Old Saybrook, CT Homes

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  $1,375,000

  • 3 Beds
  • 1 Bath
  • 884 Sq Ft

  24 W Shore Dr, Old Saybrook, CT 06475

  The exceptional 24 W.Shore Dr. at the well known Cornfield Point Association residence offers an ideal blend of comfort, amazing waterviews, beach access and convenience. Solid brick custom home with impressive water views from the new upper deck and other areas of the house. 24 W. Shore Dr. is in move-in condition with remodeled kitchen with all new appliances, sun filled living room, 3 full

  David Rodriguez William Pitt Sotheby's Int'l

  24 W Shore Dr, Old Saybrook, CT 06475
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  $18,000 total monthly price

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

  8 Belaire Manor, Old Saybrook, CT 06475

  {Summer 2026 -- June: available -- July/Aug/Sept: rented} This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the

  Erika Raffles William Pitt Sotheby's Int'l

  8 Belaire Manor, Old Saybrook, CT 06475
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  $445,000 Sold Mar 21, 2025

  11 Evans Ln, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft
  • Built 1938

  Last Sold Summary

  • 1% Above List Price
  • $651/SF
  • 40 Days On Market

  Current Estimated Value $447,768

  Last Listing Agent Jordan Ostrofsky LPT Realty

  11 Evans Ln, Old Saybrook, CT 06475
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  Est $639,782 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,290 Sq Ft

  21 Baum Ave, Old Saybrook, CT 06475

  21 Baum Ave, Old Saybrook, CT 06475
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  $649,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft

  99 Maple Ave, Old Saybrook, CT 06475

  Coastal California style meets the charming Connecticut shoreline in this absolutely darling Old Saybrook Ranch. Thoughtfully updated and meticulously maintained, this home sits proudly on Maple Avenue, just a short sidewalk stroll to Main Street, The Kate, Saybrook Point Inn, and the beach. The main level features beautiful hardwood floors and a pretty, updated kitchen with granite countertops,

  Phoebe Finch William Pitt Sotheby's Int'l

  99 Maple Ave, Old Saybrook, CT 06475
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  $3,000 total monthly price

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

  8 Clinton Ave, Old Saybrook, CT 06475

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

  Terry McDonald McDonald Real Estate, LLC

  8 Clinton Ave, Old Saybrook, CT 06475
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  $650,000 Sold May 15, 2025

  37 Fenwood Rd, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1953

  Last Sold Summary

  • 6% Below List Price
  • $516/SF
  • 33 Days On Market

  Current Estimated Value $652,688

  Last Listing Agent Charles Conti Coldwell Banker Realty

  37 Fenwood Rd, Old Saybrook, CT 06475
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  Est $624,101 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,170 Sq Ft

  8 East St, Old Saybrook, CT 06475

  8 East St, Old Saybrook, CT 06475
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  $574,900 Pending

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

  254 Hidden Cove Rd, Old Saybrook, CT 06475

  Coastal Charm Meets Modern Comfort at 254 Hidden Cove Rd, Unit #254, Old Saybrook. Step inside to discover a fresh, modern interior featuring brand-new flooring, updated finishes, and a bright, open layout perfect for both relaxing and entertaining. The spacious living room flows seamlessly into the dining area and kitchen, creating a warm and inviting atmosphere. New Kitchen cabinets, Quartz

  Bob Yostos Coldwell Banker Realty

  254 Hidden Cove Rd, Old Saybrook, CT 06475
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  $2,400 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  9 Red Bird Trail, Old Saybrook, CT 06475

  SHORT TERM RENTAL until mid May 2026. Three BR Colonial with Sun Room located in the beautiful Indian Town Association. Views of LIS and harbor. Bright and spacious rooms. This location is perfect for walking, biking or strolling along the beach. Conveniently located to I95, Train Station, Shopping and The Kate. Sorry NO pets or smokers allowed.

  Sandy Orsie Berkshire Hathaway NE Prop.

  9 Red Bird Trail, Old Saybrook, CT 06475
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  $870,000 Sold Nov 20, 2025

  7 Sharon Ln, Old Saybrook, CT 06475

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1978

  Last Sold Summary

  • 13% Below List Price
  • $330/SF
  • 129 Days On Market

  Last Listing Agent Jessica Blancato William Pitt Sotheby's Int'l

  7 Sharon Ln, Old Saybrook, CT 06475
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  Est $608,253 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,288 Sq Ft

  18 Pheasant Hill Ln, Old Saybrook, CT 06475

  18 Pheasant Hill Ln, Old Saybrook, CT 06475
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  /40

  $639,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,099 Sq Ft

  11 Coulter St Unit 28, Old Saybrook, CT 06475

  Exceptional tri-level condo with many updated custom features. Open yet seperate main level living room, dining room, new kitchen with dining area and new half bath. Beautifully designed built in units through out the main level. Upper level has redesigned primary bedroom suite which includes sitting/office area, closets, large bath w/double sink vanity and walk in shower. New laundry room is

