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Old Saybrook, CT Homes for Sale

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  • 25 River Ave, Old Saybrook, CT 06475
    25 River Ave, Old Saybrook, CT 06475
    25 River Ave, Old Saybrook, CT 06475
    /38

    $800,000

    Open Sun 12PM - 3PM
    • 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
  • 2 Captains Ln, Old Saybrook, CT 06475
    2 Captains Ln, Old Saybrook, CT 06475
    2 Captains Ln, Old Saybrook, CT 06475
    /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
  • 1333A Boston Post Rd, Old Saybrook, CT 06475
    1333A Boston Post Rd, Old Saybrook, CT 06475
    1333A Boston Post Rd, 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
  • 3 Anchorage Ln, Old Saybrook, CT 06475
    3 Anchorage Ln, Old Saybrook, CT 06475
    3 Anchorage Ln, Old Saybrook, CT 06475
    /40

    $849,900

    Open Sun 11AM - 1PM
    • 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
  • 1405-1445 Boston Post Rd, Old Saybrook, CT 06475
    1405-1445 Boston Post Rd, Old Saybrook, CT 06475
    1405-1445 Boston Post Rd, 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
  • 28 Gates Rd, Old Saybrook, CT 06475
    28 Gates Rd, Old Saybrook, CT 06475
    28 Gates Rd, Old Saybrook, CT 06475
    /40

    $949,000

    Open Sun 1PM - 3PM
    • 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
  • 2 Pheasant Hill Ln, Old Saybrook, CT 06475
    2 Pheasant Hill Ln, Old Saybrook, CT 06475
    2 Pheasant Hill Ln, Old Saybrook, CT 06475
    /40

    $759,900

    • 4 Beds
    • 3 Baths
    • 2,474 Sq Ft

    2 Pheasant Hill Ln, Old Saybrook, CT 06475

    Gracious 4 bedroom/ three full baths Cape Cod with an attached two-car garage. Set on a picturesque, one-acre lightly wooded, corner lot with beautiful stone walls, mature plantings, gardens, large patio and an oversized L-shaped in-ground pool which becomes the centerpiece for summer enjoyment complete with lots of privacy. With approximately 2500 square feet of thoughtfully designed living

    Lisa Genovali Re/Max Valley Shore

    2 Pheasant Hill Ln, Old Saybrook, CT 06475
  • 9 Farview Ave, Old Saybrook, CT 06475
    9 Farview Ave, Old Saybrook, CT 06475
    9 Farview Ave, Old Saybrook, CT 06475
    /22

    $526,250

    $113K 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
  • 9 Old Colony Rd, Old Saybrook, CT 06475
    9 Old Colony Rd, Old Saybrook, CT 06475
    9 Old Colony Rd, Old Saybrook, CT 06475
    /5

    $725,000

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    9 Old Colony Rd, Old Saybrook, CT 06475

    Rare opportunity to create your dream home in one of Old Saybrook's most sought-after beach communities! Located across from Cornfield Point Beach Association, with deeded beach rights, this .23-acre property includes access to the beautiful sandy beach a short walk away making daily walks to the shoreline effortless. Surrounded by attractive homes, the setting alone makes this a standout

    Joel Lucas Coldwell Banker Realty

    9 Old Colony Rd, Old Saybrook, CT 06475
  • 21 Fenbrook Rd, Old Saybrook, CT 06475
    21 Fenbrook Rd, Old Saybrook, CT 06475
    21 Fenbrook Rd, Old Saybrook, CT 06475
    /31

    $1,440,000

    $150K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    21 Fenbrook Rd, Old Saybrook, CT 06475

    Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first

    Ralph Harvey ListWithFreedom.com

    21 Fenbrook Rd, Old Saybrook, CT 06475
  • 104 Knollwood Dr, Old Saybrook, CT 06475
    104 Knollwood Dr, Old Saybrook, CT 06475
    104 Knollwood Dr, Old Saybrook, CT 06475
    /37

    $1,595,000

    $105K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    104 Knollwood Dr, Old Saybrook, CT 06475

