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$1,200,000
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24192820 MLS
Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil moldings, authentic hardware and classic 12-over-12 windows. It has been lovingly maintained for decades by a master craftsman and a devoted gardener, with a deep respect for historic properties. Granite steps lead to the entries and there is a brick patio overlooking the grounds. There is an adorable guest cottage which offers wonderful flexibility for visitors, or as an in-law suite or private studio. The beautiful barn/carriage house holds two cars plus a unique blacksmith workshop. The picturesque grounds feature several gardens for seasonal color, mature shade trees, and a fenced vegetable garden area with a charming hand-built garden shed with running water. With its strong history and distinctive architecture, the home is listed on the National Registry of Historic Places. Rarely does a home of this significance become available - offering the perfect balance of history, craftsmanship, natural beauty, and timeless New England charm in a coastal community. The location is also ideal, close to Main St attractions, shopping, restaurants, beaches, and the train station It is almost equal distance to Boston and New York.

170 Old Post Rd, Old Saybrook
$575,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24192318 MLS
This charming home offers the perfect blend of charm, comfort, and opportunity. Filled with warmth, character, and endless potential, this well-maintained home features one bedroom and a full bath on the main level and 3 additional bedrooms upstairs. An inviting open floor plan where the kitchen flows seamlessly into the dining area and family room. The kitchen has granite counter tops, island and double ovens. A cozy living room with a classic fireplace creating the perfect gathering space. Hardwood floors throughout, while the sunroom provides a bright retreat for reading or relaxing. The fully finished basement offers flexible living space ideal for a family room, home office, gym, or playroom. A spacious private yard includes a shed and outdoor shower set on a corner lot is perfect for outdoor barbecues or Summer evenings. Generator ready. Move right in and enjoy its charm while adding your own personal touches over time. Ideally located just minutes from Old Saybrook's vibrant Main Street, boutique shopping, restaurants, marinas, two town beaches, and convenient highway access, this home offers the very best of shoreline living! Come make this home your own!

2 Half Penny Ln, Old Saybrook
$7,500
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191885 MLS
RARE Opportunity to experience a slice of waterfront life on the New England shoreline in quintessential Old Saybrook, CT! This stunning beach-style cape home sits at the mouth of the Connecticut River to Long Island Sound and offers sweeping waterfront views from almost every window! With 3,392 sq ft of tastefully furnished space, this home is perfect for entertaining or enjoying it however you see fit. An open floor plan welcomes you on all 3 floors of the home. Completely updated throughout, the kitchen offers modern amenities with state-of-the-art appliances, including a wine fridge, granite countertops, and custom cabinetry. Vaulted ceilings in the living room help you take in the stunning water view and the natural light that spills in from every angle. And a fireplace is available for cozy New England nights. With 3 large bedrooms, including a primary bedroom with an en-suite bath and walk-in closet, and 3.5 tastefully updated bathrooms, you will never want to leave this oasis! 2 potential office spaces are available to work from home in, utilizing either of the bonus spaces this home has: a family room and rec room! Hardwood floors, central air, newer windows and views you'll never forget! This home is situated at the end of a cul-de-sac and is a two-minute walk to Oak Leaf Marina. Minutes from Rt 9 and Rt 95; close to New Haven and under 2 hours to New York City! Make this rental opportunity yours today!

30 Riverside Ave, Old Saybrook
$585,000
4 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24193207 MLS
A rare opportunity awaits to become the second owner of this lovingly maintained ranch on desirable Schoolhouse Road. Thoughtfully designed for comfortable one-level living, this spacious 2,149-square-foot home offers four generously sized bedrooms, wide hallways, gleaming hardwood floors, and central air conditioning. Step inside to a welcoming living room featuring a classic wood-burning fireplace and oversized windows that fill the space with natural light while overlooking the beautifully landscaped front gardens. The eat-in kitchen is equipped with stainless steel appliances and flows seamlessly into the expansive dining room-an ideal layout for holiday gatherings, dinner parties, and everyday entertaining. One of the home's standout features is the 280-square-foot, four-season sunporch, offering beautiful views of the private backyard and providing the perfect space to relax year-round. It is important to note the this sq. footage is not included in the Tax Record totals for the home. Situated on a picturesque 1.1-acre lot, this property also includes a partially finished basement with plenty of room for storage as well as an attached two-car garage. The home is freshly painted throughout with newly refinished hardwood floors, offering a bright, move-in-ready interior while providing the perfect canvas to make it your own. Offering space, quality, and exceptional care in a sought-after setting, this is a home you'll be proud to call your own.

207 School House Rd, Old Saybrook
$599,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24188934 MLS
Welcome to this classic home with a picturesque setting that is on a generous, level lot, the expansive backyard provides the perfect setting for outdoor entertaining, family gatherings, gardening, or simply relaxing and enjoying the outdoors. The backyard abuts the Old Saybrook preserve offering a private wooded backdrop with access to walking and hiking trails - an ideal setting! This home features four spacious bedrooms, hardwood floors throughout, a welcoming family room, a formal living room, and a dining room ideal for everyday living or holiday celebrations. The kitchen offers granite countertops, stainless steel appliances, and ample space for preparing meals and gathering with family and friends. Additional features include a Buderus furnace, updated electrical, generator ready, full basement offering abundant storage, a two-car garage, and in an area that is ideal for walking and biking. Conveniently located just minutes from two town beaches, marinas, restaurants, shopping, parks, and highways, this home offers the perfect combination of comfort, convenience, and location. Whether you're looking for your forever home or a place to enjoy all that the Connecticut shoreline has to offer, this Old Saybrook gem is ready to welcome its next owners!

