550 Pleasant Street
550 Pleasant St., Winthrop, MA, 02152
About 550 Pleasant Street
550 Pleasant Street is a unique condominium building completed in 2007, offering a serene waterfront setting. This single-story structure provides 1 and 2-bedroom units, catering to diverse living preferences. Residents can enjoy a variety of amenities, including access to a fitness center, pool, and clubroom, promoting an active lifestyle. The property also encompasses areas for recreation, with tennis courts and golf facilities available for leisure activities. Additional features include convenient transportation options with public transportation nearby, as well as direct access to a bike path. Garden areas and conservation areas are also present, creating spaces for outdoor enjoyment and nature appreciation. For equestrian enthusiasts, stable facilities are available, contributing to a versatile living experience. 550 Pleasant Street combines modern conveniences with natural beauty. Its waterfront views and proximity to local parks and trails enhance the living experience, offering both tranquility and urban amenities. The single-story architecture makes the property accessible and distinct, emphasizing ease of movement with an included elevator. This combination of features establishes 550 Pleasant Street as a practical and charming option for those seeking a well-rounded lifestyle in a distinctive environment.
Amenities
Living at 550 Pleasant Street comes with an enviable list of amenities that cater to both relaxation and recreation. Picture yourself unwinding beside the pool or joining friends for a game of tennis on the courts. If you're the outdoorsy type, take advantage of the nearby trails for your daily run or bike ride. Other community perks include a fitness center to keep you active, and a clubroom where you can host gatherings with friends. For those who cherish moments of tranquility, there’s a lovely garden area and park to enjoy some fresh air.
Parking
Locker
Concierge
Elevator
Central AC
Pool
Fitness Center-
Visitors ParkingBuilding Policies
As you consider making 550 Pleasant Street your new home, it’s important to note that there are a few community policies in place. While there are restrictions to ensure a pleasant living environment for all residents, the community welcomes potential buyers who share a commitment to fostering a harmonious atmosphere.
Pets Allowed
Short-term Rental Allowed
BBQ Permitted
Sublet AllowedLoading...
550 Pleasant Street Market Report (last 12 months)
Avg. List Price
$550,000 ($551/Sqft.)
Year-Over-Year List Price
15.36%Total Listings
1Avg. Days On Market
75Avg. Sale Price
$545,000 ($546/Sqft.)
Year-Over-Year Sale Price
25.34%Total Sold
1Avg. HOA Fees/Sqft
$2 /monthly
550 Pleasant Street Sales History
| Unit | Size (sqft) | Beds | Baths | Days On Market | Date | Status | Price | |
|---|---|---|---|---|---|---|---|---|
 | 405 | 1972 | 2 | 2 | 72 | 2025-05-02 MLS#: 73335480 | Closed | $825,000 |
 | 205 | 1972 | 2 | 2 | 98 | 2023-08-30 MLS#: 73115741 | Closed | $825,000 |
 | 305 | 1972 | 2 | 2 | 154 | 2008-01-02 MLS#: 70624337 | Closed | $849,000 |
205
2 Beds
2 Baths
1972 sqft
Days On Market98
| Date | Status | Price |
|---|---|---|
| 2023-08-30 | Closed | $825,000 |
MLS#: 73115741
305
2 Beds
2 Baths
1972 sqft
Days On Market154
| Date | Status | Price |
|---|---|---|
| 2008-01-02 | Closed | $849,000 |
MLS#: 70624337
405
2 Beds
2 Baths
1972 sqft
Days On Market72
| Date | Status | Price |
|---|---|---|
| 2025-05-02 | Closed | $825,000 |
MLS#: 73335480
View Complete Unit Listing HistorySource By: MLSPIN
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 Name | Avg price per square foot | AVG HOA FEE per square foot (Monthly) |
|---|---|---|
| 550 Pleasant Street | $546/sqft. | $2 /sqft. |
| 550 Pleasant St | $483/sqft. | $2 /sqft. |
| Governor's Park | $435/sqft. | $2 /sqft. |
| Governors Park | $435/sqft. | $2 /sqft. |
| Governor's Park Condominium | $378/sqft. | $3 /sqft. |
| Governor's Park | $378/sqft. | $3 /sqft. |
Nearby Schools
Discover top-rated schools located close to 550 Pleasant Street.
