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$21,000,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73539974 MLS ⋅ 7,013 SqFt.
20 Crowninshield Road offers a rare chance to own an exceptional waterfront estate on 2.25 oceanfront acres in one of the North Shore's most coveted settings. Designed to maximize ocean views from nearly every room, this completely rebuilt, six-bedroom residence features six full baths, three half baths, 10-ft ceilings, radiant & central air, a chef's kitchen, private office, and a dramatic ribbon staircase with custom millwork and a seamless coplanar design throughout, offering effortless indoor-outdoor entertaining. An elevator and threshold-free layout offer effortless accessibility. The primary suite offers sweeping water views, 2 gas fireplaces, dual walk-ins, an Ipe deck, and a private outdoor shower. Amenities include a wine cellar, sauna, steam room, pool, grill station, and a hot tub beneath a retractable Ipe deck. Complete with a guest/staff suite, 4-car garage, landscaped grounds, and exclusive access to a neighborhood beach, dock, and mooring. Not in the FEMA flood zone.

20 Crowninshield Road, Marblehead
$2,850,000
5 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73538350 MLS ⋅ 3,900 SqFt.
New construction blends luxury living & idyllic setting for refined coastal living. This distinguished property embodies contemporary design & thoughtful craftsmanship, poised to offer a sophisticated sanctuary w water views fr every room! Chef’s kitchen wows w 36in gas stove & 48in x 9ft kitchen island w 2in quartz counter. Open kitchen/dining/living w oversized ceilings & windows enhances natural setting. Sliders to patio make extended outdoor living easy. Features 3900sf; 5 bedrooms & 4.5bath, 3 full baths ensuite. Spectacular 2nd floor primary suite offers choice btw walk-in closet or office w water views & extraordinary 24x24 deck w unparalleled panoramic ocean views. 1st fl primary option. Large mudroom makes coming in after a day on the ocean a breeze. High-end touches, incl 1st fl tray ceiling, leathered granite on several bath vanities & on LR fireplace w antique mantle. Energy efficient heat pumps & overszed two-car garage w 2 EV charge stations accentuate thoughtful design.

10 Naugus Ave, Marblehead
$849,900
3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73537576 MLS ⋅ 1,778 SqFt.
Welcome to 58 Jersey St, a charming expanded Cape offering the perfect blend of comfort, convenience, and Marblehead lifestyle. Ideally located just a few blocks from downtown, this well-maintained home features 3 bedrooms, 2 full baths, and 1 half bath. The flexible floor plan includes a desirable 1st floor primary suite with a walk-in shower, spacious living & dining room, a comfortable den/family room, and a large eat-in kitchen with updated flooring and beadboard wainscoting. An enclosed 3-season porch extends the living space and opens to the outdoor patio and spacious yard, creating the perfect setting for relaxing or entertaining. Upstairs you'll find 2 additional bedrooms, a full bath, and a bonus craft room or home office. Two off-street parking spaces, abundant storage, and a wooded rear border add to the home's appeal. Enjoy easy access to Marblehead's vibrant downtown, nearby boating access at Stramski Way and Village St docks, and scenic Devereux Beach.

58 Jersey St, Marblehead
$899,000
1 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73536975 MLS ⋅ 725 SqFt.
Unmatched harbor views and the best of Old Town Marblehead at your doorstep. This beautifully renovated 1-bed, 1-bath condo captures sweeping vistas of Marblehead Harbor, the lighthouse, and the Atlantic from one of the town’s most coveted waterfront settings. Soaring ceilings and an open-concept layout create a bright, airy living space, with kitchen, dining, and living areas all oriented to the water. Step out to a spacious private deck perched above the harbor, offering a front-row seat to sailboats and ever-changing coastal scenery. The bedroom provides a quiet retreat, complemented by an updated bath with timeless finishes. Additional features include in-unit laundry, 1 deeded parking spot, private outdoor spaces & more. Just steps to Crocker Park, Fort Sewall, shops, restaurants, and historic Old Town. Rare opportunity to own one of Marblehead’s most spectacular harbor front residences—the final available unit in this fully renovated, owner-occupied 7-unit building.

