
129 Strandway Winthrop — Photo 1 of 34
$1,275,000
Investment Analysis — 129 Strandway
Winthrop, MA 02152
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 02152 carries an estimated $3,470/mo in gross rent — about a 1.69% cap rate and $21,572/yr in estimated NOI at the $1,275,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
3
SqFt
2,599
Style
Single Family
Built
1900
Welcome to your ultimate beachfront oasis in Winthrop, where every day feels like a permanent getaway with direct access from your back door straight into the sand. This stunning home features an inviting, fireplaced living room, a kitchen boasting sleek marble countertops and tile flooring, a convenient main-floor full bath and an outdoor shower for rinsing off after the beach, and two flexible bedrooms ideal for guests, children, or a home office. Take in breathtaking ocean sunrises over morning coffee from the year-round heated sunroom, and retreat upstairs to a spacious primary suite complete with its own private bath. The finished lower level functions as a fully separate suite—an incredible asset as one of only 10 legal Airbnbs in all of Winthrop, complete with its own family room, bonus space, full bathroom, and laundry. Positioned in an unbeatable location with two off-street parking spots and an EV charger, this property sits less than 1 mile from the Winthrop Landing MBTA ferry for easy transit to Logan, Central Wharf, and the Seaport, perfectly balancing everyday coastal luxury with elite short-term rental potential.
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 2,599 sq ft principal dwelling). Lot size: 4,520 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
Gas Water Heater • Dishwasher • Disposal • Refrigerator
Neighborhood
Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Medical Facility
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl FirstFlooring - Wood
Kitchen
Lvl FirstFlooring - Stone/Ceramic Tile, Dining Area, Recessed Lighting, Stainless Steel Appliances
Family Room
Lvl BasementFlooring - Laminate, Recessed Lighting
Primary Bedroom
Lvl SecondCloset, Flooring - Wall to Wall Carpet
Bedroom 2
Lvl FirstBedroom 3
Lvl FirstCloset, Flooring - Vinyl
Bedroom 4
Lvl BasementCloset, Flooring - Laminate, Recessed Lighting
Bathroom 1
Lvl FirstBathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl SecondBathroom - Full, Bathroom - With Shower Stall, Flooring - Stone/Ceramic Tile
Bathroom 3
Lvl BasementBathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile
Property History
$1,275,000
Oct 2, 2026
MLS® 73585487
$1,324,900
Sep 15, 2026
MLS® 73452093
$1,324,900
Nov 6, 2025
MLS® 73452093
$350,000
Mar 5, 2011
MLS® 71164535
$375,000
Nov 20, 2010
MLS® 71164535
Listing Agent: Kyle Macnichol
Listing Office: Redfin Corp.
MLS® Number: 73585487








