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100 Sheffield St Unit A2, Old Saybrook
$625,000
2 Beds ⋅ 3 Baths ⋅ 24179634 MLS ⋅ The Cove BLDG.
Nestled within The Cove, a serene community on Old Saybrook's storied North Cove, this beautifully appointed townhouse offers the quintessential Connecticut shoreline lifestyle, where the Connecticut River meets the estuary and the ever-changing, breathtaking natural backdrop is your constant companion. The welcoming foyer has abundant closet space and a convenient half bath. The kitchen with granite counters and breakfast bar, dining room, and living room all share gorgeous cove views. The dining room flows naturally into the light-filled living room, appointed with built-in shelves and sliders that open to a private patio, making indoor-outdoor living effortless. Upstairs, two ensuite bedrooms provide comfort and privacy. The primary suite is a true retreat, with sliders to a private deck where captivating cove views greet you the moment you open your eyes, and a full bath with walk-in shower. The second bedroom features a walk-in closet and its own full bath with tub/shower. A designated laundry room completes this level. The finished lower level is ideal as a recreation room, home office, or media room--alongside a large storage room housing a brand new furnace and on-demand hot water heater. Launch your kayak directly on the river and paddle out to the protected cove. Kayaks can be stored in your garage, attached shed, or on town racks conveniently located at the end of Sheffield Street. Saybrook Point, The Kate theater, fine dining, and Main Street are all minutes away.

100 Sheffield St Unit A2, Old Saybrook
100 Dudley Ave Unit H42, Old Saybrook
$625,000
2 Beds ⋅ 3 Baths ⋅ 24167484 MLS ⋅ Sheltered Cove BLDG.
Coastal elegance meets low-maintenance living in this beautifully appointed townhouse-style 2 bedroom condominium, ideally situated within walking distance of charming downtown Old Saybrook. Located at Sheltered Cove, a coveted community, step inside an open concept floor plan with a living room showcasing custom cabinetry, fireplace and serene views of the tidal marsh that invite the outdoors in. A slider opens from the Living Room to your private patio-perfect for morning coffee or evening entertaining. The Kitchen offers granite counters, 2 sinks and plenty of storage. Gleaming hardwood floors throughout the 1st floor. The thoughtful two-story layout offers 2 generously sized ensuite bedrooms on the second level, each with its own private bath for ultimate comfort and privacy. Laundry is located between the two bedrooms. A finished basement provides flexible space for a home office, gym, or media room, plus ample storage to keep everything organized. Additional highlights include a detached 1 car garage, community pool, and clubhouse-ideal for enjoying the best of Connecticut shoreline living. Whether you're strolling to Main Street's boutiques and eateries or unwinding with marsh views from your patio, this home offers a rare blend of convenience, style, and tranquility.

100 Dudley Ave Unit H42, Old Saybrook
207 School House Rd, Old Saybrook
$615,000
4 Beds ⋅ 2 Baths ⋅ 24193207 MLS
A rare opportunity awaits to become the second owner of this lovingly maintained ranch on desirable Schoolhouse Road. Thoughtfully designed for comfortable one-level living, this spacious 2,149-square-foot home offers four generously sized bedrooms, wide hallways, gleaming hardwood floors, and central air conditioning. Step inside to a welcoming living room featuring a classic wood-burning fireplace and oversized windows that fill the space with natural light while overlooking the beautifully landscaped front gardens. The eat-in kitchen is equipped with stainless steel appliances and flows seamlessly into the expansive dining room-an ideal layout for holiday gatherings, dinner parties, and everyday entertaining. One of the home's standout features is the 280-square-foot, four-season sunporch, offering beautiful views of the private backyard and providing the perfect space to relax year-round. It is important to note the this sq. footage is not included in the Tax Record totals for the home. Situated on a picturesque 1.1-acre lot, this property also includes a partially finished basement with plenty of room for storage as well as an attached two-car garage. The home is freshly painted throughout with newly refinished hardwood floors, offering a bright, move-in-ready interior while providing the perfect canvas to make it your own. Offering space, quality, and exceptional care in a sought-after setting, this is a home you'll be proud to call your own.

