6,228

Old Saybrook, CT Homes

Section Image Section Image
  • /38

    $968,800

    Pending
    • 2 Beds
    • 2.5 Baths
    • 2,823 Sq Ft

    25 Sheffield St Unit 3, Old Saybrook, CT 06475

    Experience refined coastal living in this stunning end-unit townhome, completed in 2021 and ideally located in the heart of downtown Old Saybrook. This exceptional residence offers convenient access to dining, shopping, the Katharine Hepburn Cultural Arts Center, Saybrook Point Marina, and local beaches. Bathed in natural light, the home features a spacious open floor plan with gleaming hardwood

    Agent Photo

    Nick Prevost

    William Raveis Real Estate

    25 Sheffield St Unit 3, Old Saybrook, CT 06475
  • /31

    Starting at $3,608

    Total Monthly Price

    • 2 Beds

    7 N Main St, Old Saybrook, CT 06475

    Where Old Meets New...... Old Saybrook is one of the most charming, historical, and sought-after towns in Connecticut. SAYBROOK STATION is one of the only modern luxury apartment communities in the area, built near Saybrook’s historic train station. This central location in the heart of everything is also only four minutes from the Old Saybrook Town Green – yes, we’ve made a place where old truly

    Saybrook Station

    7 N Main St, Old Saybrook, CT 06475
  • 99 Maple Ave, Old Saybrook, CT 06475

    $675,000

    Sold Feb 20, 2026

    99 Maple Ave, Old Saybrook, CT 06475

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Above List Price
    • $577/SF
    • 34 Days On Market

    Current Estimated Value $672,161

    Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

    99 Maple Ave, Old Saybrook, CT 06475
    • 47 Great Hammock Rd, Old Saybrook, CT 06475

      Est $775,613

      Not Listed For Sale

      47 Great Hammock Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 2 Baths
      • 1,587 Sq Ft
      • Built 1961
      47 Great Hammock Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Nick Prevost William Raveis Real Estate

  • /38

    $800,000

    Open Sat 12PM - 2PM
    • 2 Beds
    • 1 Bath
    • 1,478 Sq Ft

    25 River Ave, Old Saybrook, CT 06475

    Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants,

    Agent Photo

    Linda O'Hara

    William Raveis Real Estate

    25 River Ave, Old Saybrook, CT 06475
  • /35

    Starting at $3,500 Plus Fees

    • 2 Beds

    99 Lynde St, Old Saybrook, CT 06475

    Welcome to Hanford Commons – The Definition of LuxuryDiscover modern living at its finest with our brand-new apartments in the picturesque town of Old Saybrook. Hanford Commons perfectly blends style, convenience, and comfort, offering you a home that exceeds expectations. Each thoughtfully designed unit features stainless steel appliances, an in-unit washer and dryer, central heating and

    Hanford Commons

    99 Lynde St, Old Saybrook, CT 06475
  • 105 Fenwood Dr, Old Saybrook, CT 06475

    $1,305,000

    Sold Apr 30, 2026

    105 Fenwood Dr, Old Saybrook, CT 06475

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft
    • Built 1961

    Last Sold Summary

    • 7% Below List Price
    • $683/SF
    • 56 Days On Market

    Current Estimated Value $1,303,603

    Last Listing Agent Jodi Serapilia Seaport Real Estate Services

    105 Fenwood Dr, Old Saybrook, CT 06475
    • 100 Dudley Ave Unit B8, Old Saybrook, CT 06475

      Est $776,732

      Not Listed For Sale

      100 Dudley Ave Unit B8, Old Saybrook, CT 06475

      • 2 Beds
      • 2.5 Baths
      • 2,236 Sq Ft
      • Built 1979
      100 Dudley Ave Unit B8, Old Saybrook, CT 06475

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Rose Ciardiello William Raveis Real Estate

  • /40

    $584,900

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,290 Sq Ft

    21 Baum Ave, Old Saybrook, CT 06475

    Backyard goals? Achieved. Welcome to your own private oasis in the heart of Old Saybrook! Surrounded by low-maintenance vinyl fencing, lush lawn complete w/irrigation, this incredible outdoor space was made for summer--backyard BBQs, morning coffee under the pergola, & relaxing with family & friends. A spacious patio sets the stage for effortless entertaining, while the oversized shed provides

    Agent Photo

    Courtney Cusano

    Coldwell Banker Realty

    21 Baum Ave, Old Saybrook, CT 06475
  • /7

    $3,500 Plus Fees

    • 4 Beds
    • 2.5 Baths
    • 3,976 Sq Ft
    • House for Rent

    6 Leada Woods Rd, Old Saybrook, CT 06475

    Property Id: 2760013 Beautiful estate-like property on 2 acres in Old Saybrook. Short drive to town. Walk to the 900 acre Preserve for mountain biking and hiking. 3 bedrooms + den, 2.5 baths. Recently remodeled kitchen. Available as an academic rental (Sep - May).

