Moving to Old Saybrook CT | real estate for sale in Old Saybrook Connecticut | Property Statistics of living in Old Saybrook

Old Saybrook is one of Connecticut's most established shoreline communities, offering a mix of waterfront estates, beach cottages, condominiums, and year-round residences. The town's coastal location and historic significance contribute to strong market demand. Real estate values are heavily influenced by proximity to Long Island Sound and the Connecticut River. Limited shoreline inventory and continued demand for coastal properties support long-term appreciation and investment potential.

Current Real Estate Statistics for Homes in Old Saybrook CT as of Saturday, August 8, 2026
57 Active Homes Listed
52 Avg. DOM
$218 Avg. $ / Sq.Ft.
$549000 Med. List Price
7/31/2026 4:05:03 AM
Active
170 Old Post Road Old Saybrook CT
170 Old Post Road

Old Saybrook, Connecticut 06475

$1,200,000 | Active

3 Beds | 3 Baths | 2128 Sqft | 1 Acres | 0 Days on Market

Property Type: Single Family For Sale

Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-boa...

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7/30/2026 1:47:15 PM
Active
21 Fenbrook Road Old Saybrook CT
21 Fenbrook Road

Old Saybrook, Connecticut 06475

$1,375,000 | Active

3 Beds | 3 Baths | 1916 Sqft | 0.22 Acres | 86 Days on Market

Property Type: Single Family For Sale

Welcome to an exceptional year-round home located in one of Connecticuts 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 ...

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7/30/2026 4:05:02 AM
Active
207 School House Road Old Saybrook CT
207 School House Road

Old Saybrook, Connecticut 06475

$585,000 | Active

4 Beds | 2 Baths | 2149 Sqft | 1.1 Acres | 1 Days on Market

Property Type: Single Family For Sale

A rare opportunity awaits to become the second owner of this lovingly maintained ranch on desirable Schoolhouse Road. Thoughtfully designed for comfortable one-level living, this spacious 2,149-square-foot home offers four generously sized bedrooms, wide hallways, gleaming hardwo...

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7/29/2026 4:43:44 PM
Under Contract CTS
92 Bokum Road Old Saybrook CT
92 Bokum Road

Old Saybrook, Connecticut 06475

$559,000 | Under Contract - Continue

2 Beds | 2 Baths | 1376 Sqft | 1.71 Acres | 91 Days on Market

Property Type: Single Family For Sale

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 w...

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7/28/2026 9:10:44 PM
Active
96 Ayers Point Road Old Saybrook CT
96 Ayers Point Road

Old Saybrook, Connecticut 06475

$1,099,000 | Active

4 Beds | 3 Baths | 4109 Sqft | 1.14 Acres | 30 Days on Market

Property Type: Single Family For Sale

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-o...

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7/27/2026 10:02:09 PM
Under Contract
86 Fenwood Drive Old Saybrook CT
86 Fenwood Drive

Old Saybrook, Connecticut 06475

$874,900 | Under Contract

2 Beds | 3 Baths | 2209 Sqft | 0.3 Acres | 11 Days on Market

Property Type: Single Family For Sale

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...

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7/27/2026 9:14:39 PM
Under Contract CTS
14 Cedarwood Lane Old Saybrook CT
14 Cedarwood Lane

Old Saybrook, Connecticut 06475

$615,000 | Under Contract - Continue

3 Beds | 2 Baths | 1033 Sqft | 0.64 Acres | 33 Days on Market

Property Type: Single Family For Sale

NEW LOWERED PRICE! Welcome to your new shoreline home - a ranch-style retreat in the heart of Old Saybrook. This beautifully maintained 3-bedroom, 1 1/2-bathroom home offers a perfect blend of comfortable living and coastal New England lifestyle - all just approx. 1 mile from the...

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7/26/2026 3:58:03 PM
Active
9 Old Colony Road Old Saybrook CT
9 Old Colony Road

Old Saybrook, Connecticut 06475

$675,000 | Active

4 Beds | 2 Baths | 1344 Sqft | 0.23 Acres | 22 Days on Market

Property Type: Single Family For Sale

Rare opportunity to create your dream home in one of Old Saybrooks 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 da...

