Old Saybrook, CT Homes

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  /34

  $560,000 Pending

  • 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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  Explore Old Saybrook

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  /35

  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  18 Belaire Manor, Old Saybrook, CT 06475

  Check our price reduction making this a worthwhile weekend getaway! Or the every minute opportunity to spend the "off season" at the beach. Come and see this completelyRenovated to the hilt beachhouse. High ceilings, the finest of everything! This is an Academic Rental available from 9/1/25-5/31/26. It is not available for yearly rental. NOT Annual Rental. But for 9 Months come and enjoy the

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 544-5686

  18 Belaire Manor, Old Saybrook, CT 06475
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  $595,000 Sold Sep 12, 2025

  • 1,976 Sq Ft
  • $301/SF
  • 74 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1976

  6 Pheasant Hill Ln, Old Saybrook, CT 06475

  Welcome to this beautifully maintained home. Set at the end of cul-de-sac and bordered by The Preserve Connecticut's largest coastal forest, this property offers privacy and natural beauty with direct access to miles of scenic hiking trails right outside your door. Minutes to I-95, close to Old Saybrook shops, top rated schools and beaches. Enjoy an open concept kitchen formal dining room, cozy

  Letessa Dion Coldwell Banker Realty

  6 Pheasant Hill Ln, Old Saybrook, CT 06475
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  Est $519,372 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,930 Sq Ft

  175 Ferry Rd Unit 11, Old Saybrook, CT 06475

  175 Ferry Rd Unit 11, Old Saybrook, CT 06475
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  /19

  $399,900

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

  52 Chalker Beach Rd, Old Saybrook, CT 06475

  This property is located in the private Chalker Beach community. This 3 Bedroom / 1.5 Bathroom house is a short walk from the white sandy Beaches and all the fun that comes with this Beach Community. Imagine all the unforgettable moments you'll create in this incredibly desirable location! Property is being sold As Is.

  

  Patrick Farley

  Statewide Premier Prop. LLC

  (860) 718-4375

  52 Chalker Beach Rd, Old Saybrook, CT 06475
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  /27

  $2,552 - $3,198 per month

  Saybrook Station Apartments

  1 - 2 Beds

  7 N Main St, Old Saybrook, CT 06475

  Located in Old Saybrook, with easy access to Main Street and Boston Post Road, Saybrook Station Apartments are just a quick jaunt to the train station, a four-minute drive to the historic Town Green, and minutes away from 1000 acres of coastal forest at The Preserve. Not to mention, all of the shopping, dining, and entertainment that nearby New Haven has to offer. Picture coming home every day to

  7 N Main St, Old Saybrook, CT 06475
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  $625,000 Sold Sep 12, 2025

  • 1,980 Sq Ft
  • $316/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  21 Briarcliffe Trail, Old Saybrook, CT 06475

  This classic colonial offers timeless charm and is meticulously maintained, set on a beautifully landscaped lot and combines space, comfort, and outdoor enjoyment. Step inside to find a sun filled living room with a cozy fireplace, a formal dining room, inviting family room with a charming built-in bar perfect for gatherings. The sun filled kitchen features sliders that open to an expansive deck

  Sharon Linder Berkshire Hathaway NE Prop.

  21 Briarcliffe Trail, Old Saybrook, CT 06475
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  Est $647,552 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  24 Willard St, Old Saybrook, CT 06475

  24 Willard St, Old Saybrook, CT 06475
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  /40

  $450,000

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  13 College St, Old Saybrook, CT 06475

  Adorable seasonal beach cottage nestled in the heart of Old Saybrook! This charming 2-bedroom, 1 bath retreat offers the perfect blend of coastal charm and convenience. Enjoy the large deep back yard and outdoor shower after you return from a day at the beach. Connected to public water and ideally located just a short stroll to town, or the Saybrook Point Inn. Whether you're dreaming of summer

  

  Maddy Mattson

  Coldwell Banker Realty

  (860) 579-6292

  13 College St, Old Saybrook, CT 06475
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  /28

  $2,200 per month

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  31 Cottage Place, Old Saybrook, CT 06475

