Old Saybrook, CT Homes

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  /40

  $759,900

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,474 Sq Ft

  2 Pheasant Hill Ln, Old Saybrook, CT 06475

  Gracious 4 bedroom/ three full baths Cape Cod with an attached two-car garage. Set on a picturesque, one-acre lightly wooded, corner lot with beautiful stone walls, mature plantings, gardens, large patio and an oversized L-shaped in-ground pool which becomes the centerpiece for summer enjoyment complete with lots of privacy. With approximately 2500 square feet of thoughtfully designed living

  Lisa Genovali Re/Max Valley Shore

  2 Pheasant Hill Ln, Old Saybrook, CT 06475
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  /6

  $2,650 Plus Fees

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

  31 River Ave, Old Saybrook, CT 06475

  Welcome to your new home in the charming Saybrook Manor district of Old Saybrook, Connecticut! This inviting Academic rental property offers a perfect blend of comfort and convenience, making it an ideal choice for those seeking a vibrant community atmosphere.Key property features include spacious bedrooms and well-appointed bathrooms, offering ample space for relaxation and daily living.

  31 River Ave, Old Saybrook, CT 06475
• 

  $525,000

  Sold Jun 15, 2026

  55 Woodland Dr, Old Saybrook, CT 06475

  • 4 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Above List Price
  • $486/SF
  • 8 Days On Market

  Current Estimated Value $542,842

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  55 Woodland Dr, Old Saybrook, CT 06475
• 

  Est $3,664,058

  Not Listed For Sale

  9 Whisper Cove Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 5 Baths
  • 4,768 Sq Ft
  • Built 2008

  9 Whisper Cove Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Tammy Tinnerello William Pitt Sotheby's Int'l
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  /39

  $874,900

  Pending

  • 2 Beds
  • 3 Baths
  • 2,209 Sq Ft

  86 Fenwood Dr, Old Saybrook, CT 06475

  Your Beach Retreat Awaits! Completely renovated and thoughtfully redesigned, 86 Fenwood Drive offers the perfect opportunity for a year-round residence or summer getaway. Ideally located just minutes from the kayak launch, cove, and beach, this charming home sits on a beautifully landscaped, level lot filled with mature plantings and inviting outdoor spaces. Step inside to discover a stunning

  Jeffrey Anderson William Pitt Sotheby's International Realty

  86 Fenwood Dr, Old Saybrook, CT 06475
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  /34

  $3,000 Per Month

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • House for Rent

  10 London Ct, Old Saybrook, CT 06475

  Welcome to Old Saybrook. This beautifully updated 4-bedroom, 2-bath academic rental offers the perfect blend of comfort and coastal living, complete with deeded beach rights to Cornfield Point Beach for the 2026-2027 academic calendar. Tucked away at the end of a quiet cul-de-sac on a full acre, this fully furnished home is truly move-in ready. The thoughtfully designed layout includes a heated

  Wendy Visgilio Coldwell Banker Realty

  10 London Ct, Old Saybrook, CT 06475
• 

  $707,500

  Sold Dec 19, 2025

  355 Main St, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 2,194 Sq Ft
  • Built 1919

  Last Sold Summary

  • 6% Below List Price
  • $322/SF
  • 187 Days On Market

  Current Estimated Value $779,414

  Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

  355 Main St, Old Saybrook, CT 06475
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  Est $1,726,529

  Not Listed For Sale

  23 Red Bird Trail, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 2,580 Sq Ft
  • Built 1955

  23 Red Bird Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Jay Cusack Better Homes and Gardens Real Estate Executive Real Estate
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  /22

  $526,250

  $113K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 1,038 Sq Ft

  9 Farview Ave, Old Saybrook, CT 06475

  Charming Coastal Ranch in an incredible Old Saybrook location! This well-maintained ranch offers the perfect blend of comfort, convenience, and shoreline lifestyle. An easy flow layout which includes 3 bedrooms, living room, dining room, kitchen, full bath and a full unfinished basement for additional storage or workshop. Step outside to a spacious backyard designed for entertaining, relaxing,

  Sharon Linder Berkshire Hathaway NE Prop.

