPrimary suiteBack deck
- 88 days |
- 431 |
- 25 |
Zillow last checked: 8 hours ago
Listing updated: November 17, 2025 at 09:43am
Listed by:
Jennifer Densmore,
Deerfield Valley Real Estate 802-464-3055
Source: PrimeMLS,MLS#: 5061235
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- 3/4 bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Baseboard, Electric
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Refrigerator, Washer, Electric Stove
- Laundry: In Basement
Features
- Ceiling Fan(s), Dining Area, Kitchen/Dining, Primary BR w/ BA, Natural Light, Vaulted Ceiling(s)
- Flooring: Carpet, Wood, Vinyl Plank
- Windows: Blinds
- Basement: Finished,Full,Walkout,Interior Access,Interior Entry
- Fireplace features: Wood Stove Hook-up
Interior area
- Total structure area: 2,872
- Total interior livable area: 2,872 sqft
- Finished area above ground: 1,636
- Finished area below ground: 1,236
Property
Parking
- Parking features: Gravel
Features
- Levels: Two
- Stories: 2
- Exterior features: Deck
- Frontage length: Road frontage: 700
Lot
- Size: 3 Acres
- Features: Landscaped, Wooded
Details
- Parcel number: 75323910976
- Zoning description: residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Siding
- Foundation: Poured Concrete
- Roof: Metal
Condition
- New construction: No
- Year built: 1989
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Mound Septic, Septic Tank
- Utilities for property: Cable Available, Fiber Optic Internt Avail
Community & HOA
Location
- Region: Whitingham
Financial & listing details
- Price per square foot: $155/sqft
- Tax assessed value: $211,800
- Annual tax amount: $6,424
- Date on market: 9/13/2025
- Exclusions: some furnishings - list is forthcoming
- Road surface type: Gravel
Estimated market value
$438,500
$417,000 - $460,000
$4,179/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/12/2025 | Price change | $445,000-4.3%$155/sqft |
Source:  PrimeMLS #5061235 Report a problem | ||
| 9/13/2025 | Listed for sale | $465,000+3221.4%$162/sqft |
Source: PrimeMLS #5061235 Report a problem | ||
| 12/17/2001 | Sold | $14,000$5/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $211,800 |
| 2023 | -- | $211,800 |
| 2022 | -- | $211,800 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,575/mo
Principal & interest
$1726
Property taxes
$693
Home insurance
$156
Climate risks
Neighborhood: 05361
Nearby schools
GreatSchools rating
- 5/10Deerfield Valley Elementary SchoolGrades: PK-5Distance: 7.8 mi
- 5/10Twin Valley Middle High SchoolGrades: 6-12Distance: 0.8 mi
Schools provided by the listing agent
- Elementary: Deerfield Valley Elem. Sch
- Middle: Twin Valley Middle School
- High: Twin Valley High School
- District: Windham Southeast
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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