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119 Washington Ave, Winthrop
$1,995,000
5 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 73594447 MLS ⋅ 3,686 SqFt.
Truly exceptional waterfront Victorian, with glorious views of Crystal Cove and direct private access to Boston Harbor and beyond, is historic yet fresh, sophisticated yet wonderfully livable! Head out on your boat to explore beaches and islands, restaurants and bars, or relax and enjoy spectacular water views from almost every room. The bespoke water-facing chef's kitchen, with a welcoming island, bar sink and beverage fridge, coffee bar, and suite of Bosch appliances, is an inviting place to gather, cook and linger. Adjacent, the family room beckons, sliding doors bring the outdoors in, and connect to a deck just steps to your own beach. Natural light changes with the day and seasons; the moody grays of winter will be perfectly offset by a cozy fire in the open living room. Naturally there's a dining room, inviting guests for memorable celebrations, family gatherings, and holidays! Upstairs five thoughtfully located bedrooms are paired with more water views, a roof deck, and three tiled baths with elevated finishes. Charming original details go hand-in-hand with the 2026 updates, including ducted heating and cooling, highly efficient replacement windows, on-demand hot water, 400-amp electrical, hardwood flooring, new kitchen and baths, and more. Bonuses include a two car garage awaiting your roof deck and a clean, dry lower level media room w/ high ceilings and potential for expansion! Close to restaurants, Winthrop Yacht Club, Winthrop Golf Course, five minutes to the blue line, 10 minute drive to Logan Airport and Boston. Enjoy coastal living with easy city access! Anticipated completion by November 15th.

119 Washington Ave, Winthrop

104-106 Shirley St, Winthrop
$749,974
5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73592145 MLS ⋅ 2,520 SqFt.
Attention investors, builders, and contractors! A truly rare opportunity awaits at 104-106 Shirley Street, Winthrop. Situated on an impressive double lot spanning over 10,000 square feet, this property offers incredible upside and potential. The existing home features some fire damage, allowing buyers the flexibility to perform selective renovations, execute a partial demo, or complete a full renovation to suit their vision. Double lots of this footprint are nearly impossible to find in Winthrop, making it an ideal project for tradespeople, savvy investors and whoever looking to add substantial value. Located just minutes from beaches, shops, dining, transit, and a short commute into Boston and Logan Airport, the site and scale are exceptional. Property is being sold strictly in AS-IS, WHERE-IS condition with all faults. Seller or broker make no representations or warranties, express or implied. Buyer to perform all due diligence regarding condition, zoning, permits to able to build , and scope of work

104-106 Shirley St, Winthrop

91 Fremont St, Winthrop
$599,900
5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588699 MLS ⋅ 2,200 SqFt.
Two-Family Opportunity Near the Beach! Located in desirable Winthrop, this two-family property offers an exciting opportunity to build equity in a sought-after coastal community—all for under $600,000. This fixer-upper is ready for someone with vision to bring it back to life and unlock its full potential. Whether you’re an investor looking for your next project or a buyer willing to put in the time and effort to create value, this property offers plenty of possibilities. Enjoy the convenience of being close to the beach, local shops, restaurants, and transportation while taking advantage of the income potential and flexibility a two-family home provides. A great opportunity to renovate, customize, and create lasting value in Winthrop!

91 Fremont St, Winthrop

43 Dolphin Ave, Winthrop
$799,900
5 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73587974 MLS ⋅ 2,437 SqFt.
Charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. Perfect ADU potential or in-law space in the lovingly finished and conveniently laid out walk out lower level with an oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, a laundry area. Complete with a bedroom and a full sized cedar closet, this is the home for you! Walk out your lower level door to a covered area for a table or another sitting area. The outdoor shed has doors that open up to the pergola with a bar and tv so you can watch the games during your cookouts. Enjoy the convenience of three off-street parking spaces and easy access to Boston, Logan Airport, scenic waterfront trails, shopping, dining, and more. Don't miss it!

43 Dolphin Ave, Winthrop

174 Bartlett Road, Winthrop
$2,100,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73550891 MLS ⋅ 6,224 SqFt.
One of the most coveted locations in Winthrop, 174 Bartlett Rd is your dream costal retreat where luxury meets seaside living. Completely gut renovated, this exceptional home offers over 6,000 sq ft of beautifully designed living space across four expansive levels. The heart of the home is the stunning chefs kitchen with seamless oversized Brazilian Quartzite island surrounded by premium Sub-Zero, Wolf & Miele appliances, & a fully appointed entertaining bar. Anchored by a striking Valor fireplace, the two thoughtfully designed seating areas & expansive dining room create space for intimate or larger-scale entertaining. The Primary suite is a water view retreat with steam shower & BainUltra therapeutic soaking tub, dual walk-in closets, & private laundry. Welcome guests in the lower level suite, enjoy resort style yard with Gunite in-ground pool, basketball court & grilling island, or end days on the roof top deck with incredible views. This thoughtfully crafted home is unforgettable!

174 Bartlett Road, Winthrop

66 Sunnyside Ave, Winthrop
$999,888
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73529063 MLS ⋅ 2,635 SqFt.
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

426 Winthrop St, Winthrop
$749,900
5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 72784870 MLS ⋅ 2,394 SqFt.
Welcome home to this open concept colonial home in sought after Winthrop! The home offers gleaming hardwood floors with a sunken living room equipped with a surround sound system throughout. The personally crafted kitchen/dining area has beautiful maple cabinets & granite countertops. Entertain family and friends through elegant French doors leading to a to a large patio and with fenced yard with outdoor speakers. Also included on the main floor is a cozy family room, huge home office, and a half bath. The upper level boasts 4 large bedrooms, a full bathroom, a spacious master bedroom with its own huge walk-in closet and private en-suite bathroom. The third floor has a full walk-up to an attic offering lots of extra storage. The basement offers a game room, exercise room, workshop, and plenty of storage. Among many other features are two-zoned AC, tank-less water heater, newer roof, plumbing and electrical.

426 Winthrop St, Winthrop

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.

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