6,273

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
  • /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
  • 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 $679,015

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

    99 Maple Ave, Old Saybrook, CT 06475
  • /40

    $2,899,900

    Open Sat 12PM - 2PM
    • 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
  • /33

    Starting at $2,753

    Total Monthly Price

    • 1 - 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
  • 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 $1,355,564

    Last Listing Agent Jodi Serapilia Seaport Real Estate Services

    105 Fenwood Dr, Old Saybrook, CT 06475
  • /4

    $695,000

    $300K PRICE DROP
    • Land
    • 1.25 Acres
    • $556,000 per Acre

    1333A Boston Post Rd, Old Saybrook, CT 06475

    An exceptional opportunity - Nestled on 1.25 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
  • /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
  • 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 $580,994

    Last Listing Agent Lorenda DiMeo Century 21 AllPoints Realty

    143 Sandy Point Rd Unit 143, Old Saybrook, CT 06475
  • /23

    $699,500

    $100K PRICE DROP Pending
    • Land
    • 8.11 Acres
    • $86,252 per Acre

    60 Ingham Hill Rd, Old Saybrook, CT 06475

    Picturesque waterfront 8.1-acre lot on the tranquil Oyster River in historic Old Saybrook. 1,400 feet of river frontage leading to Long Island Sound. Currently set as farmland, this could be a home run for builders sensitive to the needs of the land. With its beauty, you have 50-plus feet of road frontage and large footprint within the 50-foot tidal wetlands setback. I-95 is easily accessible,

    Matt Diamond Houlihan Lawrence WD

    60 Ingham Hill Rd, Old Saybrook, CT 06475
  • /4

    $1,300 Per Month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • House for Rent

    1500 Boston Post Rd Unit 10, Old Saybrook, CT 06475

    Studio unit includes heat, hot water, electricity, cable, and internet. Recently remodeled. Clean and freshly painted. Private bath. Parking available. Conveniently located. Walking distance to beach.

    Brian Botti Botti Realty

    1500 Boston Post Rd Unit 10, 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 $1,075,102

    Last Listing Agent Nancy Mesham Coldwell Banker Realty

    10 Trolley Crossing, Old Saybrook, CT 06475
  • /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
  • /19

    $2,400 Per Month

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

    38 Seabreeze Rd, Old Saybrook, CT 06475

    This spectacular home with a fantastic location is an Academic Rental; from September 15, 2026 through May 15, 2027. Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with

    Terry McDonald McDonald Real Estate, LLC

    38 Seabreeze 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 $581,311

    Last Listing Agent Bob Yostos Coldwell Banker Realty

    254 Hidden Cove Rd, Old Saybrook, CT 06475
  • /40

    $1,049,900

    $50K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft

    95 Middletown Ave, Old Saybrook, CT 06475

    95 Middletown Avenue offers a rare opportunity to enjoy four season living in the heart of Saybrook Manor, one of Old Saybrook's most sought after shoreline communities. Renovated in 2022 with thoughtful attention to comfort and design, this beautifully updated home combines timeless coastal character with modern amenities and sweeping views of the Oyster River & Long Island Sound. With approx.

    Tracy Molloy Coldwell Banker Realty

    95 Middletown Ave, Old Saybrook, CT 06475
  • /31

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • House for Rent

    43 Pennywise Ln, Old Saybrook, CT 06475

    Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen

    Phoebe Schreiner William Pitt Sotheby's Int'l

    43 Pennywise Ln, 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 $933,050

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    10 Cricket Ct, Old Saybrook, CT 06475
  • /39

    $874,900

    • 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
  • /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
  • 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 $598,954

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

    175 Ferry Rd Unit 3, Old Saybrook, CT 06475
  • /25

    $419,900

    $30K PRICE DROP Under Contract
    • 4 Beds
    • 1 Bath
    • 640 Sq Ft

    39 Middletown Ave, Old Saybrook, CT 06475

    Charming and beautifully updated 4 bedroom partially furnished Seasonal Cottage in desireable Saybrook Manor beach community. This home offers the perfect blend of character and modern improvements with vaulted ceilings and exposed beams. The completely remodeled kitchen features Corian countertops, a classic farmhouse sink, skylight for natural light and matching rolling kitchen cart for added

    Tracy Pentalow Property Shoppe, LLC

    39 Middletown Ave, Old Saybrook, CT 06475
  • /23

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,137 Sq Ft
    • House for Rent

    8 Clinton Ave, Old Saybrook, CT 06475

    Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor

    Terry McDonald McDonald Real Estate, LLC

    8 Clinton Ave, 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 $659,141

    Last Listing Agent Christine Fappiano Shoreline Real Estate Company

    11 Coulter St Unit 28, Old Saybrook, CT 06475
  • /22

    $587,500

    $52K PRICE DROP
    • 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
  • /37

    $4,500 Per Month

    • 4 Beds
    • 3 Baths
    • 1,120 Sq Ft
    • House for Rent

    8 Belaire Manor, Old Saybrook, CT 06475

    Academic rental available October 1, 2026 - May 28, 2027. This beautiful beach home is a direct waterfront, 4 bedroom, one-level home situated on a deep soft-sand beach in a private association. Wake up every morning to ocean waves, and watch the panoramic sunrises and sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The large patio on

    Erika Raffles William Pitt Sotheby's Int'l

    8 Belaire Manor, Old Saybrook, CT 06475
  • 55 Woodland Dr, 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 $776,276

    Last Listing Agent Joel Lucas Coldwell Banker Realty

    55 Woodland Dr, Old Saybrook, CT 06475
  • /34

    $1,350,000

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

    96 Fenwood Dr, Old Saybrook, CT 06475

    Located on a corner lot in the District of Fenwood with views of the water, this house has all of the comforts of home. The spacious main level entry offers the living room, family room with a fireplace, formal dining room, full bath, and kitchen. The kitchen is complete with an island breakfast bar, and wet bar where the view of the cove is evident of the peaceful neighborhood. Upstairs are the

    Eric Porco 4 Corners Realty LLC

    96 Fenwood Dr, Old Saybrook, CT 06475
  • /34

    $2,175 Per Month

    • 1 Bath
    • 550 Sq Ft
    • House for Rent

    115 Ayers Point Rd, Old Saybrook, CT 06475

    YEAR ROUND UNFURNISHED STUDIO RENTAL located in the Ayers Point community with convenient access to I-95 and Route 9. This well maintained and updated studio has the added benefit of INCLUDED UTILITIES (WiFi and/or cable TV are not included in the rent) The main living space features a partial wall that provides separation between the sleeping and living area, creating an open feel while

    Kara Bell J.M. REALTY

    115 Ayers Point Rd, Old Saybrook, CT 06475
  • 355 Main St, 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 $748,378

    Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

    355 Main St, Old Saybrook, CT 06475

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$738,950
Median Single Family Sale Price
$804,999
Median Townhouse Sale Price
$505,000
Median 2 Bedroom Sale Price
$647,500
Median 1 Bedroom Sale Price
$377,000
Average Price Per Sq Ft
$572
Number of Homes for Sale
40
Last 12 months Home Sales
150
Months of Supply
3.20
Median List Price
$792,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
8%
How to Buy a Home How to Finance a Home How to Sell a Home