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$1,649,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73531935 MLS ⋅ 2,357 SqFt.
Ideally located on one of Marblehead’s most sought-after streets, this beautifully updated 1880 Colonial offers the quintessential walkable coastal lifestyle. Just moments from parks, the waterfront, restaurants, shops, and all that downtown Marblehead has to offer, the home seamlessly blends historic character with modern comfort. Original details, including beamed ceilings and a wood-burning fireplace, create warmth and charm throughout. The renovated kitchen features stone countertops, stainless steel appliances, a spacious dining area, and direct access to a covered porch overlooking the backyard. A flexible first-floor den, office, or bedroom and full bath provide added versatility. Upstairs are three generous bedrooms, a full bath, and laundry. The finished lower level includes a family room, bedroom, full bath, and exceptional storage. Recent improvements include an oversized heated garage with expansion potential, plus updated heating, roof, and siding.

55 Gregory St, Marblehead
$6,250,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73528490 MLS ⋅ 7,231 SqFt.
Set high on nearly an acre in one of Marblehead Neck's most prestigious locations, this 6 bedroom, 5.5 half bathroom exceptional Colonial captures lovely views of Marblehead Harbor while offering privacy, elegance, and timeless architectural appeal. A circular driveway and extraordinary landscaping introduce beautifully curated living spaces where a top-to-bottom renovation has seamlessly blended classic architectural detail with superior designer finishes throughout. From Belgium bluestone flooring to German imported glass on the bar, every detail was thoughtfully selected to the highest standard. Rich wood detailing, crisp moldings, soaring ceilings, and expansive windows frame harbor views and fill the home with natural light. Grandly scaled rooms open effortlessly to a wraparound porch, deck, and bluestone patios. A stunning pool and hot tub are perfectly positioned beside an expansive flat lawn — creating an exceptional private setting for relaxation and entertaining.

48 Harbor Ave, Marblehead
$3,750,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73528472 MLS ⋅ 6,241 SqFt.
Spacious and bright Marblehead Neck home with ocean views, deeded beach rights and a separate waterfront lot that is included with the sale. The main living areas are open-concept and perfect for entertaining! The dramatic primary suite has cathedral ceilings, a spacious sun-lit solarium, a luxurious marble bathroom and a separate fire-placed whirlpool/spa room. The home has 3 other bedrooms (one which can be a home office) plus a guest/au pair/in-law suite. Some of the many amenities include; the flexibility of the open living room/dining room/sitting room combination, 5 1/2 bathrooms, large fire-placed family room, numerous decks with ocean views, large sauna, exercise room, heated outdoor pool, fire-placed recreation room and heated 2-car attached garage. The property has deeded Beach Rights just steps away and owns an ocean-front parcel of land across the street on Ocean Avenue.

244 Ocean Avenue, Marblehead
$1,795,000
3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73528423 MLS ⋅ 2,136 SqFt.
Beautifully renovated, rich in character, blended w/ old and new craftsmanship, located in the shadow of Abbot Hall, only blocks to the harbor. Set on an amazing 1/4 acre (10,280 SF) lot, the property features spectacular perennial gardens, lawns, & several outdoor seating areas - including a spacious stone patio for summer dining & a side patio that is ideal for a grilling. Built in 1842, this very special property offers a sense of historical scale & style -including wainscoting, crown moldings & wide pine floors - plus a custom-built mahogany office in the formal spaces that blend seamlessly with a totally renovated, light-filled, open family room & kitchen designed for contemporary comfort at the back of the house. The custom-built kitchen includes a striking center island with Brazilian "White Panda" marble counters & stove top surround, stainless appliances, custom cabinetry, plus a pantry. The 2nd floor offers 3 BRs -main ensuite plus 2 good size bedrooms & a second full bath.

27 Waldron Street, Marblehead
$1,799,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73524822 MLS ⋅ 4,047 SqFt.
Spacious 4 bedroom 3.5 bath on a quiet cul-de-sac street. Bright & open main living level features cathedral ceilings, skylights, dining space, kitchen with new Sub-Zero fridge adjacent to custom walk-in pantry, walk-out deck access and laundry room. Massive primary bedroom on main living level features 2 huge walk-in closets and a large bathroom complete with jacuzzi tub & large standing shower. Upper level boasts open landing with 3 additional bedrooms (including one with ensuite bath and walk-in custom closet) plus a full bathroom. Lower level features finished bonus room perfect for playroom or a home office/gym, a cedar closet and lots of storage. The .25 acre lot is professionally maintained with irrigation & landscaping. Multi-bay double depth garage can easily hold 4 cars. A side driveway can accommodate boat storage. The owned solar panels (savings of $1,200/yr on electricity) sit on a brand new roof. Short walk to town, beach, rail trail and high school.

53 Gerald Road, Marblehead
$869,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73523862 MLS ⋅ 1,970 SqFt.
At the end of this picturesque tree-lined cul de sac, sits 25 Countryside Lane, a 3 bed, 2 bath Split-Level home with loads of character. The open foyer with coat closet leads to both the upper and lower levels. Upstairs offers open-concept living with living & dining rooms, kitchen and family room addition off the back as well as 3 bedrooms with custom built-ins and an updated bathroom. The lower level bonus room, more recently remodeled, includes luxury vinyl floors, cedar closets, built-in desk/office area, full bath with walk-in shower, and direct access to the backyard via a small staircase (in-law potential). This light-filled home has hardwood floors on the main level, fireplace, updated bathrooms, central air and a 1-car garage, Enjoy outdoor entertaining on the large back deck that overlooks a professionally groomed yard and the wooded walking/biking path, a private paradise! Close proximity to schools and the path which extends from downtown all the way to Preston Beach!

25 Countryside Ln, Marblehead
$1,945,000
3 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73523816 MLS ⋅ 3,463 SqFt.
Steeped in history yet designed for modern living, this rare offering at the iconic Marblehead Academy in Old Town blends timeless architecture with refined luxury. Thoughtfully converted into two exclusive residences, this spectacular 3,463 sq ft townhouse lives like a single-family home and is filled with natural light from oversized windows highlighting soaring ceilings, rich hardwood floors, and original woodwork throughout. The expansive main level offers exceptional entertaining space, a chef’s kitchen with a large island, and a private office. Black iron fixtures and a custom gas fireplace honor the home’s historic character. Three oversized bedrooms feature en-suite baths and generous closets, while the flexible third floor is ideal for a primary suite, family room, guest space, gym, or fourth bedroom. Enjoy a Beacon Hill-style stone patio, fenced yard, garden shed, and two off-street parking spaces.

44 Pleasant St. Unit 1, Marblehead
$1,350,000
3 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73521395 MLS ⋅ 3,117 SqFt.
Located on a lovely tree-lined street just steps to Glover School,this beautifully maintained & updated, 8+ room home blends timeless character w/modern comfort.The bright & expansive 1st flr features an open layout w/hardwood floors thru out,a FP living room, family room, home office, 4-season sunroom, & a modern kitchen w/dining area, perfect for everyday living & entertaining. 3 renovated bathrooms include the addition of a stunning primary en-suite.The spacious primary bedroom offers dramatic cathedral ceilings,along w/2 oversized bedrooms.A flexible floor plan provides for a 1st floor 4th bedroom, ideal for guests,or extended family.Recent improvements include a new HE gas furnace, Central AC, exterior wood shingle replacement, freshly painted interior & exterior & more! The finished LL adds valuable bonus living space.Outside,enjoy a large deck,for entertaining, play or relaxation,overlooking a landscaped,level fenced yard w/irrigation. Walk to the beach! Simply Perfect!!

30 Shetland Rd, Marblehead
$995,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73521163 MLS ⋅ 3,258 SqFt.
Nestled in the heart of Marblehead’s historic district, these attached antique homes offer a rare opportunity to restore and reimagine a special property rich in character and history. Featuring wide pine and hardwood floors, period details, and glimpses of the harbor, the homes are ready for thoughtful updating and restoration. The property includes a truly magical backyard patio and side yard—an uncommon and enchanting outdoor space rarely found in Old Town—ideal for gardening, entertaining, or simply enjoying the charm of the neighborhood. Located just moments from Marblehead Harbor, historic landmarks, shops, and restaurants, this unique offering presents endless potential for contractors, investors, or buyers looking to create something truly special in one of Marblehead’s most treasured neighborhoods.

