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 Sunday, July 19, 2026
62 Active Homes Listed
42 Avg. DOM
$215 Avg. $ / Sq.Ft.
$526250 Med. List Price
7/19/2026 4:05:02 AM
Active
420 Maple Avenue Old Saybrook CT
420 Maple Avenue

Old Saybrook, Connecticut 06475

$1,950,000 | Active

3 Beds | 3 Baths | 1900 Sqft | 0.25 Acres | 0 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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7/17/2026 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 | 30 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 3:00:21 PM
Active
4 Beach Road Old Saybrook CT
4 Beach Road

Old Saybrook, Connecticut 06475

$1,425,000 | Active

3 Beds | 3 Baths | 3745 Sqft | 3.42 Acres | 45 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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7/16/2026 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 | 3 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
21 Baum Avenue Old Saybrook CT
21 Baum Avenue

Old Saybrook, Connecticut 06475

$584,900 | Active

2 Beds | 2 Baths | 1290 Sqft | 0.25 Acres | 3 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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7/16/2026 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 | 3 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 | 9 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 9:38:48 PM
Active
22 Beaver Dam Trail Old Saybrook CT
22 Beaver Dam Trail

Old Saybrook, Connecticut 06475

$599,000 | Active

4 Beds | 3 Baths | 1934 Sqft | 1.04 Acres | 15 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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7/15/2026 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 | 30 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 9:34:07 PM
Active
25 Uncas Trail Old Saybrook CT
25 Uncas Trail

Old Saybrook, Connecticut 06475

$849,900 | Active

2 Beds | 2 Baths | 1760 Sqft | 0.11 Acres | 6 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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7/14/2026 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 | 110 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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7/13/2026 5:34:04 PM
Under Contract
34 Sunset Avenue Old Saybrook CT
34 Sunset Avenue

Old Saybrook, Connecticut 06475

$375,000 | Under Contract

2 Beds | 1 Baths | 750 Sqft | 0.25 Acres | 8 Days on Market

Property Type: Single Family For Sale

Charming Custom Cottage in Old Saybrook - Welcome to this adorable 750-square-foot home nestled in the heart of Old Saybrook. Thoughtfully designed and full of character, this cozy retreat offers the perfect blend of timeless charm and modern comfort. Step inside to discover beau...

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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 | 17 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 | 8 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 | 9 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 5:21:51 PM
Active
9 Old Colony Road Old Saybrook CT
9 Old Colony Road

Old Saybrook, Connecticut 06475

$725,000 | Active

4 Beds | 2 Baths | 1344 Sqft | 0.23 Acres | 10 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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7/9/2026 1:42:17 PM
Active
14 Cedarwood Lane Old Saybrook CT
14 Cedarwood Lane

Old Saybrook, Connecticut 06475

$615,000 | Active

3 Beds | 2 Baths | 1033 Sqft | 0.64 Acres | 21 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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7/9/2026 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 | 10 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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7/9/2026 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 | 10 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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7/8/2026 2:19:39 PM
Active
21 Fenbrook Road Old Saybrook CT
21 Fenbrook Road

Old Saybrook, Connecticut 06475

$1,440,000 | Active

3 Beds | 3 Baths | 1916 Sqft | 0.22 Acres | 74 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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7/8/2026 12:44:48 PM
Active
9 Farview Avenue Old Saybrook CT
9 Farview Avenue

Old Saybrook, Connecticut 06475

$526,250 | Active

3 Beds | 1 Baths | 1038 Sqft | 0.24 Acres | 32 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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7/7/2026 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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7/7/2026 3:54:53 PM
Under Contract
29 Old Post Road Old Saybrook CT
29 Old Post Road

Old Saybrook, Connecticut 06475

$745,000 | Under Contract

3 Beds | 3 Baths | 1604 Sqft | 0.23 Acres | 6 Days on Market

Property Type: Single Family For Sale

Welcome to Crows Nest, where classic New England country living meets direct waterfront luxury on the scenic Oyster River. Steeped in history, this enchanting historic farmhouse Circa 1850, is perfectly positioned along the west banks of the Oyster River, offering breathtaking w...

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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 | 13 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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7/5/2026 11:39:16 PM
Under Contract
6 Trolley Crossing Old Saybrook CT
6 Trolley Crossing

Old Saybrook, Connecticut 06475

$997,000 | Under Contract

3 Beds | 3 Baths | 3917 Sqft | 1 Acres | 16 Days on Market

Property Type: Single Family For Sale

Quintessential New England Gambrel Colonial with a dramatic sunroom addition and a brand new roof! Sited in a quiet cul-de-sac neighborhood, the gorgeous one acre grounds include numerous mature flowering trees and shrubs, as well as a pine tree perimeter for privacy. The origina...

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7/5/2026 1:26:46 PM
Active
5 Woodland Drive Old Saybrook CT
5 Woodland Drive

Old Saybrook, Connecticut 06475

$1,590,000 | Active

3 Beds | 3 Baths | 3125 Sqft | 0.17 Acres | 107 Days on Market

Property Type: Single Family For Sale

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-...

