Old Saybrook, CT Homes

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  $459,999

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft

  5 Sunrise Ave, Old Saybrook, CT 06475

  Welcome to 5 Sunrise Ave., Old Saybrook on the Connecticut Shoreline nothing to do with this one level ranch. This lovely home has three bedrooms, updated bath, updated kitchen, dining / living room. Hardwood floors, Stainless Steel Appliances, white cabinetry and an island for the inspiring chef to create and perfect their culinary skills. Entertain at home enjoy a lovely backyard with an

  Terry McDonald McDonald Real Estate, LLC

  5 Sunrise Ave, Old Saybrook, CT 06475
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  $2,000 total monthly price

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

  41 Town Beach Rd, Old Saybrook, CT 06475

  Academic lease only. Fully furnished rental available 9/2/25. Sparkling clean, hurry, this one won't last! Remodeled kitchen, fenced in back yard, new furniture, fireplace. Owner is a licensed Broker in the State of Connecticut. a great little place to live amazing sunsets trash pick up included

  George Agnelli Agnelli Real Estate

  41 Town Beach Rd, Old Saybrook, CT 06475
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  $850,000 Sold Sep 08, 2025

  122 College St, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 3,200 Sq Ft
  • Built 1890

  Last Sold Summary

  • 29% Below List Price
  • $266/SF
  • 77 Days On Market

  Current Estimated Value $881,715

  Last Listing Agent Mary McDonald Coldwell Banker Realty

  122 College St, Old Saybrook, CT 06475
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  Est $115,299 Not Listed For Sale

  22 Ragged Rock Rd, Old Saybrook, CT 06475

  22 Ragged Rock Rd, Old Saybrook, CT 06475
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  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,518 Sq Ft

  175 N Cove Rd, Old Saybrook, CT 06475

  Every home tells a story and the often admired c.1704 Black Horse Tavern in historic North Cove is no exception. Located at the waters edge and offering expansive water views, this stunning private residence is rich in both local history and architectural detail. Meticulously curated to perfection, quality of craftsmanship is evident throughout. A warm and welcoming entry leads to elegant

  Kyle Hinding Coldwell Banker Realty

  175 N Cove Rd, Old Saybrook, CT 06475
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  /22

  $4,500 total monthly price

  • 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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  $620,000 Sold Sep 30, 2025

  1 Hartford Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,762 Sq Ft
  • Built 1940

  Last Sold Summary

  • 11% Below List Price
  • $352/SF
  • 45 Days On Market

  Last Listing Agent Bryan Neurath Country Manor Realty

  1 Hartford Ave, Old Saybrook, CT 06475
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  Est $972,146 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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  $925,400 Under Contract

  • 5 Beds
  • 4 Baths
  • 2,938 Sq Ft

  179 Bokum Rd, Old Saybrook, CT 06475

  Unique Multi-Generational Property on 2+ Private Acres. A truly rare opportunity: two connected yet fully private residences set on 2.02 serene acres bordering the breathtaking 1,000-acre "Preserve". An impressive (24' x 40') heated, two-story barn with a loft offers endless possibilities for contractors, hobbyists, collectors, or creatives seeking a private studio or workshop. Primary Residence:

  Craig Milton Re/Max Valley Shore

  179 Bokum Rd, Old Saybrook, CT 06475
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  $749,000 Sold Aug 01, 2025

  509 Main St Unit 6, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 2011

  Last Sold Summary

  • $436/SF
  • 47 Days On Market

  Current Estimated Value $734,153

  Last Listing Agent Jake Pulcini Chiarito Real Estate LLC

  509 Main St Unit 6, Old Saybrook, CT 06475
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  Est $581,368 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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  $735,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  100 Dudley Ave Unit D20, Old Saybrook, CT 06475

  Impeccably Renovated Waterfront Condominium in Coveted Sheltered Cove! Welcome to this beautifully renovated, turn-key condominium in the highly sought-after Sheltered Cove community of Old Saybrook. Every detail has been thoughtfully updated, blending modern comfort with timeless coastal charm. Step into a bright, open-concept kitchen featuring sleek stainless steel appliances, abundant storage,

