153 Cypress St, Brookline, MA 02445
Property image
Property image
OFF MARKET

$2,405,600

Trulia Estimate
  • 6 Beds
  • 3 Baths
  • 3,158 sqft

153 Cypress St, Brookline, MA 02445

Est. Refi. Payment $14,322/mo*
Refinance Your Home
Currently Off Market - Sold Aug 21, 2023 for $2,200,000

Home Value

Trulia Estimate
$2.41M
Since last month
Decreased$50K (-2%)
Since last year
Decreased$27K (-1.1%)
Since last sale
Increased$206K (+9.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +55% in the last 10 years
MonthEstimated value
2026
August 2026$2.41M
August 2026$2.4M
July 2026$2.46M
June 2026$2.51M
May 2026$2.51M
April 2026$2.49M
March 2026$2.44M
February 2026$2.35M
January 2026$2.34M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Irving St, Brookline, MA
0.34
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
16 Kennard Rd, Brookline, MA
0.10
Single-Family Home
$2,000,000
08/14/26
8
5
5,076
24 Blake Rd, Brookline, MA
0.34
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377
54 Clark Rd, Brookline, MA
0.21
Single-Family Home
$2,325,000
07/24/26
7
4
4,544
50 Waverly St, Brookline, MA
0.29
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
21 Hancock Rd, Brookline, MA
0.43
Single-Family Home
$2,385,000
12/17/25
4
3
2,286
236 Walnut St, Brookline, MA
0.15
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
9 Greenough St, Brookline, MA
0.40
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104
43 Waverly St, Brookline, MA
0.31
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
20 E Milton Rd #3, Brookline, MA 02445
0.06
$947,300
3
2
1,300
Off Market
9 E Milton Rd, Brookline, MA 02445
0.04
$999,999
8
3
3,898
Recently Sold
157 Cypress St #2, Brookline, MA 02445
0.02
$1,795,000
4
3.5
2,075
Recently Sold
11 E Milton Rd, Brookline, MA 02445
0.05
$2,342,000
12
3
4,515
Off Market
323 Boylston St #502, Brookline, MA 02445
0.09
$1,515,700
3
2
1,709
Off Market
17 Milton Rd, Brookline, MA 02445
0.07
$2,548,500
12
5
4,911
Off Market
110-112 Cypress St, Brookline, MA 02445
0.11
-
2
2
1,488
Off Market
110-112 Cypress St #302, Brookline, MA 02445
0.11
-
2
1
982
Off Market
110 Cypress St #112, Brookline, MA 02445
0.11
$874,400
1
1
1,366
Off Market
110 Cypress St #Penthouse 12, Brookline, MA 02445
0.11
$976,800
2
2
1,212
Off Market
110 Cypress St #Penthouse 8, Brookline, MA 02445
0.11
$845,200
1
2
1,196
Off Market

Local Information

  • Map ViewExplore the area around 153 Cypress St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1891
3,158 sqft
$762/sqft
Garage

About this House

Unique Queen Anne with original architectural detail: spindlework on front porch, patterned shingles, bow shapes and bay windows. Sep. entrance office offers great possibilities for au-paire or first floor guest room in one of Brookline's friendliest neighborhoods. Lovely entry with dramatic stairs, bow shaped LR and spacious DR both with fireplaces. Renov. kitchen with cherry cabinets, black granite counters, and stainless appliances. Four bedrooms on 2nd and oversized hall bath that also connects to primary BR .Two delightful bedrooms on 3rd, with bays and skylights and hall bath. 2023 FHA furnace and hot water tank. Leafy side street is entrance to large two-car garage and extra parking. Side corner garden with hundreds of tulip bulbs and perennials for spring delight and secluded rear yard for play or dining. Near cafes, shops, MBTA, Brookline High and Lincoln School.Convenient access to Medical Area and downtown Boston.
153 Cypress St, Brookline, MA 02445 is a 6 bedroom, 4 bathroom, 3,158 sqft single-family home built in 1891. It last sold for the $2,195,000 asking price on Aug 21, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,405,600.
Last check for updates: about 5 hours ago
Listed by Susan and Jen Rothstein Team, (617) 875-2088
Hammond Residential Real Estate, (617) 731-4644
Bought with: Jenny Searles Margulies, (317) 407-7439, First Boston Realty International, (617) 482-3333
Source: MLS PIN, MLS#73117224

