276 High Street Winchester — Photo 1 of 36
Recent Drop: $104,000
$2,195,000
Investment Analysis — 276 High Street
Winchester, MA 01890 — Cox Road / High St Extension neighborhood
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 0.65% cap rate and $14,357/yr in estimated NOI at the $2,195,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
3.5
SqFt
5,006
Style
Single Family
Built
1992
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!
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 5,006 sq ft principal dwelling). Lot size: 19,998 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.
Immersive Experience
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Range • Oven • Dishwasher • Disposal • Trash Compactor • Microwave • Refrigerator • Freezer • Washer • Dryer • Plumbed For Ice Maker
Neighborhood
Public Transportation • Shopping • Tennis Court(s) • Park • Golf • Bike Path
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First15 x 14
Flooring - Hardwood, Open Floorplan, Sunken, Lighting - Overhead
Dining Room
Lvl First15 x 15
Flooring - Hardwood, Window(s) - Picture, French Doors, Lighting - Pendant, Lighting - Overhead
Kitchen
Lvl Main,First16 x 15
Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, French Doors, Kitchen Island, Breakfast Bar / Nook, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Lighting - Pendant
Office
Lvl First14 x 11
Closet, Flooring - Hardwood, Lighting - Overhead
Family Room
Lvl First30 x 22
Ceiling Fan(s), Flooring - Hardwood, Balcony / Deck, Deck - Exterior, Exterior Access, Lighting - Overhead
Master Bedroom
Lvl Second26 x 23
Bathroom - Full, Bathroom - Double Vanity/Sink, Closet - Linen, Flooring - Stone/Ceramic Tile, French Doors, Lighting - Sconce, Lighting - Overhead
Bedroom 2
Lvl Second17 x 14
Bedroom 3
Lvl Second15 x 13
Ceiling Fan(s), Closet, Lighting - Overhead
Bedroom 4
Lvl Second14 x 12
Ceiling Fan(s), Closet, Lighting - Overhead
Bedroom 5
Lvl Third24 x 22
Ceiling Fan(s), Closet, Lighting - Overhead
Bathroom 1
Lvl First8 x 5
Bathroom - Half
Bathroom 2
Lvl Second13 x 12
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Closet, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub
Bathroom 3
Lvl Second9 x 9
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower
Property History
$2,195,000
Was $2,299,000
May 13, 2026
MLS® 73496396
$2,299,000
Apr 6, 2026
MLS® 73496396
$2,299,000
Dec 16, 2025
MLS® 73404344
$2,299,000
Jul 14, 2025
MLS® 73404344
$2,399,000
Jun 16, 2025
MLS® 73349101
$2,399,000
Mar 24, 2025
MLS® 73349101
$2,750,000
Dec 31, 2024
MLS® 73170437
$2,750,000
Oct 14, 2023
MLS® 73170437
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73496396
