6,273

Old Saybrook, CT Homes

Section Image
  • 9 Barley Hill Rd, Old Saybrook, CT 06475
    9 Barley Hill Rd, Old Saybrook, CT 06475
    9 Barley Hill Rd, Old Saybrook, CT 06475
    /39

    $850,000

    $49K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,544 Sq Ft

    9 Barley Hill Rd, Old Saybrook, CT 06475

    This beautifully maintained home offers the perfect blend of luxury and comfort! The main level offers exceptional versatility with an open floor plan, hardwood floors, a luxurious primary bedroom suite, along with a living room, family room, gourmet kitchen and formal dining room designed for both relaxed living and elegant gatherings. The first floor primary bedroom suite features California

    Sharon Linder Berkshire Hathaway NE Prop.

    9 Barley Hill Rd, Old Saybrook, CT 06475
  • 3 Jorgensen Ln, Old Saybrook, CT 06475

    $887,000

    Sold Nov 24, 2025

    3 Jorgensen Ln, Old Saybrook, CT 06475

    • 4 Beds
    • 2.5 Baths
    • 2,784 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $319/SF
    • 26 Days On Market

    Current Estimated Value $915,586

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    3 Jorgensen Ln, Old Saybrook, CT 06475
  • 23 Meadowood Ln, Old Saybrook, CT 06475
    23 Meadowood Ln, Old Saybrook, CT 06475
    23 Meadowood Ln, Old Saybrook, CT 06475
    /19

    $669,900

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,818 Sq Ft

    23 Meadowood Ln, Old Saybrook, CT 06475

    ***HIGHEST AND BEST IN BY 5/13 AT 5PM ***A lovely renovated ranch in the heart of "Meadowood", a desirable family friendly community in the charming town of Old Saybrook. The home features hardwood floors throughout, and a comfortable open layout with a large living room, stylish dining room, and a beautiful kitchen designed by local Hanford Kitchens. Three ample bedrooms await just around the

    Craig Milton Re/Max Valley Shore

    23 Meadowood Ln, Old Saybrook, CT 06475
  • 350 Middlesex Turnpike, Old Saybrook, CT 06475

    $725,000

    Sold Aug 12, 2025

    350 Middlesex Turnpike, Old Saybrook, CT 06475

    • Land
    • 1.38 Acres
    • $525,362 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 468 Days On Market

    Current Estimated Value $728,680

    Last Listing Agent Michael Hvizdo Coldwell Banker Realty

    350 Middlesex Turnpike, Old Saybrook, CT 06475
  • 1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
    /6

    $695,000

    $300K PRICE DROP
    • Land
    • 1.16 Acres
    • $599,138 per Acre

    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475

    1.25 Acres in B4 Zone. Public water available, septic required. Traffic count 15,900.

    Maxwell Lyman Lyman Real Estate

    1333 Boston Post Rd Unit 1, Old Saybrook, CT 06475
  • 20 Hill St, Old Saybrook, CT 06475

    $700,000

    Sold Jan 07, 2026

    20 Hill St, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1930

    Last Sold Summary

    • 12% Below List Price
    • $489/SF
    • 132 Days On Market

    Current Estimated Value $717,466

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

    20 Hill St, Old Saybrook, CT 06475
  • 25 Sunset Rd Unit 3, Old Saybrook, CT 06475
    25 Sunset Rd Unit 3, Old Saybrook, CT 06475
    25 Sunset Rd Unit 3, Old Saybrook, CT 06475
    /39

    $660,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,565 Sq Ft

    25 Sunset Rd Unit 3, Old Saybrook, CT 06475

    Looking for a home that feels like vacation every day? Carefree coastal living can be yours at this stylish townhouse at the Oyster River Landing condos. With just 20 homes, residents enjoy beautiful grounds, sunsets, and a pool overlooking the private boat basin on the Oyster River. This leads out to Long Island Sound and is excellent for fishing, kayaking, and paddle boarding. As you enter the

    Rose McWaid William Raveis Real Estate

    25 Sunset Rd Unit 3, Old Saybrook, CT 06475
  • 21 Fenwick St, Old Saybrook, CT 06475

    $799,000

    Sold Mar 27, 2026

    21 Fenwick St, Old Saybrook, CT 06475

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1938

    Last Sold Summary

    • $558/SF
    • 120 Days On Market

    Current Estimated Value $803,629

    Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

    21 Fenwick St, Old Saybrook, CT 06475
  • 18 Old South Cove Rd, Old Saybrook, CT 06475
    18 Old South Cove Rd, Old Saybrook, CT 06475
    18 Old South Cove Rd, Old Saybrook, CT 06475
    /40

    $899,000

    $76K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,569 Sq Ft

    18 Old South Cove Rd, Old Saybrook, CT 06475

    Whether your vision is to Move-in, Renovate, or Custom Build from the ground up, this water-view coastal property is for you! Currently home to a classic 1,569 sq. ft. coastal ranch built on an oversized .42-acre water-view parcel, the true value of this premier Residential District A property lies in its exceptional dimensions, rare zoning advantages, and all the possibilities that come with the

