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40 Cottage Park Rd, Winthrop
$950,000
5 Beds ⋅ 3 Baths ⋅ 73437527 MLS
Nestled in the sought-after Cottage Park neighborhood, this beautifully maintained two-family home offers over 2,400 sq ft of living space, a garage plus 3 off-street parking spaces, and is being delivered vacant—perfect for owner-occupants or investors. Unit 1 features 2 bedrooms, a sunroom, and classic wood floors. Unit 2 spans two levels with 3 bedrooms, 2 full baths, central air, and a family room for flexible living. Enjoy your deck or your private yard with a jacuzzi, just minutes from Winthrop’s beaches, marina, parks, and vibrant downtown. The basement features higher ceilings, currently set up with a sauna and home gym and 2 sets of laundry for owners and tenants alike. With projected income around $70,800 annually, this turnkey opportunity blends seaside living and smart investment potential.

40 Cottage Park Rd, Winthrop

Listing courtesy of Listing Agent: The Reference Group from Listing Office: Reference Real Estate.
339 Winthrop St, Winthrop
$910,000
5 Beds ⋅ 3 Baths ⋅ 73441636 MLS
This beautifully maintained two-family home offers the perfect blend of meticulous care, charm and city convenience. Just minutes from downtown Boston and Logan Airport, enjoy easy commuting paired with the tranquility of a vibrant beachside community. Nearly 4,000 sq. ft. of living space features hardwood floors, a custom kitchen with island, gas fireplace, and a flexible floor plan with home office or first-floor bedroom. Upstairs offers two bedrooms, laundry, and a finished walk-up attic —ideal as a private suite or playroom. The lower-level unit includes a separate entrance, kitchenette, bedroom, bath and private laundry—perfect for in-law, au pair, or guests. Outside, enjoy a private fenced yard with hardscaping, raised garden beds, and a large shed. Updated systems, newer roof, siding, and windows ensure low-maintenance living. Walk to the beach, harbor, and local cafés—lifestyle, location, and value in one of Greater Boston’s most desirable coastal towns!

339 Winthrop St, Winthrop

Listing courtesy of Listing Agent: Danielle McCarthy from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
126 Brookfield, Winthrop
$900,000
4 Beds ⋅ 3 Baths ⋅ 73542949 MLS
Two-family home in a prime Winthrop location, directly across from Ingleside Park and minutes from Winthrop Center. Each unit offers 2 bedrooms, 1 full bath, a bright living room, eat-in kitchen, and private porch. Set on a 0.14-acre lot, the property features a partially fenced backyard—ideal for entertaining, gardening, grilling, or relaxing. The lower level, accessible via a private rear entrance, offers excellent potential for flexible use such as a recreation area, home office, gym, workshop, or storage. Recent updates include a roof replacement in 2021. Just a short stroll to Winthrop Center shops and restaurants, and to Donovan Beach, with bus service connecting to the Blue Line and approximately a 30-minute door-to-door commute to Boston via public transit. Whether you're an owner-occupant looking to live in one unit and offset your mortgage with rental income, or an investor seeking rental income in a desirable coastal location, this is an opportunity you won't want to miss.

126 Brookfield, Winthrop

Listing courtesy of Listing Agent: Marissa Amin from Listing Office: Amo Realty - Boston City Properties.
44 Cottage Park Rd, Winthrop
$900,000
6 Beds ⋅ 2 Baths ⋅ 73525592 MLS
Discover the potential of multi-family living located in the sought after Cottage Park area, conveniently located close to downtown, near beaches, restaurants, and public transportation. Flexible layout with excellent opportunity to personalize or add value. This spacious two-family home offers strong potential for owner occupants, investors, or extended living arrangements. Live in one unit and rent the other. Unit 1 offer's 2 bedrooms,1-bathroom, large Livingroom, dining room and laundry in the basement. Unit 2 offers a spacious layout, total of 4 bedrooms, 2 bedrooms on the 2nd floor and 2 bedrooms on the 3rd floor,1 bathroom and in unit laundry. Don't miss this great opportunity.

