Homes for Sale near Old Saybrook Senior High School

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  /33

  $575,000

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  5 Aladdin Ave, Old Saybrook, CT 06475

  GET YOUR SPOT AT THE BEACH! The perfect getaway, just a short walk from the Chalker Beach Sandy Shoreline. Ready for love, sun, swim, and enjoying all the fun-with no traffic and plenty of relaxation right outside this home. A spacious deck overlooks a beautiful backyard, ideal for entertaining family and friends. Rinse off the day in the outdoor shower. Chalker Beach offers an abundance of

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 590-4441

  5 Aladdin Ave, Old Saybrook, CT 06475
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• 

  

  

  /37

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  14 Meadowood Ln, Old Saybrook, CT 06475

  Make this warm, inviting home your own this spring! Ideally located in one of the most desirable neighborhoods in town and conveniently located a short walk to the high school and close to beaches and the village. This home offers a very flexible floor plan with hardwood floors, a new roof and recently replaced septic system. A spacious, private deck with a hot tub complete the package! Schedule

  

  Rick Allen

  William Raveis Real Estate

  (860) 773-4719

  14 Meadowood Ln, Old Saybrook, CT 06475
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  /40

  $949,000

  • 4 Beds
  • 2 Baths
  • 2,249 Sq Ft

  86 Chalker Beach Rd, Old Saybrook, CT 06475

  Welcome to Year-Round Beach Living with Room to Spare! Welcome to 86 Chalker Beach Rd. Do you desire a year-round beach home with plenty of space? Look no further! Welcome to 86 Chalker Beach Rd-your gateway to coastal living in one of Old Saybrook's most vibrant beach communities. With nearly 2,300 square feet of living space, this rare find offers four spacious bedrooms and two full bathrooms,

  

  Jodi Serapilia

  William Raveis Real Estate

  (860) 809-5460

  86 Chalker Beach Rd, Old Saybrook, CT 06475
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  /40

  $899,000

  • 3 Beds
  • 2 Baths
  • 2,297 Sq Ft

  12 4th Ave, Old Saybrook, CT 06475

  Huge Price reduction! Nestled on Ferry Point, where the Ct River meets the L.I. Sound, this charming waterfront home offers breathtaking views and direct access to the water. The private dock, complete with Jet ski port and well suited to an array of different boat designs,invites endless maritime adventures. Enjoy watching Osprey on their nest along with boats drifting by from the kitchen,

  

  Maddy Mattson

  Coldwell Banker Realty

  (860) 787-8257

  12 4th Ave, Old Saybrook, CT 06475
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  /28

  $1,100,000

  • 4 Beds
  • 2 Baths
  • 2,376 Sq Ft

  1 Clark Ave, Old Saybrook, CT 06475

  Imagine slipping your kayak into the tidal waters of Hagar Creek from your spacious backyard, and gliding through the morning's sun-dappled marsh to find yourself entering Long Island Sound. Maybe do a little fishing, or just drink in the stunning shoreline views? Time to head home for lunch. Check the newsletter to see what's going on at the community center tonight. Then it's a quick spin down

  Rick Weiner William Pitt Sotheby's Int'l

  1 Clark Ave, Old Saybrook, CT 06475
• 

  

  /39

  $1,695,000

  • 3 Beds
  • 3 Baths
  • 1,994 Sq Ft

  118 Old Sea Ln, Old Saybrook, CT 06475

  Here is the home you have been waiting for. Built from the ground up in 2020, this modern three-bedroom colonial has amazing unobstructed views of Long Island Sound. Located in Indian Town, one of Old Saybrook's sought-after beach communities, with two sandy beaches, a marina, and a clubhouse. The open floor main level has sliders to an outside deck where you can enjoy the summer breezes off the

  Nick Prevost William Raveis Real Estate

  118 Old Sea Ln, Old Saybrook, CT 06475
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  /40

  $1,790,000

  • 3 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  2 Old South Cove Rd, Old Saybrook, CT 06475

