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53 Trident Ave Unit 301, Winthrop
$365,000
2 Beds ⋅ 1 Baths ⋅ 73534695 MLS
Welcome to coastal living at its best. HOA FEE INCLUDES HEAT & HOT WATER! This top-floor corner 2-bedroom condo offers ocean views & an ideal vantage point overlooking the water, bringing in incredible natural light throughout. Hardwood floors run throughout the living area, while the kitchen features granite countertops, stainless steel appliances, & ample storage. Recent upgrades include appx. $10K in custom built-ins & thoughtfully designed closet systems to maximize storage & functionality throughout the home. The open living & dining space creates an inviting setting for everyday living or entertaining. Both bedrooms offer generous space, while in-unit laundry provides everyday convenience. Enjoy a professionally managed, well-maintained building with many recent improvements such as a new roof & whole building water heater/boiler. Deeded parking, large locked deeded storage unit, two bus lines incl. a stop at the top of the street w/ direct Blue Line access, ferry access, & walkable walkable restaurants complete this ideal coastal lifestyle

53 Trident Ave Unit 301, Winthrop

Listing courtesy of Listing Agent: Amanda Woodward from Listing Office: Coldwell Banker Realty - Boston.
66 Sunnyside Ave, Winthrop
$999,888
5 Beds ⋅ 2 Baths ⋅ 73529063 MLS
NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or savvy investors. Unit 1 rents for $3,100/mo and Unit 2 for $4,000/mo, generating $85,200 in gross annual income with a net of $76,900. Five bedrooms, two full baths, and a versatile layout ideal for extended families. The property features an enclosed porch, deck, fenced yard, professional landscaping, and individually metered electric. Minutes from downtown Boston via Rt. 1A. Don't miss this opportunity; schedule your private showing today!

66 Sunnyside Ave, Winthrop

Listing courtesy of Listing Agent: Mirna Monterrosa Orellana from Listing Office: COM-PRO Real Estate Services, Inc.
27 Billows St, Winthrop
$840,000
3 Beds ⋅ 3 Baths ⋅ 73526371 MLS
This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a renovated kitchen with white beadboard cabinetry, quartz countertops, subway tile backsplash, and stainless appliances. The entire 2nd floor is dedicated to a private primary retreat, complete with two closets and a private en suite with glass shower. The sun-filled sitting room connects the suite to the 2nd-floor deck where ocean views make for the perfect spot for morning coffee or evening entertaining. A wood spiral staircase leads to the third-floor bedrooms tucked under vaulted ceilings. Corner lot with 2 driveways & the opportunity to expand the yard practically on the water in Pt. Shirley!

27 Billows St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
800 Governors Dr Unit 6, Winthrop
$340,000
2 Beds ⋅ 1 Baths ⋅ 73525062 MLS
Bright and updated 2-bedroom condo at Governors Park featuring an open floor plan, renovated kitchen with granite countertops and stainless steel appliances, and spacious bedrooms with ample closet space. Professionally managed complex offers on-site laundry, swimming pool, tennis courts, and off-street parking. Conveniently located near public transportation, Winthrop Beach, shopping, dining, and just minutes to Boston and Logan Airport. Ideal for owner-occupants or investors seeking coastal living with city convenience.

800 Governors Dr Unit 6, Winthrop

Listing courtesy of Listing Agent: Fiorella Marte from Listing Office: Coldwell Banker Realty - Beverly.
50 Main St, Winthrop
$779,986
6 Beds ⋅ 2 Baths ⋅ 73523937 MLS
PRICE REDUCTION! Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!

50 Main St, Winthrop

Listing courtesy of Listing Agent: Matt Tasgin from Listing Office: United Brokers.
876 Shirley Street Unit 1, Winthrop
$799,999
4 Beds ⋅ 2 Baths ⋅ 73517107 MLS ⋅ ['Seabreeze Condominium'] BLDG.
Direct Ocean Front Living. Feel like you're on vacation every day! This spacious 2 level,7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day.Every day the the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master bedroom) the beautiful kitchen has cherry cabinets granite countertops, stainless appliances sliders to the large deck facing the sandy yard and Beach. This is one of a kind and Direct Ocean front living. All the rooms are large with plenty of character. Walk in closets and Laundry room make this for easy living. Bus line to the Blue line and Water shuttle into Boston is just a couple minutes away at the landing next to Winthrop yacht club. Marinas, shops and restaurants add to this great community. Don't miss out on this Opportunity to live Directly on a beach

876 Shirley Street Unit 1, Winthrop

Listing courtesy of Listing Agent: James Iannuzzi from Listing Office: Amo Realty - Boston City Properties.
43 Loring Rd, Winthrop
$919,900
3 Beds ⋅ 2 Baths ⋅ 73513222 MLS
Single Home, Great Location Great Shape Ready to Move In.

