For Sale
Multi family home for sale at 66 Sunnyside Ave, Winthrop, MA 02152 | MLS# 73529063 | Listing updated on 2026-07-14
Photo 1 of Multi family home for sale at 66 Sunnyside Ave, Winthrop, MA 02152 | MLS# 73529063 | Listing updated on 2026-07-14
Photo 2 of Multi family home for sale at 66 Sunnyside Ave, Winthrop, MA 02152 | MLS# 73529063 | Listing updated on 2026-07-14
Photo 3 of Multi family home for sale at 66 Sunnyside Ave, Winthrop, MA 02152 | MLS# 73529063 | Listing updated on 2026-07-14
Photo 4 of Multi family home for sale at 66 Sunnyside Ave, Winthrop, MA 02152 | MLS# 73529063 | Listing updated on 2026-07-14
38+
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Street View

$999,888

Monthly Est:$4,977

  • Beds Icon5 Beds
  • Beds Icon
    2 Baths
  • Beds Icon2,635sqft

66 Sunnyside Ave, Winthrop, MA 02152

$4,977/moEst:

Get Pre-Approved

  • Multi Family

  • Built in 1920

  • $-- HOA

  • 0.12 acre lot

  • $379/sq.ft

Description

NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or savvy investors. Unit 1 rents for $3,100/mo and Unit 2 for $4,000/mo, generating $85,200 in gross annual income with a net of $76,900. Five bedrooms, two full baths, and a versatile layout ideal for extended families. The property features an enclosed porch, deck, fenced yard, professional landscaping, and individually metered electric. Minutes from downtown Boston via Rt. 1A. Don't miss this opportunity; schedule your private showing today!

  • Houzeo last checked: 10 minutes ago
  • Listing updated: July 14, 2026 at 7:05 am
  • Listing Provided by: Mirna Orellana (617) 650-7187 | COM-PRO Real Estate Services, Inc (617) 381-9010
  • Source: MLS Property Information Network-MA | MLS#: 73529063 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    3

  • County

    Suffolk County

  • City

    Winthrop

  • Neighborhood

    --

  • Year Built

    1920

  • HOA Fees

    -

  • Finished Area

    2,635 sqft

  • Lot Size

    0.12 acre lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73529063

  • MLS Status

    Active

  • Days on Market

    129

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 2

Interior

  • Sewer

    Public Sewer

  • Exterior Features

    Professional Landscaping

Construction

  • Year Built

    Year Built: 1920

  • Home type

    Multi Family

  • Roof

    Rubber

  • Foundation Details

    Brick/mortar

Utilities & Energy

  • Water Source

    Public

  • Basement

    Walk Out Access, Interior Entry, Sump Pump, Concrete

  • Electric

    Circuit Breakers, Individually Metered

  • Parking Features

    Off Street, Paved

Other Features

  • Disclosures

    Property Is Located In A Flood Zone. Basement Is Equipped With A Sump Pump System. The Seller Reserves The Right To Accept An Offer At Any Time

  • Lot Features

    Other

  • Patio And Porch Features

    Enclosed, Deck

Price History

DateEventPrice

07/10/2026

Source: mls_logoMLS Property Information Network-MA #73529063

Price Decreased

$999,888 -16.61%

$379/sqft

06/03/2026

Source: mls_logoMLS Property Information Network-MA #73529063

Listed for Sale

$1,199,000 +31.04%

$455/sqft

04/08/2024

Source: mls_logoMLS Property Information Network-MA #73204490

Price Increased

$915,000 +1.67%

$347/sqft

04/08/2024

Source: mls_logoMLS Property Information Network-MA #73204490

Sold

$900,000

$342/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 11, 2026, 03:15AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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