Old Saybrook Homes with Contemporary Style

Welcome to Old Saybrook, Connecticut, a charming coastal town nestled in Middlesex County, where history meets modern living. Known for its picturesque waterfront views and rich maritime heritage, Old Saybrook offers residents a unique blend of small-town charm and contemporary convenience. With a vibrant downtown filled with boutique shops, delightful eateries, and cultural attractions, this town is perfect for those seeking a relaxed yet engaging lifestyle.

Old Saybrook is not just a destination; it’s a community that celebrates its heritage while embracing the future. The town is home to stunning parks, scenic beaches, and the iconic Saybrook Point, where the Connecticut River meets Long Island Sound. Outdoor enthusiasts will revel in the abundance of recreational activities, from boating and fishing to hiking along the scenic trails of the nearby preserves.

For those in search of contemporary homes, Old Saybrook boasts an impressive selection of modern residences that cater to today’s discerning buyers. These homes often feature open floor plans, sleek designs, and energy-efficient amenities, providing a perfect backdrop for both relaxation and entertaining. Imagine sipping your morning coffee on a sun-drenched deck or hosting friends in a stylish, airy living space that seamlessly blends indoor and outdoor living.

Whether you’re drawn to the tranquil beaches, the vibrant community spirit, or the allure of contemporary homes, Old Saybrook offers an exceptional quality of life. Discover your dream home in this idyllic town, where every day feels like a vacation.

Newest Old Saybrook Homes with Contemporary Style

$1,163,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188114 MLS

Experience the best of Old Saybrook shoreline living at 96 Ayers Point Road. This exceptional 4/5-bedroom coastal home offers panoramic marsh and Connecticut River views from a private setting with no flood insurance required. Recently painted and designed for effortless indoor-outdoor living, the home features an in-ground gunite pool, an expansive wraparound deck, walls of glass and oversized windows, multiple fireplaces, and a flexible floor plan with a main-level or second-floor primary suite. Rich Saltillo terracotta tile flooring adds warmth, character, and timeless coastal style. Walls of glass fill the home with natural light while framing the ever-changing marsh and Connecticut River views. Spend hours relaxing on the wraparound deck overlooking the peaceful marsh, enjoying spectacular sunsets, abundant wildlife, and tranquil water views, or entertain poolside in your private backyard oasis. The updated eat-in kitchen features new quartz countertops, a 6-burner gas cooktop, and French doors opening to the deck for seamless indoor-outdoor entertaining. A vaulted main level room offers flexible space for a family room, home office, studio, or guest suite. The walkout lower level provides additional living, recreation, or fitness potential. Additional highlights include a new roof, central A/C just over one year old, a 2-car garage, and both gas and wood-burning fireplaces. Minutes from Safe Harbor Saybrook Marina, the public boat launch, beaches, downtown

96 Ayers Point Rd, Old Saybrook

$1,850,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185410 MLS

Contemporary coastal elegance meets exceptional privacy along South Cove in Old Saybrook. Set on an extraordinary 1.8-acre parcel, this cedar-sided, 3,188-square-foot residence offers breathtaking water views from nearly every room and a setting that is virtually impossible to recreate. Originally built in 1965 and thoughtfully rebuilt in 1991, the home was designed to capture its spectacular surroundings with vaulted ceilings, expansive windows, and seamless indoor-outdoor living. The living room showcases custom built-ins, a gas fireplace, wet bar, and sliders to a spacious deck overlooking the cove. The kitchen flows into a well-appointed family room and opens to a 300-square-foot enclosed porch, an ideal space for entertaining and relaxation. The main floor primary suite is a private retreat with soaring ceilings, deck access, stunning water views, dual bathrooms, and an impressive 120-square-foot walk-in closet. A formal dining room, additional bedroom, and separate laundry room complete the first floor. Upstairs, two bedrooms share a Jack-and-Jill bath, providing comfort and privacy for family and guests. Set well back from the road, this exceptional property provides the perfect balance of seclusion and convenience. Whether enjoyed as a year-round residence or a legacy waterfront retreat, the setting offers endless opportunities. Properties of this caliber, acreage, and waterfront presence are extraordinarily rare. A true heritage property and a once-in-a-generation op

