Old Saybrook Homes for Sale

Old Saybrook Homes for Sale

Welcome to Old Saybrook, Connecticut—a charming coastal town that beautifully blends rich history with modern living. Nestled in Middlesex County, Old Saybrook is a gem of New England, offering breathtaking views of the Long Island Sound and the Connecticut River. This picturesque town is steeped in history, with roots dating back to the 1600s, making it one of the oldest settlements in the state. Strolling through its tree-lined streets, you’ll encounter a delightful mix of colonial architecture and contemporary homes, all set against a backdrop of stunning natural beauty.

Old Saybrook boasts a vibrant community atmosphere, where residents enjoy a plethora of outdoor activities, including boating, fishing, and hiking in nearby parks. The town is home to several beautiful beaches, perfect for soaking up the sun or enjoying a leisurely stroll along the shore. With an array of local shops, art galleries, and restaurants featuring fresh seafood and farm-to-table cuisine, there’s always something to explore.

For those considering a move, Old Saybrook offers a diverse selection of homes for sale, from quaint cottages to luxurious waterfront properties. Whether you’re a first-time homebuyer or looking for a serene retreat, you’ll find a variety of options to suit your lifestyle. The real estate market here is thriving, with properties that reflect the town’s unique character and charm.

Embrace the coastal lifestyle and discover your dream home in Old Saybrook—where history, community, and natural beauty come together to create an idyllic living experience. Explore our listings today and take the first step toward making Old Saybrook your new home!

Newest Old Saybrook Homes for Sale

39 Dudley Ave, Old Saybrook
$695,000
2 Beds ⋅ 2 Baths ⋅ 24220077 MLS
Would you like to be in your new home for the holidays! In town location with beautiful gardens and manicured grounds. Cape Cod style house with an abundance of charm and character. From the moment you enter and experience the Living room with archways, wood floors and builtins you will feel the warmth and love this house has to offer. Many updates including newer boiler, roof and exterior siding. Upgraded electrical service. Short distance to Founders Park to enjoy the serenity and views that help define the wonderful community of Old Saybrook. Enjoy the Main Street shopping district and "The Kate" for top notch entertainment. This opportunity is ready for your next chapter.

39 Dudley Ave, Old Saybrook
135 Ayers Point Rd, Old Saybrook
$739,900
3 Beds ⋅ 2 Baths ⋅ 24220541 MLS
Discover the charm of Old Saybrook in this custom-built brick ranch-style home, offering warmth, character, and a wonderful connection to nature. This inviting home features three bedrooms, a spacious living room, formal dining room, eat-in kitchen and sunroom providing comfortable living spaces with plenty of potential to make your own. Ideally situated near the beautiful Connecticut River, the property is just minutes from Turtle Creek Preserve, a 96-acre protected natural sanctuary featuring scenic trails and peaceful river views. For the car enthusiast or hobbyist, an oversized detached two-car garage offers plenty of room for vehicles, equipment, and additional storage. Recent improvements include a propane-powered house generator, central air conditioning, and new well. Enjoy the best of both worlds- a peaceful natural setting with a charm and convenience of everything Old Saybrook and the Connecticut Shoreline have to offer. A wonderful opportunity to make this special property your own. Call-Show-Sell. Thank you for all showings.

135 Ayers Point Rd, Old Saybrook
7 Cromwell Ct, Old Saybrook
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 24218911 MLS
This stunning Colonial, nestled in the peaceful North Cove neighborhood of Old Saybrook, offers an exceptional blend of timeless charm, refined living, and an enviable location. Just moments from the Village, enjoy convenient access to an array of restaurants, boutique shopping, and scenic walking and biking opportunities. The thoughtfully designed interior is highlighted by a custom kitchen featuring high-end appliances and a separate breakfast area. The adjoining family room, complete with a fireplace, opens through sliders to lovely screened porch, creating a seamless transition to the outdoor pool complex-perfect for both relaxation and entertaining. The spacious primary suite offers a beautiful bath and ample closet space, while three additional bedrooms provide comfortable accommodations for family and guests. A remarkable property in a sought-after location, this exceptional home is not to be missed!