95 Front Street Unit 1, Marblehead
$1,195,000
3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73536947 MLS ⋅ 1,710 SqFt.
Located in a desirable neighborhood just minutes to the beach, this classic Colonial offers beach rights, ample off-street parking with both upper & lower driveways, proximity to downtown Marblehead, and convenient commuter access. Filled with natural light, the home features 3 bedrooms & 1.5 baths. The front-to-back living room is anchored by a wood-burning fireplace with a charming Delft tile surround, creating a warm and inviting gathering space. A formal dining room flows into the kitchen, which offers a peninsula with seating, generous cabinetry, and ample workspace. A half bath and bright three-season sunroom complete the first floor. Upstairs are three generously sized bedrooms, a full bath, & attic access for additional storage. The spacious basement includes a washer & dryer & provides excellent storage space. An attached 1-car garage is ideal for a compact vehicle, beach gear, bicycles, kayaks, and more. A wonderful opportunity to enjoy Marblehead’s coastal lifestyle.

3 Vassar Road, Marblehead
$339,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73536925 MLS ⋅ 583 SqFt.
Enjoy the best of Marblehead living from this bright and inviting one-bedroom condominium ideally located in the heart of downtown. A perfect unit for investment, first time homebuyer or summer getaway. Featuring high ceilings, oversized windows, and abundant natural light, this well-maintained home offers an open and airy feel throughout. The updated kitchen and bathroom blend modern convenience with timeless appeal, while hardwood floors and generous closet space add to the comfort and functionality of the unit. The unit comes with 1 car parking. Perfectly situated between Marblehead's Historic District and vibrant downtown area, you'll enjoy easy access to restaurants, shopping, theaters, historic landmarks, Marblehead Harbor, and the Rail Trail. A wonderful opportunity to own in one of Marblehead's most desirable and walkable locations.

83 Pleasant St Unit 3, Marblehead
$1,450,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73536824 MLS ⋅ 3,074 SqFt.
Contractors! Investors! Family Home owners looking for a fix-er-upper to flip or live in! Enjoy seasonal ice skating, fishing and model boat racing on Redd's Pond. Fabulous opportunity to create the home of your dreams on this corner lot. Elevated private patios allow for ease of grilling and relaxing. Second floor bedroom at 6 Calthrope has separate exterior entrance. Second floor above 2 car garage has finished studio/bath/kitchenette with separate entrance and private patio. Roofs on both dwellings are 6 years old as well as paved parking area near garage. Oversized paved driveway on left of garage affords bonus parking or storage. So worth the effort to renovate or rebuild on this corner lot. Wonderful location and just waiting for you to come and imagine the possibilities for all your needs. Bonus factor: Unrestricted zoning classification per town records!! Shown by scheduled appointments only!

6 Calthrope/2 Togan Way, Marblehead
$295,000
1 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73536553 MLS ⋅ 530 SqFt.
Enjoy the best of Marblehead living from this charming 1-bedroom condo privately situated in the rear of a classic 1880 building in downtown Marblehead. Tucked away from the street yet just steps from shops, restaurants, Marblehead Harbor, Crocker Park, and Fort Sewall, this home offers a rare combination of privacy, parking, and potential. Inside, you'll find hardwood floors, built-in shelving, abundant natural light, and an efficient layout full of character. Rarely found in this location, the property includes two deeded off-street parking spaces, exclusive-use deck space, and a detached outbuilding with expansion potential. Whether used for storage, a workshop, studio, home office, or future improvement project (subject to approvals), the outbuilding offers flexibility seldom available at this price point. An exceptional opportunity for a primary residence, weekend getaway, or investment property in the heart of downtown Marblehead.

