
14 Nassau Drive Winchester — Photo 1 of 30
Recent Drop: $51,000
$2,799,000
Investment Analysis — 14 Nassau Drive
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 0.48% cap rate and $13,491/yr in estimated NOI at the $2,799,000 list price. Adjust every assumption in the calculator below.
Beds
6
Baths
6
SqFt
6,968
Style
Single Family
Built
2002
Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.
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 6,968 sq ft principal dwelling). Lot size: 18,637 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.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Range • Oven • Dishwasher • Disposal • Microwave • Refrigerator • Wine Refrigerator • Range Hood
Neighborhood
Shopping • Park • Walk/Jog Trails • Medical Facility • Conservation Area • House of Worship
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First15 x 25
Flooring - Hardwood, French Doors
Dining Room
Lvl First15 x 18
Flooring - Hardwood, Wet Bar, Recessed Lighting, Decorative Molding
Kitchen
Lvl First14 x 35
Flooring - Stone/Ceramic Tile, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Cabinets - Upgraded, Open Floorplan
Office
Lvl First12 x 15
Closet/Cabinets - Custom Built, Flooring - Hardwood, French Doors
Family Room
Lvl First16 x 30
Cathedral Ceiling(s), Coffered Ceiling(s), Flooring - Hardwood
Primary Bedroom
Lvl Second18 x 23
Bathroom - Full, Cathedral Ceiling(s), Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Hot Tub / Spa
Bedroom 2
Lvl Second14 x 15
Bedroom 3
Lvl Second12 x 12
Bathroom - Full, Bathroom - Double Vanity/Sink, Closet, Flooring - Hardwood
Bedroom 4
Lvl Second13 x 14
Bathroom - Full, Closet, Flooring - Hardwood
Bedroom 5
Lvl Third16 x 21
Bathroom - Full, Closet, Flooring - Hardwood
Bathroom 1
Lvl First10 x 10
Bathroom - Half, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl First6 x 8
Bathroom - Half, Flooring - Stone/Ceramic Tile
Bathroom 3
Lvl Second8 x 15
Bathroom - Full, Flooring - Stone/Ceramic Tile
Property History
$2,799,000
Was $2,850,000
May 4, 2026
MLS® 73500890
$2,850,000
Apr 14, 2026
MLS® 73500890
$2,850,000
Dec 31, 2025
MLS® 73434748
$2,850,000
Sep 24, 2025
MLS® 73434748
$2,850,000
Jun 30, 2025
MLS® 73360219
$2,850,000
Apr 16, 2025
MLS® 73360219
Listing Agent: Weidong Li
Listing Office: WINN Real Estate & Consulting
MLS® Number: 73500890