    6 Leada Woods Rd, Old Saybrook, CT 06475
  • 143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475

    $550,000

    Sold Nov 19, 2025

    143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475

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

    Last Sold Summary

    • 11% Below List Price
    • $353/SF
    • 133 Days On Market

    Current Estimated Value $585,543

    Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

    143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475
    • 15 Buckingham Ave, Old Saybrook, CT 06475

      Est $1,252,522

      Not Listed For Sale

      15 Buckingham Ave, Old Saybrook, CT 06475

      • 3 Beds
      • 3 Baths
      • 2,132 Sq Ft
      • Built 2007
      15 Buckingham Ave, Old Saybrook, CT 06475

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Colette Harron William Pitt Sotheby's Int'l

  • /40

    $699,000

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    8 Kenn Rd, Old Saybrook, CT 06475

    Coastal living is calling! This is a fully furnished shoreline retreat set within the sought-after Chalker Beach Association. Offered As-Is and thoughtfully updated, this inviting home is ideal as a year-round residence, weekend escape, or classic summer getaway. With marsh views, salt air, and a relaxed beach-community setting, this is a turnkey opportunity designed for immediate enjoyment

    Agent Photo

    Michael Marsden

    Compass Connecticut, LLC

    8 Kenn Rd, Old Saybrook, CT 06475
  • /28

    $3,500

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • House for Rent

    84 Spencer Plain Rd, Old Saybrook, CT 06475

    3 bed 2 bath ground up remodel. Stainless steel appliance in home. Fridge dishwasher stove and microwave. Washer dryer down stairs and up included. New everything wood floors ceiling fans full island for entertaining. Furnace is gas, central a/c and plenty of outside under cover porch. Tv mounts in wall for flat screens. Double closet master bedroom. Huge bedroom 2 and 3. Huge 1 acre with

    84 Spencer Plain Rd, Old Saybrook, CT 06475
  • 10 Trolley Crossing, Old Saybrook, CT 06475

    $1,065,000

    Sold Jun 18, 2026

    10 Trolley Crossing, Old Saybrook, CT 06475

    • 3 Beds
    • 2.5 Baths
    • 3,376 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $315/SF
    • 40 Days On Market

    Current Estimated Value $1,069,748

    Last Listing Agent Nancy Mesham Coldwell Banker Realty

    10 Trolley Crossing, Old Saybrook, CT 06475
    • 27 Barnes Rd, Old Saybrook, CT 06475

      Est $809,846

      Not Listed For Sale

      27 Barnes Rd, Old Saybrook, CT 06475

      • 3 Beds
      • 1 Bath
      • 762 Sq Ft
      • Built 1955
      27 Barnes Rd, Old Saybrook, CT 06475

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Debra Pliego Essentia Realty

  • /40

    $2,899,900

    • 5 Beds
    • 4.5 Baths
    • 5,062 Sq Ft

    2 Captains Ln, Old Saybrook, CT 06475

    Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear

    Bill Heenan William Raveis Real Estate

    2 Captains Ln, Old Saybrook, CT 06475
  • /36

    $2,600 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft
    • House for Rent

    4 Elinor Rd, Old Saybrook, CT 06475

    CHALKER BEACH ACADEMIC RENTAL AVAILABLE 9/15/26 - 5/15/26. Adorable fully furnished 3 bedroom, 1.1 bathroom Cape featuring kitchen open to dining room, living room, 1 bedroom on the main level, 2 bedrooms on the 2nd floor, 3 season screened in porch, outdoor shower, off street parking for 4 cars. Tenants will be responsible for water, electric (lights, hot water, AC & Heat) and snow removal. The

    Gera Delavega KW Legacy Partners

    4 Elinor Rd, Old Saybrook, CT 06475
  • 254 Hidden Cove Rd, Old Saybrook, CT 06475

    $570,000

    Sold Feb 02, 2026

    254 Hidden Cove Rd, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 1,557 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Below List Price
    • $366/SF
    • 117 Days On Market

