66 Sunnyside Ave, Winthrop, MA, 02152
About This Home
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!
Getting Around
Very Walkable
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1920
Materials
- Foundation: Brick/Mortar
- Roof: Rubber
Type & Style
- Home type: MultiFamily
- Property subType: Multi Family
Interior
Basement
- Has basement: Yes
- Basement: Walk-Out Access,Interior Entry,Sump Pump,Concrete
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 2
- Full bathrooms: 2
Features
- Finished area above ground: 2,635
Interior Area
- Total structure area: 2,635
- Total interior livable area: 2,635 sqft
Property
Details
- Parcel number: M:0022 B:0091 L:0000,1421230
- Zoning: Res
Features
- Patio & porch: Enclosed,Deck
- Exterior features: Professional Landscaping
- Fencing: Fenced
- Has view: Yes
- View description: Water,Bay,Harbor,Marsh,Ocean
- Has water view: Yes
- Water view: Bay,Harbor,Marsh,Ocean,Water
- On waterfront: Yes
- Waterfront features: Waterfront,Bay,Ocean,1/10 to 3/10 To Beach,Beach Ownership(Public)
Lot
- Lot size: 5,336 sqft
- Features: Other
Parking
- Total spaces: 2
- Parking features: Off Street,Paved
- Has uncovered spaces: Yes
- Uncovered spaces: 2
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Coastal Flooding
- Heat Wave
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $5,055 | $60,660 |
| Home Insurance * | $408 | $4,896 |
| Property Taxes | $853 | $10,236 |
| Electricity | $519 | $6,235 |
| Total | $6,835 | $82,020 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-10 | Price change | $999,888 |
| 2026-06-03 | Listed for sale | $1,199,000 |
| 2024-04-08 | Sold | $915,000 |
| 2024-03-04 | Contingent | $900,000 |
| 2024-02-22 | Listed for sale | $900,000 |
| 2023-10-27 | Sold | $500,000 |
For Sale by Agent
View on Zillow