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Properties

  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
  • 4 Dartmouth St, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 15 Rooms Rooms,5.5 BathroomsBathrooms,Residential,For Sale,Dartmouth St,73482952
Property Description

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!

Features
Heating System:
Forced Air, Steam, Hydronic Floor Heat(radiant), Natural Gas
Cooling System:
Central Air
Basement:
Full, Finished
Fireplace:
Family Room, Living Room
Security:
Security System
Parking:
Attached, Off Street, Paved Drive
Appliances:
Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Freezer, Oven, Wine Refrigerator
Exterior Unit Features:
Professional Landscaping, Deck, Patio, Porch, Decorative Lighting, Sprinkler System, Rain Gutters
Flooring:
Wood, Laminate, Flooring - Stone/ceramic Tile, Flooring - Vinyl
Sewer:
Public Sewer
Style:
Tudor
Water:
Public
Disclosure:
Some photos have been virtually staged. Buyers and agents must verify all information and perform their own due diligence., no dogs or undergrad students. Cat pet rent of $50/month per cat., Original Peerless cast iron boiler serviced yearly
Garage Parking:
2
Interior Features:
Walk-up Attic, Wet Bar, Exercise Room, Media Room, Game Room, Wired For Sound, Office, Mud Room, Wine Cellar
Lead Paint:
Unknown
Waterview Features:
Pond
Laundry Features:
Second Floor
Additional Information
Grade School:
Vo
High School:
Whs
Middle School:
Mccall
Parking Spaces:
6
Tax Year:
2026
Status:
Active
Price Per Sqft:
$720
Zoning:
RDB
Orig Price:
$4,699,000
Fireplaces:
3
Waterfront:
Yes
MlsStatus:
New
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 50' 39.8''
Latitude:
N42° 27' 17.8''
  • Google Map

Residential

4 Dartmouth St, Winchester, Massachusetts

5 Bedrooms
5.5 Total Bathrooms
6,526 Sqft
$4,699,000
Listing ID #73482952
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$4,699,000
View :
Scenic View(s)
Bedrooms :
5
Rooms :
15
Total Bathrooms :
5.5
Full Bathrooms :
5
Half Bathrooms :
1
Square Footage :
6,526 Sqft
Year Built :
1935
Lot Area :
0.67 Acre
Listing ID :
73482952
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

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