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$560,000
3 Beds 2 Baths SOLD Status 73433469 MLS 1,724 SqFt.
Welcome home to 41 Sargent Street. Set on one of Winthrop’s most desirable picturesque tree-lined streets and just a short walk to the ocean, this 3 Bed, 2 Bath lovely Colonial is just waiting to be lovingly restored for it's next chapter. Offering convenience and charm and a thoughtful flow throughout. With a large sun-filled kitchen, 1st floor laundry & full bath, and a vast & versatile living space, the possibilities are endless. Hardwood floors lie hidden beneath the carpet, ready to shine again. Upstairs you'll find generously sized bedrooms, another full bath, plus a walk-up attic for even more potential. Start your day with coffee on the charming covered porch, then enjoy a peaceful walk along the water. Conveniently located near the airport, schools, shops, restaurants, public transportation, golf club, and the marina— this home blends character, location, and opportunity. Being sold "as-is." Bring your vision & restorative imagination and make this coastal beauty your own!

41 Sargent St, Winthrop

$780,000
5 Beds 3 Baths SOLD Status 73432635 MLS 1,923 SqFt.
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

$740,000
3 Beds 3 Baths SOLD Status 73432311 MLS 1,716 SqFt.
Welcome to 59 Crescent St in Winthrop. This well-kept bungalow offers 1,716 square feet of living space with 3 bedrooms and 2.5 bathrooms. The first floor includes a large living room with skylights, bay windows, hardwood floors, and recessed lighting, a dining area, and an updated kitchen with granite counters, stainless steel appliances, and a gas stove. Upstairs, you will find comfortable bedrooms with hardwood floors and a modern full bath. Outdoor space features a brand new deck, fenced yard, enclosed porch, and off-street parking. The home sits on a 6,125 square foot lot at the end of a quiet, dead-end street with few neighboring homes, providing added privacy. Just a short distance to the beach, public transportation, parks, golf, the marina, and local shops and dining, this property offers both charm and convenience.

59 Crescent St, Winthrop

$900,000
3 Beds 2 Baths SOLD Status 73432055 MLS 1,883 SqFt.
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

$415,000
2 Beds 1 Baths SOLD Status 73430474 MLS 1,015 SqFt.
NEW AMAZING PRICE! INCREDIBLE OPPORTUNITY, UNLIMITED POTENTIAL.......Single family living/condo alternative in the quaint oceanside location of Point Shirley in Winthrop by the Sea! A desirable open floor plan consists of Living room, Dining room and kitchen with beautiful oak flooring and a very nice large updated full bathroom and 2 good size bedrooms. All on one level for easy living. Ocean breezes, amazing sunrises and sunsets abound for your peaceful enjoyment and natural beauty! The fun awaits with so many choices to make it your own. Two car off street parking and easy access to the beach! ***This Property has been approved for all new windows and doors**** With the The Massport Soundproofing Program. GREAT INVESTMENT PROPERTY and IDEAL AS A SUMMER HOME TOO!!

900 Shirley Street, Winthrop

$884,000
5 Beds 3 Baths SOLD Status 73429466 MLS 2,397 SqFt.
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

$880,000
3 Beds 2 Baths SOLD Status 73429307 MLS 1,905 SqFt.
THIS INCREDIBLE AND PRIVATE LOCATION OFFERS SO MUCH NATURAL BEAUTY........Stunning Winthrop harbor views from this totally renovated 3 BR, 2 full bath seaside single with garage. Quality upgrades, Open Floor plan, crown moldings, stunning accent wall and amazing oversized windows that invite in amazing views and natural sunlight! Beautiful quartz kitchen with dual cabinet colors, Stainless appliances and center island all makes for an ideal set up for entertaining. Gorgeous designer baths with rain shower fixtures, black accent hardware throughout, and new golden oak floors all make this home a place you will want for your own. A bonus room in the basement adds to the generous living space in this 3 level home. All the work's been done, move right in and Enjoy! Winthrop by the Sea with 2 beaches, new schools, a 9 hole golf course, 3 Yacht Clubs and lots of fun Eateries, live as if you are on vacation!

