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$1,240,000
7 Beds ⋅ 4 Baths ⋅ 73475129 MLS
Well-located 4-family investment property in the heart of Winthrop’s Cottage Hill neighborhood. 10–12 Charles Street offers four separately metered units totaling 3,688 square feet on a 6,127 sq ft lot, with strong in-place income and upside. The unit mix consists of two larger units and two one-bedroom units, appealing to both long-term renters and owner-occupants seeking supplemental income. Current rents total approximately $8,550 per month, with additional room for optimization over time. The property features off-street parking for six vehicles, a major value driver in this coastal submarket, along with a full unfinished basement ideal for storage and future improvements. Several units have been refreshed, providing a solid balance of immediate cash flow and long-term capital improvement potential. Located just blocks from the ocean, public transportation, schools, and Winthrop Center amenities, this asset benefits from strong rental demand driven by proximity to Boston & Logan.

10-12 Charles St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$1,065,000
4 Beds ⋅ 3 Baths ⋅ 73443354 MLS
The street name; 'Harbor View Ave" says it all! Sweeping unobstructed views of the open ocean, Boston Harbor, & city skyline! Nestled atop one of Winthrop’s highest elevations, delivering a rare combination of breathtaking coastal scenery & beach access. This sun-drenched 3 unit home offers 4 bedrooms, 3 full baths, garage parking, making it ideal for homeowners, developers, or investors. From every room, take in panoramic ocean views, watch the sunrise over the Atlantic, ships in the harbor, and the Boston skyline glittering at night. Just feet away, public stairs directly to Yirrell Beach. At the end of the street, Winthrop Yacht Club offers even more coastal lifestyle perks. Whether you choose to expand, develop, or convert to condos (buyer to perform their own due diligence), this property offers unmatched value and vision. Elevated above flood zone, you'll enjoy peace of mind with views that rival any along the New England coast—all just minutes from Boston!

41 Harbor View Ave, Winthrop

Listing courtesy of Listing Agent: Brian Perrin from Listing Office: Brian J. Perrin Real Estate.
$875,000
4 Beds ⋅ 2 Baths ⋅ 73550227 MLS
If you've been waiting for the perfect opportunity to live near the ocean - this is it! Located between Winthrop Harbor and Winthrop Beach, with literal steps to the ocean in either direction, this beautiful, completely renovated single family home offers 4 bedrooms, 2 baths, an updated kitchen, hardwood floors, central air and much more! Great back yard, off-street parking and a beautiful wrap-around front porch with water views that New Englanders dream of. Incredible location - just steps to Winthrop Beach and Winthrop Landing with water ferry access to Downtown Boston. Close to restaurants, parks, shops, multiple yacht clubs, public transportation and much more. Minutes to Boston, Logan Airport and points north. Don't miss this amazing opportunity to find your seaside home this summer.

69 Crystal Cove Avenue, Winthrop

Listing courtesy of Listing Agent: Edward Deveau from Listing Office: Century 21 Mario Real Estate.
$775,000
3 Beds ⋅ 3 Baths ⋅ 73406111 MLS
Ideally located just steps from the Winthrop Yacht Club, The Landing, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace wrapped in lava-rock, plus two additional rooms perfect for a family room, guest room, or home office. The updated eat-in kitchen includes a convenient half bath with in-unit laundry and plenty of cabinet space with a Wolf Cooktop, Miele dishwasher and newer range. The upstairs offers three spacious bedrooms including an expansive oversized primary bedroom and a large full bath. The basement has an additional full bathroom, ample storage, and opportunity for future equity plays or extra rooms. 100 Cottage has a brand new 200 amp electrical service, new panel, and the perfect floor plan and is only 20 minutes to Seaport, less by ferry.

100 Cottage Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$585,000
3 Beds ⋅ 2 Baths ⋅ 73428498 MLS
Live by the water and soak in ocean, harbor, and Boston skyline views from this renovated 3-bed, 1.5-bath condo on Cottage Hill! Spanning the full second floor with 1,165 sf, this sunlit home features double bay windows, hardwood floors, and an open layout for easy living and entertaining. The updated kitchen boasts gas cooking, granite counters, and stainless appliances. Enjoy central AC, in-unit laundry, private basement storage, and a pet-friendly association with low HOA fees. Relax on your private deck, grill in the shared yard, and take advantage of nearby beaches, restaurants, shops, and the water shuttle. Easy on-street parking. Come see the views and this beautiful home at the open house 9/13–9/14.

42 Harborview Ave Unit 2, Winthrop

Listing courtesy of Listing Agent: Randall Horn from Listing Office: Entourage Realty LLC.

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