21 Winthrop Rd
Brookline, MA 02445
Aspinwall Hill
1 Bed
1 Bath
2,820 sqft
1 Bed
1 Bath
2,820 sqft
Local Information
© Google
-- mins to
Description
(RLNE3825171)
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 only
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 21 Winthrop Rd
|
|---|
Heating & Cooling Heating: Other, GasHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 9 |
Fireplace & Spa Fireplace |
|
|---|
Exterior Home Features Roof: AsphaltExterior: Brick |
Parking & Garage GarageParking: Garage Attached |
|
|---|
Year Built Year Built: 1940Year Updated: 1972 |
Property Type / Style Property Type: Multi FamilyArchitecture: Colonial |
|
|---|
Units in Building: 1 |
|
|---|
Lot Area: 8712 sqft |
Price History for 21 Winthrop Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 04/21/1992 | $427,000 | Sold | N/A |
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $26,166 |
| Assessment | $2,651,100 |
Home facts updated by county records
Comparable Sales for 21 Winthrop Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.05 | Multi-Family Home | $2,452,000 | 06/16/25 | 8 | 3 | 3,544 | |
0.12 | Multi-Family Home | $1,800,000 | 01/13/26 | 9 | 4 | 3,102 | |
0.35 | Multi-Family Home | $1,690,000 | 08/15/25 | 5 | 2 | 2,310 | |
0.29 | Multi-Family Home | $2,200,000 | 02/02/26 | 5 | 3 | 3,978 | |
0.33 | Multi-Family Home | $1,800,000 | 06/13/25 | 5 | 2 | 2,318 | |
0.41 | Multi-Family Home | $1,800,000 | 10/31/25 | 5 | 2 | 2,252 | |
0.41 | Multi-Family Home | $2,820,000 | 12/23/25 | 7 | 5 | 4,171 | |
0.56 | Multi-Family Home | $1,900,000 | 08/08/25 | 6 | 3.5 | 3,895 | |
0.41 | Multi-Family Home | $2,650,000 | 12/12/25 | 6 | 3.5 | 3,277 | |
0.79 | Multi-Family Home | $1,250,000 | 12/23/25 | 5 | 2 | 2,644 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETLiz Kincannon, Coldwell Banker Realty - Weston
OFF MARKETMark Ruane, MGS Group Real Estate LTD
OFF MARKETAlina Wang Team, Coldwell Banker Realty - Lexington
OFF MARKETCote Partners Realty LLC
OFF MARKETMona And Shari Wiener, Hammond Residential Real Estate
OFF MARKETLiz Dehler, Donnelly + Co.
OFF MARKETJamie Genser, Coldwell Banker Realty - Brookline
OFF MARKETMary Crane, Berkshire Hathaway HomeServices Commonwealth Real Estate
OFF MARKETKate Brasco, Century 21 Shawmut Properties
OFF MARKETThe Bushari Team Compass, Compass
Assigned Schools
These are the assigned schools for 21 Winthrop Rd.
- Brookline High School
- 9-12
- Public
- 2147 Students
8/10GreatSchools RatingParent Rating AverageWe moved to Brookline, in part because of the excellent school system, and have not been disappointed.Our oldest is now a freshman in college at one of the world's best schools and our youngest is thriving here.Parent Review4y ago - Pierce School
- K-8
- Public
- 587 Students
9/10GreatSchools RatingParent Rating AverageMy autistic son went without water for lunch and until 1 pm with 0 help from the teachers, it took me writing an email and even then principal had 0 answers for why he wasn’t able to get water until 1 pm. Gym teacher singled out my son after a kid threw a ball at him twice, my son threw it back and gym teacher only took him out and told my son the group was better off without him and the other student who sat out from the start of the class due to throwing the ball backwards. Principal lies about policies, I wanted to record the meeting about my son and the incident that happened she emailed me saying it’s student privacy policy, then she emailed me again saying page 401 appendix C which has nothing to do with prohibiting recording meetings about your child with principal and only has to do with suspension. My son had Pokémon cards stolen from him the start of the year, because he was new and didn’t know kids names nothing could be done, undercooked pasta/food. IEP staff doesn’t follow actual medical diagnosis and won’t do anything to help your kid if they have a learning disability/mental disability. Better off homeschoolingParent Review1y ago 
Check out schools near 21 Winthrop Rd.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Aspinwall Hill
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
NEW - 1 DAY AGOPET FRIENDLY$2,535 - $10,805/moFees may apply1-3 bd1-3 baHancock Village | 1 Hancock Village Dr #F-606,
