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217 Pleasant StreetWinthrop, MA 02152

For Sale

$939,000

Smart Buyer Rebate $4,695

UNBELIEVABLE VALUE MEETS UNMATCHED OPPORTUNITY. The best value proposition in Winthrop. Sellers are highly motivated and have re-priced the property aggressively to prompt a sale. Buyers can secure instant equity for the newly optimized price point. Featuring over 2,600 square feet of living space (plus additional 600+ sq ft in finished basement) gleaming hardwood floors, fireplaces, a partially finished lower level, and a very welcoming front porch, every space invites you to relax, gather, and create lasting memories. Extensive upgrades, including updated electrical, plumbing, heating, central A/C and very efficient mini spit system. Outside, enjoy a good sized, fenced backyard, large 2-car detached garage, and plenty of off-street parking. At this price, opportunities like this are hard to find in this section of Winthrop! Come experience the charm, space, and value for yourself! Very easy to view! Book your appointment now before it is too late!

Listed by Louis Bonavita

·

Benton Real Estate Company

·

4134787535

Last updated October 29, 2026

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Source: MLSPin #73567723

Listing Facts

  • TypeSingle-family
  • NeighborhoodDowntown Winthrop
  • Bedrooms6
  • Bathrooms3
  • Days on Prevu67
  • Taxes$9,003/year
  • Size2,650 sqft
  • Price per sqft$354

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

10/29/2026
Price Decreased
$939,000
10/08/2026
Price Decreased
$947,900
09/29/2026
Price Decreased
$949,900
09/11/2026
Price Decreased
$979,900
08/25/2026
Listed by Benton Real Estate Company
$998,900
  1. 10/29/2026$939,000
    Price Decreased
  2. 10/08/2026$947,900
    Price Decreased
  3. 09/29/2026$949,900
    Price Decreased
  4. 09/11/2026$979,900
    Price Decreased
  5. 08/25/2026$998,900
    Listed by Benton Real Estate Company

Property Details for 217 Pleasant Street

Association

Amenities

  • Community Features: Park, Golf

Exterior

Construction

  • Roof: Shingle
  • Year Built: 1896
  • Year Built Details: Actual,Renovated Since
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Rain Gutters

Features

  • Fencing: Fenced
  • Patio And Porch Features: Porch
  • Waterfront Features: Ocean Front

Measurements

  • Building Area Total: 2,650
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.14
  • Lot Size Area: 0
  • Lot Size Square Feet: 6,210
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 1421640
  • Tax Annual Amount: $9,003.00
  • Tax Assessed Value: $808,200.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Gas Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Plumbed For Ice Maker
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Wood, Tile

Measurements

  • Living Area: 2,650
  • Living Area Source: Other

Rooms

  • Basement: Partially Finished
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 6
  • Rooms Total: 10

Other

General

  • Exclusions: Custom Art-Work In Living Room.

Parking

Parking

  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 5
  • Open Parking: Yes
  • Parking Features: Paved, Detached, Off Street, Driveway
  • Parking Total: 7

Utilities

Equipment

  • Cooling: Central Air, Other, Zoned
  • Has Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Natural Gas, Forced Air, Other, Zoned
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

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

There are 6 bedrooms and 3 bathrooms in this single-family home at 217 Pleasant Street.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 217 Pleasant Street.

What are the annual taxes for 217 Pleasant Street?

Annual taxes for this single-family home are estimated at $9,003.

How does 217 Pleasant Street compare to other single-family homes in Downtown Winthrop?

This single-family home is listed 13% above the average price for single-family homes in Downtown Winthrop and has been on the market for 2 more days than the typical home in this area.

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

According to the MLS, this listing is 2,650 sqft.

217 Pleasant Street is a 6-bedroom, 3-bath single-family home for sale in Winthrop MA 02152. Listed on Prevu for 67 days at $939,000. This includes a recent price decrease of $8,900. This home features 2,650 square feet of living space, located in Downtown Winthrop. The median listing price for single-family homes in this area is $629,450. Property amenities include private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Explore more single-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.