Middlesex, CT Homes

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  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,662 Sq Ft

  6 Trolley Crossing, Old Saybrook, CT 06475

  Love to entertain, or just spend time relaxing in your extensive living areas, including the newly added inground pool with deck and patio surround? Check out the spacious front to back living room with fireplace, formal dining room, open concept great room with a renovated kitchen and family room with fireplace, and a stunning sunroom with a cathedral ceiling and brand new skylights. The kitchen

  Donald Holland William Pitt Sotheby's Int'l

  6 Trolley Crossing, Old Saybrook, CT 06475
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  /26

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,139 Sq Ft
  • House for Rent

  54 Hartford Ave, Old Saybrook, CT 06475

  Immaculate home at the beach available for rent October 1, 2025 - May 15, 2026 (negotiable). Spacious ranch with an open living, dining, and kitchen. The primary bedroom has access to the backyard and is next to the full bathroom which has a walk in shower and washer/dryer. On the other side of the home you will find 2 generous sized bedrooms and a full bathroom with bath/tub combo. Central air.

  Kate Lombardi Coccomo Real Estate LLC

  54 Hartford Ave, Old Saybrook, CT 06475
• 

  $410,000 Sold Jul 15, 2025

  • 826 Sq Ft
  • $496/SF
  • 111 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  6 West St, Old Saybrook, CT 06475

  It is all about location! Discover this cozy ranch within walking distance to Saybrook Point and Main Street to enjoy walks to restaurants, mini golf, golfing, shops and the Katherine Hephburn Cultural arts center. This home features a brand new roof, whole house generator, stainless steel appliances, new sump pump, updated bathroom, inviting stone fireplace adding warmth and character, new barn

  Sharon Linder Berkshire Hathaway NE Prop.

  6 West St, Old Saybrook, CT 06475
• 

  Est $655,364 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
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  /40

  $975,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  23 Briarwood Dr, Old Saybrook, CT 06475

  Mid-Century Modern Gem with Marsh Views and sunsets in Cornfield Point. Welcome to this stunning mid-century modern split-level home, perfectly situated on a serene half-acre lot in the sought-after Cornfield Point waterfront community. Backing directly to the marsh with water access to Long Island Sound, this beautifully updated home offers the ideal blend of timeless architectural style and

  Marc Delise Coldwell Banker Realty

  23 Briarwood Dr, Old Saybrook, CT 06475
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  /12

  $9,500 per month

  • 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
• 

  $390,000 Sold Jul 11, 2025

  • 1,557 Sq Ft
  • $250/SF
  • 93 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1977

  254 Hidden Cove Rd, Old Saybrook, CT 06475

  INVESTORS take notice! New floors and some paint and you may have yourself a great return on investment.Nestled in the picturesque town of Old Saybrook, this two bedroom, one and a half bath townhouse provides a blend of comfort and leisure. Spanning 1,557sf of thoughtfully designed living space, this residence is perfect for those seeking a tranquil lifestyle by the shore. A community swimming

  Bonnie Foster William Pitt Sotheby's Int'l

  254 Hidden Cove Rd, Old Saybrook, CT 06475
• 

  Est $158,501 Not Listed For Sale

  22 Ragged Rock Rd, Old Saybrook, CT 06475

  22 Ragged Rock Rd, Old Saybrook, CT 06475
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  /40

  $1,000,000

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  7 Sharon Ln, Old Saybrook, CT 06475

  Welcome to 7 Sharon Lane, a classic Colonial on 1.35 acres, set against the tranquil backdrop of the Back River conservation marsh and located minutes from two town beaches. This inviting 4-bedroom, 2.5-bath, spacious home offers the perfect blend of formal entertaining, daily convenience and coastal lifestyle. Inside, the main entry foyer gives access to an open and welcoming floor plan; a

  Sara Venditto William Pitt Sotheby's Int'l

  7 Sharon Ln, Old Saybrook, CT 06475
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  /26

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 1,356 Sq Ft
  • House for Rent

  94 Nehantic Trail, Old Saybrook, CT 06475

  Welcome to the popular Indian Town Beach Association in Old Saybrook. This is a fully furnished academic rental available from September 15, 2025, to May 15, 2026. Bright and neat, this home has been well taken care of both inside and out. The home features central air, propane heat, 2 bedrooms, a living room, a generously sized eat-in kitchen, a full set of laundry on the main floor, and a full

  Sang Jee William Raveis Real Estate

  94 Nehantic Trail, Old Saybrook, CT 06475
• 

  $550,000 Sold Jul 10, 2025

  • 1,636 Sq Ft
  • $336/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  64 Obed Heights, Old Saybrook, CT 06475

  This is the house that you have been waiting for! Welcome to 64 Obed Heights, a fabulous 3-bedroom, 2-bathroom ranch in the beautiful shoreline town of Old Saybrook. This house has so many features and updates that make it the perfect place to be your new home. The kitchen was fully redone in 2019, the oil tank was replaced in 2020, and the bulkheads were just installed a few weeks ago. The

  Joshua Young Berkshire Hathaway NE Prop.

