6,273

Old Saybrook, CT Homes

Section Image
  • 9 2nd Ave, Old Saybrook, CT 06475

    $500,000

    Sold May 08, 2026

    9 2nd Ave, Old Saybrook, CT 06475

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1959

    Last Sold Summary

    • 9% Above List Price
    • $481/SF
    • 2 Days On Market

    Current Estimated Value $449,385

    Last Listing Agent Sally Tucker Coldwell Banker Realty

    9 2nd Ave, Old Saybrook, CT 06475
  • 49 River St, Old Saybrook, CT 06475
    49 River St, Old Saybrook, CT 06475
    49 River St, Old Saybrook, CT 06475
    /29

    $599,000

    $26K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 2,860 Sq Ft

    49 River St, Old Saybrook, CT 06475

    Spacious village area colonial with lot's of space and in what a location, a short stroll to Main Street and convenient to shops, highways and the railroad station. Featuring 9 rooms and 4 bedrooms with a second upper level kitchenette, this floorplan suits all of your housing needs at a price which won't bust the budget. Could potentially accommodate an in-law use with the second kitchen.

    Rick Allen William Raveis Real Estate

    49 River St, Old Saybrook, CT 06475
  • 175 Ferry Rd Unit 4, Old Saybrook, CT 06475

    $585,000

    Sold Mar 13, 2026

    175 Ferry Rd Unit 4, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 1,852 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $316/SF
    • 16 Days On Market

    Current Estimated Value $594,682

    Last Listing Agent Gigi Giordano Taylor Compass Connecticut, LLC

    175 Ferry Rd Unit 4, Old Saybrook, CT 06475
  • 6 Fencove Ct, Old Saybrook, CT 06475
    6 Fencove Ct, Old Saybrook, CT 06475
    6 Fencove Ct, Old Saybrook, CT 06475
    /39

    $1,350,000

    $151K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,040 Sq Ft

    6 Fencove Ct, Old Saybrook, CT 06475

    Coastal living at its best in the desirable Fenwood District and Fenwood Beach Association! As a member, enjoy access to Fenwood Beach with panoramic views, sandy beach, and a picnic area.This move-in ready, updated home offers over 2,000 sq ft of thoughtfully designed living space, featuring 4 bedrooms, 3.5 baths, 2-car garage, central a/c, all nestled on a peaceful cul-de-sac with water views

    Laura Frisch Coldwell Banker Realty

    6 Fencove Ct, Old Saybrook, CT 06475
  • 55 Cypress Rd, Old Saybrook, CT 06475

    $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

    Current Estimated Value $973,488

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

    55 Cypress Rd, Old Saybrook, CT 06475
  • 29 Old Post Rd, Old Saybrook, CT 06475
    29 Old Post Rd, Old Saybrook, CT 06475
    29 Old Post Rd, Old Saybrook, CT 06475
    /40

    $745,000

    • 3 Beds
    • 2.5 Baths
    • 1,604 Sq Ft

    29 Old Post Rd, Old Saybrook, CT 06475

    Welcome to Crow's Nest, where classic New England country living meets direct waterfront luxury on the scenic Oyster River. Steeped in history, this enchanting historic farmhouse Circa 1850, is perfectly positioned along the west banks of the Oyster River, offering breathtaking water views from almost every single room. The character-rich interior features 3 bedrooms & 2.5 baths, offering cozy,

    Michael Barnes Silver and Oak Realty

    29 Old Post Rd, Old Saybrook, CT 06475
  • 25 Chalker Beach Rd, Old Saybrook, CT 06475

    $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 $550,517

    Last Listing Agent Susan Malton Coldwell Banker Realty

    25 Chalker Beach Rd, Old Saybrook, CT 06475
  • 2 Old South Cove Rd, Old Saybrook, CT 06475
    2 Old South Cove Rd, Old Saybrook, CT 06475
    2 Old South Cove Rd, Old Saybrook, CT 06475
    /40

    $1,499,000

    New Construction Open Sun 12PM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    2 Old South Cove Rd, Old Saybrook, CT 06475

    Welcome to one of Old Saybrook's most compelling luxury opportunities. Move in now and enjoy the summer at Saybrook Point. Immediate occupancy and flexible closing arrangements available for qualified buyers. Perfectly positioned in the heart of renowned Saybrook Point, this newly constructed coastal residence offers something increasingly difficult to find along the Connecticut shoreline: modern

    Michael Riccio Calcagni Real Estate

    2 Old South Cove Rd, Old Saybrook, CT 06475
  • 18 Lynde St, Old Saybrook, CT 06475

    $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 $564,775

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

    18 Lynde St, Old Saybrook, CT 06475
  • 44 Coulter St, Old Saybrook, CT 06475
    44 Coulter St, Old Saybrook, CT 06475
    44 Coulter St, Old Saybrook, CT 06475
    /10

    $450,000

    Open Sat 12PM - 3PM
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    44 Coulter St, Old Saybrook, CT 06475

    Located in one of Connecticut's most desirable shoreline communities, this 3-bedroom ranch offers an incredible opportunity to create the home of your dreams. Just steps from downtown Old Saybrook and just up the street from one of the best scenic views in town. You'll enjoy easy access to shops, restaurants, marinas, beaches, and all the coastal charm this beloved town has to offer. The seller

    Lisa Aranci Berkshire Hathaway NE Prop.

