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100 Dudley Avenue #F30, Old Saybrook, CT 06475
1/40 40

$797,000

Open Thu 11AM-1PM

Condo

2 Beds 3 Baths 1,565 SqFt

100 Dudley Avenue #F30, Old Saybrook, CT 06475

Spectacular North Cove unobstructed water views and downtown village living come together in this beautifully renovated ...

Listed by Joel Lucas of Coldwell Banker Realty

46 Farview Avenue, Old Saybrook, CT 06475
1/35 35

$599,000

Open 8/24 11AM-1PM

Single Family Home

3 Beds 2 Baths 1,552 SqFt

46 Farview Avenue, Old Saybrook, CT 06475

Location, location, location. Enjoy shoreline lifestyle in one of Old Saybrook's in demand neighborhoods. Level corner l...

Listed by Sheila Burke of J.M. REALTY

138 North Cove Road, Old Saybrook, CT 06475
1/2 2

$1,599,000

Coming Soon

Single Family Home

4 Beds 4 Baths 2,734 SqFt

138 North Cove Road, Old Saybrook, CT 06475

A Rare Coastal Opportunity Awaits! Set in the highly sought-after North Cove Historic District of Old Saybrook, this gra...

Listed by Marcello Delmonaco of Coldwell Banker Realty

71 Knollwood Drive, Old Saybrook, CT 06475
1/12 12

$799,500

Coming Soon

Single Family Home

3 Beds 2 Baths 1,856 SqFt

71 Knollwood Drive, Old Saybrook, CT 06475

KNOLLWOOD BEACH - Here is the opportunity! A Raised Ranch sitting on a wide .98-acre lot offering possibilities rarely f...

Listed by Matt Diamond of Houlihan Lawrence WD

43 Quarry Street, Old Saybrook, CT 06475
1/2 2

$285,000

New

Single Family Home

3 Beds 1 Bath 941 SqFt

43 Quarry Street, Old Saybrook, CT 06475

43 Quarry Street, Loved and occupied by the same owner for more than 40 years, this three-bedroom home on Quarry Street ...

Listed by Jennifer Gurnell of William Raveis Real Estate

6 Beaver Dam Trail, Old Saybrook, CT 06475
1/24 24

$3,900

New

Single Family Home

4 Beds 3 Baths 2,280 SqFt

6 Beaver Dam Trail, Old Saybrook, CT 06475

Available Sept 4, 2026. One-year lease minimum; credit check; non-smoking; pet-flexible. Nicely updated 4 BR, 2.5 bath C...

Listed by Adam Mancini of Ann McBride Real Estate

9 Red Bird Trail, Old Saybrook, CT 06475
1/18 18

$2,500

New

Single Family Home

3 Beds 2 Baths 1,440 SqFt

9 Red Bird Trail, Old Saybrook, CT 06475

ACADEMIC RENTAL until mid May 2027. Three BR Colonial with Sun Room located in the beautiful Indian Town Beach Associat...

Listed by Sandra Orsie of Berkshire Hathaway NE Prop.

24 West Shore Drive, Old Saybrook, CT 06475
1/40 40

$1,245,000

Active

Single Family Home

3 Beds 1 Bath 884 SqFt

24 West Shore Drive, Old Saybrook, CT 06475

Your Year-Round Beach Home Awaits in Cornfield Point Welcome to your opportunity to own a year-round home in Cornfield P...

Listed by David Rodriguez of William Pitt Sotheby's Int'l

38 Jarvis Road, Old Saybrook, CT 06475
1/40 40

$1,199,000

Active

Single Family Home

3 Beds 2 Baths 2,303 SqFt

38 Jarvis Road, Old Saybrook, CT 06475

Enjoy coastal living in the sought-after Knollwood Beach Association. This well-maintained, sun-filled home is just a sh...

Listed by Sharon Linder of Berkshire Hathaway NE Prop.

1324 Boston Post Road, Old Saybrook, CT 06475
1/20 20

$550,000

Active

Single Family Home

3 Beds 1 Bath 1,104 SqFt

1324 Boston Post Road, Old Saybrook, CT 06475

One floor living in Old Saybrook! This ranch home is a part of the Indian Town Beach association and also conveniently l...

Listed by Tina Rupp of William Pitt Sotheby's Int'l

17 Barnes Road, Old Saybrook, CT 06475
1/33 33

$749,900

Under Contract

Single Family Home

3 Beds 1 Bath 960 SqFt

17 Barnes Road, Old Saybrook, CT 06475

Great Hammock LIS beachfront seasonal cottage! Simply charming and in excellent condition, your beach vacation home awai...