  Susie Kelly Coldwell Banker Realty

  100 Dudley Ave Unit D20, Old Saybrook, CT 06475
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  $725,000 Sold May 12, 2025

  8 Acorn Dr, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,448 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Above List Price
  • $296/SF
  • 17 Days On Market

  Current Estimated Value $732,671

  Last Listing Agent Craig Milton Re/Max Valley Shore

  8 Acorn Dr, Old Saybrook, CT 06475
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  Est $1,105,874 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,048 Sq Ft

  10 Turnstone Rd, Essex, CT 06426

  10 Turnstone Rd, Essex, CT 06426
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  $159,900

  • Land
  • 0.16 Acre
  • $999,375 per Acre

  6 South St, Old Saybrook, CT 06475

  Build Your Dream Home in Coastal Old Saybrook! A rare opportunity awaits you... Are you ready to create your shoreline oasis? Look no further than this Fully Approved Residential Building Lot with many enticing features that make it a special gem. Come enjoy salty breezes and serene water views... sunsets and seagulls await! Located in a residential neighborhood on a road with two other homes

  Cheryl Keithan Coldwell Banker Realty

  6 South St, Old Saybrook, CT 06475
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  $476,000 Sold Feb 19, 2025

  12 Forest Glen Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 2,248 Sq Ft
  • Built 1979

  Last Sold Summary

  • 39% Below List Price
  • $212/SF
  • 207 Days On Market

  Current Estimated Value $516,818

  Last Listing Agent Nick Prevost William Raveis Real Estate

  12 Forest Glen Rd, Old Saybrook, CT 06475
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  Est $425,961 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

  $895,000

  • 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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  $555,000 Sold Mar 28, 2025

  4 Patterson Place, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $317/SF
  • 60 Days On Market

  Current Estimated Value $578,921

  Last Listing Agent Lynn Lehrman Re/Max Valley Shore

  4 Patterson Place, Old Saybrook, CT 06475
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  Est $557,467 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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  $9,850,000

  • 5 Beds
  • 7.5 Baths
  • 9,481 Sq Ft

  20 Saltus Dr, Old Saybrook, CT 06475

  An EXTRAORDINARY MODERN MASTERPIECE: Inspired by renowned architect Frank Lloyd Wright, sited to take full advantage of an exceptional, private 1.6 acre waterfront location overlooking North Cove and the CT River, and constructed with meticulous care and the best of the best curated materials, 20 Saltus Drive offers a luxurious, comfortable lifestyle with panoramic water views from almost every

  Margaret Muir William Pitt Sotheby's Int'l

  20 Saltus Dr, Old Saybrook, CT 06475
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  $225,000 Sold Mar 24, 2025

  711 Middlesex Turnpike, Old Saybrook, CT 06475

  • Land
  • 2.2 Acres
  • $102,273 per Acre

  Last Sold Summary

  • 25% Below List Price
  • 147 Days On Market

  Current Estimated Value $234,988

  Last Listing Agent Rick Allen William Raveis Real Estate

  711 Middlesex Turnpike, Old Saybrook, CT 06475
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  Est $631,447 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
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  $805,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  4 Gibbons Cir, Old Saybrook, CT 06475

  North Cove Opportunity in Prime Setting with some water views set in one of Old Saybrook's most desirable neighborhoods. This North Cove property offers an exceptional location and beautiful grounds with a sparkling in-ground pool. Owned by the same family since 1973, the home has been lovingly cared for and is being offered in "as is" condition - ready for renovation or a complete rebuild to

  Joel Lucas Coldwell Banker Realty

  4 Gibbons Cir, Old Saybrook, CT 06475
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  $650,000 Sold Dec 30, 2024

  63 Obed Heights, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft
  • Built 2002

  Last Sold Summary

  • $247/SF
  • 9 Days On Market

  Current Estimated Value $685,766

  Last Listing Agent Adam Bronko RE/MAX RISE

  63 Obed Heights, Old Saybrook, CT 06475
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  Est $1,024,249 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,178 Sq Ft

