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  3. Winthrop, MA
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  5. 249 Winthrop Shore Drive
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249 Winthrop Shore Drive

249 Winthrop Shore Dr., Winthrop, MA, 02152

YEAR BUILT

1900

# STORIES

1

# TOTAL UNITS

13

UNIT SIZE RANGE

940-1,460 sqft

Description

249 Winthrop Shore Drive stands in Winthrop, close to the intersection of Western Avenue and Claremont Terrace. This low-rise structure consists of one story and 13 condominium units. The building, constructed in 1900, offers waterfront views, creating a serene setting. The Atlantic Ocean lies nearby, enhancing the coastal atmosphere. Unit sizes range from 940 to 1,460 square feet, catering to different needs. The units include 2, 3, and 4 bedrooms, providing options for various lifestyles. Prices for units fall between $400,000 and $446,000. The average price per square foot is $479, reflecting current market trends. The average days on market for units is about 37, highlighting a brisk selling pace. The building maintains several amenities. These include laundry facilities, golf options, hot water access, and nearby bike paths. Residents enjoy easy access to highways and public transportation. Nearby, Crest Avenue Pizza and Brothers Restaurant offer dining options, while Hair Expressions provides local educational services. Parks, conservation areas, and tennis courts enhance the community atmosphere. The garden area contributes to the outdoor experience. Overall, the building showcases low-rise architecture with a focus on comfort. Waterfront views and nearby amenities create a pleasant living environment. The property suits those looking for a blend of tranquility and accessibility in a vibrant community.

Building ImageMLS ID #71809575
Building ImageView Listing

249 Winthrop Shore Drive

249 Winthrop Shore Dr., Winthrop, MA, 02152

YEAR BUILT

1900

# STORIES

1

# TOTAL UNITS

13

UNIT SIZE RANGE

940-1,460 sqft

Description

249 Winthrop Shore Drive stands in Winthrop, close to the intersection of Western Avenue and Claremont Terrace. This low-rise structure consists of one story and 13 condominium units. The building, constructed in 1900, offers waterfront views, creating a serene setting. The Atlantic Ocean lies nearby, enhancing the coastal atmosphere. Unit sizes range from 940 to 1,460 square feet, catering to different needs. The units include 2, 3, and 4 bedrooms, providing options for various lifestyles. Prices for units fall between $400,000 and $446,000. The average price per square foot is $479, reflecting current market trends. The average days on market for units is about 37, highlighting a brisk selling pace. The building maintains several amenities. These include laundry facilities, golf options, hot water access, and nearby bike paths. Residents enjoy easy access to highways and public transportation. Nearby, Crest Avenue Pizza and Brothers Restaurant offer dining options, while Hair Expressions provides local educational services. Parks, conservation areas, and tennis courts enhance the community atmosphere. The garden area contributes to the outdoor experience. Overall, the building showcases low-rise architecture with a focus on comfort. Waterfront views and nearby amenities create a pleasant living environment. The property suits those looking for a blend of tranquility and accessibility in a vibrant community.

Next

Description

249 Winthrop Shore Drive stands in Winthrop, close to the intersection of Western Avenue and Claremont Terrace. This low-rise structure consists of one story and 13 condominium units. The building, constructed in 1900, offers waterfront views, creating a serene setting. The Atlantic Ocean lies nearby, enhancing the coastal atmosphere. Unit sizes range from 940 to 1,460 square feet, catering to different needs. The units include 2, 3, and 4 bedrooms, providing options for various lifestyles. Prices for units fall between $400,000 and $446,000. The average price per square foot is $479, reflecting current market trends. The average days on market for units is about 37, highlighting a brisk selling pace. The building maintains several amenities. These include laundry facilities, golf options, hot water access, and nearby bike paths. Residents enjoy easy access to highways and public transportation. Nearby, Crest Avenue Pizza and Brothers Restaurant offer dining options, while Hair Expressions provides local educational services. Parks, conservation areas, and tennis courts enhance the community atmosphere. The garden area contributes to the outdoor experience. Overall, the building showcases low-rise architecture with a focus on comfort. Waterfront views and nearby amenities create a pleasant living environment. The property suits those looking for a blend of tranquility and accessibility in a vibrant community.

249 Winthrop Shore Drive Key Stats Last 12 months

Avg. Listed Price-

Avg. Sale Price$450,000($479/Sqft.)
Year over year list price0.00%

Year over year sale price 0.00%
Total Listings0 Listed

Total sold1 Sold
Average Days on Market37 days

Average HOA fees per sqft$2 /monthly
Next

Key Stats

Year over year list price0.00%

Year over year sale price0.00%
Total Listings0 Listed

Total sold1 Sold
Average Days on Market37 days

Average HOA fees per sqft$2 /monthly

Glen Gardens Estate Availability & Demand

Unit Availability

-
High availability buildings list units frequently.