44 Cottage Park Rd, Winthrop

Listing courtesy of Listing Agent: William McLaughlin from Listing Office: Cameron Prestige, LLC.
44 Birch Road, Winthrop
$900,000
3 Beds ⋅ 2 Baths ⋅ 73432055 MLS
Borrowing inspiration from Nantucket and Martha's Vineyard, this single family home in the seaside town of Winthrop is a classic coastal New England residence. Recently renovated, this three bedroom, two bath home is impeccably designed; from the fireplace that first greets you in the living room to the soaking tub in the spa-like bathroom. An overly spacious kitchen with quartz countertops and stainless steel appliances lends itself to great times cooking and entertaining with friends and family; and the primary bedroom suite is the perfect cozy retreat. Located in the desirable "Maze' area, this home is close to several beaches, quaint shops and restaurants in Winthrop's Center and just minutes to Downtown Boston by car, public transportation or ever popular water ferry. A two-car detached garage, large basement, spacious backyard and professional landscaping round out some of the appealing features. This home is move-in ready and perfect for nearly every buyer. Don't Miss Out.

44 Birch Road, Winthrop

Listing courtesy of Listing Agent: Edward Deveau from Listing Office: Century 21 Mario Real Estate.
41 Summit Ave, Winthrop
$890,000
4 Beds ⋅ 2 Baths ⋅ 73451267 MLS
Lovely custom built ranch offering endless possibilities! Perfect for multi-generational living or added income with a fully equipped lower level apartment. The main floor features a cherry wood kitchen with granite countertops, a spacious fireplace living room, tiled bath with separate shower and tub, generous bedrooms, den, and a bright sunroom with ocean views. Enjoy central air and an attached garage. The lower level includes a kitchen, family room with sliders to a private yard and in-ground pool, two bedrooms, and a bath. Garage and mudroom could be converted into an ideal ADU for extra income or extended family. Fantastic location public transportation at one end of the street and beach access at the other!

41 Summit Ave, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.
2 Deane Ave, Winthrop
$884,000
5 Beds ⋅ 3 Baths ⋅ 73429466 MLS
Charm & Convenience & Income! Exciting opportunity to own a home w/approved inlaw-ADU/au-pair within walking distance to the ocean! Enjoy views of Boston skyline! Perfect for multi-generation living. Located in Winthrop Highlands this home has been renovated on 4 levels. Natural light pours into every room. The front hall embraces details from its period. First floor features a custom kitchen quipped w/oversized island, ample cabinetry, SS appliances and granite counters. Large living room leads to dining rm making perfect entertainment space. Heated entry rm w/gas vented stove is perfect for mudroom or reading rm while enjoying hardscape. Half bath w/laundry. 2nd Floor has den, 2-3 large bedrms and renovated custom bathroom w/tile shower and radiant heated floors. Walk up to 3rd level for XL bedroom w/views of Boston.In-law/ADU has separate entry. New multi-level patio is an oasis. California closets. Close to beach, highway, bus, shopping and restaurants. ~$480K in recent updates

2 Deane Ave, Winthrop

Listing courtesy of Listing Agent: Marina Tramontozzi from Listing Office: True North Realty.
80 Shirley St, Winthrop
$880,000
4 Beds ⋅ 2 Baths ⋅ 73376243 MLS
Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchens and natural light throughout. Some of the sunniest units you will see. Bathrooms like spas. High ceilings and great flowing layouts that make sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heating systems, central A/C, upgraded plumbing and electrical. All the charm of a Victorian home w modern amenities. This elegant home is sure to turn heads with an aura of style and sophistication. Truly a special place that is not to be missed!

80 Shirley St, Winthrop

Listing courtesy of Listing Agent: Nick Burnes from Listing Office: Red Tree Real Estate.
211 Grovers Ave, Winthrop
$877,700
3 Beds ⋅ 3 Baths ⋅ 73552912 MLS
Location, location, location! Welcome to 211 Grovers Avenue, perfectly situated in the highly sought-after ocean community of Winthrop Highlands. This iconic brick-front Cape Cod sits on a 5,227 sq. ft. lot and radiates timeless character. Inside, you'll find an inviting living room featuring elegant tray ceilings and a warm fireplace. The home offers 3 bedrooms and 2.5 bathrooms, with incredible potential for expansion—the finished basement could easily become a teen suite, family room, or even an income-generating apartment. Outside, enjoy the coastal lifestyle with a great back deck, an attached garage, and a driveway, all just steps from the ocean. PRIVATE SHOWINGS START 8/7 through 8/9 PLEASE TEXT OR EMAIL LISTING AGENT

