Middlesex, CT Homes

• 

  $625,000 Sold Mar 20, 2025

  • 1,861 Sq Ft
  • $336/SF
  • 34 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  73 Ayers Point Rd, Old Saybrook, CT 06475

  The spacious 3 bedroom/2 bath RANCH home you've been waiting for in a great location! Flexible floor plan includes a bonus room over the garage - perfect flex space for an in-home office, possible in-law; large eat-in kitchen/dining area with french door to 18x14 deck; cozy den also with access to deck. Generous-sized living room with large bay window; remodeled bath with walk-in shower and two

  Lisa Genovali Re/Max Valley Shore

  73 Ayers Point Rd, Old Saybrook, CT 06475
• 

  Est $795,455 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  17 Pratt Rd, Old Saybrook, CT 06475

  17 Pratt Rd, Old Saybrook, CT 06475
• 

  

  /2

  $19,000 Pending

  • Land
  • 0.80 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
• 

  $610,000 Sold Mar 10, 2025

  • 1,834 Sq Ft
  • $333/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  35 Sherwood Terrace, Old Saybrook, CT 06475

  Welcome to 35 Sherwood Terrace, a charming shoreline Cape nestled in the heart of downtown Old Saybrook, CT! This delightful home perfectly combines convenience and comfort, with sidewalks leading you to the town green, Main Street, library, restaurants, schools, and the renowned "The Kate" theater. Plus, enjoy easy access to Harvey's or Town Beach for those sunny days! As you step inside, you'll

  Jennifer Gurnell William Raveis Real Estate

  35 Sherwood Terrace, Old Saybrook, CT 06475
• 

  Est $595,189 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,102 Sq Ft

  77 Chalker Beach Rd, Old Saybrook, CT 06475

  77 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  

  /36

  $1,999,500 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,365 Sq Ft

  515 Maple Ave, Old Saybrook, CT 06475

  Embrace the pinnacle of coastal serenity in this captivating waterfront home, cradled by Old Saybrook's shores with a private beach, flanked by two protective break walls and a robust seawall, ensuring the preservation of your personal slice of paradise. This tranquil haven boasts a personal mooring, ideal for seafarers. Each morning, awaken to awe-inspiring sunrises that illuminate the

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

  515 Maple Ave, Old Saybrook, CT 06475
• 

  $397,000 Sold Mar 07, 2025

  • 2,060 Sq Ft
  • $193/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  1 Connolly Dr, Old Saybrook, CT 06475

  Welcome to this charming cape-style home, perfectly situated less than a mile from Main Street. The land and home have only had one owner and have been meticulously maintained. This property offers a unique opportunity to create your dream home with some personal touches. Featuring 3 bedrooms and 2 bathrooms, the first floor includes a formal living room and dining room with hardwood floors, a

  Chloe White KW Legacy Partners

  1 Connolly Dr, Old Saybrook, CT 06475
• 

  Est $501,940 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  26 Lookout Hill Rd, Old Saybrook, CT 06475

  26 Lookout Hill Rd, Old Saybrook, CT 06475
• 

  

  /36

  $599,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,249 Sq Ft

  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
• 

  $705,000 Sold Mar 03, 2025

  • 1,070 Sq Ft
  • $659/SF
  • 16 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  28 Cypress Rd, Old Saybrook, CT 06475

  Beach Living at its finest with marsh views and no flood insurance! Just steps from a private beach in Knollwood Beach Association, this charming 2 bedroom, 1 bathroom ranch offers the perfect blend of seaside tranquility and convenient access to town amenities. Interior features include hardwood floors, a fireplace, generator hook up, and ample storage in the under-house garage. A spacious four

  Julia King William Raveis Real Estate

  28 Cypress Rd, Old Saybrook, CT 06475
• 

  Est $1,652,632 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,886 Sq Ft

  32 Fenbrook Rd, Old Saybrook, CT 06475

  32 Fenbrook Rd, Old Saybrook, CT 06475
• 

  

  /40

  $1,395,000 Under Contract

  • 5 Beds
  • 3.5 Baths
  • 3,534 Sq Ft

  8 Sharon Ln, Old Saybrook, CT 06475

  This stunning 4,400 sq ft Colonial-style home offers the perfect blend of classic charm and modern luxury, just a half mile from two town beaches. Set on a beautifully landscaped half-acre lot, it feels like new construction thanks to extensive renovations completed in recent years. Every detail has been updated: new electrical, roof, windows, doors, a 1,500-gallon septic system, whole house

  Joel Lucas Coldwell Banker Realty

  8 Sharon Ln, Old Saybrook, CT 06475
• 

  $998,120 Sold Feb 28, 2025

  • 3,046 Sq Ft
  • $328/SF
  • 101 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1979

