44 Penniman Rd, Brookline, MA 02445
OFF MARKET

44 Penniman Rd
Brookline, MA 02445

  • 5 Beds
  • 4.5 Baths
  • 5,706 sqft

$4,800,900

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $28,381/mo*
Refinance Your Home

$4,800,900

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $28,381/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,706 sqft

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1918
Living Area
5,706 sqft
Price/Sqft
$841
Parking
Garage

Description

44 Penniman is an incredibly handsome arts and crafts colonial on one of the most desirable streets in Brookline's Fisher Hill. Enter through awarm and welcoming foyer to the wood-paneled living room with a spacious study facing the beautiful and thoughtfully landscaped yard. The home offers a large and spacious dining room that is perfect for entertaining & a sunlit kitchen with custom cabinetry and top appliances. The home consists of 5 spacious bedrooms and 4.5 bathrooms over 5,706 sq ft, including a luxurious master suite. The home also offers a large, sunny third floor and a lower level featuring a large open space and a temperature-controlled wine cellar. The home was substantially renovated in 2010-2011 to also include new windows, updated wiring (including sound) and new systems throughout. An updated two-car garage completes this offering.
44 Penniman Rd, Brookline, MA 02445 is a 5 bedroom, 5 bathroom, 5,706 sqft single-family home built in 1918. It last sold for $4,200,000 on Jun 30, 2023 (3% above the $4,075,000 asking price). It is currently off market. The Trulia Estimate is $4,800,900, with a rent estimate of $8,469/month.

Home Details for 44 Penniman Rd

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5706 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup, Icemaker ConnectionAppliances: Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Plumbed For Ice MakerDishwasherDisposalDryerLaundry: First Floor,Electric Dryer Hookup,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Steam,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Steam
Fireplace & Spa
Number of Fireplaces: 4Has a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Floors: Hardwood
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: SlatePatio / Porch: PatioExterior: PatioFoundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Detached,Paved Drive
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1918
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: BrickNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: B:259 L:0004 S:0000, 38939

Price & Status

Price
List Price: $4,075,000
Status Change & Dates
Off Market Date: Thu Feb 09 2023

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: Brookline
School Information
Elementary School: HeathJr High / Middle School: HeathHigh School: Bhs

Building

Building Area
Building Area: 5706 Square Feet

Community

Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, UniversityNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 9531 sqft

Miscellaneous

BasementMls Number: 73077701

Additional Information

Public TransportationShoppingPoolTennis Court(s)ParkWalk/Jog TrailsStable(s)GolfMedical FacilityLaundromatBike PathConservation AreaHighway AccessHouse of WorshipMarinaPrivate SchoolPublic SchoolT-StationUniversity
Last check for updates: about 5 hours ago
Listed by Marika Feuerstein
Hammond Residential Real Estate, (617) 731-4644
Bought with: Joan Solomont, (617) 645-9193, Coldwell Banker Realty - Brookline, (617) 731-2447
Source: MLS PIN, MLS#73077701

Price History for 44 Penniman Rd

DatePriceEventSource
06/30/2023$4,200,000Sold
MLS PIN #73077701
02/09/2023$4,075,000Listed For SaleMLS PIN #73077701
10/30/2020$3,350,000Sold
N/A
09/15/2020$3,650,000Listed For SaleAgent Provided
05/14/2010$2,000,000Sold
N/A
01/27/2010$2,200,000Listed For SaleAgent Provided
05/31/1990$655,000Sold
N/A

Market trends in Brookline

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$16.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$796
$17MoM
Available listings
253
15MoM
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Property Tax and Assessment

Year2025
Tax$38,756
Assessment$3,926,600
Home facts updated by county records

Comparable Sales for 44 Penniman Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Cleveland Rd, Brookline, MA
0.18
Single-Family Home
$4,600,000
05/04/26
5
6.5
4,300
34 Hyslop Rd, Brookline, MA
0.35
Single-Family Home
$4,125,000
05/28/26
5
4.5
4,001
282 Buckminster Rd, Brookline, MA
0.29
Single-Family Home
$4,100,000
04/27/26
6
4.5
5,058
401 Clinton Rd, Brookline, MA
0.13
Single-Family Home
$2,200,000
06/15/26
5
3.5
3,463
43 Druce St, Brookline, MA
0.28
Single-Family Home
$3,285,000
05/14/26
5
4.5
3,658
8 Penniman Rd, Brookline, MA
0.07
Single-Family Home
$3,085,000
04/29/26
6
5.5
3,907
167 Willard Rd, Brookline, MA
0.22
Single-Family Home
$3,400,000
09/23/25
4
3.5
3,298
278 Clinton Rd, Brookline, MA
0.22
Single-Family Home
$6,700,000
06/24/26
5
6.5
6,658
189 Clinton Rd, Brookline, MA
0.40
Single-Family Home
$3,318,000
04/23/26
6
4
4,633
323 Clark Rd, Brookline, MA
0.45
Single-Family Home
$2,995,000
03/04/26
5
4.5
3,370

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Penniman 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.

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.
  • Rockygranahan
    "A quick and easy walk to the T. Total commute to downtown Boston from Coolidge Corner ranges between 15-25 minutes consistently."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Dma333
    "Diverse, safe, close to everything, friendly neighbors, great schools, playgrounds in walking distance"
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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 "
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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
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  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
    0
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  • 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

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Homes for sale near 44 Penniman Rd

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Off Market Homes Near 44 Penniman Rd

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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.