Old Saybrook Real Estate Search

Old Saybrook Properties for Sale

Our website features the best Old Saybrook real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

Old Saybrook is a coastal Connecticut shoreline town with a population around 11,000.  Old Saybrook has a long rich history which dates back to its founding in 1635.

One significant note is that Yale University was originally chartered in Old Saybrook in 1701 under the name the Collegiate School of Connecticut.  It was later renamed Yale University when it moved to New Haven in 1716.

Located in between New York City and Boston, Old Saybrook is easily commutable by train or I95.

Golf enthusiasts will love the Fenwick Golf Course which is a 9 hole course on the Connecticut shoreline.

Notable resident to the Fenwick borough is Katharine Hepburn who lived in Old Saybrook her entire life until 2003.

Old Saybrook’s cute downtown area is full of unique stores and high quality restaurants.  Fresh Salt directly on the water and Liv’s Oyster Bar are two town favorites.   The coast is adorned with sprawling beaches and beautiful luxury homes.

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Curious about what’s happening in the Old Saybrook real estate market? Sign up for a  Old Saybrook Real Estate Market Report to see what’s active, under contract, and sold!

Newest Old Saybrook Properties for Sale

$1,595,000
5 Beds 4 Baths 24020355 MLS
Welcome to 55 Otter Cove Dr where you are not just buying a home, you are buying a lifestyle! Located in a beautiful spot with views of the Connecticut River in the highly desirable and prestigious Otter Cove Estates of Old Saybrook. You will enjoy taking nice walks in this quiet community with CT River access a few steps away. Enjoy the spacious backyard situated on a 2.4 acre lot. Relax in the in-ground heated pool/spa and watch the Osprey circling high above. This inviting home has been thoughtfully re-designed for entertaining and boasts a much desired spacious open floor plan, Brazilian Teak hardwood flooring, custom kitchen with commercial grade appliances and Butler's pantry. The attention to detail though out the entire home makes it a pleasure to view. This property is completely out of the flood zone yet centrally located. Priced to sell quickly. The District of Otter Cove, a peaceful and serene area of lovely homes located on over 200 acres along the Connecticut River, enjoys an abundance of nature from the native plantings throughout, winding country lanes, spring-fed ponds, walking trails around Turtle Creek Preserve, the association beach on the Connecticut River and a variety of wildlife and birds including Osprey and Eagles. Minutes from both Essex and Old Saybrook downtowns. Convenient to get to RT 9 and I-95 for quick access to Boston and NYC. Enjoy all the wonderful restaurants, beaches, art galleries, and shopping in the area.

55 Otter Cove Drive, Old Saybrook

$1,595,000
5 Beds 4 Baths 24019051 MLS
Panoramic views of South Cove, Lynde Point Light and Long Island Sound abound in this exceptional Saybrook Point home. Designed and rebuilt in 2006 to capture magnificent views, find rooms bathed in light with elevated ceilings, custom millwork, and gleaming hardwoods. A balance of style and function, open concept living begins with the kitchen, living and dining areas with a wall of glass embracing cove views and all spaces anchored by a massive bluestone fireplace. A well-appointed kitchen features a granite center island with seating for five, gas cooking and large pantry with fieldstone floors echoing the fireplace. An office and laundry room are found on the east end along with one of two primary bedrooms. Created to accommodate extended family, the main level primary has an ensuite bath and walk-in closet. Heading upstairs, the second primary bedroom features a stunning balcony overlooking the cove, two walk-ins and a tile/glass bath with heated floor. Three spacious bedrooms enjoy a landing multi-purpose space. Spectacular outdoor living space includes an Ipe deck, stone patio, firepit and lawn framed by perennial and herb gardens, a new lawn, Cor-Ten edged stone drive and finally, a hedge of espalier apple. Perfectly located walking distance to the Connecticut River and Sound, marinas, Fenwick Golf, town beaches, The Kate and Main Street restaurants and shops. A short hop from Saybrook Station, 2 hours from NY and Boston. Truly exceptional.