108 Maple Ave, Old Saybrook

$999,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24182838 MLS

Welcome to this exceptional 3700 sq ft, move-in ready home, privately situated on a quiet private road and surrounded by landscaped grounds. Set on a beautifully maintained 1.3 acre lot with a lightly wooded backdrop and charming stone wall accents, this property offers the perfect blend of privacy, space, and timeless appeal. The brick exterior creates stunning curb appeal, while inside you'll find a thoughtfully designed floor plan with generous living spaces throughout. The expansive eat-in kitchen features a center island, pantry, abundant cabinetry and counter space, making it ideal for everyday living and entertaining. The bright formal dining room showcases beautiful hardwood flooring, while the formal living room provides additional gathering space. The impressive family room features vaulted ceilings, a wood-burning fireplace, and French doors that open to the picturesque backyard. A sun-filled living room with a second wood-burning fireplace offers the perfect place to relax year-round. The main level also includes a full bathroom and a spacious first-floor bedroom, providing flexibility for guests or multi-generational living. Upstairs, the expansive primary suite offers a private retreat complete with a walk-in closet, dressing area and full en-suite bath. Two additional generously sized bedrooms, including one with a walk-in closet, share a full bath. Convenient upper-level laundry adds to the home's functionality. 2 car attached garage and huge basement.

34 Briarcliffe Trl, Old Saybrook

$2,899,900

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24182941 MLS

Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear Fireplace, Gleaming Hardwoods, Whole House Sound & Security, Irrigation, Super Efficient Natural Gas Heat, Three Car Garage w/ Radiant Floor Heat, On Demand Hot Water, & Custom Built-Ins every where you look! Gourmet Kitchen featuring Floor to Ceiling Double Box Cabinetry, Tile Backsplash, Accent Lighting, Stainless, 1.25" Quartz Counters, Huge Breakfast Island & a 'To Be Jealous For' Chef's Pantry. The Primary Double Floor Suite needs to be seen to be fully appreciated w/ it's Vaulted Balcony Ceilings, Circular stairs that lead to a Private Office & Sitting Room & a Luxurious & Relaxing En-Suite Bathroom! Incredible Bright & Spacious In-Law Apartment w/ a Custom Granite & Stainless Kitchen, Separate Laundry, Hardwoods & Beautiful Light at every turn! Indian Town Beach Association (indiantownassociation. org) is one of the most unique associations in the area w/ it's Golf Cart Friendly Mindset, 3 Beautiful Beaches, 100 Slip Marina, Large Waterfront Clubhouse & a Playground for the Little Ones. It is a great time to buy your Dream Home in Old Saybrook! We are always here to help!

2 Captains Ln, Old Saybrook

$5,900,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24165905 MLS

Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy fireplace, floor to ceiling windows and opens to a 750 square foot inviting deck ideal for relaxing, entertaining, soaking in the hot tub, peaceful sunsets or simply taking in the ever-changing river views. A lower level 750 square foot patio overlooks landscaped grounds, gardens and new stone fire pit area. The chef's kitchen is a dream featuring an oversized granite island, high-end stainless-steel appliances, custom cabinetry, wet bar, wine chiller that invites both gourmet cooking and effortless hosting. Designed for comfort, the home offers multiple luxurious bedroom suites each with sweeping views, spa like bathrooms, walk in closets, hardwood floors and high ceilings. It is perfect for an in-law bedroom or an au pair suite. Spacious additional bedrooms with views, entertainment room, private office with views, a loft, 4.5 bathrooms. A 5-car garage provides ample space for cars, outdoor lawn equipment or storage. A luxury lifestyle experience unlike any other on the Connecticut shoreline.

12 Rocky Point Rd, Old Saybrook

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