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44 Coulter St, Old Saybrook
$531,000
3 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24183873 MLS
Located in one of Connecticut's 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. You'll enjoy easy access to shops, restaurants, marinas, beaches, and all the coastal charm this beloved town has to offer. The seller has already completed some of the preparation work, including carpet removal to reveal hardwood floors, wallpaper removal, and fresh interior paint throughout. This solid home is ready for your finishing touches and personal vision. The spacious, level lot features a lovely backyard with garden potential, while the full basement offers endless possibilities for expansion into a family room, recreation area, home office, or additional living space. A fireplace adds character and warmth, creating the perfect focal point for future gatherings. If you are someone looking to customize a home in a premier shoreline location, this property is filled with potential and opportunity. Don't miss your chance to own in the picturesque town of Old Saybrook, known for its beautiful beaches, vibrant downtown, and exceptional coastal lifestyle.

44 Coulter St, Old Saybrook
55 Woodland Dr, Old Saybrook
$525,000
4 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24178053 MLS
Tremendous opportunity in the sought-after Knollwood Beach Association! This coastal property is ideal for builders, flippers, investors, or buyers looking to create a custom beach retreat. Included in the sale is a rare undeveloped .40-acre lot at 53 Woodland Drive with its own separate field card, offering exceptional flexibility and future potential. The existing home needs significant cosmetic renovation and is being sold strictly "as is," but the layout, bones, and mechanical systems appear solid. Dry basement adds additional value and utility. The home was occupied until several months ago, though sellers have never lived in the property and no disclosures are available. Possible second-floor water views if rebuilt or expanded. Located in one of Old Saybrook's most desirable beach communities with access to Knollwood Beach Association amenities including a private sandy beach, clubhouse, tennis, pickleball, basketball, kayak storage, and more. Rare chance to renovate, rebuild, or develop in a prime shoreline location. Offers with financing will not be accepted.

55 Woodland Dr, Old Saybrook
92 Bokum Rd, Old Saybrook
$525,000
2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24164864 MLS
A rare and captivating offering, this enchanting storybook residence has been beautifully reimagined to deliver a seamless blend of historic charm and refined design. Whether you choose to continue its success as a turnkey Airbnb investment or keep it for your own year round or weekend retreat, the possibilities are as inviting as the home itself. Thoughtfully updated with a brand new roof and updated plumbing and septic, it offers modern peace of mind while preserving its timeless character. Rich in personality, the home evokes the romance of a countryside Tuscan Villa, from its ivy draped exterior to the layered, designer interiors originally re envisioned by Charles Spada in the 1990s. The private backyard is a tranquil escape, featuring exquisite stonework and curated plantings meant for quiet moments or intimate gatherings. Ideally situated just moments from boutique shopping, galleries, dining, Old Saybrook Town Beach, and the Katharine Hepburn Cultural Arts Center, this exceptional home offers both lifestyle and convenience. Featured in House Beautiful and Home Decorating Ideas, it is a true one of a kind residence ready to be enjoyed immediately, with furnishings available for purchase if desired.

92 Bokum Rd, Old Saybrook
49 River St, Old Saybrook
$525,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24168604 MLS
Spacious village area colonial with lot's of space and in what a location, a short stroll to Main Street and convenient to shops, highways and the railroad station. Featuring 9 rooms and 4 bedrooms with a second upper level kitchenette, this floorplan suits all of your housing needs at a price which won't bust the budget. Could potentially accommodate an in-law use with the second kitchen.

49 River St, Old Saybrook
9 Farview Ave, Old Saybrook
$500,000
3 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24184175 MLS
Charming Coastal Ranch in an incredible Old Saybrook location! This well-maintained ranch offers the perfect blend of comfort, convenience, and shoreline lifestyle. An easy flow layout which includes 3 bedrooms, living room, dining room, kitchen, full bath and a full unfinished basement for additional storage or workshop. Step outside to a spacious backyard designed for entertaining, relaxing, and enjoying warm summer evenings. This home invites morning walks and evening strolls to Harvey's Beach, Saybrook town beach, Trask Park with a splash pad, and the shops and restaurants along Main Street. Whether you're heading out for dinner, catching the train, or enjoying a beach day, everything you love about Old Saybrook is right at your fingertips. A rare opportunity to own a lovingly cared for home in one of the shoreline's most sought-after areas-perfect as a year-round residence, weekend escape or investment. Come take a look!

