68 Dudley Street, Brookline MA 02445
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$3,995,000

68 Dudley Street, Brookline MA 02445
Brookline, MA 02445
Listed by Friedler / Marchant Living Group
Bedrooms
5
Bathrooms
4.1
Living area
5,234 sqft
Year built
1930

About this home

Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and serene water views on nearly a half-acre with bluestone patio and pool. The gracious entry opens into a grand foyer flanked by sun-drenched rooms. Bay windows in the living room, dining room, family room, and primary suite frame reservoir and garden views. Four fireplaces, high ceilings, crown molding, and custom woodwork throughout. Well-equipped kitchen for serious cooks with breakfast area and counter seating. Private first-floor study. Enchanting screened porch access the dining and living rooms for al fresco dining. Second floor: three bedrooms, two baths, and a primary suite with large dressing room, ensuite bath, and private deck. Third floor: two additional bedrooms and full bath. Lower level: exercise room, sauna, wine cellar and lav. Two-car garage. Minutes from Chestnut Hill shopping, Longwood Medical Area, and universities.

Highlights

ViewPrivate poolFireplace

Property details

MLS #
73517349
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
100
On market date
May 12, 2026
Stories
N/A
Garage spaces
2
Lot size
0.46 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
William H Lincoln
0.37 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
471
Student:teacher ratio
9.8:1
District
Brookline
Middle
James P Timilty Middle
2.29 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
205
Student:teacher ratio
8.2:1
District
Boston
High
Brookline High
0.6 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,087
Student:teacher ratio
10.9:1
District
Brookline

Mortgage calculator

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Est. monthly payment
$24,208/mo
$799,000 down
$3,196,000 loan
Principal & interest$20,729
Property tax (est.)$3,329
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 21, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.