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Cottage-Style Homes for Sale on the South Shore

Looking for a cozy, character-filled home with timeless charm? Cottage-style homes offer distinctive architectural features like gabled roofs, inviting porches, and efficient layouts found across South Shore towns.

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39 Ash Avenue Somerville MA 02145

Somerville, MA39 Ash Avenue

Price$859,000

Est. Mortgage: $/month

Under Agreement

MLS Number 73509517

  • Residential
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,301

Charming single-family with an oversized lot and inviting backyard patio! This home at 39 Ash Ave was thoughtfully reimagined in 2026, featuring new hardwood flooring, custom shelving, and refreshed cabinetry. The bright, well-proportioned layout offers comfortable living with excellent flow and a flexible floor plan with potential to create a third bedroom or office. Rare for the area, the generous lot provides a spacious backyard with patio-perfect for entertaining, gardening, or unwinding outdoors-along with future expansion potential. Ideally located near Magoun Square, the Green Line Extension, parks, and popular dining. A unique opportunity to enjoy move-in-ready living with exceptional outdoor space and long-term upside

Listed by Ian Crotty of The Boston Realty Group,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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51 Undine Avenue Winthrop MA 02152

Winthrop, MA51 Undine Avenue

Price$659,900

Est. Mortgage: $/month

MLS Number 73509184

  • Residential
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,250

Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you'll find newer flooring, fresh interior paint, updated lighting, and a beautifully remodeled kitchen complete with stainless steel appliances. The home also features an updated bathroom, newer windows, and exterior doors throughout. The first floor boasts an open and versatile layout with a modern kitchen, spacious living and dining areas, and a bedroom currently being used a home office-all enhanced by water views. Upstairs, you'll find two well-appointed bedrooms and a full bathroom. Conveniently located near public transportation, including bus routes with direct access to the MBTA.

Listed by The Caceda Team, Silvia L. Caceda and Winfield Clamens of Coldwell Banker Realty - Lynnfield

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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64 Central Street Marshfield MA 02020

MLS Number 73508072

  • Residential
  • Bedrooms 4
  • Bathroom 1
  • Square Feet 1,068
  • High School Marshfield

Opportunity awaits in one of Marshfield's most desirable locations! This home has been owned by a family for generations with memories that will last a lifetime! Currently a 4- Bed 1-Bath cottage. This property offers a blank canvas for builders, investors, or buyers looking to create their dream home. Nestled in a highly sought-after area, the value here is all about the land and unbeatable setting. Enjoy close proximity to beaches, marinas, local shops, and dining, along with easy access to major routes for commuting. Whether you envision a custom coastal retreat or a smart investment project, this lot provides the perfect foundation. Bring your vision-properties in this location rarely come available with such potential. Home is being sold As-Is. Do not walk property without listing agent!

Listed by Colleen Cupples of Conway - Marshfield

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Saquish Beach Boulevard Plymouth MA 02360

MLS Number 73507909

  • Residential
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,860

These waterfront cottages are passed down through generations and rarely offered--here is your opportunity! A private, off-grid enclave accessible by 4WD or boat, Saquish offers unmatched seclusion. The open floor plan is ready for summer enjoyment, currently configured to sleep a large group. Updated roof, windows and siding. Tucked in the dunes, enjoy sweeping views, bay breezes, an oversized deck, and a second-floor balcony. This is a location defined by its rarity--where land narrows and the Atlantic surrounds you in a dynamic coastal landscape shaped by tides, light, and season. This location is where Plymouth, Cape Cod and Duxbury Bays all intersect. Wake to sunrise over the bay, spend your days with direct beach access, and end with unobstructed sunset skies. Whether a seasonal escape or legacy holding, this is a opportunity to own in one of the South Shore's most tightly held coastal settings. Short term rental potential. Ready to enjoy as is, but the possibilities are endless

Listed by Gilded Girls Group of Beach Homes Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Loons Call Plymouth MA 02360

MLS Number 73507825

  • Residential
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,133
  • High School Plymouth

One of few remaining homes at Owls Nest. The popular Lexington one level home features an open layout connecting the kitchen, casual dining, and great room, soaring 12' ceilings, a gas fireplace and sliding glass door leading to the deck and stairs to the rear yard. The generous primary bedroom suite includes a light filled bathroom with a large walk in shower, marble seat, dual sink vanity, and walk in closet. Guests will enjoy a secondary bedroom with a walk in closet and bathroom, this home also includes a flex room\den, dedicated work space, mud room and main floor laundry room. Additional features of this home include a bright unfinished walkout basement with a glass door leading to the rear yard. Work with our team of professionals to select from today's popular finishes, home automation, technology and outdoor living.

Listed by Christine Sweeney and Amy Heinrichs of Toll Brothers Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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32 Loons Call Plymouth MA 02360
Under Agreement

MLS Number 73507812

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,309
  • High School Plymouth

New Construction! Choose the popular Chatham Cottage for this homesite, featuring main level living and private second floor space for guests. This home includes a bright unfinished lower level with access to the rear yard. The grand two story foyer leads to a spacious kitchen with island and casual dining, and is open to the great room with 12' ceilings, gas fireplace, and access to an included deck. The luxurious first floor primary bedroom suite includes a stunning bathroom with a large walk in shower, marble seat, dual sink vanity, and spacious walk in closets. Also located on the main level, a secondary bedroom, full bathroom, office, and laundry room. The second floor features privacy for guests including a bedroom suite with walk in closet, full bathroom and finished loft space. Work with our team of professionals and choose from today's popular finishes, security, home automation and outdoor living for your dream home.