  35 Old Boston Post Rd, Old Saybrook, CT 06475

  Welcome to 35 Old Boston Post Road --- gorgeous colonial with an accessory apartment! You've been waiting for this! Steps to Old Saybrook's vibrant Main Street, elementary and middle schools, Acton Library, the gracious main home has so much to offer besides the amazing location -- 9 rooms --all generous in size with gleaming hardwood floors throughout. The kitchen offers great space for the avid

  Lisa Genovali Re/Max Valley Shore

  35 Old Boston Post Rd, Old Saybrook, CT 06475
• 

  Est $472,504 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,225 Sq Ft

  29 Sherman St, Old Saybrook, CT 06475

  29 Sherman St, Old Saybrook, CT 06475
• 

  

  /36

  $585,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  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
• 

  $737,500 Sold Feb 24, 2025

  • 2,360 Sq Ft
  • $312/SF
  • 36 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1923

  37 Sheffield St, Old Saybrook, CT 06475

  Live in the heart of charming historic Old Saybrook center. Steps away from Main Street, The Kate Theater, farmers market, town green, library, schools, shops and restaurants. Short walk to train station with Amtrak and Shoreline East service. At the end of the street take in gorgeous harbor views at the town's kayak-friendly boat launch. This 1920's gem oozes charm, starting with its arched

  Phoebe Finch William Pitt Sotheby's Int'l

  37 Sheffield St, Old Saybrook, CT 06475
• 

  Est $1,076,729 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,688 Sq Ft

  3 Shetucket Trail, Old Saybrook, CT 06475

  3 Shetucket Trail, Old Saybrook, CT 06475
• 

  

  /39

  $549,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,185 Sq Ft

  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
• 

  $476,000 Sold Feb 19, 2025

  • 2,248 Sq Ft
  • $212/SF
  • 207 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1979

  12 Forest Glen Rd, Old Saybrook, CT 06475

  Welcome to your dream home! Nestled in the heart of an established and highly sought-after neighborhood, this charming 3-bedroom Dutch Colonial offers the perfect blend of classic elegance and modern potential. With deeded beach rights to the pristine Cornfield Point Beach, you can enjoy coastal living at its finest just steps from your front door. As you enter, you'll be greeted by a warm,

  Nick Prevost William Raveis Real Estate

  12 Forest Glen Rd, Old Saybrook, CT 06475
• 

  Est $754,309 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,700 Sq Ft

  41 Church St, Old Saybrook, CT 06475

  41 Church St, Old Saybrook, CT 06475
• 

  

  /5

  $499,000 Under Contract

  • Land
  • 1.65 Acres
  • $302,424 per Acre

  384 Middlesex Turnpike, Old Saybrook, CT 06475

  Builders and Developers Take Notice! 1.65 Acre Commercial building lot on Middlesex Turnpike in a very convenient location. Right next to multiple available Commercial and Residential building lots.

  Michael Hvizdo Coldwell Banker Realty

  384 Middlesex Turnpike, Old Saybrook, CT 06475
• 

  $1,700,000 Sold Feb 18, 2025

  • 2,256 Sq Ft
  • $754/SF
  • 17 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1994

  152 N Cove Rd, Old Saybrook, CT 06475

  Introducing a rare gem on the market - a breathtaking waterfront property located in the highly coveted North Cove area of Old Saybrook, Connecticut. This exquisite home offers beautiful views of North Cove, creating a serene and picturesque living experience. Inside you will find a beautifully designed space that maximizes the views with large windows and an open floor plan that flows seamlessly

  Tammy Tinnerello William Pitt Sotheby's Int'l

  152 N Cove Rd, Old Saybrook, CT 06475
• 

  Est $570,016 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft

  421 Main St, Old Saybrook, CT 06475

  421 Main St, Old Saybrook, CT 06475
• 

  

  /24

  $749,000 Under Contract

  • 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
• 

  $550,000 Sold Feb 18, 2025

  • 2,778 Sq Ft
  • $198/SF
  • 122 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1977

  9 Hillcrest Dr, Old Saybrook, CT 06475

  Welcome to your dream home in desirable Old Saybrook! This well loved colonial offers an airy open floor plan that seamlessly connects the living, dining and kitchen areas, ideal for both entertaining and everyday living. Cozy up in the inviting family room featuring hardwood floors and centered around a whitewashed brick fireplace - perfect for chilly evenings or relaxing! Retreat to the master

  Sharon Linder Berkshire Hathaway NE Prop.

