Old Saybrook School District, CT homes for sale & real estate

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50 Fenwood Dr, Old Saybrook, CT 06475

OPEN SAT, 11AM TO 4PM

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
First time this charming home is available for sale. Built, owned and cared for by the same family since 1954. Because it's an estate the house is being sold "as-is". There is a partially finished full basement, with a full bath, that could easily turn this into a 3 bedroom or whatever you choose. So many possibilities if you are up for a renovation, the good bones are there. The lot sits out of the flood zone and has the benefit of being on a corner, with expansive views of the neighborhood and the marsh across the street. This home is part of the "Fenwood Assoc. ," it's a short walk to the Assoc. beach with a view of 2 lighthouses. The Fenwick Golf course is just down

$643,000

2 beds2 baths1,408 sq ft

50 Fenwood Dr, Old Saybrook, CT 06475

0.25 acre lot • Garage • Car-dependent

1 Connally Dr, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
PROFESSIONAL PHOTOS WILL BE ADDED 12/13. Welcome to this charming cape-style home, perfectly situated less than a mile from Main Street. The land and home has only had one owner and has been well maintained. This property offers a unique opportunity to create your dream home with some personal touches. Featuring 3 bedrooms and 2 bathrooms, the first floor includes a formal living room and dining room with hardwood floors, a kitchen, a primary bedroom, a full bathroom, and a spacious family room. Upstairs, you'll find two additional bedrooms. The full walkout lower level includes a newer heating system and a laundry area. All appliances are included. Nestled on a quaint neighborhood street,

$399,900

3 beds2 baths1,748 sq ft

1 Connally Dr, Old Saybrook, CT 06475

1.8 acre lot • Car-dependent

125 Main St, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Great opportunity to own a mixed use property on Main Street in Old Saybrook. Established salon with long term lease on first floor. Second floor has one bedroom apartment which can easily add more bedrooms or use as office space. Third floor currently occupied by two businesses and can be converted into apartment if the need arises. Prime location near The Kate and all downtown businesses. Easy access to Rt I-95 and Rt 9. Additionally there is a large 25 car parking lot in the rear of the building that has potential for future development. Perfect chance to live downtown and have positive cash flow.

$2,495,000

1 bed1.5 baths7,985 sq ft

125 Main St, Old Saybrook, CT 06475

0.23 acre lot • Somewhat walkable

26 College St, Old Saybrook, CT 06475

OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Step into this Nantucket-style gem in the heart of historic Old Saybrook, Connecticut-a beautifully updated 3,600 sqft home offering endless charm and versatility. With 5 spacious bedrooms and 3 bathrooms, including a private in-law or au-pair suite, this home has room for everything-family, guests, or rental income potential. A brand-new 20'x20' garage, built by renowned local builder BWC Construction (@bwc_constructionllc), includes a 100amp subpanel, ideal for charging your electric vehicle and powering the included hot tub. Inside, cozy up to the warmth of a gas fireplace, and enjoy recent updates like a two-meter electrical service, chimney reflashing, and a new high-capacity hot water

$1,199,500

5 beds3 baths3,000 sq ft

26 College St, Old Saybrook, CT 06475

0.75 acre lot • 2 garage spots • Car-dependent

100 Dudley Ave Unit D19, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Welcome to Sheltered Cove, D19. Experience luxurious living in this stunning condominium boasting fabulous water views of the Connecticut River, North Cove and tidal wetlands. The open concept living and dining area is anchored by a custom designed fireplace creating a warm and inviting ambiance. Step out onto the patio from the living room and soak in the breathtaking vistas. The eat in kitchen features both style and functionality, perfect for casual dining. Retreat to the large master bedroom with an en-suite bath for ultimate comfort. A second well appointed bedroom and an additional bath complete this exceptional condominium. Additional features include a full basement perfect for stor

$759,000

2 beds2.5 baths1,565 sq ft

100 Dudley Ave Unit D19, Old Saybrook, CT 06475

$500 HOA • Garage • Pool

91 N Cove Rd, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
This exquisite design merges the historic charm of colonial New England with the elegance and comfort of modern living. The 2020 comprehensive restoration of this flagship historic landmark has been executed with precision, ensuring every detail and world-class design element is perfect. Upon entry, the harmonious blend of 18th-century allure with contemporary technology, oak flooring, Shiplap walls, a spacious open floor plan, high vaulted ceilings, heated floors and original beams aged 300 years, alongside panoramic waterfront views, is striking. The main level is devoted to the serene North Cove waterfront, boasting a glass-partitioned office, a grand room with a luxurious gourmet kitche