211 Grovers Ave, Winthrop

Listing courtesy of Listing Agent: Concetta Cicolini from Listing Office: Lamacchia Realty, Inc..
69 Crystal Cove Avenue, Winthrop
$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.
123 Hermon St, Winthrop
$875,000
4 Beds ⋅ 2 Baths ⋅ 73442302 MLS
Well maintained spacious two family in a prime location. Both apartments are 1,486 sf and have open floor plans, wood flooring and high ceilings. Unit 1 has a great eat in kitchen with washer and dryer area in the hallway. Bedrooms are good size with double closets. There is a seamless flow from the front door to the open living / dining room. This unit offers easy access to the yard and the 1,486-sf unfinished basement. Unit 2 has a similar open floor plan. Large eat in kitchen with pantry. This unit has a stairway to a high ceiling 1,382-sf unfinished attic. There is a closed in unheated porch off the back with an additional stairway to the attic. Move in ready with room to expand. Sunny corner lot, partially fenced, 3 car off-street parking. Roof is about 6 years old. Close to public transportation and downtown. See attachments for more info. Show daily Until 5:00 PM.

123 Hermon St, Winthrop

Listing courtesy of Listing Agent: Valerie Lane from Listing Office: Brad Hutchinson Real Estate.
18-20 Fairview Steet, Winthrop
$855,000
5 Beds ⋅ 3 Baths ⋅ 73537768 MLS
Rare opportunity to own a legal 2 family with an inlaw apartment in one of Winthrop's most desirable locations! Completely vacant and ready for its next owner, this brick-front property offers tremendous potential for investors, owner-occupants, or multigenerational living. No flood insurance required. The spacious owner's unit lives like a single-family home, featuring 7 rooms, 3 bedrooms, a sunroom, office, dining room, deck, and a dramatic sunken living room with fireplace. Additional 2-room apartment & in-law apt provide excellent income potential. Set on a beautiful, generously sized lot with a heated 2-car garage, this property is ready for your vision and updates. Enjoy all that Winthrop has to offer—beautiful beaches, scenic waterfront walks, outstanding restaurants, local shops, and a welcoming small-town atmosphere—just minutes to the MBTA, Logan Airport, Boston, and major routes north and south.

18-20 Fairview Steet, Winthrop

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.
550 Pleasant St Unit 506, Winthrop
$855,000
2 Beds ⋅ 2 Baths ⋅ 73456380 MLS ⋅ ['The Residences At Atlantis Marina'] BLDG.
Penthouse Waterfront Luxury at Atlantis Marina – Oversized Boat Slip Included!Experience sophisticated coastal living in this stunning top-floor corner penthouse at Atlantis Marina, offering sweeping water views and panoramic Boston skyline vistas. This rare fifth-floor residence combines luxury, space, and an unbeatable location in the charming seaside town of Winthrop.This exceptional 2-bedroom, 2-bath home features an open-concept layout perfect for entertaining, complete with private deck overlooking the marina and city. Gourmet kitchen with stainless steel appliances, gas cooking, stone counters, and an oversized refrigerator. Gas fireplace, recessed lighting, and abundant natural light.In-unit washer/dryer and central heat/air conditioning. A highlight of this residence is the assigned large boat slip lease ideal for boating enthusiasts and available for use with a small yearly maintenance fee. Located just minutes from downtown Boston.This is coastal living at its finest

550 Pleasant St Unit 506, Winthrop

Listing courtesy of Listing Agent: Jessica Pumphret from Listing Office: Blue Sky Realty.
56 Main Street, Winthrop
$850,000
4 Beds ⋅ 2 Baths ⋅ 73460239 MLS
OPPORTUNITY KNOCKS.......Two family with large yard is located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 2001. The owner's unit is on the second and third floors with an open floor plan and lots of natural lighting. It contains a living room, dining area, kitchen, bath and one bedroom. The top floor consists of a sprawling main bedroom large enough to become 2 rooms. There are Boston skyline and marina views from the the top floor. The owner's unit has a great layout and good size rooms with lots of windows and laundry area of the kitchen. The first floor unit consists of a living room, kitchen, bath and two bedrooms. THIS IS A GREAT OWNER OCCUPY OR, INVESTMENT PROPERTY!

