Old Saybrook, CT Homes

• 

  

  

  /40

  $1,095,000

  • 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
• 

  

  

  /40

  $40,000 per month

  • 4 Beds
  • 3 Baths
  • 3,762 Sq Ft
  • House for Rent

  17 Agawam Ave, Old Saybrook, CT 06475

  Fantastic Opportunity to Rent for the month of July in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage offers Fenwick's unique lifestyle: beach, tennis courts, yacht club and famed golf course. Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with

  Lynn Lehrman Re/Max Valley Shore

  17 Agawam Ave, Old Saybrook, CT 06475
• 

  $520,000 Sold May 16, 2025

  • 1,225 Sq Ft
  • $424/SF
  • 44 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1955

  25 Sherman St, Old Saybrook, CT 06475

  Ideally situated just a short walk from Main Street and moments from the shoreline, this home offers coastal charm and fully renovated comfort. This sun-filled 3-bedroom ranch, delivers the ease of one-level living with a modern, designer touch throughout.The welcoming great room features a cozy fireplace and flows effortlessly into a eat-in kitchen. Outfitted with white shaker cabinetry,

  Ginny Proft William Raveis Real Estate

  25 Sherman St, Old Saybrook, CT 06475
• 

  Est $625,792 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  34 Coulter St, Old Saybrook, CT 06475

  34 Coulter St, Old Saybrook, CT 06475
• 

  

  

  /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
• 

  

  /21

  $2,400 per month

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • House for Rent

  116 Chalker Beach Rd, Old Saybrook, CT 06475

  Gorgeous Academic Rental Home at Chalker Beach, 2 bedrooms with Queen Beds, 3rd bedroom is currently used as an office and workout space. Offering vinyl plank flooring, with an open living concept; living room with LP gas fireplace, kitchen and sun porch! Gorgeous updated kitchen, stainless steel appliances, beautiful butcher block counters all with an updated bathroom along with a washer and

  Terry McDonald McDonald Real Estate, LLC

  116 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  $993,500 Sold May 16, 2025

  • 1,648 Sq Ft
  • $603/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  11 Beach Rd E, Old Saybrook, CT 06475

  Stunning Water Views! Welcome to 11 Beach Road East, Chalker Beach! This meticulously maintained, year-round home offers breathtaking water views of Long Island Sound from the front, while the back showcases a tranquil view of Hager Creek. With a prime location in the desirable Chalker Beach community, this property is a rare find! Inside, you'll find a spacious master bedroom with panoramic

  Kristin Davis Berkshire Hathaway NE Prop.

  11 Beach Rd E, Old Saybrook, CT 06475
• 

  Est $109,953 Not Listed For Sale

  22 Ragged Rock Rd, Old Saybrook, CT 06475

  22 Ragged Rock Rd, Old Saybrook, CT 06475
• 

  

  /33

  $1,150,000

  • 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
• 

  

  /16

  $3,000 per month

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

  1 Cedarwood Ln, Old Saybrook, CT 06475

  Beautifully redone ranch in the sought after Cornfield Point neighborhood on a fantastic corner lot. Completely renovated kitchen with ceramic floors, refurbished cabinets, and fresh paint throughout. 3 Bedrooms, two full baths and a large finished basement this property also comes with a 1 car attached garage. Enjoy the private beach association of the Cornfield Point Association while still

  Jack Pandolfe Coldwell Banker Realty

  1 Cedarwood Ln, Old Saybrook, CT 06475
• 

  $650,000 Sold May 15, 2025

  • 1,260 Sq Ft
  • $516/SF
  • 33 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1953

  37 Fenwood Rd, Old Saybrook, CT 06475

  FIRST TIME OFFERED FOR SALE! Fenwood District Association with beach access and the historic Fenwick Golf Club nearby. This home offers one floor living, on a level lot, in a sought after area of Old Saybrook. Beautiful hardwood floor (just refinished) throughout, eat-in kitchen, 3 bedrooms, and a finished room in the lower level with built-ins. The rear deck is perfect for outdoor grilling, and

  Chuck Conti Coldwell Banker Realty

  37 Fenwood Rd, Old Saybrook, CT 06475
• 

  Est $553,228 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  407 Main St, Old Saybrook, CT 06475

  407 Main St, Old Saybrook, CT 06475
• 

  