43 Loring Rd, Winthrop

Listing courtesy of Listing Agent: Jason Saphire from Listing Office: www.HomeZu.com.
142 Pleasant Street Unit 12, Winthrop
$585,000
2 Beds ⋅ 2 Baths ⋅ 73511795 MLS ⋅ ['Belle Mer'] BLDG.
Belle Mer is a Professionally managed boutique association. 15 of 16 units are owner occupied. Newer built condominium with 2 living levels in highly desired Winthrop Center location. Kitchen equipped with classic white shaker cabinetry, stainless Bosch appliances, wine cooler, + wonderful island to gather for enjoyment. Harbor views from main bedroom, inviting window seats, generous closet space. Lofty ceiling height thru out + abundant wall space for decorative art. 2 pets are welcomed. 1 assigned parking space plus 5 guest parking spaces. Washer and dryer near bedrooms. Bathrooms boast timeless designer tile. Ideal access into condo via front and back PRIVATE entries. Cetral air. Fireplace Surrounded by natural beauty, a wonderful variety of cafes and eateries, yoga studios, farmers market, and ez access to Boston and all points north and south This modern 2 bedroom, 2 bath condo on 2 levels is ideal starter home or great option for downsizing. Logan airport nearby. Boaters paradise. 5 pickleball courts close by. Control your own heat. Navien water tank,

142 Pleasant Street Unit 12, Winthrop

Listing courtesy of Listing Agent: Stacey Steck from Listing Office: Gibson Sotheby's International Realty.
51 Undine Ave, Winthrop
$659,900
3 Beds ⋅ 1 Baths ⋅ 73509184 MLS
Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you’ll find newer flooring, fresh interior paint, updated lighting, and a beautifully remodeled kitchen complete with stainless steel appliances. The home also features an updated bathroom, newer windows, and exterior doors throughout. The first floor boasts an open and versatile layout with a modern kitchen, spacious living and dining areas, and a bedroom currently being used a home office—all enhanced by water views. Upstairs, you’ll find two well-appointed bedrooms and a full bathroom. Conveniently located near public transportation, including bus routes with direct access to the MBTA.

51 Undine Ave, Winthrop

Listing courtesy of Listing Agent: The Caceda Team from Listing Office: Coldwell Banker Realty - Lynnfield.
7 Willis Ave, Winthrop
$849,900
4 Beds ⋅ 3 Baths ⋅ 73508827 MLS
Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stainless Steel Induction Wall Microwave & Wall Oven.Top of the line Stainless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors & Natural Woodwork Throughout. Crown Moldings & Chair Rails.Wood Fireplace in Living Room. There's a closet from the kitchen that was used as a staircase to the Basement that's finished with a huge full bath washer & dryer, Family Room & bedroom. That can be added in on the room count to 7 rooms 3 beds 2 full baths. 2nd floor 4 Large Rooms & 2 Bed.Plenty of Cabinet Space.Beautifull Hardwood Floors and All Natural Woodwork Throughout. Huge Living room. Dining Room has a spot for wall A/C. 4 Car Parking, Nice Huge Fenced in Yard with a Large Patio. Plenty of Parking Around The House Because of the corner Lot.5 year old roof. PROPERTY DELIVERED VACANT!

7 Willis Ave, Winthrop

Listing courtesy of Listing Agent: Phil Consolo from Listing Office: Century 21 North East.
10 Beach Rd Unit 1, Winthrop
$569,000
3 Beds ⋅ 1 Baths ⋅ 73497135 MLS
Just one block from Winthrop Beach, this spacious and inviting condo offers 1,377 SqFt of comfortable living. With 3 large bedrooms and 1 full bath, there’s plenty of room for working from home, entertaining, or simply relaxing.Step inside to discover an open-concept living and dining area that flows seamlessly into a large, modern kitchen, featuring gas cooking, ample counter space, and a dedicated laundry area with access to your private deck. Outdoors, you’ll enjoy multiple spaces to unwind — a fenced yard, a charming farmer’s porch, and a garden area that sets the home back beautifully from the street.Conveniently located on the first floor, this home makes carrying groceries a breeze and provides easy access to the common yard and an oversized basement with abundant storage. Recent updates include a new hot water tank (2022), boiler (2020), and front porch (2018).Experience the perfect blend of coastal living and city convenience, with the newly improved Winthrop beach.

10 Beach Rd Unit 1, Winthrop

Listing courtesy of Listing Agent: Rogelio Zuniga from Listing Office: United Brokers.
600 Shirley Unit 4, Winthrop
$384,888
1 Beds ⋅ 2 Baths ⋅ 73464942 MLS
8**Back on market due to out of state sale contingency falling through*** WELCOME TO WINTHROP BY THE SEA! THE COVE AT 600 SHIRLEY WAS CONVERTED IN 2022 AND IS LOCATED ON THE SITE OF THE HISTORIC CRYSTAL COVE HOTEL AND HAS AMAZING VIEWS OF BOSTON AND THE ATLANTIC OCEAN! WALK TO THE BEACH, THE YACHT CLUB, VARIOUS RESTAURANTS AND PARKS. THIS 1 BEDROOM UNIT FEATURES NOT ONE BUT TWO BATHROOMS AND 2 DEEDED PARKING SPOTS. ENJOY YOUR IN UNIT LAUNDRY AND EXCLUSIVE REAR PATIO ON WARM DAYS. JUST 5 MINUTES TO THE AIRPORT..GOOD INVESTMENT OR PERFECT FOR EMPTY NESTER OR TRAVEL BUG!

600 Shirley Unit 4, Winthrop

Listing courtesy of Listing Agent: Pratt Properties Team from Listing Office: Century 21 North East.

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