    Current Estimated Value $582,297

    Last Listing Agent Bob Yostos Coldwell Banker Realty

    254 Hidden Cove Rd, Old Saybrook, CT 06475
    • 118 Old Sea Ln, Old Saybrook, CT 06475

      Est $1,873,981

      Not Listed For Sale

      118 Old Sea Ln, Old Saybrook, CT 06475

      • 3 Beds
      • 3 Baths
      • 1,994 Sq Ft
      • Built 2020
      118 Old Sea Ln, Old Saybrook, CT 06475

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Nick Prevost William Raveis Real Estate

  • /3

    $695,000

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

    1333A Boston Post Rd, Old Saybrook, CT 06475

    An exceptional opportunity - Nestled on 1.16 acres of vacant land with public water access, this prime property is located in the sought-after Gateway Business B-4 District In an area of national tenants, boasting a daily traffic count of 15,900. This versatile lot is zoned for a variety of uses such as retail stores, professional offices, medical clinics, theaters, and more. Its strategic

    Ron Lyman Lyman Real Estate Brokerage & Development

    1333A Boston Post Rd, Old Saybrook, CT 06475
  • /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
  • 60 Ingham Hill Rd, Old Saybrook, CT 06475

    $685,000

    Sold Jul 23, 2026

    60 Ingham Hill Rd, Old Saybrook, CT 06475

    • Land
    • 8.11 Acres
    • $84,464 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 310 Days On Market

    Current Estimated Value $201,672

    Last Listing Agent Matt Diamond Houlihan Lawrence WD

    60 Ingham Hill Rd, Old Saybrook, CT 06475
  • /40

    $849,900

    • 4 Beds
    • 3 Baths
    • 2,496 Sq Ft

    3 Anchorage Ln, Old Saybrook, CT 06475

    Life by the water starts here at 3 Anchorage Ln, a spacious Colonial in Old Saybrook set beside the marina with deeded 10-foot access for convenient boat loading and unloading. This 4-bedroom, 3 full bath home offers 2,496 sqft designed for everyday comfort and coastal living. The beautifully remodeled kitchen is the true anchor of the home, ideal for gatherings and seamlessly connected to the

    Arek Wtulich William Raveis Real Estate

    3 Anchorage Ln, Old Saybrook, CT 06475
  • /39

    $4,100 Per Month

    • 4 Beds
    • 2 Baths
    • 2,772 Sq Ft
    • House for Rent

    18 Mohican Trail, Old Saybrook, CT 06475

    This quintessential beach house is available for academic rental from Sept. 15 to May 15. Enjoy coastal living in this beautifully remodeled home at sought-after Indian Town Beach in Old Saybrook. This spacious home offers the perfect blend of comfort, style, and stunning water views. The home features a thoughtfully updated interior with modern finishes, an open and inviting floor plan, and

    Joanne Breen ERA Hart Sargis-Breen

    18 Mohican Trail, Old Saybrook, CT 06475
  • 10 Cricket Ct, Old Saybrook, CT 06475

    $941,500

    Sold Jan 22, 2026

    10 Cricket Ct, Old Saybrook, CT 06475

    • 3 Beds
    • 1.5 Baths
    • 1,740 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Above List Price
    • $541/SF
    • 24 Days On Market

    Current Estimated Value $948,789

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    10 Cricket Ct, Old Saybrook, CT 06475
  • /37

    $725,000

    Coming Soon
    • 4 Beds
    • 1.5 Baths
    • 1,088 Sq Ft

    27 Gates Rd, Old Saybrook, CT 06475

    Rare opportunity to own a classic Connecticut shoreline beach cottage in the highly sought-after Cornfield Point Beach Association. Located just three homes from the water, this seasonal cottage offers water views from the enclosed breezeway and captures the timeless charm of Old Saybrook coastal living. Original hardwood floors, knotty pine walls, authentic beadboard, oversized rooms, and a

    Jennifer Gurnell William Raveis Real Estate

    27 Gates Rd, Old Saybrook, CT 06475
  • /21

    $4,500 Plus Fees

    • 3 Beds
    • 2 Baths
    • 1,358 Sq Ft
    • House for Rent

    28 Beach Rd E, Old Saybrook, CT 06475

    Amazing views every day at 28 Beach Rd West, Old Saybrook! This beautiful Academic Rental beach home has 3 bedrooms and 2 baths and is 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