29 & 31 Circle Street, Marblehead
$2,750,000
7 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73520018 MLS ⋅ 5,306 SqFt.
Historic Elegance Meets Modern Luxury on Marblehead Neck. Set along prestigious Ocean Avenue, directly across from iconic Castle Rock, this magnificent 1880 Gambrel blends timeless character with thoughtful modern updates. Lovingly held by the same family for generations, the home has been expanded to offer over 5,300 square feet of gracious living space, featuring 7 bedrooms and 4.5 baths, plus a spacious 1,200 sq.ft. basement. Ocean & Harbor views included with the home. The half-acre property includes an outdoor pool, four-car garage, and additional driveway parking. Just steps to Castle Rock Beach and moments from downtown Marblehead, Shubie’s Market, acclaimed restaurants, and the Historic District, this is a rare opportunity to own a distinguished residence in one of the North Shore’s most coveted coastal enclaves, ideal for entertaining, everyday living, and creating lasting legacy moments.

372 Ocean Avenue, Marblehead
$3,150,000
4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73516613 MLS ⋅ 4,705 SqFt.
Nestled at the end of a private enclave in Marblehead, this beautifully renovated custom Nantucket-style shingle home offers timeless coastal charm & modern luxury. The home features 4 bedrooms, 4 full baths, & 1 half bath, including a desirable first-floor bedroom suite ideal for guests, extended family, or an au pair. The main level offers a formal dining room, a stunning chef’s kitchen w oversized island, an open family room w fireplace & powder room. A second living room w fireplace provides additional space for gathering. Two decks off the kitchen and family room overlook the serene backyard. Upstairs are three bedrooms w cathedral ceilings and a dedicated office. The primary suite features a fireplace, custom walk-in closet, spa-like bath with soaking tub and steam shower, & a private deck. The lower level includes a mudroom, full bath, & expansive unfinished space with high ceilings. Abutting conservation land w pond, elevator shaft, A/C & 2 car garage!

23 Whittier Road, Marblehead
$8,900,000
5 Beds ⋅ 7 Baths ⋅ UNDER AGREEMENT Status ⋅ 73514222 MLS ⋅ 8,971 SqFt.
Rarely does a property of this magnitude come to market. From its stunning perch high above the ocean on over an acre of land, this meticulously crafted 14-room Shingle-Style Estate, designed in 2011 by SV Designs and built by Essex Builders, unites artistry, craftsmanship, and panoramic views in a once-in-a-generation offering. Capturing the very best of coastal New England living, this is an architecturally significant residence built for grand entertaining yet shaped by the rhythms of family life. The multi-level floor plan offers 5 bedrooms and 5 full plus 2 half baths across three finished levels, with ocean views from nearly every principal room. Custom millwork, Red Birch flooring, three fireplaces, coffered ceilings, and walls of divided-light windows define the interior; outside, curved fieldstone walls cradle a multi-level bluestone terrace overlooking the open ocean. The setting is irreplaceable, and the ever-changing views are the heart of what makes this home exceptional.

10 West Orchard Street, Marblehead
$1,675,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73513242 MLS ⋅ 3,093 SqFt.
OH CANCELLED ON SUNDAY- OFFER ACCEPTED Nestled on one of Marblehead’s most prestigious streets, this impeccably maintained classic home offers timeless charm and an unbeatable location—close to Glover School, Preston Beach, and Hobb’s playground. Featuring 4+ bedrooms, 2.5 bathrooms, and flexible bonus space on the walk-up third floor and expansive basement, it blends character with functionality. Period details include original hardwood floors, high ceilings, and elegant moldings. The first floor offers a custom mudroom, sun-filled family room addition opens to a chef’s kitchen with soapstone counters, farmhouse sink, and Wolf range, plus a formal dining room, living room with wood stove, and adjoining den. Upstairs includes four bedrooms, newer guest bathroom, and primary suite. Additional highlights: farmer’s porch, two-car garage with workshop, landscaped yard with patio and playhouse. Updates include Andersen windows, Rinnai tankless hot water, updated electrical, garage doors.