21 Hawkes St Unit 5, Marblehead
$15,000,000
5 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73536454 MLS ⋅ 9,586 SqFt.
This magnificent oceanfront estate stands as one of the most significant properties in Marblehead. Located in the exclusive Peach’s Point neighborhood, this property offers stunning views of Crowninshield Island, Grace Oliver’s Beach, Marblehead Lighthouse, and the surrounding islands. “Seaside Farm” replaced the original Crowninshield estate in 1999 in a classic Georgian style, with meticulous attention to detail throughout. The home is designed to maximize ocean views while maintaining privacy. The grand 2-story foyer with a custom staircase sets the tone for the home, which features elegant living spaces ideal for both daily life and entertaining. The second floor includes an oceanfront primary suite with a fireplace, walk-in closet, modern bathroom, and a private deck with exceptional views. Three additional en suite bedrooms, a large office, and a laundry room complete the second floor. Caretakers 1 bedroom apartment over 4-car garage offering views of Grace Oliver's Beach and c

17 Crowninshield Road, Marblehead
$539,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73535563 MLS ⋅ 705 SqFt.
Beautifully designed two-bedroom, one-bath condo blending modern style with everyday comfort. Enter through your private direct-access entry into a mudroom with a jacket closet, shoe storage, and in-unit laundry. The open-concept living area features hardwood floors, recessed lighting, and oversized windows that bring in abundant natural light. The sleek kitchen offers quartz countertops, stainless steel appliances, a gas range, and modern cabinetry. The contemporary bath includes a designer vanity, illuminated mirror, and tiled shower. Additional highlights include central heat and A/C and efficient new systems throughout. Located steps from Marblehead’s shops, restaurants, and historic harbor, this home offers modern living in one of the North Shore’s most desirable communities.

290 Washington St Unit B, Marblehead
$775,000
3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73535331 MLS ⋅ 2,816 SqFt.
Comfort, versatility, and room to grow define this inviting ranch on a fully fenced quarter-acre lot with established gardens and a spacious level yard. The main level offers easy one-level living with 3 bedrooms, a full bath, and 1,408 square feet of living space. The above-grade walkout lower level mirrors the main level with an additional 1,408 square feet and a second full bath, providing exceptional flexibility for future living space, including a family room, home office, fitness area, workshop, hobby space, or guest retreat. Outside, the three-tier deck with low-maintenance composite flooring is perfect for entertaining or relaxing. An attached one-car garage and storage shed add everyday convenience. Lovingly maintained and full of potential, this home is ready to be reimagined for today's lifestyle.

3 Countryside Lane, Marblehead
$1,949,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73523180 MLS ⋅ 3,200 SqFt.
Stunning Modern Colonial new construction in a desirable Marblehead location offering approx. 3,200 sq ft of thoughtfully designed living space. This 4-bedroom, 4-bath home features an open-concept main level with 9 ft ceilings, white oak hardwood floors, oversized black-framed windows, and abundant natural light. The chef’s kitchen includes quartz countertops, a large center island, custom cabinetry, stainless steel appliances, and designer lighting, flowing seamlessly into the dining and living areas. The living room is anchored by a beautiful fireplace wall. The second level offers a spacious primary suite with a well-appointed bath featuring a soaking tub, tiled shower, and matte black fixtures, plus additional bedrooms and full baths. Finished lower level provides flexible space for a media room, gym, playroom, guest area, or home office. Complete with classic curb appeal, 1-car garage, EV charging, and convenient access to beaches, downtown, schools, and commuter routes.

98 Evans Rd, Marblehead
$4,250,000
4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73532365 MLS ⋅ 3,700 SqFt.
Meticulously renovated oceanfront residence in the prestigious Greystone neighborhood offering sweeping panoramic views from Marblehead Harbor to Boston. Newly reimagined state-of-the-art kitchen features stainless steel appliances, custom cabinetry, a spacious center island, and a sunlit breakfast nook—perfect for both everyday living and entertaining. The main level is open-concept, connecting the kitchen and dining room, a spacious living room with a fireplace and a bright sunroom. The second floor leads to a dramatic primary suite with cathedral ceiling, oceanfront deck and a new beautifully appointed modern bathroom. Two additional en-suite bedrooms complete this level, both with new updated bathrooms. The lower level walks out to the lawn with hot-tub or to the steps down to the ocean. This level includes a generous family room with a stone fireplace, an area for a home office, a dedicated exercise area, a fourth bedroom, a new modern bathroom and laundry room.