  Walk to town from this meticulously maintained Cape Cod home located on a dead end street. First floor has a bedroom, kitchen, laundry, dining room, large living room and 1/2 bath. Second floor has 2 large bedrooms and a full bath with hw floors throughout. Large partial basement for storage. Owner will consider pets, off street parking, private yard with fence and shed. Tenant responsible for

  Nikki Travaglino William Pitt Sotheby's Int'l

  31 Cottage Place, Old Saybrook, CT 06475
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  $3,200,000 Sold Sep 10, 2025

  • 4,435 Sq Ft
  • $722/SF
  • 20 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1986

  450 Maple Ave, Old Saybrook, CT 06475

  **Stunning Waterfront Home at Knollwood Beach** Discover unparalleled luxury in this meticulously updated prime front-row residence overlooking Long Island Sound. Floor-to-ceiling windows frame breathtaking water vistas from every room, creating an immersive coastal living experience. Recent comprehensive renovations include new HVAC systems, custom Hunter Douglas window treatments throughout,

  Teri Strain-Lewis William Pitt Sotheby's Int'l

  450 Maple Ave, Old Saybrook, CT 06475
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  Est $638,427 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  40 Bokum Rd, Old Saybrook, CT 06475

  40 Bokum Rd, Old Saybrook, CT 06475
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  /40

  $875,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft

  45 Farview Ave, Old Saybrook, CT 06475

  A Refined Coastal Estate in the Heart of Old Saybrook, Connecticut. Set on nearly an acre along a tranquil tidal inlet leading into the Ferry Point Marsh Wildlife Management Area, this coastal estate offers a rare blend of privacy, natural beauty, and enduring craftsmanship. A true retreat, where every element has been curated with care and intention. Inside, the layout is designed for effortless

  

  Amy Rubin

  RE/MAX Legends

  (860) 854-9586

  45 Farview Ave, Old Saybrook, CT 06475
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  /35

  $2,950 - $4,270 per month

  Hanford Commons

  1 - 2 Beds

  99 Lynde St, Old Saybrook, CT 06475

  Welcome to Hanford Commons – The Definition of LuxuryDiscover modern living at its finest with our brand-new apartments in the picturesque town of Old Saybrook. Hanford Commons perfectly blends style, convenience, and comfort, offering you a home that exceeds expectations. Each thoughtfully designed unit features stainless steel appliances, an in-unit washer and dryer, central heating and

  99 Lynde St, Old Saybrook, CT 06475
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  $1,427,500 Sold Sep 10, 2025

  • 1,680 Sq Ft
  • $850/SF
  • 54 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  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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  Est $744,774 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,502 Sq Ft

  456 Main St, Old Saybrook, CT 06475

  456 Main St, Old Saybrook, CT 06475
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  /23

  $699,500 Under Contract

  • Land
  • 8.11 Acres
  • $86,252 per Acre

  60 Ingham Hill Rd, Old Saybrook, CT 06475

  Picturesque waterfront 8.1-acre lot on the tranquil Oyster River in historic Old Saybrook. 1,400 feet of river frontage leading to Long Island Sound. Currently set as farmland, this could be a home run for builders sensitive to the needs of the land. With its beauty, you have 50-plus feet of road frontage and large footprint within the 50-foot tidal wetlands setback. I-95 is easily accessible,

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 735-1229

  60 Ingham Hill Rd, Old Saybrook, CT 06475
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  /14

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • House for Rent

  Unlisted Address

  Welcome to this charming ranch-style home in the desirable North Cove neighborhood of Old Saybrook. Conveniently located near the shoreline, Main Street, shops, restaurants, and the Saybrook Point Resort & Marina, this property offers both comfort and accessibility. The home features a bright living area, in-unit washer and dryer, and comes fully furnished for added convenience. Enjoy

  Timothy Johnson LPT Realty

  Unlisted Address
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  $850,000 Sold Sep 08, 2025

  • 3,200 Sq Ft
  • $266/SF
  • 77 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  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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  Est $1,648,544 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,580 Sq Ft

