Homes with Pools for Sale in Old Saybrook, CT

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OPEN SAT, 12PM TO 2PM

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
This special home is perched high and dry on a sunny lot overlooking the great saltmarsh towards Long Island Sound. The views from this property must be seen to be appreciated and no flood insurance is required. Inside a warm, comfortable and open floorplan awaits the next owner with a private, association beach just a short walk, bike or golf cart ride away. Perfect for you your around home or a summer destination with family and friends. Professional pictures coming soon!

$750,000

2 beds2.5 baths2,132 sq ft

41 Briarwood Dr, Old Saybrook, CT 06475

0.51 acre lot • Built 1960

OPEN SAT, 12PM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Direct waterfront property on a private lot at 33 Briarwood Drive with expansive marsh and tidal channel views. This well maintained three bedroom two bath home features hardwood floors throughout and an open spacious interior layout. The bright studio space positioned well for a future glass enclosed sunroom offers flexible room for work hobbies or quiet relaxation. The setting provides a strong connection to the coastal environment while remaining practical for everyday living. No flood insurance is required per current information. This shoreline location places you close to highly used Old Saybrook amenities including Harveys Beach, Town Beach, Saybrook Point coastal preserves and multi

$685,000

3 beds1.5 baths2,272 sq ft

33 Briarwood Dr, Old Saybrook, CT 06475

0.51 acre lot • Built 1959 • Listed 20 days

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Discover a truly enchanting antique home nestled in the heart of Old Saybrook's quaint, historic charm. This beautiful 4/5 bedroom residence overflows with character and period details, offering a rare opportunity to own a piece of local history. Adding to its significant appeal is a separate guest suite, providing an excellent private space for guests or extended family. Experience small-town New England living at its finest, combining timeless elegance with modern flexibility. Old Saybrook, Connecticut is a quaint and picturesque coastal town where the Connecticut River meets Long Island Sound, offering classic New England charm and a relaxed shoreline lifestyle. Visitors and residents en

$849,000

5 beds3 baths2,898 sq ft

26 College St, Old Saybrook, CT 06475

Long island sound • Legal guest suite • Historic charm

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Surrounded by natural beauty and overlooking an ever-changing marsh, this inviting coastal retreat offers rare privacy, scenic views, and coveted deeded beach rights to Cornfield Point Beach, just a stroll away. Set on 1.44 acres and approached by a charming private bridge, the property feels peacefully removed while remaining moments from the heart of Old Saybrook. The picturesque grounds framed by flowering trees, and perennial gardens, create a serene backdrop for this classic colonial. Inside, the residence offers three bedrooms and three bathrooms, all recently renovated. Hardwood floors flow throughout, while a front-to-back living room with a fireplace provides a warm and welcoming s

$999,900

3 beds2.5 baths1,632 sq ft

1 Beamon Meadow Pl, Old Saybrook, CT 06475

Beach rights • Private bridge • Picturesque grounds

OPEN SAT, 1:30PM TO 2:30PM

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Downtown Old Saybrook Home | First-Floor Primary Suite | Walk to Town & Beach. This classic New England-style home nestled on a quiet dead-end street just steps from downtown Old Saybrook. Enjoy sidewalks leading to shops, restaurants, library, beaches, parks, and schools-everything you love is within easy reach. Set on a cleared half-acre lot, this property features professional landscaping with ever-blooming perennials. Inside, the spacious living room with a cozy fireplace and large open eat-in kitchen offer endless potential to make the space your own. The first-floor primary suite adds comfort and convenience, and the three-season screened porch is perfect for relaxing or enterta

