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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 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 kitchen, family room and study, while several curated outdoor dining and gathering areas invite entertaining overlooking the pond. The expansive living and dining rooms complete the first floor. A generous primary suite is a private retreat with a spacious bath and ample closets. 4 other ample bedrooms 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. Kayak, skate, go fishing and enjoy life on the water!
More Info
Basic Information
- Bedrooms5
- Mls StatusActive
- Bathroom6
- Parcel Number M:019 B:0062 L:0,899730
Tax Information
- Tax Assessed Value $4,603,500
- Tax Year 2026
- Taxes$51,006
School Information
- High School Winchester
- Elementary SchoolVo
- High SchoolWinchester
- Junior HighMccall
Parking
- Parking Spaces6
- Covered Spaces 2
- Garage YN Yes
- Open Parking YN Yes
- Parking Features Attached, Paved Drive, Off Street
Rooms
- Bathroom 1 Second,13 x 10
- Bathroom 2 Second,8 x 9
- Bathroom 3 Second,8 x 9
- Bathrooms Total Decimal 5.5
- Bedroom 2 Second,20 x 14
- Bedroom 3 Second,15 x 20
- Bedroom 4 Second,19 x 21
- Bedroom 5 Second,16 x 17
- Dining Room First,14 x 19
- Family Room First,19 x 20
- Full Bath5
- Half Baths1
- Kitchen First,15 x 36
- Living Room First,28 x 19
- Master Bedroom Second,23
- Office First,14 x 12
Basic Information
- List Price$4,449,000
- MLS Number73482952
- Modification Date05/19/2026
- Property SubTypeSingle Family Residence
Location
- Address4 Dartmouth Street
- Building Number4
- CountyMiddlesex
- StateMA
- StreetDartmouth Street
- TownWinchester
- Zip01890
Building
- Attached Garage YN Yes
- BasementFull, Finished
- Building Area Units Square Feet
- FireplaceYes
- Fireplace Features Family Room, Living Room
- Fireplaces Total 3
- FoundationConcrete Perimeter, Stone, Brick/Mortar
- Garage Spaces2
- Patio And Porch Features Porch, Deck, Patio
- Property StyleTudor
- Rooms15
- Utilities For Gas Range
- Window Features Storm Window(s)
- Year Built1935
- Year Built Details Actual
- Year Built Source Public Records
Property
- Acreage0.67
Interior
- Flooring Wood, Flooring - Stone/Ceramic Tile, Flooring - Vinyl, Laminate
- Interior Features
- Exercise Room
- Game Room
- Media Room
- Mud Room
- Office
- Walk-up Attic
- Wet Bar
- Wine Cellar
- Wired for Sound
Exterior
- Exterior Features
- Deck
- Decorative Lighting
- Patio
- Porch
- Professional Landscaping
- Rain Gutters
- Sprinkler System
- RoofSlate
Utilities
- Cooling Central Air
- Cooling YN Yes
- Heat SystemYes
- Heating Forced Air, Steam, Natural Gas, Hydronic Floor Heat(Radiant)
- Sewer Public Sewer
- Water Source Public
Property Information
- Square Feet6,526
- Building Area Source Public Records
- Living Area 6,526
- Lot Size Square Feet 29,002
- Lot Size Units Acres
- View YN Yes
Amenities
- Amenities
- Bike Path
- Conservation Area
- House of Worship
- Medical Facility
- Park
- Private School
- Public School
- Public Transportation
- Shopping
- Walk/Jog Trails
- Appliances IncludedRange, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
- Green Energy Efficient Thermostat
- Security Features Security System
Water Body
- WaterfrontYes
- Waterfront Features Waterfront, Pond
Legal
- ZoningRDB
Other
- Date Listed03/05/2026
- Farm Land Area Units Square Feet
- View Count4
Map Location
Listed by The Pallotta Group of Gibson Sotheby's International Realty
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