4 Dartmouth

Taxes: $51,006.78 (2026)

About this home

Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

Property details

Sewer

Private

Style

Houseboat

Water

City/Town Water

Cooling

Central Air

Heating

Forced Air, Heat Pump, Hot Air Gravity, Steam

Type

Detached

Flooring

Wood

Road type

Public

Appliances

Range, Wall Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Refrigerator - Wine Storage

Waterfront

Pond

Master Bath

Yes

Construction

Brick

Roof

Shingle

Garage

Attached

Lot

Paved Drive, Scenic View(s)

Parking

1-10 Spaces

Basement

Full, Finished

Exterior

Porch, Deck, Patio, Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting

Interior

Security System, Wetbar, Walk-up Attic, Wired for Surround Sound

Waterview Features

Pond