
1 Overlook Way Winchester — Photo 1 of 39
$1,850,000
Investment Analysis — 1 Overlook Way
Winchester, MA 01890 — Wedgemere
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 1.08% cap rate and $19,924/yr in estimated NOI at the $1,850,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
2.5
SqFt
3,092
Style
Single Family
Built
1941
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.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,092 sq ft principal dwelling). Lot size: 15,705 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
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Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Range • Dishwasher • Trash Compactor • Microwave • Refrigerator • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Conservation Area
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First18 x 13
Flooring - Hardwood, Window(s) - Bay/Bow/Box
Dining Room
Lvl Main,First13 x 12
Closet/Cabinets - Custom Built, Flooring - Hardwood, Chair Rail
Kitchen
Lvl Main,First17 x 13
Flooring - Stone/Ceramic Tile, Window(s) - Bay/Bow/Box, Dining Area, Countertops - Stone/Granite/Solid, Open Floorplan, Recessed Lighting, Stainless Steel Appliances
Family Room
Lvl First20 x 15
Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Exterior Access, Open Floorplan, Recessed Lighting, Slider
Primary Bedroom
Lvl Second19 x 13
Bathroom - Full, Bathroom - Double Vanity/Sink, Ceiling Fan(s), Flooring - Hardwood, Double Vanity, Closet - Double
Bedroom 2
Lvl Second16 x 13
Bedroom 3
Lvl Second19 x 12
Flooring - Hardwood, Attic Access, Closet - Double
Bedroom 4
Lvl Second12 x 12
Closet, Flooring - Hardwood
Bathroom 1
Lvl Main,First6 x 4
Bathroom - Half, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl Second13 x 5
Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile
Bathroom 3
Lvl Second9 x 5
Bathroom - Full, Bathroom - Tiled With Tub & Shower
Listing Agent: Lynne Russo
Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group
MLS® Number: 73581571