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18 Quarry St, Old Saybrook
$510,000
4 Beds ⋅ 2 Baths ⋅ 24137642 MLS
Downtown Old Saybrook location offers true small town charm, a first floor primary bedroom, and two full baths. Tucked away on a quiet dead end street just steps to sidewalks, this classic New England style home presents a renovation opportunity in one of the shoreline's most desirable neighborhoods. Walk to Trask Park, the Old Saybrook Library, local shops, and favorites like Walt's Market. Enjoy performances at The Kate, relax at Harvey's Beach or Town Beach, spend the day boating from Safe Harbor Marina, or stroll the waterfront at Saybrook Point. Fenwick Golf Course and marinas are just minutes away. Amtrak service nearby provides convenient access to New York and Boston, making commuting or weekend travel simple. Set on a cleared half acre with mature landscaping and blooming perennials, the property offers privacy and curb appeal. Inside, the spacious living room with fireplace flows into a large eat in kitchen with room to update and make it your own. First floor primary bdrm provides everyday convenience and flexibility, and with 2 full baths, the layout works beautifully for guests, family, or comfortable one level living. A three season screened porch extends the living.space and invites relaxed summer evenings. Solid bones, exceptional walkable location, and long term value in one of Connecticut's most desirable shoreline towns. Updates could certainly be done, which creates opportunity. Rather than paying a premium for someone else's design choices, make your ow

18 Quarry St, Old Saybrook
9 Farview Ave, Old Saybrook
$500,000
3 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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
133 Sandy Point Rd Unit 133, Old Saybrook
$430,000
2 Beds ⋅ 2 Baths ⋅ 24128689 MLS ⋅ Summerwood Condo BLDG.
Summerwood on the Sound - Coastal Living at Its Best! Welcome to 133 Sandy Point Road, a beautiful condominium in the desirable Summerwood on the Sound community. Offering 1,288 sq. ft. of open-concept living, this 2-bedroom, 1.5-bath home blends comfort, style, and the ultimate shoreline lifestyle. Step inside to a bright and inviting floor plan with hardwood floors on the main level and an easy flow to the spacious deck, perfect for entertaining or relaxing outdoors. The new windows fill the home with natural light, while thoughtful upgrades include a walk-in shower, new hot water heater & dehumidifier for peace of mind. Upstairs, two well-sized bedrooms with plush carpeting provide a cozy retreat. Life at Summerwood on the Sound means more than just a home-it's a lifestyle. Enjoy access to a private beach on Long Island Sound, complete with kayak and paddleboard racks, plus a community inground pool, tennis courts, and racquetball courts. Whether you're searching for a year-round residence or a seaside getaway, this home delivers the perfect blend of upgrades, comfort, and coastal amenities. "Well-maintained complex with new roof (2019)"

133 Sandy Point Rd Unit 133, Old Saybrook
227 Essex Rd, Old Saybrook
$410,000
3 Beds ⋅ 1 Baths ⋅ 24128935 MLS
Nestled on a .93 Acre corner lot this 3 Bedroom Ranch offers one floor living. Fireplace in Living Room, Eat-In Kitchen, Vinyl siding, a four year old roof plus gutter guards for easy maintenance. The Lower Level features a Den/Family Room with a built-In Bar. Enjoy the convenience of a 2 bay garage with door openers during inclement weather. Easy access to Rt 9, I95 or the train station for the commuter.

227 Essex Rd, Old Saybrook
34 Sunset Ave, Old Saybrook
$400,000
2 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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
1057 Boston Post Rd, Old Saybrook
$400,000
1 Baths ⋅ 24115772 MLS
This is your chance to own the most quintessential building in Old Saybrook! Not only is it in a busy, high traffic area on Boston Post Road, it is also in an idyllic setting on the Oyster River. The property includes a working commercial kitchen and is turnkey, equipped with display cases, refrigerators, ovens, and more. The building is also fully insulated with HVAC heating & cooling for year round operation. Formerly used as combination of 'grab & go' food service, bakery, and retail farm stand marketplace. Many possibilities at Old Saybrook's beloved farm stand, including office & retail uses. B3 Zoning. This opportunity is not to be missed!

1057 Boston Post Rd, Old Saybrook
30 Sunset Ave, Old Saybrook
$395,000
4 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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
6 College St, Old Saybrook
$379,000
1 Beds ⋅ 1 Baths ⋅ 24129311 MLS
Discover this quintessential cottage-style home, perfectly located between downtown Old Saybrook-with its boutique shops, restaurants, and the renowned Kate Theatre-and the scenic Saybrook Point. Just minutes from the shoreline, you'll enjoy easy access to Old Saybrook's desirable beaches, making this property a true coastal retreat. This home offers a wide range of possibilities: an excellent alternative to renting, a vacation getaway, an Airbnb or investment rental, or simply your own peaceful year-round residence. The beautifully maintained landscaping and updated rear deck create the perfect setting for summer entertaining and outdoor relaxation. Inside, the home is a legal one-bedroom but also includes a private additional room ideal for a guest bedroom, office, art studio, or gym. The living room is filled with tons of natural light and opens directly to the dining area and kitchen. Recent updates add to the appeal and peace of mind, including new vinyl siding and gutters, a new bathtub, new composite pull-down blinds throughout and an updated sump pump system. Whether you're looking for a cozy coastal haven or a flexible investment property, this Old Saybrook gem delivers charm, convenience, and endless potential.