Unit Availability helps to understand how often units in a particular building are listed for sale as compared with the neighborhood average. Units are rarely listed in buildings with low availability.

Unit Demand

-
Units in high-demand buildings sell quicker.

Unit Demand is a measure of quickly units in a particular building sell as compared with other buildings in the neighborhood. Units in high-demand buildings sell more quickly.

For Sale 0 For Sale

249 Winthrop Shore Drive Inventory & Sale History

UnitSize (sqft)BedsBathsDays On MarketDateStatusPrice
Unit 66141521772025-12-15
MLS#: 73436878
Closed$479,000
Unit 1194021372024-12-20
MLS#: 73312277
Closed$450,000
Unit 221040212102022-08-31
MLS#: 72938875
Closed$420,000
Unit 1
1

2 Beds

1 Baths

940 sqft


DateStatusPrice
2024-12-20Closed$450,000
MLS#: 73312277
Days On Market37
Unit 2
2

2 Beds

1 Baths

1040 sqft


DateStatusPrice
2022-08-31Closed$420,000
MLS#: 72938875
Days On Market210
Unit 6
6

2 Beds

1 Baths

1415 sqft


DateStatusPrice
2025-12-15Closed$479,000
MLS#: 73436878
Days On Market77
View Complete Unit Listing HistorySource By: MLSPIN

Amenities

What makes life at 249 Winthrop Shore so appealing? The amenities! Whether you're an outdoor enthusiast looking for a tennis court to perfect your serve, or a nature lover eager to explore the nearby parks and conservation areas, there’s something for everyone. For those who prefer to stay active, you'll enjoy easy access to bike paths and golf options. Plus, laundry facilities and hot water are included, so you'll have all your bases covered.

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Amenities Description

What makes life at 249 Winthrop Shore so appealing? The amenities! Whether you're an outdoor enthusiast looking for a tennis court to perfect your serve, or a nature lover eager to explore the nearby parks and conservation areas, there’s something for everyone. For those who prefer to stay active, you'll enjoy easy access to bike paths and golf options. Plus, laundry facilities and hot water are included, so you'll have all your bases covered.

Parking
Parking
Locker
Locker
Concierge
Concierge
Elevator(s)
Elevator(s)
Central AC
Central AC
Pool
Pool
Fitness Center
Fitness Center
-
Visitors Parking
Visitors Parking
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Amenities

Laundry

Laundry

Tennis Court(s)

Tennis Court(s)

Storage

Storage

Balcony

Balcony

Policies

Worried about restrictions? You’ll be pleased to know that there are no major restrictions here, giving you the flexibility to enjoy your new space to the fullest. This is especially exciting for first-time buyers who want a bit of freedom in how they personalize their new home.

Pet Allowed
Pet Allowed
BBQ Permitted
BBQ Permitted
Sublet Allowed
Sublet Allowed
Short-term Rental Allowed
Short-term Rental Allowed

Compare with Buildings in the Neighbourhood (Last 12 Months)

Compare building's average price/sq. ft. and HOA fees/sq. ft. to buildings nearby

Building NameAvg price per square footAVG HOA FEE per square foot (Monthly)
249 Winthrop Shore Drive$479/sqft.$2 /sqft.
103 Summit Ave$539/sqft.$4 /sqft.
95-97 Summit Ave$468/sqft.$4 /sqft.
45 Grovers Ave$443/sqft.$6 /sqft.
10 Beach Road$338/sqft.$3 /sqft.
Grandview Condominium Association$448/sqft.$2 /sqft.

Nearby Schools

249 Winthrop Shore Drive is situated close to local schools in Winthrop Beach, Winthrop. Nearby educational institutions within 2 miles support daily convenience. Families enjoy improved accessibility and reduced commute stress. This location promotes a family-oriented environment.

Winthrop Middle School

B-
Public|Grades 6–8
60 Payson St|0.39 miles away

Winthrop High School

C+
Public|Grades 9–12
400 Main St|0.4 miles away

William P. Gorman/Fort Banks Elementary School

--
Public|Grades PK–2
101 Kennedy Rd|0.44 miles away

Arthur T. Cummings Elementary School

B-
Public|Grades 3–5
40 Hermon St|0.75 miles away

Beachmont Veterans Memorial School

A-
Public|Grades PK–5
15 Everard Ave|1.31 miles away

Seacoast School

--
Public|Grades 9–12
15 Everard Ave|1.31 miles away
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Schools

arrow rightWhat to know about schoolsarrow right
Next

Description

249 Winthrop Shore Drive is situated close to local schools in Winthrop Beach, Winthrop. Nearby educational institutions within 2 miles support daily convenience. Families enjoy improved accessibility and reduced commute stress. This location promotes a family-oriented environment.

