ABSOLUTELY INCREDIBLE OPPORTUNITY AT THIS PRICE!!!!!! A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.
South Brookline, located between Jamaica Pond and the Chestnut Hill Reservoir, is a residential and village-style Brookline neighborhood with leafy park edges and a low-rise streetscape. The neighborhood’s character concentrates around the Cleveland Circle junction, where cafés, small eateries, and everyday storefronts cluster beside the Green Line tracks. Coolidge Corner Theatre and Brookline Booksmith serve as cultural pillars with a distinctly local cadence. Side streets feature a mix of brick apartment houses, classic triple-deckers, and single-family homes with deep setbacks. The Emerald Necklace paths and nearby water views shape a walk-and-roll routine. A steady flow of transit riders and runners gives the area a lived-in, city-meets-suburb tempo.
Provided by Walk Score and Local Logic
Offer insights
284 Woodland Rd · $2,595,000
$2.56M and above
75% chance or better to win
Why $2.56M+ is a strong offer
DAYS ON MARKET
50 days
The average home goes pending in 25 days.
SALE-TO-LIST
100.1%
Most homes are selling 0% above list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
11 rooms
Study
Fireplace in the living room
Full bathrooms with tiled tub and shower
Full basement, partially finished
Bedrooms
5 bedrooms, all on the second floor
Bathrooms
4 full bathrooms and 1 half bathroom
Kitchen
Range, dishwasher, disposal, microwave, refrigerator, and freezer
Dining area
Stone, granite, or solid-surface countertops
Kitchen island
Remodeled kitchen
Wood flooring
Laundry & utility
Washer and dryer
Laundry in the basement
Flooring
Tile
Pine
Wood
Heating & cooling
Forced-air and steam heating
Oil heat
Central air conditioning
Exterior features
Fenced and enclosed
Deck
Patio
In-ground pool
Storage
Sprinkler system
Home design
Single-family residence
Parking
2-car garage
4 open parking spaces
Garage door opener
Paved driveway
Off-street parking
Security
Security system
Construction
Stone construction
Block foundation
Other roof type
Utilities
Public water
Public sewer
200+ amp electrical service
HOA & community
Near public transportation, shopping, parks, walking and jogging trails, golf, bike paths, houses of worship, private and public schools, and a T station
Electricity and solar
View estimated energy costs and solar savings for this home
Charming 5 bed, 4.5 bath c1933 Cape situated on .52-acre in picturesque Chestnut Hill. 3,913SF home is beautifully designed to enhance character. Architecture highlighted by south-facing exposures, period details, and wide plank floors. Ideal layout for entertaining combined with family comfort. Living room with fireplace and french doors open to patio. Spacious family room with bespoke built-ins. Dining room flows into family ‘hub’, showcasing renovated kitchen with eat-in, sitting area, and backyard access. Mudroom offers ideal come-and-go to driveway/2-car garage. 2nd floor features sunny en-suite primary with balcony. Four beds, study, and three full baths complete floor, including private guest quarters accessed by separate stairs. Lower level houses laundry, rec room, and storage. Playful yard with pool and mature landscape create a magical escape from city. Ideal Brookline location, close by “The Street”, and central to area’s top schools.
Public Records
Oct 14, 2004
Sold
$1,535,000
$392/sq ft
MLS PIN #70014764
Oct 13, 2004
Sold
$1,550,000
$396/sq ft
May 28, 2004
Listing Removed
—
Apr 2, 2004
Listed
$1,850,000
$473/sq ft
CHARMING CAPE/COLONIAL WITH SLATE ROOF IN DESIRABLE CHESTNUT HILL LOCATION ON OVER 1/2 ACRE LANDSCAPED GROUNDS.6 BEDROOMS, 4 1/2 BATHS. SEPARATE MASTER SUITE WITH BEAMED CEILING & BALCONY. LIVING ROOM W/ANTIQUE WIDE PLANK FLOORING OPENS TO BRICK PATIO AND INGROUND POOL.SPRINKLER SYSTEM. CLOSE TO CHESTNUT HILL MALL & MBTA GREEN LINE.
Year
Property tax
Land + Additions
Assessment*
2023
$26,255 (+2.7%)
$1,393,200 + $1,240,200
$2,633,400
2022
$25,556 (+8.1%)
$1,326,800 + $1,181,100
$2,507,900
2021
$23,633 (+9.7%)
$1,275,800 + $1,135,700
$2,411,500
2020
$21,549 (+5.9%)
$1,159,800 + $1,120,500
$2,280,300
2019
$20,349 (−11.1%)
$1,104,600 + $1,067,100
$2,171,700
2018
$22,902 (+1.5%)
$1,169,500 + $1,251,400
$2,420,900
2017
$22,564 (+3.1%)
$1,103,300 + $1,180,500
$2,283,800
2016
$21,875 (+4.4%)
$1,031,200 + $1,068,100
$2,099,300
2015
$20,954 (−2.1%)
$963,700 + $998,300
$1,962,000
2014
$21,413 (+0.7%)
$875,900 + $1,004,100
$1,880,000
2013
$21,264 (+2.2%)
$850,400 + $974,800
$1,825,200
2012
$20,807 (+17.5%)
$850,400 + $974,800
$1,825,200
2011
$17,704 (+3.0%)
$814,700 + $752,000
$1,566,700
2010
$17,187 (+3.0%)
$814,700 + $752,000
$1,566,700
2009
$16,692
$809,600 + $751,900
$1,561,500
Public record
Public record
Permits
Beds
5
Baths
4.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.52 Acres
Year renovated
1975
Finished Sq. Ft.
3,467
Unfinished Sq. Ft.
—
Total Sq. Ft.
3,467
Year built
1933
Style
Single Family Residential
County
Norfolk County
APN
43081
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 21, 2023.
Oct 19, 2015 • Active
Residential electrical
Rewire the electrical system in a second floor bathroom.
Bathroom
Electrical
Oct 13, 2015 • Active
Residential plumbing
Perform plumbing work in a bathroom.
Bathroom
Plumbing
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Local insights from Redfin agents
Brookline will continue to be a Seller's market for the foreseeable future, driven by restrictive zoning laws that have limited increases in housing production and a stable population with relatively low turnover. This has resulted in a massive...
supply/demand imbalance that is unlikely to change.
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.15% chance of being in a wildfire in next 30 years
5/10 Heat Factor
7 days above 96° expected this year, 15 days in 30 years
6/10 Wind Factor
56% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Chestnut Hill, MA • 02467
Average low and high temperatures (°F)
34
21
36
22
51
33
59
42
68
52
80
62
84
66
79
61
74
57
64
48
52
38
39
26
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
83/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Chestnut Hill. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
7.9 hrs
4.7 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 284 Woodland Rd
$2,592,878
$2,122 under list price of $2.60M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $2.3M to $2.8M.