Primary bedroom
- Level
- Second
- Area
- 247 sqft
- Length
- 19 ft
- Width
- 13 ft
- Features
- Bathroom - Full · Bathroom - Double Vanity/Sink · Ceiling Fan(s) · Flooring - Hardwood · Double Vanity · Closet - Double
1 Overlook Way · Winchester
For sale
FOR SALE · MLS #73581571
$1,750,000
- beds
- 4
- baths
- 2.5
- sqft
- 3,604
1 Overlook Way
Winchester, MA 01890
LOCATION
Property location
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1 Overlook Way, Winchester, MA 01890Open Street View
High Street to Overlook Way
- Home type
- Single Family Residence
- Interior living area
- 3,604 sqft
- Year built
- 1941
- Lot size
- 15,680 sqft (about 0.36 acres)
- Parking spaces
- 6
- Price per sqft
- $486/sqft
About this home
NEW Photos! Welcome to One Overlook Way in Winchester. This home is located on a 1/3 acre corner lot on a short cul-de-sac off High Street- a premier location close to Ambrose Elementary School and the Winchester Country Club. Don't miss this spacious 4+ bedroom center-entrance Colonial. with a thoughtfully designed circular 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 with room to add an island or large table also opens naturally into the comfortable family room - with gas fireplace, custom built-ins, a new split AC and access to the back and side yard! 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 split AC, 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 second home office, hangout zone or storage. The finished lower level adds another playroom, 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 storage 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.
Listed by Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
MLS PIN #73581571 · Updated 10/30/2026, 1:40:00 PM ET
Facts & features
Home overview
- Property subtype
- Single Family Residence
- Property category
- Residential
- MLS status
- Active
- Bedrooms
- 4
- Full bathrooms
- 2
- Half bathrooms
- 1
- Total bathrooms
- 2.5
- Total rooms
- 11
- Living area
- 3,604 sqft
- Living area source
- Measured
- Above grade finished area
- 3,340 sqft
- Below grade finished area
- 264 sqft
- Building area
- 3,604
- Building area units
- Square Feet
- Building area source
- Measured
- Area includes basement
- Yes
- Area disclosures
- Measured for marketing purposes. Buyer/Buyer Agent to do due diligence. Some images are AI generated
- Main level bathrooms
- 1
Interior & systems
- Heating
- Central · Baseboard · Natural Gas · Ductless · Fireplace
- Heating available
- Yes
- Heating zones
- 5
- Cooling
- Ductless
- Cooling available
- Yes
- Cooling zones
- 2
- Appliances
- Gas Water Heater · Range · Dishwasher · Trash Compactor · Microwave · Refrigerator · Washer · Dryer
- Flooring
- Tile · Hardwood · Engineered Hardwood · Flooring - Wood · Flooring - Wall to Wall Carpet · Laminate
- Interior features
- Closet/Cabinets - Custom Built · Walk-In Closet(s) · Cedar Closet(s) · Storage · Library · Bonus Room · Play Room · Walk-up Attic
- Laundry
- Gas Dryer Hookup · Washer Hookup · In Basement
- Basement
- Full · Partially Finished · Interior Entry · Bulkhead · Sump Pump · Concrete
- Fireplace
- Yes
- Fireplaces
- 3
- Fireplace features
- Family Room · Living Room
- Electrical service
- Circuit Breakers
- Security features
- Security System
- Windows
- Skylight · Screens
- Primary bathroom features
- Yes
Room details
Bedroom 2
- Level
- Second
- Area
- 208 sqft
- Length
- 16 ft
- Width
- 13 ft
- Features
- Flooring - Hardwood · Closet - Double
Bedroom 3
- Level
- Second
- Area
- 228 sqft
- Length
- 19 ft
- Width
- 12 ft
- Features
- Flooring - Hardwood · Attic Access · Closet - Double
Bedroom 4
- Level
- Second
- Area
- 144 sqft
- Length
- 12 ft
- Width
- 12 ft
- Features
- Closet · Flooring - Hardwood
Living room
- Level
- Main,First
- Area
- 234 sqft
- Length
- 18 ft
- Width
- 13 ft
- Features
- Flooring - Hardwood · Window(s) - Bay/Bow/Box
Dining room
- Level
- Main,First
- Area
- 156 sqft
- Length
- 13 ft
- Width
- 12 ft
- Features
- Closet/Cabinets - Custom Built · Flooring - Hardwood · Chair Rail
Family room
- Level
- First
- Area
- 300 sqft
- Length
- 20 ft
- Width
- 15 ft
- Features