  9 Farview Ave, Old Saybrook, CT 06475
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  /39

  $2,900 Per Month

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • House for Rent

  10 W View Rd, Old Saybrook, CT 06475

  Beautiful Knollwood Beach winter rental available 8/15/2026 through 5/31/27. Enjoy living one block from LIS with lovely walking path along the waterfront and association amenities like tennis, and a great park with playground and basketball court. Nicely decorated and never rented before. Lovely livingroom with fireplace , 3 bedrooms, one bathroom. Oversized one car garage ok for tenant storage

  Joel Lucas Coldwell Banker Realty

  10 W View Rd, Old Saybrook, CT 06475
• 

  $715,000

  Sold May 29, 2026

  3 Deerfield Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Above List Price
  • $373/SF
  • 1 Day On Market

  Current Estimated Value $716,386

  Last Listing Agent Pardi & Zucco Team William Pitt Sotheby's Int'l

  3 Deerfield Rd, Old Saybrook, CT 06475
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  Est $6,791,084

  Not Listed For Sale

  9 Pettipaug Ave, Old Saybrook, CT 06475

  • 7 Beds
  • 5.5 Baths
  • 7,465 Sq Ft
  • Built 1905

  9 Pettipaug Ave, Old Saybrook, CT 06475

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Christine Poppy Compass Connecticut, LLC
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  /18

  $1,450,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,570 Sq Ft

  81 Essex Rd, Old Saybrook, CT 06475

  Introducing a rare opportunity to build your dream home in one of Connecticut's most desirable shoreline communities. Located at 81 Essex Road in Old Saybrook, this to-be-built home by Silvin Homes offers the flexibility to choose from multiple thoughtfully designed floor plans and finishes, allowing you to create a home that fits your lifestyle and budget. What truly sets this property apart is

  Rachael Cisz Serhant Connecticut, LLC

  81 Essex Rd, Old Saybrook, CT 06475
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  /39

  $4,500 Per Month

  • 3 Beds
  • 3 Baths
  • 3,125 Sq Ft
  • House for Rent

  5 Woodland Dr, Old Saybrook, CT 06475

  WINTER RENTAL available September 15, 2026 through May 31, 2027 for $4,500/month. Enjoy spectacular Long Island Sound views from this beautifully renovated 3-bedroom, 3-bath home in the desirable Knollwood Beach Association. Tucked away on a quiet street just off Maple Avenue and only one street from the beach, this exceptional home offers unobstructed water views and a peaceful shoreline

  Joel Lucas Coldwell Banker Realty

  5 Woodland Dr, Old Saybrook, CT 06475
• 

  $480,000

  Sold Jun 16, 2026

  240 Elm St, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $342/SF
  • 26 Days On Market

  Current Estimated Value $490,399

  Last Listing Agent Sang Jee Eagle Eye Realty PLLC

  240 Elm St, Old Saybrook, CT 06475
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  Est $567,625

  Not Listed For Sale

  7 Windsor Oval, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,856 Sq Ft
  • Built 1961

  7 Windsor Oval, Old Saybrook, CT 06475

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  /5

  $675,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  9 Old Colony Rd, Old Saybrook, CT 06475

  Rare opportunity to create your dream home in one of Old Saybrook's most sought-after beach communities! Located across from Cornfield Point Beach Association, with deeded beach rights, this .23-acre property includes access to the beautiful sandy beach a short walk away making daily walks to the shoreline effortless. Surrounded by attractive homes, the setting alone makes this a standout

  Joel Lucas Coldwell Banker Realty

  9 Old Colony Rd, Old Saybrook, CT 06475
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  /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 of Long Island Sound at 28 Beach Rd West, Old Saybrook! Beautiful Academic Rental "beach" home, with 3 bedrooms and 2 baths, 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
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  $1,200,000

  Sold Jan 05, 2026

  25 Maplewood Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $421/SF
  • 97 Days On Market

  Current Estimated Value $1,213,654

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  25 Maplewood Rd, Old Saybrook, CT 06475
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  Est $859,681

