284 Woodland Road

Taxes: $29,558 (2026)

About this home

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.

Property details

Sewer

Private

Style

Cape

Water

City/Town Water

Cooling

Central Air

Heating

Forced Air, Heat Pump, Individual

Type

Detached

Flooring

Tile, Pine

Road type

Paved

Appliances

Range, Dishwasher, Disposal, Microwave, Countertop Range, Refrigerator, Freezer, Washer, Dryer

Master Bath

Yes

Construction

Stone/Concrete

Roof

Other (See Remarks)

Garage

Garage Door Opener

Lot

Paved Drive, Fenced/Enclosed

Parking

1-10 Spaces, Paved Driveway

Basement

Full, Partially Finished

Electric

200 Amps

Exterior

Deck, Patio, Pool - Inground, Storage Shed, Sprinkler System

Interior

Security System