
50 Holland Street Winchester — Photo 1 of 42
$1,549,000
Investment Analysis — 50 Holland Street
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 3-bedroom in 01890 carries an estimated $3,730/mo in gross rent — about a 1.51% cap rate and $23,419/yr in estimated NOI at the $1,549,000 list price. Adjust every assumption in the calculator below.
Beds
3
Baths
2.5
SqFt
2,640
Style
Single Family
Built
1960
Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!
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 2,640 sq ft principal dwelling). Lot size: 6,625 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
Open Houses
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator
Neighborhood
Public Transportation • Shopping • Tennis Court(s) • Park • Golf • Medical Facility
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First18 x 14
Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood
Dining Room
Lvl First14 x 12
Closet/Cabinets - Custom Built, Flooring - Hardwood, Wine Chiller, Lighting - Overhead
Kitchen
Lvl Main,First22 x 12
Flooring - Stone/Ceramic Tile, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Lighting - Pendant
Office
Lvl Basement14 x 11
Closet, Lighting - Overhead
Family Room
Lvl Basement17 x 13
Ceiling Fan(s), Closet, Recessed Lighting
Primary Bedroom
Lvl Second23 x 15
Ceiling Fan(s), Closet, Flooring - Hardwood
Bedroom 2
Lvl Second23 x 13
Bedroom 3
Lvl First15 x 12
Ceiling Fan(s), Closet, Flooring - Hardwood, Deck - Exterior, Exterior Access, Slider
Bathroom 1
Lvl First8 x 8
Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Recessed Lighting
Bathroom 2
Lvl Second8 x 5
Bathroom - Tiled With Tub & Shower, Lighting - Overhead
Bathroom 3
Lvl Basement11 x 10
Bathroom - Half
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73556633