32 Willard Avenue, Old Saybrook

$850,000
4 Beds 4 Baths 24016558 MLS
Tremendous location!! This nicely appointed craftsman ranch located high above the CT River with stunning upper level & seasonal main level views of the CT River Basin offers the amenities that can make all your dreams come true! As you pull-up the driveway to the 2 car garage you know that something special is about to unveil itself. The blooming trees & plantings abound as you approach the home that boasts surroundings that take your breath away. Large open back yard, wrap around deck with awnings accessed from both the kitchen & living room, spot-on landscaping & the feeling that you're now in an oasis trapped in time! The home is mostly single floor living that features an eat-in kitchen with granite counters & slider to the deck, separate dining room, fabulous living room with vaulted ceilings & sliders reaching the deck on both sides of the gas fireplace, three bedrooms including the original primary suite with walk-in closet & full bath, main foyer with open access to the lower level & main level sleeping quarter. The upper level was tastefully added in 2014 & features the 2nd & true primary suite with sitting room, dual walk-in closets, full bath & the stunning river views. The lower level is mostly unfinished & offers 2 sliders that walk-out to the expansive yard & storage. Other features include the Buderus hydro air HVAC system, full home Generac 18kw generator, central vac, work bench, storage shed & much, much more. Come see where dreams will be made!

5 Watch Hill Road, Old Saybrook

$2,000,000
3 Beds 3 Baths 24010523 MLS
Welcome to your custom-built eco-friendly dream home nestled within the exclusive Chalker Beach Association, offering unparalleled vistas of the majestic Long Island Sound. Step into your 2000sqft. sanctuary, meticulously crafted to harmonize with its natural surroundings and cater to your every comfort. This enchanting abode boasts three spacious bedrooms and three full bathrooms, ensuring ample space for relaxation and rejuvenation. Conveniently located beneath your home lies private parking, ensuring effortless access and convenience for you and your guests. The first floor invites you into a serene retreat, featuring a lavishly appointed bedroom and bathroom, seamlessly integrated with an open-concept kitchen. Adorned with stainless steel appliances and an induction stovetop, the kitchen is a culinary haven where you can unleash your culinary creativity. Gather around the dining table, capable of hosting a summer soiree for ten, while you soak in the tranquil water views from the adjacent great room. Ascending to the second floor, you'll discover two additional bedrooms, and two luxurious full bathrooms. The crowning jewel of this level is yet another breathtaking great room, offering panoramic vistas that inspire the creation of cherished memories for years to come. Radiant in-floor heating throughout the home ensures warmth and comfort even during the coldest New England winters, enveloping you in a cozy embrace year-round.

11 Chandler Street, Old Saybrook

$1,100,000
5 Baths 24006903 MLS
The landmark James Pharmacy building located on vibrant Main Street is fully occupied, operating as the James Pharmacy Bed & Breakfast and separately rented main level bistro. Anna James, daughter of a slave and the first African American female pharmacist owned, operated and resided at the iconic pharmacy for decades. Her niece, noted novelist Anna Petry, was born here and assisted Miss James. The main floor restaurant retains the historic pharmacy built-ins and soda fountain. Arched glass windows offer Main Street views. Three well-appointed, upscale B&B guest rooms have fully renovated baths and gas fireplaces. Innkeeper quarters are on the main level. Extensive updates and renovations were completed, bringing it to current standards while preserving its beauty and historic architecture. A full basement houses mechanicals, exceptional storage and restaurant clean storage. Old Saybrook is a popular weekend destination. A short stroll on sidewalk-lined streets leads to restaurants, shops, The Kate cultural arts center and Saybrook Station just 2 hours from NY/Boston. Find exceptional beaches, boating, Fenwick or Fox Hopyard Golf a short drive. A vibrant Chamber of Commerce works tirelessly ensuring Old Saybrook businesses have the support they need with Main Street events throughout the year. Limited area lodging ensures the James Pharmacy Bed & Breakfast and restaurant are an option with provenance year-round.