    Steven Koleno Beycome of Connecticut

    18 Old South Cove Rd, Old Saybrook, CT 06475
  • 450 Maple Ave, Old Saybrook, CT 06475

    $3,200,000

    Sold Sep 10, 2025

    450 Maple Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 5 Baths
    • 4,435 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $722/SF
    • 20 Days On Market

    Current Estimated Value $3,355,814

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

    450 Maple Ave, Old Saybrook, CT 06475
  • 6 Trolley Crossing, Old Saybrook, CT 06475
    6 Trolley Crossing, Old Saybrook, CT 06475
    6 Trolley Crossing, Old Saybrook, CT 06475
    /33

    $997,000

    $103K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 3,917 Sq Ft

    6 Trolley Crossing, Old Saybrook, CT 06475

    Quintessential New England Gambrel Colonial with a dramatic sunroom addition and a brand new roof! Sited in a quiet cul-de-sac neighborhood, the gorgeous one acre grounds include numerous mature flowering trees and shrubs, as well as a pine tree perimeter for privacy. The original part of the 1st floor of the home includes a front to back living room with bookshelves, a formal dining room, a

    Donald Holland William Pitt Sotheby's Int'l

    6 Trolley Crossing, Old Saybrook, CT 06475
  • 134 School House Rd, Old Saybrook, CT 06475

    $925,000

    Sold Jul 18, 2025

    134 School House Rd, Old Saybrook, CT 06475

    • 4 Beds
    • 2.5 Baths
    • 4,559 Sq Ft
    • Built 1988

    Last Sold Summary

    • $203/SF
    • 28 Days On Market

    Current Estimated Value $1,119,693

    Last Listing Agent Tina Rupp William Pitt Sotheby's Int'l

    134 School House Rd, Old Saybrook, CT 06475
  • 175 N Cove Rd, Old Saybrook, CT 06475
    175 N Cove Rd, Old Saybrook, CT 06475
    175 N Cove Rd, Old Saybrook, CT 06475
    /40

    $3,695,000

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

    175 N Cove Rd, Old Saybrook, CT 06475

    An exceptional offering in the heart of North Cove, this storied estate presents a rare convergence of history, scale, and coastal prestige in Old Saybrook. Set on over an acre of beautifully sited grounds with direct water access and a private dock, the property offers a lifestyle that is both tranquil and connected, just moments from the Cove, local marinas, and the village center. The setting

    Susan Malan William Pitt Sotheby's Int'l

    175 N Cove Rd, Old Saybrook, CT 06475
  • 33 Fenwood Rd, Old Saybrook, CT 06475

    $815,000

    Sold Apr 17, 2026

    33 Fenwood Rd, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 2,042 Sq Ft
    • Built 1953

    Last Sold Summary

    • 5% Below List Price
    • $399/SF
    • 9 Days On Market

    Current Estimated Value $817,896

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    33 Fenwood Rd, Old Saybrook, CT 06475
  • 24 W Shore Dr, Old Saybrook, CT 06475
    24 W Shore Dr, Old Saybrook, CT 06475
    24 W Shore Dr, Old Saybrook, CT 06475
    /27

    $1,295,000

    $80K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 884 Sq Ft

    24 W Shore Dr, Old Saybrook, CT 06475

    Welcome to 24 W. Shore Dr. Old Saybrook, ideally located in one of Connecticut's most renowned beach communities-Cornfield Point Association. This year-round home offers the perfect blend of comfort, convenience, and stunning water views. This solid brick residence is move-in ready and features a remodeled kitchen with brand-new appliances, a sun-filled living room, three full-sized bedrooms, a

    David Rodriguez William Pitt Sotheby's Int'l

    24 W Shore Dr, Old Saybrook, CT 06475
  • 446 Main St Unit 9, Old Saybrook, CT 06475

    $1,420,000

    Sold Jun 17, 2026

    446 Main St Unit 9, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,294 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Above List Price
    • $619/SF
    • 30 Days On Market

    Current Estimated Value $1,234,495

    Last Listing Agent Maureen OGrady Compass Connecticut, LLC

    446 Main St Unit 9, Old Saybrook, CT 06475
  • 24 Seabreeze Rd, Old Saybrook, CT 06475
    24 Seabreeze Rd, Old Saybrook, CT 06475
    24 Seabreeze Rd, Old Saybrook, CT 06475
    /36

    $1,038,880

    • 3 Beds
    • 2 Baths
    • 1,952 Sq Ft

    24 Seabreeze Rd, Old Saybrook, CT 06475

    Nestled in the prestigious Cornfield Point Beach Association neighborhood. This ranch has one-level living, with ocean views! With upgrades and improvements including new flooring, active solar, Thermopane windows, Vinyl Siding, rain gutters, central air and heating system. Third bedroom includes a Murphy bed. A spacious open plan living room. Wall to wall windows that flood the space. Ceramic

    Brian Beaulieu Berkshire Hathaway NE Prop.

