Experience a complete transformation in this meticulously renovated 2-family home. Perched on a prized corner lot, this residence has undergone extensive updates, including new flooring, walls, electrical, kitchen, plumbing, and a newer roof. The result is a modern, move-in-ready space. Enjoy breathtaking, unobstructed views of Winthrop's verdant Golf Course from all three levels. This oversized property offers flexible living arrangements. Winthrop itself is a coastal gem, boasting beautiful beaches, scenic parks, and convenient access to Deer Island and downtown Boston via the water ferry. A vibrant dining scene and thriving yacht clubs contribute to the area's dynamic atmosphere. Commuting is made easy with brand-new MBTA bus lines. Plus, a new middle and high school, along with a state-of-the-art track and football field, enhance the community's appeal.
Sold for $1,060,000
$1,060,000
86 Chester Ave, Winthrop, MA 02152
6beds
2,692sqft
Multi Family
Built in 1900
-- sqft lot
$1,072,500 Zestimate®
$394/sqft
$3,805 Estimated rent
Home value
$1,072,500
Estimated sales range
Not available
$3,805/mo
Zestimate® history
Owner options
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$3,805/mo
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$6,264/mo
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List your homeWhat's special
Modern move-in-ready spaceNewer roofCorner lotExtensive updatesNew flooring
Zillow last checked:
Listing updated:
Listed by:
Kyle Macnichol 978-500-7273,
Redfin Corp. 617-340-7803
Bought with:
Karin O Connor
Compass
Source: MLS PIN,MLS#: 73361929
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Appliances
- Included: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Washer/Dryer
Features
- Ceiling Fan(s), Pantry, Crown Molding, Stone/Granite/Solid Counters, Upgraded Cabinets, Upgraded Countertops, Open Floorplan, Remodeled, Living Room, Dining Room, Kitchen, Family Room, Laundry Room, Sunroom
- Flooring: Wood, Tile, Hardwood
- Windows: Picture Window
- Basement: Full
- Has fireplace: No
Interior area
- Total structure area: 2,692
- Total interior livable area: 2,692 sqft
- Finished area above ground: 2,692
Property
Parking
- Total spaces: 9
- Parking features: Paved Drive, Off Street, Tandem, Paved
- Garage spaces: 2
- Uncovered spaces: 7
Features
- Patio & porch: Deck
- Fencing: Fenced
- Waterfront features: 1/2 to 1 Mile To Beach, Beach Ownership(Public)
- Frontage type: Golf Course
Lot
- Size: 4,378 sqft
- Features: Corner Lot
Details
- Parcel number: M:037 L:066,1422682
- Zoning: RAS
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Multi Family
Materials
- Foundation: Block
Condition
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range
Community & neighborhood
Community
- Community features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Bike Path, Highway Access, House of Worship, Marina, Public School, T-Station
Location
- Region: Winthrop
HOA & financial
Other financial information
- Total actual rent: 0
Other
Other facts
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 8/15/2025 | Sold | $1,060,000-3.5%$394/sqft |
Source: MLS PIN #73361929 Report a problem | ||
| 5/31/2025 | Contingent | $1,099,000$408/sqft |
Source: MLS PIN #73361929 Report a problem | ||
| 4/21/2025 | Listed for sale | $1,099,000+30.8%$408/sqft |
Source: MLS PIN #73361929 Report a problem | ||
| 5/30/2019 | Listing removed | $839,999$312/sqft |
Source: CENTURY 21 Seaport #72456578 Report a problem | ||
| 4/15/2019 | Pending sale | $839,999$312/sqft |
Source: CENTURY 21 Seaport #72456578 Report a problem | ||
| 2/25/2019 | Listed for sale | $839,999+5%$312/sqft |
Source: CENTURY 21 Seaport #72456578 Report a problem | ||
| 8/13/2018 | Listing removed | $799,999$297/sqft |
Source: CENTURY 21 Seaport #72318478 Report a problem | ||
| 7/13/2018 | Price change | $799,999-4.2%$297/sqft |
Source: CENTURY 21 Seaport #72318478 Report a problem | ||
| 6/18/2018 | Price change | $834,999-1.8%$310/sqft |
Source: CENTURY 21 Seaport #72318478 Report a problem | ||
| 5/1/2018 | Listed for sale | $849,999+193.1%$316/sqft |
Source: Century 21 Seacoast #72318478 Report a problem | ||
| 11/19/2012 | Sold | $290,000-3.3%$108/sqft |
Source: Public Record Report a problem | ||
| 8/29/2012 | Listed for sale | $299,900$111/sqft |
Source: Highland Real Estate #71427708 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,048 +7.7% | $779,800 +8.8% |
| 2024 | $7,471 -5% | $717,000 -2.4% |
| 2023 | $7,863 +1.6% | $734,900 +11.6% |
| 2022 | $7,742 +2.2% | $658,300 +10.2% |
| 2021 | $7,576 +2.6% | $597,500 +2.2% |
| 2020 | $7,381 +1.5% | $584,900 +6.1% |
| 2019 | $7,269 +10.6% | $551,500 +18.8% |
| 2018 | $6,573 +10.2% | $464,200 +12.2% |
| 2017 | $5,964 +5.5% | $413,900 +12.5% |
| 2016 | $5,655 +12.8% | $367,900 +5.3% |
| 2015 | $5,012 +11.8% | $349,500 +16.3% |
| 2013 | $4,482 +2.9% | $300,600 |
| 2012 | $4,356 +2.7% | $300,600 -2.2% |
| 2011 | $4,242 +0.9% | $307,400 -7.2% |
| 2010 | $4,205 +6.6% | $331,100 -16.3% |
| 2009 | $3,944 +1.5% | $395,600 -5.3% |
| 2008 | $3,886 +2.5% | $417,900 -2.8% |
| 2007 | $3,791 +4.6% | $429,800 +2.4% |
| 2006 | $3,625 +2.8% | $419,600 +7.4% |
| 2005 | $3,525 +1% | $390,800 +17.1% |
| 2004 | $3,491 +2.1% | $333,700 |
| 2003 | $3,420 +5.4% | $333,700 +62.5% |
| 2002 | $3,244 +28.2% | $205,300 |
| 2000 | $2,531 | $205,300 |
Find assessor info on the county website
Neighborhood: 02152
Nearby schools
GreatSchools rating
- 5/10Arthur T. Cummings Elementary SchoolGrades: 3-5Distance: 0.3 mi
- 8/10Winthrop Middle SchoolGrades: 6-8Distance: 0.3 mi
- 5/10Winthrop Sr High SchoolGrades: 9-12Distance: 0.4 mi
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Estimated market value
$1,072,500
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,072,500
- Massachusetts
- Suffolk County
- Winthrop
- 02152
- 86 Chester Ave
Nearby cities
Nearby zip codes
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