$6,995,000

6 beds7 baths5,592 sq ft

91 N Cove Rd, Old Saybrook, CT 06475

0.48 acre lot • 3 garage spots • Pool

6 Briarwood Dr, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Discover the perfect coastal retreat in this beautifully updated ranch, ideal for those seeking the charm of seaside living. With 3 bedrooms and 1.5 baths, this home has been meticulously maintained and brought to new condition, featuring a new roof, windows, updated mechanicals, and central air conditioning. Situated on a level half-acre lot, the property offers exciting potential for future additions, such as garages or even a pool, tailored to your lifestyle. Enjoy the convenience of walking to three picturesque beaches, with deeded beach rights to Cornfield Point Beach providing an exclusive touch. The backyard is a true gem-flat and expansive, perfect for gardening or outdoor activitie

$560,000

3 beds1.5 baths1,008 sq ft

6 Briarwood Dr, Old Saybrook, CT 06475

0.52 acre lot • Car-dependent

367 Main St #20, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Nestled in a peaceful cul-de-sac, this rare stand-alone condo provides the perfect blend of coastal charm and modern convenience in one of Old Saybrook's most desirable neighborhoods. Just steps from the library, downtown shops, restaurants, schools, and the water, you'll also enjoy the option to bike to the beach or stroll through the vibrant town center. Step inside to discover a bright and airy living space featuring vaulted ceilings and an open floor plan, designed for comfort and ease. The spacious living room is bathed in natural light, creating a welcoming ambiance for relaxing or entertaining. A private three season room invites you to unwind and take in the serene surroundings, wit

$649,900

2 beds2.5 baths1,388 sq ft

367 Main St #20, Old Saybrook, CT 06475

$372 HOA • Garage • Somewhat walkable

4 Beachman Ave, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
This is a rare opportunity to live by the water year round in the Saybrook Manor Cove Beach private beach community! The amazing location of Old Saybrook is situated between New York and Boston. You will be just a short walk from the private Cove Beach. Additionally, you are only minutes away from golfing, the train station, the Arts Center, the Cultural Center, and Downtown Main Street. This is a golf cart-friendly community that includes deeded beach rights to Cove Beach, making it perfect for year-round relaxation and recreation. The home features 4 bedrooms, 2.5 baths, and a 1-car garage. The primary bedroom has its own full bath and a private entrance from the garage, which can lead to

$710,000

4 beds2.5 baths1,846 sq ft

4 Beachman Ave, Old Saybrook, CT 06475

9,147 sq ft lot • $25 HOA • Garage

6 Parkman Pl, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Nestled in one of the most sought-after neighborhoods, this stunning residence offers unparalleled luxury and comfort designed for the discerning homeowner. As you enter, you are greeted by soaring ceilings and expansive windows that bathe each room in natural light, highlighting the meticulous attention to detail and high-end finishes throughout. The gourmet kitchen is a chef's dream, equipped with state-of-the-art appliances and elegant cabinetry, perfect for both intimate dinners and grand entertaining. The main level master suite is a private retreat with sitting room featuring a spacious walk-in closet and a spa-like bathroom with a soaking tub and a separate shower. Step outside to th

$1,095,000

4 beds2.5 baths3,301 sq ft

6 Parkman Pl, Old Saybrook, CT 06475

1.05 acre lot • 2 garage spots • Car-dependent

100 Sheffield St Unit A5, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Welcome to your beautiful water view oasis at "The Cove" in charming Old Saybrook. This 1470 sq ft Town House is truly located in a serene setting with magnificent views of North Cove right from your doorstep. Step inside and you will find a spacious living area filled with natural light. The entire interior of this home was freshley painted. The living room features a centrally appointed fireplace a great place to just sit and relax and admire the views. The chef-like kitchen, recently renovated, includes a upscale new back splash, state-of-the-art range hood, granite countertops, stainless steel appliances, breakfast bar, along and seamless view to the patio and beyond. The pri

$675,000

2 beds2.5 baths1,470 sq ft

100 Sheffield St Unit A5, Old Saybrook, CT 06475

$470 HOA • Garage • Somewhat walkable

18 1st Ave, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Panoramic Connecticut River and Tidal Marsh Views-A hidden gem tucked privately alongside the marsh where you will enjoy views of the sparkling waters of the river, wildlife, and the boats making their way on the river. This charming and bright home wins you over with sundrenched rooms and open floorplan. Perfect as year-round residence, weekend getaway, or use as an investment property. Walk to marinas and minutes to the sought-after town of Old Saybrook as well as the village of Essex. Take the train conveniently from NY or Boston and start living the desirable shoreline lifestyle.