  Step into a lifestyle of refined coastal luxury at 2 Old South Cove Rd, Old Saybrook's most stylish new construction. Perfectly positioned just steps from the water, this 2,400 sq ft masterpiece blends modern design with timeless comfort-crafted in partnership with Saybrook Home and styled like a New York design editorial. Enjoy water views and dramatic light-filled spaces with soaring 9'-22'

  Michael Riccio Calcagni Real Estate

  2 Old South Cove Rd, Old Saybrook, CT 06475
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  /40

  $1,335,000

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  122 Old Post Rd, Old Saybrook, CT 06475

  Welcome home to your own exquisite coastal retreat. This award winning exceptional cedar 3,000 square feet home blends timeless craftsmanship with modern upgrades and includes a stunning 19 foot high great room with floor to wall ceilings, wrap around deck with effortless indoor-outdoor living, cozy fireplace, dining room and family room. The kitchen boasts custom counters and cabinetry,

  Sharon Linder Berkshire Hathaway NE Prop.

  122 Old Post Rd, Old Saybrook, CT 06475
• 

  

  /40

  $1,545,000

  • 3 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  26 Meadowood Ln, Old Saybrook, CT 06475

  Welcome to 26 Meadowood Drive - where sophisticated coastal living meets modern comfort. This stunning new construction Colonial, completed in 2025, offers breathtaking water views of Long Island Sound and Hagar Creek, all while providing peace of mind outside the flood zone. Step inside this thoughtfully designed 3-bedroom, 2.5-bath retreat and experience natural light, red oak hardwood floors,

  Jennifer Gurnell William Raveis Real Estate

  26 Meadowood Ln, Old Saybrook, CT 06475
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  /26

  $1,200,000

  • 4 Beds
  • 2 Baths
  • 3,200 Sq Ft

  122 College St, Old Saybrook, CT 06475

  Iconic Old Saybrook 1890's Captain's home with it's own widow's walk-venture up and enjoy 360 degree views of the CT River, North Cove, and Long Island Sound-or relax on the wrap around porch and watch the world go by. Situated on .80 level acres w/an inground pool-2 car detached garage w/1/2 bath for the pool-possibly could be renovated for guest quarters. This home is like a blank slate w/3200

  Mary McDonald Coldwell Banker Realty

  122 College St, Old Saybrook, CT 06475
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  /34

  $1,050,000

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  55 Cypress Rd, Old Saybrook, CT 06475

  Perched above the beautiful meadows in the desirable beach community of Knollwood, this property is a gem. Whether you would like to walk or take your golf cart to the beach, entertain on your deck in your backyard oasis or launch your kayak out your back door, you can have a sweet life here! A gorgeous new eat-in kitchen with high end appliances and a fireplace, is the icing on the cake of this

  Tina Rupp William Pitt Sotheby's Int'l

  55 Cypress Rd, Old Saybrook, CT 06475
• 

  

  /40

  $1,550,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  35 Soundview Ave, Old Saybrook, CT 06475

  South Cove property with spectacular, panoramic views extending out to the Connecticut River and Long Island Sound. Recently updated and move-in ready, this year-round home offers the perfect harmony of tranquility and convenience. Nestled in a peaceful neighborhood yet walking distance to Main Street and Saybrook Point. And, less than 2 miles to the town beach. Enjoy expansive water vistas from

  Sue Darmon William Pitt Sotheby's Int'l

  35 Soundview Ave, Old Saybrook, CT 06475
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  /40

  $1,145,000

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

  1 Lighthouse Ln, Old Saybrook, CT 06475

  Set in coveted Saybrook Point, this Cape-style home blends coastal charm with thoughtful custom touches, offers STUNNING WATER VIEWS and is walkable to both the Point and town center. A spacious (3200+ sq.ft) home, features include built-ins, cabinetry, crown moldings and bay windows framing views of South Cove from multiple rooms. Step outside to a stone patio set beneath a graceful pergola,