56 Main Street, Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
3 Seal Harbor Rd Unit 736, Winthrop
$850,000
3 Beds ⋅ 3 Baths ⋅ 73452959 MLS ⋅ ['Seal Harbor Condominiums'] BLDG.
Rare opportunity at the coveted Seal Harbor Condominiums! This stunning 3-bed, 2.5 bath single-level residence on the 7th floor offers breathtaking waterfront views from your private balcony—perfect for morning coffee or sunset cocktails. Enjoy a beautifully updated kitchen with modern finishes, spacious bedrooms filled with natural light, and a serene primary suite featuring a spacious closet and spa-like shower. Two conveniently located garage spots provide easy access to the elevator, making everyday living effortless. Experience resort-style luxury with 24/7 concierge service, indoor and outdoor pools, fitness center, sauna, hot tub, and elegant shared entertainment spaces. Located in a highly desirable coastal area, just moments from pristine beaches, scenic walking paths, and local dining, this exceptional home combines comfort, style, and convenience in one of the most sought-after waterfront communities on the North Shore.

3 Seal Harbor Rd Unit 736, Winthrop

Listing courtesy of Listing Agent: Candice Pagliarulo Hodgson from Listing Office: Lyv Realty.
19 Moore St, Winthrop
$844,000
5 Beds ⋅ 3 Baths ⋅ 73484508 MLS
Rare opportunity just one street from the beach, offering strong rental income potential ideal for investors and owner-occupants alike. This well-maintained two-family offers a flexible layout with a 2-bedroom 1st floor unit and a spacious second unit with 3 bedrooms & 1.5 baths across two levels. The second unit is currently rented for $3,650/month, providing immediate income, while the 1st floor unit is vacant & ready for an owner-occupant or new tenant. Both units feature hardwood floors and fresh interior paint. Unit 1 includes a decorative fireplace in the living room, while Unit 2 offers in-unit laundry & a well-maintained kitchen. Major updates include a 2020 roof, 2024 water heater, and 2024 boilers with separate gas heating systems. Basement space offers additional storage, plus a rear porch and low-maintenance yard. Ideally located one street from the beach with easy access to Boston via ferry, bus, and MBTA, & close to restaurants and marinas. Schedule a showing today

19 Moore St, Winthrop

Listing courtesy of Listing Agent: Kevin Ochoa from Listing Office: United Brokers.
54 Villa Ave Unit 2, Winthrop
$839,900
3 Beds ⋅ 3 Baths ⋅ 73410073 MLS
Modern 2019 move-in ready townhouse with coastal charm! This meticulously crafted 3-bedroom, 2.5-bathroom home brimming with natural light and coastal charm with features such as soaring ceilings, walls of windows, and an open floor plan. Key Features: • Statement gas fireplace as living room focal point • Designer kitchen with premium appliances • Private backyard with dedicated driveway parking • Spectacular rooftop terrace off primary suite • Custom millwork and designer lighting throughout Dual Outdoor Spaces: Private backyard for relaxing plus exclusive rooftop terrace with sweeping views—perfect for entertaining or peaceful mornings above it all. Prime Location: Easy access to downtown Boston and Logan Airport, with Winthrop ferry providing scenic transportation. The best of both worlds—coastal community living just minutes from the city. Rare combination of modern amenities, outdoor space, and prime location!