    44 Coulter St, Old Saybrook, CT 06475
  • 19 Hartford Ave, Old Saybrook, CT 06475

    $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 $649,096

    Last Listing Agent Frank Fonteyn Prestige Realty Group

    19 Hartford Ave, Old Saybrook, CT 06475
  • 92 Bokum Rd, Old Saybrook, CT 06475
    92 Bokum Rd, Old Saybrook, CT 06475
    92 Bokum Rd, Old Saybrook, CT 06475
    /40

    $559,000

    • 2 Beds
    • 1.5 Baths
    • 1,376 Sq Ft

    92 Bokum Rd, Old Saybrook, CT 06475

    A rare and captivating offering, this enchanting storybook residence has been beautifully reimagined to deliver a seamless blend of historic charm and refined design. Whether you choose to continue its success as a turnkey Airbnb investment or keep it for your own year round or weekend retreat, the possibilities are as inviting as the home itself. Thoughtfully updated with a brand new roof and

    Linda Toscano Coldwell Banker Realty

    92 Bokum Rd, Old Saybrook, CT 06475
  • 66 Pennywise Ln, Old Saybrook, CT 06475

    $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

    Current Estimated Value $1,486,612

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    66 Pennywise Ln, Old Saybrook, CT 06475
  • 208 Ingham Hill Rd, Old Saybrook, CT 06475
    208 Ingham Hill Rd, Old Saybrook, CT 06475
    208 Ingham Hill Rd, Old Saybrook, CT 06475
    /5

    $615,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,926 Sq Ft

    208 Ingham Hill Rd, Old Saybrook, CT 06475

    Location & Potential! Spacious Cape Cod in serene setting on over 2 acres close to town & shopping. With some cosmetic TLC you can turn this into a beautiful house that you will be proud to make home. Newer roof, partially finished basement with seperate heating zone. Fully applianced kitchen with newer refrigerator. First floor laundry and beautiful sunroom. House being sold "As Is". Please - Do

    Greg Young Berkshire Hathaway NE Prop.

    208 Ingham Hill Rd, Old Saybrook, CT 06475
  • 104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475

    $505,000

    Sold Jul 07, 2025

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

    • 2 Beds
    • 1.5 Baths
    • 1,557 Sq Ft
    • Built 1978

    Last Sold Summary

    • 7% Below List Price
    • $324/SF
    • 101 Days On Market

    Last Listing Agent Lisa Genovali Re/Max Valley Shore

    104 Sandy Point Rd Unit 104, Old Saybrook, CT 06475
  • 20 Saltus Dr, Old Saybrook, CT 06475
    20 Saltus Dr, Old Saybrook, CT 06475
    20 Saltus Dr, Old Saybrook, CT 06475
    /40

    $9,850,000

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

    20 Saltus Dr, Old Saybrook, CT 06475

    YOUR OWN PRIVATE COUNTRY CLUB! Enjoy the expansive 3500 sf granite terrace, a heated saltwater swimming pool, a deep water dock and a pool house with a full kitchen and seating for 10! This modern masterpiece, sited to take full advantage of a private 1.6 acre waterfront location overlooking North Cove and the Connecticut River has been constructed with the best curated materials. 20 Saltus Drive

    Margaret Muir William Pitt Sotheby's Int'l

    20 Saltus Dr, Old Saybrook, CT 06475
  • 8 Cromwell Place, Old Saybrook, CT 06475

    $1,025,000

    Sold Jul 25, 2025

    8 Cromwell Place, Old Saybrook, CT 06475

    • 4 Beds
    • 2.5 Baths
    • 3,730 Sq Ft
    • Built 1957

    Last Sold Summary

    • 14% Below List Price
    • $275/SF
    • 58 Days On Market

    Current Estimated Value $1,096,657

    Last Listing Agent Roxanne Quinn Coldwell Banker Realty

    8 Cromwell Place, Old Saybrook, CT 06475
  • 100 Sheffield St Unit A2, Old Saybrook, CT 06475
    100 Sheffield St Unit A2, Old Saybrook, CT 06475
    100 Sheffield St Unit A2, Old Saybrook, CT 06475
    /40

    $685,000

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 2,002 Sq Ft

    100 Sheffield St Unit A2, Old Saybrook, CT 06475

    Nestled within The Cove, a serene community on Old Saybrook's storied North Cove, this beautifully appointed townhouse offers the quintessential Connecticut shoreline lifestyle, where the Connecticut River meets the estuary and the ever-changing, breathtaking natural backdrop is your constant companion. The welcoming foyer has abundant closet space and a convenient half bath. The kitchen with