9 Farview Ave, Old Saybrook
9 2nd Ave, Old Saybrook
$500,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24159117 MLS
Experience the charm of picturesque Old Saybrook & enjoy all that shoreline living has to offer incl. beaches, boating, fine dining, theater & Main Street shopping.This well-maintained ranch-style home offers comfortable one-level living on a quiet dead-end street, conveniently located just minutes to downtown, Routes 9, I- 95, marinas & a public boat launch. The home is nicely landscaped & thoughtfully updated. It features 2 bedrooms w/gleaming hardwood floors & new ceiling fans, along w/a tastefully renovated bathroom showcasing a walk-in shower. The light-filled interior highlights a fully renovated kitchen w/new cabinetry,quartz countertops, SS appliances, gas range w/hood & smart refrigerator. A charming 3-season sunroom provides a cozy spot to enjoy morning coffee or unwind at the end of the day. Step outside to a newly built wraparound deck offering ample room for grilling & outdoor seating, overlooking a private backyard. Additional updates: new roof (2020), an 11-year-old septic system, solar panels installed 2025, Central AC 2017 & an updated electrical system-making this an energy-efficient home. A garage & generous basement provide excellent storage options. This move-in-ready home is ideal as a condo alternative, for first-time buyers, those looking to downsize, or anyone seeking the ease of one-floor living. Enjoy a short walk to the scenic Connecticut River. Pride of ownership is evident thruout-don't miss the opportunity to make this charming home your own!

9 2nd Ave, Old Saybrook
240 Elm St, Old Saybrook
$480,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24164362 MLS
Welcome to a home where quality meets comfort, starting with a charming brick walkway and vibrant perennials that lead to an inviting front entrance with a character-filled full dining area. This seamless one-floor layout continues into the eat-in kitchen, which boasts a spacious countertop, and a convenient first-floor laundry room complete with a half bath. Relax in the living room, featuring a slider that leads out to the deck, or retreat to the primary bedroom suite equipped with a full shower and a relaxing Jacuzzi tub. Built in 2007 on a 1.33-acre lot, this sturdy 3-bedroom home with 2 full baths and a half bath offers the ease of one-floor living with a 572-square-foot 2-car garage connected to the lower level. The 832-square-foot walk-out unfinished basement leads directly to the garden and can be completed however your heart desires-whether as a home office, media room, gym, or expansive storage. Enjoy low annual taxes of $3,465 while being moments away from the 1,000 Acre Preserve, the gourmet delights of Pasta Vita, and a variety of nearby shops, clinics, and restaurants, plus a short drive to the beach for the summer. With a top-tier school system and the charm of this deeply community-oriented town, there is nothing left to do but move in and enjoy the premier Old Saybrook lifestyle. Situated in the AA-1 zone with an ample parking area, this property offers great potential for professional offices or a home-based business.

240 Elm St, Old Saybrook
14 Denmore Ln, Old Saybrook
$460,000
3 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24170563 MLS
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 chef-inspired kitchen features sleek, new appliances, stylish cabinetry, and quartz countertops, ideal for both everyday meals and entertaining. The bright, airy living areas are enhanced with plenty of natural light in this single level living home. Situated in a desirable neighborhood in close proximity to the beach, this home is move-in ready and waiting for its new owners. Don't miss the opportunity because it won't last!

14 Denmore Ln, Old Saybrook
34 Sunset Ave, Old Saybrook
$400,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24185319 MLS
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 beautifully crafted custom wainscoting that adds warmth, elegance, and distinctive New England style throughout the living spaces. Natural light fills the home, creating a bright and inviting atmosphere that feels both spacious and welcoming. The efficient floor plan maximizes every square foot, featuring comfortable living areas, a well-appointed kitchen, and charming details that make this home truly special. Whether you're looking for a year-round residence, weekend getaway, or downsizing opportunity, this property offers easy living without sacrificing character. Outside, enjoy a manageable yard with space for relaxing, gardening, or entertaining. This adorable home was freshly painted inside and out, brand new carpeting and fresh stone on the driveway. Located just minutes from beaches, marinas, restaurants, and shopping, you'll experience all the coastal charm that Old Saybrook has to offer.

