Gloucester Homes with Cottage Style

Welcome to Gloucester, Massachusetts, a picturesque coastal gem nestled in Essex County. Known for its rich maritime history, vibrant arts scene, and stunning natural beauty, Gloucester offers a unique blend of small-town charm and modern amenities. With its breathtaking ocean views, sandy beaches, and bustling harbor, it’s no wonder that this city has long been a beloved destination for artists, fishermen, and families alike.

One of the most enchanting aspects of Gloucester is its array of charming cottage-style homes. These delightful abodes, often characterized by their quaint architecture and cozy interiors, evoke a sense of warmth and nostalgia. Picture yourself sipping morning coffee on a sun-drenched porch, surrounded by lush gardens and the gentle sounds of the sea. Many of these cottages feature original woodwork, inviting fireplaces, and inviting nooks perfect for curling up with a good book.

Living in a cottage-style home in Gloucester means embracing a lifestyle that values community and connection. Take leisurely strolls along the historic streets, explore local art galleries, or indulge in fresh seafood at one of the many waterfront restaurants. With easy access to outdoor adventures, including hiking trails and water sports, Gloucester offers a perfect blend of relaxation and excitement.

Whether you’re looking for a seasonal retreat or a year-round residence, Gloucester’s cottage-style homes provide a unique opportunity to experience coastal living at its finest. Discover the charm of this beautiful city and find your perfect cottage today!

Newest Gloucester Homes with Cottage Style

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 73550282 MLS

Enjoy living in this Folly Cove property where artist and author Virginia Lee Burton did her life's work. This delightful estate is the well-preserved subject of her children's book "The Little House" The 3.9 acre property includes a sunny farmhouse as well as a separate barn/studio, each of which have been featured in many publications. Virginia wrote her books in the studio and it is also where the Folly Cove Design Group was formed and met. The house has 4 bedrooms and 2 1/2 baths and the historic post and beam studio has a 20' granite fireplace and cathedral ceilings, providing comfort and privacy for guests. Unique features include large granite tables, benches and a cozy firepit. Granite pillars support trailing grapevines and near-by is a quarry and hiking /biking trails. Fruit and nut trees and berry bushes, as well as vegetable and flower gardens complement the yard. This is a magical property with plenty of privacy and parking that lends itself to indoor and outdoor events.

1255 Washington Street, Gloucester

$565,000

2 Beds ⋅ 2 Baths ⋅ 73540674 MLS

Welcome to the heart of East Gloucester's highly desirable neighborhood, where coastal charm meets everyday convenience. Just a short stroll to Good Harbor Beach, this delightful 2-bedroom, 1.5-bath home offers the perfect opportunity for year-round living, a weekend retreat, or a summer getaway by the sea.Nestled on a private, secluded lot, the property features an absolutely charming backyard—ideal for relaxing, entertaining, or enjoying the peaceful surroundings. A beautiful sunroom overlooks the backyard, creating a bright and inviting space to enjoy your morning coffee or unwind after a day at the beach.Ocean lovers will appreciate the unbeatable location, while commuters will love the easy access to Route 128. Additional features include off-street parking and the rare combination of privacy and proximity to Gloucester's beaches, restaurants, shops, and coastal attractions. THIS IS A MUST SEE!

38R Bass Ave, Gloucester

$700,000

2 Beds ⋅ 2 Baths ⋅ 73539294 MLS

This one is all about location. E. Gloucester. A mile from the Good Harbor Beach footbridge, Rocky Neck and a half mile to the Bass Rocks Golf Course. located on a private way off Highland Street. It is clearly a rehab yet worth the effort if you are looking for the classic Gloucester vacation second home. The values of every property in the area, much greater.

30R Highland Street, Gloucester

$2,395,000

2 Beds ⋅ 2 Baths ⋅ 73531602 MLS

This is more than a home—it’s a coastal lifestyle. Follow the steps to the water and dive into the cove at high tide, or wander the beautiful beach at low tide. The views are simply unparalleled. Spend your evenings on the upper deck as the sunset sets the seascape ablaze with color.The chef’s kitchen features nearly new Thermador appliances, reclaimed American heart pine floors, and an oversized island perfect for casual dining. A 10-foot picture window, installed last year, frames the ever-changing coastal scenery. The living room, with its inviting fireplace, opens to a charming covered porch—ideal for outdoor dining from morning coffee to evening meals.Upstairs, the primary bedroom offers breathtaking views stretching beyond Eastern Point. A second-floor family room with access to the upper deck is especially magical in the summer and could be converted into a third bedroom. Welcome to Rocky Neck—a destination people love to visit and a place you’ll be proud to call home.

8 Bickford Way, Gloucester

$750,000

1 Beds ⋅ 1 Baths ⋅ 73515187 MLS

Artist's Cottage — Annisquam/Back Bay, Gloucester. Originally built as an artist's barn, this magical one bedroom cottage sits on nearly an acre of land in one of Cape Anns most beautiful neighborhoods. Enjoy sunrises near the ocean, watch the stars appear at night, and step outside to gardens lovingly cultivated with organic care for over 25 years. A haven for sailors, kayakers, gardeners, writers, and dreamers. Make this your year round or perfect weekend get away spot. Perched atop a hill and safely above coastal storms, yet minutes from Gloucester's finest beaches, quarries, and so many hiking trails. The privacy, beauty and convenience is unmatched. Zoned R-40 with town water and sewer and two potential driveways — build your dream home and use the cottage for guests, studio space, or explore ADU or subdivision potential. Minutes to Annisquam Village and Plum Cove Beach. Come live by the ocean.This diamond is a rare find and won't be on the market long!

38 Revere Street, Gloucester

$534,000

2 Beds ⋅ 2 Baths ⋅ 73514328 MLS

Turnkey Victorian Cottage in downtown Gloucester offering the perfect blend of character and convenience. Ideally located near the train, beaches, shopping, and highway access, the home enjoys ample street parking and added privacy with undeveloped land across the street. The first floor features a spacious living room with coffered ceilings, hardwood floors, and a large picture window, a petite but efficient kitchen along with an adjoining light infused dining room with sliding glass doors leading to a sunny, enclosed backyard, perfect for relaxation. Upstairs includes two generously sized bedrooms, a large bath with stackable washer/dryer, and a versatile third room ideal for office space, nursery, or oversized dressing room. The finished lower level houses a half bath, open living space, separate entrance, and abundant storage.

8 1/2 Myrtle Square, Gloucester

Start Your Search

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.

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .