MLS #73482952 image #0
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
TudorWaterfrontVoMccallWhsScenic View(s)

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

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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.

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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 James
4 Dartmouth St
Winchester, MA