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7/26/2026 2:10:10 AM
Under Contract CTS
2 Half Penny Lane Old Saybrook CT
2 Half Penny Lane

Old Saybrook, Connecticut 06475

$575,000 | Under Contract - Continue

3 Beds | 2 Baths | 1800 Sqft | 1 Acres | 7 Days on Market

Property Type: Single Family For Sale

This charming home offers the perfect blend of charm, comfort, and opportunity. Filled with warmth, character, and endless potential, this well-maintained home features one bedroom and a full bath on the main level and 3 additional bedrooms upstairs. An inviting open floor plan w...

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7/24/2026 4:48:04 PM
Under Contract CTS
61 Ingham Hill Road Old Saybrook CT
61 Ingham Hill Road

Old Saybrook, Connecticut 06475

$415,000 | Under Contract - Continue

1 Beds | 2 Baths | 1205 Sqft | 0.39 Acres | 89 Days on Market

Property Type: Single Family For Sale

Step into the charm of this delightful 1920 year-round bungalow, just a stones throw from Old Saybrooks stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, youll find a spacious area that offers endless possi...

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7/24/2026 1:41:02 AM
Coming Soon
84 Ayers Point Road Old Saybrook CT
84 Ayers Point Road

Old Saybrook, Connecticut 06475

$675,000 | Coming Soon

3 Beds | 2 Baths | 1788 Sqft | 1.14 Acres | Days on Market

Property Type: Single Family For Sale

Located in the highly sought-after shoreline town of Old Saybrook, this charming Cape offers character, comfort, and exceptional curb appeal. Set on 1.14 beautiful acres in the desirable Otter Cove neighborhood, this well-maintained three-bedroom, two-bath home is ready for its n...

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7/23/2026 11:32:32 PM
Active
25 Uncas Trail Old Saybrook CT
25 Uncas Trail

Old Saybrook, Connecticut 06475

$799,900 | Active

2 Beds | 2 Baths | 1760 Sqft | 0.11 Acres | 18 Days on Market

Property Type: Single Family For Sale

Welcome to the desirable Indiantown Beach community, where endless possibilities await. This well-loved home offers a spacious floor plan featuring a bright sunroom, generous family room with a floor-to-ceiling gas fireplace and built-ins, and a large primary suite with its full ...

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7/23/2026 7:38:30 PM
Under Contract CTS
420 Maple Avenue Old Saybrook CT
420 Maple Avenue

Old Saybrook, Connecticut 06475

$1,950,000 | Under Contract - Continue

3 Beds | 3 Baths | 1900 Sqft | 0.25 Acres | 12 Days on Market

Property Type: Single Family For Sale

Welcome to a coastal sanctuary where changing, panoramic views of the Long Island Sound greet you from almost every room. Situated directly across from the shore with no homes across the street to block your view, this remarkable year-round residence offers a permanent, front-row...

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7/23/2026 4:28:39 PM
Active
37 Woodland Drive Old Saybrook CT
37 Woodland Drive

Old Saybrook, Connecticut 06475

$1,075,000 | Active

3 Beds | 2 Baths | 1426 Sqft | 0.33 Acres | 37 Days on Market

Property Type: Single Family For Sale

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 ki...

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7/23/2026 2:09:24 PM
Under Contract
8 Owaneco Trail Old Saybrook CT
8 Owaneco Trail

Old Saybrook, Connecticut 06475

$2,195,000 | Under Contract

4 Beds | 4 Baths | 2881 Sqft | 0.46 Acres | 9 Days on Market

Property Type: Single Family For Sale

Welcome to this stunning gray shingle, Nantucket-style Cape Cod nestled in the sought-after Indiantown neighborhood of Old Saybrook - less than a quarter mile to the beach and a Private Marina! Offering over 2,800 square feet of beautifully appointed living space, this exceptiona...

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7/23/2026 12:38:48 AM
Under Contract CTS
9 Farview Avenue Old Saybrook CT
9 Farview Avenue

Old Saybrook, Connecticut 06475

$526,250 | Under Contract - Continue

3 Beds | 1 Baths | 1038 Sqft | 0.24 Acres | 44 Days on Market

Property Type: Single Family For Sale

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 b...

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7/22/2026 8:59:32 PM
Under Contract CTS
6 Watch Hill Road Old Saybrook CT
6 Watch Hill Road

Old Saybrook, Connecticut 06475

$460,000 | Under Contract - Continue

3 Beds | 3 Baths | 2830 Sqft | 0.94 Acres | 91 Days on Market

Property Type: Single Family For Sale

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...

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7/21/2026 1:02:38 PM
Under Contract CTS
4 Beach Road Old Saybrook CT
4 Beach Road

Old Saybrook, Connecticut 06475

$1,425,000 | Under Contract - Continue

3 Beds | 3 Baths | 3745 Sqft | 3.42 Acres | 57 Days on Market

Property Type: Single Family For Sale

DEEDED BEACH RIGHTS TO CORNFIELD POINT! One of Old Saybrooks most sought after beach communities! Enjoy beach days, sunset strolls, and the relaxed charm of shoreline living. This impeccably maintained Nantucket-style reverse floor plan home promotes scenic views from upper level...

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7/21/2026 12:15:30 PM
Under Contract
21 Baum Avenue Old Saybrook CT
21 Baum Avenue

Old Saybrook, Connecticut 06475

$584,900 | Under Contract

2 Beds | 2 Baths | 1290 Sqft | 0.25 Acres | 4 Days on Market

Property Type: Single Family For Sale

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 w...

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7/20/2026 6:43:14 PM
Active
17 College Street Old Saybrook CT
17 College Street

Old Saybrook, Connecticut 06475

$1,099,000 | Active

3 Beds | 3 Baths | 1960 Sqft | 0.48 Acres | 131 Days on Market

Property Type: Single Family For Sale

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 ...

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7/20/2026 12:25:02 AM
Under Contract CTS
22 Beaver Dam Trail Old Saybrook CT
22 Beaver Dam Trail

Old Saybrook, Connecticut 06475

$599,000 | Under Contract - Continue

4 Beds | 3 Baths | 1934 Sqft | 1.04 Acres | 27 Days on Market

Property Type: Single Family For Sale

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 ...

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7/17/2026 7:07:25 PM
Active
26 Willard Avenue Old Saybrook CT
26 Willard Avenue

Old Saybrook, Connecticut 06475

$1,269,000 | Active

3 Beds | 2 Baths | 2904 Sqft | 0.51 Acres | 42 Days on Market

Property Type: Single Family For Sale

Welcome to shoreline living at its finest in one of Old Saybrooks 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, fl...

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7/16/2026 4:05:03 AM
Active
65 Knollwood Drive Old Saybrook CT
65 Knollwood Drive

Old Saybrook, Connecticut 06475

$1,100,000 | Active

3 Beds | 3 Baths | 2153 Sqft | 0.9 Acres | 15 Days on Market

Property Type: Single Family For Sale

The best of both worlds-enjoy the tranquility of a peaceful setting while being just a short stroll to the beach. Beautifully updated and impeccably maintained, this year-round home offers the perfect blend of coastal charm and modern comfort. A welcoming front porch invites you ...

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7/16/2026 4:05:02 AM
Active
14 Seagull Road Old Saybrook CT
14 Seagull Road

Old Saybrook, Connecticut 06475

$775,000 | Active

4 Beds | 2 Baths | 1675 Sqft | 0.1 Acres | 15 Days on Market

Property Type: Single Family For Sale

Welcome to 14 Seagull Road, where the best of Connecticut shoreline living begins just outside your front door. Tucked within the sought-after Knollwood Beach community, this updated cape is just a 3-minute walk to the ocean. Enjoy waterfront strolls, kayaking, swimming, pickleba...

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7/16/2026 12:26:46 AM
Under Contract CTS
5 Cove Landing Old Saybrook CT
5 Cove Landing

Old Saybrook, Connecticut 06475

$1,649,000 | Under Contract - Continue

3 Beds | 3 Baths | 2787 Sqft | 0.47 Acres | 21 Days on Market

Property Type: Single Family For Sale

Nestled within an enclave of distinguished homes in the heart of Old Saybrook, this exceptional residence captures sweeping water views and breathtaking morning sunrises, offering a rare blend of sophistication, and timeless coastal charm. From the moment you enter this light fil...

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7/15/2026 9:14:34 PM
Active
108 Maple Avenue Old Saybrook CT
108 Maple Avenue

Old Saybrook, Connecticut 06475

$1,850,000 | Active

4 Beds | 4 Baths | 3188 Sqft | 1.8 Acres | 42 Days on Market

Property Type: Single Family For Sale

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 re...

