44 Cypress St
Brookline, MA 02445
Emerson Garden
5 Beds
3.5 Baths
3,873 sqft
5 Beds
3.5 Baths
3,873 sqft
Local Information
© Google
-- mins to
Description
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.
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
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 44 Cypress St
|
|---|
Interior Details BasementNumber of Rooms: 11 |
Heating & Cooling Heating: Other, OilAir ConditioningHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 3 |
Fireplace & Spa Fireplace |
|
|---|
Exterior Home Features Roof: AsphaltExterior: Wood |
|
|---|
Year Built Year Built: 1890Year Updated: 1980 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
|
|---|
Units in Building: 1 |
|
|---|
Lot Area: 5227 sqft |
Price History for 44 Cypress St
| Date | Price | Event | Source |
|---|---|---|---|
| 05/15/2017 | $2,100,000 | Sold | N/A |
| 03/28/2017 | $1,999,000 | Pending | Agent Provided |
| 03/21/2017 | $1,999,000 | Listed For Sale | Agent Provided |
| 02/18/1994 | $415,000 | Sold | N/A |
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $24,864 |
| Assessment | $2,519,100 |
Home facts updated by county records
Comparable Sales for 44 Cypress St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.09 | Single-Family Home | $3,525,000 | 08/05/25 | 5 | 2.5 | 3,315 | |
0.10 | Single-Family Home | $2,970,000 | 06/11/25 | 5 | 3 | 2,676 | |
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 | |
0.17 | 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 | |
0.34 | Single-Family Home | $2,125,000 | 07/02/25 | 4 | 2.5 | 2,607 | |
0.45 | Single-Family Home | $2,800,000 | 09/22/25 | 4 | 4 | 3,515 | |
0.39 | Single-Family Home | $2,850,000 | 04/08/26 | 4 | 2.5 | 3,377 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDMAY 12, 2026Lynette Glover, Hammond Residential Real Estate
OFF MARKETMary Lochner, Coldwell Banker Realty - Brookline
SOLDJAN 15, 2026Susanna Stiefel, Insight Realty Group, Inc.
OFF MARKETJosh Ehrenfried, Clear Path
SOLDOCT 31, 2025Diane Marcoux, Coldwell Banker Realty - Wellesley
SOLDFEB 11, 2026The Murphy Group Lexington, William Raveis R.E. & Home Services
OFF MARKETMichael St. Cyr, RE/MAX Preferred Properties
OFF MARKETEzra Stillman, Hammond Residential Real Estate
OFF MARKETJill Streck, Coldwell Banker Realty - Brookline
OFF MARKETPaul Whaley/Charlie Ring Team, Coldwell Banker Realty - Boston
SOLDAUG 15, 2025Suburban Boston Team, Compass
SOLDAUG 4, 2025Fabiola Perry, Coldwell Banker Realty - Wellesley
Assigned Schools
These are the assigned schools for 44 Cypress St.