Arthur T. Cummings Elementary School
B-Public|Grades 3–5
40 Hermon St|0.54 miles away
Winthrop Middle School
B-Public|Grades 6–8
60 Payson St|0.85 miles away
Winthrop High School
C+Public|Grades 9–12
400 Main St|0.86 miles away
William P. Gorman/Fort Banks Elementary School
--Public|Grades PK–2
101 Kennedy Rd|0.91 miles away
Curtis Guild Elementary School
DPublic|Grades PK–5
195 Leyden St|1.12 miles away
Seacoast School
--Public|Grades 9–12
15 Everard Ave|1.36 miles away
Schools
View nearby schools
View nearby schools
Schools
Arthur T. Cummings Elementary School
B-Public|Grades 3–5
40 Hermon St|Less than 1 Mile Away
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
Curtis Guild Elementary School
DPublic|Grades PK–5
195 Leyden St|1.12 Miles Away
Seacoast School
--Public|Grades 9–12
15 Everard Ave|1.36 Miles Away
Beachmont Veterans Memorial School
A-Public|Grades PK–5
15 Everard Ave|1.36 Miles Away
Manassah E. Bradley Elementary School
B+Public|Grades PK–5
110 Beachview Rd|1.38 Miles Away
Excel Academy Charter School
B-Public|Grades 5–12
58 Moore St|1.87 Miles Away
Garfield Middle School
CPublic|Grades 6–8
176 Garfield Ave|2.17 Miles Away
Garfield Elementary School
D+Public|Grades KG–5
176 Garfield Ave|2.17 Miles Away
Edgar a Hooks Elementary School
B-Public|Grades 1–4
300 Crescent Ave|2.57 Miles Away
William a Berkowitz Elementary School
CPublic|Grades 1–4
300 Crescent Ave|2.57 Miles Away
George F. Kelly Elementary School
BPublic|Grades 1–6
300 Crescent Ave|2.57 Miles Away
Frank M Sokolowski Elementary School
CPublic|Grades 1–4
300 Crescent Ave|2.57 Miles Away
Patrick J. Kennedy Elementary School
C+Public|Grades PK–5
343 Saratoga St|2.65 Miles Away
Transit
Experience convenience and connectivity with premium transit options just moments away.
Main St @ Pleasant St
0.18 miles away|4 min walk
Main St @ Read St
0.32 miles away|7 min walk
Walden St @ Lincoln St
0.36 miles away|7 min walk
Walden St @ Ingleside Park
0.43 miles away|9 min walk
Walden St opp Ingleside Park
0.43 miles away|9 min walk
Pauline St opp Woodside Ave
0.53 miles away|11 min walk
Transit
View nearby transit options
View nearby transit options
Transit
Main St @ Pleasant St
0.18 miles away|4 min walk
Main St @ Read St
0.32 miles away|7 min walk
Walden St @ Lincoln St
0.36 miles away|7 min walk
Walden St @ Ingleside Park
0.43 miles away|9 min walk
Walden St opp Ingleside Park
0.43 miles away|9 min walk
Pauline St opp Woodside Ave
0.53 miles away|11 min walk
Pauline St @ Woodside Ave
0.54 miles away|11 min walk
Pauline St @ Pleasant St
0.57 miles away|11 min walk
Saratoga St opp Teragram St
0.59 miles away|12 min walk
Saratoga St @ Teragram St
0.6 miles away|12 min walk
Main St @ Winthrop St
0.67 miles away|13 min walk
Revere St @ Winthrop St
0.69 miles away|14 min walk
Pleasant St @ Somerset Ave
0.69 miles away|14 min walk
Pleasant St @ Bartlett Rd
0.78 miles away|16 min walk
Revere St opp Governors Dr
0.82 miles away|16 min walk
Revere St @ Governors Dr
0.83 miles away|16 min walk
Pleasant St @ Sunnyside Ave
0.9 miles away|18 min walk
Pleasant St @ Buchanan St
0.9 miles away|18 min walk