  Lynne Ferrigno Coldwell Banker Realty

  1 Lighthouse Ln, Old Saybrook, CT 06475
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  /40

  $998,900

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

  26 College St, Old Saybrook, CT 06475

  Welcome to 26 College Street, a Nantucket-style haven nestled in the heart of historic Old Saybrook-a coastal village where charm meets convenience. With five spacious bedrooms and three full bathrooms, including a fully private in-law or au-pair suite, it's tailor-made for families or couples looking for multi-generational living, rental income, or a dedicated home office setup. Tucked between

  Joel Lucas Coldwell Banker Realty

  26 College St, Old Saybrook, CT 06475
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  /33

  $1,150,000 Open House 7/20

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  21 Wildwood Rd, Old Saybrook, CT 06475

  Imagine waking up to breathtaking marsh views and stunning sunsets from your very own slice of paradise in the highly desirable Cornfield Point waterfront community. This nearly 1-acre lot offers endless possibilities - whether you choose to expand, rebuild, or simply enjoy the charm of the existing 1,408 square foot home. The current residence features 3 bedrooms, 1.5 baths, a spacious 2-car

  Marc Delise Coldwell Banker Realty

  21 Wildwood Rd, Old Saybrook, CT 06475
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  /28

  $1,085,000

  • 2 Beds
  • 2 Baths
  • 1,952 Sq Ft

  24 Seabreeze Rd, Old Saybrook, CT 06475

  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

  Brian Beaulieu KW Legacy Partners

  24 Seabreeze Rd, Old Saybrook, CT 06475
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  /40

  $775,000

  • 2 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  100 Dudley Ave Unit B8, Old Saybrook, CT 06475

  Welcome to Desirable Sheltered Cove! This beautifully updated 2-bedroom, 2.5 bath condo offers light-filled interiors, hardwood floors, recessed lighting, and elegant crown molding throughout. Enjoy breathtaking views of North Cove from the living room, dining area, kitchen, and even your primary bedroom. The remodeled kitchen is a chef's dream, featuring stainless steel appliances including an

  Rose Ciardiello William Raveis Real Estate

  100 Dudley Ave Unit B8, Old Saybrook, CT 06475
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  /34

  $585,000

  • 2 Beds
  • 1.5 Baths
  • 1,258 Sq Ft

  16 Lynde St, Old Saybrook, CT 06475

  Unbeatable downtown Old Saybrook location! This well-maintained Cape Cod-style home at 16 Lynde Street is on the market for the first time in over 40 years. Offering 2+ bedrooms, 1+ baths, and a bright, flexible floor plan, this property places you in the heart of one of Connecticut's most desirable shoreline towns. Enjoy sidewalks leading to schools, the library, shops, restaurants, cafes, and

  Jennifer Gurnell William Raveis Real Estate

  16 Lynde St, Old Saybrook, CT 06475
• 

  

  /18

  $189,900

  • Land
  • 0.16 Acre
  • $1,186,875 per Acre

  6 South St, Old Saybrook, CT 06475

  Build Your Dream Home in Coastal Old Saybrook! A rare opportunity awaits you... Are you ready to create your shoreline oasis? Look no further than this Fully Approved Residential Building Lot with many enticing features that make it a special gem. Come enjoy salty breezes and serene water views... sunsets and seagulls await! Located in a residential neighborhood on a road with two other homes

  Cheryl Keithan Coldwell Banker Realty

  6 South St, Old Saybrook, CT 06475
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  /36

  $685,000

  • 3 Beds
  • 3.5 Baths
  • 2,660 Sq Ft

  18 W King St, Old Saybrook, CT 06475

  Discover exceptional flexibility, Airbnb potential, and income opportunity at 18 King Street in the heart of Old Saybrook. This updated ranch-style home offers over four spacious bedrooms, three and a half modern baths, and two fully renovated kitchens-ideal for multigenerational living, private guest quarters, or short- and long-term rental income. Energy-efficient split systems and