39 Clifton Avenue, Marblehead
$1,199,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73512497 MLS ⋅ 2,631 SqFt.
PRICE IMPROVEMENT! Beautiful Single Family in a highly practical, family friendly and sought-after pocket of Marblehead. This spacious 5-bedroom, 3-bath home offers over 2,631 sq ft of versatile living space with potential for an ADU expansion. Attached Garage with 4 car-port parking. Features include an updated kitchen, hardwood flooring, skylit living room with fireplace, dedicated home office, and multiple bonus rooms ideal for guests, gym, media, or flex use. Double sink vanity in every bathroom and kitchen with quartz countertops. Beautiful and private fenced yard designed for entertaining with patio, built-in grill, bar area, gardens, and detached seasonal cottage/studio with electricity. Heated garage plus ample off-street parking. A rare opportunity combining space, functionality, and outdoor lifestyle in one of Marblehead’s most desirable communities. Excellent school proximity. Quick access to top beaches like Deveraux. Come see all this beautiful home has to offer. Come by!

82 Cornell Rd, Marblehead
$2,799,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73497027 MLS ⋅ 3,074 SqFt.
Welcome to 16 Liberty Road—an exceptional 2024 custom home with modern and bright coastal style and post-build high-end upgrades. 4 bedrooms, 3.5 baths, multiple en-suites, plus a dedicated office. Bright, professionally-designed open-concept living with seamless kitchen/dining/living flow—made for entertaining. The lower level delivers a finished space with audiophile in-ceiling speakers plus a separate unfinished area with outstanding storage. Enjoy a fenced yard, refinished mahogany deck, sprinkler system, heated two-car attached garage, and a new custom shed—all on a newly repaved private road. Just two houses from the harbor with beach/dock access, and directly across from Stramski’s Park.

16 Liberty Road, Marblehead
$2,850,000
5 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73486496 MLS ⋅ 4,090 SqFt.
Summer is around the corner ! This SF boasts over 4k sqft of living space, offering a blend of luxury and comfort. The 5 spacious bedrooms have custom or walk-in closets. The 3.5 baths are renovated while the primary ensuite provides a separate shower and double sinks. Upon entering, you'll be captivated by the light-filled rooms, courtesy of oversized windows that capture the sunlight from every direction. The chefs kitchen is a culinary enthusiasts delight, featuring a windowed design, state-of-the-art appliances, 2 sinks, and a copper vented hood. The open layout flows seamlessly into the formal dining room, perfect for hosting dinner parties. The living spaces are elegantly finished with a mix of hardwood floors, accentuated by recessed lighting and a cozy wood burning fireplace. Outdoor living is equally impressive with a heated saltwater gunite in-ground pool, hot tub, and a patio for barbecuing and/or alfresco dining. This home is a haven for relaxation, fitness & entertainment!

59 Harbor Ave, Marblehead
$7,750,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73467958 MLS ⋅ 6,500 SqFt.
Set on 180 feet of beachfront, this rare and highly coveted Marblehead Neck estate offers an extraordinary blend of privacy, scale, and coastal prestige. Encompassing nearly 2-acres of irreplaceable shoreline, the property presents a once-in-a-generation opportunity to reimagine a legacy retreat in one of North Shore’s most exclusive enclaves. This 5 bedroom, 5.5 bath residence captures sweeping ocean vistas, awe-inspiring sunrises, and gentle sea breezes, providing an unparalleled setting for refined coastal living with private beach ownership. Whether the current home is meticulously restored or the site is transformed into a bespoke modern masterpiece, the land itself represents the ultimate in luxury. Expansive and rich with possibility, this estate is a lifestyle investment offering the rare freedom to design a beachfront vision that will endure for generations. For those seeking a premier waterfront acquisition, this property stands as a hallmark of North Shore excellence.

349 Ocean Avenue, Marblehead
$2,650,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73431612 MLS ⋅ 2,736 SqFt.
Perched on spectacular Marblehead Neck, this renovated Victorian blends timeless charm with modern comfort. A wood-burning fireplace, chef’s kitchen with high-end appliances, butler’s pantry, wraparound porch, and new deck set the tone for gracious living. Sunlight fills every room, creating a warm, inviting atmosphere. The first floor offers seamless spaces for gathering, while the second includes four bedrooms—one en suite—plus a full bath and convenient laundry. The third floor is a private retreat with ocean peeks. Enjoy a fenced yard, three-car parking with EV charging, and an unfinished basement (~1,000 sf) and garage ready for your vision. With easy access to Marblehead’s beaches, shops, restaurants, and historic waterfront, this home offers the best of coastal New England living. Schedule your visit today!

4 Ballast Lane, Marblehead

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