Active
122 Days on market
68 Dudley Street Brookline — Photo 1 of 29

68 Dudley Street Brookline — Photo 1 of 29

Recent Drop: $1,155,000

$4,650,000
$3,495,000

$3,495,000

68 Dudley Street, Brookline, MA 02445

Brookline, MA 02445 — Reservoir

Beds

5

Baths

4.5

SqFt

5,234

Style

Single Family

Built

1930

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$668/sqft
Local Avg (Brookline)$826/sqft
19% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Brookline, MA.

Property Details

Financials

Original Price$4,650,000
Annual Taxes$42,942.95

Parking

Garage2
Off-Street10

Interior Specifications

Total Rooms11
Fireplaces4
FlooringTile, Carpet, Hardwood, Flooring - Hardwood
BasementFull, Partially Finished, Walk-Out Access, Interior Entry, Concrete

Climate & Utilities

HeatingForced Air, Heat Pump, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationStone
ZoningRes

Property & Lot

Acres0.46
SqFt Lot19,940
Lot FeaturesEasements

Amenities & Appliances

Gas Water Heater • Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Washer • Dryer • Wine Refrigerator

Neighborhood

Park • Walk/Jog Trails • Golf • Medical Facility • Bike Path • Conservation Area

Geography

Floorplan Breakdown

Structural Layout

Third
Bedroom 4Bedroom 5
Second
Master BedroomBedroom 2Bedroom 3Bathroom 3
First
Living RoomDining RoomKitchenFamily RoomBathroom 1
Basement
Bathroom 2
Living Room
Lvl First

Flooring - Hardwood, French Doors

Dining Room
Lvl First

Flooring - Hardwood, Window(s) - Picture

Kitchen
Lvl First

Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid

Family Room
Lvl First

Ceiling Fan(s), Flooring - Hardwood

Master Bedroom
Lvl Second

Flooring - Wall to Wall Carpet

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Flooring - Wall to Wall Carpet

Bedroom 4
Lvl Third

Flooring - Wall to Wall Carpet

Bedroom 5
Lvl Third

Flooring - Wall to Wall Carpet

Bathroom 1
Lvl First

Bathroom - Half

Bathroom 2
Lvl Basement

Bathroom - Full

Bathroom 3
Lvl Second

Property History

Price Drop
$3,495,000

Was $3,995,000

Sep 9, 2026

MLS® 73517349

Price Drop
$3,995,000

Was $4,650,000

Jun 18, 2026

MLS® 73517349

Listed
$4,650,000

May 12, 2026

MLS® 73517349

Population

22,560

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$140K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

47.9%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Norfolk County

1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 5,234 sq ft principal dwelling). Lot size: 19,940 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Friedler & Marchant Living Group

Listing Office: Hammond Residential Real Estate

MLS® Number: 73517349

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