    True tranquility awaits at this waterfront oasis! Unparalleled water views from every vantage point! Privately set on a generous 0.37-acre lot, this 3-bedroom home provides direct water access- perfect for kayaking out to Long Island Sound right from your backyard. Inside, the home blends charm and character with thoughtful updates. Its architectural lines evoke a Normandy chalet vibe, while the

    Karen Lee Coldwell Banker Realty

    104 Knollwood Dr, Old Saybrook, CT 06475
  • 28 Church St, Old Saybrook, CT 06475
    28 Church St, Old Saybrook, CT 06475
    28 Church St, Old Saybrook, CT 06475
    /13

    $600,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    28 Church St, Old Saybrook, CT 06475

    This well-maintained 2-bedroom, 1-bathroom ranch is the ultimate turnkey opportunity in one of Connecticut's most beloved shoreline communities. Offered fully furnished - just move right in! Enjoy easy single-level living with a comfortable layout, all within minutes of Old Saybrook's downtown, local beaches, the Connecticut River, marinas, and charming shops and restaurants. Don't miss your

    Timothy Johnson Starr Team at LPT Realty

    28 Church St, Old Saybrook, CT 06475
  • 17 College St, Old Saybrook, CT 06475
    17 College St, Old Saybrook, CT 06475
    17 College St, Old Saybrook, CT 06475
    /40

    $1,140,000

    Open Sun 12PM - 3PM $59K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,960 Sq Ft

    17 College St, Old Saybrook, CT 06475

    Discover the perfect blend of comfort, style, and convenience in this beautifully remodeled home. Tucked in a prime location just minutes from fine dining, shopping, the golf course, and the train station, this property offers unparalleled access to everything you need. Walking along the shore to Saybrook Point Inn and Saybrook Lighthouse. Step into the heart of the home: a chef's kitchen with

    Deborah Pach Compass Connecticut, LLC

    17 College St, Old Saybrook, CT 06475
  • 11 Cambridge Ct E, Old Saybrook, CT 06475
    11 Cambridge Ct E, Old Saybrook, CT 06475
    11 Cambridge Ct E, Old Saybrook, CT 06475
    /28

    $1,695,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 2,178 Sq Ft

    11 Cambridge Ct E, Old Saybrook, CT 06475

    SHORELINE RETREAT - OLD SAYBROOK. Tucked away at the end of a quiet cul-de-sac with sweeping salt marsh and water views, this gracefully updated coastal haven offers exceptional privacy, natural beauty, and resort-style outdoor living in the heart of Old Saybrook. Set on a 1.6-acre lot and filled with natural light, the home features panoramic windows, open living and dining spaces, refinished

    Linda Coyle William Raveis Real Estate

    11 Cambridge Ct E, Old Saybrook, CT 06475
  • 13 Cove St, Old Saybrook, CT 06475
    13 Cove St, Old Saybrook, CT 06475
    13 Cove St, Old Saybrook, CT 06475
    /32

    $775,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    13 Cove St, Old Saybrook, CT 06475

    Saybrook Point! Welcome to the coastal lifestyle you've been dreaming of! This fully renovated coastal retreat with partial water views offers an exceptional blend of privacy, charm and effortless lifestyle. Steps aways from desired Saybrook Point, marinas, mini golf, Fenwick Golf Course and a stroll to beaches, restaurants and Main Street - everything that defines the Old Saybrook lifestyle is

    Sharon Linder Berkshire Hathaway NE Prop.

    13 Cove St, Old Saybrook, CT 06475
  • 11 River Edge Rd, Old Saybrook, CT 06475
    11 River Edge Rd, Old Saybrook, CT 06475
    11 River Edge Rd, Old Saybrook, CT 06475
    /40

    $6,600,000

    • 6 Beds
    • 4 Baths
    • 5,739 Sq Ft

    11 River Edge Rd, Old Saybrook, CT 06475

    Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 7,239 square feet, including 1,500 finished square feet on the lower level including an ensuite bedroom and recreational room with French doors opening

    Colette Harron William Pitt Sotheby's Int'l

    11 River Edge Rd, Old Saybrook, CT 06475
  • 41 Watrous Point Rd, Old Saybrook, CT 06475
    41 Watrous Point Rd, Old Saybrook, CT 06475
    41 Watrous Point Rd, Old Saybrook, CT 06475
    /40

