Active
128 Days on market
27 Billows St Winthrop — Photo 1 of 25

27 Billows St Winthrop — Photo 1 of 25

Recent Drop: $15,000

$855,000
$840,000

$840,000

27 Billows St, Winthrop, MA 02152

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!

Key facts

It was listed on May 28, 2026. The price has come down from an original $875,000 to $840,000 across 2 changes, most recently on August 17, 2026. The annual property taxes are $7,229 (2026 tax year). It sits on a 0.09-acre (3,870 sq ft) lot.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$457/sqft
Local Avg (Winthrop)$469/sqft
3% BelowMarket Average

* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.

Property Details

Financials

Original Price$875,000
Annual Taxes$7,229

Parking

Garage0
Off-Street5

Interior Specifications

Total Rooms6
Fireplaces1
FlooringTile, Carpet, Hardwood, Laminate
BasementFull, Unfinished

Climate & Utilities

HeatingForced Air, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningR

Property & Lot

Acres0.09
SqFt Lot3,870
Lot FeaturesCorner Lot

Amenities & Appliances

Gas Water Heater • Range • Disposal • Refrigerator • Freezer • Washer • Dryer

Neighborhood

Public Transportation • Park • Walk/Jog Trails • Golf • Bike Path • Conservation Area

Geography

Floorplan Breakdown

Structural Layout

Third
Bedroom 2Bedroom 3Bathroom 3
Second
Primary BedroomBathroom 2
First
Living RoomDining RoomKitchenBathroom 1
Living Room
Lvl First

15 x 13

Beamed Ceilings, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Open Floorplan, Recessed Lighting

Dining Room
Lvl First

19 x 12

Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Open Floorplan, Recessed Lighting, Lighting - Pendant

Kitchen
Lvl First

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

Primary Bedroom
Lvl Second

17 x 10

Bathroom - Full, Closet, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Lighting - Overhead

Bedroom 2
Lvl Third

13 x 10

Bedroom 3
Lvl Third

13 x 10

Closet, Flooring - Wall to Wall Carpet, Window(s) - Bay/Bow/Box, Recessed Lighting

Bathroom 1
Lvl First

9 x 9

Bathroom - Full

Bathroom 2
Lvl Second

7 x 5

Bathroom - Full, Bathroom - Tiled With Shower Stall, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead

Bathroom 3
Lvl Third

Bathroom - Half

Property History

Price Drop
$840,000

Was $855,000

Aug 17, 2026

MLS® 73526371

Price Drop
$855,000

Was $875,000

Jun 24, 2026

MLS® 73526371

Listed
$875,000

May 28, 2026

MLS® 73526371

Questions about this home

When was 27 Billows St, Winthrop listed?

27 Billows St, Winthrop was listed on May 28, 2026.

Has the price of 27 Billows St, Winthrop changed?

The price has come down from an original $875,000 to $840,000 across 2 changes, most recently on August 17, 2026.

What are the property taxes for 27 Billows St, Winthrop?

The annual property taxes for 27 Billows St, Winthrop are $7,229 (2026 tax year).

How big is the lot at 27 Billows St, Winthrop?

27 Billows St, Winthrop sits on a 0.09-acre (3,870 sq ft) lot.

What is the status of 27 Billows St, Winthrop?

27 Billows St, Winthrop is actively listed for sale.

Population

18,759

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$116K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

43.1%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Suffolk County

2,337 housing units permitted in the last 12 months (+13% vs the prior 12 months) — 2,062 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

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 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 Provided By

Listing Agent: Reserve Team

Listing Office: Reference Real Estate

MLS® Number: 73526371