Winthrop Middle School

B-
Public|Grades 6–8
60 Payson St|Less than 1 Mile Away

Winthrop High School

C+
Public|Grades 9–12
400 Main St|Less than 1 Mile Away

William P. Gorman/Fort Banks Elementary School

--
Public|Grades PK–2
101 Kennedy Rd|Less than 1 Mile Away

Arthur T. Cummings Elementary School

B-
Public|Grades 3–5
40 Hermon St|Less than 1 Mile Away

Beachmont Veterans Memorial School

A-
Public|Grades PK–5
15 Everard Ave|1.31 Miles Away

Seacoast School

--
Public|Grades 9–12
15 Everard Ave|1.31 Miles Away

Curtis Guild Elementary School

D
Public|Grades PK–5
195 Leyden St|1.66 Miles Away

Manassah E. Bradley Elementary School

B+
Public|Grades PK–5
110 Beachview Rd|1.77 Miles Away

Garfield Elementary School

D+
Public|Grades KG–5
176 Garfield Ave|1.76 Miles Away

Garfield Middle School

C
Public|Grades 6–8
176 Garfield Ave|1.76 Miles Away

Transit

249 Winthrop Shore Drive benefits from a network of nearby public transportation options within a 2-mile radius. Access to Bus, Metro ensures convenient travel to employment hubs and local destinations. Strong transit connectivity reduces travel time and improves daily convenience. A transit-friendly location adds value for residents and visitors alike.

160 Waldemar Ave

1.9 miles away|37 min walk

171 Faywood Ave

1.88 miles away|37 min walk

200 Endicott Ave

1.1 miles away|22 min walk

202 Orient Ave

1.9 miles away|37 min walk

220 Waldemar Ave

1.95 miles away|38 min walk

560 Winthrop Ave

1.72 miles away|34 min walk
Next

Transit

arrow rightWhat to know about transitarrow right
Next

Description

249 Winthrop Shore Drive benefits from a network of nearby public transportation options within a 2-mile radius. Access to Bus, Metro ensures convenient travel to employment hubs and local destinations. Strong transit connectivity reduces travel time and improves daily convenience. A transit-friendly location adds value for residents and visitors alike.

