66 Sunnyside Ave, Winthrop MA 02152
Winthrop, MA 02152 • Cottage Park
$1,199,000
$999,888
Est. $6,083/month
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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!
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Recently Sold Nearby
Property History
Market Insights
1
Price Changes
23.7%
Price Range
1
Previous Sales
Property Timeline
Price Reduced
Jul 10, 2026
$999,888
$199,112
(-16.61%)
From $1,199,000 to $999,888 (-16.6%)
Listed for Sale
Jun 3, 2026
$1,199,000
Original listing
Office: COM-PRO Real Estate Services, Inc
Previous Transaction - MLS #73204490
Full transaction history available when tracking began
Previously Sold
Apr 8, 2024
$915,000
MLS #73204490
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/10/2026 | ↓ Price Reduced | $999,888 | $199,112 | - | From $1,199,000 to $999,888 (-16.6%) |
| 06/03/2026 | 🏠 Listed for Sale | $1,199,000 | - | - | Original listing |
| 04/08/2024 | 🏷️ Previously Sold | $915,000 | - | - | MLS #73204490 |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $9,928 | $891,200 |
Financial Details
Annual Property Tax
$9,928
Tax Year 2026
Assessed Value
$891,200
Facts & Features
Home Facts
Type
Residential Income
Style
Multi Family
Year Built
1920
Living Area
2,635 sq ft
Lot Size
0.12 acres
Bedrooms
5
Full Baths
2
Total Rooms
16
Investment Metrics
Units
2
Unit 1 Rent
$3,100/mo · Y
Unit 2 Rent
$4,000/mo · Y
Total Monthly Rent
$7,100/mo
Gross Income
$85,200
Net Operating Income
$76,900
Operating Expenses
$8,300
Water/Sewer Expense
$3,000
Insurance Expense
$3,200
Cap Rate
7.69%
Interior
Heating
None
Cooling
None
Flooring
None
Appliances
None
Fireplace
None
Basement
Walk-out Access, Interior Entry, Sump Pump, Concrete
Laundry
None
Features
None
Exterior
Construction
None
Architecture
None
Roof
Rubber
Features
Professional Landscaping
Pool
None
Spa
None
Fencing
Fenced
Patio/Porch
Enclosed, Deck
Parking
Features
Off Street, Paved
Total Spaces
2
Utilities
Electric
Circuit Breakers, Individually Metered
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$9,928
Assessed Value
$891,200
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller 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
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Suffolk
Total market time (incl. prior listings)
41 days
Property Overview
Property Type
Multi Family
Listing Type
For Sale
Year Built
1920
Bedrooms
5
Full Bathrooms
2
Living Area
2,635 sq ft
Total Rooms
16
Stories
3
Levels
3
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,635 sq ft above grade
Display Options
Outdoor Areas
Patio & porchEnclosed, Deck
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Walk-Out Access, Interior Entry, Sump Pump, Concrete
Laundry:
Security:
Construction & Materials
Year Built:
1920
Structure Type:
Exterior Materials:
Roof:
Rubber
Foundation:
Brick/Mortar
Stories:
3
Heating, Cooling & Utilities
Heating:
Cooling:
Hot Water:
Natural Gas
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Professional Landscaping
Patio & Porch:
Enclosed, Deck
Fencing:
Fenced
Other Structures:
Lot Features:
Other
Road Surface:
Parking & Garage
Total Parking Spaces:
2
Parking Features:
Off Street, Paved
Special Features
Waterfront:
Yes
Waterfront Type:
Waterfront, Bay, Ocean, 1/10 to 3/10 To Beach, Beach Ownership(Public)
Community Amenities:
Nearby Schools
School District
Winthrop School District local
C
School Safety
2024-25
0.3%
Low
0.3%
Suspensions
5.2% below state avg
Elementary Schools
2 schools
B-
Arthur T. Cummings Elementary School
0.5 mi
|
#453 of 824
|
Score: 46.0
Improved 101 spots from last year
-12.2 below state avg
467 students
Less Diverse
Rising School
Strong Attendance
Grades 03-05
William P. Gorman/Fort Banks Elementary School
1.0 mi
487 students
Less Diverse
Grades PK-02
Middle Schools
1 school
B+
Winthrop Middle School
0.8 mi
|
#119 of 352
|
Score: 47.4
Dropped 26 spots from last year
-10.8 below state avg
439 students
Less Diverse
Grades 06-08
High Schools
1 school
C+
Winthrop High School
0.7 mi
|
#241 of 346
|
Score: 47.2
Dropped 112 spots from last year
-11 below state avg
568 students
Less Diverse
18 sports
• 1,118 athletes
College Ready Curriculum
Strong Athletics
Grades 09-12
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
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Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$827
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
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Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
Cottage Park
66 Sunnyside Ave, Winthrop MA 02152
Winthrop, MA 02152
Listing Information
Listing Agent
Mirna Monterrosa Orellana
Listing Office
COM-PRO Real Estate Services, Inc
Office Phone
617-381-9010
Agent MLS ID
CN229530
Office MLS ID
B95159
Listing Data Updated
Jul 14, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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