  Jennifer Gurnell William Raveis Real Estate

  18 W King St, Old Saybrook, CT 06475
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  /40

  $4,450,000

  • 6 Beds
  • 4.5 Baths
  • 5,536 Sq Ft

  41 Watrous Point Rd, Old Saybrook, CT 06475

  Presenting a single level light-filled mid-century modern masterpiece, set on a prominent 2.7 acre private waterfront peninsula! Enjoy 875' of frontage along the CT River and adjacent Turtle Creek nature preserve. This dreamlike property comes with two docks. A deep water dock on the river, plus a second dock on Turtle Creek! Drink in views from Essex Harbor to the north, across the river to Old

  Rick Weiner William Pitt Sotheby's Int'l

  41 Watrous Point Rd, Old Saybrook, CT 06475
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  /38

  $2,100,000

  • 3 Beds
  • 2 Baths
  • 3,477 Sq Ft

  5 Oakwood Rd, Old Saybrook, CT 06475

  This spacious Knollwood Beach home is only ONE house from Long Island Sound featuring sweeping water views. Step into timeless elegance with this stunning home where classic craftsmanship meets modern convenience. The first floor features a gourmet kitchen and dining area complete with granite countertops, a center island with canopy, and high-end appliances. Original wainscoting ceilings and two

  Carol Ieronimo William Raveis Real Estate

  5 Oakwood Rd, Old Saybrook, CT 06475
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  /22

  $649,900

  • 3 Beds
  • 1 Bath
  • 870 Sq Ft

  96 Chalker Beach Rd, Old Saybrook, CT 06475

  This charming 3-bedroom, 1-bathroom home offers all the cozy beach vibes you've been looking for. Pull into the paver stone driveway with room for multiple vehicles, golf carts, or beach cruisers. A shed at the end of the driveway provides easy storage for all your beach gear. Step into the beautifully manicured, fully fenced backyard complete with a paver stone patio, open lawn for play or

  Danielle Spada Coldwell Banker Realty

  96 Chalker Beach Rd, Old Saybrook, CT 06475
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  /39

  $699,900

  • 3 Beds
  • 2 Baths
  • 1,762 Sq Ft

  1 Hartford Ave, Old Saybrook, CT 06475

  Welcome to Saybrook Manor! This sprawling year-round beach home is a perfect blend of rustic beach charm and modern day amenities. Situated on a large double corner lot this home has deeded beach rights to the Saybrook Manor beaches at the end of Middletown Ave and Hartford Ave. Just a quick walk or golf cart ride to the water, invite your family and friends to enjoy plenty of yard space and a

  Bryan Neurath Country Manor Realty

  1 Hartford Ave, Old Saybrook, CT 06475
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  /32

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft

  76 River St W, Old Saybrook, CT 06475

  Built to Last! Well Maintained Cape tucked away in a peaceful location backing up to Salt marshes. Nature lovers will enjoy the serene views of the salt meadows, wildlife and privacy of this quiet neighborhood. This property features 3 beds, 2 baths, over 1700 square feet of living space, a living room with vaulted ceilings and wall unit ac, dining area, kitchen, 3 good sized bedrooms, a private

  Robert Perriello Century 21 AllPoints Realty

  76 River St W, Old Saybrook, CT 06475
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  /25

  $558,900

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  14 Denmore Ln, Old Saybrook, CT 06475

  This beautifully revamped ranch style home provides a perfect blend of modern style and comfort. With 1,196 square feet of living space, this property boasts three spacious bedrooms and one full bathroom. The chef-inspired kitchen features sleek, new appliances, stylish cabinetry, and quartz countertops, ideal for both everyday meals and entertaining. The bright, airy living areas are enhanced

  Patrick Garrett Complete Real Estate

  14 Denmore Ln, Old Saybrook, CT 06475
• 

  