323 Main Street, Old Saybrook

$799,000
3 Beds 5 Baths 24009584 MLS
Elegant Custom-built brick colonial, situated on a cul de sac in a beautiful shoreline community. This pristine home is both an entertainer's and a gardener's dream! The recently updated main floor now offers an open floor plan and fresh paint. The foyer leads to a front-to-back living/family room with recessed lighting, hardwood floors, sleek custom fireplace and sliders to a large deck. The updated kitchen opens into the formal dining room. This level rounds out with a powder room and mudroom that accesses the attached 2-car garage. On the second floor, the primary suite features a tray ceiling, full bath with jet tub/separate shower, and a walk-in closet. The second primary suite, with full bath, has a balcony overlooking the backyard. Additionally on this level are a third bedroom, an office/4th bedroom and the third full bath. The lower level is well-appointed for entertaining. Currently used as a game lounge, this area has a built-in granite bar with sink, cooktop, and small refrigerator. Tons of storage and a full bathroom create potential for an inlaw suite. Walk out to a covered patio, hot tub and sprawling yard with beautiful mature plantings and a large fenced garden area. A double detached garage with second-floor loft, located at the rear of the property, is perfect for car and toy collectors and offers even more storage. Area for RV or boat storage too. Conveniently located two hours from New York/Boston, easy access to Amtrak/highways. The perfect retreat!

3 Christy Heights, Old Saybrook

$2,975,000
4 Beds 3 Baths 24003230 MLS
Direct beachfront property offering roughly 130 feet of unobstructed Long Island Sound views! Welcome to 29 West Shore Drive- a breathtaking westerly facing waterfront residence that promises magnificent sunsets, gentle seaside breezes and the picturesque lifestyle you've been dreaming of. For the first time in over 30 years this exquisite property is now available for sale, offering a unique opportunity to own a piece of paradise. Featuring 4 well-appointed bedrooms and 3 full bathrooms, this home is designed to accommodate and delight. Furthermore, you'll find a spacious living space with a stately stone fireplace that combines comfort with elegance, making it the perfect backdrop for creating lasting memories with loved ones. Through the living room French doors, enter a lovely sitting area with 180-degree views of ocean. The uniquely large, flat yard is perfect for gatherings or simply enjoying the peaceful ambiance of seaside living. This home is part of Cornfield Point Association - sandy beach, club house, basketball & tennis court & boat ramp. Easy access via I-95 and the train. Two hours from NY or Boston. Close to all amenities - restaurants, cafes, shopping, marinas, The Kate Theater & Fenwick Golf Course. Whether you're looking for a year-round home or a seasonal getaway, 29 West Shore Drive provides a rare blend of tranquility, beauty, and convenience in one of Old Saybrook's most sought-after locations. Don't miss the chance to make this dream home yours.

29 West Shore Drive, Old Saybrook

$1,995,000
5 Beds 5 Baths 24005740 MLS
New high-end construction now underway! An exquisite 4,300 +/- SF five bedroom, four and one-half bath coastal-inspired New England style home sited on a private, gated-entry 1.36 acre lot. Beautiful CT River Valley views. A first floor primary suite is nestled in its own wing. It includes a large walk-in closet, luxurious primary bath with spacious shower, freestanding soaking tub and abundant light through plentiful Andersen windows. A multiple-use first floor room with full bath can serve as office/bedroom/nursery/fitness area. The open concept chef's kitchen adjacent to the great room & dining room will feature a wine chiller, Wolf, Subzero and other fine appliances, a pot-filler, walk-in pantry and prep sink. First floor laundry room w/utility shower, plus second level laundry. First floor rooms have 9' ceilings. Three bedrooms, sitting area and two full baths upstairs. Above the three-bay attached garage is 800SF roughed-in for a full bath, ready for an in-law suite or other use. 9' height basement offers endless storage and options to be finished, complete with wine cellar. A showcase for transitional Luxe finishes and custom millwork throughout! James Hardie siding, custom entry & garage doors, screened porch, terrace w/fireplace. Room for optional pool. Old Saybrook fine dining, shops and theatre nearby. Less than a mile from marinas w/quick CT River access to Long Island Sound. Easy access to Routes 9, I-95 and Saybrook Junction train station. Builder ready to meet!

