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Bean Group
Offered at $4,299,000Active
beds
5
baths
6
sq ft
6,526
Built
1935

4 Dartmouth

Winchester, MA 01890

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!

Listing last checked: Listing updated:

Listed by The Pallotta Group · Gibson Sotheby's International Realty · MLS #73574948

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Details at a glance

Interior6 property facts
Rooms
15
Heating
Forced Air, Steam, Natural Gas, Hydronic Floor Heat(Radiant)
Cooling
Central Air
Flooring
Wood, Flooring - Vinyl, Laminate, Flooring - Stone/Ceramic Tile
Basement
Yes · Full, Finished
Fireplaces
3
Building6 property facts
Style
Single Family Residence
Year built
1935
Garage
2
Parking
8
Foundation
Concrete Perimeter, Stone, Brick/Mortar
Roof
Slate
Land & utilities6 property facts
Lot size
0.67 acres
Water
Public
Sewer
Public Sewer
Waterfront
Y
Pool
Not reported
Zoning
RDB
Financial2 property facts
Annual taxes
$51,007
Assessment year
2026

Location

Estimated monthly cost

Explore costs at the $4,299,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$25,989 / monthAdjust
Principal & interest
$21,738
Property tax
$4,251
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $51,007. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

More property insights

Automated value estimate $4,403,599

Estimated range $3,907,682–$4,899,516.

Automated estimates are not appraisals or guarantees of market value.

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Photo-based condition insights

Overall presentation: excellent

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About 4 Dartmouth

Can I request a private showing?

Request a tour of 4 Dartmouth and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.