Vintage homes for sale & real estate in Old Saybrook, CT

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ABOUT THIS HOME
Vintage Home 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, legal 1-bedroom guest suite, providing an excellent source of income or a 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 shoreli

$849,000

5 beds3 baths2,898 sq ft

26 College St, Old Saybrook, CT 06475

Long island sound • Legal guest suite • Historic charm

COMING SOON

ABOUT THIS HOME
Vintage Home 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 7 days

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
This home is being sold "AS IS". Right place at the right time! This home now wants a new owner. Renovations are needed but location, location, location. Water views with walking ability to Saybrook Point and Fenwick golf course. Ranch with 3 beds and 2 baths. This is an opportunity to enjoy Old Saybrook at its best. see virtual video ty

$799,900

3 beds2 baths1,432 sq ft

21 Fenwick St, Old Saybrook, CT 06475

8,276 sq ft lot • 2 garage spots • Built 1938

ABOUT THIS HOME
Vintage Home 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

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Fenwood Beach Association! This beautifully renovated home is ready for you to move right in to this newly updated home. The light-filled interior offers an open flow between the kitchen, dining, and living areas, perfect for relaxed coastal living. The primary suite features a gorgeous new full bath, while the finished lower level adds 700 sq ft of flexible space currently used as a family room and third bedroom. Step outside to a park-like backyard with a covered patio, creating a shaded, year-round retreat. Situated on a . 19-acre lot outside the flood zone. Free extras: 3 wall mounted tvs included, Prepaid oil per contract and oil in tank included, Service contract up to renewal date on

$799,000

2 beds2 baths2,042 sq ft

33 Fenwood Rd, Old Saybrook, CT 06475

Park like backyard • Covered patio • Open flow

Property at 20 Hill St, Old Saybrook, CT 06475, 2 beds, 2 baths

$749,900

2 beds2 baths1,432 sq ft

20 Hill St, 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 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 41 Watrous Point Rd, Old Saybrook, CT 06475, 6 beds, 4.5 baths

$4,250,000

6 beds4.5 baths5,536 sq ft

41 Watrous Point 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 23 Briarwood Dr, Old Saybrook, CT 06475, 3 beds, 2 baths

$895,000

3 beds2 baths2,000 sq ft

23 Briarwood Dr, Old Saybrook, CT 06475

Property at 14 Denmore Ln, Old Saybrook, CT 06475, 3 beds, 1 bath

$520,000

3 beds1 bath1,196 sq ft

14 Denmore Ln, Old Saybrook, CT 06475

Property at 96 Chalker Beach Rd, Old Saybrook, CT 06475, 3 beds, 1 bath

$649,900

3 beds1 bath870 sq ft

96 Chalker Beach Rd, Old Saybrook, CT 06475

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ABOUT THIS HOME
Vintage Home 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

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
* TENANT FREE * Two well-maintained historic buildings in the heart of the Old Lyme Historic District! 24 & 26 Lyme Street are being sold together, offering a unique chance to invest in a high-visibility location within this charming New England village. * 24 Lyme Street (built in 1800) features 1,824 sq. ft. of retail and office space, ideal for business use or potential redevelopment. * 26 Lyme Street (built in 1750) offers 1,560 sq. ft. , including a beautifully designed one-bedroom apartment on the second floor with a touch of Manhattan elegance. This property also boasts a working chimney, an updated foundation (1988), new beams, and stunning oak floors-a seamless blend of hi

$1,200,000

1 bed3 baths3,384 sq ft

24 Lyme St, Old Lyme, CT 06371

Working chimney • New beams • Updated foundation

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Charming Essex Village Gem! Located in the heart of Essex Village, this beautifully updated antique home offers the perfect blend of historic charm and modern comfort-all just a short stroll to the water, Essex Harbor, and the village's delightful shops and restaurants. Inside, you'll find 3 bedrooms and 2.5 baths, with stunning details throughout. The spacious, remodeled kitchen is a chef's dream, featuring custom cabinetry, a large center island, Wolf appliances, and a Sub-Zero refrigerator. The inviting living, dining, and family rooms-complete with a cozy fireplace-and a bright sunroom create wonderful spaces for relaxing or entertaining. The primary suite impresses with a cathedral cei

$1,225,000

3 beds2.5 baths2,402 sq ft

9 Pratt St, Essex, CT 06426

Updated antique home • Custom cabinetry • Large center island

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Welcome to 8 Lieutenant River Lane, an exquisitely renovated colonial in the heart of Old Lyme Village, where timeless charm meets contemporary luxury. This meticulously updated home showcases a stunning high-end kitchen designed for both daily living and gracious entertaining. The cozy living room, anchored by a wood-burning fireplace, creates an inviting atmosphere for intimate gatherings or quiet evenings at home. Adjacent, the warm and inviting library features custom built-in bookshelves with elegant under-lighting, flowing effortlessly through French doors to the beautifully crafted stone patio, a perfect place for outdoor dining and relaxation amid the lush, professionally maintained

$1,600,000

3 beds2.5 baths2,215 sq ft

8 Lieutenant River Ln, Old Lyme, CT 06371

High end kitchen • Full basement • Stone patio

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Tucked along Trolley Road in Westbrook, this year-round cottage offers a rare opportunity in one of the shoreline's most sought-after locations. The home itself is ready for a new owner's vision and care, but it's the walk-to-town lifestyle that makes this property truly special. Just steps from Christie's, Julie's Cup of Joe, The Turtle Cafe, and the Westbrook train station, you'll enjoy the ease of downtown living while still being south of Route 1 and within walking distance to Westbrook's sandy beaches. Set on a generous, level lot, with test holes already completed, the property offers incredible potential well beyond its current footprint. A small section of wetlands rests quietly at

$375,000

2 beds1 bath573 sq ft

41 Trolley Rd, Westbrook, CT 06498

Generous level lot • Natural privacy • 0.29 acre lot

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
The Parker Bull House, circa 1754, is one of the oldest historic homes in Essex. Located in Ivoryton overlooking the Falls River, this stately home is a unique blend of original antique features with updated modern amenities. The large sunny kitchen has granite countertops and stainless-steel appliances, hardwood floors, and is adjacent to a spacious pantry/laundry room, heated sunroom, and a covered porch. The living room has a large fireplace and antique wide board floors, leading to a formal dining room with another fireplace and beehive oven. A parlor serves as a comfortable family room, and there is also a powder room on the first floor. Upstairs, the primary bedroom includes a wood-fl

$824,900

3 beds2.5 baths2,456 sq ft

45 Main St, Essex, CT 06442

Covered porch • Heated sunroom • Large sunny kitchen

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 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 34 Lyme St, Old Lyme, CT 06371, 2 beds, 2 baths

$550,000

2 beds2 baths2,548 sq ft

34 Lyme St, Old Lyme, CT 06371

Property at 1 & 3 Neck Rd, Old Lyme, CT 06371, 4 beds, 3.5 baths

$2,800,000

4 beds3.5 baths6,742 sq ft

1 & 3 Neck Rd, Old Lyme, CT 06371

Vintage Homes for Sale in Old Saybrook

There are currently 14 vintage homes for sale in Old Saybrook at a median listing price of $890K. 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 79 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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