Old Saybrook Real Estate

Welcome to Old Saybrook, Connecticut—a charming coastal town where history meets natural beauty. Nestled in Middlesex County, Old Saybrook is not just a place to live; it's a lifestyle steeped in rich maritime heritage and vibrant community spirit. With its picturesque views of the Long Island Sound and the Connecticut River, this town offers a serene backdrop for both relaxation and adventure.

Old Saybrook is renowned for its stunning beaches, including the popular Harvey's Beach, where families gather for sun-soaked days and breathtaking sunsets. The town’s historic district is a treasure trove of colonial architecture, featuring beautifully preserved homes and landmarks that tell the story of its founding in 1635. Stroll through the quaint streets lined with boutique shops, art galleries, and delightful eateries, each offering a taste of local flavor.

For those who appreciate the arts, Old Saybrook is home to the renowned Katharine Hepburn Cultural Arts Center, which hosts a variety of performances and events throughout the year. The town also boasts numerous parks and recreational areas, perfect for hiking, biking, and enjoying the great outdoors.

Education is a priority in Old Saybrook, with highly-rated schools that foster a nurturing environment for students. Whether you're looking for a peaceful retreat or a vibrant community to call home, Old Saybrook offers a unique blend of tranquility and charm. Discover your place in this lovely coastal gem, where every day feels like a vacation!

Newest Listings in Old Saybrook

$839,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$1,200,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$900,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 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

$625,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 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

$2,495,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$679,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$1,190,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$995,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$140,000

ACTIVE Status ⋅ 24206910 MLS

Tina Perma Beauty Spa is a turnkey, fully equipped beauty studio in the heart of Old Saybrook's Main Street corridor in one of the most affluent shoreline markets in the Northeast. Established in 2020, the studio has built a loyal repeat clientele across permanent makeup, laser treatments, lash and brow services, waxing, and full nail care. What makes this offering unusual is the combination of three things a buyer rarely finds together: demonstrated growth, an exceptionally low fixed cost base, and clear untapped pricing capacity. Revenue climbed 26% in 2025 while occupancy cost held at roughly $800 per month - under 9% of gross revenue. The result is a discretionary earnings margin near 50% on a business that has never carried a marketing budget above $2,300 a year. The studio conveys fully equipped, including two commercial laser platforms, an established website and social presence, and a client database with booking system. A qualified buyer steps into an operating business with revenue on day one.

15 N Main St, Old Saybrook

$659,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24208801 MLS

Tucked away on a beautiful, wooded 1.5-acre lot, this home offers a rare blend of absolute privacy and everyday convenience. Step inside to a freshly painted, 2,606sqft 3 bed and 3 bath open-concept floor plan designed for seamless modern living and effortless entertaining. The heart of the home is anchored by a large kitchen featuring granite countertops, an island with high-top seating, ample cabinet space, and a functional layout that flows beautifully into the main living space. This main living space features a dramatic living room with a wall of windows that frame peaceful nature views and a soaring cathedral ceiling that maximize the sense of space and light. A dedicated home office, or potentially a first floor bedroom, a distinct step-down dining room, and a gorgeous full bathroom complete the first floor. Three generous bedrooms and two more full baths upstairs provide plenty of room for family or guests. The finished walkout basement allows for seamless outdoor access, making it a perfect rec room, gym, or media center. Outside, the expansive deck serves as the ideal backdrop for al-fresco dining, summer barbecues, or quiet mornings enjoying your peaceful, private outdoor space. Situated just minutes from Old Saybrook's vibrant town center and train station, this home provides a quiet escape with upscale dining, boutique shopping, beautiful shoreline beaches and a 1,000 acre nature preserve just a short distance away.

5 Connally Dr, Old Saybrook

$485,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24208270 MLS

This warm and inviting Cape offers the perfect blend of comfort, space, and convenience in a highly desirable Old Saybrook location. Just one mile from Main Street's charming shops, restaurants, and local attractions, this home features an open-concept main level highlighted by vaulted ceilings in the living room that seamlessly flows into the kitchen and dining area, creating an ideal space for everyday living and entertaining. Beautiful hardwood floors extend throughout the main living areas, while two first-floor bedrooms provide flexible living options. Upstairs, you'll find two additional bedrooms offering plenty of room for family, guests, or a home office. The partially finished basement adds valuable bonus space for recreation, fitness, or storage. Energy-conscious buyers will appreciate the solar panels, helping to offset utility costs. Conveniently located with easy access to Routes 9 and I-95, this home is perfect for commuters while still enjoying all the coastal charm and amenities that make Old Saybrook such a special place to call home.

1 Briarcliffe Trl, Old Saybrook

$935,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24207853 MLS

Step into this farmhouse with a bright, open and inviting floor plan. A welcoming grand foyer sets the tone, leading into sun-filled living spaces accented by hardwood floors, skylights and abundant windows throughout. The stunning wraparound deck is a true focal point of the home, offering the perfect setting for entertaining, relaxing or simply enjoying the peaceful surroundings. The main level features a spacious first-floor primary suite with a walk-in closet, laundry and a renovated bathroom. Upstairs, a loft overlooks the living space and is complemented by generously sized bedrooms and beautifully updated bathroom with heated floor. The full walkout basement provides excellent storage and additional possibilities.This home offers convenient access to the restaurants, shops, beaches, highways and train station. Enjoy all that Old Saybrook has to offer while coming home to a property that feels warm, distinctive and made for both entertaining and relaxing. Deferred maintenance needed. Professional photos coming.

6 Overlook Dr, Old Saybrook

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Old Saybrook Real Estate

Newest Listings in Old Saybrook

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