44 Rolling Ln, Chestnut Hill, MA 02467
Property image
Property image
OFF MARKET

44 Rolling Ln
Chestnut Hill, MA 02467

  • 3 Beds
  • 2 Baths
  • 2,843 sqft

$1,673,100

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $9,926/mo*
Refinance Your Home

$1,673,100

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $9,926/mo*
Refinance Your Home
3 Beds
2 Baths
2,843 sqft

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1950
Living Area
2,843 sqft
Price/Sqft
$588

About this House

Beautifully updated and light filled, this spectacular Chestnut Hill raised ranch boasts a fabulous open floor plan, integrating the great use of space for both cozy, informal living and grand scale entertaining. The gracious entry foyer leads into the stunning living room with several picture windows, lovely built-in bookcases & high ceilings. Cleverly separated by a double sided fireplace, the living area flows seamlessly into the dining room and sunken family room featuring walls-of-glass, bluestone floors and beautiful views of the secluded yard and deck. The well designed cook's kitchen has an abundance of cabinet storage, stainless appliances, granite counters, and a quartz breakfast bar. On this level there are 2 generously sized bedrooms, each with custom designed closets. There is also a full bathroom. The lower level offers the 3rd bedroom & 2nd full bath, an entertainment sized game room with a wet bar, and access to the 2 car garage. Huge walk-up attic and basement storage.
44 Rolling Ln, Chestnut Hill, MA 02467 is a 3 bedroom, 2 bathroom, 2,843 sqft single-family home built in 1950. It last sold for $1,136,000 on Feb 22, 2018. It is currently off market. The Trulia Estimate is $1,673,100, with a rent estimate of $5,927/month.

Home Details for 44 Rolling Ln

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 9583 sqft

Price History for 44 Rolling Ln

DatePriceEventSource
02/22/2018$1,136,000Sold
N/A
11/14/2017$1,199,000ListingRemovedAgent Provided
10/04/2017$1,199,000Listed For SaleAgent Provided

Market trends in Newton

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.53M
$17.5KMoM
Sale-to-List Price
100.0%
0.7%MoM
Price per sq ft
$619
$17MoM
Available listings
321
23MoM
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Comparable Sales for 44 Rolling Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
16 High Rock Ter, Newton, MA
0.02
Single-Family Home
$1,450,000
04/14/26
4
2.5
1,946
145 Pond Brook Rd, Newton, MA
0.13
Single-Family Home
$1,270,000
07/30/25
4
3
1,840
14 Rolling Ln, Newton, MA
0.06
Single-Family Home
$2,000,000
12/22/25
4
3.5
2,898
78 Vine St, Newton, MA
0.28
Single-Family Home
$1,507,000
06/10/26
5
3
2,388
18 Wolcott Rd, Brookline, MA
0.54
Single-Family Home
$1,523,000
11/10/25
4
1.5
2,243
65 Lagrange St, Brookline, MA
0.40
Single-Family Home
$1,270,000
12/08/25
4
3
4,084
360 Brookline St, Newton, MA
0.66
Single-Family Home
$1,290,000
11/07/25
3
3
3,725
84 Cynthia Rd, Newton, MA
0.52
Single-Family Home
$1,553,180
06/18/26
4
3
3,088
95 Beverly Rd, Brookline, MA
0.55
Single-Family Home
$1,645,000
04/10/26
3
2
2,352
17 Tirrell Cres, Newton, MA
0.41
Single-Family Home
$1,550,000
06/16/26
3
2.5
1,500

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Rolling Ln.
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 Newton

At least 596 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 91 % Say there are sidewalks