12 Winthrop St., Winthrop

$1,590,000
2 Beds 2 Baths SOLD Status 73428627 MLS 2,455 SqFt.
Dramatic oceanfront retreat! This spectacular, fully renovated 2-bed, 2-bath ranch offers panoramic water views from every room. Vaulted ceilings enhance the open-concept living room, leading to a chef’s kitchen with custom cabinetry and stone counters. Relax year-round in the sun-drenched 4-season sunroom or entertain on the ocean-facing lawn. Finished basement offers flexible living space for a media room, guest suite, or home office. Wake up to the sound of waves and end each day with vibrant sunsets. Situated on a 0.28-acre lot with future expansion potential. Whether you're looking for a primary residence or weekend escape, this home is your ticket to beachfront living with elevated elegance.

23 Nahant Ave, Winthrop

$480,000
3 Beds 1 Baths SOLD Status 73428565 MLS 1,369 SqFt.
Steps to the BEACH. Minutes to BOSTON. Seconds to fall in LOVE. This isn’t just a condo - it’s a whole new pace of life. Welcome to 23 Trident Ave where you have the opportunity to make your home ownership dreams a reality. This beautiful 4 Bed 1 Bath unit with a heated bonus room has been meticulously maintained. Spacious kitchen with ample cabinet space, granite counters, stainless appliances and recessed lighting. This unit also boasts Central A/C, in unit Laundry, a 10x10 storage room basement Storage, and 1 off street parking spot. What's not to love? It's time to stop paying someone else's mortgage and start being the captain of your own ship or you can have people paying you rent. With excellent rental potential, this unit was previously rented for $3250. Schedule your showing now!

23 Trident Ave Unit 2, Winthrop

$585,000
3 Beds 2 Baths SOLD Status 73428498 MLS 1,166 SqFt.
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

$462,000
3 Beds 1 Baths SOLD Status 73427739 MLS 1,325 SqFt.
Experience coastal living in this spacious 3-bedroom, 1-bath top-floor unit in desirable Winthrop, MA. Offering over 1,300 sq. ft. of living space, this home features the convenience of in-unit laundry, two private decks and two dedicated parking spaces. Enjoy ocean views from your private deck while sipping your morning coffee. Recent updates include, newer windows, newer roof, new oil tank and full blown insulation. Situated only 3 houses away from the beach! With its close proximity to Boston, you'll have the best of both worlds: a serene seaside retreat with easy access to the city. Don't miss this rare opportunity for comfort, location, and lifestyle. Open houses Sat 9/13 & Sun 9/14 11-1. Offers due Monday 9/15 4pm.

26 Forrest St Unit 3, Winthrop

$1,150,000
6 Beds 3 Baths SOLD Status 73427022 MLS 3,458 SqFt.
One of a kind. 10+ rooms of meticulousness combining warmth and character. Built 1925 in the New England coastal Maze area, nearby Cottage Park Yacht Club. 3 solid wood entry doors lead to amazing flow on main level with sunny exposures thru oversized windows. Designed by MIT architect John Whitmore. Flood insurance is NOT required in this sought after location. Gas fireplace in living room adds to ambience. Talented master woodworker CUSTOM designed the perfect kitchen with stainless steel, abundant cabinets for storage +butlers pantry. Kitchen Opens to Fantastic ADDITION featuring wooden beams, exposed brick fireplace wall, built ins, skylights and picture window overlooking exquisite tree species. Bonus 1/2 bath on main level. 6 spacious bedrooms (home offices/gym) plus 2 full bathrooms. UPDATED electric and plumbing. 3 heating zones and cooling. 3 car parking in driveway. A seaside paradise ideal for dog walks,beaching, boating. Short distance to vibrant town center + Boston.