- 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 44 Cypress St.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
PET FRIENDLY$2,535 - $10,805/moFees may apply1-3 bd1-3 baHancock Village | 1 Hancock Village Dr #G-161,
Chestnut Hill, MA 02467
PET FRIENDLY
NEW - 1 DAY AGOPET FRIENDLY$3,845 - $6,327/moFees may applyStudio-2 bd1-2 baThe Harlo | 1350 Boylston St #Penthouse 1703,
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 FRIENDLY$3,195 - $6,585/moFees may apply1-2 bd1-3 baThe Franklin at Hancock Village | 201 Sherman Rd #F-739,
Chestnut Hill, MA 02467
PET FRIENDLY$2,940 - $5,995/moFees may apply1-3 bd1-3 baThe Adams at Hancock Village | 101 Asheville Rd #A-501,
Chestnut Hill, MA 02467
NEW - 1 DAY AGO
PET FRIENDLY
NEW - 2 DAYS AGOINCOME RESTRICTED
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 FRIENDLY
PET FRIENDLYTotal price$2,749 - $4,435/moStudio-2 bd1-2 baThe Charley | 46 Soldiers Field Pl #44-512,
Brighton, MA 02135
PET FRIENDLYTotal price$2,890 - $3,321/moStudio-1 bd1 baForte at 1440 Beacon | 1440 Beacon St #109,
Brookline, MA 02446
PET FRIENDLY$2,600 - $6,100/moFees may applyStudio-4 bd1-2 baTtoren Flats | 42 N Beacon St #102,
Boston, MA 02108
See more homes for rent inBrookline
Explore by feature
- SPECIAL OFFERPET FRIENDLY$3,195 - $6,585/moFees may apply1-2 bd1-3 baThe Franklin at Hancock Village | 201 Sherman Rd #F-739,
Chestnut Hill, MA 02467 - SPECIAL OFFERPET FRIENDLY$2,940 - $5,995/moFees may apply1-3 bd1-3 baThe Adams at Hancock Village | 101 Asheville Rd #A-501,
Chestnut Hill, MA 02467 - SPECIAL OFFERPET FRIENDLYTotal price$2,890 - $3,321/moStudio-1 bd1 baForte at 1440 Beacon | 1440 Beacon St #109,
Brookline, MA 02446 - SPECIAL OFFERPET FRIENDLY$2,535 - $10,805/moFees may apply1-3 bd1-3 baHancock Village | 1 Hancock Village Dr #G-161,
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
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYTotal price$2,561 - $4,743/moStudio-2 bd1-2 baPelham Hall | 1284 Beacon St #515,
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 44 Cypress St
OFF MARKET
Boston Creative Group, Gibson Sotheby's International Realty
Mary Lochner, Coldwell Banker Realty - Brookline
OPEN SUN, 12-1PMVictor Divine, Berkshire Hathaway HomeServices Commonwealth Real Estate
OPEN SUN, 12-1PM0.36 ACRESHilary Maddox Team, Compass
OPEN SUN, 1-2:30PMBill Gehan, Campion & Company Fine Homes Real Estate
0.41 ACRESHilary Maddox Team, Compass
See more homes for sale inBrookline
Off Market Homes Near 44 Cypress St
SOLDMAY 28, 2026Gina Romm, William Raveis R.E. & Home Services
SOLDMAY 28, 2026Gail Roberts, Ed Feijo & Team, Coldwell Banker Realty - Cambridge
SOLDMAY 28, 2026Mona And Shari Wiener, Hammond Residential Real Estate
SOLDMAY 28, 2026Sarah Fillmann, Coldwell Banker Realty - Boston
SOLDMAY 28, 2026Max Dublin Team, Gibson Sotheby's International Realty
SOLDMAY 27, 2026Kami Gray, Coldwell Banker Realty - Brookline
SOLDMAY 27, 2026Team MA New Listings, Coldwell Banker Realty - Cambridge
SOLDMAY 27, 2026Wendy Pannebaker Matthews, Hammond Residential Real Estate
SOLDMAY 27, 2026Esin Susol, William Raveis R. E. & Home Services
SOLDMAY 27, 2026Michael Carucci, Serhant- See more homes for sale inBrookline
Homes for rent near 44 Cypress St
- PET FRIENDLY$2,535 - $10,805/moFees may apply1-3 bd1-3 baHancock Village | 1 Hancock Village Dr #G-161,
Chestnut Hill, MA 02467 
NEW - 1 DAY AGOAPPLY INSTANTLY
APPLY INSTANTLY
NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLY
APPLY INSTANTLY
APPLY INSTANTLYPET FRIENDLY- See more homes for rent inBrookline
44 Cypress St, Brookline, MA 02445 is a 5 bedroom, 4 bathroom, 3,873 sqft single-family home built in 1890. 44 Cypress St is located in Emerson Garden, Brookline. This property is not currently available for sale. 44 Cypress St was last sold on May 15, 2017 for $2,100,000. The current Trulia Estimate for 44 Cypress St is $3,261,400.