  23 Red Bird Trail, Old Saybrook, CT 06475

  23 Red Bird Trail, Old Saybrook, CT 06475
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  /40

  $529,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  25 King St, Old Saybrook, CT 06475

  NEW to the market in Old Saybrook is this Like-New Ranch within minimal walking distance to Main Street! This home is meticulously cared for with many desirable (recent) upgrades. Gleaming hardwood floors throughout the entire main level, a spotless kitchen featuring Granite countertops and a generously sized island for gathering, newer appliances, custom cabinetry, and a dining room that was a

  Joe Loguidice William Raveis Real Estate

  25 King St, Old Saybrook, CT 06475
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  /51

  $3,250 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  5 Tudor Ct W, Old Saybrook, CT 06475

  A rare year round rental in beautiful Old Saybrook! Freshly Painted Home with new appliances, new heating system and new roof. Close to the Beach with Beach rights. 2 large Decks off Living room Kitchen and Master Bedroom.Walk in closet for Master Bedroom. Large Carport.2 Full size Bathrooms upstairs and downstairs. Master Bedroom and 2nd bedroom upstairs. Large bedroom downstairs. Family

  5 Tudor Ct W, Old Saybrook, CT 06475
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  $410,000 Sold Sep 05, 2025

  • 504 Sq Ft
  • $813/SF
  • 41 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1950

  49 Hartford Ave, Old Saybrook, CT 06475

  Welcome to your seaside escape! This cozy beach cottage sits on a rare double lot, offering abundant parking, a detached garage, and possibilities! The living area, kitchen and bedroom have hardwood floors and coastal charm! A short stroll down to the private beach association of Saybrook Manor. Whether you are seeking a year-round home or a seasonal getaway, the house/double lot offers

  Sharon Linder Berkshire Hathaway NE Prop.

  49 Hartford Ave, Old Saybrook, CT 06475
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  Est $6,701,707 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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  /39

  $1,398,989

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

  26 Meadowood Ln, Old Saybrook, CT 06475

  No Flood Insurance Required! Imagine mornings filled with sunlight streaming across red oak floors, evenings spent entertaining from a chef's kitchen, and endless days enjoying water views ~ this is life at 26 Meadowood Lane. Built in 2025, this custom Colonial offers the rarest of combinations: architectural elegance, modern comfort, and a prime Old Saybrook location just minutes from beaches,

  Jennifer Gurnell William Raveis Real Estate

  26 Meadowood Ln, Old Saybrook, CT 06475
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  /36

  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 1,120 Sq Ft
  • House for Rent

  8 Belaire Manor, Old Saybrook, CT 06475

  {Summer 2026 - June, July, Aug, Sept} This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the beach is perfect for

  Erika Raffles William Pitt Sotheby's Int'l

  8 Belaire Manor, Old Saybrook, CT 06475
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  $625,000 Sold Sep 03, 2025

  • 1,249 Sq Ft
  • $500/SF
  • 47 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1940

  19 Hartford Ave, Old Saybrook, CT 06475

  Step into coastal serenity at this fully updated Saybrook Manor Cape style home-just a short, leisurely walk from three private beaches. Gleaming hardwood floors span the open concept main level living, flowing effortlessly from a bright foyer into the living room and kitchen, featuring granite countertops, custom builtins, and pantry space. A cozy sitting area by the foyer adds charm, while the

  Frank Fonteyn Prestige Realty Group

  19 Hartford Ave, Old Saybrook, CT 06475
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  Est $421,765 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  310 Springbrook Rd, Old Saybrook, CT 06475

  310 Springbrook Rd, Old Saybrook, CT 06475
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  /40

  $1,249,000

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft

  25 Maplewood Rd, Old Saybrook, CT 06475

  Knollwood Beach Association NEW Construction! Experience three levels of sun-filled coastal elegance in this tastefully designed home offering space and flexibility for modern living. The open floor plan flows with light-colored hardwoods throughout, anchored by a designer white kitchen on the main level, while a walk-out lower level with its own kitchenette provides the perfect setting for

  Joel Lucas Coldwell Banker Realty

  25 Maplewood Rd, Old Saybrook, CT 06475
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  /22

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  4 Old Colony Rd, Old Saybrook, CT 06475

