luxury real estate for sale Lakeside Marblehead, United States

Beautifully situated on an oversized corner lot in the desirable third block of Cherry, this charming Lakeside home offers 1,511 square feet of comfortable living space along with the rare convenience of a large attached garage. Thoughtfully designed with two bedrooms and inviting living areas, the home also offers wonderful flexibility for those looking for additional sleeping space. The breezeway and second living area provide options for creating a third bedroom, bunk room, home office or additional flex space to suit your needs.Enjoy the character and ease of Lakeside living with plenty of room to gather, relax and make the most of every season. The generous corner lot provides additional outdoor space, while the attached garage offers sought-after storage for vehicles, golf carts, bikes, lake gear and more. Located on the third block of Cherry, you'll enjoy a wonderful setting within the Lakeside community and easy access to all that makes this special destination so beloved.A terrific combination of location, space, flexibility, an oversized lot and an attached garagefeatures that are not always easy to find together in Lakeside. Subject to the rules and regulations of Lakeside, 99-year land lease and seasonal gate fee.

Charming and full of classic Lakeside character, this original two-bedroom, one-bath cottage offers a wonderful opportunity to enjoy Lakeside living in a great location. Inside, you'll find a spacious living area along with a sleeping porch that adds to the cottage's nostalgic appeal. A welcoming screened front porch is the perfect spot to relax and enjoy summer days in Lakeside. Simple, sweet, and ready for a new owner to bring their vision, this is an opportunity to embrace the charm of an original Lakeside cottage and make it your own. Subject to Lakeside rules and regulations, 99-year land lease, and seasonal gate fee.

Discover endless possibilities with this expansive 6-bedroom, 4.5-bathroom home ideally located on a quiet street near the Grindley Wellness Center and pool. Designed for flexibility and income generation, the upstairs offers its own private entrance and can easily be configured as two separate apartments perfect for short- or long-term rentals. Enjoy your private living space on the main level while generating income from the upper units, or use the entire home as a spacious retreat for a large or multigenerational family. With accommodations for up to 20 guests, this property provides abundant space for gatherings, retreats, or extended stays. Whether you're seeking a personal getaway with income potential or a full investment property, the opportunities are endless. Subject to the rules and regulations of Lakeside, a 99-year land lease, and seasonal gate fee,

Rare opportunity to own one of Lakeside's original Tanneyhill cottages, ideally located on Walnut in the heart of the community. This charming 4-bedroom, 1.5-bath home blends timeless cottage character with thoughtful modern updates, including Hardie board siding, a newer roof, and updated windows. Inviting living spaces create the perfect setting for gathering, while the stamped concrete patio and storage shed offer ideal outdoor functionality. A dedicated parking space just across the street adds convenience, making this a perfect Lakeside retreat with charm, comfort, and an exceptional location. Subject to leasehold land and to Lakeside rules and regulations.

Modern where it matters. Classic where it counts.Welcome to this beautifully updated Lakeside cottage on the desirable 200 block of Sycamore, where timeless charm and modern comfort come together seamlessly. With five bedrooms and three full bathrooms, this home offers generous space for family and friends while preserving the character that makes Lakeside so special.Thoughtful updates throughoutincluding a newer roof, newer windows, and numerous interior improvementsprovide today's conveniences without sacrificing the warmth and authenticity of a classic cottage. Every detail has been carefully considered to maintain its inviting feel while offering peace of mind for years to come.After a day on the lake, rinse off in the outdoor shower before unwinding on the porch and soaking in the charm of Lakeside. Whether you're looking for a seasonal retreat or a year-round residence, this home offers the perfect blend of timeless character and modern comfort.Property is subject to the rules and regulations of Lakeside Chautauqua, a 99-year land lease, and applicable seasonal gate fee.

Welcome to a truly special Lakeside retreat that has been thoughtfully refurbished to combine modern comfort with timeless charm. Offering 6 spacious bedrooms and 4 full bathrooms, this home provides abundant space for extended family and friends to gather, relax, and create lasting memories. Inside, the home showcases modern amenities throughout, including an updated kitchen, fresh finishes, and the convenience of heat and central air. Each room has been refreshed with care, maintaining the character and cozy appeal that makes Lakeside living so unique. Whether you're envisioning large family gatherings, summer getaways, or maximizing the home's terrific rental income potential, this property delivers flexibility and opportunity. Its proximity to downtown means you're never far from Lakeside's vibrant shops, dining, entertainment, and community activities, while still enjoying the peace of your own private haven. Rarely does a property of this size and condition come to market, offering both charm and modern convenience in one. This one won't last long.Subject to Lakeside rules and regulations, 99-year land lease, and seasonal gate fee

Welcome to this extraordinary boater's dream home, located in the exclusive gated Harbor Island neighborhood on Catawba Island. With 244 feet of deep water dockage and a 20,000-pound capacity boat lift, this property is perfect for those who want easy access to the water. Designed for both luxury and entertaining, the home features 4 spacious bedrooms, 5 full baths, and 3 half baths, making it a perfect retreat for family and guests. The two full kitchens, along with expansive exterior decks, create an inviting space for gatherings, while the stunning views of the water provide a tranquil backdrop.The home also boasts a 6-person in-house jacuzzi, 3 fireplaces, and a show-stopping bar. An elevator with a 1400 lb lift capacity makes the transition between entertaining spaces and living quarters seamless.This is truly a boater's paradise, thoughtfully designedfor those who seek both the excitement of the water and the elegance of coastal living on Catawba Island.

Tucked just outside the gates of The Cliffs, this charming single‑story ranch‑style cottage offers the perfect blend of comfort, character, and convenience. Set on a beautifully wooded, double lot, of over half an acre, the property feels like a peaceful retreat while still being close to everything Catawba Island has to offer.Step inside to find a warm, welcoming interior filled with classic touches such as, cove molding, painted wood floors, and a bright sunroom that's ideal for morning coffee, reading, or simply enjoying the view of the green space. This home features three comfortable bedrooms and an updated full bathroom, with a lovely shower, making it easy to settle right in.The kitchen comes fully equipped, with all appliances staying, so you can move in without a worry. Main floor laundry doubles as a mudroom leading out to your deck.Outside, the two‑car detached garage provides plenty of storage for vehicles, tools, or recreational gear, perfect for island living.Cozy, character‑rich, and surrounded by nature, this cottage offers a rare opportunity to enjoy peaceful living in a highly desirable location.

Experience lakeside luxury in this extraordinary Old Homestead home with a private beach and unmatched privacy. This 6-bedroom, 5.5-bath retreat includes two main bedrooms, one on the main level and one upstairseach with spa-like en-suites and enviable closets. A guest apartment above the 4-car garage offers 2 of the 6 bedrooms, a full bath, and a separate entrance, creating ultimate privacy while still connected to the home. Gather in the gourmet kitchen, expansive living spaces, or the screened porch off the dining area. The walkout lower level features a bar, two Murphy beds for guests, and a beachside bathroom for easy rinses after a day on the water. With an elevator and endless space to entertain, this property is a beach front dream come true.