$499,900

1 bed1.5 baths1,114 sq ft

18 1st Ave, Old Saybrook, CT 06475

1.1 acre lot • Car-dependent

9 Overlook Dr, Old Saybrook, CT 06475

NEW CONSTRUCTIONVIDEO TOUR

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Presenting a newly constructed high-end home just completed. This magnificent 4,300 sq. ft. coastal-inspired New England style residence boasts 5 bedrooms and 4.5 baths, nestled on a private, gated 1.36-acre lot. The secluded primary suite on the first floor features an expansive walk-in closet and an opulent bathroom with a sizable shower, standalone soaking tub, and plentiful natural light from Andersen windows. An additional flexible first-floor bedroom with an en suite bath can double as an office, nursery, or gym. The chef's kitchen, flowing into the great room and dining area, will host premium appliances such as a Bertazzoni range, Sub-Zero refrigerator, wine chiller, and more. It al

$1,995,000

5 beds4.5 baths4,300 sq ft

9 Overlook Dr, Old Saybrook, CT 06475

1.36 acre lot • 3 garage spots • Car-dependent

372 Maple Ave, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Welcome to your dream home! This stunning colonial with beautiful views of Long Island Sound comes fully furnished with stylish, high-quality pieces, making it the perfect turnkey beach property. The well-equipped kitchen has granite countertops, stainless steel appliances including double Viking Ovens, SubZero fridge, large Island with breakfast bar and access to the patio. The dining room has a built-in service station with granite countertop and is open to the living room. The living room is full of charm with a fireplace and built-in bookshelves. The bright sunroom has wainscoting and shiplap ceiling. The office also has built-in bookshelves and granite countertops. The primary bedroom

$3,100,000

3 beds3 baths4,789 sq ft

372 Maple Ave, Old Saybrook, CT 06475

0.31 acre lot • $250 HOA • 2 garage spots

11 Coulter St Unit 20, Old Saybrook, CT 06475

FOR SALE BY OWNER

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
What& apos; s special Gas fireplace Central air Bone dry basement Attached garage Wet bar Birds galore Spacious ensuite bathroom Want to live in the heart of downtown Old Saybrook? Walk to restaurants, banks. .. everywhere, from this pristine move-in condition condo in low key, well maintained association. All on one floor layout features central air, all new kitchen/bath appliances, fixtures, cabinets, granite countertops, washer/dryer, wet bar, attached garage. Skylit living room with gas fireplace opens out to deck, wetlands and birds galore! Main bedroom features walk-iner Em closet to spacious ensuite bathroom. This condo has a huge, high ceilinged, bone dry basement with tons of

$630,000

2 beds2 baths1,512 sq ft

11 Coulter St Unit 20, Old Saybrook, CT 06475

2 garage spots • Somewhat walkable

86 Chalker Beach Rd, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Do you need a year round Beach Home with a lot of room? Look no further! Welcome to 86 Chalker Beach Rd! Welcome to Beach Living! There is plenty of space for all, a rare find in beach communities and almost 2300 Sq Ft can accommodate! With four bedrooms and two full baths that is enough for family and friends. First floor master bedroom with double walk in closets is adjacent to the full bath. Head upstairs and you will be even more amazed with the size of this home as there are three additional bedrooms all equipped sufficient storage and a large full bath that is a dream to get ready in. And when it's time to cook for your inhabitants, the kitchen affords enough square footage to move ab

$995,000

4 beds2 baths2,249 sq ft

86 Chalker Beach Rd, Old Saybrook, CT 06475

0.23 acre lot • Garage • Car-dependent

30 Watrous Point Rd, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
This quietly elegant property is well-sited in Watrous Point. Well-planned space features extensive millwork and lofted ceilings and allows for complete first floor living and plenty of second floor space for family and guests. A stunning hardscape and barrel-vaulted entry greets you with a heated lower landing. Enter a soaring gallery flanked by the library built to house the most extensive collections. The hexagonal cherry kitchen commands an 8-burner Wolf range, two Gaggenau convection ovens with warming drawers and dual Subzeros. The large eat in area with a fieldstone fireplace will be the center point of your gatherings. There is a dream pantry. The adjacent great room with the second

