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$365,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24187975 MLS
Incredible opportunity to re-imagine the interior of this charming year-round RANCH WITH REMARKABLE VIEWS! Just south of Route 1, this property offers one floor living with wide marsh views. The exterior has been updated and maintained over the last 5-8 years including new vinyl siding, windows, roof, gutters plus a generous sized shed. There is much opportunity here for buyers looking to live in beautiful Old Saybrook - a ranch home with beautiful views along with a canvas ready for renovations. Close to everything ... shopping, restaurants, beaches, Main Street, I-95 and train station for travels.

15 Baum Ave, 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
$1,440,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24173257 MLS
Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first floor, offering even more usable space than reflected. Inside, you'll find a warm and inviting layout highlighted by a vaulted ceiling, large open windows that capture beautiful morning sunlight from the east-facing front exposure, and a cozy fireplace. The first floor features durable ceramic tile, while the second and third floors showcase classic hardwood flooring throughout. Designed for comfort in every season, the home is equipped with oil forced air heating and central air conditioning, with supplemental electric baseboard heating. An oversized septic system, including a 4-bedroom capacity tank, adds peace of mind and functionality. Additional features include new windows, a storage crawlspace beneath the second floor, and thoughtful construction throughout. Knollwood Beach Association residents enjoy exclusive amenities including a private beach, clubhouse, tennis courts, basketball courts, pickleball, and a kayak stand.

21 Fenbrook Rd, Old Saybrook
$940,000
2 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24171224 MLS ⋅ Saybrook Village BLDG.
Step into refined, effortless living in this beautifully appointed luxury condo featuring 2 bedrooms, 2 full baths and 2 half baths. A charming entry welcomes you with a thoughtfully designed garden with roses, lilacs and a variety of other plantings setting a warm and inviting tone. Designed with an open floor plan and soaring cathedral ceilings, the space is filled with natural light and an airy, elegant feel. Rich hardwood floors flow throughout the main living areas, complemented by a cozy gas fireplace that creates the perfect focal point for relaxing or entertaining. The updated kitchen is both stylish and functional, offering corian countertops, stainless steel appliances, a 5 burner gas cook top and seamless connectivity to the dining and living spaces. Sliders lead out to a private patio, ideal for morning coffee or evening gatherings. The first-floor primary suite provides comfort and convenience with a full bath, walk in closet and easy one-level living, while the upper level includes the second bedroom, loft that is being used as an office and additional full bath offering flexibility for guests or a home office. The partially finished lower level includes a sewing room and half bath with plenty of storage space. Ideally situated in a prime location, just steps to Main Street with it's charming shops and restaurants and minutes to local beaches and marinas, this home offers the perfect blend of luxury, convenience and coastal lifestyle living.

25 Sheffield St Unit 7, Old Saybrook
$415,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24169155 MLS
Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from Old Saybrook's stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, you'll find a spacious area that offers endless possibilities-use it as an eating area, a flex office, or even a sleeping space. The open floor plan invites effortless living, with an eat-in kitchen showcasing a center island and newer appliances. Off the kitchen, a slider leads to a spacious back deck, perfect for outdoor dining or soaking in the coastal air. Built-in shelves add both charm and function to the main living area, which also features a convenient first-floor half bath and laundry. Head upstairs to discover a spacious bedroom paired with a full bath featuring a stall shower. The property doesn't stop impressing there-a full basement offers storage or potential, while the flat lot includes a versatile barn/garage and an adorable gazebo perfect for relaxing or entertaining. With public water and an unbeatable location, this home is ready to be your seaside escape or year-round haven. Welcome to the best of Old Saybrook living!

61 Ingham Hill Rd, Old Saybrook
$3,995,000
6 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24162782 MLS
Discover one of the most coveted vantage points on the lower Connecticut River-a mid-century modern sanctuary perched on a private 2.7-acre waterfront peninsula where land, river, and sky converge in perfect harmony. With an extraordinary 875 feet of water frontage embracing both the Connecticut River and the pristine Turtle Creek nature preserve, this property is a haven for bird enthusiasts and wildlife lovers alike. The dual shoreline offers the river side with tidal rhythms and sweeping panoramas stretching from Essex Harbor north to Old Lyme across the water, then south toward Long Island Sound. The marsh side along Turtle Creek hums with avian life-majestic Bald Eagles perch in the trees while Herons, Egrets, Osprey, and migrating songbirds create a symphony that changes with the seasons. Two private docks provide endless boating possibilities: launch from the deep-water river dock for open-water adventure, or drift into the tranquil creek for kayaking and wildlife observation. Inside, 5,536 square feet of light-drenched living space unfolds with effortless grace. The architecture celebrates both gathering and solitude-a chef's kitchen designed for culinary artistry flows seamlessly to indoor and outdoor dining areas, while five fireplaces anchor intimate retreats throughout.

41 Watrous Point Rd, Old Saybrook
$3,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24124699 MLS
Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor bedroom, laundry and bathroom perfect for one floor living. Bright master bedroom suite with cathedral ceiling, sky lights and en suite double vanity bath. Central air conditioning with partially finished basement studio space/built-in bar adds additional living space or a private space for setting up a remote office. Nicely landscaped yard with beautiful plantings and a private patio for dining Al fresco. This shoreline rental home is centrally located on a quiet street just a short walk or bike ride to The Kate, Saybrook Point Inn, downtown Old Saybrook, Harvey's Beach or Town Beach. No matter what your pleasure is ... you're sure to find serenity and tranquility in this beautiful rental home. This Academic Rental property is available from October 1, 2026- April 15, 2027. Schedule Your Private Showing Today!

8 Clinton Ave, Old Saybrook

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