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14 Nassau Drive Winchester — Photo 1 of 30

14 Nassau Drive Winchester — Photo 1 of 30

Recent Drop: $51,000

$2,850,000
$2,799,000

$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.

View Standard Listing

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

Original Price$2,850,000
Annual Taxes$24,082.8

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms11
Fireplaces3
FlooringWood, Tile, Flooring - Hardwood
BasementFull, Finished, Walk-Out Access, Interior Entry, Sump Pump, Concrete

Climate & Utilities

HeatingForced Air, Oil, Fireplace
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningR1

Property & Lot

Acres0.43
SqFt Lot18,637
Lot FeaturesCleared

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

Third
Bedroom 5
Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 3
First
Living RoomDining RoomKitchenOfficeFamily RoomBathroom 1Bathroom 2
Living Room
Lvl First

15 x 25

Flooring - Hardwood, French Doors

Dining Room
Lvl First

15 x 18

Flooring - Hardwood, Wet Bar, Recessed Lighting, Decorative Molding

Kitchen
Lvl First

14 x 35

Flooring - Stone/Ceramic Tile, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Cabinets - Upgraded, Open Floorplan

Office
Lvl First

12 x 15

Closet/Cabinets - Custom Built, Flooring - Hardwood, French Doors

Family Room
Lvl First

16 x 30

Cathedral Ceiling(s), Coffered Ceiling(s), Flooring - Hardwood

Primary Bedroom
Lvl Second

18 x 23

Bathroom - Full, Cathedral Ceiling(s), Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Hot Tub / Spa

Bedroom 2
Lvl Second

14 x 15

Bedroom 3
Lvl Second

12 x 12

Bathroom - Full, Bathroom - Double Vanity/Sink, Closet, Flooring - Hardwood

Bedroom 4
Lvl Second

13 x 14

Bathroom - Full, Closet, Flooring - Hardwood

Bedroom 5
Lvl Third

16 x 21

Bathroom - Full, Closet, Flooring - Hardwood

Bathroom 1
Lvl First

10 x 10

Bathroom - Half, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl First

6 x 8

Bathroom - Half, Flooring - Stone/Ceramic Tile

Bathroom 3
Lvl Second

8 x 15

Bathroom - Full, Flooring - Stone/Ceramic Tile

Property History

Price Drop
$2,799,000

Was $2,850,000

May 4, 2026

MLS® 73500890

Listed
$2,850,000

Apr 14, 2026

MLS® 73500890

Expired
$2,850,000

Dec 31, 2025

MLS® 73434748

Listed
$2,850,000

Sep 24, 2025

MLS® 73434748

Expired
$2,850,000

Jun 30, 2025

MLS® 73360219

Listed
$2,850,000

Apr 16, 2025

MLS® 73360219

Listing Provided By

Listing Agent: Weidong Li

Listing Office: WINN Real Estate & Consulting

MLS® Number: 73500890