  /19

  $949,900

  • 3 Beds
  • 1 Bath
  • 762 Sq Ft

  27 Barnes Rd, Old Saybrook, CT 06475

  After being cherished by the same family for 70 years, this quintessential New England cottage ON THE WATER of Long Island Sound is ready for its next chapter. Located in the much sought after summer beach community of Great Hammock Beach, this property, situated on an oversized lot, offers direct access to fishing, swimming, kayaking and breathtaking sunset views from the deck. Inside, you'll

  Debra Pliego Essentia Realty

  27 Barnes Rd, Old Saybrook, CT 06475
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  /32

  $830,000

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  45 Knollwood Dr, Old Saybrook, CT 06475

  Just steps from the Knollwood Beach Association clubhouse, playground, and private beach, this beautifully updated raised ranch offers relaxed, coastal living in a peaceful environment. Inside, you'll find an open and airy main level, featuring a new kitchen with quartz counters, stainless GE appliances, and soft-close cabinetry, plus a dining area that opens to a deck - great for relaxing and

  Rose McWaid William Raveis Real Estate

  45 Knollwood Dr, Old Saybrook, CT 06475
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  /40

  $3,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,518 Sq Ft

  175 N Cove Rd, Old Saybrook, CT 06475

  Every home tells a story and the often admired c.1704 Black Horse Tavern in historic North Cove is no exception. Located at the waters edge and offering expansive water views, this stunning private residence is rich in both local history and architectural detail. Meticulously curated to perfection, quality of craftsmanship is evident throughout. A warm and welcoming entry leads to elegant

  Kyle Hinding Coldwell Banker Realty

  175 N Cove Rd, Old Saybrook, CT 06475
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  /13

  $399,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  3 4th Ave, Old Saybrook, CT 06475

  This home offers the one-level living you've been searching for! With a bit of repair work and thoughtful updates, you can transform this space into your perfect home. The property features a spacious backyard, complete with a generously sized outdoor shed for added storage and convenience. Close to marina, restaurants and highway access. Short drive to the beach!

  Phil Ledwith Century 21 AllPoints Realty

  3 4th Ave, Old Saybrook, CT 06475
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  /33

  $849,500

  • 3 Beds
  • 1 Bath
  • 890 Sq Ft

  78 Hartford Ave, Old Saybrook, CT 06475

  Beach living, redefined. Welcome to 78 Hartford Avenue, a rare coastal gem perched right on the water in the heart of Old Saybrook. With uninterrupted views, salty breezes, and your toes practically in the sand, this 3-bedroom beach retreat offers the kind of lifestyle most only dream about. Whether you're soaking in the sun from your patio, launching kayaks at sunrise, or hosting unforgettable

  Robert Perriello Century 21 AllPoints Realty

  78 Hartford Ave, Old Saybrook, CT 06475
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  /37

  $1,250,000

  • 3 Beds
  • 3 Baths
  • 2,132 Sq Ft

  15 Buckingham Ave, Old Saybrook, CT 06475

  Experience the epitome of coastal living in this stunning Hammock Beach Community residence, offering year-round water views and exclusive access to a private beach, just a short walk away. The first floor is an open and airy sanctuary, with sliders opening onto an expansive deck that invites the outside in and provides a seamless flow for indoor-outdoor living. The well-appointed kitchen and

  Colette Harron William Pitt Sotheby's Int'l

  15 Buckingham Ave, Old Saybrook, CT 06475
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  /5

  $575,000

  • Land
  • 0.48 Acre
  • $1,197,917 per Acre

  10 Mulberry St, Old Saybrook, CT 06475

  Approved building lot with water views. Located at the end of Mulberry, very private location yet close to downtown and Saybrook Point Resort & Marina. 1/2 ac already cleared. Lot must be sold with 7 Willard Ave