  Not Listed For Sale

  16 Fordham Trail, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 3,673 Sq Ft
  • Built 1992

  16 Fordham Trail, Old Saybrook, CT 06475

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent WAYNE ARUTE Law Realty Group
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  /38

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  170 Old Post Rd, Old Saybrook, CT 06475

  Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil moldings, authentic hardware and classic

  Rose McWaid William Raveis Real Estate

  170 Old Post Rd, Old Saybrook, CT 06475
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  /16

  $1,950 Per Month

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

  119 Old Boston Post Rd Unit 2nd Floor, Old Saybrook, CT 06475

  Spacious 2nd floor apartment on the Old Boston Post Road is a wonderful location. There is so much within walking distance - or maybe a bicycle ride. The village center and surrounding area offers restaurants, town green, shops, Delicatessen, several banks, walk-in medical center, town hall, schools, library, parks, even the town beach and Saybrook Point. This 2 bedroom apartment features a

  Brian Jermainne Team Jermainne Real Estate Services, LLC

  119 Old Boston Post Rd Unit 2nd Floor, Old Saybrook, CT 06475
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  $460,000

  Sold Jun 16, 2026

  14 Denmore Ln, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $385/SF
  • 25 Days On Market

  Current Estimated Value $479,470

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC

  14 Denmore Ln, Old Saybrook, CT 06475
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  Est $672,115

  Not Listed For Sale

  1 Anchorage Ln, Old Saybrook, CT 06475

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft
  • Built 1955

  1 Anchorage Ln, Old Saybrook, CT 06475

  Last Sold Summary

  • 140 Days On Market

  Last Listing Agent Renee McCammon Berkshire Hathaway NE Prop.
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  /40

  $2,195,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,881 Sq Ft

  8 Owaneco Trail, Old Saybrook, CT 06475

  Welcome to this stunning gray shingle, Nantucket-style Cape Cod nestled in the sought-after Indiantown neighborhood of Old Saybrook - less than a quarter mile to the beach and a Private Marina! Offering over 2,800 square feet of beautifully appointed living space, this exceptional home was effectively built in 2018 and presents in excellent condition throughout. The open-concept floor plan

  Maddy Mattson Coldwell Banker Realty

  8 Owaneco Trail, Old Saybrook, CT 06475
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  /18

  $2,350 Per Month

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

  30 Mohican Rd, Old Saybrook, CT 06475

  Immaculate and beautifully updated academic rental located in the desirable Cornfield Point beach community. The interior features an open floor plan. The kitchen is nicely appointed. A washer and dryer are included inside the home. The primary bedroom is spacious with a workspace and attached flex space that functions as an attached den or living space. An attached garage is an added benefit.

  Marc Delise Coldwell Banker Realty

  30 Mohican Rd, Old Saybrook, CT 06475
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  $385,000

  Sold Jul 15, 2026

  39 Middletown Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 1 Bath
  • 640 Sq Ft
  • Built 1908

  Last Sold Summary

  • 14% Below List Price
  • $602/SF
  • 130 Days On Market

  Current Estimated Value $424,079

  Last Listing Agent Tracy Pentalow Property Shoppe, LLC

  39 Middletown Ave, Old Saybrook, CT 06475
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  Est $1,320,744

  Not Listed For Sale

  41 Cypress Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 3,010 Sq Ft
  • Built 1976

  41 Cypress Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent Lynn Toper CR Premier Properties
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  /31

  $1,375,000

  $215K PRICE DROP

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

  21 Fenbrook Rd, Old Saybrook, CT 06475

  Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first

  Ralph Harvey ListWithFreedom.com

  21 Fenbrook Rd, Old Saybrook, CT 06475
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  /15

  $14,400 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  2 Buckingham Ave, Old Saybrook, CT 06475

  Available for August Summer rental for 2-week intervals or full month. Large 4 bedroom with water views of marsh and Kayak water ways. There is boat launch access across street from garage for kayaks ,canoes small boat - tidal tides important. Outdoor shower. Wrap around covered deck. A great vacation resort capable of sleeping 8-10. Fully Furnished Rent Spree Applications

