Old Saybrook, CT Homes

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  $849,000

  • 5 Beds
  • 3 Baths
  • 2,898 Sq Ft

  26 College St, Old Saybrook, CT 06475

  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

  Tammy Tinnerello William Pitt Sotheby's Int'l

  26 College St, Old Saybrook, CT 06475
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  $3,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,137 Sq Ft
  • House for Rent

  8 Clinton Ave, Old Saybrook, CT 06475

  Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor

  Terry McDonald McDonald Real Estate, LLC

  8 Clinton Ave, Old Saybrook, CT 06475
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  $800,000 Sold Jul 29, 2025

  92 Fenwood Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $442/SF
  • 2 Days On Market

  Current Estimated Value $793,196

  Last Listing Agent Fran Manganello Coldwell Banker Realty

  92 Fenwood Dr, Old Saybrook, CT 06475
• 

  Est $6,670,601 Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 7,465 Sq Ft

  9 Pettipaug Ave, Old Saybrook, CT 06475

  9 Pettipaug Ave, Old Saybrook, CT 06475
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  $425,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  227 Essex Rd, Old Saybrook, CT 06475

  Nestled on a .93 Acre corner lot this 3 Bedroom Ranch offers one floor living. Fireplace in Living Room, Eat-In Kitchen, Vinyl siding, a four year old roof plus gutter guards for easy maintenance. The Lower Level features a Den/Family Room with a built-In Bar. Enjoy the convenience of a 2 bay garage with door openers during inclement weather. Easy access to Rt 9, I95 or the train station for the

  Sandy Orsie Berkshire Hathaway NE Prop.

  227 Essex Rd, Old Saybrook, CT 06475
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  $3,200 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • House for Rent

  10 W View Rd, Old Saybrook, CT 06475

  Beautiful Knollwood Beach winter rental available immediately through 5/31/26. Enjoy living one block from LIS with lovely walking path along the waterfront and association amenities like tennis, and a great park with playground and basketball court. Nicely decorated and never rented before. Lovely livingroom with fireplace , 3 bedrooms, one bathroom. Oversized one car garage ok for tenant

  Joel Lucas Coldwell Banker Realty

  10 W View Rd, Old Saybrook, CT 06475
• 

  $742,900 Sold Oct 31, 2025

  16 Howard St, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $529/SF
  • 3 Days On Market

  Last Listing Agent Terry Kemper Coldwell Banker Realty

  16 Howard St, Old Saybrook, CT 06475
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  Est $783,450 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,673 Sq Ft

  16 Fordham Trail, Old Saybrook, CT 06475

  16 Fordham Trail, Old Saybrook, CT 06475
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  $939,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,286 Sq Ft

  1 Lighthouse Ln, Old Saybrook, CT 06475

  LOCATION, LOCATION, LOCATION! This spacious 3200 sq.ft. home offers BEAUTIFUL WATER VIEWS and an UNBEATABLE LOCATION in one of the shoreline's most sought-after communities. Perfectly situated between Saybrook Point and Town Center, it's just a short walk in either direction to enjoy marinas, top-rated restaurants, boutique shopping, and local favorites like the Saybrook Inn. This cul-de-sac

  Lynne Ferrigno Coldwell Banker Realty

  1 Lighthouse Ln, Old Saybrook, CT 06475
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  /18

  $2,400 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  9 Red Bird Trail, Old Saybrook, CT 06475

  SHORT TERM RENTAL until mid May 2026. Three BR Colonial with Sun Room located in the beautiful Indian Town Association. Views of LIS and harbor. Bright and spacious rooms. This location is perfect for walking, biking or strolling along the beach. Conveniently located to I95, Train Station, Shopping and The Kate. Sorry NO pets or smokers allowed.

  Sandy Orsie Berkshire Hathaway NE Prop.

  9 Red Bird Trail, Old Saybrook, CT 06475
• 

  $775,000 Sold Aug 05, 2025

  16, 18 Bayberry Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1958

  Last Sold Summary

  • 9% Below List Price
  • $1,009/SF
  • 97 Days On Market

  Last Listing Agent Cherie Suhie J.M. REALTY

  16, 18 Bayberry Rd, Old Saybrook, CT 06475
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  Est $604,027 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft

  1 Anchorage Ln, Old Saybrook, CT 06475

  1 Anchorage Ln, Old Saybrook, CT 06475
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  $519,000

  • 2 Beds
  • 1.5 Baths
  • 1,557 Sq Ft

  118 Sandy Point Rd, Old Saybrook, CT 06475

  Summerwood on the Sound. Step into this stunning townhouse condominium featuring a fabulous kitchen with spacious quartz counters and breakfast bar, custom designed cabinetry and stainless steel appliances. The open concept living room and dining area boast beautiful wood flooring, elegant crown molding and glass doors to the private deck area, perfect for relaxing and entertaining. There is also

  Carla Mousch William Raveis Real Estate

  118 Sandy Point Rd, Old Saybrook, CT 06475
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  $6,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,510 Sq Ft
  • House for Rent