Walley St @ Gladstone St
0.95 miles away|19 min walk
Suffolk Downs - Bennington St @ Leverett Ave
0.96 miles away|19 min walk
Suffolk Downs - Bennington St opp Leverett Ave
0.97 miles away|19 min walk
Suffolk Downs
0.98 miles away|19 min walk
Suffolk Downs - Bennington St
0.98 miles away|19 min walk
Pleasant St @ Seaview Ave
0.99 miles away|19 min walk
Pleasant St @ Vine Ave
1 miles away|20 min walk
Suffolk Downs - Walley St
1.02 miles away|20 min walk
Orient Heights - Saratoga St Barnes Ave
1.04 miles away|20 min walk
Orient Heights
1.04 miles away|20 min walk
Orient Ave @ Faywood Ave
1.04 miles away|21 min walk
Orient Heights South Busway Berth B2
1.05 miles away|21 min walk
Revere St opp Summit Ave
1.05 miles away|21 min walk
Revere St @ Summit Ave
1.06 miles away|21 min walk
Orient Heights - Bennington St
1.07 miles away|21 min walk
Pleasant St @ Winthrop St
1.09 miles away|21 min walk
Washington Ave @ Winthrop St
1.09 miles away|21 min walk
Bennington St @ Antrim St
1.12 miles away|22 min walk
Orient Ave opp Beachview Rd
1.12 miles away|22 min walk
Veterans Rd @ Hadassah Way
1.14 miles away|22 min walk
Veterans Rd @ Shirley St
1.15 miles away|23 min walk
Revere St @ Golden Dr
1.17 miles away|23 min walk
Revere St @ Hutchinson St
1.18 miles away|23 min walk
Shirley St @ Beach Rd
1.18 miles away|23 min walk
Shirley St opp Coral Ave
1.19 miles away|23 min walk
99 Veterans Rd
1.2 miles away|24 min walk
Orient Ave @ Selma St
1.21 miles away|24 min walk
Washington Ave opp Willow Ave
1.22 miles away|24 min walk
Washington Ave @ Willow Ave
1.23 miles away|24 min walk
Shirley St opp Seafoam Ave
1.24 miles away|24 min walk
Crest Ave @ Revere St
1.25 miles away|25 min walk
Crest Ave @ Highland Ave
1.26 miles away|25 min walk
Veterans Rd @ Locust St
1.28 miles away|25 min walk
Beach Rd @ Locust St
1.29 miles away|25 min walk
Boardman St @ Saratoga St
1.29 miles away|25 min walk
Crescent Ave @ Summer St
1.32 miles away|26 min walk
Washington Ave opp Lewis Ave
1.32 miles away|26 min walk
Shirley St @ Levy Bramson Way
1.32 miles away|26 min walk
Veterans Rd @ Levy Bramson Way
1.32 miles away|26 min walk
Crescent Ave @ Webster St
1.32 miles away|26 min walk
Washington Ave @ Lewis Ave
1.33 miles away|26 min walk
Orient Ave @ Drumlin Rd
1.34 miles away|26 min walk
Bennington St @ Trident St
1.35 miles away|26 min walk
Crest Ave @ Grovers Ave
1.35 miles away|26 min walk
Crescent Ave @ Orchard St
1.36 miles away|27 min walk
Crescent Ave @ Winthrop Pkwy
1.39 miles away|27 min walk
Crestway Rd @ Faywood Ave
1.42 miles away|28 min walk
Crescent Ave @ Winthrop Ave
1.45 miles away|28 min walk
Veterans Rd @ Cutler St
1.46 miles away|28 min walk
Bennington St @ Westbrook St
1.46 miles away|28 min walk
Shirley St @ Cutler St
1.46 miles away|29 min walk
Washington Ave opp River Rd
1.46 miles away|29 min walk
Washington Ave @ River Rd
1.47 miles away|29 min walk
202 Orient Ave
1.48 miles away|29 min walk
Endicott Ave opp Bradstreet Ave
1.48 miles away|29 min walk
Boardman St @ Ashley St
1.51 miles away|29 min walk
171 Faywood Ave
1.52 miles away|30 min walk
160 Waldemar Ave
