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284 Woodland Road Brookline — Photo 1 of 38

284 Woodland Road Brookline — Photo 1 of 38

$3,100,000

Investment Analysis — 284 Woodland Road

Brookline, MA 02467 — Chestnut Hill

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02467 carries an estimated $5,380/mo in gross rent — about a 0.63% cap rate and $19,508/yr in estimated NOI at the $3,100,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

5

Baths

4.5

SqFt

3,913

Style

Single Family

Built

1933

A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.

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 3,913 sq ft principal dwelling). Lot size: 22,499 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.

Open Houses

Property Details

Financials

Original Price$3,100,000
Annual Taxes$29,558

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms11
Fireplaces1
FlooringTile, Pine
BasementFull, Partially Finished

Climate & Utilities

HeatingForced Air, Steam, Oil
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionStone
RoofOther
FoundationBlock
ZoningS15

Property & Lot

Acres0.52
SqFt Lot22,499
Lot Features--

Amenities & Appliances

Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Bike Path

Geography

Floorplan Breakdown

Structural Layout

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

24.583333333 x 14.083333333

Flooring - Wood, French Doors, Exterior Access

Dining Room
Lvl First

12.5 x 14.5

Closet/Cabinets - Custom Built, Flooring - Wood

Kitchen
Lvl First

23.166666666 x 19.583333333

Flooring - Wood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Exterior Access, Remodeled

Family Room
Lvl First

16.916666666 x 21.166666666

Closet/Cabinets - Custom Built, Flooring - Wood

Master Bedroom
Lvl Second

17.833333333 x 19.166666666

Bathroom - Full, Vaulted Ceiling(s)

Bedroom 2
Lvl Second

16.333333333 x 14

Bedroom 3
Lvl Second

10 x 12.416666666

Closet

Bedroom 4
Lvl Second

10.416666666 x 12.916666666

Closet

Bedroom 5
Lvl Second

12.583333333 x 14.916666666

Closet

Bathroom 1
Lvl First

Bathroom - Half

Bathroom 2
Lvl Second

Bathroom - Full, Bathroom - Tiled With Tub & Shower

Bathroom 3
Lvl Second

Bathroom - Full, Bathroom - Tiled With Tub & Shower

Listing Provided By

Listing Agent: The Denman Group

Listing Office: eXp Realty LLC

MLS® Number: 73573502