  /40

  $1,299,000

  • 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
• 

  

  /22

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • House for Rent

  28 Beach Rd W, Old Saybrook, CT 06475

  Amazing views every day at 28 Beach Rd West, Old Saybrook! This beautiful Academic Rental beach home has 3 bedrooms and 2 baths and is available for your enjoyment ... across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

  Terry McDonald McDonald Real Estate, LLC

  28 Beach Rd W, Old Saybrook, CT 06475
• 

  $575,000 Sold May 15, 2025

  • 1,898 Sq Ft
  • $303/SF
  • 57 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

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

  Nestled along the beautiful Long Island Sound, this condo offers an idyllic setting with two bedrooms and two bathrooms with private beach, pickleball courts, tennis courts, and a pool. It's a perfect spot for enjoying both relaxation and outdoor activities. The first floor provides a spacious, inviting living room with wood floors and a charming fireplace that adds a cozy touch to the

  Carla Mousch William Raveis Real Estate

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

  Est $367,637 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  15 Cranton Ave, Old Saybrook, CT 06475

  15 Cranton Ave, Old Saybrook, CT 06475
• 

  

  /23

  $849,000

  • 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
• 

  

  /25

  $6,000 per month

  • 5 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • House for Rent

  1200 Boston Post Rd, Old Saybrook, CT 06475

  october- may!!!!!The historic Nathaniel Clark House in Old Saybrook, Connecticut, has a taste of New England charm. Large families or people who require additional space to work from home will love this roomy five-bedroom house. Savor a tranquil setting for your winter getaway with warm fires, a spacious porch, a lovely garden, and a quiet greenhouse. This house is perfect for family

  Marina Kokis William Raveis Real Estate

  1200 Boston Post Rd, Old Saybrook, CT 06475
• 

  $840,000 Sold May 15, 2025

  • 2,380 Sq Ft
  • $353/SF
  • 2 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1961

  41 Meadowood Ln, Old Saybrook, CT 06475

  EXPANDED COLONIAL in the desirable Meadowood neighborhood is close to restaurants, boutiques, & beaches. The main level features hardwood floors, a spacious living room w/fireplace insert, & 1/2 bath. The kitchen has granite countertops & is complemented by a breeze way & 3-season sunroom adding nearly 200 sq. ft. living space. The 2nd fl has a full bath, 4 bdrms & new laundry room. The

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

  41 Meadowood Ln, Old Saybrook, CT 06475
• 

  Est $552,757 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,288 Sq Ft

  136 Sandy Point Rd, Old Saybrook, CT 06475

  136 Sandy Point Rd, Old Saybrook, CT 06475
• 

  

  /40

  $899,900

  • 3 Beds
  • 3 Baths
  • 2,261 Sq Ft

  10 Cottage Ave, Old Saybrook, CT 06475

  Welcome to Bel Aire Manor Private Beach Association, where coastal living at its finest awaits you. Nestled within this idyllic sanctuary, this family residence is one of only 19 dwellings. As you approach the residence, you will observe the wrap-around front porch, an ideal spot to unwind and appreciate the picturesque beauty of the Connecticut shoreline. Keep an eye out for the majestic Osprey

  Joe Scarpellino Coldwell Banker Realty

  10 Cottage Ave, Old Saybrook, CT 06475
• 

  

  /20

  $2,600 per month

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • House for Rent

  163 Ferry Rd, Old Saybrook, CT 06475

  Completely renovated! Upstairs Ranch-Style unit offers a rare opportunity for waterfront living, with views of the Ferry Landing Marina, Connecticut River, and Long Island Sound. Located directly across from the marina. This 2-bedroom, 1-bathroom home combines modern updates with an unbeatable location for boating, fishing, and outdoor enjoyment. The open-concept newly remodeled kitchen, cooking

  David Boudinot Berkshire Hathaway NE Prop.