    24 Seabreeze Rd, Old Saybrook, CT 06475
  • 3 4th Ave, Old Saybrook, CT 06475

    $309,000

    Sold Nov 04, 2025

    3 4th Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1966

    Last Sold Summary

    • 23% Below List Price
    • $358/SF
    • 143 Days On Market

    Current Estimated Value $341,565

    Last Listing Agent Phil Ledwith Century 21 AllPoints Realty

    3 4th Ave, Old Saybrook, CT 06475
  • 13 Briarwood Dr, Old Saybrook, CT 06475
    13 Briarwood Dr, Old Saybrook, CT 06475
    13 Briarwood Dr, Old Saybrook, CT 06475
    /17

    $675,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    13 Briarwood Dr, Old Saybrook, CT 06475

    MAKE THIS HOUSE A HOME!! Investors, DIY buyers take note of this opportunity. A true fixer-upper being sold as-is. A sweet ranch with views of the marsh, Back River and Plum Bank out to Long Island Sound. 3 br, 1 1/2 bth set on .52 acres. Boarders open space with deeded beach rights to Cornfield Point Beach Enjoy spectacular sunsets and salt marsh views from your back porch Cozy fireplace in

    Joanne Gadon Coldwell Banker Realty

    13 Briarwood Dr, Old Saybrook, CT 06475
  • 46 Maple Ave, Old Saybrook, CT 06475

    $530,000

    Sold Dec 05, 2025

    46 Maple Ave, Old Saybrook, CT 06475

    • 4 Beds
    • 2 Baths
    • 3,190 Sq Ft
    • Built 1950

    Last Sold Summary

    • 18% Below List Price
    • $166/SF
    • 77 Days On Market

    Current Estimated Value $679,564

    Last Listing Agent Fran Manganello Coldwell Banker Realty

    46 Maple Ave, Old Saybrook, CT 06475
  • 6 Watch Hill Rd, Old Saybrook, CT 06475
    6 Watch Hill Rd, Old Saybrook, CT 06475
    6 Watch Hill Rd, Old Saybrook, CT 06475
    /15

    $551,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,830 Sq Ft

    6 Watch Hill Rd, Old Saybrook, CT 06475

    Attention Investors and Motivated Home Buyers. Welcome to 6 Watch Hill. Home offers eclectic feel. New owner will build off of this design. Home boast beautiful views and you can not help but to feel peace as you appreciate all the nature around you. Great stand alone garage with wonderful workspace on 2nd level. Sale is subject to probate approval.

    Tony Martin Home Pro Real Estate

    6 Watch Hill Rd, Old Saybrook, CT 06475
  • 78 Hartford Ave, Old Saybrook, CT 06475

    $751,500

    Sold Oct 15, 2025

    78 Hartford Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 1 Bath
    • 890 Sq Ft
    • Built 1930

    Last Sold Summary

    • 12% Below List Price
    • $844/SF
    • 106 Days On Market

    Current Estimated Value $768,315

    Last Listing Agent Robert Perriello Century 21 AllPoints Realty

    78 Hartford Ave, Old Saybrook, CT 06475
  • 25 Sunset Rd Unit 7, Old Saybrook, CT 06475

    $750,000

    Sold May 28, 2026

    25 Sunset Rd Unit 7, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,090 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $359/SF
    • 62 Days On Market

    Last Listing Agent Scott Nardozzi Cavanaugh & Company LLC

    25 Sunset Rd Unit 7, Old Saybrook, CT 06475
  • 71 Maple Ave, Old Saybrook, CT 06475

    $750,000

    Sold Jun 15, 2026

    71 Maple Ave, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 2,069 Sq Ft
    • Built 1961

    Last Sold Summary

    • 15% Above List Price
    • $362/SF
    • 3 Days On Market

    Current Estimated Value $655,827

    Last Listing Agent Tina Rupp William Pitt Sotheby's Int'l

    71 Maple Ave, Old Saybrook, CT 06475
  • 21 Wildwood Rd, Old Saybrook, CT 06475

    $900,000

    Sold Oct 30, 2025

    21 Wildwood Rd, Old Saybrook, CT 06475

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft
    • Built 1953

    Last Sold Summary

    • 28% Below List Price
    • $639/SF
    • 171 Days On Market

    Current Estimated Value $940,533

    Last Listing Agent Marc Delise Coldwell Banker Realty

    21 Wildwood Rd, Old Saybrook, CT 06475
  • 25 Pond Rd, Old Saybrook, CT 06475

    $595,000

    Sold Mar 30, 2026

    25 Pond Rd, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,731 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Above List Price
    • $344/SF
    • 18 Days On Market

    Current Estimated Value $596,761

    Last Listing Agent Suzanne McConville William Raveis Real Estate

    25 Pond Rd, Old Saybrook, CT 06475

Showing Results 201 - 240, Page 6 of 18

Connecticut Middlesex County Old Saybrook

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group