  64 Obed Heights, Old Saybrook, CT 06475
• 

  Est $967,599 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,178 Sq Ft

  11 Fenwood Ave, Old Saybrook, CT 06475

  11 Fenwood Ave, Old Saybrook, CT 06475
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  /37

  $1,475,000

  • 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
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  /32

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 1,665 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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  $505,000 Sold Jul 07, 2025

  • 1,557 Sq Ft
  • $324/SF
  • 101 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475

  NEW PRICE!! Owners say "SELL"!! You can't miss this.... Newly remodeled home at an amazing new price!!!! COME SEE .... A wonderful transformation has been made ...Two New baths! New quartz kitchen counters, new HARDWOOD floors installed on first floor, new carpeting and tile; even the "popcorn" ceilings are gone! Freshly painted, this home is waiting for its new owners! WELCOME to Summer Wood

  Lisa Genovali Re/Max Valley Shore

  104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
• 

  Est $601,423 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
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  /36

  $925,000 Open Sun 11AM - 1PM

  • 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
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  /35

  $5,500 per month

  • 1 Bed
  • 1 Bath
  • 1,133 Sq Ft
  • Apartment for Rent

  18 Riverside Ave, Old Saybrook, CT 06475

  Welcome to "The Boathouse", available as an annual rental! Situated on the West bank of the Connecticut River at a "boat-ique" boatyard on Ferry Point, this 2016 custom built, fully finished Nantucket style 1 bedroom luxury apartment which perfectly captures views of Long Island Sound. Enter through a custom mahogany door into a mudroom w/ heated floors, custom bench and spacious coat closet. Be

  Jessica Blancato William Pitt Sotheby's Int'l

  18 Riverside Ave, Old Saybrook, CT 06475
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  $520,000 Sold Jul 07, 2025

  • 922 Sq Ft
  • $564/SF
  • 122 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  25 Chalker Beach Rd, Old Saybrook, CT 06475

  Cute and Compact! This delightful cape is snuggled back from the street on a half-acre lot of serene comfort and convenience. A perfect starter home, downsizer, city retreat or condo alternative. Built in 1986 with approximately 1144 square feet, (HOUSEMEASURES 768 FIRST FLOOR & 376 SECOND FLOOR - TOTAL 1144 SQ FT). Two bedrooms, 2 full bathrooms, a two-car garage and storage shed with power.

  Susan Malton Coldwell Banker Realty

  25 Chalker Beach Rd, Old Saybrook, CT 06475
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  Est $393,041 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
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  /40

  $985,000

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  24 Cottage Place, Old Saybrook, CT 06475

  Welcome to 24 Cottage Place - a luxury shoreline home offering the perfect blend of elegance, comfort, and an unbeatable Old Saybrook location. Tucked away on a quiet dead-end street, this move-in ready 4-bedroom, 3-bath residence is just minutes from Old Saybrook's vibrant Main Street, "The Kate" theater, library, fitness center, marinas, and train station. Walk or bike to popular beaches, the

  Jennifer Gurnell William Raveis Real Estate

  24 Cottage Place, Old Saybrook, CT 06475
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  /14

  $3,180 per month

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft
  • Apartment for Rent

  109 Lynde St Unit 1, 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 1, Old Saybrook, CT 06475
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  $215,000 Sold Jul 03, 2025

  • 880 Sq Ft
  • $244/SF
  • 9 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1979

  174 Old Boston Post Rd Unit 10, Old Saybrook, CT 06475

  Discover this quaint unit at Saybrook Village Condominiums! Set in the "B" building with just four units, your humble abode awaits. With just under 900 square feet, enjoy a spacious living room featuring a wood-burning fireplace, a galley kitchen, and a comfortably sized bedroom and bathroom. Additional features include a washer/dryer, balcony, assigned parking, and a personal storage unit in the

  Kayla Chasse Compass Connecticut, LLC

  174 Old Boston Post Rd Unit 10, Old Saybrook, CT 06475
• 

  Est $563,934 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
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  /40

  $1,199,000

  • 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
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  /29

  $20,000 per month

  • 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.Weekly or monthly rental available. Cozy living-room with stunning Ocean views and entertainment areas. This home boast an upper deck where you can enjoy water

  David Rodriguez William Pitt Sotheby's Int'l

  24 W Shore Dr, Old Saybrook, CT 06475
• 

  $885,000 Sold Jul 01, 2025

  • 2,843 Sq Ft
  • $311/SF
  • 16 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1974

  4 Ridgewood Dr, Old Saybrook, CT 06475

  This meticulously maintained home welcomes you with warm pine floors, chef's kitchen with granite countertops, expansive island and gas stove top with a seamless flow to the family room with cozy fireplace, cathedral ceilings, French doors to beautiful patio and dining room with breakfast bar. Fully renovated primary bedroom suite on the first floor featuring dual walk-in closets, bathroom with

  Sharon Linder Berkshire Hathaway NE Prop.