54 Villa Ave Unit 2, Winthrop

Listing courtesy of Listing Agent: The Reference Group from Listing Office: Reference Real Estate.
37 Loring Rd., Winthrop
$837,500
3 Beds ⋅ 3 Baths ⋅ 73546996 MLS
PRIDE OF OWNERSHIP CAN BE YOURS.......METICULOUSLY CARED FOR AND READY FOR THE NEW OWNERS! Located in one of Winthrop's most desirable areas, this Center Entrance Colonial has Harwood oak floors and a bath on every level. A huge fireplaced living room, eat in kitchen with a slider and deck overlooking the enormous (pool size) yard with a garden area and lots of off street parking. The second level has 3 bedrooms and a full bath and laundry. The Main bedroom is King-sized! The Bonus Room in the basement is multi purposed and easily works for extended family ( IN-LAW POTENTIAL) with another full bath, exrta high ceilings, open floor plan and a direct walk out to the yard. Another separate basement area is a handy workshop/storage area. THIS COULD BE THE ONE! In Winthrop by the Sea boasting 2 beaches, new schools, 3 Yacht Clubs, a nine hole golf course and lots of Great Restaurants!

37 Loring Rd., Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
143 Morton St, Winthrop
$835,000
4 Beds ⋅ 3 Baths ⋅ 73530429 MLS
Spacious 4-bed, 2.5-bath single-family home in Winthrop—where coastal living meets effortless access to Boston. Set near Belle Isle Marsh, enjoy kayaking in calm waters, nearby ocean beaches, yacht clubs, and a scenic seaside golf course—all part of Winthrop’s rare small-town feel. Easy access to the major route in town means smoother, lower-traffic commutes in and out of the city. Inside, sun-filled living areas, a bright kitchen, a separate bonus family room, and a finished lower level with bar and fireplace offer flexible space for entertaining and everyday living. A large fenced yard adds privacy and room to relax, while owned solar panels provide energy efficiency and long-term savings. A standout opportunity combining lifestyle, convenience, and value.

143 Morton St, Winthrop

Listing courtesy of Listing Agent: Alla Rossi from Listing Office: Coldwell Banker Realty - Boston.
108 Winthrop St, Winthrop
$835,000
5 Beds ⋅ 3 Baths ⋅ 73500423 MLS
Spacious 5-bedroom, 3-bathroom Craftsman bungalow on a corner lot just moments from Winthrop Center. Timeless Craftsman details include beautifully crafted built-in wood storage, adding warmth, character, and functionality. Oversized windows throughout fill the home with natural light. The top floor features a private primary suite with two walk-in closets and a dedicated makeup room. The first floor includes a kitchen, living room, dining room, two bedrooms, and a home office, offering an ideal layout for everyday living and entertaining. The finished basement adds two additional bedrooms and a large bonus room perfect for a playroom, office, or extra bedroom. A full bathroom on each level adds convenience. Additional highlights include central air and a newer roof. Not located in a flood zone. Rare opportunity to enjoy small-town coastal living just minutes from Boston.

108 Winthrop St, Winthrop

Listing courtesy of Listing Agent: Mark Mulkerrin from Listing Office: Coldwell Banker Realty - Sharon.
89-91 Sagamore Ave, Winthrop
$830,000
4 Beds ⋅ 3 Baths ⋅ 73426322 MLS
Welcome to this well-maintained 2-family property located in the desirable Lower Highlands neighborhood of Winthrop by the Sea. This home is just a short stroll to the beach, shops and local dining! Perfect for homeowners seeking rental income or investors alike! The main unit features 3 bedrooms, 1 bathroom, and a bright, open, inviting living area. A finished family room and half bath on the lower level provide additional space for entertaining, relaxing, or working from home.The second unit, conveniently located on the lower level, offers 1 bedroom and 1 full bath, ideal for extended family, guests, or rental opportunities. Enjoy outdoor living with a large front deck perfect for entertaining and a private, fenced-in yard. Whether you’re looking for a home with income potential or a multi-generational living option, this property combines comfort, location, and charm – all just steps from Winthrop’s beautiful shoreline. Enjoy all that Winthrop by the Sea has to offer!

