Winthrop Homes with Colonial Style

Welcome to Winthrop, a charming coastal town located in Suffolk County, Massachusetts. Known for its picturesque views of the Atlantic Ocean, Winthrop offers a unique blend of small-town charm and convenient city access.

If you are a fan of Colonial-style homes, Winthrop is the perfect place for you. With a variety of homes boasting classic Colonial architecture, you can find the perfect blend of historic charm and modern amenities. From traditional brick facades to elegant columns and symmetrical designs, Colonial homes in Winthrop offer timeless appeal.

Living in Winthrop means enjoying a close-knit community with access to beautiful beaches, scenic parks, and a thriving local dining scene. Whether you're strolling along the Winthrop Beach Reservation or exploring the shops and restaurants in town, you'll find plenty to love about this coastal gem.

If you're in the market for a home that exudes classic charm and character, consider exploring the Colonial-style homes in Winthrop. With their timeless design and rich history, these homes are sure to capture your heart and provide a warm and inviting place to call home.

Newest Winthrop Homes with Colonial Style

$979,000

4 Beds ⋅ 3 Baths ⋅ 73593881 MLS

Welcome to Winthrop Center. This well-maintained home combines quality craftsmanship with convenient access to the town center. Inside, sun-filled rooms and refined finishes create a cohesive, inviting feel. Spacious gathering areas provide room to entertain, and the home is move-in ready. Nearby, enjoy conservation trails, beach access, shopping, dining, and major commuting routes. This home offers a blend of character, quality, and town-center convenience.

316 Bowdoin St, Winthrop

Listing courtesy of Listing Agent: Jay Karuna Ratne from Listing Office: Venture.

$989,000

3 Beds ⋅ 4 Baths ⋅ 73592852 MLS

FULLY GUT-RENOVATED IN 2026 | SINGLE-FAMILY WITH ADU | INCREDIBLE INCOME POTENTIAL! A rare opportunity to own a beautifully renovated home with a separate accessory dwelling unit (ADU) in one of Winthrop's most desirable neighborhoods! Completely gut-renovated in 2026, this unique property offers the feel and convenience of new construction with exceptional flexibility for homeowners and investors alike.The main residence features 2 bedrooms, 2 full bathrooms, a basement, and in-unit laundry. The ADU offers 1 bedroom plus a bonus room, 1.5 bathrooms, in-unit laundry, and two private decks. Two off-street parking spaces behind the property provide added convenience. Location is another standout feature! Situated just around the corner from Winthrop High School, Winthrop Middle School, and the golf course, this property offers incredible convenience in an established neighborhood. Imagine living in one unit while renting the other to help offset today's higher mortgage payments. With the schools just steps away, the ADU could be especially appealing to a local teacher or school employee seeking a convenient commute!Whether you're looking for multigenerational living, additional rental income, or the opportunity to rent both units as an investment, the possibilities are exciting. Two distinct living spaces, a complete 2026 renovation, off-street parking, and a prime Winthrop location make this a truly unique opportunity.

44 Bowdoin Street, Winthrop

Listing courtesy of Listing Agent: Jenny Golic from Listing Office: Bowdoin Real Estate Partners.

$665,000

3 Beds ⋅ 2 Baths ⋅ 73589094 MLS

Welcome to 14 Irwin Street, a charming single-family home in one of Winthrop’s inviting residential neighborhoods. Offering approximately 1,413 square feet of living space, this classic two-story home features 3 bedrooms, 1.5 bathrooms, and 7 total rooms, providing a comfortable foundation for your next chapter. Enjoy the best of Winthrop’s coastal lifestyle with the beach just a short walk away at the end of the street. Plus, with a bus stop just steps away, public transportation is conveniently accessible for an easier daily commute. From morning walks by the water to summer afternoons at the beach, this location makes everyday living feel a little more special. Set on an approximately 4,792-square-foot lot, this home offers room to grow and plenty of opportunity to make it your own. Built circa 1900, the property retains the character of an earlier era while inviting buyers to bring their own vision and personal style. Whether you’re looking for a family home or a place to create lasting memories, 14 Irwin Street offers a wonderful opportunity in a desirable seaside setting. A wonderful combination of coastal charm, convenient public transportation, and neighborhood appeal—truly a must-see property!

14 Irwin St, Winthrop

Listing courtesy of Listing Agent: Brian Perrin from Listing Office: Brian J. Perrin Real Estate.

$799,900

5 Beds ⋅ 3 Baths ⋅ 73587974 MLS

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

Listing courtesy of Listing Agent: Patricia Nunez from Listing Office: Redfin Corp..

$679,900

2 Beds ⋅ 1 Baths ⋅ 73582921 MLS

Welcome to 7 Enfield Road, a captivating single-family residence in Winthrop, MA. Built in 1930, this inviting home spans 1144 square feet and is ready for you to move in. It offers a unique blend of classic charm and comfortable living, set on a generous 6969 square foot lot. The living room provides a warm and inviting atmosphere, centered around a charming fireplace, and features elegant hardwood flooring that extends throughout the space. The bedrooms, designed for comfort and tranquility, also boast classic hardwood flooring, creating a cohesive and timeless feel throughout the private areas of the home. This property also includes a convenient one-car garage, a full basement offering ample storage or potential for future customization, and a welcoming porch perfect for enjoying the outdoors. Discover the effortless lifestyle awaiting you at this charming Winthrop address. Convenient location to Winthrop Center and shopping, Cummings Elementary School or walk to Ingleside Park, tennis and basketball courts, pickle ball courts and Donovan's beach.

7 Enfield Road, Winthrop

Listing courtesy of Listing Agent: Nicholas Martino from Listing Office: Noddle Island Real Estate.

$947,900

6 Beds ⋅ 3 Baths ⋅ 73567723 MLS

At this attractive new price, this is more than just a home, it’s a chance to embrace the coastal lifestyle that makes Winthrop so special! Just moments from the beach, this beautifully updated 6-bedroom Colonial offers the rare combination of timeless character, modern comfort, and a lot of room for everyone. Featuring over 2,600 square feet of living space (plus additional 600+ sq ft in finished basement) gleaming hardwood floors, fireplaces, a partially finished lower level, and a very welcoming front porch, every space invites you to relax, gather, and create lasting memories. Extensive upgrades, including updated electrical, plumbing, heating, central A/C and very efficient mini spit system. Outside, enjoy a good sized, fenced backyard, large 2-car detached garage, and plenty of off-street parking. At this price, opportunities like this are hard to find in this section of Winthrop! Come experience the charm, space, and value for yourself! Very easy to view! Book your appointment now before it is too late!

217 Pleasant Street, Winthrop

Listing courtesy of Listing Agent: Louis Bonavita from Listing Office: Benton Real Estate Company.

$2,100,000

5 Beds ⋅ 6 Baths ⋅ 73550891 MLS

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

Listing courtesy of Listing Agent: Atiyeh Cassidy from Listing Office: Blue Sky Realty.

$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.

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Winthrop Homes with Colonial Style

Newest Winthrop Homes with Colonial Style

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