1.56 miles away|30 min walk
Beachmont
1.56 miles away|30 min walk
Beachmont - Bennington St @ Winthrop Ave
1.57 miles away|31 min walk
200 Endicott Ave
1.58 miles away|31 min walk
Washington Ave opp Veterans Rd
1.59 miles away|31 min walk
Veterans Rd @ Washington Ave
1.6 miles away|31 min walk
Beachmont - Winthrop Ave
1.6 miles away|31 min walk
Endicott Ave @ Waterview Ave
1.61 miles away|31 min walk
Beachmont - State Rd @ Winthrop Ave
1.61 miles away|31 min walk
Shirley St @ Washington Ave
1.61 miles away|31 min walk
Winthrop Ave @ Beachmont Station
1.62 miles away|31 min walk
220 Waldemar Ave
1.63 miles away|32 min walk
219 Faywood Ave
1.65 miles away|32 min walk
Bennington St @ Byron St
1.68 miles away|33 min walk
Endicott Ave @ Leverett Ave
1.69 miles away|33 min walk
Boardman St @ Leyden St
1.71 miles away|33 min walk
Endicott Ave @ Atlantic Ave
1.74 miles away|34 min walk
Shirley St opp Moore St
1.76 miles away|34 min walk
Shirley St @ Moore St
1.77 miles away|34 min walk
Shirley St opp Crystal Cove Ave
1.77 miles away|34 min walk
McClellan Highway @ Boardman St
1.77 miles away|34 min walk
Shirley St @ Crystal Cove Ave
1.79 miles away|35 min walk
Waldemar Ave @ McClellan Hwy
1.79 miles away|35 min walk
Tomasello Way
1.82 miles away|35 min walk
Bennington St @ Moore St
1.82 miles away|35 min walk
Winthrop Landing
1.83 miles away|36 min walk
McClellan Highway opp Tomasello Way
1.86 miles away|36 min walk
Winthrop Ferry Terminal
1.87 miles away|36 min walk
Burbank Hwy @ Suffolk Downs
1.87 miles away|36 min walk
560 Winthrop Ave
1.88 miles away|37 min walk
Opp 40 Burbank Hwy
1.93 miles away|37 min walk
McClellan Highway @ Addison St
1.95 miles away|38 min walk
Bennington St @ Harmony St
1.96 miles away|38 min walk
McClellan Highway opp Addison St
1.96 miles away|38 min walk
Bennington St @ Curtis St
1.97 miles away|38 min walk
Revere Beach Pkwy @ Campbell Ave
2.02 miles away|39 min walk
Bennington St @ Swift St
2.07 miles away|40 min walk
Shirley St @ Pontos St
2.12 miles away|41 min walk
Wood Island
2.12 miles away|41 min walk
Revere Beach Pkwy @ Woods Ave
2.13 miles away|41 min walk
230 Burbank Hwy
2.13 miles away|41 min walk
Chelsea St @ Curtis St
2.13 miles away|41 min walk
Shirley St opp Pontos St
2.13 miles away|41 min walk
Chelsea St opp Curtis St
2.14 miles away|42 min walk
Wood Island - Bennington St
2.14 miles away|42 min walk
Wood Island - Lovell St
2.15 miles away|42 min walk
Revere Beach Pkwy @ Pratt Pl
2.16 miles away|42 min walk
Terminal C - Departures Level
2.17 miles away|42 min walk
Terminal C - Arrivals Level
2.18 miles away|42 min walk
Shirley St @ Petrel St
2.18 miles away|42 min walk
Burbank Hwy @ Furlong Dr
2.19 miles away|42 min walk
Wood Island - Benningon St @ Wood Island Busway
2.2 miles away|43 min walk
Terminal E - Arrivals Level
2.21 miles away|43 min walk
Shirley St opp Yirrell Beach
2.22 miles away|43 min walk
Shirley St @ Yirrell Beach
2.23 miles away|43 min walk
Revere Beach Pkwy @ Hillside Ave
2.25 miles away|44 min walk
Bennington St @ Neptune Rd
2.29 miles away|44 min walk
Revere Beach Pkwy @ Green St
2.3 miles away|45 min walk
