
37 Mayflower Road Winchester — Photo 1 of 42
$3,149,000
Investment Analysis — 37 Mayflower Road
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 7-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 0.25% cap rate and $7,740/yr in estimated NOI at the $3,149,000 list price. Adjust every assumption in the calculator below.
Beds
7
Baths
7.5
SqFt
8,540
Style
Single Family
Built
2009
Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.
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 8,540 sq ft principal dwelling). Lot size: 20,051 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.
Open Houses
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator
Neighborhood
Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails • Golf
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First20 x 16
Flooring - Hardwood, Lighting - Sconce
Dining Room
Lvl First20 x 15
Flooring - Hardwood, Lighting - Sconce, Lighting - Pendant
Kitchen
Lvl First22 x 13
Flooring - Hardwood, Countertops - Upgraded, Kitchen Island, Breakfast Bar / Nook, Country Kitchen, Exterior Access, Recessed Lighting, Lighting - Pendant, Lighting - Overhead
Office
Lvl First16 x 14
Fireplace, Flooring - Hardwood, Wet bar
Family Room
Lvl First21 x 18
Ceiling Fan(s), Flooring - Hardwood, Recessed Lighting, Lighting - Sconce
Master Bedroom
Lvl Second30 x 20
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Double Vanity, Dressing Room, Recessed Lighting, Lighting - Sconce, Closet - Double
Bedroom 2
Lvl Second17 x 16
Bedroom 3
Lvl Second22 x 17
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Bedroom 4
Lvl Second18 x 17
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Recessed Lighting
Bedroom 5
Lvl Second15 x 15
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Hardwood, Recessed Lighting
Bathroom 1
Lvl First9 x 6
Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl Second15 x 13
Bathroom - Full, Flooring - Stone/Ceramic Tile
Bathroom 3
Lvl Second10 x 9
Bathroom - Full, Flooring - Stone/Ceramic Tile
Property History
$3,149,000
Sep 8, 2026
MLS® 73573670
$3,179,000
Sep 3, 2026
MLS® 73502853
$3,179,000
Apr 16, 2026
MLS® 73502853
$3,537,000
Apr 14, 2026
MLS® 73475646
$3,537,000
Feb 9, 2026
MLS® 73475646
$1,899,999
May 2, 2011
MLS® 71012550
$1,899,999
Dec 23, 2009
MLS® 71012550
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73573670
