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!
This home has been viewed 15 times
Last Checked: June 28th, 2026 at 4:29am (Source: MLS PIN #73482952)
Garage Parking
Green Features
Air Conditioning
Waterview
Waterfront
Lead Paint Free
General Information for 4 Dartmouth St, Winchester MA 01890
Listing ID73482952
Property TypeSingle Family / Detached
Price$4,449,000 ($681.73/SqFt)
StyleColonial
CityWinchester
CountyMiddlesex
Neighborhood(s)
Garage Parking2
ZoningRDB
Year Built1935
Year Built SourcePublic Records
Year Built DetailsActual
Interior Features for 4 Dartmouth St, Winchester MA 01890
Approximate Living Area Total6526
Living Area Includes BasementYes
Rooms15
Bedrooms5
Primary En Suite BathroomYes
BasementFull
Cooling1, Split
Fireplaces
AppliancesRange
FlooringTile
Electric
Exterior Features for 4 Dartmouth St, Winchester MA 01890
Approximate Lot Size (Acres)0.67
Approximate Lot Size (Square Feet)29002
Total Parking8 (2 Garage)
Garage Parking2
WaterPublic
SewerPublic Sewer
Lot Features
Parking Features1
Exterior FeaturesPorch
Foundation Materials
Construction Materials
Road Frontage Type
Patio & PorchCovered
Roof MaterialAsphalt/fiberglass Shingles
Utility Connections110 Volts
Water ViewsYes
Water Views FeaturesBay
Waterfront1
Waterfront FeaturesRiver
Pool Features
Horse Permitted0
Horse AmenitiesRiver
Disclosures for 4 Dartmouth St, Winchester MA 01890
Lead PaintNone
UFFI
Living Area Includes BasementYes
Living Area Disclosure
Building Area SourcePublic Records
Special Listing Conditions
ExclusionsSome Of The Sellers' Personal Items Are Not Included In The Sale.
Compensation Based On
Financial Information for 4 Dartmouth St, Winchester MA 01890
Association Fee
Association Fee Frequency
Association Fee Includes
Real Estate Tax51006.78
Tax Year2026
Assessed Value$4,603,500
Location Information for 4 Dartmouth St, Winchester MA 01890
Elementary SchoolVo
Middle SchoolMccall
High SchoolWhs
Neighborhood(s)
Area AmenitiesWalk/jog Trails
Contact Information for 4 Dartmouth St, Winchester MA 01890