467 Chelsea St - Eagle Square
2.3 miles away|45 min walk
Chelsea St @ Eagle Sq
2.31 miles away|45 min walk
Eastern Avenue
2.32 miles away|45 min walk
Shirley St @ Bay View Ave
2.34 miles away|45 min walk
245 Central Ave
2.35 miles away|45 min walk
Central Ave @ Chelsea Garage
2.35 miles away|46 min walk
E Eagle St @ Chelsea St
2.37 miles away|46 min walk
Tafts Ave @ Shirley St
2.39 miles away|46 min walk
Bennington St @ Bremen St
2.41 miles away|47 min walk
Bennington St @ Chelsea St
2.45 miles away|47 min walk
Eagle St @ Lexington St
2.47 miles away|48 min walk
Terminal A
2.48 miles away|48 min walk
Terminal B Stop 2 - Arrivals Level
2.48 miles away|48 min walk
Tafts Ave @ Otis St
2.49 miles away|48 min walk
Boston-Logan Airport
2.49 miles away|48 min walk
Lexington St @ Shelby St
2.5 miles away|48 min walk
Central Ave @ Willow St
2.51 miles away|49 min walk
Revere Beach - Shirley Ave
2.51 miles away|49 min walk
Revere Beach
2.52 miles away|49 min walk
Winthrop Ave @ Revere Beach Pkway
2.52 miles away|49 min walk
Terminal B Stop 1 - Arrivals Level
2.53 miles away|49 min walk
Winthrop Ave @ Revere Beach Pkwy
2.54 miles away|49 min walk
Revere Beach - Ocean Ave Shirley Ave
2.56 miles away|50 min walk
Revere Beach - 300 Ocean Ave
2.57 miles away|50 min walk
Bennington St @ Prescott St
2.6 miles away|50 min walk
Winthrop Ave @ Elm St
2.61 miles away|51 min walk
Airport
2.62 miles away|51 min walk
Revere Beach - Beach St
2.62 miles away|51 min walk
Revere Beach - Beach St opp Kimball Ave
2.62 miles away|51 min walk
Winthrop Ave @ Victoria St
2.62 miles away|51 min walk
Revere Beach - Beach St @ Kimball Ave
2.63 miles away|51 min walk
Beach St @ N Shore Rd
2.63 miles away|51 min walk
Lexington St @ Prescott St
2.66 miles away|51 min walk
Beach St opp Nahant Ave
2.66 miles away|52 min walk
Airport - Buses Airport
2.69 miles away|52 min walk
Airport - Bremen St
2.7 miles away|52 min walk
Beach St @ Walnut Ave
2.71 miles away|52 min walk
The Neighborhood: Downtown Winthrop
Downtown Winthrop, a bustling hub in Suffolk County, offers an appealing blend of coastal charm and urban amenities. This district boasts scenic views of the Atlantic Ocean, perfect for outdoor enthusiasts. Residents and visitors can explore local parks, dine at diverse eateries, and enjoy a vibrant arts scene. The area is well-served by public transportation, with several bus routes and easy access to nearby transit stations, making commutes to Boston and surrounding areas convenient. Whether you're seeking culinary delights or a serene waterfront experience, this neighborhood delivers both with ease.
Demographics For all Downtown Winthrop listings
AVERAGE RESIDENT AGE
42 years old
AVERAGE HOUSEHOLD INCOME
$79,176/year
AVERAGE HOUSEHOLD COMPOSITION
2 People
What to know about Downtown Winthrop demographics:
- 31.57% of the population holds a high school diploma, indicative of a community with a focus on basic education.
- The average age of residents in Downtown Winthrop is 42 years, reflecting a well-rounded demographic mix.
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