  163 Ferry Rd, Old Saybrook, CT 06475
• 

  $805,000 Sold May 12, 2025

  • 1,531 Sq Ft
  • $526/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  57 Atlantic Dr, Old Saybrook, CT 06475

  Welcome to your dream coastal retreat in Knollwood Beach! This beautifully updated Cape Cod-style home is perfect for those looking for a peaceful second home or a comfortable place to enjoy retirement. Step inside and discover a bright, airy space with a brand-new white kitchen that opens to the family room and dining area, creating the perfect spot for entertaining or simply relaxing. A formal

  Joel Lucas Coldwell Banker Realty

  57 Atlantic Dr, Old Saybrook, CT 06475
• 

  Est $600,390 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,352 Sq Ft

  44 Middletown Ave, Old Saybrook, CT 06475

  44 Middletown Ave, Old Saybrook, CT 06475
• 

  

  /39

  $925,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 4,559 Sq Ft

  134 School House Rd, Old Saybrook, CT 06475

  A private estate minutes from the shore-welcome to 134 School House Road. Tucked away on a beautiful 3.4 acres, this 4,500 sq ft custom Colonial offers timeless elegance and unparalleled privacy in one of Old Saybrook's most coveted locations. A winding driveway leads you to a stately residence surrounded by nature. Inside, hardwood floors, three fireplaces, and formal living and dining spaces

  Tina Rupp William Pitt Sotheby's Int'l

  134 School House Rd, Old Saybrook, CT 06475
• 

  

  /23

  $75,000 per month

  • 9 Beds
  • 6 Baths
  • 5,413 Sq Ft
  • House for Rent

  21 Pettipaug Ave, Old Saybrook, CT 06475

  Embrace the Quintessence of Summer Living at the Historic Fenwick Cottage ~ Nestled in the heart of the Borough of Fenwick, this iconic Victorian waterfront cottage presents a rare opportunity to experience summer as it was meant to be. With its shingled exterior and timeless charm, the Fenwick Cottage is an idyllic retreat for the discerning summer resident. This shingled historic cottage boasts

  Colette Harron William Pitt Sotheby's Int'l

  21 Pettipaug Ave, Old Saybrook, CT 06475
• 

  $895,000 Sold May 12, 2025

  • 1,910 Sq Ft
  • $469/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  75 Fenwood Dr, Old Saybrook, CT 06475

  Discover this enchanting Cape Cod-style residence located in the coveted Fenwood neighborhood of Old Saybrook, a peaceful community just moments from the beach that is a favorite with cyclists and walkers. This delightful home is a serene oasis with soothing views of the natural marshland. It boasts three inviting bedrooms bathed in sunlight; the first-floor bedroom is just steps from a full

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

  75 Fenwood Dr, Old Saybrook, CT 06475
• 

  Est $416,079 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  7 North St, Old Saybrook, CT 06475

  7 North St, Old Saybrook, CT 06475
• 

  

  /24

  $749,000

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft

  509 Main St Unit 6, Old Saybrook, CT 06475

  Charming Colonial with water views - Location & Lifestyle! Fall in love with this beautifully maintained colonial offering scenic water views in an unbeatable location between north and south cove! Just minutes from town, top-rated schools, popular restaurants, beaches, and public transportation, this home blends convince with classic charm. Featuring 3 spacious bedrooms, 2.5 baths, a welcoming

  Jake Pulcini Chiarito Real Estate LLC

  509 Main St Unit 6, Old Saybrook, CT 06475
• 

  

  /29

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,972 Sq Ft
  • House for Rent

  2 Point Rd, Old Saybrook, CT 06475

  The Iconic 2 Point Road Old Saybrook. Enjoy the breathtaking water views from every room! There are two full suites on the main level. The primary suite with French doors opening to its own balcony with breathtaking panoramic views will leave you speechless. The outside grounds boasts stunning views of Long Island Sound, Orient Point, Plum Island and more. Cornfield Point Association allows

  David Rodriguez William Pitt Sotheby's Int'l

  2 Point Rd, Old Saybrook, CT 06475
• 

  $725,000 Sold May 12, 2025

  • 2,448 Sq Ft
  • $296/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1997

  8 Acorn Dr, Old Saybrook, CT 06475

  Discover the perfect blend of charm, comfort, and convenience in this stunning 4-bedroom Colonial, perched atop a peaceful hill at the end of a private road. Located in a highly desirable school district, this home offers a bright, open floor plan with hardwood floors throughout-ideal for family living and entertaining. At the heart of the home, the beautifully remodeled kitchen features two

  Craig Milton Re/Max Valley Shore

  8 Acorn Dr, Old Saybrook, CT 06475
• 

  Est $430,470 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 910 Sq Ft

  29 Whitewood St, Old Saybrook, CT 06475

  29 Whitewood St, Old Saybrook, CT 06475
• 

  