66 Lowell Road, Winthrop

$830,000
4 Beds 3 Baths SOLD Status 73426322 MLS 2,000 SqFt.
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

$715,000
3 Beds 3 Baths SOLD Status 73425030 MLS 1,973 SqFt.
Step inside this beautifully reimagined residence where timeless charm meets modern comfort. This 3 bedroom, 2.5 bath home has been fully renovated with thoughtful design choices that highlight the building’s historic character while adding the conveniences of today. Original hardwood floors anchor the sun-filled interior, where a welcoming living area flows into a stylish kitchen, complemented by a convenient half bath- ideal for guests. The first-floor primary suite creates a true retreat, complete with a private bath and generous closet space. A bright sunporch extends your living space, while the back deck opens to a shared yard, perfect for gatherings. Upstairs, two additional bedrooms share a full bath with a classic tub, offering comfort and privacy. With laundry in-unit, storage in the basement, and two off-street parking spots, this home balances character with practicality. Every detail has been carefully considered, making this residence as welcoming as it is distinctive.

174 Winthrop St Unit 2, Winthrop

$1,665,000
6 Beds 4 Baths SOLD Status 73424484 MLS 4,455 SqFt.
One of a kind! Queen Anne Victorian. Two blocks from Cottage Park Yacht Club. Over 4,400 square feet of living space with 6 bedrooms, 3.5 fully renovated baths, 2nd floor laundry room and 2 finished basement rooms. Stunning details include high ceilings, hand carved newel posts and mantels, 3 Chelsea tile fireplaces, oak flooring and woodworking, wainscoted staircases, window seat, pocket doors, and butlers pantry. Oversized windows provide an abundance of natural light. Bright kitchen featuring custom cherry cabinetry, Vermont soapstone countertops, and SS appliances, including a Sub-Zero refrigerator and a 6 burner Viking gas range. The almost 15,000 square foot lot has a 2 car garage with ample additional parking, a shed, and large private gazebo area. A beautiful copper finial topping the peak of the turret, clapboards, scalloped shingles, 2 wraparound porches, and perennial gardens add to this gem’s curb appeal. Availalbe for the first time in 30 years.

191 Cottage Park Road, Winthrop

$380,000
2 Beds 1 Baths SOLD Status 73424022 MLS 782 SqFt.
Welcome to 200 Governors Dr Unit 39 – a beautifully maintained top-floor corner unit offering privacy, sunlight, and serene views. This spacious 2-bedroom condo features an open-concept layout with large windows, hardwood flooring, and a generous living/dining area perfect for entertaining or relaxing. The updated kitchen includes ample cabinetry and counter space. Enjoy the comfort of a private balcony, perfect for morning coffee or evening sunsets. Both bedrooms are well-sized with great closet space, and the full bath is clean and bright. Located in a professionally managed complex with amenities such as a swimming pool, tennis courts, and laundry facilities. Heat and hot water included in condo fees! This unit also includes up (2) parking spaces. Conveniently situated near shopping, restaurants, and commuter routes, this is an ideal opportunity for first-time buyers, downsizers, or investors. Enjoy top-floor living in one of the community’s best locations.

200 Governors Dr Unit 39, Winthrop

$490,000
3 Beds 2 Baths SOLD Status 73423786 MLS 1,290 SqFt.
Wake up to the sound of waves and ocean views just outside your window. This spacious first-floor condo offers effortless coastal living with sun-filled oversized windows and an open-concept living and dining area. The modern Viking-equipped kitchen makes everyday cooking a luxury, while the primary suite boasts a spa-like bath with a soaking tub. Two additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy abundant in-unit storage plus bonus basement space for all your beach gear. Step out to your private rear deck or gather on the shared patio, where ocean breezes set the scene. With public transportation close by, you’ll enjoy the perfect blend of city convenience and seaside serenity.

