Dimensions16 x 13
FeaturesFlooring - Hardwood, Closet - Double
LevelSecond
1 Overlook Way, Winchester MA 01890
Winchester, MA 01890 • Wedgemere
$1,850,000
Est. $11,025/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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Open House Schedule
27
Sep
Sunday, September 27
12:00 PM - 1:30 PM EDT
26
Sep
Saturday, September 26
11:00 AM - 12:30 PM EDT
25
Sep
Friday, September 25
12:00 PM - 1:30 PM EDT
24
Sep
Thursday, September 24
5:00 PM - 6:30 PM EDT
About this home
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.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Sep 23, 2026
$1,850,000
Original listing
Agent: Lynne Russo
Office: Better Homes and Gardens Real Estate - The Shanahan Group
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/23/2026 | 🏠 Listed for Sale | $1,850,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $17,650 | $1,593,000 |
Financial Details
Annual Property Tax
$17,650
Tax Year 2026
Assessed Value
$1,593,000
Facts & Features
2 Car Garage
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1941
Living Area
3,092 sq ft
Lot Size
0.36 acres
Bedrooms
4
Full Baths
2
Half Baths
1
Total Rooms
11
Interior
Heating
Central, Baseboard, Natural Gas, Electric, Ductless, Fireplace
Cooling
Ductless
Flooring
Tile, Hardwood, Engineered Hardwood, Flooring - Wood, Flooring - Wall To Wall Carpet, Laminate
Appliances
Gas Water Heater, Range, Dishwasher, Trash Compactor, Microwave, Refrigerator, Washer, Dryer
Fireplace
Family Room, Living Room
Fireplaces
3
Basement
Full, Partially Finished, Interior Entry, Bulkhead, Sump Pump, Concrete
Laundry
Gas Dryer Hookup, Washer Hookup, In Basement
Features
Closet/cabinets - Custom Built, Walk-in Closet(s), Cedar Closet(s), Storage, Library, Bonus Room, Play Room, Walk-up Attic
Exterior
Construction
Frame
Architecture
Colonial
Roof
Shingle
Features
Patio, Rain Gutters, Sprinkler System, Screens, Stone Wall
Pool
None
Spa
None
Fencing
None
Patio/Porch
Patio
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Garage Door Opener, Paved Drive, Off Street, Paved
Total Spaces
6
Utilities
Electric
Circuit Breakers
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$17,650
Assessed Value
$1,593,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Driveway Located On High Street. Sump In Basement.
Additional Details
Possession
None
Accepted Financing
Contract
Structure Type
[]
House Color
Beige
Sq Ft Source
Measured
Sq Ft Disclosures
Measured for marketing purposes. Finished third floor square footage is not included.
Documents
None
County
Middlesex
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1941
Bedrooms
4
Full Bathrooms
2
Half Bathrooms
1
Living Area
3,092 sq ft
Total Rooms
11
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,828 sq ft above grade
264 sq ft below grade
Dimensions19 x 12
FeaturesFlooring - Hardwood, Attic Access, Closet - Double
LevelSecond
Dimensions12 x 12
FeaturesCloset, Flooring - Hardwood
LevelSecond
Dimensions13 x 5
FeaturesBathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile
LevelSecond
Dimensions9 x 5
FeaturesBathroom - Full, Bathroom - Tiled With Tub & Shower
LevelSecond
Dimensions19 x 13
FeaturesBathroom - Full, Bathroom - Double Vanity/Sink, Ceiling Fan(s), Flooring - Hardwood, Double Vanity, Closet - Double
LevelSecond
Dimensions17 x 13
FeaturesFlooring - Stone/Ceramic Tile, Window(s) - Bay/Bow/Box, Dining Area, Countertops - Stone/Granite/Solid, Open Floorplan, Recessed Lighting, Stainless Steel Appliances
LevelMain,First
Dimensions6 x 4
FeaturesBathroom - Half, Flooring - Stone/Ceramic Tile
LevelMain,First
Dimensions13 x 12
FeaturesCloset/Cabinets - Custom Built, Flooring - Hardwood, Chair Rail
LevelMain,First
Dimensions20 x 15
FeaturesCloset, Closet/Cabinets - Custom Built, Flooring - Wood, Exterior Access, Open Floorplan, Recessed Lighting, Slider
LevelFirst
Dimensions18 x 13
FeaturesFlooring - Hardwood, Window(s) - Bay/Bow/Box
LevelMain,First
FeaturesYes
Display Options
Outdoor Areas
