This stately home is perched upon its meticulously landscaped lot, offering an unparalleled private oasis, just steps from Wenakeening Woods and Holliston's Upper Charles Rail Trail. Refined interior spaces are brimming with natural light, an inviting open floor plan and thoughtful updates. The sunny kitchen features updated stainless appliances, granite countertops, hardwood flooring and sliding glass door, beautifully integrating the interior and exterior spaces. Inviting family room with gas fireplace; gracious living and dining rooms; powder room and mudroom complete the main level. Four generously sized bedrooms upstairs, showcased by the tranquil primary bedroom and its stunning bathroom with oversized tiled shower. Fabulous walk-up third floor offers many possibilities; finished lower level with bead board and recessed lighting, ideal for a playroom, office and exercise space. The magazine worthy backyard boasts a large deck with a pergola, patio and mature plantings.
Sold for $920,000
$920,000
1585 Highland St, Holliston, MA 01746
4beds
3,045sqft
Single Family Residence
Built in 1993
1.22 Acres Lot
$922,200 Zestimate®
$302/sqft
$4,252 Estimated rent
Home value
$922,200
$848,000 - $996,000
$4,252/mo
Zestimate® history
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$5,733/mo
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List your homeWhat's special
Gas fireplaceMeticulously landscaped lotSunny kitchenInviting family roomPrivate oasisGenerously sized bedroomsGranite countertops
Zillow last checked:
Listing updated:
Listed by:
Kathy Chisholm 508-479-0180,
Realty Executives Boston West 508-429-7391
Bought with:
Kevin Kilduff
Affinity REALTORS®
Source: MLS PIN,MLS#: 73371445
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s), Flooring - Wall to Wall Carpet, Dressing Room, Recessed Lighting
- Level: Second
Bedroom 2
- Features: Closet, Flooring - Wall to Wall Carpet
- Level: Second
Bedroom 3
- Features: Ceiling Fan(s), Closet, Flooring - Wall to Wall Carpet
- Level: Second
Bedroom 4
- Features: Ceiling Fan(s), Closet, Flooring - Wall to Wall Carpet
- Level: Second
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
- Level: First
Bathroom 2
- Features: Bathroom - Full, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
- Level: Second
Bathroom 3
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
- Level: Second
Dining room
- Features: Flooring - Hardwood
- Level: First
Family room
- Features: Flooring - Wood, Recessed Lighting
- Level: First
Kitchen
- Features: Flooring - Hardwood, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting, Slider, Stainless Steel Appliances
- Level: First
Living room
- Features: Flooring - Hardwood, Recessed Lighting
- Level: First
Heating
- Baseboard, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
- Laundry: Electric Dryer Hookup, Washer Hookup, Second Floor
Features
- Recessed Lighting, Beadboard, Game Room, Walk-up Attic
- Flooring: Wood, Tile, Carpet, Laminate, Hardwood
- Windows: Screens
- Basement: Full,Partially Finished,Radon Remediation System
- Number of fireplaces: 1
- Fireplace features: Family Room
Interior area
- Total structure area: 3,045
- Total interior livable area: 3,045 sqft
- Finished area above ground: 2,645
- Finished area below ground: 400
Property
Parking
- Total spaces: 6
- Parking features: Attached, Garage Door Opener, Paved Drive, Paved
- Attached garage spaces: 2
- Uncovered spaces: 4
Features
- Patio & porch: Deck - Wood, Patio
- Exterior features: Deck - Wood, Patio, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Screens
- Has view: Yes
- View description: Scenic View(s)
- Waterfront features: Lake/Pond, 1 to 2 Mile To Beach, Beach Ownership(Public)
Lot
- Size: 1.22 Acres
Details
- Parcel number: 522886
- Zoning: 101
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 1993
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Private Sewer
- Water: Public
- Utilities for property: for Electric Range, for Electric Dryer, Washer Hookup
Green energy
- Energy efficient items: Thermostat
Community & HOA
Community
- Features: Walk/Jog Trails, Golf, Bike Path, Conservation Area
HOA
- Has HOA: No
Location
- Region: Holliston
Financial & listing details
- Price per square foot: $302/sqft
- Tax assessed value: $868,800
- Annual tax amount: $12,728
- Date on market: 12/30/2025
Price history
| Date | Event | Price |
|---|---|---|
| 7/24/2025 | Sold | $920,000-3.2%$302/sqft |
Source: MLS PIN #73371445 Report a problem | ||
| 5/20/2025 | Contingent | $950,000$312/sqft |
Source: MLS PIN #73371445 Report a problem | ||
| 5/7/2025 | Listed for sale | $950,000+68.1%$312/sqft |
Source: MLS PIN #73371445 Report a problem | ||
| 7/12/2004 | Sold | $565,000+121.7%$186/sqft |
Source: Public Record Report a problem | ||
| 8/27/1993 | Sold | $254,800$84/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $12,728 +1% | $868,800 +3.9% |
| 2024 | $12,598 +3.1% | $836,500 +5.5% |
| 2023 | $12,214 +4.5% | $793,100 +17.9% |
| 2022 | $11,688 -0.3% | $672,500 +2.4% |
| 2021 | $11,726 +6.1% | $656,900 +12.1% |
| 2020 | $11,048 +2% | $586,100 +1.9% |
| 2019 | $10,829 +0.9% | $575,100 |
| 2018 | $10,737 +0.1% | $575,100 -0.7% |
| 2017 | $10,727 +1.6% | $579,200 +3.1% |
| 2016 | $10,560 +1.6% | $562,000 +4.8% |
| 2015 | $10,395 +0.9% | $536,400 +3.5% |
| 2014 | $10,306 +2.3% | $518,400 -4.2% |
| 2013 | $10,079 +4.4% | $541,300 +2.7% |
| 2012 | $9,658 +2.1% | $527,200 |
| 2011 | $9,458 +2.3% | $527,200 -7% |
| 2010 | $9,245 +4.8% | $566,800 -0.6% |
| 2009 | $8,818 +5.3% | $570,400 -1.1% |
| 2008 | $8,377 +2.4% | $576,900 -5.9% |
| 2007 | $8,181 +1.5% | $612,800 +7.7% |
| 2006 | $8,060 +0.8% | $569,200 +3.5% |
| 2005 | $7,993 +2.6% | $550,100 +4.7% |
| 2004 | $7,793 +8.6% | $525,500 +18.5% |
| 2003 | $7,177 +16.4% | $443,300 +16.4% |
| 2001 | $6,165 -4.6% | $381,000 +6% |
| 2000 | $6,464 +17.6% | $359,500 +11.7% |
| 1998 | $5,496 | $321,800 |
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: 1.8 mi
Schools provided by the listing agent
- Elementary: Placent/Miller
- Middle: 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
$922,200
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Estimated market value
$922,200
- Massachusetts
- Middlesex County
- Holliston
- 01746
- 1585 Highland St
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