    $3,995,000

    • 6 Beds
    • 4.5 Baths
    • 5,536 Sq Ft

    41 Watrous Point Rd, Old Saybrook, CT 06475

    Discover one of the most coveted vantage points on the lower Connecticut River-a mid-century modern sanctuary perched on a private 2.7-acre waterfront peninsula where land, river, and sky converge in perfect harmony. With an extraordinary 875 feet of water frontage embracing both the Connecticut River and the pristine Turtle Creek nature preserve, this property is a haven for bird enthusiasts and

    Teri Lewis William Pitt Sotheby's Int'l

    41 Watrous Point Rd, Old Saybrook, CT 06475
  • 53 Chalker Beach Rd, Old Saybrook, CT 06475
    53 Chalker Beach Rd, Old Saybrook, CT 06475
    53 Chalker Beach Rd, Old Saybrook, CT 06475
    /24

    $549,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    53 Chalker Beach Rd, Old Saybrook, CT 06475

    For the first time in generations this loved 3-bedroom ranch is available. It rests on a gentle knoll in the heart of the Chalker Beach community. Home has a full dry basement offering additional space for storage. One floor living, public water, central air, gleaming hardwood flooring throughout, sun filled bay windows, garden shed, open sunny lot, and new high efficiency propane furnace.

    Heather Clinton Berkshire Hathaway NE Prop.

    53 Chalker Beach Rd, Old Saybrook, CT 06475
  • 26 Willard Ave, Old Saybrook, CT 06475
    26 Willard Ave, Old Saybrook, CT 06475
    26 Willard Ave, Old Saybrook, CT 06475
    /40

    $1,295,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,904 Sq Ft

    26 Willard Ave, Old Saybrook, CT 06475

    Welcome to shoreline living at its finest in one of Old Saybrook's desirable beach communities, just minutes from the water, marinas, beaches, restaurants, and all that the Connecticut shoreline has to offer. This beautifully remodeled split-level ranch combines modern updates, flexible living space, and an exceptional outdoor setting. Step inside to an inviting open-concept floor plan filled

    Gigi Giordano Taylor Compass Connecticut, LLC

    26 Willard Ave, Old Saybrook, CT 06475
  • 22 Beaver Dam Trail, Old Saybrook, CT 06475
    22 Beaver Dam Trail, Old Saybrook, CT 06475
    22 Beaver Dam Trail, Old Saybrook, CT 06475
    /32

    $690,000

    • 4 Beds
    • 2.5 Baths
    • 1,934 Sq Ft

    22 Beaver Dam Trail, Old Saybrook, CT 06475

    Welcome to this classic home with a picturesque setting that is on a generous, level lot, the expansive backyard provides the perfect setting for outdoor entertaining, family gatherings, gardening, or simply relaxing and enjoying the outdoors. The backyard abuts the Old Saybrook preserve offering a private wooded backdrop with access to walking and hiking trails - an ideal setting! This home

    Sharon Linder Berkshire Hathaway NE Prop.

    22 Beaver Dam Trail, 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

    Open Sun 11AM - 1PM $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
  • 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
    /38

    $1,499,000

    New Construction
    • 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
  • 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
  • 96 Ayers Point Rd, Old Saybrook, CT 06475
    96 Ayers Point Rd, Old Saybrook, CT 06475
    96 Ayers Point Rd, Old Saybrook, CT 06475
    /40

    $1,163,000

    Open Sun 11:30AM - 1PM
    • 4 Beds
    • 3 Baths
    • 4,109 Sq Ft

    96 Ayers Point Rd, Old Saybrook, CT 06475

    Experience the best of Old Saybrook shoreline living at 96 Ayers Point Road. This exceptional 4/5-bedroom coastal home offers panoramic marsh and Connecticut River views from a private setting with no flood insurance required. Recently painted and designed for effortless indoor-outdoor living, the home features an in-ground gunite pool, an expansive wraparound deck, walls of glass and oversized

