57 houses for sale in Caddy Shack Square

The Ultimate Lakeside Cottage: A One-of-a-Kind architectural masterpiece. This sprawling 5,362 sq ft retreat (3,724 livable) has been meticulously reimagined & expanded to create two complete living spaces with optional separate entrances. This creates significant flexibility for family & guests to create Lakeside memories! The addition boasts its own kitchen & eating area. Relax in the breathtaking great room with a gorgeous 16-foot stone fireplace. A charming loft bedroom overlooks the space. Off the luxurious master bedroom & bath, enjoy a cup of coffee on the covered deck that overlooks pickleball and tennis courts & the pool. Plenty of sleeping space on the first & second floors. The original cottage has been masterfully rebuilt to seamlessly coordinate with the new addition. Inside, no detail was spared: all new doors, granite countertops in the kitchen. Enjoy modern comforts throughout: ceiling fans, newer appliances, newer gas furnaces & air conditioners. Let's not forget the 3

Spacious, versatile, and ideally located, this exceptional 5-bedroom, 3 full bath home offers the space and flexibility rarely found in Lakeside. Situated on a gorgeous double lot, the property features abundant outdoor space, off-street parking, and an attached 2-car garage all highly sought-after amenities within the gates. Inside, the home offers multiple living and gathering spaces perfect for hosting family and friends. A unique layout provides the potential for a private guest retreat or separate living quarters with its own entrance, creating incredible flexibility for extended stays, guests, or multi-generational living. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this property delivers the ideal combination of charm, functionality, and location. Enjoy close proximity to the lakefront, parks, shopping, dining, and all that Lakeside has to offer while enjoying the privacy and space of one of the area's most desirable lot confi

New price! Lakeside lakefront! Don't miss out on this waterfront cottage with spectacular panoramic views of the lake from both floors! The screened front porch is the perfect welcome, ideal for morning coffee or unwinding at sunset. Upstairs, an enclosed second-floor porch provides a cozy retreat with outstanding, uninterrupted views of the lake! Inside, the cottage exudes warmth and simplicity, with a large living room and a separate dining room (currently used as a bedroom) for family and friends to gather. Featuring 4 bedrooms & 1.5 baths, this charming cottage offers comfortable living for family and guests alike. Ideally situated just steps from the park, shuffleboard courts, shopping, dining and the pier. A low-maintenance cottage featuring outdoor storage sheds, a reserved parking space and minimal lawncare. New windows installed in 2022. Start making lasting memories in this inviting lakefront cottage! Rules & Regulations of Lakeside apply, including 99-year land lease, and se

Welcome to 715 Cherry Avenue in the heart of Lakeside Marblehead, where you can enjoy the charm, walkability, and waterfront lifestyle of Lakeside without the assessments. Perfectly positioned just outside the gates of Lakeside, this rare opportunity offers the best of both worlds. Enjoy access to the vibrant community and attractions while maintaining flexibility, true ownership, and the ability to rent, which is a highly sought after advantage in this area. This 3 bedroom, 2.5 bathroom home sits on an expansive triple lot parcel, providing space, privacy, and potential that is nearly impossible to find this close to Lakeside. The property features a large attached heated garage, a charming sunroom breezeway ideal for relaxing after a day on the water, and an upper bonus room with additional storage that is perfect for a 4th bedroom, a home office, or additional entertaining space. New flooring throughout the kitchen and living room spaces, newer deck, new storm door, and MORE! Step o

If you've been waiting for a beautifully built home in Lakeside, this is the one. Ideally located on the desirable 300 block of Plum, this thoughtfully designed four-bedroom, two-bath home blends quality craftsmanship with the charm that makes Lakeside so special. Built with exceptional attention to detail, the home features carefully selected finishes, light-filled living spaces, and a well-designed floor plan that feels both comfortable and inviting. Designed for year-round living, it offers plenty of space for family and guests while still maintaining an easy, low-maintenance lifestyle. A wonderful opportunity to own a beautifully crafted, newer home in the heart of Lakeside. Property is subject to the rules and regulations of Lakeside, including the 99-year land lease and seasonal gate fee

RECENTLY REDUCED Built in 2006 and cherished by its original owners, this spacious home offers comfort and character in every corner. The sun-filled living room features an electric fireplace and abundant windows, while the open-concept kitchen includes a large island, ample storage, and a cozy dining space. Step out onto the 8x8 deck just off the kitchen-perfect for outdoor dining or relaxing in the backyard. Nearby, you'll find a full bathroom with a step-in shower and an adjacent flexible room that could serve as a guest bedroom or home office. Upstairs, the primary suite includes its own full bath and large closet. There are two additional full bathrooms on the second floor. Roomy closets are in every bedroom. On the third floor, two versatile rooms offer extra space, one of which includes a convenient half bath. The oversized two-car garage is well-equipped with shelving, and the beautifully landscaped yard is framed by hand-laid rock walls in both the front and back. Located in t

ONCE in a Lifetime, you can enjoy the Supreme Quality of a Post & Beam Amish home! One-of-a-Kind Design with the artistic finishes of true Craftsmen. Various types of wood enhance the warmth of the interior, featuring a magnificent Hickory Kitchen and Open Floor Plan. A Stunning two-story living room draws you in to enjoy the spectacular Stone Fireplace. The Ground floor Owners Suite offers a walk-in shower on the main floor. Guests can enjoy the views as they traverse the elegant Hickory Staircase to the guest rooms! Beautiful and Historic, Gem Beach has drawn families for generations to enjoy the unique Sunrise, Sandy Beach, the Island Views and nearby amenities, the endless fishing, the nearby Catawba Island Club, the Ferry to the Islands. Short trip and you can enjoy Cedar Point and Water Parks. Make this Your'place at the Lake'