Chestnut Hill, MA 02467
PET FRIENDLY
NEW - 1 DAY AGOPET FRIENDLY$3,195 - $6,585/moFees may apply1-2 bd1-3 baThe Franklin at Hancock Village | 201 Sherman Rd #F-606,
Chestnut Hill, MA 02467
PET FRIENDLY$3,845 - $6,327/moFees may applyStudio-2 bd1-2 baThe Harlo | 1350 Boylston St #Penthouse 1612,
Boston, MA 02215
PET FRIENDLYTotal price$3,053 - $6,254/moStudio-2 bd1-2 baProto Kendall Square | 88 Ames St #513,
Cambridge, MA 02142
PET FRIENDLYTotal price$3,051 - $4,677/mo1-2 bd1-2 baGables Arsenal Street | 204 Arsenal St #405,
Watertown, MA 02472
PET FRIENDLY$3,135 - $5,995/moFees may apply1-3 bd1-3 baThe Adams at Hancock Village | 101 Asheville Rd #A-503,
Chestnut Hill, MA 02467
NEW - 1 DAY AGO
PET FRIENDLY
NEW - 40 MIN AGOINCOME RESTRICTEDTotal price$3,695 - $5,195/mo2-3 bd1-2 baMission Main | 43 Smith St #H002B,
Roxbury Crossing, MA 02120
PET FRIENDLYTotal price$3,118 - $4,188/mo1-2 bd1 baThe Longwood | 1575 Tremont St #704,
Roxbury Crossing, MA 02120
PET FRIENDLYTotal price$3,311 - $4,061/moStudio-1 bd1 baAlder at Allston Yards | 301 Guest St #524,
Brighton, MA 02135
PET FRIENDLYTotal price$2,749 - $4,435/moStudio-2 bd1-2 baThe Charley | 46 Soldiers Field Pl #44-512,
Brighton, MA 02135
PET FRIENDLY
PET FRIENDLYTotal price$2,890 - $3,271/moStudio-1 bd1 baForte at 1440 Beacon | 1440 Beacon St #109,
Brookline, MA 02446
See more homes for rent inBrookline
Explore by feature
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY$3,195 - $6,585/moFees may apply1-2 bd1-3 baThe Franklin at Hancock Village | 201 Sherman Rd #F-606,
Chestnut Hill, MA 02467 - SPECIAL OFFERPET FRIENDLY$3,135 - $5,995/moFees may apply1-3 bd1-3 baThe Adams at Hancock Village | 101 Asheville Rd #A-503,
Chestnut Hill, MA 02467 - SPECIAL OFFERPET FRIENDLYTotal price$2,890 - $3,271/moStudio-1 bd1 baForte at 1440 Beacon | 1440 Beacon St #109,
Brookline, MA 02446 - NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY$2,535 - $10,805/moFees may apply1-3 bd1-3 baHancock Village | 1 Hancock Village Dr #F-606,
Chestnut Hill, MA 02467 
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLYTotal price$3,300 - $6,250/mo1-4 bd1-3 baVillage At Brookline | 77 Village Way #703,
Brookline, MA 02445
SPECIAL OFFERPET FRIENDLYTotal price$2,561 - $4,743/moStudio-2 bd1-2 baPelham Hall | 1284 Beacon St #205,
Brookline, MA 02446
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY$3,975 - $4,995/moFees may apply2-3 bd1 baLongwood Ave Apartments | 98 Longwood Ave #3,
Brookline, MA 02446
Homes for sale near 21 Winthrop Rd
OFF MARKET
Jonmarc Mallory, R. Conte Construction, Inc.
OPEN SUN, 11:30-1PM0.41 ACRESScott Goldsmith, Gibson Sotheby's International Realty
OFF MARKET
Tayler Barbella, Boston Realty Advisors
OPEN SUN, 12-1PMMary Lochner, Coldwell Banker Realty - Brookline
NEWOPEN SUN, 12-2PMMatt Gorman, EDGE Realty Advisors
See more homes for sale inBrookline
Off Market Homes Near 21 Winthrop Rd
SOLDMAY 29, 2026Max Dublin Team, Gibson Sotheby's International Realty
SOLDMAY 29, 2026Cheryl Cotney, Compass
SOLDMAY 29, 2026Christine Norcross & Partners, William Raveis R.E. & Home Services
SOLDMAY 29, 2026Rob Ramsdell, Gibson Sotheby's International Realty
SOLDMAY 29, 2026Brian McTigue, Coldwell Banker Realty - Newton
SOLDMAY 29, 2026Paul Whaley/Charlie Ring Team, Coldwell Banker Realty - Boston
SOLDMAY 29, 2026Caroline Gould, Corcoran Property Advisors
SOLDMAY 29, 2026The Dwyer and Davis Team, The Collaborative Companies
SOLDMAY 29, 2026Laura Segal, Gibson Sotheby's International Realty
SOLDMAY 29, 2026Manuel Davis, The Collaborative Companies- See more homes for sale inBrookline
Homes for rent near 21 Winthrop Rd
- NEW - 1 DAY AGOPET FRIENDLY$2,535 - $10,805/moFees may apply1-3 bd1-3 baHancock Village | 1 Hancock Village Dr #F-606,
Chestnut Hill, MA 02467 
APPLY INSTANTLY
APPLY INSTANTLY
APPLY INSTANTLY
APPLY INSTANTLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLYPET FRIENDLY- See more homes for rent inBrookline
21 Winthrop Rd, Brookline, MA 02445 is a 1 bedroom, 1 bathroom, 2,820 sqft multi-family built in 1940. 21 Winthrop Rd is located in Aspinwall Hill, Brookline. This property is not currently available for sale. 21 Winthrop Rd was last sold on Apr 21, 1992 for $427,000. The current Trulia Estimate for 21 Winthrop Rd is $2,810,500.