Set on a bucolic 10-home private drive, bordered by peaceful conservation land, this one-of-a-kind Southern Cape-style home on 3.7 acres blends timeless charm with refined comfort. From the inviting front porch, step into the exquisite two-story foyer with its custom open staircase. A wall of French door sliders fills the open-concept kitchen and family room w/incredible sunlight, creating comfort for everyday living. The updated kitchen shines w/quartz counters, tile backsplash, & wet bar, perfect for entertaining. The first floor also includes an elegant dining room, office, & inviting primary suite with walk-in closet, vaulted ceiling & plantation shutters. Upstairs are three spacious bedrooms with dormered windows & window seats, plus a versatile loft. The finished lower level features a gym, bonus room, & additional office. Rarely does a home with this character, privacy, and setting come to market! New roof 2023, new HVAC 2024, exterior painted 2024, interior painted 2025 & more!
Sold for $1,195,000
$1,195,000
257 Underwood St, Holliston, MA 01746
4beds
3,977sqft
Single Family Residence
Built in 1996
3.78 Acres Lot
$1,199,800 Zestimate®
$300/sqft
$4,462 Estimated rent
Home value
$1,199,800
$1.10M - $1.30M
$4,462/mo
Zestimate® history
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$4,462/mo
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$8,449/mo
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List your homeWhat's special
Versatile loftAdditional officeVaulted ceilingUpdated kitchenFinished lower levelPrivate driveCustom open staircase
Zillow last checked:
Listing updated:
Listed by:
Diane Regan 508-509-8626,
Berkshire Hathaway HomeServices Robert Paul Properties 617-262-1414
Bought with:
The Walsh Team & Partners
William Raveis R.E. & Home Services
Source: MLS PIN,MLS#: 73393857
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Vaulted Ceiling(s), Walk-In Closet(s), Closet, Flooring - Wall to Wall Carpet
- Level: First
Bedroom 2
- Features: Closet, Flooring - Wall to Wall Carpet, Decorative Molding
- Level: Second
Bedroom 3
- Features: Walk-In Closet(s), Flooring - Wall to Wall Carpet, Decorative Molding, Window Seat
- Level: Second
Bedroom 4
- Features: Closet, Flooring - Wall to Wall Carpet, Beadboard
- Level: Second
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Flooring - Hardwood, Crown Molding, Pedestal Sink
- Level: First
Bathroom 2
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Shower Stall, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub, Recessed Lighting, Lighting - Sconce, Lighting - Overhead
- Level: First
Bathroom 3
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Hardwood, Countertops - Stone/Granite/Solid
- Level: Second
Dining room
- Features: Flooring - Hardwood, Wainscoting, Decorative Molding, Tray Ceiling(s)
- Level: First
Family room
- Features: Cathedral Ceiling(s), Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Recessed Lighting, Slider
- Level: Main,First
Kitchen
- Features: Flooring - Hardwood, Window(s) - Bay/Bow/Box, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Wet Bar, Open Floorplan, Recessed Lighting, Crown Molding
- Level: First
Living room
- Features: Flooring - Hardwood, Crown Molding
- Level: First
Heating
- Central, Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Water Treatment, Plumbed For Ice Maker
- Laundry: Flooring - Stone/Ceramic Tile, Electric Dryer Hookup, Washer Hookup, First Floor
Features
- Recessed Lighting, Decorative Molding, Window Seat, Loft, Bonus Room, Wet Bar
- Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet
- Doors: Insulated Doors, French Doors
- Windows: Insulated Windows, Screens
- Basement: Full,Finished,Interior Entry,Bulkhead,Radon Remediation System,Concrete
- Number of fireplaces: 1
- Fireplace features: Family Room
Interior area
- Total structure area: 3,977
- Total interior livable area: 3,977 sqft
- Finished area above ground: 3,014
- Finished area below ground: 963
Property
Parking
- Total spaces: 6
- Parking features: Attached, Paved Drive, Off Street
- Attached garage spaces: 2
- Uncovered spaces: 4
Features
- Patio & porch: Porch, Deck
- Exterior features: Porch, Deck, Rain Gutters, Sprinkler System, Screens, Stone Wall
- Waterfront features: Lake/Pond, 1 to 2 Mile To Beach, Beach Ownership(Public)
Lot
- Size: 3.78 Acres
- Features: Cleared
Details
- Parcel number: 524432
- Zoning: 101
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 1996
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Private Sewer
- Water: Private
- Utilities for property: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
Community & HOA
Community
- Features: Shopping, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Bike Path, Conservation Area, House of Worship, Public School
- Subdivision: Miller Hill
HOA
- Has HOA: Yes
- HOA fee: $950 annually
Location
- Region: Holliston
Financial & listing details
- Price per square foot: $300/sqft
- Tax assessed value: $894,000
- Annual tax amount: $13,097
- Date on market: 1/11/2026
- Listing terms: Seller W/Participate
Price history
| Date | Event | Price |
|---|---|---|
| 8/1/2025 | Sold | $1,195,000$300/sqft |
Source: MLS PIN #73393857 Report a problem | ||
| 6/26/2025 | Contingent | $1,195,000$300/sqft |
Source: MLS PIN #73393857 Report a problem | ||
| 6/19/2025 | Listed for sale | $1,195,000+225.6%$300/sqft |
Source: MLS PIN #73393857 Report a problem | ||
| 7/26/1996 | Sold | $367,000$92/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $13,097 +1% | $894,000 +3.8% |
| 2024 | $12,973 +3.1% | $861,400 +5.5% |
| 2023 | $12,579 +0.7% | $816,800 +13.6% |
| 2022 | $12,493 -7.3% | $718,800 -4.8% |
| 2021 | $13,475 +7.4% | $754,900 +13.4% |
| 2020 | $12,547 +2.6% | $665,600 +2.5% |
| 2019 | $12,228 +0.9% | $649,400 |
| 2018 | $12,124 -2.7% | $649,400 -3.5% |
| 2017 | $12,464 +1.2% | $673,000 +2.6% |
| 2016 | $12,322 +10% | $655,800 +13.5% |
| 2015 | $11,200 -2.2% | $577,900 +0.3% |
| 2014 | $11,453 +2.1% | $576,100 -4.3% |
| 2013 | $11,215 +7.4% | $602,300 +5.7% |
| 2012 | $10,439 +2.1% | $569,800 |
| 2011 | $10,222 +2.3% | $569,800 -7% |
| 2010 | $9,990 +8.6% | $612,500 +2.9% |
| 2009 | $9,202 +0.3% | $595,200 -5.8% |
| 2008 | $9,172 +2.3% | $631,700 -6% |
| 2007 | $8,967 +4.9% | $671,700 +11.3% |
| 2006 | $8,548 -2.6% | $603,700 |
| 2005 | $8,772 +3.1% | $603,700 +5.2% |
| 2004 | $8,508 +3.3% | $573,700 +12.8% |
| 2003 | $8,236 +15.4% | $508,700 +15.4% |
| 2001 | $7,135 +18.8% | $441,000 +25.4% |
| 1998 | $6,005 | $351,600 |
Find assessor info on the county website
Neighborhood: 01746
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Nearby schools
GreatSchools rating
- NAPlacentino Elementary SchoolGrades: PK-2Distance: 1.9 mi
- 8/10Robert H. Adams Middle SchoolGrades: 6-8Distance: 1.7 mi
- 9/10Holliston High SchoolGrades: 9-12Distance: 1 mi
Schools provided by the listing agent
- Elementary: Placentino
- Middle: Robert Adams
- High: Holliston High
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,199,800
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Estimated market value
$1,199,800
- Massachusetts
- Middlesex County
- Holliston
- 01746
- 257 Underwood St
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