    28 Beach Rd E, Old Saybrook, CT 06475
  • 95 Middletown Ave, Old Saybrook, CT 06475

    $1,049,900

    Sold Jul 30, 2026

    95 Middletown Ave, Old Saybrook, CT 06475

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1926

    Last Sold Summary

    • 5% Below List Price
    • $670/SF
    • 70 Days On Market

    Current Estimated Value $1,017,325

    Last Listing Agent Tracy Molloy Coldwell Banker Realty

    95 Middletown Ave, Old Saybrook, CT 06475
    • 509 Main St Unit 6, Old Saybrook, CT 06475

      Est $798,482

      Not Listed For Sale

      509 Main St Unit 6, Old Saybrook, CT 06475

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft
      • Built 2011
      509 Main St Unit 6, Old Saybrook, CT 06475

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Jake Pulcini Chiarito Real Estate LLC

  • /13

    $12,000,000

    • Land
    • 20.21 Acres
    • $593,765 per Acre

    1405-1445 Boston Post Rd, Old Saybrook, CT 06475

    Bushnell Farm presents a rare opportunity to acquire one of the Connecticut shoreline's most unique and historically significant properties. Located on Boston Post Road in Old Saybrook, this 20.21-acre property offers an exceptional combination of history, character, visibility, and development potential. The property features open meadows, mature trees, historic New England stone walls, and the

    Casey Fisher Houlihan Lawrence WD

    1405-1445 Boston Post Rd, Old Saybrook, CT 06475
  • /15

    $5,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,520 Sq Ft
    • House for Rent

    17 Mallard Dr, Old Saybrook, CT 06475

    This beautifully refreshed 2,520 square foot gambrel colonial is set on a private cul-de-sac in desirable Old Saybrook and comes fully furnished for effortless living. The home features four bedrooms and two and a half bathrooms, along with recent updates including fresh paint, updated bathrooms and new kitchen appliances. Both the sitting room and living room offer scenic views of tall grasses

    Hilary Reid Coldwell Banker Realty

    17 Mallard Dr, Old Saybrook, CT 06475
  • 175 Ferry Rd Unit 3, Old Saybrook, CT 06475

    $565,000

    Sold Jan 09, 2026

    175 Ferry Rd Unit 3, Old Saybrook, CT 06475

    • 2 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $338/SF
    • 77 Days On Market

    Current Estimated Value $599,803

    Last Listing Agent Kathy Schellens William Pitt Sotheby's Int'l

    175 Ferry Rd Unit 3, Old Saybrook, CT 06475
  • /40

    $949,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 1,208 Sq Ft

    28 Gates Rd, Old Saybrook, CT 06475

    Welcome to 28 Gates Road, a charming seasonal retreat in the heart of Cornfield Point Beach Association, one of Old Saybrook's most cherished beach communities. C/A and heating! With picturesque water views, beautifully manicured landscaping, and iconic green awnings, this classic cottage offers timeless shoreline charm and standout curb appeal. The spacious enclosed front porch is the heart of

    Jessica Keating William Raveis Real Estate

    28 Gates Rd, Old Saybrook, CT 06475
  • /12

    $2,400 Plus Fees

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • House for Rent

    38 Seabreeze Rd, Old Saybrook, CT 06475

    Welcome to your new home in Old Saybrook, CT! This charming Academic rental property is ideally located, providing easy access to a fantastic local restaurant and several department stores, ensuring you're never far from convenience and great dining experiences.This property offers the perfect balance of comfort and functionality, featuring both central heating and air conditioning,

    38 Seabreeze Rd, Old Saybrook, CT 06475
  • 11 Coulter St Unit 28, Old Saybrook, CT 06475

    $650,000

    Sold Mar 16, 2026

    11 Coulter St Unit 28, Old Saybrook, CT 06475

    • 2 Beds
    • 2.5 Baths
    • 2,099 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $310/SF
    • 5 Days On Market

    Current Estimated Value $657,733

    Last Listing Agent Christine Fappiano Shoreline Real Estate Company

    11 Coulter St Unit 28, Old Saybrook, CT 06475

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$722,500
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$590,000
Median 2 Bedroom Sale Price
$675,000
Median 1 Bedroom Sale Price
$379,000
Average Price Per Sq Ft
$564
Number of Homes for Sale
40
Last 12 months Home Sales
145
Months of Supply
3.30
Median List Price
$795,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home