  • 83 % Say parking is easy

  • 83 % Say people would walk alone at night

  • 79 % Say it's walkable to restaurants

  • 78 % Say car is needed

  • 70 % Say there's holiday spirit

  • 69 % Say kids play outside

  • 69 % Say yards are well-kept

  • 67 % Say streets are well-lit

  • 67 % Say it's walkable to grocery stores

  • 64 % Say there's wildlife

  • 61 % Say it's quiet

  • 61 % Say they plan to stay for at least 5 years

  • 59 % Say neighbors are friendly

  • 44 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Joao
    "Oak Hill and Newton in general are great for raising families, with top rated schools and a community that is very focused on children and their education "
    0
    Flag
  • Joao
    "There are people walking dogs all the time and they take good care to clean up after them. Dog owners are welcome!"
    0
    Flag
  • Justin Buck
    "The neighborhood has fantastic access to the Cove on the Charles River, a wonderful park. The area is quiet, but has amazing accessibility to the whole Boston area via I-90, I-95, Green Line, Commuter Rail, and Express Bus. The community hosts an annual PorchFest block party with dozens of bands playing on front porches, which is a highlight every year."
    0
    Flag
  • Soniamgregory
    "Suburban with walkable stores and activities. Easy access to commuter rail into Boston. Great public schools "
    0
    Flag
  • Timothyasmth
    "Great place to raise a family. Safe neighborhoods, good schools. Close to transportation and highways. "
    0
    Flag
  • Justindbuck
    "The community block party and porchfest with live music are traditional yearly events. Great neighborhood for Halloween."
    0
    Flag
  • Commave
    "There is a grand piano out on the town green all summer and most evenings people gather there to eat and admire the community-maintained gardens while they listen to whoever plays. The Harvest Fair in the fall is well attended and a great time. The weekly farmers market is first-rate as is swimming in Crystal Lake. And then there’s Halloween, when so many people go all-out. "
    0
    Flag
  • Shermaderma
    "Great neighborhood. Walking to distance to everything; schools, groceries, restaurants, fast food, commuter rail and buses. People are out and about and friendly. Streets are safe. "
    0
    Flag
  • Pmellios
    "I grew up in newton. Lots to do! Crystal lake, 4th of July at Fessenden, farmers markets. Nice sense of community and very safe! Now feels more urban but still come back from downtown Boston to visit family on the weekends."
    1
    Flag
  • Trulia User
    "I have lived in West Newton and then Newton Centre since 1978, raised three kids here, and have retired here. A wonderful town filled with friendly and high achieving people. "
    0
    Flag
  • Trulia User
    "Lots of dogs, lots of parks, nice people, great schools, lots of restaurants and stores within walking distance."
    0
    Flag
  • Trulia User
    "Very nice neighborhood Live here for twenty years I do not commute to work. Self employed "
    0
    Flag
  • Trulia User
    "Wonderful city. Safest of its size in the whole country. First class schools, wonderful library, convenient shopping, lots of restaurants. Newton is called the garden city because of the extensive trees found everywhere."
    0
    Flag
  • Trulia User
    "Friendly dog walkers are out and about at all hours. Traffic is pretty slow - no fast speeding vehicles. "
    0
    Flag
  • Trulia User
    "A nice neighborhood of 1- and 2 family homes. A vibrant commercial area with some new buildings with apartments, stores, and restaurants. "
    3
    Flag
  • Eugen J.
    "The area is known for its picturesque New England-style homes, tree-lined streets, and friendly community. The neighborhood is also home to the beautiful Upper Falls Greenway, which offers residents a peaceful spot to take a walk or have a picnic."
    1
    Flag
  • Trulia User
    "I live in newton one year,it is safe and quiet, very beautiful town,people are friendly,everything is good for me."
    1
    Flag
  • Trulia User
    "We have a neighborhood block party in the spring and a town-wide Village Day in the fall. "
    1
    Flag
  • Trulia User
    "Safe area to live with a family, close to everything and schools are great. Commute to Boston by commuter rail that is quite expensive"
    0
    Flag
  • Trulia User
    "I like living here, it is convenient, quiet and nice, the people are friendly They organize town events "
    1
    Flag
  • Trulia User
    "Close knit community, close to T station and vibrant city center that is really convenient for all. "
    0
    Flag
  • Trulia User
    "It’s a nice neighborhood, very quiet, good school district, access to public transportation and restaurants."
    0
    Flag
  • Trulia User
    "I’m only a few minutes away from work. It’s a great location to be and to raise kids. Cute little shops that just opened up as well. "
    0
    Flag
  • Trulia User
    "They would like it cause there is a trail next to charles river people walk, run, bike and it is pets friendly "
    0
    Flag
  • Trulia User
    "The Italian festival is one of my favorite events in Newton. Also, I should include how wonderful the community is."
    0
    Flag
  • Trulia User
    "Best schools in the US, beautiful neighborhood with easy accessibility to public transportation and restaurants "
    0
    Flag
  • Trulia User
    "Very convenient to all downtown areas and buses are always on time and never overcrowded and nice bus drivers"
    0
    Flag
  • Trulia User
    "Easy access to the T and bus lines and some major commuter thoroughfares, but traffic can be heavy. The highway however is not too close"
    0
    Flag
  • Trulia User
    "There recently have been more dog owners. Most of them do pick up poop after the dog, but there ate a few people that don't. Otherwise most of the dog owners I know are super friendly and nice."
    0
    Flag
  • Trulia User
    "while I would like more than one event, there is a nice street fair each summer that's good for kids. "
    0
    Flag
  • Trulia User
    "massive dog park where there are lots of friendly dogs and owners (say hi to spike) and great small trails for dogs, "
    0
    Flag
  • Trulia User
    "It has a nice balance of close to the city and in walking distance of town center and public transit and parks!"
    1
    Flag
  • Yogeshreddy
    "Safe, kid friendly neighborhood. Suburban feel but close to many locations. Easy access to highways. "
    0
    Flag
  • Rebecca
    "My neighborhood is quiet, safe and close to the commuter rail and some restaurants. It’s a very pleasant area."
    1
    Flag
  • Rebecca
    "Many people in the neighborhood have dogs and there are some nice places to walk them. A few parks and trails easy to find."
    0
    Flag
  • Matt K.
    "Great place for kids. Nice restaurants around too. Plenty of green space and parks. The driving is a bit crazy "
    0
    Flag
  • Robert S.
    "Place where kids can walk to friends house and the park without worry. Great place for being part of a community and feeling a sense of belonging"
    0
    Flag
  • Rita N.
    "My neighborhood is a great place to live and raise kids too, i can highly recommend it to whoever is looking for an extraordinary place to live and build a family"
    0
    Flag
  • Rconlin13
    "There are parks such as Skyline and Millennium parks that are nice to visit. The side streets are quiet which are nice to walk on."
    0
    Flag
  • Babpta
    "various parks and places to walk you pet. must keep the dog on a leash always remember to clean up, you could be fined"
    1
    Flag

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Homes for sale near 44 Rolling Ln

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Off Market Homes Near 44 Rolling Ln

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