$605,000

4 beds2 baths1,760 sq ft

18 Quarry St, Old Saybrook, CT 06475

0.41 acre lot • Garage • Built 1920

Property at 23 Clinton Ave, Old Saybrook, CT 06475, 3 beds, 2 baths

$949,900

3 beds2 baths1,510 sq ft

23 Clinton Ave, Old Saybrook, CT 06475

Property at 33 Fenwood Rd, Old Saybrook, CT 06475, 2 beds, 2 baths

$799,000

2 beds2 baths2,042 sq ft

33 Fenwood Rd, Old Saybrook, CT 06475

Property at 254 Hidden Cove Rd #254, Old Saybrook, CT 06475, 2 beds, 2.5 baths

$574,900

2 beds2.5 baths1,557 sq ft

254 Hidden Cove Rd #254, Old Saybrook, CT 06475

Property at 100 Dudley Ave Unit H43, Old Saybrook, CT 06475, 2 beds, 2.5 baths

$639,000

2 beds2.5 baths1,920 sq ft

100 Dudley Ave Unit H43, Old Saybrook, CT 06475

Property at 372 Maple Ave, Old Saybrook, CT 06475, 3 beds, 3 baths

$2,795,000

3 beds3 baths3,389 sq ft

372 Maple Ave, Old Saybrook, CT 06475

Property at 5 Sunrise Ave, Old Saybrook, CT 06475, 3 beds, 1 bath

$459,999

3 beds1 bath1,064 sq ft

5 Sunrise Ave, Old Saybrook, CT 06475

Property at Town Beach Rd, Old Saybrook, CT 06475, 5 beds, 2.5 baths

$985,000

5 beds2.5 baths3,472 sq ft

Town Beach Rd, Old Saybrook, CT 06475

Property at 24 Seabreeze Rd, Old Saybrook, CT 06475, 2 beds, 2 baths

$1,045,000

2 beds2 baths1,952 sq ft

24 Seabreeze Rd, Old Saybrook, CT 06475

Property at 175 N Cove Rd, Old Saybrook, CT 06475, 4 beds, 4.5 baths

$3,750,000

4 beds4.5 baths3,518 sq ft

175 N Cove Rd, Old Saybrook, CT 06475

Property at 125 Main St, Old Saybrook, CT 06475, 1 bed, 1.5 baths

$2,195,000

1 bed1.5 baths7,985 sq ft

125 Main St, Old Saybrook, CT 06475

Property at 118 Sandy Point Rd #118, Old Saybrook, CT 06475, 2 beds, 1.5 baths

$519,000

2 beds1.5 baths1,557 sq ft

118 Sandy Point Rd #118, Old Saybrook, CT 06475

Property at 10 Mulberry St, Old Saybrook, CT 06475

$575,000

— beds— baths— sq ft

10 Mulberry St, Old Saybrook, CT 06475

Property at 1333A Boston Post Rd, Old Saybrook, CT 06475

$995,000

— beds— baths— sq ft

1333A Boston Post Rd, Old Saybrook, CT 06475

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Nearby homes that match your criteria

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
A solidly built and sturdy Victorian with a lovely covered front porch in Essex Village is on the market for the first time in over 60 years. This welcoming home has high ceilings, beautiful molding and trim, the potential for a first-floor bedroom or home office with a private entrance, and peaceful seasonal water views of the Connecticut River and Middle Cove. The second floor has four generously sized bedrooms and two full bathrooms. The walk out level has a space that with a vision and a bit of TLC is a dreamy private space looking out to the low maintenance back yard. Saunter to everything Essex Village offers, galleries, boutiques, marinas, restaurants, museums, the renowned Griswold

$1,150,000

4 beds2.5 baths2,400 sq ft

35 Prospect St, Essex, CT 06426

0.38 acre lot • 4 parking spots • Built 1900

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Discover the enchantment of this historic Old Lyme Village landmark, originally established in 1897 as the former James Bugbee Store, and thoughtfully preserved as an iconic presence in the community since 1987. Rich in heritage and brimming with opportunity, this distinctive property offers a rare blend of historic charm, architectural character, and versatile use for both residential and commercial purposes. Set on an expansive parcel within the Turtle Fields Association, the property enjoys shared dock access to the Lieutenant River, creating a coveted connection to Old Lyme's natural beauty and waterfront lifestyle. The grounds include three barns, a storage shed, and a generous yard, o

$1,395,000

3 beds2 baths3,113 sq ft

60 Lyme St, Old Lyme, CT 06371

Three barns • Generous yard • Expansive parcel

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Exquisitely updated & remodeled Essex home on the cusp of South Cove with easterly views. This fabulous home has been completely transformed into something very special! From the eat-in kitchen with breakfast bar & smart design to the living room & family room both with wood burning fireplaces & sleeping quarter, no detail has been overlooked. The outdoor space has been completely revived with lavish landscaping, stone work, walls & plantings as well as a dream entertainment & relaxation area featuring the new Gunite pool with large blue stone hardscape, tiered retaining walls, built-in pool bar & cabana above the pool. The reconstructed deck runs t

$1,850,000

4 beds2.5 baths2,676 sq ft

9 Essex Hills Dr, Essex, CT 06426

Built-in pool bar • Reconstructed deck • Pavered walkways

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Welcome to Oakridge Village! Located in the heart of the Ivoryton, this well maintained and recently updated townhouse is just what you have been looking for in the perfect shoreline home. Designed for the way we live today, a warm and welcoming entrance leads to the spacious open floor plan and beautifully blends interior spaces with the natural surroundings. The light-filled kitchen features handsome wood cabinets, stainless appliances, updated countertops and a new kitchen sink. .. a half bath with a stackable washer and dryer complete the main level. Upstairs you'll find a recently remodeled full bath and two well-appointed bedrooms, one featuring a convenient walk-in-closet. Ideal for

