77 Highland Rd, Brookline, MA 02445
Property image
Property image
OFF MARKET

77 Highland Rd
Brookline, MA 02445

High Street Hill
  • 2 Beds
  • 2 Baths
  • 1,452 sqft

$1,453,900

Trulia Estimate
as of Jul 7, 2026

$1,453,900

Trulia Estimate
as of Jul 7, 2026
2 Beds
2 Baths
1,452 sqft

Local Information

  • Map ViewExplore the area around 77 Highland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

For more information on this property, contact William Raveis Real Estate, Mortgage & Insurance at 1-888-699-8876 or contact@raveis.com. **ATTACHED SINGLE FAMILY*SLATE ROOF*PRIVATE CUL-DE-SAC**CONDO ALTERNATIVE**BRAND NEW KITCHEN**OPEN FLOOR PLAN W/ GOOD FLOW ON 1ST FLOOR**GLEAMING WOOD FLOORS & VIBRANT COLORS THROUGHOUT**BOTH BATHS RECENTLY UPDATED**BONUS ROOM IN BASEMENT -COULD BE FAMILY RM OR OFFICE**2011 HTG/CENTRAL AIR**FRENCH DOORS IN DIN. RM LEAD TO BUCOLIC YARD WITH DECK & PATIO**2 PARKING SPOTS**GREAT LOCATION-CLOSE TO MED. DISTRICT, VILLAGE & JAMAICA POND**FIRST SHOWING SUN 6/9 12-2PM**
77 Highland Rd, Brookline, MA 02445 is a 2 bedroom, 2 bathroom, 1,452 sqft single-family home in High Street Hill, built in 1921. It last sold for $902,500 on Jul 21, 2017. It is currently off market. The Trulia Estimate is $1,453,900, with a rent estimate of $4,701/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 77 Highland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick

Property Information

Year Built
Year Built: 1921Year Updated: 1977
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 4239 sqft

Price History for 77 Highland Rd

DatePriceEventSource
07/21/2017$902,500Sold
N/A
07/18/2013$745,000Sold
N/A
06/08/2013$749,000Listed For SaleAgent Provided
07/06/2012$659,000ListingRemovedAgent Provided
05/04/2012$659,000Listed For SaleAgent Provided
12/20/2002$479,000Sold
N/A

Market trends in Brookline

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
$333MoM
Sale-to-List Price
99.9%
0.9%MoM
Price per sq ft
$814
$5MoM
Available listings
238
11MoM
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Property Tax and Assessment

Year2025
Tax$13,391
Assessment$1,356,700
Home facts updated by county records

Comparable Sales for 77 Highland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
71 Highland Rd, Brookline, MA
0.02
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
18 Cushing Rd, Brookline, MA
0.46
Single-Family Home
$1,351,000
01/23/26
2
2
1,230
209 High St, Brookline, MA
0.14
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
14-14A Linden Pl, Brookline, MA
0.65
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380
18 Eldora St, Roxbury, MA
0.65
Single-Family Home
$863,000
10/10/25
4
1.5
2,149
27 Round Hill St, Jamaica Plain, MA
0.72
Single-Family Home
$1,070,000
08/28/25
4
1.5
1,569
11 Kent Sq, Brookline, MA
0.88
Single-Family Home
$1,405,000
06/23/26
2
1.5
1,276
32 Clive St, Jamaica Plain, MA
0.86
Single-Family Home
$1,195,000
07/28/25
3
2
2,203
33 Round Hill St, Jamaica Plain, MA
0.70
Single-Family Home
$1,260,000
08/01/25
4
1.5
2,566
50 Waverly St, Brookline, MA
0.53
Single-Family Home
$2,445,000
05/12/26
4
2
2,383

Nearby homes

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Assigned Schools

These are the assigned schools for 77 Highland 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.

Neighborhood Overview

High Street Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about High Street Hill

At least 31 Trulia users voted on each feature.

  • 98 % Say there are sidewalks

  • 97 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 89 % Say streets are well-lit

  • 88 % Say it's walkable to restaurants

  • 88 % Say it's walkable to grocery stores

  • 85 % Say kids play outside

  • 63 % Say there's holiday spirit

  • 54 % Say neighbors are friendly

  • 49 % Say they plan to stay for at least 5 years

  • 48 % Say it's quiet

  • 46 % Say there's wildlife

  • 45 % Say parking is easy

  • 42 % Say yards are well-kept

  • 40 % Say car is needed

  • 37 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 77 Highland Rd

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Off Market Homes Near 77 Highland Rd

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