  29 W Shore Dr, Old Saybrook, CT 06475

  Welcome to 29 W.Shore Dr. Old Saybrook,CT. A direct waterfront single family home retreat in the Cornfield Point Association, is now available for academic term to begin Oct 1 - April 30 offering fully furnished 4 bedrooms, 3 baths, Fireplace, laundry on main level, 1 car garage, oversize waterfront lot and much more. Great opportunity for the short term rental, who enjoys water views with

  David Rodriguez William Pitt Sotheby's Int'l

  29 W Shore Dr, Old Saybrook, CT 06475
• 

  $620,000 Sold Jul 31, 2025

  37 Woodland Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 22% Below List Price
  • $413/SF
  • 94 Days On Market

  Current Estimated Value $643,475

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
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  Est $1,221,626 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,010 Sq Ft

  41 Cypress Rd, Old Saybrook, CT 06475

  41 Cypress Rd, Old Saybrook, CT 06475
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  $1,075,000 Open Mon 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft

  122 Old Post Rd, Old Saybrook, CT 06475

  Did you ever dream of owning two vacation homes, one near the water within walking distance to a beach, and another quiet cabin somewhere in the mountains or woods where you are surrounded by natural beauty? This unique home is both! Tucked away on 2+ private acres in the coveted Indian Town Beach Association, it is a spacious custom-built post and beam timber frame with amenities that rival a

  Susan Malan William Pitt Sotheby's Int'l

  122 Old Post Rd, Old Saybrook, CT 06475
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  $2,800 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft
  • House for Rent

  38 Mohican Rd, Old Saybrook, CT 06475

  This home is just one short block from the beach and has a nice sized yard with a patio and outdoor shower. The roomy kitchen opens to a large great room with a gas burning stove. There is also a separate living room to the front of the house. This home has plenty of room for parking and is a member of Cornfield Point with two beaches, a club house, pickleball court, tennis court and activities

  Bonnie Fillion Berkshire Hathaway NE Prop.

  38 Mohican Rd, Old Saybrook, CT 06475
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  $600,000 Sold Mar 24, 2025

  9 Trolley Crossing, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $413/SF
  • 40 Days On Market

  Current Estimated Value $609,327

  Last Listing Agent Jackie Lyman Lyman Real Estate

  9 Trolley Crossing, Old Saybrook, CT 06475
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  Est $693,472 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  10 Allendale Rd, Old Saybrook, CT 06475

  10 Allendale Rd, Old Saybrook, CT 06475
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  $2,195,000

  • 1 Bed
  • 1.5 Baths
  • 7,985 Sq Ft

  125 Main St, Old Saybrook, CT 06475

  Great mixed-use opportunity. Fully leased office building with town-approved one-bedroom apartment on Second Floor with kitchen, full bath including washer/dryer. Great opportunity to own a mixed-use property on beautiful Main Street in Old Saybrook. Established salon with long term lease on first floor. The one bedroom apartment on the second floor has been carpeted and painted and has separate

  Gary Marino William Raveis Real Estate

  125 Main St, Old Saybrook, CT 06475
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  /2

  $2,950 total monthly price

  • 2 Beds
  • 2 Baths
  • 994 Sq Ft
  • Apartment for Rent

  109 Lynde St Unit 4, Old Saybrook, CT 06475

  WELCOME TO THE LUXURY HANFORD COMMONS, LOCATED IN THE TOWN OF OLD SAYBROOK WHICH IS KNOWN FOR ITS BEACHES, MARINAS, SHOPPING, FINE DINING, GALLERIES AND THE FAMOUS KATHERINE HEPBURN THEATER, MOST OF WHICH IS WALKING DISTANCE FROM THE APARTMENT COMPLEX. THIS FIRST FLOOR UNIT IS A TWO BEDROOM, TWO BATH, RANCH STYLE APARTMENT WITH LOTS OF NATURAL LIGHT FROM THE OVERSIZED WINDOWS. UNIT ALSO HAS

  Tracy Bonito William Raveis Real Estate

  109 Lynde St Unit 4, Old Saybrook, CT 06475
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  $575,000 Sold May 15, 2025

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,898 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $303/SF
  • 57 Days On Market

  Current Estimated Value $582,764

  Last Listing Agent Carla Mousch William Raveis Real Estate

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475
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  Est $2,465,243 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,225 Sq Ft

  468 Main St, Old Saybrook, CT 06475

  468 Main St, Old Saybrook, CT 06475
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  $750,000 Open House 1/03

  • 2 Beds
  • 2.5 Baths
  • 1,751 Sq Ft

  41 Briarwood Dr, Old Saybrook, CT 06475

  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

  Rick Allen William Raveis Real Estate

  41 Briarwood Dr, Old Saybrook, CT 06475
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  $3,500 total monthly price

