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

$3,162,800

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 3,873 sqft

44 Cypress St, Brookline, MA 02445

Emerson Garden
Est. Refi. Payment $18,822/mo*
Refinance Your Home
Currently Off Market - Sold May 15, 2017 for $2,100,000

Home Value

Trulia Estimate
$3.16M
Since last month
Decreased$117K (-3.6%)
Since last year
Increased$66K (+2.1%)
Since last sale
Increased$1M (+50.1%)
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 +59% in the last 10 years
MonthEstimated value
2026
August 2026$3.15M
July 2026$3.27M
June 2026$3.26M
May 2026$3.27M
April 2026$3.27M
March 2026$3.23M
February 2026$3.11M
January 2026$3.03M
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
0.16
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104
0.31
Single-Family Home
$2,300,000
10/15/25
5
3.5
3,873
0.04
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
0.06
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676
0.17
Single-Family Home
$3,019,999
04/03/26
4
3
3,422
0.29
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
0.39
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377
0.45
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
0.45
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
0.22
Single-Family Home
$2,385,000
12/17/25
4
3
2,286

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
0.04
$2,445,000
4
2
2,383
Recently Sold
0.02
$1,307,200
2
2
1,503
Off Market
0.03
$875,000
1
1
1,131
Recently Sold
0.03
$1,869,700
4
2
2,425
Off Market
0.07
$1,800,000
5
2
2,252
Recently Sold
0.06
$935,000
2
1
1,115
Recently Sold
0.06
$1,115,800
3
2
1,608
Off Market
0.07
-
5
3.5
2,645
Off Market
0.06
$3,350,000
4
2.5
2,676
Recently Sold
0.07
$3,068,100
5
4.5
3,693
Off Market
0.05
$1,741,500
5
2
2,310
Off Market
0.08
$1,237,100
3
2
1,415
Off Market

Local Information

  • Map ViewExplore the area around 44 Cypress St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1890
Living Area
3,873 sqft
Price/Sqft
$817

About this House

Built in 1890, this attached Shingle-Style Victorian era single family home offers exquisite details including: inlaid hardwood floors, beautiful carved fireplace mantels and original tiled hearths, molding, millwork and ten foot ceilings. It has been well maintained and updated by its present owners. The modern kitchen was custom designed with hand-crafted cabinetry, an eating area, central work island, and abundant light from sliding doors that lead to a patio and yard. The 1st floor has large scale entertaining rooms. The master on the 2nd floor has a large walk -in closet and bathroom with soaking tub and separate shower. An office and 2 other bedrooms share a bathroom on this level. The 3rd floor has a vaulted ceiling playroom, 2 more bedrooms, a bathroom and storage. The basement is unfinished but has tall ceilings and excellent storage. There is parking for 3 cars on site. It is located 2 blocks from the T, elementary and high schools, Brookline Village shops and library.
44 Cypress St, Brookline, MA 02445 is a 5 bedroom, 4 bathroom, 3,873 sqft single-family home in Emerson Garden, built in 1890. It last sold for $2,100,000 on May 15, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,162,800, with a rent estimate of $7,972/month.

Home Details for 44 Cypress St

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1890Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 5227 sqft

Price and Tax history

DateEventPrice
May 15, 2017
Source: N/A
Sold
$2,100,000
Mar 28, 2017
Source: Agent Provided
Pending
$1,999,000
Mar 21, 2017
Source: Agent Provided
Listed For Sale
$1,999,000
Feb 18, 1994
Source: N/A
Sold
$415,000

Market trends in Brookline

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

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 44 Cypress St

  • What is 44 Cypress St estimated to be worth?
    Trulia's estimated value for 44 Cypress St in Brookline, MA is $3,162,800.
  • What is the price history for 44 Cypress St?
    44 Cypress St in Brookline, MA last sold for $2,100,000 in May 2017.
  • 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.
  • How big is the lot at 44 Cypress St?
    The lot at 44 Cypress St in Brookline, MA is about 0.12 acres (5,227 sq ft).

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