212 Winthrop Shore Drive Unit 1, Winthrop

$1,270,000
9 Beds 3 Baths SOLD Status 73423170 MLS 2,775 SqFt.
OFFER DEADLINE 9/2 3PM Rare find 3family with separate utilities, off street pkg, btfl fence enclosed yard, porches w/views and many updates. Unit 1 was a 3 bed but now has laundry in unit, a huge livingroom/diningroom, bath with jacuzzi tub, central air and large eat in kitchen with oak cabinets and ample counter space perfect for owner occupied. Unit 2 is beautifully renovated with 5rms/3beds and private porch. Unit 3 is 5 rms/3beds laundry in unit and the walk up attic is massive with breathtaking views. Great potential for a 2level unit with renovation. The basement is large and clean, the roof was replaced several weeks ago, unit 1 water heater is 1 y.o. all systems are maintained and serviced regularly and the siding was replaced by Newpro in 2017. Plenty of off street parking with potential for additional spaces, beautiful fence enclosed yard and shed for children, pets, gardening. Unit 1 and 3 will be delivered vacant. Steps to schools & downtown, mins beach, hwy & airpor

19 Jefferson, Winthrop

$650,000
2 Beds 2 Baths SOLD Status 73419713 MLS 1,124 SqFt.
LUXURY OCEAN FRONT CONDO at SEAL HARBOR with direct ocean views! Enjoy coffee in the morning or candlelight dinner on the balcony while listening to ocean waves & boats on water. Beautifully renovated including bathrooms, stainless steel appliances, lights, door handles, freshly painted, outlets, etc. Open concept floor plan to enjoy the delightful views from all the rooms. Front to back dining room/living room is easy living and great for entertainment. Ample cabinetry w/granite countertops and backsplash in kitchen plus nook. Bedrooms have oversized windows overlooking the ocean! Main suite has multiple closets leading to bathroom. 2nd bathroom has laundry closet. Hardwood floors throughout. Enjoy a dip in in-ground heated pool or walks along the oceanfront or game of tennis. Building has gym, sauna, billiard room, storage room, private function room and 24/7 concierge.1 garage space. Easy access to downtown Boston by train, water shuttle or car. Move in and enjoy ocean luxury livin

One Seal Harbor Rd Unit 604, Winthrop

$860,000
5 Beds 3 Baths SOLD Status 73418752 MLS 2,308 SqFt.
Step inside this delightful newly renovated 2 family gem, just a short stroll from the beach, park, Yacht Club, & vibrant collection of local restaurants! Up on Cottage Hill & out of the flood zone, it’s easy to feel like you’re living in 1 beautiful home with the added bonus of a private lower-level. The main home is a light filled living area with gleaming hardwood floors & spacious rooms for sharing with loved ones. The 1st floor is home to a white kitchen with quartz counters & new SS appliances arriving soon, a beautiful white fireplaced oversized living room, a spacious dining room, full bath, & a sun room with high ceilings perfect for a breakfast nook & casual seaside living. The 2nd floor offers 3 good size bedrooms & master ensuite. Discreetly tucked below the 1st floor is a self-contained suite featuring its own entrance, kitchenette, bedroom & full bath, ideal for rental income or extended family. With a new roof & updates throughout it feels like a new constructed home!

77 Cottage Ave, Winthrop

$722,000
5 Beds 2 Baths SOLD Status 73417963 MLS 1,776 SqFt.
Discover this well-loved generational home where character greets you at every turn. Sunlight pours through a stunning stained-glass window in the foyer, hardwood floors flow throughout, and every room tells its own story. The spacious eat-in kitchen is perfect for gatherings, while the large living areas offer space to entertain with ease. A full bath on the first floor adds convenience, and upstairs you’ll find five bedrooms, a second full bath with a tub, and a walk-in closet in the primary bedroom. The basement features a bonus room ready for your renovation vision, home office, or hobby space. Outdoors, enjoy a fully fenced yard with a large deck, patio space, and plenty of room to host summer celebrations, garden, or simply relax in your own private retreat. Move right in and enjoy the charm, or bring your ideas to add even more value-this is a home built for memories, ready for its next chapter.