34 Sunset Ave, Old Saybrook
5 Sunrise Ave, Old Saybrook
$400,000
3 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24159189 MLS
Welcome to this well-maintained rambler ranch offering comfortable one-level living in beautiful Old Saybrook. This home features 3 spacious bedrooms and 1.5 bathrooms with central air, perfect for everyday living or hosting guests. Inside, you'll find beautiful hardwood floors that add warmth and character throughout much of the home. The layout includes a dedicated laundry room for added convenience and a bright, functional living space ideal for relaxing or entertaining. Step outside to enjoy a fenced-in, level backyard-perfect for pets, play, gardening, or outdoor gatherings. Located in the charming shoreline community of Old Saybrook, this home offers a wonderful opportunity to enjoy coastal Connecticut living while still being close to local shops, dining, beaches, and major routes. Don't miss the chance to make this inviting property your next home! A few "virtually staged" photos for ideas - small updates and big returns on your investment. Here's your second chance to own this charming shoreline home at an incredible value. With a motivated seller and a recent price reduction, this opportunity won't last. Enjoy close proximity to the water, marina, and beaches, all while benefiting from no flood insurance requirement. Whether you're downsizing or buying your first home, this inviting property offers the perfect blend of comfort, location, and affordability in a quaint coastal community. Act quickly - opportunities like this don't come around!

5 Sunrise Ave, Old Saybrook
369 Boston Post Rd, Old Saybrook
$400,000
2 Baths ⋅ CLOSED Status ⋅ 24124701 MLS
PRICED REDUCED .... This is the perfect commercial property, with mixed use and a great business opportunity, close to the center of Old Saybrook! Great opportunity for owner occupied or numerous business opportunities for rental space; Professional Offices, Law Office, Hair Salons, Nail Salon, Massage Studio, Therapist, etc... close to town and local businesses. Great investment opportunity collect rent and run your own business as an owner occupied property on the main level and collect rent from residential tenants upstairs. Lots of private off street parking paved driveway, great traffic count easy access to 95S, 95N and Rt9. Newer hot water heater, newer windows, public water, siding with a nice lawn for great curb appeal this property has a sign with electrical for great visibility for your business. Nothing to do, but put your personal touches on this property with a front entry area, numerous offices on the main level and multiple egress within the property that allows this property to be a perfect fit for any business! SCHEDULE YOUR PRIVATE TOUR! SHOWN BY APPOINTMENT ONLY NO DRIVE BY'S PLEASE! AS IS / WHERE AS

369 Boston Post Rd, Old Saybrook
30 Sunset Ave, Old Saybrook
$395,000
4 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24180469 MLS
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 basement with plenty of entertaining space. Additionally, you can step outside and enjoy a lovely deck that is perfect for family gatherings. This is an Estate Sale subject to probate approval. House sold "AS IS:

30 Sunset Ave, Old Saybrook
39 Middletown Ave, Old Saybrook
$385,000
4 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24157756 MLS
Charming and beautifully updated 4 bedroom partially furnished Seasonal Cottage in desireable Saybrook Manor beach community. This home offers the perfect blend of character and modern improvements with vaulted ceilings and exposed beams. The completely remodeled kitchen features Corian countertops, a classic farmhouse sink, skylight for natural light and matching rolling kitchen cart for added prep and storage space. The renovated bathroom includes a luxurious rainfall shower head for a spa-like feel. The bright dining room is enhanced by a large new slider that opens to a spacious stone patio-ideal for indoor/outdoor living. The Living room has a skylight offering warmth and brightness for your gatherings. Enjoy summer evenings around the fire pit or rinse off in the outdoor shower with both hot and cold water after a day at the beach and enjoy dining under the pergula watching the sunset. Additional updates include new windows, new plumbing, and updated electrical, offering peace of mind for years to come. A perfect coastal-style retreat with thoughtful upgrades inside and out. Square footage does not include enclosed porch (an additional 140 sq ft). 2 short blocks from the Private community beach easily accessed with the included Golf Cart.

39 Middletown Ave, Old Saybrook
13 College St, Old Saybrook
$380,000
1 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24158935 MLS
Adorable seasonal beach cottage nestled in the heart of Old Saybrook! This charming 2-bedroom, 1 bath retreat offers the perfect blend of coastal charm and convenience. Enjoy the large deep back yard and outdoor shower after you return from a day at the beach. Connected to public water and ideally located just a short stroll to town, or the Saybrook Point Inn. Whether you're dreaming of summer memories by the shore or re-imagining this as a year-round residence, this sweet cottage is full of potential. Don't miss your chance to own a slice of shoreline serenity.!

