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:
Welcome to your dream home! This charming 3-bedroom, 2-bath gem offers comfort, style, and privacy in every corner. Step inside to find beautifully renovated bathrooms, sleek new windows, and Mitsubishi AC splits throughout, including the basement, for year-round comfort. The attached garage adds convenience, while the partially finished basement with a bulkhead offers extra space for hobbies or storage. While the current homeowners work from home, reimagine the bedrooms to suit your needs. The primary is large enough for a king-sized bed and dresser. Consider bedroom two for guests with a queen-sized bed, dresser, and possibly a compact desk space. Bedroom three is perfect for the youngest

$654,000

3 beds2 baths1,664 sq ft

21 Farview Ave, Old Saybrook, CT 06475

Newly built shed • Renovated bathrooms • Mitsubishi ac splits

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Tucked at the end of a quiet cul-de-sac in Old Saybrook Center, 24 Cottage Place offers a rare blend of coastal elegance and modern comfort. This move-in ready 4-bedroom, 3-bath home is just steps from Main Street's shops and restaurants (0.2 mi), The Kate and library (0.3 mi), fitness center (0.4 mi), marinas and waterfront access (0.5 mi), and the train station (0.6 mi)-delivering the ultimate walkable shoreline lifestyle. Inside, sun-filled living spaces showcase gleaming hardwood floors and an open, versatile layout. The designer kitchen features white cabinetry, granite counters, and a large island-perfect for gatherings. A first-floor bedroom offers flexible use or en suite potential.

$960,000

4 beds3 baths2,516 sq ft

24 Cottage Pl, Old Saybrook, CT 06475

Designer kitchen • First-floor bedroom • Quiet cul-de-sac

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
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, a huge bonus room you can convert to a third bedroom, 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 cab

$1,045,000

2 beds2 baths1,952 sq ft

24 Seabreeze Rd, Old Saybrook, CT 06475

Huge bonus room • Thermopane windows • Vinyl siding

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Enjoy your summers at Cornfield Point with a 5 bedroom Colonial with large of space for everyone. After a refreshing day at the beach come home to plenty of space for fun family gatherings. Parking is plentiful with extra storage. Your summers can be filled with boating, beaching, amazing sunsets, and fine dining at a many local restaurants. Don't miss your change to chance to live in Cornfield Point. brand new heat and a/c new windows kitchen and baths . all permits closed ready for your new life at the beach

$985,000

5 beds2.5 baths3,472 sq ft

Town Beach Rd, Old Saybrook, CT 06475

Kitchen and baths • New heat and a/c • New windows

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Best location in Indiantown Beach Association! This charming year-round waterfront cottage comes with its very own private beach and breathtaking views of Long Island Sound. Just under 600 sq ft, it sits on a . 12-acre lot offering rare expansion potential. A spacious deck overlooks the water, perfect for morning coffee or evening sunsets, with sliders from both the living room and bedroom creating seamless indoor-outdoor living. Inside, beautiful hardwood floors, a brick fireplace for cozy winter nights, and an ample kitchen complete the picture of relaxed coastal charm. Just a one-minute walk brings you to one of the association's pristine beaches and the clubhouse, while the association

$1,190,000

1 bed1 bath578 sq ft

174 Nehantic Trl, Old Saybrook, CT 06475

Breathtaking views • Brick fireplace • Expansion potential

Property at 26 College St, Old Saybrook, CT 06475, 5 beds, 3 baths

$895,000

5 beds3 baths2,898 sq ft

26 College St, 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 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 18 Quarry St, Old Saybrook, CT 06475, 4 beds, 2 baths

$630,000

4 beds2 baths1,760 sq ft

18 Quarry St, Old Saybrook, CT 06475

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 13 College St, Old Saybrook, CT 06475, 1 bed, 1 bath