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7/15/2026 3:36:32 PM
Under Contract
43 Indianola Drive Old Saybrook CT
43 Indianola Drive

Old Saybrook, Connecticut 06475

$1,695,000 | Under Contract

3 Beds | 3 Baths | 2978 Sqft | 0.48 Acres | 5 Days on Market

Property Type: Single Family For Sale

Enjoy coastal living at its finest in the coveted Cornfield Point community. This custom-built home offers nearly 3,000 square feet of thoughtfully designed space, featuring 4 bedrooms, 3 full baths, and a versatile main-level office, den, or media room to suit your lifestyle. St...

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7/15/2026 3:39:56 AM
Under Contract
28 Bellaire Drive Old Saybrook CT
28 Bellaire Drive

Old Saybrook, Connecticut 06475

$850,000 | Under Contract

3 Beds | 2 Baths | 1175 Sqft | 0.15 Acres | 7 Days on Market

Property Type: Single Family For Sale

Welcome to the highly sought-after Cornfield Point Beach Association, where coastal charm meets effortless year-round living. This beautifully maintained cottage-style ranch offers the perfect seaside retreat for those seeking an upscale second home or an easy-to-maintain retirem...

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7/14/2026 6:44:27 PM
Under Contract CTS
41 Watrous Point Road Old Saybrook CT
41 Watrous Point Road

Old Saybrook, Connecticut 06475

$3,995,000 | Under Contract - Continue

6 Beds | 5 Baths | 5536 Sqft | 2.7 Acres | 122 Days on Market

Property Type: Single Family For Sale

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...

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7/12/2026 6:33:31 PM
Under Contract CTS
2 Pheasant Hill Lane Old Saybrook CT
2 Pheasant Hill Lane

Old Saybrook, Connecticut 06475

$759,900 | Under Contract - Continue

4 Beds | 3 Baths | 2474 Sqft | 1 Acres | 29 Days on Market

Property Type: Single Family For Sale

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 s...

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7/11/2026 4:05:02 AM
Active
119 Great Hammock Road Old Saybrook CT
119 Great Hammock Road

Old Saybrook, Connecticut 06475

$899,000 | Active

3 Beds | 2 Baths | 1834 Sqft | 0.23 Acres | 20 Days on Market

Property Type: Single Family For Sale

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 privat...

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7/10/2026 4:05:02 AM
Active
81 Hartford Avenue Old Saybrook CT
81 Hartford Avenue

Old Saybrook, Connecticut 06475

$2,295,000 | Active

4 Beds | 2 Baths | 2440 Sqft | 0.33 Acres | 21 Days on Market

Property Type: Single Family For Sale

Experience the pinnacle of Connecticut shoreline living in this exquisitely remodeled coastal retreat, ideally located just three homes from the private association beach in the Saybrook Manor Beach community. Blending timeless coastal elegance with todays most desirable amenitie...

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7/9/2026 4:05:02 AM
Active
3 Anchorage Lane Old Saybrook CT
3 Anchorage Lane

Old Saybrook, Connecticut 06475

$849,900 | Active

4 Beds | 3 Baths | 2496 Sqft | 0.25 Acres | 22 Days on Market

Property Type: Single Family For Sale

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. Th...

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7/9/2026 4:05:02 AM
Active
28 Gates Road Old Saybrook CT
28 Gates Road

Old Saybrook, Connecticut 06475

$949,000 | Active

4 Beds | 2 Baths | 1208 Sqft | 0.09 Acres | 22 Days on Market

Property Type: Single Family For Sale

Welcome to 28 Gates Road, a charming seasonal retreat in the heart of Cornfield Point Beach Association, one of Old Saybrooks most cherished beach communities. C/A and heating! With picturesque water views, beautifully manicured landscaping, and iconic green awnings, this classic...

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7/7/2026 6:51:33 PM
Under Contract
96 Fenwood Drive Old Saybrook CT
96 Fenwood Drive

Old Saybrook, Connecticut 06475

$1,250,000 | Under Contract

3 Beds | 3 Baths | 2326 Sqft | 0.23 Acres | 99 Days on Market

Property Type: Single Family For Sale

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 entire house has been refitted with all new heating and air conditioning. The spacious main level entry offers the living room, family room with a fireplace...

