$4,449,000
4 Dartmouth St
Winchester, MA, 01890
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!
Property Details
Price:
$4,449,000
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
Above Grade Finished Area
4795
Appliances
Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1731
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)
Interior Features
Office, Exercise Room, Media Room, Game Room, Wine Cellar, Mud Room, Wet Bar, Walk-up Attic, Wired for Sound
Laundry Features
Second Floor
Exterior
Architectural Style
Tudor
Attached Garage YN
1
Community Features
Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, House of Worship, Private School, Public School
Covered Spaces
2
Exterior Features
Porch, Deck, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting
Garage Spaces
2
Green Energy Efficient
Thermostat
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Attached, Paved Drive, Off Street
Parking Spots
6
Parking Total
6
Patio And Porch Features
Porch, Deck, Patio
Roof
Slate
Security Features
Security System
View
Scenic View(s)
Waterfront Features
Waterfront, Pond
Window Features
Storm Window(s)
Financial
Tax Year
2026
Taxes
$51,007
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of May 04, 2026
71
Single Family Listed
48
Avg DOM
548
Avg $ / SqFt
$2,185,977
Avg List Price
Community
- Address4 Dartmouth St Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 4 Dartmouth St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $4,449,000 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 $682. The average price per square foot for Single Family listings in Winchester is $548. The average listing price for Single Family in Winchester is $2,185,977. To schedule a showing of MLS#73482952 at 4 Dartmouth St in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy 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