160 Waldemar Ave

1.9 miles away|37 min walk

171 Faywood Ave

1.88 miles away|37 min walk

200 Endicott Ave

1.1 miles away|22 min walk

202 Orient Ave

1.9 miles away|37 min walk

220 Waldemar Ave

1.95 miles away|38 min walk

560 Winthrop Ave

1.72 miles away|34 min walk

99 Veterans Rd

0.37 miles away|8 min walk

Beachmont

1.42 miles away|28 min walk

Beachmont - Bennington St @ Winthrop Ave

1.4 miles away|27 min walk

Beachmont - State Rd @ Winthrop Ave

1.43 miles away|28 min walk

Beachmont - Winthrop Ave

1.43 miles away|28 min walk

Beach Rd @ Locust St

0.05 miles away|2 min walk

Bennington St @ Antrim St

1.71 miles away|33 min walk

Bennington St @ Trident St

1.93 miles away|38 min walk

Boardman St @ Ashley St

1.99 miles away|39 min walk

Boardman St @ Saratoga St

1.85 miles away|36 min walk

Crescent Ave @ Orchard St

1.15 miles away|23 min walk

Crescent Ave @ Summer St

0.97 miles away|19 min walk

Crescent Ave @ Webster St

1.06 miles away|21 min walk

Crescent Ave @ Winthrop Ave

1.23 miles away|24 min walk

Crescent Ave @ Winthrop Pkwy

0.87 miles away|17 min walk

Crest Ave @ Grovers Ave

0.12 miles away|3 min walk

Crest Ave @ Highland Ave

0.3 miles away|6 min walk

Crest Ave @ Revere St

0.3 miles away|6 min walk

Crestway Rd @ Faywood Ave

1.78 miles away|35 min walk

Deer Island - MWRA Gate

1.88 miles away|37 min walk

Endicott Ave @ Atlantic Ave

1.45 miles away|28 min walk

Endicott Ave @ Leverett Ave

1.31 miles away|26 min walk

Endicott Ave opp Bradstreet Ave

0.96 miles away|19 min walk

Endicott Ave @ Waterview Ave

1.16 miles away|23 min walk

Main St @ Pleasant St

0.96 miles away|19 min walk

Main St @ Read St

0.77 miles away|15 min walk

Main St @ Winthrop St

0.51 miles away|10 min walk

Orient Ave @ Drumlin Rd

1.78 miles away|35 min walk

Orient Ave @ Faywood Ave

1.49 miles away|29 min walk

Orient Ave opp Beachview Rd

1.58 miles away|31 min walk

Orient Ave @ Selma St

1.67 miles away|32 min walk

Orient Heights

1.64 miles away|32 min walk

Orient Heights - Bennington St

1.66 miles away|32 min walk

Orient Heights - Saratoga St Barnes Ave

1.64 miles away|32 min walk

Orient Heights South Busway Berth B2

1.66 miles away|32 min walk

Pauline St opp Woodside Ave

0.9 miles away|18 min walk

Pauline St @ Pleasant St

1.11 miles away|22 min walk

Pauline St @ Woodside Ave

0.9 miles away|18 min walk

Pleasant St @ Bartlett Rd

1 miles away|20 min walk

Pleasant St @ Buchanan St

0.92 miles away|18 min walk

Pleasant St @ Seaview Ave

0.89 miles away|18 min walk

Pleasant St @ Somerset Ave

1.09 miles away|21 min walk

Pleasant St @ Sunnyside Ave

0.93 miles away|18 min walk

Pleasant St @ Vine Ave

0.88 miles away|17 min walk

The Neighbourhood: Winthrop Beach

Winthrop Beach is a coastal neighborhood with a wide public beach and shoreline paths. The area features parks, picnic spots, and places to watch boats and wildlife. The district includes small shops, cafes, casual restaurants, a grocery store, and playgrounds. Local groups run seasonal events and ocean-focused programs in the summer months. Public buses connect the district to nearby towns and to larger city transit hubs, and short drives bring more shopping and job options. The area sits in Suffolk County, Massachusetts, near major roads and city services.

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Neighbourhood Description

Winthrop Beach is a coastal neighborhood with a wide public beach and shoreline paths. The area features parks, picnic spots, and places to watch boats and wildlife. The district includes small shops, cafes, casual restaurants, a grocery store, and playgrounds. Local groups run seasonal events and ocean-focused programs in the summer months. Public buses connect the district to nearby towns and to larger city transit hubs, and short drives bring more shopping and job options. The area sits in Suffolk County, Massachusetts, near major roads and city services.

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249 Winthrop Shore Drive Demographics

This neighborhood indicates a good mix of people which makes it a good place for families. About 14.57% are children aged 0–14, 18.26% are young adults between 15–29, 20.04% are adults aged 30–44, 22.31% are in the 45–59 range and 24.82% are seniors aged 60 and above. Commuting options are also varying where 69.71% of residents relying on driving, while others prefer public transit around 18.84%, walking around 2.34%, biking around 0.67%, allowing residents to choose travel modes that best fit their daily routines. Most homes in the area are with 51.84% of units owner occupied and 48.16% are rented. The neighborhood offers different household types. About 31.43% are single family homes and 6.57% are multi family units. Around 33.72% are single-person households, while 66.28% are multi person households. This mix works well for families, roommates, and individuals. Education levels in the neighborhood vary widely where 23.53% of residents have bachelor’s degrees. Around 30.98% have high school or college education. Another 8.45% hold diplomas while 13.03% have completed postgraduate studies. The remaining are 24.01% with other types of qualifications.

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Demographics Description

This neighborhood indicates a good mix of people which makes it a good place for families. About 14.57% are children aged 0–14, 18.26% are young adults between 15–29, 20.04% are adults aged 30–44, 22.31% are in the 45–59 range and 24.82% are seniors aged 60 and above. Commuting options are also varying where 69.71% of residents relying on driving, while others prefer public transit around 18.84%, walking around 2.34%, biking around 0.67%, allowing residents to choose travel modes that best fit their daily routines. Most homes in the area are with 51.84% of units owner occupied and 48.16% are rented. The neighborhood offers different household types. About 31.43% are single family homes and 6.57% are multi family units. Around 33.72% are single-person households, while 66.28% are multi person households. This mix works well for families, roommates, and individuals. Education levels in the neighborhood vary widely where 23.53% of residents have bachelor’s degrees. Around 30.98% have high school or college education. Another 8.45% hold diplomas while 13.03% have completed postgraduate studies. The remaining are 24.01% with other types of qualifications.

Age Demographics

0–14 Years

14.57%

15–29 Years

18.26%

30–44 Years

20.04%

45–59 Years

22.31%

60+ Years

24.82%

Commute

18.84%

Transit

2.34%

Walk

69.71%

Drive

0.67%

Bike

Housing Ownership

51.84%

Owner Occupied

48.16%

Rental Units

Household Types

Single Family
31.43%
Multi Family
6.57%
Single Person
33.72%
Multi Person
66.28%

Average Income

Household:$7,527,400.29 /yr

Individual:$4,662,391.69 /yr

Education

Bachelors Degree23.53%
High School College30.98%
Diploma8.45%
Post Graduate13.03%
Others24.01%
Next

Education

Diploma8.45%
Post Graduate13.03%
Others24.01%
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  1. Home
  2. /Winthrop, MA
  3. /
    249 Winthrop Shore Drive
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