  Steve Waters William Raveis Real Estate

  2 Buckingham Ave, Old Saybrook, CT 06475
• 

  $870,000

  Sold Nov 20, 2025

  7 Sharon Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1978

  Last Sold Summary

  • 13% Below List Price
  • $330/SF
  • 129 Days On Market

  Current Estimated Value $876,609

  Last Listing Agent Jessica Blancato William Pitt Sotheby's Int'l

  7 Sharon Ln, Old Saybrook, CT 06475
• 

  Est $736,919

  Not Listed For Sale

  10 Allendale Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,924 Sq Ft
  • Built 1969

  10 Allendale Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Dana Gibson William Raveis Real Estate
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  /30

  $2,195,000

  Under Contract

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

  125 Main St, Old Saybrook, CT 06475

  Great mixed-use opportunity. Fully leased office building with town-approved one-bedroom apartment on Second Floor with kitchen, full bath including washer/dryer. Great opportunity to own a mixed-use property on beautiful Main Street in Old Saybrook. Established salon with long term lease on first floor. The one bedroom apartment on the second floor has been carpeted and painted and has separate

  Gary Marino William Raveis Real Estate

  125 Main St, Old Saybrook, CT 06475
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  /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 September 9, 2026 - May 2027 $6,500 per Month | Full Academic Term Preferred. Experience the best of Connecticut shoreline living in this exceptional Fenwick rental. Privately situated on a knoll overlooking picturesque marshlands, the home enjoys sweeping views of Long Island Sound and the historic Outer Light. Designed for both comfortable everyday

  Lynn Lehrman Re/Max Valley Shore

  3 Wilson Ave, Old Saybrook, CT 06475
• 

  $1,030,000

  Sold Jul 30, 2026

  96 Fenwood Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 3 Baths
  • 2,326 Sq Ft
  • Built 1961

  Last Sold Summary

  • 24% Below List Price
  • $443/SF
  • 292 Days On Market

  Current Estimated Value $1,289,917

  Last Listing Agent Eric Porco 4 Corners Realty LLC

  96 Fenwood Dr, Old Saybrook, CT 06475
• 

  Est $2,552,747

  Not Listed For Sale

  468 Main St, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 4,225 Sq Ft
  • Built 1995

  468 Main St, Old Saybrook, CT 06475

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l
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  /37

  $1,595,000

  $105K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  104 Knollwood Dr, Old Saybrook, CT 06475

  True tranquility awaits at this waterfront oasis! Unparalleled water views from every vantage point! Privately set on a generous 0.37-acre lot, this 3-bedroom home provides direct water access- perfect for kayaking out to Long Island Sound right from your backyard. Inside, the home blends charm and character with thoughtful updates. Its architectural lines evoke a Normandy chalet vibe, while the

  Karen Lee Coldwell Banker Realty

  104 Knollwood Dr, Old Saybrook, CT 06475
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  /9

  $4,200 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,732 Sq Ft
  • House for Rent

  5 Knollwood Dr, Old Saybrook, CT 06475

  Waterviews. Recently renovated year-round Cottage in Knollwood Beach Association 2 doors down from the waterfront. Incredible views of Long Island Sound. You will love the large covered porch and the designer white kitchen. Beautiful open flow on first floor with large dining area and gas fireplace in living-room. Home has 3 Bedrooms and 2.1 bathrooms. Nice back yard with outdoor shower. Tenant

  Joel Lucas Coldwell Banker Realty

  5 Knollwood Dr, Old Saybrook, CT 06475
• 

  $742,900

  Sold Oct 31, 2025

  16 Howard St, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $529/SF
  • 3 Days On Market

  Current Estimated Value $782,817

  Last Listing Agent Terry Kemper Coldwell Banker Realty

  16 Howard St, Old Saybrook, CT 06475
• 

  Est $451,133

  Not Listed For Sale

  10 Lookout Hill Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,936 Sq Ft
  • Built 1996

  10 Lookout Hill Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Bob Senger Berkshire Hathaway NE Prop.

Showing Results 41 - 80, Page 2 of 18