5 Grassmere Rd, Brookline, MA 02467
Property image
Property image
OFF MARKET

5 Grassmere Rd
Brookline, MA 02467

Chestnut Hill
  • 4 Beds
  • 3 Baths
  • 2,290 sqft

$2,025,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $11,724/mo*
Refinance Your Home

$2,025,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $11,724/mo*
Refinance Your Home
4 Beds
3 Baths
2,290 sqft

Local Information

  • Map ViewExplore the area around 5 Grassmere Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Situated in South Brookline on a flat, professionally landscaped and fenced-in gated corner lot, this majestic, all-brick estate offers open-concept living and an abundance of parking and space. In addition to the two-car garage, there is room for another five cars in the new asphalt driveway.
Sun-filled, this renovated Colonial-style residence features four bedrooms, two and one-half bathrooms, gas heat, central A/C, hardwood
floors, recessed lights, crown molding, and custom-designed marble fireplace. The spacious master bedroom accommodates a king-sized bed and has an in suite bathroom and two large closets. Adjacent to the primary living area, a separate entrance leads to the fourth bedroom. The modern kitchen is highlighted by a granite island, two-year old stainless-steel appliances, and gas range. The semi-finished basement offers a bar area, fireplace, and extra storage including a cedar closet. Close to shops, Baker School, Park School, International British School, restaurants, and hospitals.

Property is Unfurnished
Application should be submitted with:
7 month lease -possible19 month lease
1st month rent
last month rent
security deposit
Renter is responsible for utilities (water, electricity, gas) to be established under renter's name
5 Grassmere Rd, Brookline, MA 02467 is a 4 bedroom, 3 bathroom, 2,290 sqft single-family home in Chestnut Hill. It last sold for $1,349,000 on Dec 2, 2019 (20,654% above the $6,500 asking price). More recently, it was listed as a rental in October 2025 with an asking price of $6,500 per month. That rental listing was removed on November 18, 2025. It is currently off market. The Trulia Estimate is $2,025,200, with a rent estimate of $7,092/month.

Home Highlights

Parking
Attached Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 5 Grassmere Rd

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Central AirHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Sublet/TemporaryAvailable: now

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Price History for 5 Grassmere Rd

DatePriceEventSource
11/18/2025$6,500ListingRemovedZillow Rentals
10/28/2025$6,500Listed For RentZillow Rentals
08/27/2025$6,900ListingRemovedZillow Rentals
08/13/2025$6,900PriceChange
Zillow Rentals
07/25/2025$7,300PriceChange
Zillow Rentals
07/18/2025$7,500Listed For RentZillow Rentals
12/02/2019$1,349,000Sold
N/A
10/23/2019$1,349,000PendingAgent Provided
10/17/2019$1,349,000PriceChange
Agent Provided
09/11/2019$1,399,000PendingAgent Provided
09/04/2019$1,399,000Listed For SaleAgent Provided
06/12/2017$1,100,000Sold
N/A
09/28/1990$35,500Sold
N/A

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$14,722
Assessment$1,491,600
Home facts updated by county records

Comparable Sales for 5 Grassmere Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
227 Bonad Rd, Brookline, MA
0.05
Single-Family Home
$1,950,000
04/16/26
4
3.5
2,371
170 Bonad Rd, Brookline, MA
0.10
Single-Family Home
$1,700,000
04/17/26
3
2.5
2,174
236 Beverly Rd, Brookline, MA
0.31
Single-Family Home
$1,650,000
09/05/25
4
2.5
2,615
173 South St, Brookline, MA
0.17
Single-Family Home
$2,450,000
01/08/26
4
2.5
2,841
394 Vfw Pkwy, Brookline, MA
0.28
Single-Family Home
$1,525,000
07/24/25
4
2.5
3,257
143 South St, Brookline, MA
0.24
Single-Family Home
$1,475,000
11/26/25
4
2
2,044
87 Payson Rd, Brookline, MA
0.35
Single-Family Home
$1,670,000
06/29/26
4
2.5
2,408
Address Not Disclosed, Brookline, MA
0.23
Single-Family Home
$1,735,000
07/01/26
5
3
2,909
55 Bellingham Rd, Brookline, MA
0.40
Single-Family Home
$1,690,000
05/29/26
4
2.5
2,511
55 Goodnough Rd, Brookline, MA
0.35
Single-Family Home
$1,875,000
09/05/25
4
3
2,854

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Grassmere Rd.
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.

Neighborhood Overview

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

What Locals Say about Chestnut Hill

At least 41 Trulia users voted on each feature.

  • 91 % Say there are sidewalks

  • 86 % Say it's dog friendly

  • 81 % Say car is needed

  • 73 % Say they plan to stay for at least 5 years

  • 71 % Say yards are well-kept

  • 71 % Say streets are well-lit

  • 70 % Say there's holiday spirit

  • 66 % Say parking is easy

  • 66 % Say people would walk alone at night

  • 63 % Say it's walkable to restaurants

  • 63 % Say kids play outside

  • 61 % Say it's quiet

  • 57 % Say there's wildlife

  • 55 % Say there are community events

  • 54 % Say it's walkable to grocery stores

  • 43 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • Dma333
    "Diverse, safe, close to everything, friendly neighbors, great schools, playgrounds in walking distance"
    0
    Flag
  • Steve L.
    "Hancock Village in Chestnut Hill is a good place to live overall. Sometimes the management office puts together special functions like handing out cider doughnuts in the fall, or flowers to plant - both gratis. (And more as well but too much to detail)."
    4
    Flag
  • Dma333
    "Block party in September Close to a great school Playgrounds nearby Diverse community Easy access to many communities "
    1
    Flag
  • Szonja.ruppert
    "Lots of greens, parks, even bags for dogpoop is put to parks. Not many pet shops in walking distance"
    0
    Flag
  • Jawaher A.
    "Good schools, no stealing, good neighbors, good place to kids to play, not far away from BU university, there is driving school, all government facilities around us, Uber so expensive but it is available all time, there is ice cream shop and Starbucks around us also a lot of restaurants and malls "
    2
    Flag
  • Jawaher A.
    "I love this area coz its safe and beautiful and the neighbors are nice and kind and there is a lot of great people "
    0
    Flag
  • Fish r.
    "Lovely neighborhood that's close to anything and everything -- shopping, restaurants, movies, doctors, gyms, public transportation, Soule recreation center & golf course, etc. Very safe, with lots of places to go for peaceful walks. I have lived here for nearly two decades and love it."
    5
    Flag
  • Jacquizieff
    "It an a upscale and snobby neighborhood where people don’t talk to each other. We never see kids and kids make no friends in the neighborhood. Clean safe closet To Boston. Nothing around. No walking distance to anything. Supermarket and gas is over priced. "
    0
    Flag
  • Robert B.
    "Wooded neighborhood surrounded by open space on 3 sides - farm stand and parks nearby. Safe, easy commute, great schools."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

355 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

75 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

540 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

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Explore by feature - Washer/dryer

935 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

24 rentals with an outdoor space in Brookline, MA

Homes for sale near 5 Grassmere Rd

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Off Market Homes Near 5 Grassmere Rd

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