21 McGregor Dr, Sherborn, MA 01770
OFF MARKET

21 McGregor Dr
Sherborn, MA 01770

  • 5 Beds
  • 4 Baths
  • 4,300 sqft (on 5.88 acres)

$1,945,600

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $11,531/mo*
Refinance Your Home

$1,945,600

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $11,531/mo*
Refinance Your Home
5 Beds
4 Baths
4,300 sqft
(on 5.88 acres)

Local Information

  • Map ViewExplore the area around 21 McGregor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1970
Lot Size
5.88 acres
Living Area
4,300 sqft
Price/Sqft
$452
Parking
Garage

Description

Stunning Colonial on popular Sherborn ended way. Beautifully sited at the end of a long drive on five plus acres, in-ground pool and rambling stone walls abutting conservation land. This home boasts a granite and cherry kitchen, first floor library, five large bedrooms, four full baths and in-law suite with private entrance.
21 McGregor Dr, Sherborn, MA 01770 is a 5 bedroom, 4 bathroom, 4,300 sqft single-family home built in 1970. It last sold for $900,000 on Jun 19, 2009. It is currently off market. The Trulia Estimate is $1,945,600, with a rent estimate of $6,803/month.

Home Details for 21 McGregor Dr

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 5.88 acres

Price History for 21 McGregor Dr

DatePriceEventSource
06/19/2009$900,000Sold
N/A
07/24/2008$1,180,000ListingRemovedAgent Provided
03/17/2008$1,180,000PriceChange
Agent Provided
01/25/2008$1,235,000Listed For SaleAgent Provided
05/31/2000$715,000Sold
N/A
06/15/1995$590,000Sold
N/A

Market trends in Sherborn

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
1MoM
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Property Tax and Assessment

Year2025
Tax$25,275
Assessment$1,524,400
Home facts updated by county records

Comparable Sales for 21 McGregor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
15 Wildwood Dr, Sherborn, MA
0.61
Single-Family Home
$1,500,000
06/10/26
5
4
5,700
63 Oldfield Dr, Sherborn, MA
0.48
Single-Family Home
$1,475,000
08/06/25
4
2.5
2,630
88 Brush Hill Rd, Sherborn, MA
0.67
Single-Family Home
$850,000
11/04/25
4
2
2,096
18 Wildwood Dr, Sherborn, MA
0.74
Single-Family Home
$1,031,500
01/27/26
4
2.5
2,342
59 Prospect St, Sherborn, MA
0.74
Single-Family Home
$1,270,000
07/17/26
3
2.5
2,893
18 Old Orchard Rd, Sherborn, MA
1.07
Single-Family Home
$1,050,000
06/15/26
4
2.5
2,693
21 Western Ave, Sherborn, MA
0.76
Single-Family Home
$835,000
07/31/25
3
2.5
2,150
54 Prospect St, Sherborn, MA
0.86
Single-Family Home
$995,000
10/23/25
3
2
2,096
81 Brush Hill Rd, Sherborn, MA
0.55
Single-Family Home
$825,000
03/26/26
3
1.5
1,236
61 Old Orchard Rd, Sherborn, MA
1.23
Single-Family Home
$1,630,000
12/04/25
4
4
4,267

Nearby homes

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Assigned Schools

These are the assigned schools for 21 McGregor Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Sherborn

At least 26 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say there's wildlife

  • 83 % Say parking is easy

  • 82 % Say there's holiday spirit

  • 79 % Say people would walk alone at night

  • 66 % Say neighbors are friendly

  • 62 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say kids play outside

  • 55 % Say there are community events

  • 47 % Say there are sidewalks

  • 19 % Say streets are well-lit

  • 17 % Say it's walkable to restaurants

  • 14 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Rjh1760
    "Sherborn loves animals. Folks here keep an eye out for missing cats dogs goats and sheep v vi Next-door AP which is very popular "
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  • S. Frederick
    "Lived for a few years. Friendly community members, beautiful country walks available, and good schools. Enjoy commuting by commuter rail to Boston."
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  • Alex C.
    "A private suburban sanctuary in the woods, but still a short drive to a major shopping area and all the city of Boston has to offer."
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  • Laurel M.
    "The commute into the city is not great during rush hour. But the town is a great place to raise kids and I couldn’t think of a better place to grow up! "
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  • Sherborn3
    "I love the natural beauty and serenity of this town! Who can argue with top-notch schools combined with rural loveliness and the best pond in the state? Being a friendly small town, there is a strong sense of community. If you like McMansions everywhere with all the trees removed around them and ability to hear your neighbors' arguments, Sherborn is not for you. If you like green and you like privacy, it is for you! Very close to commuter rail and all that Natick has to offer without the negatives of that town."
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Apartments for Rent

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Homes for sale near 21 McGregor Dr

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Off Market Homes Near 21 McGregor Dr

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