7 Cromwell Ct, Old Saybrook
3 Town Beach Rd, Old Saybrook
$839,000
4 Beds ⋅ 3 Baths ⋅ 24217096 MLS
Enjoy the best of shoreline living in this newly renovated four-bedroom home located in the sought-after Cornfield Point community of Old Saybrook! Featuring a bright, open floor plan, with a new kitchen, new stainless steel appliances, new split systems, new hot water heater, and a new deck. First floor bedroom, a full bath and laundry are all located on the main floor. This inviting home offers a wonderful blend of modern updates, comfortable living, and coastal charm. The open layout creates an ideal setting for entertaining family and friends, while four bedrooms provide plenty of space for guests and everyday living. As a member of the Cornfield Point Beach Association, you'll enjoy an exceptional array of community amenities, including beautiful beaches, a boat launch, a tennis court, a clubhouse, and a playground. Experience the relaxed coastal lifestyle that makes Cornfield Point such a special place to call home. Whether you're looking for a year-round residence, a shoreline getaway, or a place to make lasting family memories, this updated home is an opportunity not to be missed!

3 Town Beach Rd, Old Saybrook
7 Toms Rd, Old Saybrook
$1,200,000
2 Beds ⋅ 1 Baths ⋅ 24216468 MLS
2 Plots sold together- 7 & 18 Toms Rd. Rare opportunity to own a slice of CT shoreline! Tucked away at the end of a private road, this charming seasonal waterfront cottage offers water on 2 sides, water views on 3, private beach, backyard dock & breathtaking sunsets. Cherished by the same family for generations, this special coastal retreat captures everything there is to love about beach living. Recently refreshed with new flooring, new granite counters, new hot water heater and electrical updates. The cottage features an inviting open floor plan, flexible sleeping accommodations with convenient convertible beds & a spectacular enclosed front porch where you can relax, entertain & take in the waterfront scenery. Spend your days swimming, kayaking, paddleboarding, or simply enjoying the sand & sea breeze. An outdoor shower makes rinsing off after a day at the beach a breeze. The property includes both front & back lots, offering a unique waterfront setting with room to enjoy the outdoors. Conveniently located near Harvey's Beach & all that Old Saybrook has to offer, this property presents an incredible opportunity for a personal summer getaway, a family retreat, or a seasonal rental investment. Currently winterized & ready for its next chapter, this is your chance to create lasting shoreline memories in a truly special location. Come experience the sunsets, salty air, and laid-back beach lifestyle.

7 Toms Rd, Old Saybrook
2 Hawk Brk, Old Saybrook
$900,000
3 Beds ⋅ 3 Baths ⋅ 24215827 MLS
Very private location yet close to major commuter routes, this wonderfully maintained Colonial has large living spaces inside & out! Entry foyer w/2 oversized closets, tile flr and access to huge 2 car garage. The 1st flr features a huge eat-in kitchen w/rich cherry cabinetry, center island w/downdraft range, tile & hdwd floors, spacious pantry closet & access to the 16.5x24 back deck perfect for relaxing & dining. The formal DR is perfect for that special meal and the formal living rm has a cozy wood burning brick fireplace & hearth-both rooms have gleaming hardwood flrs. The 19.5x24 ft family room is a breathtaking space featuring soaring vaulted ceiling, hdwood flrs w/walnut inlay, oversized Palladian window & rear bay window. A full bath rounds out flr 1. The 2nd flr features a Master Suite comprised of huge BR, laundry room, full bath w/soaking tub and bidet, dressing area w/ample closets & spacious sitting rm. The remainder of the 2nd flr features 2 more well-proportioned BRs accompanied by a full bath w/tub-shower combo & tile flr. There is a full walkout basement w/partially finished 19.5x25 room w/French doors leading directly to the backyard. There is also an enormous walk up attic with soaring ceilings that will hold all your treasures or could be finished for even more living space. Oil hot water heat & a 2 zone central air conditioning system will keep you comfy all year. There is a Central Vac & whole house generator so you always have peace of mind. Come see