16 Coolidge Road, Marblehead
$899,000
3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73532191 MLS ⋅ 2,375 SqFt.
10 Charlotte Road offers a rare opportunity to own a beautifully maintained classic home filled with character, charm, & endless potential. Built in 1936, this gracious home features over 2,300 square feet of living space w generously proportioned rooms, hardwood floors, detailed millwork, & an abundance of natural light throughout. The welcoming floor plan includes spacious living & dining areas designed for comfortable everyday living & effortless entertaining. A bright eat-in kitchen overlooks the yard, while large bedrooms provide flexibility for family, guests, or work-from-home needs. Thoughtfully cared for over the years, it offers the perfect canvas for buyers looking to blend timeless architecture w their own vision & updates. Set on a beautifully landscaped corner lot, the property is complemented by a detached two-car garage, expansive driveway, and mature plantings that create exceptional curb appeal. Centrally located & moments to Tedesco Country Club, shopping & schools.

10 Charlotte Road, Marblehead
$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 ⋅ CONTINGENT 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
$1,945,000
3 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73523769 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 Street 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
$749,000
2 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73521527 MLS ⋅ 1,718 SqFt.
Your own Private Elevator!!!! Beautiful Townhouse Near Stramski Beach!This stunning 2-bedroom, 2.5-bath luxury townhouse combines coastal charm with modern comfort. The bright, open-concept design features gleaming hardwood floors and soaring ceilings that connect the living, dining, and kitchen areas—perfect for entertaining. The chef’s kitchen boasts quartz countertops, stainless steel appliances, and an oversized gas range. Each bedroom includes its own full bath while the private elevator provides effortless access from the two-car garage—to all 3 levels. Laundry is conveniently located on the second floor, and custom window shades add a finishing touch. Centrally located near beaches, parks, and shops, this exceptional townhouse offers easy access to all the North Shore has to offer. Experience coastal living at its finest! Comfortable front porch. Great workshop...and guest parking onsite. Bring your toothbrush not your tool belt :::)))

155 Green Street Unit 4, 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
$975,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73515675 MLS ⋅ 1,443 SqFt.
"THE ELBRIDGE" is an exclusive development located in a stately 120-year-old brick building. Combining modern amenities with antique charm,high ceilings and oversized windows, this light filled 2 bedroom,2.5 bath townhouse features a main floor with a large open space combining the living room , dining area and the chef's kitchen -complete with a central island, quartz countertops, top of the line stainless appliances and custom floor-to-ceiling cabinets. There are two ensuite bedrooms,in-unit laundry, central A/C, and dedicated parking, plus an outside patio. 20 Mechanic Square is walking distance to Marblehead's famous harbor and central Landing,2 yacht clubs, several seaside parks, beaches, plus 2 islands(at low tide!),and only a few blocks to downtown boutiques, coffee shops,a grocery store, restaurants, museums and theaters. Once you arrive home you can park your car, leave the keys, and enjoy all that Marblehead has to offer. Ideal for either summer or year round living.

20 Mechanic Sqaure Unit 3, Marblehead
$1,150,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73515676 MLS ⋅ 1,965 SqFt.
"THE ELBRIDGE" is an exclusive development located in a stately 120-year-old brick building. Combining modern amenities with antique charm,high ceilings and oversized windows, this light filled 2bedroom,2.5bath townhouse features a main floor with an open living room and dining area and a chef's kitchen-complete with a central island,quartz countertops, top- of- the line stainless appliances and custom floor to ceiling cabinets. There is an ensuite bedroom on this level plus a second ensuite bedroom on the lower level as well as a family room or office & laundry room.The unit has central A/C and dedicated parking.20 Mechanic Square is walking distance to Marblehead's famous harbor and central Landing, 2 yacht clubs, several seaside parks, beaches, plus 2 islands(at low tide!), and only a few blocks to downtown boutiques, coffee shops, a grocery store, restaurants, museums, and theaters. Arrive home & enjoy all that Marblehead offers

20 Mechanic Square Unit 2, 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

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