  /30

  $749,000

  • 3 Beds
  • 1.5 Baths
  • 2,194 Sq Ft

  355 Main St, Old Saybrook, CT 06475

  In the heart of Old Saybrook! This home was built in 1919 and is called a New Englander. This is the perfect location to walk to town for dining or entertainment. The Kate is a wonderful place for many exciting events. Our town green offers concerts on weekday nites in the summer for enjoyment. Old Saybrook is the hub to Harford and New Haven. Easy access to all major routes. The town is an

  Paula Stuart Berkshire Hathaway NE Prop.

  355 Main St, Old Saybrook, CT 06475
• 

  

  /40

  $6,500 per month

  • 5 Beds
  • 4 Baths
  • 3,154 Sq Ft
  • House for Rent

  3 Wilson Ave, Old Saybrook, CT 06475

  Academic Rental in desirable Fenwick! Available from September 2024 through May 2025 at 4,000 per month; and available from September 2025 through May 2026 at $6,500 per month ~ we are looking for tenants for full academic term. This exceptional property offers the ultimate in Shoreline living. Set privately on a knoll overlooking open marshlands to water views of Long Island Sound and the outer

  Lynn Lehrman Re/Max Valley Shore

  3 Wilson Ave, Old Saybrook, CT 06475
• 

  $699,000 Sold May 09, 2025

  • 980 Sq Ft
  • $713/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1961

  87 Chalker Beach Rd, Old Saybrook, CT 06475

  Welcome to this beautifully updated coastal retreat in the Chalker Beach Association, offering year-round comfort and effortless beachside living. Thoughtfully renovated from top to bottom, this charming home features a light-filled kitchen with granite countertops, a gas cooktop, and bar seating, flowing into a spacious living room with a gas fireplace, built-in shelving, and a bright dining

  Jason Lafleur William Pitt Sotheby's Int'l

  87 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  Est $518,653 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,107 Sq Ft

  20 Whitney Ave, Old Saybrook, CT 06475

  20 Whitney Ave, Old Saybrook, CT 06475
• 

  

  /40

  $779,000

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  8 Edwards Rd, Old Saybrook, CT 06475

  Your perfect beachside retreat awaits in the desirable Cornfield Point Beach community, offering deeded beach rights and a fully renovated, move-in-ready home. Ideal for retirement, a second home, or year-round living, this charming ranch sits on a professionally landscaped .20-acre lot with a fenced backyard, paved driveway, carport garage, and large shed. Relax on the welcoming rear patio,

  Joel Lucas Coldwell Banker Realty

  8 Edwards Rd, Old Saybrook, CT 06475
• 

  

  /39

  $4,750 per month

  • 3 Beds
  • 3.5 Baths
  • 1,710 Sq Ft
  • House for Rent

  8 Nibang Ave, Old Saybrook, CT 06475

  Direct waterfront in fabulous Fenwick! Academic Rental available from September 4, 2024 to May 28, 2025 at $4,000 per month and again from September 2025 to May, 2026 at $6,000 per month. Spectacular setting on South Cove. Enjoy beautiful sunrises and sunsets in this idyllic water front home in the Borough of Fenwick. Completely renovated in 2007, open floor plan kitchen, great room and dining

  Lynn Lehrman Re/Max Valley Shore

  8 Nibang Ave, Old Saybrook, CT 06475
• 

  $610,000 Sold May 09, 2025

  • 925 Sq Ft
  • $659/SF
  • 21 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1956

  11 George Dr, Old Saybrook, CT 06475

  Nicely updated ranch home with deeded beach rights to desirable Cornfield Point beach and a short walk or bike ride to Old Saybrook town beach. This sought after location has long been well known for it's walkability to the scenic Saybrook Loop, beaches and the great salt marsh. Recent improvements including a newer kitchen, full basement and an attached garage complete the package! More pictures

  Rick Allen William Raveis Real Estate

  11 George Dr, Old Saybrook, CT 06475
• 

  Est $1,136,612 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,278 Sq Ft

  300 Cromwell Ct N, Old Saybrook, CT 06475

  300 Cromwell Ct N, Old Saybrook, CT 06475

Showing Results 41 - 80, Page 2 of 18