Emma D'Angelo
Charlesgate Realty Group LLC
(339) 444-1135
20 Total Sales
2 in Downtown Winthrop
$730K - $830K Price Range
86 Chester Ave Winthrop, MA 02152
Downtown Winthrop NeighborhoodEstimated Value: $982,000 - $1,135,000
6
Beds
2.5
Baths
2,692
Sq Ft
$396/Sq Ft
Est. Value
Highlights
- Marina
- On Golf Course
- Deck
- William P. Gorman/Fort Banks Elementary School Rated A-
- Open Floorplan
- Property is near golf course, public transit, and schools
About This Home
As of August 2025Experience 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.
Last Agent to Sell the Property
Kyle MacNichol
Redfin Corp. Listed on: 04/21/2025
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Property Details
Home Type
- Multi-Family
Est. Annual Taxes
- $8,048
Year Built
- Built in 1900
Lot Details
- 4,378 Sq Ft Lot
- On Golf Course
- Fenced
- Corner Lot
Parking
- 2 Car Garage
- Tandem Parking
- Driveway
- Open Parking
- Off-Street Parking
Home Design
- Block Foundation
Interior Spaces
- 2,692 Sq Ft Home
- Property has 1 Level
- Open Floorplan
- Crown Molding
- Ceiling Fan
- Family Room
- Living Room
- Dining Room
- Sun or Florida Room
- Basement Fills Entire Space Under The House
- Washer and Dryer
Kitchen
- Range
- Microwave
- Dishwasher
- Solid Surface Countertops
- Disposal
Flooring
- Wood
- Tile
Bedrooms and Bathrooms
- 6 Bedrooms
Additional Features
- Deck
- Property is near golf course, public transit, and schools
Listing and Financial Details
- Assessor Parcel Number M:037 L:066,1422682
Community Details
Recreation
- Marina
- Tennis Courts
- Park
- Jogging Path
- Bike Trail
Additional Features
- 2 Units
- Shops
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Apr 21, 2025
Closed on
Aug 15, 2025
Sold by
Bought by
Seller's Agent
Kyle MacNichol
Redfin Corp.
Buyer's Agent
Karin O Connor
Compass
List Price
$1,099,000
Sold Price
$1,060,000
Premium/Discount to List
-$39,000
-3.55%
Views
34
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$5,032
Avg. Annual Appreciation
0.47%
Original Mortgage
$890,400
Outstanding Balance
$882,415
Interest Rate
6.67%
Mortgage Type
New Conventional
Estimated Equity
$182,617
Purchase Details
Closed on
Aug 16, 2022
Sold by
Bought by
Purchase Details
Listed on
Aug 28, 2012
Closed on
Dec 17, 2012
Sold by
Bought by
Seller's Agent
Mary Ann Cash
Charlesgate Realty Group, llc
Buyer's Agent
Susan Tallent
Coldwell Banker Residential Brokerage - Winthrop
List Price
$299,900
Sold Price
$290,000
Premium/Discount to List
-$9,900
-3.3%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
9.92%
Original Mortgage
$210,000
Interest Rate
3.39%
Mortgage Type
New Conventional
Purchase Details
Listed on
Aug 28, 2012
Closed on
Nov 19, 2012
Sold by
Bought by
Seller's Agent
Mary Ann Cash
Charlesgate Realty Group, llc
Buyer's Agent
Susan Tallent
Coldwell Banker Residential Brokerage - Winthrop
List Price
$299,900
Sold Price
$290,000
Premium/Discount to List
-$9,900
-3.3%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$210,000
Interest Rate
3.39%
Mortgage Type
New Conventional
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Downtown Winthrop, MA
-
Emma D'Angelo
-
Mostafa Elbadaoui
Mostafa Elbadaoui
United Brokers
(857) 305-4613
41 Total Sales
1 in Downtown Winthrop
$280,000 Price
-
Juan Lopera-Martinez
Juan Lopera-Martinez
eXp Realty LLC
(339) 338-4961
85 Total Sales
1 in Downtown Winthrop
$950,000 Price
-
Carrie Abysalh
Carrie Abysalh
RE/MAX Prof Associates
(774) 541-2667
60 Total Sales
1 in Downtown Winthrop
$527,000 Price
-
Juan Jaramillo
Juan Jaramillo
(857) 465-4065
60 Total Sales
4 in Downtown Winthrop
$330K - $1.3M Price Range
-
Jose Duce Rocher
JD
Jose Duce Rocher
Century 21 Limitless
(781) 633-6951
153 Total Sales
1 in Downtown Winthrop
$593,500 Price
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $1,060,000 | -- | ||
| -- | None Available | ||
| -- | -- | ||
| $290,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Open | $890,400 | ||
| Closed | $303,000 | ||
| Previous Owner | $269,000 | ||
| Previous Owner | $210,000 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 08/15/2025 08/15/25 | Sold | $1,060,000 | -3.5% | $394 / Sq Ft | |
| 05/27/2025 05/27/25 | Pending | -- | -- | -- | |
| 04/21/2025 04/21/25 | For Sale | $1,099,000 | +279.0% | $408 / Sq Ft | |
| 11/19/2012 11/19/12 | Sold | $290,000 | -3.3% | $119 / Sq Ft | View Prior Sale |
| 10/20/2012 10/20/12 | Pending | -- | -- | -- | |
| 08/28/2012 08/28/12 | For Sale | $299,900 | -- | $123 / Sq Ft |
Source: MLS Property Information Network (MLS PIN)
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $8,048 | $779,800 | $331,400 | $448,400 |
| 2024 | $7,471 | $717,000 | $318,500 | $398,500 |
| 2023 | $7,863 | $734,900 | $291,500 | $443,400 |
| 2022 | $7,742 | $658,300 | $260,400 | $397,900 |
| 2021 | $7,576 | $597,500 | $232,500 | $365,000 |
| 2020 | $7,381 | $584,900 | $232,500 | $352,400 |
| 2019 | $7,269 | $551,500 | $214,300 | $337,200 |
| 2018 | $6,573 | $464,200 | $184,000 | $280,200 |
| 2017 | $5,964 | $413,900 | $162,900 | $251,000 |
| 2016 | $5,655 | $367,900 | $141,700 | $226,200 |
| 2015 | $5,012 | $349,500 | $137,600 | $211,900 |
| 2014 | $4,528 | $290,600 | $127,900 | $162,700 |
Source: Public Records
Agents Affiliated with this Home
-
K
Seller's Agent in 2025
Kyle MacNichol
Redfin Corp.
-
Karin O Connor
Buyer's Agent in 2025
Karin O Connor
Compass
(617) 448-5003
1 in this area
34 Total Sales
-
Mary Ann Cash
M
Seller's Agent in 2012
Mary Ann Cash
Charlesgate Realty Group, llc
(617) 846-1234
14 in this area
43 Total Sales
-
S
Buyer's Agent in 2012
Susan Tallent
Coldwell Banker Residential Brokerage - Winthrop
Map
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73361929
APN: WINT-000037-000000-000066
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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.
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