    Pamela Kirkby Coldwell Banker Realty

    100 Sheffield St Unit A2, Old Saybrook, CT 06475
  • 5 Sunrise Ave, Old Saybrook, CT 06475

    $400,000

    Sold Jun 12, 2026

    5 Sunrise Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 1 Bath
    • 1,064 Sq Ft
    • Built 1962

    Last Sold Summary

    • 11% Below List Price
    • $376/SF
    • 92 Days On Market

    Current Estimated Value $420,888

    Last Listing Agent Terry McDonald McDonald Real Estate, LLC

    5 Sunrise Ave, Old Saybrook, CT 06475
  • 77 Essex Rd, Old Saybrook, CT 06475
    77 Essex Rd, Old Saybrook, CT 06475
    77 Essex Rd, Old Saybrook, CT 06475
    /36

    $1,495,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 2,890 Sq Ft

    77 Essex Rd, Old Saybrook, CT 06475

    Set on .62 acres along a protected canal just off the Connecticut River, this custom-built waterfront Cape offers more than 100 feet of bulkhead frontage, along with a floating dock equipped with power and water suitable for a variety of boats and watercraft. Offering 3 bedrooms and 3.5 baths, the home was designed to capture natural light and water views with an open floorplan, abundant windows,

    Joseph Rhodes Coldwell Banker Realty

    77 Essex Rd, Old Saybrook, CT 06475
  • 6 West St, Old Saybrook, CT 06475

    $410,000

    Sold Jul 15, 2025

    6 West St, Old Saybrook, CT 06475

    • 2 Beds
    • 1 Bath
    • 826 Sq Ft
    • Built 1930

    Last Sold Summary

    • 11% Below List Price
    • $496/SF
    • 111 Days On Market

    Current Estimated Value $442,930

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    6 West St, Old Saybrook, CT 06475
  • 34 Briarcliffe Trail, Old Saybrook, CT 06475
    34 Briarcliffe Trail, Old Saybrook, CT 06475
    34 Briarcliffe Trail, Old Saybrook, CT 06475
    /40

    $1,224,900

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 3,720 Sq Ft

    34 Briarcliffe Trail, Old Saybrook, CT 06475

    Welcome to this exceptional 3700 sq ft, move-in ready home, privately situated on a quiet private road and surrounded by landscaped grounds. Set on a beautifully maintained 1.3 acre lot with a lightly wooded backdrop and charming stone wall accents, this property offers the perfect blend of privacy, space, and timeless appeal. The brick exterior creates stunning curb appeal, while inside you'll

    Eric Schuell RE/MAX Right Choice

    34 Briarcliffe Trail, Old Saybrook, CT 06475
  • 122 Old Post Rd, Old Saybrook, CT 06475

    $962,500

    Sold Mar 19, 2026

    122 Old Post Rd, Old Saybrook, CT 06475

    • 3 Beds
    • 2.5 Baths
    • 2,467 Sq Ft
    • Built 1991

    Last Sold Summary

    • 14% Below List Price
    • $390/SF
    • 158 Days On Market

    Current Estimated Value $1,019,729

    Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

    122 Old Post Rd, Old Saybrook, CT 06475
  • 61 Ingham Hill Rd, Old Saybrook, CT 06475
    61 Ingham Hill Rd, Old Saybrook, CT 06475
    61 Ingham Hill Rd, Old Saybrook, CT 06475
    /32

    $429,000

    $20K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,205 Sq Ft

    61 Ingham Hill Rd, Old Saybrook, CT 06475

    Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from Old Saybrook's stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, you'll find a spacious area that offers endless possibilities-use it as an eating area, a flex office, or even a sleeping space. The open floor plan invites effortless

    Gigi Giordano Taylor Compass Connecticut, LLC

    61 Ingham Hill Rd, Old Saybrook, CT 06475
  • 5 Fox Hollow Rd, Old Saybrook, CT 06475

    $722,500

    Sold Dec 05, 2025

    5 Fox Hollow Rd, Old Saybrook, CT 06475

    • 4 Beds
    • 3 Baths
    • 2,142 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $337/SF
    • 63 Days On Market

    Current Estimated Value $755,182

    Last Listing Agent Suzanne McConville William Raveis Real Estate

    5 Fox Hollow Rd, Old Saybrook, CT 06475
  • 12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    /39

    $5,900,000

    • 4 Beds
    • 4 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
  • 14 Watrous Point Rd, Old Saybrook, CT 06475

    $566,000

    Sold Oct 01, 2025

    14 Watrous Point Rd, Old Saybrook, CT 06475

    • 4 Beds
    • 2.5 Baths
    • 2,152 Sq Ft
    • Built 1966

    Last Sold Summary

    • 13% Below List Price
    • $263/SF
    • 3 Days On Market

    Current Estimated Value $680,682

    Last Listing Agent Suzanne McConville William Raveis Real Estate

    14 Watrous Point Rd, Old Saybrook, CT 06475

Showing Results 121 - 160, Page 4 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