    Jennifer Gurnell William Raveis Real Estate

    96 Ayers Point Rd, 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
  • 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

    • 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
  • 34 Briarcliffe Trail, Old Saybrook, CT 06475
    34 Briarcliffe Trail, Old Saybrook, CT 06475
    34 Briarcliffe Trail, Old Saybrook, CT 06475
    /40

    $999,900

    Open Sun 11AM - 1PM $225K PRICE DROP
    • 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
  • 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

    $415,000

    $34K 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
  • 12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    12 Rocky Point Rd, Old Saybrook, CT 06475
    /38

    $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
  • 108 Maple Ave, Old Saybrook, CT 06475
    108 Maple Ave, Old Saybrook, CT 06475
    108 Maple Ave, Old Saybrook, CT 06475
    /39

    $2,200,000

    • 4 Beds
    • 4 Baths
    • 3,188 Sq Ft

    108 Maple Ave, Old Saybrook, CT 06475

    Contemporary coastal elegance meets exceptional privacy along South Cove in Old Saybrook. Set on an extraordinary 1.8-acre parcel, this cedar-sided, 3,188-square-foot residence offers breathtaking water views from nearly every room and a setting that is virtually impossible to recreate. Originally built in 1965 and thoughtfully rebuilt in 1991, the home was designed to capture its spectacular

    Jessica Blancato William Pitt Sotheby's Int'l

    108 Maple Ave, Old Saybrook, CT 06475
  • 5 Woodland Dr, Old Saybrook, CT 06475
    5 Woodland Dr, Old Saybrook, CT 06475
    5 Woodland Dr, Old Saybrook, CT 06475
    /40

    $1,590,000

    Open Sun 11AM - 1PM $200K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,125 Sq Ft

    5 Woodland Dr, Old Saybrook, CT 06475

    Rare opportunity to enjoy sweeping views of Long Island Sound from a quiet street just off Maple Avenue in sought-after Knollwood Beach. This beautifully renovated 3-bedroom, 3-bath coastal retreat, just one street from the water, offers unobstructed views and is ideal as a year-round home or second getaway. The bright, open floor plan is designed to capture the scenery, with an oversized

    Joel Lucas Coldwell Banker Realty

    5 Woodland Dr, Old Saybrook, CT 06475
  • 37 Woodland Dr, Old Saybrook, CT 06475
    37 Woodland Dr, Old Saybrook, CT 06475
    37 Woodland Dr, Old Saybrook, CT 06475
    /40

    $1,100,000

    Open Sun 9AM - 11AM
    • 3 Beds
    • 2 Baths
    • 1,426 Sq Ft

    37 Woodland Dr, Old Saybrook, CT 06475

    Experience coastal luxury in this stunning 3-bedroom, 2-bathroom ranch style home nestled in Knollwood Beach. Set on a rare .33 acre lot, it offers picturesque marsh and South Cove views. Step inside to discover a newly remodeled interior featuring an expansive remodeled white kitchen with quartz counters, large center island. The family room boasts a dramatic fireplace, while a sunlit dining

    Joel Lucas Coldwell Banker Realty

    37 Woodland Dr, Old Saybrook, CT 06475
  • 119 Great Hammock Rd, Old Saybrook, CT 06475
    119 Great Hammock Rd, Old Saybrook, CT 06475
    119 Great Hammock Rd, Old Saybrook, CT 06475
    /38

    $899,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    119 Great Hammock Rd, Old Saybrook, CT 06475

    Every Day a Getaway! Some properties ask you to choose between full-time living & vacation living. Not this one. Set in the heart of Old Saybrook, this fully furnished 7-room Cape Cod delivers the ease of a residence with the spirit of a seasonal retreat - and comes with a private guest house. The main home offers 3 bdrms,, 2 baths & includes a coveted 1st fl bdrm for single-level living. A large

    Pardi & Zucco Team William Pitt Sotheby's Int'l

    119 Great Hammock Rd, Old Saybrook, CT 06475
  • 256 Hidden Cove Rd, Old Saybrook, CT 06475
    256 Hidden Cove Rd, Old Saybrook, CT 06475
    256 Hidden Cove Rd, Old Saybrook, CT 06475
    /31