89-91 Sagamore Ave, Winthrop

Listing courtesy of Listing Agent: Christine D'Ambrosio from Listing Office: Lantern Residential.
70 Moore St Unit PH, Winthrop
$825,000
3 Beds ⋅ 2 Baths ⋅ 73525692 MLS
Set on coveted Winthrop Shore Drive, this meticulously maintained penthouse presents an opportunity for elevated, uncomplicated beachside living with breathtaking ocean views from nearly every window. The expansive one-level layout with 1,736 SF of polished living space offers flow and function, comprising three spacious bedrooms, two full baths, 360 degree exposure, three distinct living areas and a bonus office. Highlights include the wall of Atlantic-facing windows enclosing the open living-dining areas, a turret-like primary suite with oversized bath and the view from the roof, where the deck of your dreams could overlook both the ocean and Boston's skyline. Even while immersed in natural beauty, residents enjoy every comfort & convenience: central AC, recessed lighting, high ceilings, premium appliances, stylish finishes, smart home features, in-unit laundry and easy access parking. Built in 2015, this beloved 3-unit building in A+ location also has extra storage and roof rights.

70 Moore St Unit PH, Winthrop

Listing courtesy of Listing Agent: Cassie Comstock from Listing Office: Compass.
105 Circuit Road, Winthrop
$825,000
5 Beds ⋅ 3 Baths ⋅ 73438926 MLS
This is your PERFECT OPPORTUNITY to purchase a traditional Whittemore style home in Winthrop's highly sought-after Maze neighborhood to make your own. This charming, OVERSIZED single family home offers plenty of room for everyone with FIVE (5) bedrooms (including top floor primary that could be turned into a suite) 2.5 baths and a fully finished basement with separate walkout. Available for the first time in three decades, this home could use a refresh and some personal touches to make it yours, but well worth the effort and equity! The living and dining room lend itself to a classic New England design, complete with hardwood flooring, bay windows and impeccable period charm. Situated on a 5,000+ square foot lot and offering a spacious back yard, with plenty of room to add a pool! Ample off-street parking in the driveway. Conveniently located close to public transportation, multiple beaches, shops, popular restaurants and more! Minutes to Downtown Boston, Logan Airport & Points North

105 Circuit Road, Winthrop

Listing courtesy of Listing Agent: Edward Deveau from Listing Office: Century 21 Mario Real Estate.
993 Shirley St, Winthrop
$815,000
5 Beds ⋅ 4 Baths ⋅ 73466654 MLS
Located in Winthrop’s highly desirable Point Shirley, this renovated single-family home offers generous living space, a flexible layout, and an unbeatable beachside location while still close to Boston & everyday conveniences.The main level features a renovated open floor plan with hardwood floors & tons of natural light, where living & dining flow seamlessly into a spacious, remodeled kitchen with granite countertops, upgraded cabinetry, stainless steel appliances, recessed lighting, shiplap details & a breakfast bar, perfect for everyday living or entertaining.Two bedrooms on the first floor offer added convenience, including a main bedroom with an en-suite full bath. Upstairs, you’ll find additional bedrooms & bathrooms, offering plenty of flexibility for home offices, guest rooms, or growing households, all featuring hdwd floors, natural lighting & ceiling fans. Enjoy Atlantic views, walks to the beach, off street parking & easy access to local amenities in this move-in-ready home.

993 Shirley St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
45 Read Street, Winthrop
$815,000
4 Beds ⋅ 2 Baths ⋅ 73464677 MLS
Welcome to Winthrop this beautiful classic colonial awaits you! This lovingly cared for home has been with one family for the last 29 years and is perfect for the extended family. The original home built in 1920 includes a newer two story addition offering lots of living space. The extra large eat in kitchen was completely remodeled in 2021 and features beautiful white cabinetry, stainless steel appliances and quartz counter tops perfect for all your family gatherings. There are 4 plus big bedrooms with lots of closet space & 2 full baths. There are formal living & dining rooms both with hard wood flooring, a family room, separate first floor laundry room, beautiful entry way, and lots of natural light. There is also a large full unfinished basement with endless possibilities. Outside is a deck, large fenced in yard, and plenty of parking, all situated on a large lot. Come view this home today!