  Christine Fappiano Shoreline Real Estate Company

  11 Coulter St Unit 28, Old Saybrook, CT 06475
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  /19

  $2,400 total monthly price

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

  38 Seabreeze Rd, Old Saybrook, CT 06475

  Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with three bedrooms, an updated bathroom, eat-in kitchen, living room with fireplace, a wonderful sun porch and an outside

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
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  $800,000 Sold Jul 29, 2025

  92 Fenwood Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $442/SF
  • 2 Days On Market

  Current Estimated Value $793,668

  Last Listing Agent Fran Manganello Coldwell Banker Realty

  92 Fenwood Dr, Old Saybrook, CT 06475
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  Est $673,131 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft

  28 Attawanhood Trail, Old Saybrook, CT 06475

  28 Attawanhood Trail, Old Saybrook, CT 06475
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  $519,900

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  14 Denmore Ln, Old Saybrook, CT 06475

  This beautifully renovated ranch style home provides a perfect blend of modern style, comfort and luxury. As you enter you will be greeted by beautiful hardwood flooring creating a seamless flow from room to room elevating each space with enduring charm, comfort, and sophistication. This home boasts three spacious bedrooms and one full bathroom featuring sleek and modern finishes. The

  Terence Dominick Exceptional Real Estate LLC

  14 Denmore Ln, Old Saybrook, CT 06475
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  $5,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • House for Rent

  25 W Shore Dr, Old Saybrook, CT 06475

  BEACHFRONT Beautifully renovated Furnished luxury waterfront monthly rental for annually $10,500 or winter for $5900 a month 9/30/25 to 5/15/26 (some flexibility with dates). $1200 a day for June 1st thru Sept. 15th. Waterviews from all rooms, private beach, plus cornfield point assocation amenties. Enjoy 3 bedrooms all with water-views, 2 full bathrooms, 1 half bathroom, fireplace, CA, new

  Joel Lucas Coldwell Banker Realty

  25 W Shore Dr, Old Saybrook, CT 06475
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  $742,900 Sold Oct 31, 2025

  16 Howard St, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $529/SF
  • 3 Days On Market

  Current Estimated Value $731,605

  Last Listing Agent Terry Kemper Coldwell Banker Realty

  16 Howard St, Old Saybrook, CT 06475
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  Est $119,206 Not Listed For Sale

  22 Ragged Rock Rd, Old Saybrook, CT 06475

  22 Ragged Rock Rd, Old Saybrook, CT 06475
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  $570,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,711 Sq Ft

  175 Ferry Rd Unit 10, Old Saybrook, CT 06475

  Welcome to Eden Harbour 55+ upscale living! Elegance, comfort, and convenience come together in this 2-bedroom, 2 bath, ranch style end unit, just minutes from downtown Old Saybrook. Enjoy single level living with an inviting open floor plan that balances sophistication with effortless everyday living. The open eat-in kitchen flows seamlessly to a gracious living area with a gas fireplace and

  Claire Kilmer Coldwell Banker Realty

  175 Ferry Rd Unit 10, Old Saybrook, CT 06475
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  /22

  $4,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • House for Rent

  28 Beach Rd W, Old Saybrook, CT 06475

  Amazing views of Long Island Sound at 28 Beach Rd West, Old Saybrook! Beautiful Academic Rental "beach" home, with 3 bedrooms and 2 baths, available for your enjoyment, across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

  Terry McDonald McDonald Real Estate, LLC

  28 Beach Rd W, Old Saybrook, CT 06475
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  $775,000 Sold Aug 05, 2025

  16, 18 Bayberry Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1958

  Last Sold Summary

  • 9% Below List Price
  • $1,009/SF
  • 97 Days On Market

  Last Listing Agent Cherie Suhie J.M. REALTY

  16, 18 Bayberry Rd, Old Saybrook, CT 06475
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  Est $980,543 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,178 Sq Ft

  11 Fenwood Ave, Old Saybrook, CT 06475

  11 Fenwood Ave, Old Saybrook, CT 06475
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  $519,000

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

  118 Sandy Point Rd, Old Saybrook, CT 06475

  Summerwood on the Sound. Step into this stunning townhouse condominium featuring a fabulous kitchen with spacious quartz counters and breakfast bar, custom designed cabinetry and stainless steel appliances. The open concept living room and dining area boast beautiful wood flooring, elegant crown molding and glass doors to the private deck area, perfect for relaxing and entertaining. There is also

  Carla Mousch William Raveis Real Estate

  118 Sandy Point Rd, Old Saybrook, CT 06475
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  $620,000 Sold Jul 31, 2025