  Cornfield Point Beach area, October 15th 2025-May 15 2026. Furnished. Academic Rental.Conveniently located near town, restaurants and train station. You will fall in love with this Old Saybrook 3 bedroom, 2 full bathroom home. Newly renovated. Fully furnished, move in ready. Washer and dryer in basement. Open concept kitchen with stainless steel appliances, dishwasher, microwave, hardwood

  4 Old Colony Rd, Old Saybrook, CT 06475
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  $705,000 Sold Aug 29, 2025

  • 2,469 Sq Ft
  • $286/SF
  • 14 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  11 Obed Heights, Old Saybrook, CT 06475

  This charming colonial home is beautifully set back from the street on a serene 1.05-acre lot, offering plenty of privacy. The large kitchen has granite countertops and stainless-steel appliances, making it a perfect space for cooking and entertaining. Adjacent to the kitchen is a lovely dining area and a spacious living room, ideal for gatherings. The cozy den, complete with a fireplace, opens

  Kelly D'Anna Statewide Premier Prop. LLC

  11 Obed Heights, Old Saybrook, CT 06475
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  Est $771,128 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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  /22

  $1,190,000

  • 1 Bed
  • 1 Bath
  • 578 Sq Ft

  174 Nehantic Trail, Old Saybrook, CT 06475

  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

  Joel Lucas Coldwell Banker Realty

  174 Nehantic Trail, Old Saybrook, CT 06475
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  /23

  $3,000 per month

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

  8 Clinton Ave, Old Saybrook, CT 06475

  Turn-key Academic Shoreline Rental with 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

  Terry McDonald McDonald Real Estate, LLC

  8 Clinton Ave, Old Saybrook, CT 06475
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  $539,000 Sold Aug 27, 2025

  • 1,185 Sq Ft
  • $455/SF
  • 43 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1947

  18 Lynde St, Old Saybrook, CT 06475

  18 Lynde St is a classic cape style home, where vintage charm meets coastal living in the heart of downtown Old Saybrook. This home has timeless appeal with its original wood doors and classic glass doorknobs of the 1940's. Intimate in size, the space is inviting and brimming with potential, including the possibility of expansion. Less than a mile's walk to North Cove with access to the CT River,

  Liz Squillacote William Pitt Sotheby's Int'l

  18 Lynde St, Old Saybrook, CT 06475
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  Est $663,665 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,813 Sq Ft

  5 Crowley Dr, Old Saybrook, CT 06475

  5 Crowley Dr, Old Saybrook, CT 06475
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  /39

  $799,900

  • 2 Beds
  • 1.5 Baths
  • 1,950 Sq Ft

  16 Seagull Rd, Old Saybrook, CT 06475

  Thoughtfully Enhanced Old Saybrook Retreat Steps from Knollwood Beach! This meticulously improved 1,868 square foot home in desirable Old Saybrook offers the perfect blend of modern convenience and coastal lifestyle. Significant updates throughout include a new furnace, central air conditioning, whole-house generator, new propane tank, and complete 200 amp electrical service upgrade, ensuring

  Teri Strain-Lewis William Pitt Sotheby's Int'l

  16 Seagull Rd, Old Saybrook, CT 06475
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  /33

  $2,950 per month

  • 3 Beds
  • 2 Baths
  • 1,962 Sq Ft
  • House for Rent

  56 Hartford Ave, Old Saybrook, CT 06475

  Annual Entire house and garage with waterviews and beach steps away! You will love the large yard for gardening and waterviews! The home has a great open flow first floor with a large 4 season room great for entertaining. The 3 bedrooms are large and 2 full bathrooms. Can come furnished or unfurnished. A small pet maybe considered with owner approval and extra pet security. Tenant pays all

  Joel Lucas Coldwell Banker Realty

  56 Hartford Ave, Old Saybrook, CT 06475
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  $800,000 Sold Aug 20, 2025

  • 2,297 Sq Ft
  • $348/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  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

  12 4th Ave, Old Saybrook, CT 06475
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  Est $591,727 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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