    $529,000

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

    256 Hidden Cove Rd, Old Saybrook, CT 06475

    Discover effortless shoreline living at Summerwood in Old Saybrook. This beautifully maintained 2-bedroom, 1.5-bath condominium offers 1,557 SqFt of light-filled living space with tranquil marsh views and an upper-level loft perfect for a home office, guest space, or reading retreat. The updated kitchen features granite countertops, stainless steel appliances, and a center island, while hardwood

    Carla Mousch William Raveis Real Estate

    256 Hidden Cove Rd, Old Saybrook, CT 06475
  • 1445 Boston Post Rd, Old Saybrook, CT 06475
    1445 Boston Post Rd, Old Saybrook, CT 06475
    1445 Boston Post Rd, Old Saybrook, CT 06475
    /12

    $12,000,000

    • 4 Beds
    • 1 Bath
    • 2,059 Sq Ft

    1445 Boston Post Rd, Old Saybrook, CT 06475

    A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a

    Casey Fisher Houlihan Lawrence WD

    1445 Boston Post Rd, Old Saybrook, CT 06475
  • 52 Chalker Beach Rd, Old Saybrook, CT 06475
    52 Chalker Beach Rd, Old Saybrook, CT 06475
    52 Chalker Beach Rd, Old Saybrook, CT 06475
    /32

    $699,000

    • 3 Beds
    • 1.5 Baths
    • 1,120 Sq Ft

    52 Chalker Beach Rd, Old Saybrook, CT 06475

    No stone was left unturned at this turn key beach house in the Chalker Beach Association! Completely and professionally renovated from bottom to top, this 3 bedroom cottage is open, light and airy and ready for you to move in, just in time for summer! A spacious living room opens into the lovely eat-in kitchen with custom cabinets, stainless steel appliances and beautiful crown moulding. A bright

    Tina Rupp William Pitt Sotheby's Int'l

    52 Chalker Beach Rd, Old Saybrook, CT 06475
  • 4 Beach Rd, Old Saybrook, CT 06475
    4 Beach Rd, Old Saybrook, CT 06475
    4 Beach Rd, Old Saybrook, CT 06475
    /38

    $1,790,000

    $200K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,745 Sq Ft

    4 Beach Rd, Old Saybrook, CT 06475

    DEEDED BEACH RIGHTS TO CORNFIELD POINT! One of Old Saybrook's most sought after beach communities! Enjoy beach days, sunset strolls, boating adventures, and the relaxed charm of shoreline living. This impeccably maintained home with breathtaking, expansive marsh views, features a spectacular, fully renovated chef's kitchen featuring premium appliances, Thermadore oven, a wine chiller, ice maker,

    Sharon Linder Berkshire Hathaway NE Prop.

    4 Beach Rd, Old Saybrook, CT 06475
  • 96 Chalker Beach Rd, Old Saybrook, CT 06475
    96 Chalker Beach Rd, Old Saybrook, CT 06475
    96 Chalker Beach Rd, Old Saybrook, CT 06475
    /33

    $649,900

    • 3 Beds
    • 1 Bath
    • 968 Sq Ft

    96 Chalker Beach Rd, Old Saybrook, CT 06475

    Welcome to your seasonal sanctuary at Chalker Beach, where sun-soaked days and starry nights create lasting memories. Offered fully furnished and thoughtfully styled with relaxed coastal charm, this seasonal cottage is the perfect place to slow down, unwind, and enjoy easy shoreline living. Just a short walk or golf cart ride to the beach, the home is tucked into one of the shoreline's most loved

    Danielle Spada Coldwell Banker Realty

    96 Chalker Beach Rd, Old Saybrook, CT 06475
  • 0 Middlesex Turnpike, Old Saybrook, CT 06475
    0 Middlesex Turnpike, Old Saybrook, CT 06475
    0 Middlesex Turnpike, Old Saybrook, CT 06475
    /7

    $495,000

    • Land
    • 32.66 Acres
    • $15,156 per Acre

    0 Middlesex Turnpike, Old Saybrook, CT 06475

    32.66 ac at a prime intersection in Old Saybrook right off I-95. W/ Plans for various layouts of multiple building to totaling as much as 50,000 sqft +/-. B4 Zone offers a wide variety of uses. A large portion of this parcel is wetlands.