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7/6/2026 4:05:02 AM
Active
15 Baum Avenue Old Saybrook CT
15 Baum Avenue

Old Saybrook, Connecticut 06475

$365,000 | Active

2 Beds | 1 Baths | 928 Sqft | 0.22 Acres | 25 Days on Market

Property Type: Single Family For Sale

Incredible opportunity to re-imagine the interior of this charming year-round RANCH WITH REMARKABLE VIEWS! Just south of Route 1, this property offers one floor living with wide marsh views. The exterior has been updated and maintained over the last 5-8 years including new vinyl ...

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7/2/2026 1:43:43 AM
Active
53 Chalker Beach Road Old Saybrook CT
53 Chalker Beach Road

Old Saybrook, Connecticut 06475

$549,000 | Active

3 Beds | 1 Baths | 960 Sqft | 0.22 Acres | 30 Days on Market

Property Type: Single Family For Sale

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 fl...

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6/30/2026 12:06:00 PM
Active
34 Briarcliffe Trail Old Saybrook CT
34 Briarcliffe Trail

Old Saybrook, Connecticut 06475

$999,900 | Active

4 Beds | 3 Baths | 3720 Sqft | 1.31 Acres | 42 Days on Market

Property Type: Single Family For Sale

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 perfe...

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6/26/2026 4:05:03 AM
Active
25 River Avenue Old Saybrook CT
25 River Avenue

Old Saybrook, Connecticut 06475

$800,000 | Active

2 Beds | 1 Baths | 1478 Sqft | 0.15 Acres | 35 Days on Market

Property Type: Single Family For Sale

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...

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6/25/2026 2:01:50 AM
Under Contract
208 Ingham Hill Road Old Saybrook CT
208 Ingham Hill Road

Old Saybrook, Connecticut 06475

$615,000 | Under Contract

3 Beds | 3 Baths | 1926 Sqft | 2.22 Acres | 10 Days on Market

Property Type: Single Family For Sale

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 appli...

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6/23/2026 11:34:06 PM
Active
9 Barley Hill Road Old Saybrook CT
9 Barley Hill Road

Old Saybrook, Connecticut 06475

$850,000 | Active

4 Beds | 4 Baths | 3544 Sqft | 2.13 Acres | 67 Days on Market

Property Type: Single Family For Sale

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 roo...

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6/22/2026 10:28:48 PM
Under Contract CTS
95 Middletown Avenue Old Saybrook CT
95 Middletown Avenue

Old Saybrook, Connecticut 06475

$1,049,900 | Under Contract - Continue

4 Beds | 2 Baths | 1566 Sqft | 0.15 Acres | 71 Days on Market

Property Type: Single Family For Sale

95 Middletown Avenue offers a rare opportunity to enjoy four season living in the heart of Saybrook Manor, one of Old Saybrooks most sought after shoreline communities. Renovated in 2022 with thoughtful attention to comfort and design, this beautifully updated home combines timel...

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6/19/2026 4:05:03 AM
Active
52 Chalker Beach Road Old Saybrook CT
52 Chalker Beach Road

Old Saybrook, Connecticut 06475

$699,000 | Active

3 Beds | 2 Baths | 1120 Sqft | 0.17 Acres | 42 Days on Market

Property Type: Single Family For Sale

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...

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6/19/2026 4:05:02 AM
Active
2 Captains Lane Old Saybrook CT
2 Captains Lane

Old Saybrook, Connecticut 06475

$2,899,900 | Active

5 Beds | 5 Baths | 5062 Sqft | 0.35 Acres | 42 Days on Market

Property Type: Single Family For Sale

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 Bea...

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6/18/2026 9:00:02 PM
Active
2 Old South Cove Road Old Saybrook CT
2 Old South Cove Road

Old Saybrook, Connecticut 06475

$1,499,000 | Active

3 Beds | 4 Baths | 2472 Sqft | 0.16 Acres | 43 Days on Market

Property Type: Single Family For Sale

Welcome to one of Old Saybrooks most compelling brand-new luxury opportunities. Built by one of Connecticuts premier shoreline designers and builders, this exceptional coastal residence showcases a level of craftsmanship, architectural detail, and thoughtful design rarely found i...

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6/13/2026 3:52:30 PM
Under Contract
2 Cinnamon Way Old Saybrook CT
2 Cinnamon Way

Old Saybrook, Connecticut 06475

$645,000 | Under Contract

3 Beds | 3 Baths | 1890 Sqft | 0.96 Acres | 1 Days on Market

Property Type: Single Family For Sale

Surrounded by a peaceful preserve with beautiful views, this light filled custom contemporary Colonial offers a rare blend of privacy, flexibility, and classic Old Saybrook charm. Step through the new custom front door into an open, airy layout where natural light pours through n...