207 School House Rd, Old Saybrook
120 Sandy Point Rd Unit 120, Old Saybrook
$615,000
2 Beds ⋅ 3 Baths ⋅ 24129742 MLS ⋅ Summerwood Condo BLDG.
Move right into this beautifully renovated 1,557 sq. ft. townhouse condominium in the highly desirable Summerwood on the Sound! This turnkey home offers 2 bedrooms plus a spacious third-floor loft-perfect for a home office or 3rd bedroom. Thoughtfully updated throughout, the home features hardwood flooring on all three levels, 2 1/2 beautifully renovated bathrooms, Andersen Windows, a Bosch High-Efficiency heat pump (2024), and a Rheem 50-gallon hot water heater (2024), new roof 2019. The open and inviting floor plan is filled with abundant natural light and features a cozy fireplace in the living room, creating the perfect space for relaxing or entertaining. The updated kitchen offers granite countertops, stainless steel appliances, and an ideal layout for everyday living and hosting family and friends. Enjoy seamless indoor-outdoor living with a private deck off the dining room. Summerwood on the Sound offers exceptional resort-style amenities including a private beach, paddle board/canoe racks, swimming pool, tennis courts, and pickleball courts. Located just minutes from downtown Old Saybrook, marinas, shopping, and dining, this meticulously maintained home offers the perfect blend of luxury, comfort, and low-maintenance coastal living. Nothing to do but move in and enjoy!

120 Sandy Point Rd Unit 120, Old Saybrook
208 Ingham Hill Rd, Old Saybrook
$615,000
3 Beds ⋅ 3 Baths ⋅ 24183646 MLS
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 applianced kitchen with newer refrigerator. First floor laundry and beautiful sunroom. House being sold "As Is". Please - Do not pull into driveway without appointment.

208 Ingham Hill Rd, Old Saybrook
21 Baum Ave, Old Saybrook
$600,000
2 Beds ⋅ 2 Baths ⋅ 24190986 MLS
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 with family & friends. A spacious patio sets the stage for effortless entertaining, while the oversized shed provides exceptional storage for beach gear, bikes, lawn equipment, & more. Step inside & you'll find a beautifully maintained 2-bed, 2-full bath home that's just as inviting as the backyard, creating the perfect blend of warmth, character, and comfort. With hardwood floors throughout, a renovated kitchen, & energy-efficient mini-split systems, the layout is made for a weekend retreat or year-round escape. Perfectly situated just mins from downtown Old Saybrook, you'll enjoy convenient access to charming boutiques, local restaurants, marinas, golf courses, fitness studios, & public beaches-making it easy to embrace the best of CT's shoreline lifestyle. Whether you're hosting parties, unwinding after a day by the water, or exploring everything Old Saybrook has to offer, this thoughtfully updated, move-in-ready home delivers the perfect combination of comfort, convenience, and coastal charm. Looking for an investment? Its desirable location & turnkey appeal make it an ideal candidate for an Instagram-worthy vacation getaway/short-term rental to add to your portfolio. Don't let this one sail away!

21 Baum Ave, Old Saybrook
725 Boston Post Rd, Old Saybrook
$600,000
3 Baths ⋅ 24111400 MLS
Location - Prime Boston Post Road Frontage! An incredible opportunity awaits in the heart of downtown Old Saybrook with this turn-key mixed-use property, ideally situated on bustling Route 1. Zoned B-2, the 2,140 sq ft commercial space offers endless possibilities for a wide range of businesses, from wellness and spa services to professional offices or retail.The main level of the commercial unit has an open-concept space, including a welcoming reception area, stylish waiting room, and a spacious shared spa or service area - all enhanced by high-end lighting and exquisite tile finishes. A kitchenette provides functionality for staff breaks or private treatments, while a half bath completes the layout.The fully remodeled lower level boasts a large open common space, two versatile rooms ideal for treatment areas or offices, and a utility zone with laundry and Bilco door access, perfect for deliveries. The residential unit offers privacy and charm, complete with a fenced patio and pergola for outdoor enjoyment. Inside, you'll find a beautifully updated kitchen with Corian counters, bar seating, and an open layout perfect for entertaining. The first floor includes a bedroom and full bath with floor-to-ceiling , while the 2nd level spans the length of the building that includes 3 spacious bedrooms all with walk-in closets plus an updated full batn.bath.Updates New windows, efficient heating and cooling units, updated electrical and a commercial fire alarm system.

725 Boston Post Rd, Old Saybrook
32 King St, Old Saybrook
$599,000
4 Beds ⋅ 2 Baths ⋅ 24196621 MLS
You are walking distance to shopping, restaurants and public transportation from this in-town cape with 4 bedrooms, 2 full baths, hardwood floors, oversized two car garage and an amazingly private backyard and large deck. Oil heat and a full dry basement complement this nicely proportioned 1643 square foot home. Town Beach and Long Island Sound are only a short drive away.

32 King St, Old Saybrook
25 Pond Rd, Old Saybrook
$595,000
2 Beds ⋅ 2 Baths ⋅ 24154312 MLS
In town location! Close to Main Street and to several shopping centers for you to enjoy all that Old Saybrook has to offer: shops, restaurants, The Kate Cultural Art Center, library, parks & rec, and more! This 2 bedroom 2 bath ranch style home has beautiful hardwood floors through out. The natural light streams in through the bay window of the classic living/dining room, where a dutch door opens onto a back deck and private yard. The family room, off the country styled eat-in kitchen has a large gas fireplace and sliders to a patio. The primary bedroom has vaulted ceiling and wooden beams. A second bedroom has a walk in cedar closet. All the rooms are large, bright spaces. The house was originally designed as a 3 bedroom home, the owner absorbed a small bedroom to expand the primary. A two car garage along with a seperate work shop with wood stove completes the property. Professional landscaping and wooden fencing has kept this corner lot quiet and private. The solidly built home awaits your personal touches - add to the already charming layout and New England finishes. Make this your new home!

25 Pond Rd, Old Saybrook
175 Ferry Rd Unit 4, Old Saybrook
$585,000
2 Beds ⋅ 3 Baths ⋅ 24151928 MLS ⋅ Eden Harbour BLDG.
Welcome to 175 Ferry Road, Unit 4 at Eden Harbor, a beautifully maintained and thoughtfully designed 2-bedroom, 2.1-bath townhouse in an over 55 active adult community, offering comfort, flexibility, and effortless living in one of Old Saybrook's most convenient locations. With a versatile floor plan, quality finishes throughout, and an attached garage, this home lives more like a private residence than a condo. Step inside to find hardwood floors that flow through the main living areas, creating a warm and welcoming first impression. The spacious living room is the heart of the home, featuring a propane fireplace and abundant natural light. Sliding glass doors open directly to a private back patio, extending your living space outdoors and offering a peaceful setting for relaxation. The updated kitchen is both stylish and functional, appointed with granite countertops, stainless steel appliances, ample cabinetry, and generous prep space. Just off the kitchen is a separate laundry room. One of the standout features of this home is the first-floor bedroom with a full bath, offering exceptional flexibility. Ideal for guests, a home office, or single-level living, this layout accommodates a variety of lifestyles and long-term needs. A convenient half bath on the main level further enhances everyday comfort and entertaining ease. Upstairs, you'll find the second bedroom suite, complete with its own ensuite full bath, providing privacy and comfort.

175 Ferry Rd Unit 4, Old Saybrook
2 Half Penny Ln, Old Saybrook
$580,000
3 Beds ⋅ 2 Baths ⋅ 24192318 MLS
This charming home offers the perfect blend of charm, comfort, and opportunity. Filled with warmth, character, and endless potential, this well-maintained home features one bedroom and a full bath on the main level and 3 additional bedrooms upstairs. An inviting open floor plan where the kitchen flows seamlessly into the dining area and family room. The kitchen has granite counter tops, island and double ovens. A cozy living room with a classic fireplace creating the perfect gathering space. Hardwood floors throughout, while the sunroom provides a bright retreat for reading or relaxing. The fully finished basement offers flexible living space ideal for a family room, home office, gym, or playroom. A spacious private yard includes a shed and outdoor shower set on a corner lot is perfect for outdoor barbecues or Summer evenings. Generator ready. Move right in and enjoy its charm while adding your own personal touches over time. Ideally located just minutes from Old Saybrook's vibrant Main Street, boutique shopping, restaurants, marinas, two town beaches, and convenient highway access, this home offers the very best of shoreline living! Come make this home your own!

2 Half Penny Ln, Old Saybrook
48 Great Hammock Rd, Old Saybrook
$575,000
2 Beds ⋅ 1 Baths ⋅ 24131179 MLS
Welcome to this charming one floor ranch! This home features hardwood floors throughout, bright living room with fireplace, built-ins and wonderful for entertaining, cozy family room with fireplace, built-ins perfect for relaxing or an office, updated kitchen with granite countertops and stainless steel appliances, 2 spacious bedrooms with plenty of closet space, inviting outdoor patio perfect for barbecue while the corner lot provides a spacious yard for outdoor enjoyment. Additional highlights include an 8 year old roof, a full unfinished basement, a newer septic system/WPCA compliant and a two-car garage. Ideally located within walking distance to two town beaches and Main Street to enjoy restaurants and shopping! This home offers convenience, comfort and shoreline living at its best! Close to highways, trains and amenities! Come take a look!

48 Great Hammock Rd, Old Saybrook
14 Cedarwood Ln, Old Saybrook
$570,000
3 Beds ⋅ 2 Baths ⋅ 24187465 MLS
BACK ON MARKET - BUYER GOT COLD FEET! 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 private Cornfield Point beach with deeded beach rights. Inside you'll discover a bright, open-concept floor plan that flows from the living area into the eat-in kitchen, creating an inviting space ideal for both everyday living and entertaining. The primary bedroom features a private en-suite half bathroom, while two additional bedrooms offer flexibility for family, guests, or a home office. From the gleaming hardwood floors and freshly painted walls to the thoughtfully renovated kitchen and bathrooms, every detail has been attended to - just move in and enjoy. Where this property truly shines is outside. The oversized 2-car garage is a rare find, offering abundant space for vehicles, a workshop, or extra storage. The private backyard is your own personal sanctuary, complete with a hot tub, a private outdoor shower and breathtaking marsh views that never get old. Whether you're rinsing off after a day at the beach or unwinding under the stars, this outdoor space is very special. The partially finished basement provides add'l living space, and a large storage room. The major items have been taken care of for you- septic system is only 9 years old and the roof was replaced in '24.

14 Cedarwood Ln, Old Saybrook
175 Ferry Road Unit 10, Old Saybrook
$570,000
2 Beds ⋅ 2 Baths ⋅ 24122397 MLS ⋅ Eden Harbour BLDG.
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 built-in custom bookshelves enhancing the home's airy, connected feel, creating a warm and welcoming atmosphere. In addition, an open dining room, perfect for formal dining or flexible space. The spacious primary ensuite is complete with a walk-in closet. A well situated second bedroom provides easy access to an additional full bath. Conveniences include a separate main level laundry room, ample closet space, unfinished lower-level walk-out basement for storage, and an easily accessed attached two-car garage. Enjoy being just steps from the water and marina, and moments from downtown Old Saybrook's vibrant shops, cafes, and restaurants. Don't wait! This is shoreline living with comfort, style, and convenience all brought together in a premier 55+ community.

175 Ferry Road Unit 10, Old Saybrook
254 Hidden Cove Rd Unit 254, Old Saybrook
$570,000
2 Beds ⋅ 3 Baths ⋅ 24130577 MLS ⋅ Summerwood Condo BLDG.
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 counter tops, Bosch appliances, Hard wood floors throughout, Upstairs, adding one full Bathroom creating on-suite Primary room, also moving the laundry to the second floor. two generously sized bedrooms provide peaceful sanctuaries, while the updated bathrooms offer stylish convenience. Enjoy the best of shoreline living with access to amenities including: A private beach just moments away Community swimming pool for sunny summer days Tennis and pickleball courts for active lifestyles Beautifully maintained grounds in a tranquil, wooded setting Located just minutes from Old Saybrook's charming downtown, you'll love the proximity to boutique shopping, fine dining, and the scenic Connecticut shoreline. Whether you're downsizing, investing, or searching for a vacation home, this turnkey property offers the perfect blend of comfort, leisure, and location.

254 Hidden Cove Rd Unit 254, Old Saybrook
100 Dudley Ave Unit H43, Old Saybrook
$570,000
2 Beds ⋅ 3 Baths ⋅ 24125908 MLS ⋅ Sheltered Cove BLDG.
Beautiful Condominium offered in Sheltered Cove. Set within the serene, meticulously maintained grounds of Sheltered Cove, this charming two-story condominium offers a rare chance to enjoy North Cove and the Connecticut River. Expansive lawns, picturesque views and tranquil surroundings create a setting that feels both private and welcoming. Residents enjoy a newly remodeled swimming pool, clubhouse, and ample guest parking. Located on the southern end of the association, along the estuary, this lovingly kept home features a kitchen that opens seamlessly to the dining area and a warm, light living room with a wood-burning fireplace framed by custom-built-in cabinets. A large glass slider with a custom wood valance opens to a private patio and garden overlooking lush landscaping, home to perennials, ornamental grasses and the resident osprey pair, Romeo and Juliet. Upstairs, two bedrooms provide generous closets. The primary suite includes a full bath and sweeping seasonal views. Near the guest bath, a full laundry and double-door closet offer storage, while another closet has been transformed into a home office work station. A one-car garage adds storage and convenience. Sheltered Cove offers lush grounds, mature trees, and easy access to beaches, marinas, and Old Saybrook's vibrant downtown-with shops, dining, and the Kate Hepburn Cultural Arts Center-all just a short distance away. This unit is priced to sell "as is".

100 Dudley Ave Unit H43, Old Saybrook
4 Sea View Ave, Old Saybrook
$569,000
2 Beds ⋅ 1 Baths ⋅ 24094203 MLS
Looking for a perfect respite by the sea? Charming Coastal Ranch with Stunning Marsh Views - Old Saybrook, CT Nestled in the highly desirable coastal town of Old Saybrook, this adorable 2-bedroom, 1-bath ranch offers a perfect blend of charm, convenience, and breathtaking marsh and water views. Thoughtfully designed to maximize space and natural light, this home is an ideal retreat for those seeking tranquility with easy access to local amenities. Step into the vaulted living area, where skylights and large windows flood the space with sunlight, creating an airy and inviting atmosphere. The open layout enhances the home's charm, offering seamless flow between the living space and kitchen. A wood burning fireplace will make chilly nights cozy. Outside, a cozy deck provides the perfect spot to take in the serene marsh views, watch wildlife, and enjoy the peaceful coastal breeze. The nicely landscaped lot adds to the home's appeal, offering a picturesque setting with mature plantings and seasonal beauty. Additional features include a private driveway and a one-car garage, providing convenience and ample storage. Put your finishing touches on this lovely home!

4 Sea View Ave, Old Saybrook
76-1 River St W, Old Saybrook
$565,000
3 Beds ⋅ 2 Baths ⋅ 24164630 MLS
76-1 River Street West! This is an incredible opportunity, less than a quarter mile to Old Saybrook Main Street and Amtrak train station. A cozy kitchen, dining and living open to an expansive great room with vaulted, beamed ceiling. There is a generous first-floor bedroom and an adjacent full bath. Upstairs find two larger bedrooms and a second full bath. The basement has an elevated ceiling, ideal for future bonus space, with laundry and mechanicals as well as an easy to access 2-car garage. Originally built as an electric home, it was converted to oil heat. Two oil tanks afford bulk purchases. A wall-mounted AC unit keeps the main level cool. Window units are used on the second floor. An expansive deck runs the length of the home overlooking the tidal marsh and its incredible diversity of birds and wildlife. Flood insurance is $1057 annually and the home sits well elevated above the marsh. The home will benefit from new exterior siding, trim and updated flooring. Completely wonderful, immaculate interior with stunning potential for the next homeowner. Sidewalks run from the end of River Street to Saybrook Point and beyond. A uniquely quiet location just a stone's throw from the train station making this an idyllic weekend retreat or just right year-round home.

76-1 River St W, Old Saybrook
175 Ferry Rd Unit 3, Old Saybrook
$565,000
2 Beds ⋅ 2 Baths ⋅ 24128273 MLS ⋅ Eden Harbour BLDG.
You will never need to move again! Eden Harbour, an elegant and vibrant 55+ Condominium Community is just across the street from the Connecticut River and marinas. This amazing one level unit has an open floor plan, hardwoods throughout and is fully accessible. Enter through a gorgeous foyer which leads to a beautiful Living Room and Dining Area featuring stately columns, gas fireplace, and sliders to a private deck. The charming eat-in kitchen has granite counters, island with seating and stainless appliances. The primary suite includes a walk-in closet and private bath with roll-in shower and marble topped vanity. A second generous bedroom/office or den is located next to a full bath. The main level laundry, and attached 2-car garage with ramp add total convenience. The full basement provides excellent storage. This home is extremely well-maintained and move-in ready! It is minutes from beaches, marinas, shops, restaurants, train service to NYC/Boston, and more. Public transportation stops at the complex and gives you access to Shoreline towns. Located approximately 2 hours from Boston and New York You will love living the Good Life in the wonderful, Historic Town of Old Saybrook, Connecticut!

175 Ferry Rd Unit 3, Old Saybrook
46 Farview Ave, Old Saybrook
$560,000
3 Beds ⋅ 2 Baths ⋅ 24196117 MLS
Location, location, location. Enjoy shoreline lifestyle in one of Old Saybrook's in demand neighborhoods. Level corner lot. Solid home ready for you to make it your own. Eight total room, three bedrooms, two full baths one updated. Fireplace in the Living room. Sunroom, one car attached garage. Full unfinished basement. Incredible opportunity to create the home of your dreams. Enjoy coastal living in Old Saybrook, around the corner from Kavanaugh Park, Trask Road area with tennis, splash pad, playground, ball field, basketball, picnic area. Short walk to beaches, Main Street, Schools Library and The Kate theatre. Close to train station for easy commute.

46 Farview Ave, Old Saybrook
167 Ingham Hill Rd, Old Saybrook
$560,000
3 Beds ⋅ 2 Baths ⋅ 24156496 MLS
Privacy, acreage, and beach-town access converge in this 1.09-acre Ingham Hill property in Old Saybrook. Built in 1984 by Bob Day and offered for the first time by the original owner, this Colonial delivers rare space along the Connecticut Shoreline just minutes from beaches, marinas, and downtown amenities. With under 1,400 square feet, two full baths, and an attached garage, the flexible layout includes a first-floor bedroom and full bath for convenient one-level living, guest accommodations, or home office use. The living room features a fireplace and sliders to the backyard, creating seamless indoor-outdoor access to the level yard. AA-1 zoning and generous lot size provide versatility for outdoor living, gardening, recreation, or future expansion. Approximately 1.5 miles to Harvey's Beach and Old Saybrook Town Beach, and about 2 miles to Saybrook Point marinas and waterfront dining. Close to The Kate (Katharine Hepburn Cultural Arts Center), Liv's Oyster Bar, Walt's Food Market, and Mystic Market West. Easy access to Old Saybrook Amtrak Station and Shore Line East commuter rail service to New Haven, New London, and NYC. A rare opportunity to enjoy Connecticut shoreline living with land, privacy, and direct access to beaches, boating, dining, and rail.

167 Ingham Hill Rd, Old Saybrook
53 Chalker Beach Rd, Old Saybrook
$550,000
3 Beds ⋅ 1 Baths ⋅ 24186997 MLS
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 flooring throughout, sun filled bay windows, garden shed, open sunny lot, and new high efficiency propane furnace. Enclosed sunroom with glass windows and sliding glass door provides additional respite space. Chalker Beach remains one of Connecticut's sought-after private waterfront communities on Long Island Sound in Old Saybrook, Connecticut. Neighbors dating back for generations have chosen Chalker Beach-not just for a home, but as a lifestyle investment. Residents enjoy access to a private beach, 2 community club houses, foosball, play scape, baseball field, basketball court, and the Chalker Beach Store/Cantina. This is a community built around outdoor living with movie nights at the beach, neighborly connection, and carefree summers. No car needed. Everything is walkable. The kind of close-knit community that is increasingly rare. Do not miss an opportunity to own a home along the Long Island Sound.

53 Chalker Beach Rd, Old Saybrook
143 Sandy Point Rd Unit 143, Old Saybrook
$550,000
2 Beds ⋅ 3 Baths ⋅ 24109027 MLS ⋅ Summerwood Condo BLDG.
Welcome to SummerWood on the Sound, a premier waterfront community in Old Saybrook offering resort-style living on the Long Island Sound. This beautifully maintained 2-story condo with a 3rd-floor sleeping loft is perfect for year-round living or a cozy coastal getaway. Features include 2 bedrooms, with a primary suite and en-suite full bath, an updated guest bath, and a half bath on the main level. The kitchen showcases new quartz countertops, and water views are visible from every window, with east-facing exposure for breathtaking sunrises. Enjoy outdoor living on the private deck with an electric awning, ideal for morning coffee or entertaining. SummerWood on the Sound offers exceptional amenities: Private beach Kayak & paddleboard racks Tennis, pickleball & basketball courts In ground pool Don't miss this opportunity to own in one of Connecticut's most desirable shoreline communities.

143 Sandy Point Rd Unit 143, Old Saybrook
118 Sandy Point Rd Unit 118, Old Saybrook
$540,000
2 Beds ⋅ 2 Baths ⋅ 24079450 MLS ⋅ Summerwood Condo BLDG.
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 an updated half bath on the first floor. The second floor features the primary bedroom with views of the tidal marsh, en suite bath and two large walk in closets for personal items and extra storage. There is also a guest bedroom on the second floor. The versatile third floor loft area provides flexible space for an office, family or guests. Located in Summerwood, this community offers resort style amenities for your enjoyment, including a large pool, private sandy beach on Long Island Sound, tennis and pickle ball courts. Enjoy the lifestyle. Flood insurance is provided as part of the HOA dues.

118 Sandy Point Rd Unit 118, Old Saybrook
44 Coulter St, Old Saybrook
$531,000
3 Beds ⋅ 1 Baths ⋅ 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
46 Maple Ave, Old Saybrook
$530,000
4 Beds ⋅ 2 Baths ⋅ 24124235 MLS
Old Saybrook Multi-Family with ADU Steps to the South Cove. Seize a rare opportunity to own this highly versatile, multi unit in the heart of sought-after Old Saybrook. Perfectly situated just steps from scenic South Cove, this spacious multi-family home offers unmatched convenience. Leave the car behind as you enjoy a short stroll to vibrant downtown Old Saybrook, and easily access the Shoreline commuter rail for hassle-free travel. The main dwelling provides a comfortable and expansive living experience, centered around a large open-concept living and dining space-perfect for hosting gatherings. This unit features a light-filled eat-in kitchen, two generous bedrooms, and an additional office or den, providing the flexibility for a quiet workspace or a cozy retreat. A separate, accessory dwelling unit (ADU) offers endless possibilities. Ideal for keeping loved ones close, this private space can also generate income as a lucrative Airbnb, housing for a traveling nurse, or a guest suite. The ADU has its own kitchen, living/dining area, a full bath, and a private sleeping area, all with the added convenience of two separate entrances. The second-floor unit features a large living room with hardwood floors, a bright eat-in kitchen, two bedrooms, a full bathroom, and a dedicated office space. Whether looking for a savvy investment or flexible living arrangement...this is it.

46 Maple Ave, Old Saybrook
55 Woodland Dr, Old Saybrook
$525,000
4 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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
67 Middletown Ave, Old Saybrook
$520,000
3 Beds ⋅ 1 Baths ⋅ 24160518 MLS
This charming year-round cottage-style home is tucked within the Saybrook Manor Beach Association and offers the perfect blend of coastal simplicity and modern comfort. Just a short stroll from two bathing beaches and a clubhouse for community events, this home captures the relaxed rhythm of shoreline living. The interior has been tastefully updated throughout for today's lifestyle providing a floor plan that is open and efficient with 2 bedrooms on the first floor and an attic bedroom upstairs. Outdoor living is just as important on the shoreline, and your private, covered deck extends the living space along with an outdoor shower--essential for beach life. The detached garage-size storage shed has electricity and provides ample space to store a golf cart, bikes, kayaks and all your shoreline needs. This coastal retreat is small in scale but rich in lifestyle making everyday feel like a getaway.

67 Middletown Ave, Old Saybrook

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