4 Dartmouth St
Winchester, MA, 01890
$4,699,000
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!
Current real estate data for Single Family in Winchester as of Mar 09, 2026
40
Single Family Listed
65
Avg DOM
532
Avg $ / SqFt
$2,186,463
Avg List Price
Property Details
Price:
$4,699,000
MLS #:
73482952
Status:
Active
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Mar 5, 2026
Finished Sq Ft:
6,526
Total Sq Ft:
6,526
Lot Size:
29,002 sqft / 0.67 acres (approx)
Year Built:
1935
Schools
Elementary School:
Vo
Middle School:
Mccall
High School:
Whs
Interior
Appliances
Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood, Flooring – Stone/Ceramic Tile, Flooring – Vinyl, Laminate
Heating
Forced Air, Steam, Natural Gas, Hydronic Floor Heat(Radiant)
Laundry Features
Second Floor
Exterior
Architectural Style
Tudor
Community Features
Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, House of Worship, Private School, Public School
Exterior Features
Porch, Deck, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting
Parking Features
Attached, Paved Drive, Off Street
Parking Spots
6
Roof
Slate
Security Features
Security System
Financial
Tax Year
2026
Taxes
$51,007
Map
Contact Us
Mortgage Calculator
Community
- Address4 Dartmouth St Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- 4 Dartmouth St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $4,699,000 and features 5 beds, 6 baths, and has approximately 6,526 square feet of living space, and was originally constructed in 1935. The current price per square foot is $720. The average price per square foot for Single Family listings in Winchester is $532. The average listing price for Single Family in Winchester is $2,186,463. To schedule a showing of MLS#73482952 at 4 Dartmouth St in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
Similar Listings Nearby
CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy of Leading Edge Real Estate. 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.
4 Dartmouth St
Winchester, MA












