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6/13/2026 12:23:26 PM
Active
1445 Boston Post Road Old Saybrook CT
1445 Boston Post Road

Old Saybrook, Connecticut 06475

$12,000,000 | Active

4 Beds | 1 Baths | 2059 Sqft | 20.21 Acres | 48 Days on Market

Property Type: Single Family For Sale

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 cl...

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6/12/2026 9:12:38 PM
Active
13-A Cove Street Old Saybrook CT
13-A Cove Street

Old Saybrook, Connecticut 06475

$775,000 | Active

2 Beds | 1 Baths | 960 Sqft | 0.35 Acres | 57 Days on Market

Property Type: Single Family For Sale

Saybrook Point! Welcome to the coastal lifestyle youve 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...

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6/12/2026 2:20:41 PM
Active
18 Old South Cove Road Old Saybrook CT
18 Old South Cove Road

Old Saybrook, Connecticut 06475

$899,000 | Active

4 Beds | 3 Baths | 1569 Sqft | 0.42 Acres | 122 Days on Market

Property Type: Single Family For Sale

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 Dist...

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6/9/2026 2:03:07 AM
Active
104 Knollwood Drive Old Saybrook CT
104 Knollwood Drive

Old Saybrook, Connecticut 06475

$1,595,000 | Active

3 Beds | 2 Baths | 1809 Sqft | 0.37 Acres | 106 Days on Market

Property Type: Single Family For Sale

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 ho...

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6/1/2026 3:56:05 PM
Active
77 Essex Road Road Old Saybrook CT
77 Essex Road Road

Old Saybrook, Connecticut 06475

$1,495,000 | Active

3 Beds | 4 Baths | 2890 Sqft | 0.62 Acres | 60 Days on Market

Property Type: Single Family For Sale

Set on .62 acres along a protected canal just off the Connecticut River, this well built and maintained waterfront 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. Updated syst...

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5/30/2026 4:05:03 AM
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11 Cambridge Court Old Saybrook CT
11 East Cambridge Court

Old Saybrook, Connecticut 06475

$1,695,000 | Active

4 Beds | 3 Baths | 2178 Sqft | 1.6 Acres | 62 Days on Market

Property Type: Single Family For Sale

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-ac...

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5/15/2026 2:15:16 PM
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20 Saltus Drive Old Saybrook CT
20 Saltus Drive

Old Saybrook, Connecticut 06475

$9,850,000 | Active

5 Beds | 8 Baths | 9481 Sqft | 1.6 Acres | 168 Days on Market

Property Type: Single Family For Sale

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...

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5/15/2026 4:05:04 AM
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96 Chalker Beach Road Old Saybrook CT
96 Chalker Beach Road

Old Saybrook, Connecticut 06475

$649,900 | Active

3 Beds | 1 Baths | 968 Sqft | 0.17 Acres | 77 Days on Market

Property Type: Single Family For Sale

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 shorel...

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4/9/2026 6:25:24 PM
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12 Rocky Point Road Old Saybrook CT
12 Rocky Point Road

Old Saybrook, Connecticut 06475

$5,900,000 | Active

4 Beds | 4 Baths | 5651 Sqft | 1.13 Acres | 113 Days on Market

Property Type: Single Family For Sale

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...

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4/8/2026 3:21:30 PM
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11 River Edge Road Old Saybrook CT
11 River Edge Road

Old Saybrook, Connecticut 06475

$6,600,000 | Active

6 Beds | 4 Baths | 5739 Sqft | 3.43 Acres | 116 Days on Market

Property Type: Single Family For Sale

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 1,5...

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1/6/2026 9:07:01 PM
Under Contract CTS
125 Main Street Old Saybrook CT
125 Main Street

Old Saybrook, Connecticut 06475

$2,195,000 | Under Contract - Continue

1 Beds | 2 Baths | 7985 Sqft | 0.23 Acres | 267 Days on Market

Property Type: Single Family For Sale

Great mixed-use opportunity. Fully leased office building with town-approved one-bedroom apartment on Second Floor with kitchen, full bath including washer/dryer. Great opportunity to own a mixed-use property on beautiful Main Street in Old Saybrook. Established salon with long t...

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