$289,000

2 beds1.5 baths828 sq ft

20 Comstock Ave Apt 4C, Ivoryton, CT 06442

Private deck • Light filled kitchen • Park like grounds

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Welcome to your dream home nestled on a serene 1.0 acre wooded lot, complete with a tranquil pond in the backyard - perfect for peaceful mornings and relaxing evenings. Home features Expansive kitchen ideal for entertaining and family gatherings, 4 spacious bedrooms including 2 luxurious primary suites, heated floor in 1st level primary bath, double-faced fireplace warming both the cozy living room and inviting family room. Includes two-car garage with ample storage and large front porch protected from the weather. Conveniently located just minutes off I-95 for easy commuting, yet tucked away in your own slice of private paradise. Home is perfect for families who love to entertain both indo

$699,900

4 beds3.5 baths3,308 sq ft

821 Essex Rd, Westbrook, CT 06498

Wooded lot • Expansive kitchen • Heated floor

ABOUT THIS HOME
Home with a Pool for sale in Old Saybrook, CT:
Welcome to your perfect coastal retreat! Nestled in Green Acres Park, 8 Cook Terrace offers the ideal blend of comfort, convenience, and shoreline charm. This bright and cozy modular home features 1 bedroom, 1 full bath, an inviting living area, and an efficient eat-in kitchen-perfect for simple, low-maintenance living. Enjoy in-unit laundry, propane heat, and a spacious corner lot that provides added privacy, a sunny deck, and room for outdoor relaxation or gardening. Lovingly maintained, this home sits just minutes from Westbrook's sandy beaches, marinas, and some of Connecticut's most popular shoreline restaurants and shops. Quick access to I-95 and Old Saybrook makes this an ideal year-

$76,900

1 bed1 bath440 sq ft

8 Cook Ter, Westbrook, CT 06498

Sunny deck • In-unit laundry • Spacious corner lot

Property at 24 Lyme St, Old Lyme, CT 06371, 1 bed, 3 baths

$1,200,000

1 bed3 baths3,384 sq ft

24 Lyme St, Old Lyme, CT 06371

Property at 8 Lieutenant River Ln, Old Lyme, CT 06371, 3 beds, 2.5 baths

$1,600,000

3 beds2.5 baths2,215 sq ft

8 Lieutenant River Ln, Old Lyme, CT 06371

Property at 41 Trolley Rd, Westbrook, CT 06498, 2 beds, 1 bath

$375,000

2 beds1 bath573 sq ft

41 Trolley Rd, Westbrook, CT 06498

Property at 45 Main St, Essex, CT 06442, 3 beds, 2.5 baths

$824,900

3 beds2.5 baths2,456 sq ft

45 Main St, Essex, CT 06442

Property at 3 Essex Sq, Essex, CT 06426, 1.5 baths

$795,000

— beds1.5 baths3,177 sq ft

3 Essex Sq, Essex, CT 06426

Property at 29 Salt Island Rd, Westbrook, CT 06498, 4 beds, 2 baths

$475,000

4 beds2 baths1,665 sq ft

29 Salt Island Rd, Westbrook, CT 06498

Property at 7 Katherine Rd, Old Lyme, CT 06371, 2 beds, 1 bath

$270,000

2 beds1 bath684 sq ft

7 Katherine Rd, Old Lyme, CT 06371

Property at 11 N Main St, Essex, CT 06426, 4 beds, 3 baths

$1,350,000

4 beds3 baths3,036 sq ft

11 N Main St, Essex, CT 06426

Property at 1 Lake Louise Dr, Westbrook, CT 06498, 5 beds, 5 baths

$999,999

5 beds5 baths5,028 sq ft

1 Lake Louise Dr, Westbrook, CT 06498

Property at 18 Benson Ln, Essex, CT 06426, 4 beds, 2.5 baths

$1,475,000

4 beds2.5 baths2,634 sq ft

18 Benson Ln, Essex, CT 06426

Property at 70 Sill Ln, Old Lyme, CT 06371, 4 beds, 4 baths

$1,765,000

4 beds4 baths5,160 sq ft

70 Sill Ln, Old Lyme, CT 06371

$725,000

— beds— baths— sq ft

4 Bank Ln, Essex, CT 06426

Property at 1 Huntley Rd, Old Lyme, CT 06371

$795,000

— beds— baths— sq ft

1 Huntley Rd, Old Lyme, CT 06371

Property at 130 Mares Hill Rd, Ivoryton, CT 06442

$300,000

— beds— baths— sq ft

130 Mares Hill Rd, Ivoryton, CT 06442

Homes with Pools for Sale in Old Saybrook

There are currently 18 homes with pools for sale in Old Saybrook at a median listing price of $895K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Old Saybrook stay on the market for 86 days and receive 1 offers. This map is refreshed with the newest listings in Old Saybrook every 15 minutes.

In the past month, 13 homes have been sold in Old Saybrook. In addition to houses in Old Saybrook, there were also 8 condos, 0 townhouses, and 1 multi-family unit for sale in Old Saybrook last month. Find your dream home in Old Saybrook using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Old Saybrook are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Old Saybrook. If you're looking to sell your home in the Old Saybrook area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Old Saybrook with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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