9 Overlook Drive, Old Saybrook

$949,000
1 Baths 24004763 MLS
INVESTMENT OPPORTUNITY - CORNFIELD POINT BEACH ASSOCIATION! This property presents a rare opportunity to own a versatile space that combines commercial and residential appeal. Whether you're seeking a lucrative investment, envisioning your own Airbnb, or own beach escape, this property offers endless possibilities. Situated in the sought-after Cornfield Point Beach Association, this property is at the entry of this very desirable beach community with many residents and guests driving by daily! The property boasts a flexible layout, featuring a spacious storefront ideal for retail, caf?, breakfast/lunch destination or ice cream! Additionally, there's a separate residential unit upstairs with 4 bedrooms, oversized deck, plenty of parking, full bath providing a rental opportunities. Maximize your investment with dual income streams. Whether you choose to lease out the storefront, rent the residential unit, or utilize both spaces for personal and commercial purposes, this property promises lucrative returns and financial flexibility. There is also the option of converting the storefront into 1-2 apartments. Walk or bike to Cornfield Point Beach/two town beaches, Main Street's shops, restaurants are a short drive/bike ride away, as are the Kate Cultural Arts Center, Fenwick Golf Course and Saybrook Point. Just a few hours from NYC or Boston, your private shoreline retreat is calling you. No flood insurance required.

3 Town Beach Road, Old Saybrook

$949,000
3 Beds 1 Baths 24004520 MLS
INVESTMENT OPPORTUNITY - CORNFIELD POINT BEACH ASSOCIATION! This property presents a rare opportunity to own a versatile space that combines commercial and residential appeal. Whether you're seeking a lucrative investment, envisioning your own Airbnb, or own beach escape, this property offers endless possibilities. Situated in the sought-after Cornfield Point Beach Association, this property is at the entry of this very desirable beach community with many residents and guests driving by daily! The property boasts a flexible layout, featuring a spacious storefront ideal for retail, caf?, breakfast/lunch destination or ice cream! Additionally, there's a separate residential unit upstairs with 4 bedrooms, oversized deck, plenty of parking, full bath providing a rental opportunities. Maximize your investment with dual income streams. Whether you choose to lease out the storefront, rent the residential unit, or utilize both spaces for personal and commercial purposes, this property promises lucrative returns and financial flexibility. There is also the option of converting the storefront into 1-2 apartments. Walk or bike to Cornfield Point Beach/two town beaches, Main Street's shops, restaurants are a short drive/bike ride away, as are the Kate Cultural Arts Center, Fenwick Golf Course and Saybrook Point. Just a few hours from NYC or Boston, your private shoreline retreat is calling you. No flood insurance required.

3 Town Beach Road, Old Saybrook

$4,150,000
4 Beds 6 Baths 24003657 MLS
Views abound! This beautiful waterfront home sits on 3 ? acres with 263ft of waterfront on the Connecticut River with a dock. This white brick and stone architecturally designed contemporary offers the ultimate in luxury with an open floor plan that flows seamlessly. The formal living room with a floor to ceiling bay window brings in light and views, and a beautifully carved white marble fireplace completes the room. A bright spacious open kitchen and breakfast room has skylights and a Palladium window. A large island with high end appliances makes this kitchen a chef’s delight! The family room with fireplace is off the kitchen and the sunroom too, with a dramatic high hexagonal ceiling. The first floor primary suite has a bay window overlooking the river and has five closets. The white marble bath has radiant heated floors, beautifully carved twin basins and a Jacuzzi and walk-in shower. A guest bedroom and Library completes the first floor. Most rooms have moldings, 9’ ceilings and/or tray ceilings and take advantage of the fabulous views. Stairs with a brass balustrade lead to the second floor two ensuite bedrooms one with a fireplace, a walk-in closet. A path from the house leads past flower gardens and over the expansive manicured lawn to the dockside stone patio, an ideal area for entertaining and to enjoy the stunning 180 degree river views. A two car garage completes this impeccably maintained, beautiful and unique property.