2 Hawk Brk, Old Saybrook
14 Cinnamon Rdg, Old Saybrook
$625,000
3 Beds ⋅ 3 Baths ⋅ 24217273 MLS
Photos uploaded!! Available to be shown 10/31 --- NEW LISTING in beautiful Cinnamon Ridge! This OH-SO charming cape set on a picturesque, very private 1+/- acre lot has undergone several wonderful transformations with fresh paint, newer windows, Buderus boiler, newer water heater, newer floors and carpets, along with stunning kitchen and baths with gorgeous cabinetry, granite countertops, stainless steel appliances including a beverage/wine refrigerator. The entry foyer is bright with full-lite front door and skylights, coat closet and new half bath; the front to back family room has a fireplace for cozy fall-time fires and french door to large 40x14 deck; both the dining room (also with french door to deck) and the living room have beautiful hardwood floors. On the second floor is the Primary bedroom complete with it's new personal bath; two additional bedrooms plus the main bath also newly remodeled. Beautiful drive along Cinnamon Ridge with trees laden with fall leaves ... Don't miss this once-in-while opportunity to be in one of Old Saybrook's prime locations - off country roads yet close to all that Old Saybrook has to offer -- town parks, beaches, quaint Main Street, The Kate theater, restaurants, shopping, train station etc.

14 Cinnamon Rdg, Old Saybrook
514 Main St, Old Saybrook
$2,495,000
4 Beds ⋅ 4 Baths ⋅ 24197382 MLS
Welcome to 514 Main Street, a waterfront custom-crafted home built in 2006 with unobstructed, expansive views of North Cove. This coastal-inspired retreat blends sophisticated elegance with everyday functionality. Boasting 3,766 square feet, this home has 4-bedrooms, 3.1-baths with an open-air concept that centers around a spectacular great room, setting the stage for seamless entertaining and comfortable daily living. Steeped in high-end finishes, the main level features an expansive chef's kitchen equipped with granite countertops, a large island, a dedicated walk-in pantry, separate bar/prep sink and double wall ovens. It transitions effortlessly into the dining area, which opens onto a tranquil screened porch directly overlooking North Cove-your future favorite spot for morning coffee or relaxing summer evenings. The highly desirable first-floor layout includes a luxurious primary master suite complete with a spa-like bath. Ideal for modern remote work, the main level offers a dedicated home office plus a separate quiet study. Upstairs, the home continues to impress with a playroom/rec room outfitted with custom built-in bookshelves. Tucked away on yet another level is a unique "Crow's Nest"-a perfect reading nook or a great space for a spin cycle with an amazing view of both North and South Coves. Complete your day with your favorite beverage on the balcony, watching the sailboats as they return to their moorings in the protected cove.

514 Main St, Old Saybrook
11 Kitteridge Hill Rd, Old Saybrook
$679,000
3 Beds ⋅ 3 Baths ⋅ 24216599 MLS
Discover the charm and comfort of this beautifully maintained Cape, ideally situated on a quiet cul-de-sac off School House Road in one of Old Saybrook's desirable locations. Offering over 2,700 square feet of finished living space, this inviting home is just across from The Preserve trail access and moments from Clark Park, making it easy to enjoy nature, recreation, and the outdoors. Inside, gleaming hardwood floors, a spacious living room with a wood-burning fireplace, and a formal dining room create a warm, welcoming atmosphere. The updated kitchen features rich cherry cabinetry and granite countertops and opens to a cozy family room with a Garrison wood stove. Sliders lead to a cedar-paneled three-season room overlooking the private backyard, deck, and patio-perfect for entertaining or relaxing outdoors. Upstairs, the spacious primary suite features an en-suite bath with a custom shower and tons of storage, along with two additional bedrooms and a full bath. The finished lower level offers flexible space for a home office, gym, media room, or additional living area. Thoughtful updates include Andersen replacement windows, newer garage doors, enhanced attic insulation, and ice dam heating cables. Blending classic New England charm, versatile living spaces, and an exceptional location near trails and recreation, this move-in-ready home is a wonderful place to enjoy the best of Old Saybrook living.