  9 Hillcrest Dr, Old Saybrook, CT 06475
• 

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,489 Sq Ft

  406 Maple Ave, Old Saybrook, CT 06475

  406 Maple Ave, Old Saybrook, CT 06475
• 

  

  /30

  $749,000 Under Contract

  • 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
• 

  $675,000 Sold Feb 14, 2025

  • 1,470 Sq Ft
  • $459/SF
  • 68 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1976

  100 Sheffield St Unit A5, Old Saybrook, CT 06475

  Welcome to your beautiful water view oasis at "The Cove" in charming Old Saybrook. It is all about the view, the view, the view! This Town House is truly located in a serene setting with magnificent views of North Cove right from your doorstep. Step inside and you will find a spacious living area filled with natural light. The entire interior of this home was freshley painted. The living room

  Vicky Welch William Raveis Real Estate

  100 Sheffield St Unit A5, Old Saybrook, CT 06475
• 

  Est $658,053 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,352 Sq Ft

  478 Main St, Old Saybrook, CT 06475

  478 Main St, Old Saybrook, CT 06475
• 

  

  /37

  $625,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,915 Sq Ft

  3 Glen Dr, Old Saybrook, CT 06475

  Location! Location! Location! IN-TOWN Gem Awaits Your Vision! Being offered for the first time in over 50 years ... located just off Pennywise Lane, c.1960's vintage home with 3 bedrooms and one and 1/2 baths, this retro split level home presents incredible potential. Just under 2,000 sq ft, it boasts spacious vaulted living room, kitchen and dining rooms surrounding a large center fireplace. Up

  Lisa Genovali Re/Max Valley Shore

  3 Glen Dr, Old Saybrook, CT 06475
• 

  $991,000 Sold Feb 10, 2025

  • 3,031 Sq Ft
  • $327/SF
  • 8 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1952

  6 Osprey Rd, Old Saybrook, CT 06475

  Welcome to a truly unique opportunity in the desirable Knollwood Beach Association, nestled in the picturesque seaside town of Old Saybrook, this sprawling ranch features over 3000sf of finished living space on both the main& lower levels and sits on a rarely found 1/2-acre flat lot with 2-car gar, offering the perfect canvas for your vision and creativity.Whether you're seeking a year-round

  Mary Jean Agostini RE/MAX Right Choice

  6 Osprey Rd, Old Saybrook, CT 06475
• 

  Est $627,170 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  7 Buck Hill Rd, Old Saybrook, CT 06475

  7 Buck Hill Rd, Old Saybrook, CT 06475
• 

  

  /37

  $1,250,000 Under Contract

  • 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
• 

  $450,000 Sold Jan 31, 2025

  • 1,114 Sq Ft
  • $404/SF
  • 46 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1985

  18 1st Ave, Old Saybrook, CT 06475

  Panoramic Connecticut River and Tidal Marsh Views-A hidden gem tucked privately alongside the marsh where you will enjoy views of the sparkling waters of the river, wildlife, and the boats making their way on the river. This charming and bright home wins you over with sundrenched rooms and open floorplan. Perfect as year-round residence, weekend getaway, or use as an investment property. Walk to

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

  18 1st Ave, Old Saybrook, CT 06475
• 

  Est $998,447 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,444 Sq Ft

  23 Park Ave, Old Saybrook, CT 06475

  23 Park Ave, Old Saybrook, CT 06475
• 

  

  /17

  $850,000 Under Contract

  • 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
• 

  $553,000 Sold Jan 24, 2025

  • 1,008 Sq Ft
  • $549/SF
  • 55 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1958

  6 Briarwood Dr, Old Saybrook, CT 06475

  NEW CONDITIONS / Walk to beach!!! Discover the perfect coastal retreat in this beautifully updated ranch, ideal for those seeking the charm of seaside living. With 3 bedrooms and 1.5 baths, this home has been meticulously maintained and brought to new condition, featuring a new roof, windows,updated mechanicals, and central air conditioning. Situated on a level half-acre lot, the property offers

  Joel Lucas Coldwell Banker Realty

  6 Briarwood Dr, Old Saybrook, CT 06475
• 

  Est $235,428 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 880 Sq Ft

  174 Old Boston Post Rd Unit 25, Old Saybrook, CT 06475

  174 Old Boston Post Rd Unit 25, Old Saybrook, CT 06475
• 

  

  /36

  $2,850,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 4,789 Sq Ft

  372 Maple Ave, Old Saybrook, CT 06475

  Welcome to your dream home! This stunning colonial with beautiful views of Long Island Sound comes fully furnished with stylish, high-quality pieces, making it the perfect turnkey beach property. The well-equipped kitchen has granite countertops, stainless steel appliances including double Viking Ovens, SubZero fridge, large Island with breakfast bar and access to the patio. The dining room has a

  Colleen Nemec Showcase Realty, Inc.

  372 Maple Ave, Old Saybrook, CT 06475
• 

  $800,000 Sold Jan 24, 2025

  • 2,600 Sq Ft
  • $308/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  Unlisted Address

  Brand new 4 bedroom colonial nestled on a private road backing up to the preserve. Hardwood floors throughout. Central air, propane heat, on demand hot water. Private master suite with his & her closets. Open floor plan. Ready in 30 days.

  Michael Zarotney Connecticut Real Estate Properties LLC

  Unlisted Address

Showing Results 241 - 280, Page 7 of 18