
68 Dudley Street Brookline — Photo 1 of 29
Recent Drop: $1,155,000
$3,495,000
Investment Analysis — 68 Dudley Street
Brookline, MA 02445 — Reservoir
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02445 carries an estimated $5,240/mo in gross rent — about a 0.14% cap rate and $4,846/yr in estimated NOI at the $3,495,000 list price. Adjust every assumption in the calculator below.
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 seasonal 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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl FirstFlooring - Hardwood, French Doors
Dining Room
Lvl FirstFlooring - Hardwood, Window(s) - Picture
Kitchen
Lvl FirstFlooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid
Family Room
Lvl FirstCeiling Fan(s), Flooring - Hardwood
Master Bedroom
Lvl SecondFlooring - Wall to Wall Carpet
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondFlooring - Wall to Wall Carpet
Bedroom 4
Lvl ThirdFlooring - Wall to Wall Carpet
Bedroom 5
Lvl ThirdFlooring - Wall to Wall Carpet
Bathroom 1
Lvl FirstBathroom - Half
Bathroom 2
Lvl BasementBathroom - Full
Bathroom 3
Lvl SecondProperty History
$3,495,000
Was $3,995,000
Sep 9, 2026
MLS® 73517349
$3,995,000
Was $4,650,000
Jun 18, 2026
MLS® 73517349
$4,650,000
May 12, 2026
MLS® 73517349
Listing Agent: Friedler & Marchant Living Group
Listing Office: Hammond Residential Real Estate
MLS® Number: 73517349



