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.
Request a professional market analysisPhoto-based condition insights
Overall presentation: excellent
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About 4 Dartmouth
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Request a tour of 4 Dartmouth and a Bean Group agent will help coordinate an available time with the listing side.
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Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
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