13 College St, Old Saybrook
61 Ingham Hill Rd, Old Saybrook
$365,000
1 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24169155 MLS
Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from Old Saybrook's stunning beaches. Thoughtfully remodeled, this cozy retreat blends historical character with modern comforts. As you enter, you'll find a spacious area that offers endless possibilities-use it as an eating area, a flex office, or even a sleeping space. The open floor plan invites effortless living, with an eat-in kitchen showcasing a center island and newer appliances. Off the kitchen, a slider leads to a spacious back deck, perfect for outdoor dining or soaking in the coastal air. Built-in shelves add both charm and function to the main living area, which also features a convenient first-floor half bath and laundry. Head upstairs to discover a spacious bedroom paired with a full bath featuring a stall shower. The property doesn't stop impressing there-a full basement offers storage or potential, while the flat lot includes a versatile barn/garage and an adorable gazebo perfect for relaxing or entertaining. With public water and an unbeatable location, this home is ready to be your seaside escape or year-round haven. Welcome to the best of Old Saybrook living!

61 Ingham Hill Rd, Old Saybrook
254 Main St, Old Saybrook
$350,000
CLOSED Status ⋅ 24113319 MLS
Turn-Key Restaurant Opportunity - The Rabbit Hole, Old Saybrook is a well-established and fully operational restaurant and bar, The Rabbit Hole, proudly serving the Old Saybrook and shoreline community for over 16 years. This turn-key business is a local favorite and premier destination, known for its award-winning food and beverages, welcoming atmosphere, and outstanding service. With seating for 10 at the bar and over 40 at tables, plus additional seasonal outdoor seating, the space is perfectly designed for both casual diners and sports enthusiasts alike. The Rabbit Hole enjoys a strong customer base, excellent reputation, and steady year-round traffic. See disclosure for complete list of property conveyed with the sale. Don't miss this rare opportunity to own a proven business in one of the shoreline's most vibrant communities. Highlights include: * Strong local brand recognition and loyal customer base * Prime location in a high-visibility, high-traffic area located on Main Street Old Saybrook * Well-maintained bar/restaurant interior with modern updates * All FF&E (furniture, fixtures & equipment) included in sale * Ample on-site parking (on Main Street and rear off street parking) See disclosures for a complete list of equipment and property included with the sale. Whether you're an experienced operator or an entrepreneur looking to step into a profitable business, this is a must-see opportunity. Schedule a confidential showing today.

254 Main St, Old Saybrook
124 Old Boston Post Rd, Old Saybrook
$299,000
CLOSED Status ⋅ 24165491 MLS
Considering a new build now or in the future? Can't find, "just the right property?" It's time to secure this very special location. Welcome to 124 Old Boston Post Road, an incredible .31 acre building lot in the heart of downtown Old Saybrook. Walk to the Acton Library, Trask Park tennis/pickleball and splash pad and a half mile to Main Street restaurants, shops, town offices and schools. Enjoy the loop - a morning bike ride to Saybrook Point, across the South Cove Causeway and home - magnificent views in seven miles. Spend the afternoon at Fenwick for a quick round of golf and catch the sunset at Town Beach. Pick up your favorites at Walt's for an evening grill or enjoy Old Saybrook's terrific restaurants. All are a short distance from the property. Old Saybrook is a small town with big amenities and easy access to Saybrook Station making it a wonderful weekend, summer and year round destination. Come for a weekend, stay forever.

124 Old Boston Post Rd, Old Saybrook
21 Harvey Dr, Old Saybrook
$185,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24158257 MLS
It's time to own your beach home in the heart of Old Saybrook! This well-maintained mobile home is located within a 55+ coastal community. The home features two spacious bedrooms and an open-concept living and dining area. The kitchen boasts ample cabinets and vibrant color. Step through the sliding door to a bright built-in porch, perfect for relaxing. Recent updates include a new roof and a stackable washer and dryer, offering comfort and convenience in a move-in ready home. Enjoy easy single-level living, low maintenance, and close proximity to shopping, dining, highways, and Old Saybrook's shoreline attractions. Call today - this home won't last!

21 Harvey Dr, Old Saybrook
6 South St, Old Saybrook
$162,000
CLOSED Status ⋅ 24166874 MLS
Highest & Best by 3pm on 4/28! Move into your dream home by autumn! This exceptional lot is truly shovel-ready, and includes full plans for a beautifully designed 3-bedroom home with water views. All essential approvals and documentation are in place, including septic plans and B100, along with fully transferable building permits-saving you time and effort! Prefer your own design? You can easily customize while using the same footprint for a streamlined process. Current permits are valid through summer 2027, giving you flexibility to build on your timeline. Tucked away on a quiet dead-end road shared by just two other homes, this location offers both privacy and charm. Walk or bike to the water, Saybrook Point, and the vibrant downtown historic district of Old Saybrook. A rare opportunity to build with ease in a highly desirable coastal setting!

6 South St, Old Saybrook

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