Listed by Lynn Lehrman of Re/Max Valley Shore

13 College Street, Old Saybrook, CT 06475
1/2 2

$1,590,000

Active

Single Family Home

4 Beds 3 Baths 2,070 SqFt

13 College Street, Old Saybrook, CT 06475

13 College Street | Old Saybrook, CT TO BE BUILT Discover the opportunity to build your dream home in one of Old Saybroo...

Listed by Lisa Fekete of William Raveis Real Estate

27 Gates Road, Old Saybrook, CT 06475
1/37 37

$725,000

Active

Single Family Home

4 Beds 2 Baths 1,088 SqFt

27 Gates Road, Old Saybrook, CT 06475

Rare opportunity to own a classic Connecticut shoreline beach cottage in the highly sought-after Cornfield Point Beach A...

Listed by Jennifer Gurnell of William Raveis Real Estate

11 Kitteridge Hill Road, Old Saybrook, CT 06475
1/40 40

$699,000

Active

Single Family Home

3 Beds 3 Baths 2,755 SqFt

11 Kitteridge Hill Road, Old Saybrook, CT 06475

Tucked away on a peaceful cul-de-sac off School House Road, this beautifully maintained Cape offers over 2,700 square fe...

Listed by Jessica Blancato of William Pitt Sotheby's Int'l

8 Kenn Road, Old Saybrook, CT 06475
1/40 40

$649,000

Price Dropped by $50K

Single Family Home

2 Beds 2 Baths 1,040 SqFt

8 Kenn Road, Old Saybrook, CT 06475

Coastal living is calling! This is a fully furnished shoreline retreat set within the sought-after Chalker Beach Associa...

Listed by Mick Marsden of Compass Connecticut, LLC

32 King Street, Old Saybrook, CT 06475
1/40 40

$599,000

Active

Single Family Home

4 Beds 2 Baths 1,643 SqFt

32 King Street, Old Saybrook, CT 06475

You are walking distance to shopping, restaurants and public transportation from this in-town cape with 4 bedrooms, 2 fu...

Listed by Cherie Suhie of J.M. REALTY

18 Mohican Trail, Old Saybrook, CT 06475
1/39 39

$4,100

Under Contract

Single Family Home

4 Beds 2 Baths 2,772 SqFt

18 Mohican Trail, Old Saybrook, CT 06475

This quintessential beach house is available for academic rental from Sept. 15 to May 15. Enjoy coastal living in this b...

Listed by Joanne Breen of ERA Hart Sargis-Breen

81 Essex Road, Old Saybrook, CT 06475
1/18 18

$1,450,000

Active

Single Family Home

3 Beds 2 Baths 2,570 SqFt

81 Essex Road, Old Saybrook, CT 06475

Introducing a rare opportunity to build your dream home in one of Connecticut's most desirable shoreline communities. Lo...

Listed by Rachael Cisz of Serhant Connecticut, LLC

4 Elinor Road, Old Saybrook, CT 06475
1/34 34

$2,600

Active

Single Family Home

3 Beds 2 Baths 1,152 SqFt

4 Elinor Road, Old Saybrook, CT 06475

CHALKER BEACH ACADEMIC RENTAL AVAILABLE 9/15/26 - 5/15/26. Adorable fully furnished 3 bedroom, 1.1 bathroom Cape featuri...

Listed by Gera Delavega of KW Legacy Partners

5 Woodland Drive, Old Saybrook, CT 06475
1/40 40

$4,500

Active

Single Family Home

3 Beds 3 Baths 3,125 SqFt

5 Woodland Drive, Old Saybrook, CT 06475

WINTER RENTAL available September 15, 2026 through May 31, 2027 for $4,500/month. Enjoy spectacular Long Island Sound vi...

Listed by Joel Lucas of Coldwell Banker Realty

880 Boston Post Road, Old Saybrook, CT 06475
1/27 27

$1,500,000

Active

Commercial

1 Bath 13,836 SqFt

880 Boston Post Road, Old Saybrook, CT 06475

Unique mixed-use investment and redevelopment opportunity. The ground-floor commercial spaces are fully occupied, provid...

Listed by Aharon Cowen of Roundtree Realty LLC

170 Old Post Road, Old Saybrook, CT 06475
1/38 38

$999,000

Price Dropped by $201K

Single Family Home

3 Beds 3 Baths 2,128 SqFt

170 Old Post Road, Old Saybrook, CT 06475

Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with...

Listed by Rose McWaid of William Raveis Real Estate

2 Half Penny Lane, Old Saybrook, CT 06475
1/32 32

$575,000

Under Contract

Single Family Home

3 Beds 2 Baths 1,800 SqFt

2 Half Penny Lane, Old Saybrook, CT 06475

This charming home offers the perfect blend of charm, comfort, and opportunity. Filled with warmth, character, and endle...

Listed by Sharon Linder of Berkshire Hathaway NE Prop.

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