  • 3 Beds
  • 1 Bath
  • 884 Sq Ft
  • House for Rent

  24 W Shore Dr, Old Saybrook, CT 06475

  Welcome to this beautiful neighborhood charm located in the great Cornfield Point Association, Old Saybrook,CT. Coastal inspired furnished 3 bed 1 bath, home features stunning water views and just steps away from the Cornfield Point Beach and community. Now is the time to reserve this home for academic rental from October 1 - May15. Cozy living-room with stunning Ocean views and entertainment

  David Rodriguez William Pitt Sotheby's Int'l

  24 W Shore Dr, Old Saybrook, CT 06475
• 

  $890,999 Sold Apr 24, 2025

  49 Atlantic Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Above List Price
  • $543/SF
  • 0 Days On Market

  Current Estimated Value $911,583

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  49 Atlantic Dr, Old Saybrook, CT 06475
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  Est $624,016 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,290 Sq Ft

  21 Baum Ave, Old Saybrook, CT 06475

  21 Baum Ave, Old Saybrook, CT 06475
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  $749,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  20 Hill St, Old Saybrook, CT 06475

  This FEMA compliant coastal residence in Old Saybrook offers panoramic views of South Cove at the mouth of the Connecticut River, where the river meets the sound. The property features a new deck, providing an ideal vantage point for observing the sunrise and local wildlife each morning, as well as evening views of Lynde Lighthouse and passing boats.The house has been lifted out of the flood

  Pardi & Zucco Team William Pitt Sotheby's Int'l

  20 Hill St, Old Saybrook, CT 06475
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  $6,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft
  • House for Rent

  7 Saye St, Old Saybrook, CT 06475

  Welcome to Old Saybrook! This beautifully furnished 6-room home offers 3 spacious bedrooms, 2 full baths, and 1,784 sq ft of living space. Nestled just a short walk from the beach, you'll enjoy full access to Chalker Beach, a serene stretch along the Long Island Sound known for its soft sands and peaceful atmosphere-ideal for sunbathing, swimming, and coastal relaxation. Step out onto your

  John Lynch William Raveis Real Estate

  7 Saye St, Old Saybrook, CT 06475
• 

  $935,000 Sold Dec 16, 2025

  19 Lynde St, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • Built 1918

  Last Sold Summary

  • 1% Above List Price
  • $390/SF
  • 62 Days On Market

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  19 Lynde St, Old Saybrook, CT 06475
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  Est $647,691 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,170 Sq Ft

  8 East St, Old Saybrook, CT 06475

  8 East St, Old Saybrook, CT 06475
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  $799,900

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  21 Fenwick St, Old Saybrook, CT 06475

  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.

  Paula Stuart Berkshire Hathaway NE Prop.

  21 Fenwick St, Old Saybrook, CT 06475
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  /19

  $2,400 total monthly price

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  38 Seabreeze Rd, Old Saybrook, CT 06475

  Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with three bedrooms, an updated bathroom, eat-in kitchen, living room with fireplace, a wonderful sun porch and an outside

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
• 

  $377,000 Sold Oct 08, 2025

  52 Chalker Beach Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1948

  Last Sold Summary

  • 16% Below List Price
  • $337/SF
  • 77 Days On Market

  Last Listing Agent Patrick Farley Statewide Premier Prop. LLC

  52 Chalker Beach Rd, Old Saybrook, CT 06475
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  Est $578,609 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,288 Sq Ft

  18 Pheasant Hill Ln, Old Saybrook, CT 06475

  18 Pheasant Hill Ln, Old Saybrook, CT 06475
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  $19,000 Pending

  • Land
  • 0.8 Acre
  • $23,750 per Acre

  0 Merritt Ln, Old Saybrook, CT 06475

  NOT BUILDABLE LOT! .80 acres overlooking Chalkers Millpond on cul-de-sac .

  Claude Cousins Berkshire Hathaway NE Prop.

  0 Merritt Ln, Old Saybrook, CT 06475
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  $5,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • House for Rent

  25 W Shore Dr, Old Saybrook, CT 06475

  BEACHFRONT Beautifully renovated Furnished luxury waterfront monthly rental for annually $10,000 or winter for $5900 a month 9/30/25 to 5/15/26 (some flexibility with dates). $1200 a day for June 1st thru Sept. 15th. Waterviews from all rooms, private beach, plus cornfield point assocation amenties. Enjoy 3 bedrooms all with water-views, 2 full bathrooms, 1 half bathroom, fireplace, CA, new

  Joel Lucas Coldwell Banker Realty

  25 W Shore Dr, Old Saybrook, CT 06475
• 

  $358,000 Sold Nov 10, 2025

  Unlisted Address

  • 1 Bed
  • 1 Bath
  • 1,111 Sq Ft
  • Built 1800

  Last Sold Summary

  • 6% Above List Price
  • $322/SF
  • 2 Days On Market

  Last Listing Agent Jeanette Baigert Berkshire Hathaway NE Prop.

  Unlisted Address
• 

  Est $672,691 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft

  28 Attawanhood Trail, Old Saybrook, CT 06475

  28 Attawanhood Trail, Old Saybrook, CT 06475

Showing Results 41 - 80, Page 2 of 18