22 Beaver Dam Trl, Old Saybrook
$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
$1,649,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24185125 MLS
Nestled within an enclave of distinguished homes in the heart of Old Saybrook, this exceptional residence captures sweeping water views and breathtaking morning sunrises, offering a rare blend of sophistication, and timeless coastal charm. From the moment you enter this light filled home, exceptional craftsmanship and design are evident. Custom millwork defines each space, while rich wood flooring throughout creates warmth and seamless flow from room to room. Newly installed Pella Windows and Doors enhance both beauty and energy efficiency. At the heart of the home lies a beautifully appointed gourmet kitchen, masterfully renovated for both culinary excellence and everyday living. A generous center island anchors the space, complemented by exquisite, honed marble countertops. Premium appliances-including a Sub-Zero refrigerator and professional six-burner gas range are paired with a classic farmhouse sink, bespoke built-ins, and French doors leading to the terrace. The home offers both refined and casual living spaces from the elegant Living-room, centered on a fireplace with French doors leading a covered porch, a formal dining room that's perfect for entertaining and a more casual family room. The luxurious primary suite serves as a private retreat, complete with its own private balcony. Finishing off the second floor are two more spacious bedrooms, each with water-views. Every detail has been thoughtfully curated into one exceptional Package.

5 Cove Lndg, Old Saybrook
$759,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24187238 MLS
Gracious 4 bedroom/ three full baths Cape Cod with an attached two-car garage. Set on a picturesque, one-acre lightly wooded, corner lot with beautiful stone walls, mature plantings, gardens, large patio and an oversized L-shaped in-ground pool which becomes the centerpiece for summer enjoyment complete with lots of privacy. With approximately 2500 square feet of thoughtfully designed living space, the home welcomes you with warmth and character at every turn. The inviting family room, anchored by a charming large fireplace, flows seamlessly into a cook's kitchen designed for both everyday living and entertaining featuring a center island, abundant cabinetry and double ovens. A truly impressive living room showcases extensive built-ins and a second fireplace, creating an ideal space for gathering or relaxing with views to the rear yard and pool. The first floor has one of 2 primary bedroom suites provides 1st floor convenience, multi-generational option or for in-home office space. Throughout the main level, a unique combination of hardwood flooring and inlaid brick adds texture and a subtle historic ambiance. On the second level, you will find three additional generously sized bedrooms and two full baths, providing ample space for family or guests. Whether hosting gatherings or enjoying quiet mornings, this property delivers a lifestyle of comfort, charm and convenience in a highly desirable location, just minutes from town, beaches, restaurants and shopping

2 Pheasant Hill Ln, 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
$1,499,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185199 MLS
Welcome to one of Old Saybrook's most compelling brand-new luxury opportunities. Built by one of Connecticut's premier shoreline designers and builders, this exceptional coastal residence showcases a level of craftsmanship, architectural detail, and thoughtful design rarely found in today's market. Summer is in full swing, and with immediate occupancy and flexible closing arrangements available for qualified buyers, you can still enjoy the very best of the season at Saybrook Point. Perfectly positioned in the heart of this renowned waterfront community, the home offers something increasingly difficult to find along the Connecticut shoreline: brand-new luxury construction, timeless coastal architecture, and an unmatched waterfront lifestyle all without the maintenance, uncertainty, and costly renovations often associated with older shoreline homes. Designed for both everyday living and effortless entertaining, the residence is filled with natural light, soaring ceilings, expansive walls of glass, and carefully curated finishes throughout. The open-concept floor plan flows seamlessly from elegant living spaces into a spectacular chef's kitchen, creating the perfect setting for everything from intimate evenings to holiday gatherings and summer weekends with family and friends.

2 Old S Cove Rd, Old Saybrook
$526,250
3 Beds ⋅ 1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24184175 MLS
Charming Coastal Ranch in an incredible Old Saybrook location! This well-maintained ranch offers the perfect blend of comfort, convenience, and shoreline lifestyle. An easy flow layout which includes 3 bedrooms, living room, dining room, kitchen, full bath and a full unfinished basement for additional storage or workshop. Step outside to a spacious backyard designed for entertaining, relaxing, and enjoying warm summer evenings. This home invites morning walks and evening strolls to Harvey's Beach, Saybrook town beach, Trask Park with a splash pad, and the shops and restaurants along Main Street. Whether you're heading out for dinner, catching the train, or enjoying a beach day, everything you love about Old Saybrook is right at your fingertips. A rare opportunity to own a lovingly cared for home in one of the shoreline's most sought-after areas-perfect as a year-round residence, weekend escape or investment. Come take a look!

9 Farview 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
$850,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24177311 MLS
This beautifully maintained home offers the perfect blend of luxury and comfort! The main level offers exceptional versatility with an open floor plan, hardwood floors, a luxurious primary bedroom suite, along with a living room, family room, gourmet kitchen and formal dining room designed for both relaxed living and elegant gatherings. The first floor primary bedroom suite features California closets, dressing room, cathedral ceilings and a cozy loft. Gourmet kitchen with full pantry, granite countertops, island, stainless steel appliances, a stunning double-sided gas fireplace that creates warmth and ambiance between the main living spaces. Upstairs, a second private primary suite with a walk-in closet, full bath, two additional spacious bedrooms, another full bath, a charming terrace completes the upper level. A walk-up attic offers abundant additional storage, while the full basement and oversized two-car garage provide even more functionality. Surrounded by beautiful landscaping, a spacious deck perfect for entertaining, privacy, on a cul-de-sac minutes from town, beaches and highways.

9 Barley Hill Rd, 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
$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
$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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