
27 Billows St Winthrop — Photo 1 of 25
Recent Drop: $35,000
$840,000
Winthrop, MA 02152 — Point Shirley
Beds
3
Baths
2.5
SqFt
1,837
Style
Single Family
Built
1900
This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a renovated kitchen with white beadboard cabinetry, quartz countertops, subway tile backsplash, and stainless appliances. The entire 2nd floor is dedicated to a private primary retreat, complete with two closets and a private en suite with glass shower. The sun-filled sitting room connects the suite to the 2nd-floor deck where ocean views make for the perfect spot for morning coffee or evening entertaining. A wood spiral staircase leads to the third-floor bedrooms tucked under vaulted ceilings. Corner lot with 2 driveways & the opportunity to expand the yard practically on the water in Pt. Shirley!
* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.
Gas Water Heater • Range • Disposal • Refrigerator • Freezer • Washer • Dryer
Public Transportation • Park • Walk/Jog Trails • Golf • Bike Path • Conservation Area
15 x 13
Beamed Ceilings, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Open Floorplan, Recessed Lighting
19 x 12
Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Open Floorplan, Recessed Lighting, Lighting - Pendant
15 x 8
Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Cabinets - Upgraded, Exterior Access, Recessed Lighting, Remodeled, Stainless Steel Appliances
17 x 10
Bathroom - Full, Closet, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Lighting - Overhead
13 x 10
13 x 10
Closet, Flooring - Wall to Wall Carpet, Window(s) - Bay/Bow/Box, Recessed Lighting
9 x 9
Bathroom - Full
7 x 5
Bathroom - Full, Bathroom - Tiled With Shower Stall, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead
Bathroom - Half
Was $855,000
Aug 17, 2026
MLS® 73526371
Was $875,000
Jun 24, 2026
MLS® 73526371
May 28, 2026
MLS® 73526371
18,759
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
43.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
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 1,837 sq ft principal dwelling). Lot size: 3,870 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.
Listing Agent: Reserve Team
Listing Office: Provided by MLS PIN
MLS® Number: 73526371
Explore other active listings in the area.