21 McGregor Dr
Sherborn, MA 01770
5 Beds
4 Baths
4,300 sqft (on 5.88 acres)
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
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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 21 McGregor Dr
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Interior Details BasementNumber of Rooms: 10 |
Heating & Cooling Heating: Other, GasAir ConditioningHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: AsphaltExterior: Wood |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1970 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 5.88 acres |
Price History for 21 McGregor Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 06/19/2009 | $900,000 | Sold | N/A |
| 07/24/2008 | $1,180,000 | ListingRemoved | Agent Provided |
| 03/17/2008 | $1,180,000 | PriceChange | Agent Provided |
| 01/25/2008 | $1,235,000 | Listed For Sale | Agent Provided |
| 05/31/2000 | $715,000 | Sold | N/A |
| 06/15/1995 | $590,000 | Sold | N/A |
Market trends in Sherborn
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
25
4MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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 |
|---|---|---|---|---|---|---|---|
0.61 | Single-Family Home | $1,500,000 | 06/10/26 | 5 | 4 | 5,700 | |
0.48 | Single-Family Home | $1,475,000 | 08/06/25 | 4 | 2.5 | 2,630 | |
0.67 | Single-Family Home | $850,000 | 11/04/25 | 4 | 2 | 2,096 | |
0.74 | Single-Family Home | $1,031,500 | 01/27/26 | 4 | 2.5 | 2,342 | |
1.07 | Single-Family Home | $1,050,000 | 06/15/26 | 4 | 2.5 | 2,693 | |
0.76 | Single-Family Home | $835,000 | 07/31/25 | 3 | 2.5 | 2,150 | |
0.86 | Single-Family Home | $995,000 | 10/23/25 | 3 | 2 | 2,096 | |
0.55 | Single-Family Home | $825,000 | 03/26/26 | 3 | 1.5 | 1,236 | |
1.23 | Single-Family Home | $1,630,000 | 12/04/25 | 4 | 4 | 4,267 | |
1.19 | Single-Family Home | $1,600,000 | 11/07/25 | 4 | 3.5 | 3,331 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETJeanette Reedy, Preservation Properties
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OFF MARKETMimi Henning, Barrett Sotheby's International Realty
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SOLDMAR 26, 2026Ralph M Harvey III, Listwithfreedom.com
OFF MARKETLaura Mastrobuono, Compass
SOLDJUN 10, 2026Laura Mastrobuono, Compass
OFF MARKETDavid J. Oliveri, Berkshire Hathaway HomeServices Commonwealth Real Estate
Assigned Schools
These are the assigned schools for 21 McGregor Dr.
- Pine Hill Elementary School
- PK-5
- Public
- 393 Students
8/10GreatSchools RatingParent Rating AverageI am really surprised by the negative reviews below. I can't help but wonder if the last one was written out of anger over the changing elementary school start times. While it is not true that the school does not have a second emergency access road (it does) and not true that children can't talk to each other at lunch (they can) I am most surprised by the categorization of the school leadership. I have never met a more phenomenal principal, and between my kids and multiple moves we have been at seven elementary schools. I have experienced nothing but warmth and a true dedication to educating all children inclusively.Parent Review5y ago - Dover-Sherborn Regional High School
- 9-12
- Public
- 613 Students
10/10GreatSchools RatingParent Rating AverageDover-Sherborn High School is exceptional in academics and has faculty that genuinely care about the students. And while the education is rigorous, the opportunity for the students to learn more about areas the are interested in is always available. I appreciate the hard work the administration did to keep the kids in school during the pandemic. And, as a parent of a child who learns differently, the school has helped her not feel out of place while ensuring she gets the most of her secondary school education. The school has a no tolerance policy on bullying. Very excited to see what the next chapter brings with a new district superintendent that came from Boston Latin.Parent Review4y ago - Dover-Sherborn Regional Middle School
- 6-8
- Public
- 459 Students
8/10GreatSchools RatingParent Rating AverageBoth my children are Dover-Sherborn Regional Middle School students. I loved their teachers. They made my kids feel very welcome and helped with their curriculum. My daughter is in advanced program in high school and all the foundation was from Dover-Sherborn Regional Middle School. Above all, the teachers are very much dedicated and put their time and effort for the children. They addressed all my concerns immediately. This is really a lovely school for the Dover-Sherborn community.Parent Review5y ago 
Check out schools near 21 McGregor Dr.
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.
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Homes for sale near 21 McGregor Dr
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OFF MARKET
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Off Market Homes Near 21 McGregor Dr
SOLDJUN 26, 2026Kandi Pitrus, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLDJUN 25, 2026Barber Real Estate Group, William Raveis R.E. & Home Services- SOLDJUN 23, 2026
SOLDJUN 18, 2026Peter DiRusso, Venture
SOLDJUN 18, 2026Kandi Pitrus, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLDJUN 18, 2026Jeannine Coburn, REMAX Executive Realty
SOLDJUN 16, 2026Jon Gordon, Gordon Real Estate
SOLDJUN 15, 2026Friedler / Marchant Living Group, Hammond Residential Real Estate
SOLDJUN 15, 2026The Atwood Scannell Team, Dover Country Properties Inc.
SOLDJUN 15, 2026Steve Leavey, Keller Williams Realty- See more homes for sale inSherborn
21 McGregor Dr, Sherborn, MA 01770 is a 5 bedroom, 4 bathroom, 4,300 sqft single-family home built in 1970. This property is not currently available for sale. 21 McGregor Dr was last sold on Jun 19, 2009 for $900,000. The current Trulia Estimate for 21 McGregor Dr is $1,915,000.