  Steve Wollman Wollman Realty

  10 Mulberry St, Old Saybrook, CT 06475
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  /17

  $850,000

  • Land
  • 26 Acres
  • $32,185 per Acre

  62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475

  Beautiful 26+ Acre Wooded Lot with Subdivision Potential. This stunning 26+ acre wooded parcel offers incredible potential for a variety of uses-from a private gentleman's farm to a multi-generational compound or subdivision development. Bucolic stone walls and mature trees create a serene, timeless setting. The sale includes parcels identified as Tax Map 62, Lots 14, 15, and 16. Access is

  Kevin Kennedy Kennedy Real Estate Solutions

  62-14,15,16 Middlesex Turnpike, Old Saybrook, CT 06475
• 

  

  /23

  $825,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  16, 18 Bayberry Rd, Old Saybrook, CT 06475

  Welcome to The Knollwood Beach Association with this charming property that offers water views from a sun filled porch as your daily backdrop. This year round ranch is being sold with the adjacent lot and a septic system installed in 2022 that will service up to a 5 bedroom home. While the interior retains its original charm and awaits your personal touch, the true star of this home is its

  Cherie Suhie J.M. REALTY

  16, 18 Bayberry Rd, Old Saybrook, CT 06475
• 

  

  /40

  $699,000

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

  37 Woodland Dr, Old Saybrook, CT 06475

  Welcome to Knollwood Beach Association, where charm, comfort, and nature meet in this beautifully updated year-round ranch-style home. Just two blocks from the sandy shores of Knollwood Beach, kayaking stands, tennis , pickleball and basketball courts, a playground, and the association clubhouse, this home is nestled along the Beamon Creek Estuary-a vital migratory stopover for birds that empties

  Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
• 

  

  /33

  $594,000

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

  118 Sandy Point Rd, Old Saybrook, CT 06475

  This condominium at Summerwood includes a one car garage with loft area. The garage has a separate deed and the condominium may be purchased for $544,00 not including the garage. 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

  Carla Mousch William Raveis Real Estate

  118 Sandy Point Rd, Old Saybrook, CT 06475
• 

  

  /40

  $1,795,000

  • 5 Beds
  • 2.5 Baths
  • 2,994 Sq Ft

  4 Old Fenwick Rd, Old Saybrook, CT 06475

  Waterviews!!! Extraordinary Indirect Waterfront Home Overlooking Long Island Sound! Welcome to your dream home with stunning views of the Fenwick Lighthouses! This recently renovated home boasts panoramic views from every room and is move-in ready. Situated on a unique private water-view lot, the property features a lush green lawn, landscaped gardens, and is just steps away from the beautiful

  Joel Lucas Coldwell Banker Realty

  4 Old Fenwick Rd, Old Saybrook, CT 06475
• 

  

  /33

  $1,495,000

  • 4 Beds
  • 5 Baths
  • 4,546 Sq Ft

  30 Watrous Point Rd, Old Saybrook, CT 06475

  Framed by mature landscape and extensive hardscape, welcome to this private Watrous Point country home. Find a gracious, barrel-vaulted entry and a gallery-style foyer flanked by the library. Built to entertain, a solid cherry kitchen commands an 8-burner Wolf range, two Gaggenau convection ovens, warming drawers, dual Subzeros and a dream pantry. One of two fieldstone fireplaces anchors the

  Nancy Mesham Coldwell Banker Realty

  30 Watrous Point Rd, Old Saybrook, CT 06475
• 

  

  /27

  $2,345,000

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

  125 Main St, Old Saybrook, CT 06475

  Price reduction! Great opportunity to own a mixed use property on Main Street in Old Saybrook. Established salon with long term lease on first floor. Second floor has one bedroom apartment which can easily add more bedrooms or use as office space. Third floor currently occupied by two businesses and can be converted into apartment if the need arises. Prime location near The Kate and all downtown

  Gary Marino William Raveis Real Estate

  125 Main St, Old Saybrook, CT 06475

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