  37 Woodland Dr, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 22% Below List Price
  • $413/SF
  • 94 Days On Market

  Current Estimated Value $654,081

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  37 Woodland Dr, Old Saybrook, CT 06475
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  Est $592,640 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  407 Main St, Old Saybrook, CT 06475

  407 Main St, Old Saybrook, CT 06475
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  /30

  $374,900

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft

  195 Bokum Rd, Old Saybrook, CT 06475

  INVESTORS & CONTRACTORS - A RARE OPPORTUNITY AWAITS. Step into the past with this 1799-built home, beautifully sited on a secluded, level 2.18-acre lot that features a peaceful spring-fed pond with culverts in and out, and over 1,000 acres of preserved land directly behind the property offering remarkable privacy and a peaceful backdrop that will remain for years to come. The home offers 3

  Dotty Owens Sunset Creek Realty, LLC

  195 Bokum Rd, Old Saybrook, CT 06475
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  $600,000 Sold Mar 24, 2025

  9 Trolley Crossing, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $413/SF
  • 40 Days On Market

  Current Estimated Value $609,698

  Last Listing Agent Jackie Lyman Lyman Real Estate

  9 Trolley Crossing, Old Saybrook, CT 06475
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  Est $1,173,933 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,048 Sq Ft

  10 Turnstone Rd, Essex, CT 06426

  10 Turnstone Rd, Essex, CT 06426
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  $2,195,000 Under Contract

  • 1 Bed
  • 1.5 Baths
  • 7,985 Sq Ft

  125 Main St, Old Saybrook, CT 06475

  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 term lease on first floor. The one bedroom apartment on the second floor has been carpeted and painted and has separate

  Gary Marino William Raveis Real Estate

  125 Main St, Old Saybrook, CT 06475
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  $575,000 Sold May 15, 2025

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475

  • 2 Beds
  • 2 Baths
  • 1,898 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $303/SF
  • 57 Days On Market

  Current Estimated Value $580,673

  Last Listing Agent Carla Mousch William Raveis Real Estate

  227 Hidden Cove Rd Unit 227, Old Saybrook, CT 06475
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  Est $423,688 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft

  15 Cranton Ave, Old Saybrook, CT 06475

  15 Cranton Ave, Old Saybrook, CT 06475
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  /40

  $750,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,076 Sq Ft

  41 Briarwood Dr, Old Saybrook, CT 06475

  This special home is perched high and dry on a sunny lot overlooking the great saltmarsh towards Long Island Sound. The views from this property must be seen to be appreciated and no flood insurance is required. Inside a warm, comfortable and open floorplan awaits the next owner with a private, association beach just a short walk, bike or golf cart ride away. Perfect for you your around home or a

  Rick Allen William Raveis Real Estate

  41 Briarwood Dr, Old Saybrook, CT 06475
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  $890,999 Sold Apr 24, 2025

  49 Atlantic Dr, Old Saybrook, CT 06475

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Above List Price
  • $543/SF
  • 0 Days On Market

  Current Estimated Value $903,130

  Last Listing Agent Joel Lucas Coldwell Banker Realty

  49 Atlantic Dr, Old Saybrook, CT 06475
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  Est $548,041 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,288 Sq Ft

  136 Sandy Point Rd, Old Saybrook, CT 06475

  136 Sandy Point Rd, Old Saybrook, CT 06475
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  /22

  $799,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  21 Fenwick St, Old Saybrook, CT 06475

  This home is being sold "AS IS".Right place at the right time! This home now wants a new owner. Renovations are needed but location, location, location.Water views with walking ability to Saybrook Point and Fenwick golf course. Ranch with 3 beds and 2 baths. This is an opportunity to enjoy and experience Old Saybrook at its best. The beautiful views from inside the home is an ever-changing

  Paula Stuart Berkshire Hathaway NE Prop.

  21 Fenwick St, Old Saybrook, CT 06475
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  $935,000 Sold Dec 16, 2025

  19 Lynde St, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • Built 1918

  Last Sold Summary

  • 1% Above List Price
  • $390/SF
  • 62 Days On Market

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  19 Lynde St, Old Saybrook, CT 06475
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  Est $635,619 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,352 Sq Ft

  44 Middletown Ave, Old Saybrook, CT 06475

  44 Middletown Ave, Old Saybrook, CT 06475
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  $19,000 Pending

  • Land
  • 0.8 Acre
  • $23,750 per Acre

  0 Merritt Ln, Old Saybrook, CT 06475

  NOT BUILDABLE LOT! .80 acres overlooking Chalkers Millpond on cul-de-sac .

  Claude Cousins Berkshire Hathaway NE Prop.

  0 Merritt Ln, Old Saybrook, CT 06475

Showing Results 41 - 80, Page 2 of 18