- Closet · Closet/Cabinets - Custom Built · Flooring - Wood · Exterior Access · Open Floorplan · Recessed Lighting · Slider
Kitchen
- Level
- Main,First
- Area
- 221 sqft
- Length
- 17 ft
- Width
- 13 ft
- Features
- Flooring - Stone/Ceramic Tile · Window(s) - Bay/Bow/Box · Dining Area · Countertops - Stone/Granite/Solid · Open Floorplan · Recessed Lighting · Stainless Steel Appliances
Bathroom 1
- Level
- Main,First
- Area
- 24 sqft
- Length
- 6 ft
- Width
- 4 ft
- Features
- Bathroom - Half · Flooring - Stone/Ceramic Tile
Bathroom 2
- Level
- Second
- Area
- 65 sqft
- Length
- 13 ft
- Width
- 5 ft
- Features
- Bathroom - Full · Bathroom - Tiled With Tub & Shower · Flooring - Stone/Ceramic Tile
Bathroom 3
- Level
- Second
- Area
- 45 sqft
- Length
- 9 ft
- Width
- 5 ft
- Features
- Bathroom - Full · Bathroom - Tiled With Tub & Shower
Construction & condition
- Year built
- 1941
- Year built source
- Public Records
- Year built details
- Actual
- Architectural style
- Colonial
- Construction materials
- Frame
- Foundation
- Concrete Perimeter
- Roof
- Shingle
- Attached property
- No
- Home warranty
- No
- Exterior color
- Beige
- Accessory dwelling unit
- N
- Year round use
- Yes
Garage & parking
- Total parking spaces
- 6
- Parking features
- Attached · Garage Door Opener · Paved Drive · Off Street · Paved
- Garage
- Yes
- Garage spaces
- 2
- Attached garage
- Yes
- Covered spaces
- 2
- Carport
- No
- Open parking
- Yes
- Open parking spaces
- 4
Lot & outdoor features
- Lot area
- 15,680 sqft (about 0.36 acres)
- Lot size
- 0.36 acres
- Reported lot area
- 0.36
- Lot size units
- Acres
- Lot features
- Corner Lot · Wooded · Level
- Exterior features
- Patio · Rain Gutters · Sprinkler System · Screens · Stone Wall
- Patio & porch
- Patio
- Spa
- No
- Waterfront
- No
- Beachfront
- No
- Water views
- No
Utilities & infrastructure
- Water source
- Public
- Sewer
- Public Sewer
- Road frontage
- Public · Dead End
- Road surface
- Paved
- Road responsibility
- Public Maintained Road
HOA & community
- Homeowners association
- No
- Community features
- Public Transportation · Shopping · Park · Walk/Jog Trails · Golf · Conservation Area · Highway Access · Public School
- Senior community
- No
Taxes & property records
- Annual property tax
- $17,650
- Tax year
- 2026
- Assessed value
- $1,593,000
- Parcel number
- 20 152 0,900071
- Zoning
- RDA
- Registry book
- 1435
- Registry page
- 85
- Tax map
- 20
- Tax block
- 152
- Tax lot
- 0
Location & listed schools
- City
- Winchester
- County
- Middlesex
- State
- MA
- ZIP code
- 01890
- MLS area
- Wedgemere
- Listed elementary school
- Ambrose
- Listed middle school
- Mccall
- Listed high school
- Whs
- Directions
- High Street to Overlook Way
Listing & disclosures
- MLS number
- 73581571
- Listing date
- 2026-09-23
- Original entry date
- 2026-09-23
- Status changed
- 2026-10-13
- Listing modified
- 2026-10-30
- Original list price
- $1,850,000
- Current list price
- $1,750,000
- List price per sqft
- $485.57
- Days on market
- 37
- Property market time
- 37
- Listing terms
- Contract
- Disclosures
- Driveway located on High Street. Sump in basement. Rear door in garage has broken lock.
- Disclosure indicator
- Y
- Lead paint
- Unknown
Price & tax details
Current asking price$1,750,000
Original asking price$1,850,000
Listed on2026-09-23
Days on market37
| Year | Property tax | Assessed value |
|---|---|---|
| 2026 | $17,650 | $1,593,000 |
These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.
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SCHOOLS & EDUCATION
Schools & performance
School names, grades and state-reported measures are listed below.
Schools named in the listing
96DESE percentile
95DESE percentile
—DESE percentile
MLS-listed high school
Whs
School name supplied by the listing; confirm with the district.
MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.
What do these numbers mean?
DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.
School names link to available school or district websites.
Information is deemed reliable but is not guaranteed. © 2026 MLS Property Information Network, Inc. All rights reserved.
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