41 Centre St, Winthrop

$728,000
3 Beds 2 Baths SOLD Status 73416952 MLS 1,994 SqFt.
Welcome to this beautifully updated 3-bedroom, 1.5-bath home just two houses away from Winthrop Beach. This inviting home offers the perfect blend of comfort, style, and seaside living. Bright and spacious open-concept first floor, ideal for entertaining and everyday living with a convenient half bath off of the living room and sliders off of the dining room]. Upstairs are 3 spacious bedrooms, one features a private balcony with views of the beach—your own personal retreat to unwind and take in the sea breeze. Each bedroom is equipped with individually controlled electric heat, offering personalized comfort year-round.The brand new full bathroom is a true spa-like oasis, complete with radiant heated floors, a luxurious spa tub, and a double vanity. Outside, enjoy your in-ground pool and lovely patio area—perfect for summer entertaining, relaxing, or soaking up the sun after a day at the beach. 2 driveways! Basement with great potential for additional living space!

25 Charles St, Winthrop

$390,000
2 Beds 1 Baths SOLD Status 73414564 MLS 679 SqFt.
Beautifully Renovated Condo with Water Views in Winthrop! This thoughtfully updated condo offers modern living on coveted Winthrop Shore Drive, directly facing Winthrop Beach. Featuring a stylish kitchen and open-concept layout, this bright and inviting unit is perfect as a first home, second home, or investment property. Enjoy peaceful water views from the living room or sip your morning coffee while watching the sunrise from the newly redone front porch. Additional highlights include a shared back deck and yard area, plus a private storage unit with a custom workbench — all in a pet-friendly building (restrictions apply). Outdoor enthusiasts will love the nearby walking trails on Deer Island and all that Winthrop has to offer, including restaurants, a golf course, a private yacht club, and public beaches. Commuting to downtown Boston is a breeze — just 20 minutes by car or 30 minutes by T.

23 Winthrop Shore Drive Unit 2, Winthrop

$949,000
5 Beds 3 Baths SOLD Status 73414237 MLS 2,237 SqFt.
Welcome to 26 Sargent Street, a beautifully restored and thoughtfully upgraded single-family residence nestled on one of Winthrop’s most picturesque, tree-lined streets. This expansive 5+ bedroom, 2.5 bath home masterfully blends timeless architectural charm with modern luxury, offering refined living spaces and every contemporary convenience. From the moment you enter, you’ll be captivated by the home’s seamless flow, generous proportions, and impeccable attention to detail. The completely updated kitchen and baths are designed with high-end finishes, while the brand-new two-zone central heating and cooling system ensures year-round comfort. Upstairs, the third-floor retreat offers a private sanctuary, complete with a private bath featuring a sleek walk-in shower — ideal for unwinding after a long day. Outdoors, enjoy a detached garage with full electrical service and a classic front porch perfect for morning coffee or relaxing in the evening. 10k BUYER CREDIT TOWARDS CLOSING COSTS!

26 Sargent St, Winthrop

$839,900
3 Beds 3 Baths SOLD Status 73410073 MLS 2,115 SqFt.
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

$880,000
4 Beds 4 Baths SOLD Status 73413581 MLS 2,764 SqFt.
Welcome to your dream home nestled on a quiet side street in the picturesque seaside town of Winthrop. This stunning 4 bedroom, 3.5 bathroom property blends timeless elegance with modern luxury, offering an abundance of space and upscale amenities just minutes from Boston. Step inside to discover a beautifully designed interior featuring elegant finishes all around, an exquisite almost seashell shaped kitchen island and a stately gas fireplace. The excellent layout includes a spacious in-law suite, offering excellent potential for an ADU conversion. The heart of this home is its private backyard oasis, ideal for entertaining or relaxing. Dive into the heated gunite inground pool, surrounded by lush landscaping and a convenient pool shed. Need more space? Large attic has expansion possibilities as well. Located near award-winning restaurants, beautiful beaches, and a seasonal ferry to Boston, you’ll enjoy all the charm of small-town living with the convenience of the city near by.

17 Buckthorn Ter, Winthrop

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