$1,650,000

4 beds4 baths4,546 sq ft

30 Watrous Point Rd, Old Saybrook, CT 06475

3.1 acre lot • 3 garage spots • Pool

46 Soundview Ave, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Your dream home awaits! Stunning year round waterfront property in Old Saybrook. With the potential to add another bedroom Walk to Saybrook Point Inn and Marina, Main Street and "The Kate". Breathtaking views of South Cove and Saybrook Light House. Enjoy the natural wildlife including an osprey nest while sitting on your new deck with awning. The south cove is separated by the causeway so there are no motor boats coming in and out. Kayak, paddleboard, fish or go crabbing all from your front yard. Situated on a half acre, there is plenty of room to set up a tent for a formal affair or have a picnic with outdoor activities. Easy commute by train or car from NYC.

$849,900

1 bed1 bath920 sq ft

46 Soundview Ave, Old Saybrook, CT 06475

0.53 acre lot • Car-dependent

64 Otter Cove Dr Lot 2 PKG, Old Saybrook, CT 06475

NEW CONSTRUCTION

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
NEW CONSTRUCTION! Don't miss out on this rare opportunity to own a special 2.5-acre building lot to build your custom dream home in the revered District of Otter Cove in the coastal community of Old Saybrook. With potential distant seasonal views of the scenic CT River Valley and abutting preserved land, this unique opportunity offers an endless palette of ideas to create your private oasis. The lot has been surveyed, tested, and approved with endless possibilities such as pool, patio, detached garage, equine etc. The listing agent is a licensed professional engineer and can assist with any lot development or zoning related matters to maximize efficiency in making your dream become reality.

$1,700,000

4 beds2.5 baths2,500 sq ft

64 Otter Cove Dr Lot 2 PKG, Old Saybrook, CT 06475

2.49 acre lot • 2 garage spots • Car-dependent

1 Wildwood Rd, Old Saybrook, CT 06475

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Welcome to your dream home in the desirable beach community of Cornfield Point! This charming 3-bedroom, 2-bathroom residence features a perfect blend of modern convenience and coastal charm. Enjoy a spacious layout designed for seamless living and entertaining. Large windows throughout the home flood the space with sunlight, creating a warm and inviting atmosphere. The main level features a comfortable bedroom and a full bathroom, ideal for guests or as a primary bedroom. The upper level includes two additional bedrooms, a dedicated office space, and a remodeled bathroom, providing ample space for family and work-from-home needs. Beautiful hardwood flooring runs throughout the home, adding

$1,125,000

3 beds2 baths1,764 sq ft

1 Wildwood Rd, Old Saybrook, CT 06475

7,840 sq ft lot • $36 HOA • Car-dependent

55 Otter Cove Dr, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Welcome to 55 Otter Cove Dr, a charming New England residence that offers an unparalleled multi-generational living experience in the prestigious Otter Cove Estates. This exquisite home, located in a serene community with private beach access to the Connecticut River, is more than just a house-it's a lifestyle. Property Features: 5 Beds, 4 Baths, 4,792 SqFt on 2.4 Acres with Water Views of the CT River, private beach access, in-ground heated pool/spa, and full in-law/ au pair apartment. Step through the carved wood entry doors and admire the high-quality construction and attention to detail. The spacious open floor plan, features an expansive living room with a marble gas fireplace and cozy

$1,470,000

5 beds4 baths4,792 sq ft

55 Otter Cove Dr, Old Saybrook, CT 06475

2.4 acre lot • $42 HOA • 2 garage spots

973 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Old Saybrook, 32+ Acres FARM for sale! "Gentleman's Farm" with barns, farmhouse, outbuildings, pastures and beautiful treed acres with subdivision possibilities or an idyllic location for your private estate or compound. This is truly a rare opportunity to own over 32 acres in Old Saybrook. Caution! Animals on premises! Please do not go on property without an appointment. Thank you. Livestock not included in sale. PARCEL DETAILS: The parcel consist of tax map 62 Lot 35, 5.93 acres, a portion in forestry, zoned B-3 including a house, barn, shed & numerous outbuildings along with 26.41 acres from tax map 62, Lot 14, 15 & 16, All AA-1 Zone and in forestry. Being sold as-

$1,150,000

2 beds1 bath751 sq ft

973 Middlesex Tpke, Old Saybrook, CT 06475

32.34 acre lot • 2 garage spots • Car-dependent

711 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Vacant lot with great exposure for business application. B2 zone with survey map and soil tests available. Great location for multiple uses in a high traffic area.