9 River Edge Road, Old Saybrook

$989,900
2 Beds 2 Baths 170623827 MLS
Nestled in the prestigious Cornfield Point Beach Association neighborhood, this upgraded ranch offers one-level living at its finest with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, central air, this home provides comfort and style. A spacious open plan living room welcomes you home with a wall of windows that flood the space with light and air; durable wood-look plank flooring offers easy maintenance. With vaulted ceilings, gas log fireplace, and ceramic tile flooring, your family room offers a cozy, inviting atmosphere. An immaculate updated kitchen with cherry cabinetry, breakfast bar island, stainless appliances, and granite counters is perfect for hosting. Spacious and light-filled, bedrooms feature updated carpeting and ample storage. A large driveway and detached garage provide plenty of off-street parking, while mature privacy hedging and greenspace creates an ideal space to relax with friends and family. HOA fees include trash, playground, tennis court & snow removal on the main road! Experience the incomparable quality of life Old Saybrook has to offer: blocks from the ocean, enjoy magnificent sunsets, local eateries, and beautiful nature preserves. With easy access to the train station for a quick commute into NYC, this home is perfect for year-round living, or seasonal enjoyment. Don't miss your opportunity to own this superlative one-level property; schedule your showing today!

24 Seabreeze Road, Old Saybrook

$975,000
3 Beds 3 Baths 170614449 MLS
Charming Colonial with something for everyone. Serene location on private street but only a short distance to the center of town. Beautiful living room with hardwood floors, raised panels and coffered ceiling along with built in bookcases. Large formal dining room with bay window offering an abundance of natural sunlight. The fully applianced country kitchen has a pantry and fireplace, recessed lighting and access to a glass sunroom with tile floor. Access to the deck and rear yard enhance the desirability of this room. Perfect room to sit and just relax or locate your piano here and make it a stunning music room. Upstairs you will find 3 spacious bedrooms and 2 full bathrooms. Primary bedroom includes a full bath with tub, two walk in closets and an atrium door to access the second sunroom with views of South Cove. New carpet in the primary bedroom, both walk in closets and the sunroom make this enclave a warm and cozy area to enjoy a good book or private office. Perfect size deck on the rear of the house with quick and easy access to the inground pool on those warm summer nights. Full basement, Oil forced hot air heat and Central Air. With the proximity to the town center you will be able to catch a show at "The Kate", hit the gym or use the pickleball courts for a quick game or just meander along visiting all of the great shops and restaurants on Main St. This house offers the complete package. Don't let this opportunity pass you by.

2 Trails End, Old Saybrook

$3,495,000
4 Beds 3 Baths 170575167 MLS
This traditional Fenwick cedar shingle style home has spectacular water views of the Connecticut River and South Cove. It also enjoys Fenwick’s unique lifestyle: beach, tennis courts, Yacht Club and famed golf course. The 2,634 home built in 2006 with the highest craftsmanship and state-of-the-art materials has wideboard floors throughout. The great room with a coffered ceiling has a wall of windows above the long banquette, a large beach stone fireplace and built-in cabinets. French doors on the main level open to a full width porch, which overlook the long water views and beautiful professionally landscaped gardens. The open kitchen is flooded with sunlight and is a chef’s delight with all top of the line appliances. Rich mahogany cabinetry and marble counters and sit down island are custom made. The first floor 15x15 master suite has built-ins, and has access to the porch. A guest room/office off the kitchen has a beadboard ceiling, shiplap walls, and state-of-the-art Murphy bed built into custom cabinetry. Mudroom side entrance with outdoor shower, includes extra built-in cabinets, farm sink and washer/dryer. Two guest rooms on the second level, one with built-in beds have access to the balcony with views of the hydrangea border gardens and water. This beautiful dream home sits on a private .46 acre parcel and has full mechanicals including a full house generator. Located half way between New York and Boston and is only minutes to all major transportation.

102b Sequassen Avenue, Old Saybrook

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