Listed by Christine Sweeney and Amy Heinrichs of Toll Brothers Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Reservation Road Fairhaven MA 02719

Fairhaven, MA16 Reservation Road

Price$699,800

Est. Mortgage: $/month

Contingent

MLS Number 73507675

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,936

Previous buyers were unable to fulfill their home sale contingency. YEAR ROUND WATERFRONT - Amazing views & water access! This home offers flexible layout options. The wall of windows on the first floor overlook the water & provide magnificent light throughout the day. The first floor living room highlights a beautiful brick fireplace serving as a focal point for gatherings, while the beamed ceiling & wood wall add character & a sense of charm. First floor - 2 bedrooms & a full bathroom. Second floor - additional bedroom, full bathroom, & front to back family room. Second floor bathroom is appointed with a tiled walk-in shower & double vanity, offering both convenience & a touch of luxury. This home is perfect for outdoor entertaining & also features an outdoor shower, a large patio which is partially covered, as well as a balcony and deck where one can relax & enjoy the never-ending beauty of a waterfront view. A year round home with a vacation view!

Listed by Mia Holland of LPT Realty - Home & Key Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Oceanview Street Winthrop MA 02152

Winthrop, MA5 Oceanview Street

Price$690,000

Est. Mortgage: $/month

Under Agreement

MLS Number 73503432

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,500

***Seller is VERY motivated***Welcome to your fully renovated and updated home on a quiet corner in Winthrop. This home features a brand new kitchen with wide spanning island, open to the living room. Perfect for entertaining. All new electrical, water heater, furnace, plumbing, insulation and hard wired fire alarms. Approximately 250 sqft was added on and 2 bathrooms were also added making this a 3 bedroom 3 bathroom home. Conveniently located primary bedroom on the first floor has ensuite bathroom. All appliances in home are brand new, half bath located off the kitchen makes it easy for guests to use. Smart thermostat that can be controlled from your phone even when you are on the go. It really is a wonderful little corner lot home with ample yard space if you wanted a garden, front of the house gets sun all day. Walking distance to T and beach and other amenities Winthrop has to offer. OPEN HOUSE: 7/10 5:30-6:30PM. 7/11 10:30AM-12PM. OFFERS DUE MONDAY JULY 13th by NOON.

Listed by Nezihe Hewson of Mariano Smith & Co.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Josiah Path Falmouth MA 02540

Falmouth, MA29 Josiah Path

Price$1,300,000

Est. Mortgage: $/month

Under Agreement

MLS Number 73503030

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,100

New Construction of a semi-custom home to be built! Highly desirable lot abutting town conservation land. This home will feature cathedral ceilings, first floor primary suite, quartz counter tops, professional landscaping, sprinkler system and so much more. The Village at Brick Kiln Road is a new development of incredibly crafted and unique homes. Chapoquoit beach with its incredible sunsets is only 2 miles down the road. It is approximately 2 miles from the historic Falmouth downtown where one can find shopping, restaurants, bars, and coffee shops adorning the street. The development is next to the future $30 million fitness facility of the YMCA. There are numerous beaches and marinas in the area. This is a new development consisting of 28 new homes of which 13 are sold or under agreement already. Please visit the website for more information.

Listed by Kerry Bourne of Grade A Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 Wessagussett Road Weymouth MA 02191

MLS Number 73498446

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,094
  • High School Weymouth High School

Welcome to 81 Wessagussett Rd in North Weymouth, just steps from Wessagussett Beach. This spacious home offers 2,094 sq ft of living space, providing plenty of room to spread out and make it your own. Major updates completed in 2020 include a new roof, energy-efficient heat pump, central A/C, and updated windows, giving peace of mind for years to come. The unbeatable location is the true highlight, offering easy access to the water, nearby amenities, and commuter routes. A rare opportunity to own a well-sized home in a highly desirable coastal neighborhood.

Listed by The Jenkins Group and Nathan Jenkins of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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309 Bradford Street Provincetown MA 02657

Provincetown, MA309 Bradford Street

Price$4,500,000

Est. Mortgage: $/month

MLS Number 73497147

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 2,492

Exceptional East End offering spanning from Commercial Street to Bradford Street! This rare two-parcel opportunity consisting of 624 Commercial Street and 309 Bradford Street is awaiting your vision! Ideally situated near public access to a pristine bay beach, this assemblage combines location, versatility, and potential. 624 Commercial Street offers a 5,002 sq ft lot with a newly constructed three-bedroom residence, with the possibility to accommodate a fourth bedroom or ADU. 309 Bradford Street features an 8,175 sq ft lot with a charming one-bedroom cottage, well-suited for guest accommodations or rental use. Both properties include generous outdoor space and off-street parking, presenting a unique opportunity for expansion, investment, or the creation of a private compound in Provincetown's desirable, and historic East End.

Listed by The Rose Kennedy Team and Shelby Zawaduk of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Off Canoe Landing Plymouth MA 02360

MLS Number 73496441

  • Residential
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 709

This 1930's cabin is located within the ''pine hills'' community. Located on 14 acres with frontage on Great Island Pond. This 3 bedroom 1/2 bath cabin has a fireplaced living room, porch facing the water and dock. Garage under can store your boat. This ''off the grid'' property is powered by Propane for the generator, stove and refrigerator. The generator powers the lights for the cabin and well water.

Listed by Greg DeCenzo of Kinlin Grover Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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 or leasing 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 or leasing. MLSPIN 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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