    Craig Milton Re/Max Valley Shore

    0 Middlesex Turnpike, Old Saybrook, CT 06475
  • 14 Anchorage Ln, Old Saybrook, CT 06475
    14 Anchorage Ln, Old Saybrook, CT 06475
    14 Anchorage Ln, Old Saybrook, CT 06475
    /21

    $2,000,000

    • 4 Beds
    • 2 Baths
    • 1,776 Sq Ft

    14 Anchorage Ln, Old Saybrook, CT 06475

    This exceptional Cape Cod-style waterfront home has the perfect blend of luxury, comfort, and coastal charm. Nestled on a private canal off the CT River, the recently renovated open concept design features a dramatic vaulted Great Room with a wood-burning stove and expansive windows that fill the home with natural light. The gourmet eat-in kitchen is designed for both everyday living and

    Steven Koleno Beycome of Connecticut

    14 Anchorage Ln, Old Saybrook, CT 06475

Showing Results 1 - 40, Page 1 of 2

Connecticut Middlesex County Old Saybrook

Real Estate & Homes for Sale in Old Saybrook, CT

Why Live in Old Saybrook

Old Saybrook, Connecticut, is a tranquil town situated along the Long Island Sound, ideal for those seeking a waterside residence with ample beach and water activities. Housing options include colonials, ranch-style, and Cape Cod homes, with prices starting around $340,000 for single-family homes and peaking at $4.2 million for luxurious seaside properties. The town is known for its high foot traffic, especially near the beach and Main Street district. Old Saybrook Public Schools are highly rated, with Kathleen E. Goodwin Elementary School, Old Saybrook Middle School, and Old Saybrook High School all receiving commendable marks for academics and teacher quality. The town features several beautiful beaches, such as Cove Beach and Great Hammock, and recreational activities like golfing at Fenwick Golf Course. Dining options are concentrated along Route 1, with popular spots like the Parthenon Diner. The town hosts annual events, including holiday celebrations, a Fourth of July parade, and an art festival. Old Saybrook is accessible via Interstate 95, making it convenient for commuters. The town has a lower crime rate compared to the national average, contributing to its appeal as a safe place to live.

Learn more about living in Old Saybrook

Frequently Asked Questions

What is the average home price in Old Saybrook, CT?
Homes for sale in Old Saybrook, CT have an average home price of $1,137,729.
How many homes have sold over the last 12 months in Old Saybrook, CT?
148 homes have sold in Old Saybrook, CT over the last 12 months.
What is the average household income in Old Saybrook, CT?
The average household income in Old Saybrook, CT is $136K.
What are the most popular zip codes in Old Saybrook, CT?
The most popular zip codes in Old Saybrook, CT include 06475, 06498, 06371, 06426 and 06442.
How much do you need to make to afford a house in Old Saybrook?
The median home price in Old Saybrook is $799,000. If you put a 20% down payment of $159,800 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $4,040 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $173K a year to afford the median home price in Old Saybrook. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Old Saybrook is $136K.
How are the schools in Old Saybrook, CT?
Old Saybrook, CT has highly rated public and private schools. Some of the best schools in Old Saybrook based on Niche Grades are Oxford Academy, Lyme-Old Lyme High School and Lyme-Old Lyme Middle School. Browse all the schools in Old Saybrook, CT to learn more.

Home Prices in Old Saybrook, CT

The median home sale price in Old Saybrook, CT is $737,500, up 7% year-over-year. Homes in Old Saybrook sell in 62 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$737,500
Median Single Family Sale Price
$802,499
Median Townhouse Sale Price
$590,000
Median 2 Bedroom Sale Price
$660,000
Median 1 Bedroom Sale Price
$379,000
Average Price Per Sq Ft
$569
Number of Homes for Sale
45
Last 12 months Home Sales
148
Months of Supply
3.60
Median List Price
$799,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
7%
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