  8 Maynard Cir, Old Saybrook, CT 06475

  8 Maynard Cir, Old Saybrook, CT 06475
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  $2,795,000

  • 3 Beds
  • 3 Baths
  • 3,389 Sq Ft

  372 Maple Ave, Old Saybrook, CT 06475

  Most beach homes ask you to choose: location or amenities, space or style, primary home or vacation retreat. This one says "why not both?" Perfectly positioned just 50 steps from Knollwood Beach, this spacious 3-bedroom 3-bath sanctuary delivers the rare combination of prime beach access and every amenity you'd expect from a year-round residence. A stress free move-in is possible here, as this

  Teri Lewis William Pitt Sotheby's Int'l

  372 Maple Ave, Old Saybrook, CT 06475
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  $893,500 Sold Dec 05, 2025

  55 Cypress Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $466/SF
  • 21 Days On Market

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

  55 Cypress Rd, Old Saybrook, CT 06475
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  Est $458,070 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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  $799,000

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft

  33 Fenwood Rd, Old Saybrook, CT 06475

  Fenwood Beach Association! This beautifully renovated home is ready for you to move right in to this newly updated home. The light-filled interior offers an open flow between the kitchen, dining, and living areas, perfect for relaxed coastal living. The primary suite features a gorgeous new full bath, while the finished lower level adds 700 sq ft of flexible space currently used as a family room

  Joel Lucas Coldwell Banker Realty

  33 Fenwood Rd, Old Saybrook, CT 06475
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  $520,000 Sold Jul 07, 2025

  25 Chalker Beach Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 922 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Below List Price
  • $564/SF
  • 122 Days On Market

  Current Estimated Value $523,058

  Last Listing Agent Susan Malton Coldwell Banker Realty

  25 Chalker Beach Rd, Old Saybrook, CT 06475
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  Est $461,979 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
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  $850,000 Under Contract

  • Land
  • 26.41 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
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  $539,000 Sold Aug 27, 2025

  18 Lynde St, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,185 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Below List Price
  • $455/SF
  • 43 Days On Market

  Current Estimated Value $536,750

  Last Listing Agent Liz Squillacote William Pitt Sotheby's Int'l

  18 Lynde St, Old Saybrook, CT 06475
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  Est $570,781 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
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  $575,000

  • Land
  • 0.48 Acre
  • $1,197,917 per Acre

  10 Mulberry St, Old Saybrook, CT 06475

  Approved building lot with water views. Located at the end of Mulberry, very private location yet close to downtown and Saybrook Point Resort & Marina. 1/2 ac already cleared. Lot must be sold with 7 Willard Ave

  Steve Wollman Wollman Realty

  10 Mulberry St, Old Saybrook, CT 06475
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  $625,000 Sold Sep 03, 2025

  19 Hartford Ave, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 1,249 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Above List Price
  • $500/SF
  • 47 Days On Market

  Current Estimated Value $609,112

  Last Listing Agent Frank Fonteyn Prestige Realty Group

  19 Hartford Ave, Old Saybrook, CT 06475
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  Est $1,240,995 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  11 Beechwood Rd, Old Saybrook, CT 06475

  11 Beechwood Rd, Old Saybrook, CT 06475
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  $6,400,000

  • 4 Beds
  • 4.5 Baths
  • 5,651 Sq Ft

  12 Rocky Point Rd, Old Saybrook, CT 06475

  Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy

  Sharon Linder Berkshire Hathaway NE Prop.

  12 Rocky Point Rd, Old Saybrook, CT 06475
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  $1,495,000 Sold Dec 01, 2025

  66 Pennywise Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 3.5 Baths
  • 2,425 Sq Ft
  • Built 1790

  Last Sold Summary

  • 7% Above List Price
  • $616/SF
  • 1 Day On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  66 Pennywise Ln, Old Saybrook, CT 06475

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