  4 Ridgewood Dr, Old Saybrook, CT 06475
• 

  Est $597,399 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
• 

  

  /26

  $998,868

  • 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

  $3,600 per month

  • 4 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • House for Rent

  13 Billow Rd, Old Saybrook, CT 06475

  Cornfield Point rental. Available 10/1/25-5/31/26 ($3600 per month, utilities included). Relax and enjoy seaside living at its finest. Walk or bike the neighborhood while you enjoy water views from inside the house and upper deck. The interior of the home is updated, comfortable and nicely appointed. The home has central air and just two blocks to the private Cornfield Point beach. Across the

  Marc Delise Coldwell Banker Realty

  13 Billow Rd, Old Saybrook, CT 06475
• 

  $1,625,000 Sold Jul 01, 2025

  • 3,556 Sq Ft
  • $457/SF
  • 105 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  9 Overlook Dr, Old Saybrook, CT 06475

  Welcome to your dream home! Nestled on a private, gated 1.36-acre lot, this magnificent recently completed Coastal-Inspired home blends coastal charm with New England elegance. Featuring 4 bedrooms and 4.5 baths, this home is designed for both luxury and comfort. The secluded primary suite on the main level offers an expansive walk-in closet and a spa-like bathroom with a large shower, a

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  9 Overlook Dr, Old Saybrook, CT 06475
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  Est $437,438 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
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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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  /22

  $3,500 per month

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

  102 Chalker Beach Rd, Old Saybrook, CT 06475

  {Beach cottage -- available July 1, 2025 -- $3,500/month}. Spend a month or more in this charming Chalker Beach cottage! (anytime between July 1 - Oct 15). Located in a private association, this home is a short walk to the large sandy beach for pristine relaxation by the water. Walk for miles along adjoining beaches and neighborhoods during the day, and enjoy the magical pastel sunsets over the

  Erika Raffles William Pitt Sotheby's Int'l

  102 Chalker Beach Rd, Old Saybrook, CT 06475
• 

  $810,000 Sold Jun 30, 2025

  • 2,100 Sq Ft
  • $386/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1977

  27 Birch St, Old Saybrook, CT 06475

  Welcome to this beautifully updated 4 bedroom, 3 full bath home nestled in the heart of picturesque Old Saybrook. This property is perfectly situated within walking distance to town and close to beaches, yet tucked away on a quiet dead end street that feels worlds apart. Enjoy the best of both worlds, convenience and tranquility. Step onto the charming front porch, perfect for enjoying your

  Jennifer Pagan RE/MAX One

  27 Birch St, Old Saybrook, CT 06475
• 

  Est $445,792 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
• 

  

  /40

  $899,900 Pending

  • 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
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  /40

  $5,250 per month

  • 4 Beds
  • 4 Baths
  • 2,686 Sq Ft
  • House for Rent

  6 Barton Ave, Old Saybrook, CT 06475

  FURNISHED ACADEMIC RENTAL AVAILABLE FROM OCTOBER 1, 2025 - MAY 15, 2026. Welcome to the Oyster River and Saybrook Cove where you can move into this fully furnished rental and you will not need anything other than your personal effects. A lovely open concept remodel with a bright window filled living room, gourmet kitchen, and two areas for dining. The outdoor backyard patio is well equipped with

  Kara Bell J.M. REALTY

  6 Barton Ave, Old Saybrook, CT 06475
• 

  $670,000 Sold Jun 27, 2025

  • 1,870 Sq Ft
  • $358/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1980

  7 Beaver Dam Trail, Old Saybrook, CT 06475

  Welcome to your dream shoreline home in Old Saybrook-where small-town charm meets modern luxury. Set on a quiet cul de sac just minutes from the beach, schools, and shops, this like-new Colonial has been fully renovated and offers everything a young family could want. Inside, you'll find gleaming hardwood floors, a stunning new kitchen with leathered granite counters, center island, and breakfast

  Joel Lucas Coldwell Banker Realty

  7 Beaver Dam Trail, Old Saybrook, CT 06475
• 

  Est $542,719 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

Showing Results 41 - 80, Page 2 of 18