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129 Strandway Winthrop — Photo 1 of 34

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.

View Standard Listing

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

Original Price$1,275,000
Annual Taxes$10,074

Parking

Garage0
Off-Street2

Interior Specifications

Total Rooms6
Fireplaces1
FlooringTile, Engineered Hardwood, Flooring - Stone/Ceramic Tile
BasementFull, Finished, Interior Entry

Climate & Utilities

HeatingBaseboard, Natural Gas
CoolingNone
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationBlock
Zoningres

Property & Lot

Acres0.1
SqFt Lot4,520
Lot FeaturesFlood Plain

Amenities & Appliances

Gas Water Heater • Dishwasher • Disposal • Refrigerator

Neighborhood

Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Medical Facility

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBathroom 2
First
Living RoomKitchenBedroom 2Bedroom 3Bathroom 1
Basement
Family RoomBedroom 4Bathroom 3
Living Room
Lvl First

Flooring - Wood

Kitchen
Lvl First

Flooring - Stone/Ceramic Tile, Dining Area, Recessed Lighting, Stainless Steel Appliances

Family Room
Lvl Basement

Flooring - Laminate, Recessed Lighting

Primary Bedroom
Lvl Second

Closet, Flooring - Wall to Wall Carpet

Bedroom 2
Lvl First
Bedroom 3
Lvl First

Closet, Flooring - Vinyl

Bedroom 4
Lvl Basement

Closet, Flooring - Laminate, Recessed Lighting

Bathroom 1
Lvl First

Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl Second

Bathroom - Full, Bathroom - With Shower Stall, Flooring - Stone/Ceramic Tile

Bathroom 3
Lvl Basement

Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile

Property History

Listed
$1,275,000

Oct 2, 2026

MLS® 73585487

Terminated
$1,324,900

Sep 15, 2026

MLS® 73452093

Listed
$1,324,900

Nov 6, 2025

MLS® 73452093

Sold
$350,000

Mar 5, 2011

MLS® 71164535

Listed
$375,000

Nov 20, 2010

MLS® 71164535

Listing Provided By

Listing Agent: Kyle Macnichol

Listing Office: Redfin Corp.

MLS® Number: 73585487