Home Details for 153 Cypress St

Interior Features

Interior Details
Basement: Full,Bulkhead,UnfinishedNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 3158 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas Dryer, Washer HookupAppliances: Gas Water Heater, Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer, Range HoodDishwasherDisposalDryerLaundry: Gas Dryer Hookup,Washer Hookup,In BasementRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Dining Room, Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Bay/Bow/Box, Storm Window(s)Door: Storm Door(s)Flooring: Tile, Hardwood, Flooring - Hardwood, Flooring - Engineered Hardwood
Levels, Entrance, & Accessibility
Accessibility: Accessible EntranceFloors: Tile, Hardwood, Flooring Hardwood, Flooring Engineered Hardwood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PorchFencing: FencedExterior: Porch, Fenced YardFoundation: Stone
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 3No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 5Parking: Detached,Garage Door Opener,Garage Faces Side,Paved Drive,Paved
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1891
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: Metal Ramp On Side Of House Included.Parcel Number: 41091

Price & Status

Price
List Price: $2,195,000
Status Change & Dates
Off Market Date: Tue Jun 06 2023

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: Brookline
School Information
Elementary School: LincolnHigh School: Brookline High

Building

Building Area
Building Area: 3158 Square Feet

Community

Community Features: Public Transportation, Shopping, Pool, Walk/Jog Trails, Medical Facility, Private School, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 8045 sqft

Miscellaneous

BasementMls Number: 73117224

Additional Information

Public TransportationShoppingPoolWalk/Jog TrailsMedical FacilityPrivate SchoolPublic SchoolT-Station

Price and Tax history

DateEventPrice
Aug 21, 2023
Source: MLS PIN #73117224
Sold
$2,200,000
May 30, 2023
Source: MLS PIN #73117224
Listed For Sale
$2,195,000

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

What Locals Say about Brookline

At least 422 Trulia users voted on each feature.

  • 94 % Say there are sidewalks

  • 90 % Say it's dog friendly

  • 87 % Say it's walkable to restaurants

  • 87 % Say it's walkable to grocery stores

  • 84 % Say people would walk alone at night

  • 81 % Say streets are well-lit

  • 67 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 59 % Say there's wildlife