$299,000

— beds— baths— sq ft

711 Middlesex Tpke, Old Saybrook, CT 06475

2.2 acre lot • Car-dependent

64 Otter Cove Dr, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
FULLY ENGINEERED & APPROVED BUILDING LOT! Don't miss out on this rare opportunity to own a 2.5-acre building lot in the prestigious Otter Cove Association in Old Saybrook. The lot offers potential views of the Connecticut River Valley and abuts preserved open space. Fully surveyed, tested, and approved, this lot is ready for your custom dream home. The listing agent, a licensed professional engineer, can help with any development or zoning needs. Create your private oasis with a swimming pool, outdoor area, equine, barn, or more. Make your dream home a reality in this beautiful coastal community minutes away from village centers and highways! This lot is also offered with a custom ho

$500,000

— beds— baths— sq ft

64 Otter Cove Dr, Old Saybrook, CT 06475

2.49 acre lot • Car-dependent

60 Ingham Hill Rd, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Picturesque waterfront 8.1 acre lot on the tranquil Oyster River in historic Old Saybrook has over 1400 ft of river frontage leading to Long Island Sound, allowing for all types of seaside recreation. This much loved pastural farmland has been privately owned for more than a century and has long been valued for its fertile soil and scenic vistas. Bald Eagles, ospreys and other rarely seen flora and fauna also make this extraordinary lot their home. The location is perfect. I-95 is easily accessible, and the lot is minutes away from Old Saybrook’s beautiful beaches and charming Main Street with its quaint shops and fine dining. The sky’s the limit with this lovely waterfront esca

$859,000

— beds— baths— sq ft

60 Ingham Hill Rd, Old Saybrook, CT 06475

8.11 acre lot • Car-dependent

220 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Builders and Developers Take Notice! Very large development opportunity. 124 acres of residential land. Located on Middlesex Turnpike right next to I95. Very convenient location minutes from downtown Old Saybrook and all the town beaches. The possibilities are endless.

$2,950,000

— beds— baths— sq ft

220 Middlesex Tpke, Old Saybrook, CT 06475

124.08 acre lot • Car-dependent

382 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Builders and Developers Take Notice! Development Opportunity. 17 Acre Residential building lot on Middlesex Turnpike in a very convenient location near I95. Right behind multiple available Commercial and Residential building lots.

$1,490,000

— beds— baths— sq ft

382 Middlesex Tpke, Old Saybrook, CT 06475

17 acre lot • Car-dependent

384 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Builders and Developers Take Notice! 1.65 Acre Commercial building lot on Middlesex Turnpike in a very convenient location. Right next to multiple available Commercial and Residential building lots.

$539,000

— beds— baths336 sq ft

384 Middlesex Tpke, Old Saybrook, CT 06475

1.65 acre lot • Car-dependent

350 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Builders and Developers Take Notice! 1.38 Acre Commercial building lot on Middlesex Turnpike in a very convenient location near I95.. Right next to multiple available Commercial and Residential building lots.

$849,000

— beds— baths— sq ft

350 Middlesex Tpke, Old Saybrook, CT 06475

1.38 acre lot • Car-dependent

396 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Builders and Developers Take Notice! 1 Acre Commercial building lot on Middlesex Turnpike in a very convenient location. Right next to multiple available Commercial and Residential building lots.

$439,000

— beds— baths— sq ft

396 Middlesex Tpke, Old Saybrook, CT 06475

1 acre lot • Car-dependent

410 Middlesex Tpke, Old Saybrook, CT 06475

ABOUT THIS HOME
Old Saybrook School District, CT Homes for Sale
Builders Take Notice! 2.65 Acre building lot on Middlesex Turnpike in very convenient location. Right next to multiple available Commercial building lots.

$125,000

— beds— baths— sq ft

410 Middlesex Tpke, Old Saybrook, CT 06475

2.65 acre lot • Car-dependent

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