6 College St, Old Saybrook
61 Ingham Hill Rd, Old Saybrook
$365,000
1 Beds ⋅ 2 Baths ⋅ 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
Old Saybrook
$358,000
1 Beds ⋅ 1 Baths ⋅ 24121499 MLS
Secluded Country Farmhouse on 2+ Acres: Discover your private oasis just minutes from the beach, parks and all shopping/commuting conveniences. This level, tree-lined property offers bucolic views, with a picturesque pond abutting the lot for a true nature escape. __ Key Features: Over 2 acres of flat, usable land framed by mature trees - Glimpse the tranquil pond and enjoy complete privacy - Two drilled wells (one new in 2021)-formerly a small farm site __ Endless Possibilities: This farmhouse home is a canvas waiting for your personal touch. Refresh the kitchen and bath at your own pace and watch your investment grow. The existing wood-burning stove area lends cozy charm, or reclaim that space for a second bedroom as was previously -flexibility is yours. __ Sunlit Porch & Future Family Room: Step into the three-season, window-lined sunroom/mud area with hardwood floors and exposed beam ceilings. Gas piping is already in place, making it simple to convert this bright spot into an all-season family room you'll never want to leave. __ Embrace the perfect blend of serenity, convenience, and potential. Schedule your tour today and imagine life in this coastal haven. Properties like this are seldom available, and the prospect for value growth is exceptional.

Old Saybrook
195 Bokum Rd, Old Saybrook
$350,000
3 Beds ⋅ 2 Baths ⋅ 24146492 MLS
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 bedrooms with classic wide-board floors, 2 full baths, a 2-car detached garage, and a large, character-filled barn. Mechanical systems have been well-maintained, providing a solid foundation for the next chapter. While the home requires significant renovation, including a new roof and replacement of the basement stairs, it presents a strong canvas for those with vision and skill. Access to the basement is via the Bilco doors on the driveway side only. This is a true project property with exceptional land, privacy, and authentic historic charm. The house itself is not on the Historic Registry; however, the barn may be. Buyers are encouraged to perform due diligence. For the right buyer, this is a rare opportunity to restore and reimagine a special property, breathing new life into a home with timeless character and an extraordinary setting. Sellers are open to all realistic offers. Cash, an FHA 203K Loan, or a Renovation Loan would be the ideal way to purchase this property.

195 Bokum Rd, Old Saybrook
254 Main St, Old Saybrook
$350,000
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
40 A Ayers Point Rd, Old Saybrook
$320,000
24141549 MLS
WELCOME TO OLD SAYBROOK/SHORELINE LIFESTYLE /BEACHES/SHOPS/RESTAURANTS AND FAMOUS KATE THEATER/GREAT OPPORTUNITY TO BUILD YOUR DREAM HOME IN ASTABLISHED AYERS POINT NEIGHBORHOOD.APPROVED RESIDENTIAL BUILDING LOT.GREAT LOCATION BETWEEN OLD SAYBROOK DOWNTOWN AND TOWN OF ESSEX/ AA-1 ZONIG/SURVEY AVAILABLE. CALL-PREVIEW-BUILD :)

40 A Ayers Point Rd, Old Saybrook
3 4th Ave, Old Saybrook
$309,000
3 Beds ⋅ 1 Baths ⋅ 24093798 MLS
This home offers the one-level living you've been searching for! With a bit of repair work and thoughtful updates, you can transform this space into your perfect home. The property features a spacious backyard, complete with a generously sized outdoor shed for added storage and convenience. Close to marina, restaurants and highway access. Short drive to the beach!

3 4th Ave, Old Saybrook
124 Old Boston Post Rd, Old Saybrook
$299,000
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 ⋅ 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
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
123 Elm St Unit 1200, Old Saybrook
$68,000
1 Baths ⋅ 24155283 MLS
Beautifully updated commercial office space offering approximately 900 square feet on the second floor. This bright and professional unit features a recently installed heating and A/C system (2025), providing efficient year-round comfort. The space is well-maintained, thoughtfully updated, and filled with natural light, creating an inviting and productive work environment. Located in a quiet, professional setting with plenty of on-site parking, this office is ideal for professional services, wellness providers, creatives, or other commercial uses seeking a clean, turnkey space in a peaceful atmosphere.

123 Elm St Unit 1200, Old Saybrook

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