  • 52 % Say parking is easy

  • 51 % Say they plan to stay for at least 5 years

  • 51 % Say it's quiet

  • 48 % Say neighbors are friendly

  • 40 % Say car is needed

  • 39 % Say yards are well-kept

  • 33 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly "
    0
    Flag
  • Rockygranahan
    "A quick and easy walk to the T. Total commute to downtown Boston from Coolidge Corner ranges between 15-25 minutes consistently."
    0
    Flag
  • Kai Hsin Chang
    "Very convenient to do grocery and most people live here use public transportation because there’s no street parking. People who want to do street parking should apply for parking permits."
    0
    Flag
  • Sydney Reitz
    "Events at the Coolidge corner theatre, Brookline day on Harvard street in Coolidge corner, open holiday meals at the United Parish church"
    0
    Flag
  • Sydney Reitz
    "The sidewalks and streets are well-maintained even in inclement weather. Traffic is only bad around the Longwood medical area and major streets around rush hour. Pub trans is easy and safe."
    0
    Flag
  • Austin Wozniak
    "Multiple dog friendly, off-leash parks in the community and many great places to walk a dog. The community is very dog friendly. "
    0
    Flag
  • Loming1986
    "Only limited (a hand-full) dog parks available, I wish there are more. Many neighbors have dogs and it’s a very dog friendly neighborhood."
    0
    Flag
  • Trulia User
    "Clean, safe and quiet. People are very friendly. Access ti public transportation. Love this place very much."
    0
    Flag
  • Trulia User
    "The neighborhood is great environment to raise a family. It’s peaceful, clean and quiet. We would love to be here to raise our kids here. "
    0
    Flag
  • Trulia User
    "I’v stayed in a hotel in this neighborhood. It is a beautiful area with many shops to explore. Hope to move to this area. "
    0
    Flag
  • Trulia User
    "Near everything. Train across the street, restaurants, coffee shops, etc JP is part of Boston. Vibrant community. Diverse. High incomes mixed with low. "
    1
    Flag
  • Trulia User
    "Yes, the area has many dog parks, both on and off leash. Most apartment buildings are dog friendly and neighbors have been very accepting. "
    0
    Flag
  • Aliana P.
    "It’s a quick commute to downtown, especially if you live on the D line. Very convenient. It’s also a very walkable area with all stores and necessities close by. "
    1
    Flag
  • Juana B.
    "It’s very safe and great school system!! I been leaving here for 11 years and I love it and my kids too"
    2
    Flag
  • Jiyoung W.
    "Lots of other friendly dog owners, plus lots of little parks and green space for pups to run around (especially Amory Park!). Lots of businesses in the area have dog treat jars too!"
    1
    Flag
  • Adriana P.
    "It seems let friendly. Lots of parks and spaces for dogs to run. I don’t have a dog but I have friends with dogs"
    0
    Flag
  • Archana B.
    "Lived here for 5 years. I highly recommend it. It is getting more expensive. Some areas are more family friendly than others. "
    0
    Flag
  • Deiabarroso86
    "Very safe, with a lot of stores around.. Beacon Street is a beautiful street and we have the Reservoir nearby, which is a good place for a walk."
    1
    Flag
  • Josie E.
    "The kids walk to school on a tree-lined street and neighbors know each other. A little oasis in the city "
    4
    Flag
  • Caroline
    "Drive to Watertown or take shuttle provided by my place of employment. Easy access to city via C or D green line. "
    0
    Flag
  • 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
  • Scottcunha311
    "Halloween’s are very popular especially on clark rd. Great location to Cleveland circle and both bu and bc can take train anywhere or easily get a bus there’s no shortsge of things to do"
    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
  • Courtney C.
    "Safe and homey - education is good but property tax is rising. Commute is perfect - only ten minute drive away from my work site. "
    0
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  • Luis B.
    "Lots of commerce within walking distance and easier access to the city by public transportation. Also very good public schools"
    0
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  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
    0
    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
  • Oliver L.
    "I walk to work in the medical area. T stops make getting to the center easy. It is quite possible to live without a car."
    0
    Flag
  • Sophie
    "The community center holds a lot of interesting activities like Mahjong, movies, reading, yoga and concerts. Also we have a greeeat library here!"
    0
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  • Kathy U.
    "Many dog parks around the Coolidge corner area. Many off leash areas too. The dog community it big in this neighborhood "
    0
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  • Heli C.
    "The schools are excellent, and neighbors tend to know each other. We are a ‘suburb’ of Boston but also officially a town with numerous distinct village neighborhoods, most of which are walkable to restaurants and amenities. Brookline has a fairly international mix of people, with families from all over the world coming here to study and work at the nearby Harvard teaching hospitals."
    0
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  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
    0
    Flag
  • Pat B.
    "There's some strange people who are around, but they're harmless. There's lots of daycare places, so if someone has a young kid there's lots of options nearby."
    1
    Flag
  • Billy W.
    "There is only one park on this hill, but a short walk can lead you to bigger parks and playgrounds."
    1
    Flag

LGBTQ Local Legal Protections

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 153 Cypress St

  • What is 153 Cypress St estimated to be worth?
    Trulia's estimated value for 153 Cypress St in Brookline, MA is $2,405,600.
  • What is the price history for 153 Cypress St?
    153 Cypress St in Brookline, MA last sold for $2,200,000 in August 2023.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • Does 153 Cypress St have air conditioning?
    Yes, 153 Cypress St in Brookline, MA has air conditioning.
  • Does 153 Cypress St have a pool?
    Yes, 153 Cypress St in Brookline, MA has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Explore by feature - Outdoor Space

16 rentals with an outdoor space in Brookline, MA

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Off Market Homes Near 153 Cypress St

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