$450,000

1 bed1 bath576 sq ft

13 College St, Old Saybrook, CT 06475

Property at 355 Main St, Old Saybrook, CT 06475, 3 beds, 1.5 baths

$729,000

3 beds1.5 baths2,194 sq ft

355 Main St, Old Saybrook, CT 06475

Property at 23 Briarwood Dr, Old Saybrook, CT 06475, 3 beds, 2 baths

$975,000

3 beds2 baths2,000 sq ft

23 Briarwood Dr, 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 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

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

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NEW 34 HRS AGO

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-

$80,000

1 bed1 bath440 sq ft

8 Cook Ter, Westbrook, CT 06498

$830 HOA • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Set in the heart of Centerbrook Village, this 1917 Colonial captures the timeless charm of Essex with all the right updates in place. Thoughtfully redesigned by Nautilus Architects, the kitchen blends classic craftsmanship with modern function - complemented by refinished hardwood floors, updated systems, and a new matched central air system with upgraded condenser and coil. Upstairs, the reimagined primary suite now includes a full ensuite bath and custom closet configuration, creating a true retreat. Recent 2024 improvements include a new roof, renovated bath, AC system replacement, fresh paint, and upgraded trim throughout. Outside, the half-acre lot offers space to unwind with a fenced

$800,000

3 beds2.5 baths1,863 sq ft

126 Main St, Centerbrook, CT 06409

0.49 acre lot • Garage • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Nestled in the heart of historic Essex Village, this charming 2-bedroom, 2-bath Carriage House offers 1,076 sq. ft. of thoughtfully designed living space that perfectly blends historic charm with modern comfort. Just a short stroll from the Connecticut River, local marinas, museums, boutique shops, fine dining, and the iconic Griswold Inn, this home embodies the quintessential Essex lifestyle. Natural sunlight fills the interior, creating a warm and inviting atmosphere throughout. The living room features built-ins and a wood-burning fireplace, adding to the home's cozy New England character. The tiered gardens that surround the property provide privacy and a peaceful outdoor retreat-ideal

$669,000

2 beds2 baths1,076 sq ft

16 N Main St, Essex, CT 06426

3,049 sq ft lot • 2 garage spots • Somewhat walkable

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Don't miss this rare opportunity to own 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-

$1,200,000

1 bed3 baths3,384 sq ft

24 Lyme St, Old Lyme, CT 06371

9,147 sq ft lot • Car-dependent

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 baths2,680 sq ft

8 Lieutenant River Ln, Old Lyme, CT 06371

9,147 sq ft lot • Garage • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Old Saybrook, CT:
Investor Special - 7 Earl Street | Full Gut Renovation Opportunity Calling all savvy investors and visionary flippers! 7 Earl Street is your next big opportunity. This estate property is being sold as-is and is ready for a complete transformation. The structure appears solid, but the interior needs a complete gut and rebuild. There is currently no kitchen or working bathroom, and a past pipe burst has left its mark-expect water damage throughout. This is not for the faint of heart, but for those with the vision and resources, the potential is huge. Whether you're looking to flip for profit or build a custom rental, this blank canvas is ready for your plans. Enter at your own risk - personal

$299,900

3 beds1 bath1,060 sq ft

7 Earl St, Centerbrook, CT 06409

0.31 acre lot • 2 garage spots • Car-dependent

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 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 33 Sill Ln, Old Lyme, CT 06371, 3 beds, 3.5 baths

$950,000

3 beds3.5 baths2,011 sq ft

33 Sill Ln, Old Lyme, CT 06371

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

$1,400,000

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

$1,675,000

4 beds2.5 baths2,634 sq ft

18 Benson Ln, Essex, CT 06426

Property at 32 Main St, Ivoryton, CT 06442, 4 beds, 2.5 baths

$605,000

4 beds2.5 baths2,402 sq ft

32 Main St, Ivoryton, CT 06442

Property at 60 Lyme St, Old Lyme, CT 06371, 3 beds, 2 baths

$1,395,000

3 beds2 baths3,113 sq ft

60 Lyme St, Old Lyme, CT 06371

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

$595,000

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 16 vintage homes for sale in Old Saybrook at a median listing price of $857K. 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 77 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 6 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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