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66 Sunnyside Ave, Winthrop MA 02152
66 Sunnyside Ave, Winthrop MA 02152
Massachusetts>Winthrop Town>Cottage Park

66 Sunnyside AveWinthrop, MA 02152

For Sale

$999,888

Smart Buyer Rebate $4,999

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!

Listed by Mirna Monterrosa Orellana

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COM-PRO Real Estate Services, Inc

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617-650-7187

Last updated July 14, 2026

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Source: MLSPin #73529063

Listing Facts

  • TypeMulti-family
  • NeighborhoodCottage Park
  • Bedrooms5
  • Bathrooms2
  • Days on Prevu58
  • Taxes$9,928/year
  • Size2,635 sqft
  • Price per sqft$379

Amenities

  • Private Outdoor Space
  • Parking

Location

Mortgage Calculator

Listing History

07/11/2026
Price Decreased
$999,888
06/03/2026
Listed by COM-PRO Real Estate Services, Inc
$1,199,000

Property Details for 66 Sunnyside Ave

Exterior

Construction

  • Number Of Units Total: 2
  • Roof: Rubber
  • Stories: 3
  • Stories Total: 3
  • Year Built: 1920
  • Year Built Details: Actual
  • Exterior Features: Professional Landscaping

Features

  • Fencing: Fenced
  • Patio And Porch Features: Enclosed, Deck
  • Road Frontage Type: Public
  • Waterfront Features: Waterfront, Bay, Ocean, 1/10 To 3/10 To Beach, Beach Ownership(Public)
  • Waterfront: Yes

Measurements

  • Building Area Total: 2,635
  • Building Area Units: Square Feet
  • Lot Features: Other
  • Lot Size Acres: 0.12
  • Lot Size Area: 0
  • Lot Size Square Feet: 5,336
  • Lot Size Units: Acres

Financial

Residential Income

  • Gross Income: $85,200.00
  • Operating Expense: $8,300.00

Taxes

  • Parcel Number: M:0022 B:0091 L:0000,1421230
  • Tax Annual Amount: $9,928.00
  • Tax Assessed Value: $891,200.00
  • Tax Year: 2026

Interior

Measurements

  • Living Area: 2,635
  • Living Area Source: Public Record

Rooms

  • Basement: Walk-Out Access, Interior Entry, Sump Pump, Concrete
  • Bathrooms Full: 2
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 5
  • Rooms Total: 16

Other

Location

  • Tax Block: 0091
  • Tax Lot: 0000

Parking

Parking

  • Open Parking Spaces: 2
  • Open Parking: Yes
  • Parking Features: Off Street, Paved
  • Parking Total: 2

Utilities

Equipment

  • Electric: Circuit Breakers, Individually Metered
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this multi-family home have?

There are 5 bedrooms and 2 bathrooms in this multi-family home at 66 Sunnyside Ave.

Does this multi-family home have parking?

Yes, there are 2 parking spaces available for 66 Sunnyside Ave.

What are the annual taxes for 66 Sunnyside Ave?

Annual taxes for this multi-family home are estimated at $9,928.

How does 66 Sunnyside Ave compare to other multi-family homes in Cottage Park?

This multi-family home is listed 0% below the average price for multi-family homes in Cottage Park and has been on the market for 2 more days than the typical home in this area.

What is the square footage on this multi-family home?

According to the MLS, this listing is 2,635 sqft.

66 Sunnyside Ave is a 5-bedroom, 2-bath multi-family home for sale in Winthrop MA 02152. Available on Prevu for 58 days at $999,888. This includes a recent price decrease of $199,112. This home features 2,635 square feet of living space, located in Winthrop Town. The median listing price for multi-family homes in this area is $974,944. The home offers private outdoor space and parking. View other multi-family home listings in Winthrop Town.

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.