33 Winthrop Rd #2, Brookline, MA 02445
Property image
Property image
OFF MARKET

33 Winthrop Rd #2
Brookline, MA 02445

Aspinwall Hill
  • 6 Beds
  • 4.5 Baths
  • 4,900 sqft

$3,594,500

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $21,023/mo*
Refinance Your Home

$3,594,500

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $21,023/mo*
Refinance Your Home
6 Beds
4.5 Baths
4,900 sqft

Local Information

  • Map ViewExplore the area around 33 Winthrop Rd #2.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Nestled at the end of a private way, this two year old spacious contemporary home provides urban living in a secluded suburban setting. The stately home flooded with light offers four levels of living with breathtaking Boston skyline views and a roof deck perfect for entertaining. Nearly 10' ceilings, oversized windows, richly stained hardwood floors, decorative crown molding and the finest details create a luxurious retreat. The main level has an open floor plan with designer chef's kitchen that includes an eight-burner Viking stove, pantry and adjoining family room. In addition, a flexible dining or living room offers City views. The top two floors have a striking master suite with gas fireplace as well as four additional bedrooms. A bedroom in the garden level is perfect for an au-pair and includes a playroom with kitchenette, wine fridge, and direct access to the back yard. Great location close to Washington Square, Coolidge Corner, The Village, BHS, & public transportation.
33 Winthrop Rd #2, Brookline, MA 02445 is a 6 bedroom, 5 bathroom, 4,900 sqft condo in Aspinwall Hill, built in 2018. It last sold for $3,125,000 on Oct 16, 2020. More recently, it was listed as a rental in November 2023 with an asking price of $12,500 per month. That rental listing was removed on April 17, 2024. It is currently off market. The Trulia Estimate is $3,594,500, with a rent estimate of $7,451/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 33 Winthrop Rd #2

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Cement ConcretePatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: CondoArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 0.31 acres

Price History for 33 Winthrop Rd #2

DatePriceEventSource
04/17/2024ListingRemovedZillow Rentals
11/02/2023$12,500Listed For RentZillow Rentals
10/16/2020$3,125,000Sold
N/A
08/21/2020$3,250,000PendingToActiveAgent Provided
08/21/2020$3,250,000PendingAgent Provided
06/09/2020$3,250,000Listed For SaleAgent Provided

Market trends in Brookline

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
$333MoM
Sale-to-List Price
99.9%
0.9%MoM
Price per sq ft
$814
$5MoM
Available listings
238
11MoM
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Property Tax and Assessment

Year2025
Tax$29,422
Assessment$2,981,000
Home facts updated by county records

Comparable Sales for 33 Winthrop Rd #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
757 Washington St #1, Brookline, MA
0.48
Condo
$2,750,000
09/24/25
5
4.5
3,259
216 Aspinwall Ave #3, Brookline, MA
0.76
Condo
$3,260,000
04/13/26
4
4.5
3,700
90 Addington Rd #2, Brookline, MA
0.25
Condo
$2,850,000
04/17/26
5
3.5
3,250
90 Addington Rd #1, Brookline, MA
0.25
Condo
$2,649,000
06/25/26
5
4
3,392
39 Verndale St #39, Brookline, MA
0.72
Condo
$2,725,000
06/18/26
5
4
3,234
57 University Rd #3, Brookline, MA
0.24
Condo
$3,265,000
05/01/26
4
3.5
2,605
75 Greenough St #2, Brookline, MA
0.27
Condo
$3,100,000
04/30/26
4
4
2,610
757 Washington St #2, Brookline, MA
0.48
Condo
$3,000,000
02/27/26
5
4.5
3,838
140 Columbia St #2, Brookline, MA
0.66
Condo
$2,410,000
09/22/25
4
3.5
2,690
71 Greenough St #1, Brookline, MA
0.27
Condo
$3,019,999
04/03/26
3
3.5
2,552

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Assigned Schools

These are the assigned schools for 33 Winthrop Rd #2.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Aspinwall Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Aspinwall Hill

  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
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  • Billy W.
    "There is a leash law, and dog owners must pick up their dog's poop in a bag."
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  • Billy W.
    "It has a public park at the very top of the hill."
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  • Billy W.
    "I can either drive or take public transportation."
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  • Billy W.
    "There is only one park on this hill, but a short walk can lead you to bigger parks and playgrounds."
    1
    Flag
  • Jessicalmartin
    "Beautiful and quiet streets, shops, near to the T. Gorgeous in the snow! A really lovely place to live, I’ve been here about 3 years so far. "
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  • Harumi T.
    "It is so nice to live here. "
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Apartments for Rent

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Homes for sale near 33 Winthrop Rd #2

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Off Market Homes Near 33 Winthrop Rd #2

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