45 Read Street, Winthrop

Listing courtesy of Listing Agent: William Stewart from Listing Office: Sgarzi & Stewart Real Estate, LLC.
380 Pleasant St, Winthrop
$790,000
3 Beds ⋅ 2 Baths ⋅ 73438349 MLS
Spacious Home with Water Views located at the entrance of the Desirable “Maze Area”. Welcome to this large & inviting home located steps from Donovan Beach & Ingleside Park. With beautiful water views and an abundance of living space, this property offers the perfect blend of comfort, convenience and coastal charm. Step inside the welcoming foyer, which flows into a sun-filled open living room and dining room. The spacious kitchen features quartz counters, SS appliances and generous cabinet space and opens directly to the back deck-ideal for entertaining or relaxing by the water breeze. A well designed full bath completes the first floor. On the second floor you’ll find 3 generous size bedrooms with ample closet space, bonus/office area with a full bathroom & balcony. The third floor provides even more flexibility with more bonus space great for teen suite, office or guest bedroom while enjoying sweeping water views. Located in a prime Winthrop setting, this is a must see! OH Sat & Sun

380 Pleasant St, Winthrop

Listing courtesy of Listing Agent: Colleen Eddy from Listing Office: Return Realty Group, Inc..
62 Lowell Road, Winthrop
$780,000
5 Beds ⋅ 3 Baths ⋅ 73432635 MLS
Welcome to the "Maze!" This Whittemore designed home is solidly built & filled with character & charm. With great bones & endless potential, this 4+ bedroom, 2.5 bath single is the perfect canvas to create space you've been dreaming of, all in one of Winthrop's most sought after locations. Some of the wonderful features include recently refinished hardwood floors, a wood-burning fireplace, eat in kitchen w/1/2 bath & french doors leading to a first floor home office. There are four bedrooms on the second floor & a full bath with loads of storage. Do you desire more space? Up to the third floor, you'll find another bedroom and a spacious unfinished room. The partially finished basement expands your living space with a family room, 3/4 bathroom, updated utilities along with a washer and dryer. Off street parking for four cars, one car garage and a partially fenced in yard. Centrally located, schools, shopping, bus to Blue Line, seasonal Ferry to Logan-Boston are all close

62 Lowell Road, Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.
32 Hale Avenue, Winthrop
$777,000
3 Beds ⋅ 2 Baths ⋅ 73390649 MLS
A spectacular hilltop home with unmatched 360° views. A once-in-a-lifetime opportunity to own this exceptional hilltop property offering panoramic views of the Atlantic Ocean, Boston Harbor, Winthrop Harbor, and the Boston skyline. Ocean views from every room and all three decks make this home truly one of a kind. Steeped in history, this site was purposely chosen by Patriot troops during the Revolutionary War as a fortification point to best view the British Ships in the ocean and Boston Harbor—commemorated today by a historic marker at the front of the property. Fully updated and move-in ready. This home on a private dead end street features: a spacious main suite with private bath, sweeping ocean views, an octagon lookout room, an upper top deck with breathtaking 360° vistas, an outside shower for beachgoers. A very short walk to Yirrell Beach, Deer Island State Park, and Coughlin Playground. This is a rare chance to own a scenic and historic gem. Schedule your private showing today

32 Hale Avenue, Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
1001 Shirley St Unit 3, Winthrop
$775,000
2 Beds ⋅ 3 Baths ⋅ 73573609 MLS ⋅ ['The Pearl'] BLDG.
Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Special developer pricing now offered at 775,000 Seller reserves the right to accept, reject, or counter any offer and may request highest and best. Pricing and terms subject to change without notice. Buyers are encouraged to submit their strongest offer promptly.

1001 Shirley St Unit 3, Winthrop

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.
28 Thornton Park, Winthrop
$775,000
5 Beds ⋅ 3 Baths ⋅ 73461231 MLS
Discover an investor’s dream in the heart of Winthrop. Set on a generous lot on a quiet, friendly street, 28 Thornton Park offers a rare opportunity to bring a fully gutted two-unit multifamily back to life. The property has been taken down to the studs and is ready for renovation—perfect for developers, investors, or owner-occupants looking to customize their ideal home while building long-term value. Enjoy the convenience of being just a short walk to Winthrop’s town center, local shops, restaurants, and the beach. Whether you’re envisioning rental income, condo conversion, or a multigenerational layout, the possibilities are endless. A rare find in an unbeatable location!

28 Thornton Park, Winthrop

Listing courtesy of Listing Agent: Carlisle Group from Listing Office: Compass.

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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