11 Kitteridge Hill Rd, Old Saybrook
121 Bokum Rd, Old Saybrook
$574,000
1 Beds ⋅ 1 Baths ⋅ 24212897 MLS
Escape to your own private country retreat along the beautiful Connecticut shoreline! Nestled on over two acres of gorgeous, level land, this newly renovated 1,100-square-foot home offers a rare opportunity to enjoy the serenity of country living with all the conveniences of Old Saybrook just minutes away. Imagine creating magnificent gardens, hosting summer gatherings and picnics on the expansive lawn, or simply relaxing with your favorite book surrounded by nature. There's plenty of room for pets to play, outdoor hobbies, and perhaps even a horse, subject to town approval. The beautifully refreshed home offers comfortable, easy living, whether as a full-time residence, charming weekend escape, or potential income-producing Airbnb. With over two acres of usable land, the possibilities for creating your own personal sanctuary are truly exciting. Enjoy peaceful mornings, star-filled evenings, and the luxury of space and privacy, all within easy reach of beautiful beaches, marinas, waterfront dining, boutique shopping, and Amtrak service connecting to New York and Boston. Perfect for those seeking a relaxed lifestyle away from the hustle and bustle, this special property offers the best of country and coastal living. A wonderful opportunity to enjoy the shoreline on your own terms!

121 Bokum Rd, Old Saybrook
21 Fenbrook Rd, Old Saybrook
$1,190,000
3 Beds ⋅ 3 Baths ⋅ 24211568 MLS
Welcome to easy year-round coastal living in the desirable Knollwood Beach Association! Ideally located near a beautiful private sandy beach. this spacious home offers the perfect opportunity for a full-time residence, weekend getaway or shoreline retreat. The bright, inviting interior features a vaulted ceiling, fireplace and large east-facing windows that fill the home with morning sunlight. Offering approximately 1,916 square feet of finished living space, including a finished above-grade lower level, the home provides plenty of room for family and guests. Ceramic tile enhances the lower level, while hardwood flooring extends throughout the upper floors. Comfort is assured year-round with oil forced-air heat, central air conditioning and supplemental electric heat. Additional features include newer windows, useful storage and an oversized septic system with a 4-bedroom capacity tank. Best of all is the Knollwood lifestyle! The association is situated on approximately five acres and offers a private beach, clubhouse, pickleball, tennis and basketball courts, playscape and sea kayak storage/stand. Enjoy morning walks by the water, beach days with friends and family, kayaking and an active coastal lifestyle-all just minutes from Old Saybrook's Main Street, restaurants, shops and amenities. A wonderful opportunity to enjoy the Connecticut shoreline in every season.

21 Fenbrook Rd, Old Saybrook
12 Drummers Trl, Old Saybrook
$995,000
4 Beds ⋅ 4 Baths ⋅ 24211855 MLS
LONG ISLAND SOUND VIEWS,2.02 PRIVATE ACRES & EXCEPTIONAL CONDITION!Perched on a sunny hilltop, this beautifully maintained Colonial Contemporary offers approximately 3,300 sq. ft. of thoughtfully designed living space, coastal breezes and a fabulous open floor plan. The heart of the home is the impressive chef's kitchen featuring a large granite island, commercial-size side-by-side Sub-Zero refrigerator/freezer, Thermador double convection ovens, 6-burner gas cooktop with custom-paneled hood and Bosch dishwasher. The kitchen opens seamlessly to the dining area and spacious family room with gas fireplace-perfect for entertaining or simply enjoying the view. Vaulted ceilings, beautiful hardwood floors, a dramatic foyer and French doors leading to a private deck add to the bright, open feel. A rare floor plan offers BOTH first- and second-floor primary bedroom suites! Four bedrooms and 3 1/2 baths, with every bedroom enjoying direct access to a bathroom, provide wonderful flexibility for family, guests or multi-generational living. Additional highlights include first-floor laundry; central air; 2-zone gas heat; oversized 2-car garage; front porch; spacious, dry, partially finished basement; generator; basketball court; and lighted pea-stone driveway. Set on 2.2 secluded acres, yet close to beaches and everything that makes Old Saybrook and the Connecticut shoreline so special.This beautifully maintained home presents an exceptional opportunity to enjoy coastal living at its best

12 Drummers Trl, Old Saybrook
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