Patio & porchPatio
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Tile, Hardwood, Engineered Hardwood, Flooring - Wood, Flooring - Wall to Wall Carpet, Laminate
Appliances:
Gas Water Heater, Range, Dishwasher, Trash Compactor, Microwave, Refrigerator, Washer, Dryer
Interior Features:
Closet/Cabinets - Custom Built, Walk-In Closet(s), Cedar Closet(s), Storage, Library, Bonus Room, Play Room, Walk-up Attic
Windows:
Skylight, Screens
Basement:
Full, Partially Finished, Interior Entry, Bulkhead, Sump Pump, Concrete
Laundry:
Gas Dryer Hookup, Washer Hookup, In Basement
Security:
Security System
Construction & Materials
Style:
Colonial
Year Built:
1941
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Central, Baseboard, Natural Gas, Electric, Ductless, Fireplace
Heating Zones:
5
Cooling:
Ductless
Cooling Zones:
2
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio, Rain Gutters, Sprinkler System, Screens, Stone Wall
Patio & Porch:
Patio
Fencing:
Other Structures:
Lot Features:
Corner Lot, Wooded, Level
Road Frontage:
127.00 ft
Road Surface:
Paved
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
6
Parking Features:
Attached, Garage Door Opener, Paved Drive, Off Street, Paved
Special Features
Fireplaces:
3
Fireplace Type:
Family Room, Living Room
Community Amenities:
Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Conservation Area, Highway Access, Public School
Nearby Schools
School District
Winchester School District local
A+
School Safety
2024-25
0.1%
Very Low (Safest)
0.1%
Suspensions
0.1%
In-School
5.4% below state avg
Elementary Schools
10 schools
Acera School
2.1 mi
Grades K-08
The Wilder School
2.2 mi
Grades K-12
A+
Ambrose Elementary School
0.3 mi
|
#13 of 825
|
Score: 65.8
Improved 34 spots from last year
+7.6 above state avg
377 students
Moderate
Rising School
Strong Attendance
Grades K-05
A+
Vinson-Owen Elementary School
0.9 mi
|
#46 of 825
|
Score: 62.7
Improved 106 spots from last year
+4.5 above state avg
387 students
Diverse
Rising School
Strong Attendance
Grades PK-05
A+
Lynch Elementary School
1.3 mi
|
#87 of 825
|
Score: 59.9
Dropped 5 spots from last year
+1.7 above state avg
472 students
Diverse
Diverse Student Body
Strong Attendance
Grades PK-05
Children's Own School
1.4 mi
Grades PK-K
A+
Lincoln Elementary School
1.4 mi
|
#73 of 825
|
Score: 60.6
Dropped 28 spots from last year
+2.4 above state avg
338 students
Moderate
Strong Attendance
Grades K-05
Creative Corner School Inc
1.6 mi
Grades PK-K
St. Mary Elementary School
1.7 mi
Grades PK-05
A+
Muraco Elementary School
2.0 mi
|
#64 of 825
|
Score: 61.2
Improved 60 spots from last year
+3 above state avg
296 students
Diverse
Rising School
Strong Attendance
Grades K-05
Middle Schools
1 school
A+
McCall Middle School
1.4 mi
|
#15 of 352
|
Score: 62.8
Dropped 2 spots from last year
+4.6 above state avg
1,053 students
Diverse
Strong Attendance
Grades 06-08
High Schools
1 school
A+
Winchester High School
1.6 mi
|
#16 of 346
|
Score: 74.0
Improved 19 spots from last year
+15.8 above state avg
1,418 students
Diverse
20 sports
• 2,818 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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Loan Amount
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After down payment
Total Interest
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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$1,471
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
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$0
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Rate Impact
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
Wedgemere
1 Overlook Way, Winchester MA 01890
Winchester, MA 01890
Listing Information
Listing Agent
Lynne Russo
Listing Office
Better Homes and Gardens Real Estate - The Shanahan Group
Office Phone
781-729-9030
Agent MLS ID
CN237333
Office MLS ID
AN0122
Listing Data Updated
Sep 23, 2026 4:33 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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