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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 | 18 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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7/1/2026 7:23:51 PM
Active
96 Ayers Point Road Old Saybrook CT
96 Ayers Point Road

Old Saybrook, Connecticut 06475

$1,163,000 | Active

4 Beds | 3 Baths | 4109 Sqft | 1.14 Acres | 18 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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7/1/2026 2:49:52 PM
Under Contract CTS
86 Fenwood Drive Old Saybrook CT
86 Fenwood Drive

Old Saybrook, Connecticut 06475

$874,900 | Under Contract - Continue

2 Beds | 3 Baths | 2209 Sqft | 0.3 Acres | 30 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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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 | 30 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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6/30/2026 12:09:07 AM
Under Contract
44 Coulter Street Old Saybrook CT
44 Coulter Street

Old Saybrook, Connecticut 06475

$450,000 | Under Contract

3 Beds | 1 Baths | 960 Sqft | 0.28 Acres | 4 Days on Market

Property Type: Single Family For Sale

Located in one of Connecticuts most desirable shoreline communities, this 3-bedroom ranch offers an incredible opportunity to create the home of your dreams. Just steps from downtown Old Saybrook and just up the street from one of the best scenic views in town. Youll enjoy easy a...

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6/27/2026 11:16:41 AM
Active
61 Ingham Hill Road Old Saybrook CT
61 Ingham Hill Road

Old Saybrook, Connecticut 06475

$415,000 | Active

1 Beds | 2 Baths | 1205 Sqft | 0.39 Acres | 77 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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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 | 23 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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6/24/2026 3:48:07 PM
Under Contract CTS
8 Owaneco Trail Old Saybrook CT
8 Owaneco Trail

Old Saybrook, Connecticut 06475

$2,195,000 | Under Contract - Continue

4 Beds | 4 Baths | 2881 Sqft | 0.46 Acres | 34 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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6/24/2026 1:34:20 PM
Active
37 Woodland Drive Old Saybrook CT
37 Woodland Drive

Old Saybrook, Connecticut 06475

$1,100,000 | Active

3 Beds | 2 Baths | 1426 Sqft | 0.33 Acres | 25 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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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 | 55 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 | 59 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 11:17:18 PM
Active
6 Fencove Court Old Saybrook CT
6 Fencove Court

Old Saybrook, Connecticut 06475

$1,350,000 | Active

4 Beds | 4 Baths | 2040 Sqft | 0.52 Acres | 39 Days on Market

Property Type: Single Family For Sale

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 spa...

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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 | 30 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 | 30 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 | 31 Days on Market

Property Type: Single Family For Sale

Welcome to one of Old Saybrooks 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 ne...

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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 | 36 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 | 45 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 | 110 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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6/10/2026 5:35:47 PM
Under Contract
30 Sunset Avenue Old Saybrook CT
30 Sunset Avenue

Old Saybrook, Connecticut 06475

$410,000 | Under Contract

4 Beds | 1 Baths | 1670 Sqft | 0.16 Acres | 7 Days on Market

Property Type: Single Family For Sale

Welcome to this cozy, charming, cape style home located in the shoreline community of Old Saybrook. This property is situated just moments away from nearby beaches, marinas, restaurants and shopping. This four-bedroom cape is updated with town records and features a finished ba...

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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 | 94 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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6/5/2026 11:57:51 AM
Active
28 Church Street Old Saybrook CT
28 Church Street

Old Saybrook, Connecticut 06475

$600,000 | Active

2 Beds | 1 Baths | 768 Sqft | 0.25 Acres | 44 Days on Market

Property Type: Single Family For Sale

This well-maintained 2-bedroom, 1-bathroom ranch is the ultimate turnkey opportunity in one of Connecticuts 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 Saybro...

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6/3/2026 8:06:30 PM
Active
14 Anchorage Lane Old Saybrook CT
14 Anchorage Lane

Old Saybrook, Connecticut 06475

$2,000,000 | Active

4 Beds | 2 Baths | 1776 Sqft | 0.31 Acres | 46 Days on Market

Property Type: Single Family For Sale

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 wind...

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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 | 48 Days on Market

Property Type: Single Family For Sale

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 ...

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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 | 50 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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5/27/2026 11:57:56 AM
Under Contract
6 Watch Hill Road Old Saybrook CT
6 Watch Hill Road

Old Saybrook, Connecticut 06475

$551,000 | Under Contract

3 Beds | 3 Baths | 2830 Sqft | 0.94 Acres | 26 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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5/15/2026 2:15:16 PM
Active
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 | 156 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
Active
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 | 65 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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5/1/2026 4:05:10 AM
Active
92 Bokum Road Old Saybrook CT
92 Bokum Road

Old Saybrook, Connecticut 06475

$559,000 | Active

2 Beds | 2 Baths | 1376 Sqft | 1.71 Acres | 79 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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4/28/2026 3:13:10 PM
Active
17 College Street Old Saybrook CT
17 College Street

Old Saybrook, Connecticut 06475

$1,140,000 | Active

3 Beds | 3 Baths | 1960 Sqft | 0.48 Acres | 119 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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4/9/2026 6:25:24 PM
Active
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 | 101 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
Active
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 | 104 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 | 255 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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