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68 Dudley Street Brookline MA 02445

Active

$4,650,000

5,234 Square Feet

5 Bedrooms

4 Bathrooms

1 Half Bathrooms

10 Parking

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.

Property Details for 68 Dudley Street

Total Rooms: 11

Bedrooms: 5

Bathrooms: 4Full 1Half

Living Area: 5,234

Lot Size (Acres/SF): 0.46/ 19,940

Lot Features:

Levels:

Total Parking Spaces: 10

Garage Spaces: 2

Parking Features: Detached, Paved Drive, Shared Driveway, Off Street

Listing ID: 73517349

Postal Code: 02445

Neighborhood: Chestnut Hill

Elementary School District: Roland Hayes

Elementary School Buffer Zone: Hayes/Lincoln

High School: Brookline High School

Year Built: 1930

Architectural Style:

Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete

Features for 68 Dudley Street

Heating: Forced Air, Heat Pump, Natural Gas

Heating Zones:

Fireplaces: 4

Accessibility Features:

Association: False

Association Fee:

Fee Frequency:

Association Fee Includes:

Association Amenities:

Management Type:

Optional Fee:

Optional Fee Includes:

Elevator: False

Cooling: Central Air

Cooling Zones:

Private Pool: True

Pool Features:

Waterfront: False

Waterfront Features:

Pets Allowed:

Entry Level (Floor):

Entry Location:

Complex Complete: False

Total Units in Building:

Owner Occupied Units:

Utilities & Financials for 68 Dudley Street

Electric:

Water Source: Public

Sewer: Public Sewer

Utility Connections:

Annual Tax: $42,943

Assessed Value: $4,507,500

Tax Year: 2026

Disclosures for 68 Dudley Street

Disclosures: Seller makes no representations about speaker system, fireplaces, basement electric heat. One window in Primary covered by built-in.. Range vent not operational

Exclusions:

Property Attached: False

Historic District:

Zoning Code: S-15

Zoning Description: SINGLE-FAMILY

Zoning Category: single_family

Zoning FAR:

Zoning Min Lot: 15,000

Lead Paint: Unknown

SqFt Includes Basement: False

Square Feet Disclosures:

Voting Precinct: 14 Located at Heath School Gymnasium, 100 Eliot Street

Listing Lifecycle for 68 Dudley Street

List Date: 2026-05-12

Off Market Date:

Under Agreement Date:

Sold Date:

List Office: Hammond Residential Real Estate

Listing Agent: Friedler / Marchant Living Group

Original List Price: $4,650,000

Sold Price: ()

Square Feet Disclosures:

Last Updated on: 2026-05-26 00:00:07 from: mls-pin

Buyer’s Office:

Buyer’s Agent: