Homes for Sale near Waterside School

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  /24

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,681 Sq Ft

  100 Old Mill Ln, Stamford, CT 06902

  Located on a peaceful cul-de-sac in Stamford's desirable Westover neighborhood, this spacious 4-bedroom, 2.5-bath Contemporary blends comfort and style on 1.77 acres. The sun-filled living room features vaulted ceilings, skylights, a fireplace, and hardwood floors. A separate family room offers a second fireplace, wet bar, and vaulted ceilings-ideal for entertaining. The formal dining room

  Dannel Malloy NestSeekers International

  100 Old Mill Ln, Stamford, CT 06902
• 

  

  

  /30

  $895,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  7 Chestnut St, Darien, CT 06820

  Sun-drenched and brimming with character, this home resides on a quiet, sought-after street in the heart of Darien. A welcoming front porch sets the tone, inviting you into a home that blends timeless charm with modern sophistication. Inside, an expansive living room flows seamlessly into the dining room, enhanced by classic pocket doors, while the modern kitchen opens to a spacious new

  Nellie Snell William Raveis Real Estate

  7 Chestnut St, Darien, CT 06820
• 

  

  

  /38

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft

  88 Pine Hill Ave, Stamford, CT 06906

  Welcome to 88 Pine Hill Avenue - a beautifully updated home that blends warmth, style, and convenience in the heart of Glenbrook. Step inside and be greeted by newly refinished hardwood floors that flow seamlessly throughout the home. The spacious living room, anchored by a charming fireplace and framed by a picture window, is filled with natural light and perfect for both everyday living and

  Catherine Richardson William Pitt Sotheby's Int'l

  88 Pine Hill Ave, Stamford, CT 06906
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  /24

  $449,000

  • 1 Bed
  • 1.5 Baths
  • 1,066 Sq Ft

  2437 Bedford St Unit F20, Stamford, CT 06905

  Nestled in a serene private enclave, this meticulously maintained condominium offers the perfect blend of luxury and convenience in one of Stamford's most sought after downtown locations. Enjoy the best of both worlds: a peaceful retreat just moments from the vibrant heart of the city with access to world class dining, shopping and entertainment. This light filled home features expansive windows

  Aimee Sciglimpaglia Keller Williams Prestige Prop.

  2437 Bedford St Unit F20, Stamford, CT 06905
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  /40

  $4,650,000

  • 5 Beds
  • 6 Baths
  • 7,833 Sq Ft

  72 Old Kings Hwy S, Darien, CT 06820

  Exceptional NEW CONSTRUCTION - Walk to Town - Experience refined luxury living in this custom-built home by V&A Construction Inc., a respected local builder highly regarded for exceptional craftsmanship, meticulous attention to detail and upscale finishes. Set near Great Island and Pear Tree Point Beach, this home offers the best of coastal living with the ease of everyday convenience, just a

  Katherine Kuras BHHS Darien/New Canaan

  72 Old Kings Hwy S, Darien, CT 06820
• 

  

  /40

  $3,300,000

  • 4 Beds
  • 4.5 Baths
  • 5,051 Sq Ft

  17 Brushy Hill Rd, Darien, CT 06820

  Perched high above the Goodwives River, this stunning Mid-Century Modern home offers sophisticated living in an extraordinary natural setting. Walls of floor-to-ceiling glass invite the outdoors in, seamlessly blending interior spaces with the serene beauty of the 1.8-acre private landscape. Reimagined by renowned architectural firm Joeb Moore + Partners, highlights include a dramatic

  Carolyn Brook William Pitt Sotheby's Int'l

  17 Brushy Hill Rd, Darien, CT 06820
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  /36

  $13,750,000

  • 6 Beds
  • 8 Baths
  • 9,189 Sq Ft

  411 Stanwich Rd, Greenwich, CT 06830

  Welcome to Mead Farm - exquisitely renovated and transformed midcountry Greenwich estate that blends historic character with modern luxury. Set on nearly 6 acres in a 2 acre zone, this 9,189 SF residence offers 6 bedrooms, 6 full and 2 half baths. A recent multi-year renovation by renowned designer Thom Filicia, paired with award-winning landscaping by James Doyle, elevates the property to a rare

  Amanda Bates Houlihan Lawrence

  411 Stanwich Rd, Greenwich, CT 06830
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  /21

  $3,500,000

  • 2 Beds
  • 3.5 Baths
  • 2,772 Sq Ft

  4 Sound Shore Dr Unit 24, Greenwich, CT 06830

  This sophisticated top-floor residence in the exclusive, guard-gated Waterford Association offers a rare opportunity to experience unparalleled waterfront living. With unobstructed, ever-changing views of Long Island Sound as your daily backdrop, this expansive penthouse combines timeless elegance with exceptional comfort.A gracious foyer opens into an oversized living room with fireplace and

  Lisa Stugart Brown Harris Stevens CT, LLC

  4 Sound Shore Dr Unit 24, Greenwich, CT 06830
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  /13

  $795,000

  • 2 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  1465 E Putnam Ave Unit 326, Old Greenwich, CT 06870

  Fabulous 2 Bedroom 1.5 bath light filled condo with private deck overlooking a well maintained park-like courtyard with a pond. A private entry leads you into a large over-sized living room with floor to ceiling windows, dining area, half bath, kitchen, and laundry. The second floor offers a large primary bedroom with 2 closets, ample sized second bedroom, along with a large full bathroom. Access

  Daniel DiPaolo BHHS New England Properties

  1465 E Putnam Ave Unit 326, Old Greenwich, CT 06870
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  /10

  $7,995,000

  • 8 Beds
  • 11.5 Baths
  • 10,646 Sq Ft

  68 Dearfield Dr, Greenwich, CT 06831

  Perched high on a hill in downtown Greenwich, 66 Dearfield is unparalleled in its grandeur with 10,646 square feet of luxury living spanning 4 floors. Close to Greenwich Library, Greenwich Avenue, the train and all downtown amenities. This exquisite colonial boasts stone chimneys with extra height ceilings on each floor. Upon entry, the 2 story foyer nestled between the living room and dining

  Nina Frandson BHHS New England Properties

  68 Dearfield Dr, Greenwich, CT 06831
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  /22

  $239,000

  • 1 Bed
  • 1 Bath
  • 549 Sq Ft

  59 Courtland Ave Unit 3O, Stamford, CT 06902

  An adorable one bedroom with Livingroom, full bathroom and kitchen unit in Kingswood Complex. No age restrictions for the time being. Convenient location. Beautiful, elegant and spacious community hall. Common charge includes electricity, heating, cooling, hot water and free gym to exercise.

  Li Zhang Golden Heights LLC

  59 Courtland Ave Unit 3O, Stamford, CT 06902
• 

  

  /40

  $475,000

  • 2 Beds
  • 1.5 Baths
  • 1,646 Sq Ft

  406 Courtland Ave Unit D, Stamford, CT 06906

  Stunning tri-level townhome fully-updated & move-in-ready! Amazingly spacious & bright home featuring desirable open floor plan. Main level living room, dining area and gorgeous kitchen w/ newer wood-grained vinyl floors plus an updated power room. Second floor features a large primary bedroom w/ two spacious closets, a beautifully renovated full bathroom w/ walk-in tiled shower, a second bedroom

  Christopher Sinatra Higgins Group Real Estate

  406 Courtland Ave Unit D, Stamford, CT 06906
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  /18

  $15,000,000

  • 8 Beds
  • 10.5 Baths
  • 10,171 Sq Ft

  16 Windrose Way, Greenwich, CT 06830

  Waterfront estate in coveted Mead Point, one of a few gated communities in Greenwich, ready for the next chapter. Prominently sited on 2 glorious acres with 225' of shorefront, luxurious pool and expansive open lawns. Amazing privacy with the Windrose Association 5-acre park next door, which has dock with electricity & water. Seven ensuite bedrooms; main floor primary suite. Grand reception hall

  Amanda Miller Houlihan Lawrence

  16 Windrose Way, Greenwich, CT 06830
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  /11

  $249,000

  • 1 Bed
  • 1 Bath
  • 510 Sq Ft

  8 Wardwell St Unit 6, Stamford, CT 06902

  Don't miss out on this amazing opportunity! One-bedroom condo in the heart of Stamford, with recent renovations, new appliances, and all the perks- beaches, parks, libraries, you name it, it's all within proximity. Fully gutted and updated with professional work and building permits. Act fast before it's gone!

  Kamrun Mannan US Asset Realty

  8 Wardwell St Unit 6, Stamford, CT 06902
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  /40

  $13,750,000

  • 6 Beds
  • 7 Baths
  • 9,418 Sq Ft

  52 Carriglea Dr, Riverside, CT 06878

  Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.13 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

  Stephen Archino Sotheby's International Realty

  52 Carriglea Dr, Riverside, CT 06878
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  /16

  $414,500

  • 1 Bed
  • 1 Bath
  • 885 Sq Ft

  2289 Bedford St Unit G11, Stamford, CT 06905

  Welcome to Chesterfield, one of Stamford's most sought-after gated communities! This freshly painted 1-bedroom, 1-bath unit offers the perfect blend of comfort, convenience, and style! The open-concept living and dining area with hardwood floors, is bright and inviting, featuring sliding glass doors that lead to a private deck, ideal for outdoor dining or morning coffee! The newer kitchen is

  Kevin Quick William Pitt Sotheby's Int'l

  2289 Bedford St Unit G11, Stamford, CT 06905
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  /24

  $649,900

  • 1 Bed
  • 1.5 Baths
  • 900 Sq Ft

  51 Hale Ln Unit 51, Darien, CT 06820

  Welcome to Middlesex Commons-Darien's most coveted condominium community! This stunning upper level (2nd floor) unit offers the perfect blend of luxury, comfort, & convenience. From gleaming hardwood floors to a beautifully updated kitchen & sparkling baths, every detail has been thoughtfully curated. Step out onto your private deck and take in the impeccably landscaped grounds. Inside, you'll

  Catherine Richardson William Pitt Sotheby's Int'l

  51 Hale Ln Unit 51, Darien, CT 06820
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  /38

  $749,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,676 Sq Ft

  31 High Clear Dr, Stamford, CT 06905

  Welcome to your next chapter in the heart of the Newfield neighborhood-a charming Cape Cod-style home offering both character and comfort. With 4 bedrooms and 3 full bathrooms spread over 2,676 square feet, there's plenty of space to live, relax, and enjoy. As you enter, warm hardwood floors lead you through a welcoming main level with 9 foot ceilings and a cozy wood-burning fireplace-perfect

  Jeffrey Wirz Keller Williams Prestige Prop.

  31 High Clear Dr, Stamford, CT 06905
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  /30

  $899,000

  • 3 Beds
  • 5 Baths
  • 3,301 Sq Ft

  88 Maple Tree Ave Unit G, Stamford, CT 06906

  Welcome to The Maples, an exceptional townhome community tucked away in a private wooded enclave on the Darien border. This spacious 3,300 sq.ft. residence offers 3 bedrooms, 3 full baths, and 2 half baths across four finished levels. The main floor is designed for entertaining, featuring an open-concept layout that seamlessly connects the bright white kitchen-complete with marble counters,

  Megan Pavia Berkshire Hathaway NE Prop.

  88 Maple Tree Ave Unit G, Stamford, CT 06906
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  /39

  $3,333,333

  • 8 Beds
  • 7 Baths
  • 4,359 Sq Ft

  41 Valley Rd, Cos Cob, CT 06807

  41 Valley Road, Cos Cob, CT - Impeccable Mixed-Use Opportunity Exceptional Investment in the Heart of Cos Cob Welcome to 41 Valley Road, an outstanding and meticulously maintained mixed-use property nestled in the vibrant community of Cos Cob, Connecticut. This unique offering presents a rare opportunity to own a top-quality building in one of Greenwich's most desirable and historically

  Antonio LaRocca The LaRocca Group

  41 Valley Rd, Cos Cob, CT 06807
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  /18

  $850,000

  • 3 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  25 Hoover Rd, Riverside, CT 06878

  Great opportunity to make this cute Colonial in the highly desirable Riverside section of Greenwich your own. Featuring 4 bedrooms and 1.5 baths, including a convenient first-floor bedroom, this home offers a flexible layout with plenty of space to update and customize to your style. The dining room flows into the kitchen, and a one-car garage provides added convenience. Set on public water and

  Kary Apanovitch Coldwell Banker Realty

  25 Hoover Rd, Riverside, CT 06878
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  /18

  $649,900

  • 3 Beds
  • 3.5 Baths
  • 2,391 Sq Ft

  2435 Bedford St Unit 14C, Stamford, CT 06905

  Welcome to Chesterfield, Stamford's premier gated community offering a blend of privacy, convenience, and resort-style amenities. This spacious Hampton-model townhouse is one of the largest floor plans, featuring 3 bedrooms, 3.5 baths, plus a versatile loft. The main level offers an open-concept living and dining area with hardwood floors, a fireplace, and sliders to a private deck. The updated

  Melonie Smith Epique Realty LLC

  2435 Bedford St Unit 14C, Stamford, CT 06905
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  /33

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 3,182 Sq Ft

  20 Center Dr, Old Greenwich, CT 06870

  Welcome to this beautiful 5 BR, 4.5 Bath home in the heart of Old Greenwich and the coveted Dundee International school district. Incredibly convenient to Binney Park, Perrot Library, Metro-North, and all that OG village has to offer, this transformative, to the studs renovation & expansion was designed by award winning Greenwich architect Krist Dodaro. The open-concept main floor features a

  Michelle Luksic BHHS New England Properties

  20 Center Dr, Old Greenwich, CT 06870
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  /37

  $4,475,000

  • 5 Beds
  • 5.5 Baths
  • 6,135 Sq Ft

  261 Hollow Tree Ridge Rd, Darien, CT 06820

  This charming 5-bedroom Cape Cod home, originally built in 1941 and extensively renovated, expanded and rebuilt in 2015, is the perfect blend of classic elegance and modern comfort. Nestled in a highly sought-after neighborhood, the property offers spacious living with timeless details throughout. From the moment you step inside, you're greeted by beautiful hardwood floors, crown molding, and

  Catherine Russell Brown Harris Stevens

  261 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  /23

  $425,000

  • 2 Beds
  • 1.5 Baths
  • 1,519 Sq Ft

  825 Hope St Unit 8, Stamford, CT 06907

  Starting out or downsizing? Here's a townhouse style condo with an attached one car garage in the 9 unit Hope Manor complex in the convenient Springdale neighborhood in Stamford. Plenty of space with a fireplace in the large living room, a formal dining room, an eat in kitchen, and two large bedrooms. A sizable den, good storage space and laundry are on the garage level. Primary bedroom has extra

  Richard Loh Houlihan Lawrence

  825 Hope St Unit 8, Stamford, CT 06907
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  /40

  $2,095,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  19 Anthony Ln, Darien, CT 06820

  This newly re-built 4-bedroom, 3-bath Colonial offers 2400 sq feet of finely crafted living space on a level .25-acre lot. Set on the corner of Anthony Lane and a cul-de-sac, the property pairs neighborhood charm with privacy. Enjoy the outdoors in a newly fenced yard with professional landscaping and a full irrigation system. Inside, the open layout is defined by natural light and superior

  Hillary Miller Houlihan Lawrence

  19 Anthony Ln, Darien, CT 06820
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  /29

  $2,250,000

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft

  20 Park Place, Riverside, CT 06878

  Stunning , fully renovated three-bedroom, two-and-one-half bath Home was stripped down to the studs and rebuilt with meticulous attention to detail. The open floor plan has white oak floors, a chef's kitchen, marble counters and backsplash. There are two generous bedrooms on the main level and a spa-like bath. Convenient laundry room, powder room, spacious living room/dining area and vaulted

  Susan Bisanzo Houlihan Lawrence

  20 Park Place, Riverside, CT 06878
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  /27

  $1,595,000

  • 4 Beds
  • 3 Baths
  • 2,707 Sq Ft

  8 Forest Rd, Darien, CT 06820

  Incredible value in one of Darien's most-loved neighborhoods! 4 bedrooms, 3 full bathrooms with 2,707 square feet of space. Walk to Holmes School, Middlesex Middle School, Darien High School and Noroton Heights train and shopping. Improvements include: fully fenced backyard, new gas range, new dishwasher, refinished hardwood floors and kitchen cabinets, new driveway with Belgium blocks and curb,

  Sara Hesli Houlihan Lawrence

  8 Forest Rd, Darien, CT 06820
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  /39

  $8,695,000

  • 5 Beds
  • 8 Baths
  • 6,108 Sq Ft

  25 Tokeneke Trail, Darien, CT 06820

  25 Tokeneke Trail - Where the Sky meets the Sea. Wake up to breathtaking sunrises, spend afternoons on the water, and end each day with sunset views from your private terrace. 25 Tokeneke Trail isn't just a home-it's a lifestyle. Perfectly perched above the shoreline and not in a flood zone, this stunning waterfront retreat offers direct access to the water with its own private beach, dock and

  Nellie Snell William Raveis Real Estate

  25 Tokeneke Trail, Darien, CT 06820
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  /35

  $2,595,000

  • 4 Beds
  • 2.5 Baths
  • 2,367 Sq Ft

  143 Lockwood Rd, Riverside, CT 06878

  Impeccable home in a fantastic Riverside location close to Binney Park, Perrot Library, and the Old Greenwich train station with adjacent village shopping and dining. Sidewalks lead directly to Riverside School and Eastern Middle. The main level flows between family room, dining room, and kitchen and includes a windowed den for play-space, office, or lounging. Upstairs has four bedrooms and two

  Julie Lowe Houlihan Lawrence

  143 Lockwood Rd, Riverside, CT 06878
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  /8

  $940,000

  • 6 Beds
  • 4 Baths
  • 2,464 Sq Ft

  31 Waterbury Ave, Stamford, CT 06902

  Beautifully located large two family with detached garage in heart of Stamford is on the market. You can live in one unit, rent out the other and enjoy the beautiful fall season here in Connecticut. Property will be included the next Auction. Buyers must sign up and place bids though www.xome.com. All auction properties are subject to a 5% buyer s premium pursuant to the Event Agreement and

  Davis Owen Davis Owen Real Estate

  31 Waterbury Ave, Stamford, CT 06902
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  /40

  $5,000,000

  • 6 Beds
  • 5 Baths
  • 5,021 Sq Ft

  203 Riverside Ave, Riverside, CT 06878

  Step into timeless charm with this beautifully renovated 1910 Colonial, set on 0.93 acres of level, park-like grounds in the heart of Riverside. Ideally located near the train, schools, and local shops, this residence offers both convenience and tranquility. A gracious wrap around covered porch and a stone terrace invite outdoor living, while the lush, verdant yard provides a serene backdrop for

  Patte Nusbaum Sotheby's International Realty

  203 Riverside Ave, Riverside, CT 06878
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  /9

  $249,999

  • 1 Bath
  • 508 Sq Ft

  27 Northill St Unit 3A, Stamford, CT 06907

  Located in the desirable Springdale area, this studio condo at 27 Northill Street #3A is a perfect fit for both first-time buyers and investors. Currently rented for $1,900/month, it delivers immediate rental income with strong upside potential. The building offers no rental restrictions, giving investors maximum flexibility. For first-time homeowners, this unit provides an affordable entry point

  Jhonatan Restrepo Jarah Tuttle

  27 Northill St Unit 3A, Stamford, CT 06907
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  /30

  $4,475,000

  • 4 Beds
  • 3.5 Baths
  • 3,361 Sq Ft

  21 Keofferam Rd, Old Greenwich, CT 06870

  On sought-after Keofferam Road in Old Greenwich, this property epitomizes coastal charm and timeless appeal. Just eight houses from the water and moments to both Tod's Point Beach and the village, this home presents a unique opportunity to create a legacy estate. Salty breezes, sandy mornings, and evenings in town make life here feel effortless—this is more than a home, it's a lifestyle.

  Carolyn Petersen Compass Connecticut, LLC

  21 Keofferam Rd, Old Greenwich, CT 06870
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  /26

  $4,795,000

  • 5 Beds
  • 6.5 Baths
  • 5,005 Sq Ft

  22 Carleton St, Greenwich, CT 06830

  Newly built, custom home just a short walk from Greenwich Avenue, the train, and North Street Schools. Thoughtfully designed for modern living, the residence features a beautifully designed kitchen with high end finishes, Carrara marble, Thermador appliances, retreat like bathrooms, inclusive of double vanity and soaking tub, en suite bedrooms, spacious walk in closets, four fireplaces and an

  Christopher Triano Houlihan Lawrence

  22 Carleton St, Greenwich, CT 06830
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  /7

  $540,000

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  1465 E Putnam Ave Unit 525, Old Greenwich, CT 06870

  1 br unit with deeded covered parking. Great light, loft, and common charges include heat, hot water, trash and snow. Walnut kitchen cabinets, electric blinds, and new kitchen vent. Deck and separate storage also add to the value of the unit

  Peter Hoyt William Raveis Real Estate

  1465 E Putnam Ave Unit 525, Old Greenwich, CT 06870
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  /18

  $575,000

  • 2 Beds
  • 1 Bath
  • 981 Sq Ft

  120 Webb Ave, Stamford, CT 06902

  Welcome to 120 Webb Avenue, Stamford, CT Nestled in the highly desirable Cove neighborhood, just a short stroll from Cove Island Park and Beach, this charming Cape offers the perfect balance of comfort, convenience, and coastal lifestyle. Located on a quiet street, it's an ideal home for first-time buyers, young families, or anyone looking to enjoy all that Stamford's shoreline has to offer.

  Cody Nizzardo Nizzardo Real Estate Services

  120 Webb Ave, Stamford, CT 06902
• 

  

  /39

  $2,950,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 4 Baths
  • 3,132 Sq Ft

  64 Ocean Dr E, Stamford, CT 06902

  Waterfront living at its finest. Situated directly on the Long Island Sound, this 4+ bedroom, 4-bath residence offers 75 feet of sweeping, unobstructed frontage-placing the shoreline quite literally at your doorstep. At low tide, a private sandy stretch emerges, creating a beachfront setting ideal for launching kayaks, paddle boards, or mooring a boat. Inside, light-filled interiors flow

  Ryan Dichter Compass Connecticut, LLC

  64 Ocean Dr E, Stamford, CT 06902
• 

  

  /12

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 1,891 Sq Ft

  11 Perna Ln, Riverside, CT 06878

  Lovingly built and occupied by the same family since 1954, this cherished home is filled with warmth and history. As the saying goes, ''if these walls could talk''—they would share stories of generations gathered around the table, the aroma of Sunday sauce filling the air, and countless moments spent together.Set on a generous lot with room for a pool (a pool once graced the property),

  Angela Swift Compass Connecticut, LLC

  11 Perna Ln, Riverside, CT 06878
• 

  

  /21

  $12,750,000

  • 6 Beds
  • 6.5 Baths
  • 6,918 Sq Ft

  166 Indian Head Rd, Riverside, CT 06878

  Direct waterfront located on one of Riverside's prestigious roads, this stone & shingle home designed by noted architectural firm Austin, Patterson & Disston and built by award winning premier builders Hobbs Construction. All public rooms and most private overlook the 1.6 waterfront acres. The expansive parklike backyard is bookended with a 75' lap pool and steps leading to the waters edge,

  Robin Kencel Compass Connecticut, LLC

  166 Indian Head Rd, Riverside, CT 06878

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