$1,750,000
1 Overlook Way
Winchester, MA, 01890
Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room – with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.
Property Details
Price:
$1,750,000
MLS #:
73581571
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
wedgemere
Listed Date:
Sep 23, 2026
Finished Sq Ft:
3,604
Total Sq Ft:
3,604
Lot Size:
15,680 sqft / 0.36 acres (approx)
Year Built:
1941
Schools
Elementary School:
Ambrose
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
3340
Appliances
Gas Water Heater, Range, Dishwasher, Trash Compactor, Microwave, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
264
Cooling
Ductless
Fireplaces Total
3
Flooring
Tile, Hardwood, Engineered Hardwood, Flooring – Wood, Flooring – Wall to Wall Carpet, Laminate
Heating
Central, Baseboard, Natural Gas, Ductless, Fireplace
Interior Features
Closet/Cabinets – Custom Built, Walk-In Closet(s), Cedar Closet(s), Storage, Library, Bonus Room, Play Room, Walk-up Attic
Laundry Features
Gas Dryer Hookup, Washer Hookup, In Basement
Main Level Bathrooms
1
Exterior
Architectural Style
Colonial
Attached Garage YN
1
Community Features
Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Conservation Area, Highway Access, Public School
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Patio, Rain Gutters, Sprinkler System, Screens, Stone Wall
Garage Spaces
2
Lot Features
Corner Lot, Wooded, Level
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Attached, Garage Door Opener, Paved Drive, Off Street, Paved
Parking Spots
6
Parking Total
6
Patio And Porch Features
Patio
Roof
Shingle
Security Features
Security System
Window Features
Skylight, Screens
Financial
Tax Year
2026
Taxes
$17,650
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 Oct 17, 2026
65
Single Family Listed
61
Avg DOM
564
Avg $ / SqFt
$2,108,182
Avg List Price
Community
- Address1 Overlook Way 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
- 1 Overlook Way Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,750,000 and features 4 beds, 3 baths, and has approximately 3,604 square feet of living space, and was originally constructed in 1941. The current price per square foot is $486. The average price per square foot for Single Family listings in Winchester is $564. The average listing price for Single Family in Winchester is $2,108,182. To schedule a showing of MLS#73581571 at 1 Overlook Way in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Better Homes and Gardens Real Estate – The Shanahan Group. 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.
1 Overlook Way
Winchester, MA