Old Greenwich, CT Houses for Sale

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  /40

  $1,800,000

  • 6 Beds
  • 5 Baths
  • 3,461 Sq Ft

  47 Hollow Tree Ridge Rd, Darien, CT 06820

  A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or young couples seeking rental income. Historic Charm, Modern Comfort: * Two

  

  Karen Finn

  Gatehouse Realty Inc

  (475) 325-5924

  47 Hollow Tree Ridge Rd, Darien, CT 06820
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  /36

  $5,495,000

  • 6 Beds
  • 8 Baths
  • 7,930 Sq Ft

  20 Sherwood Farm Ln, Greenwich, CT 06831

  Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! A stunning custom built white Georgian Colonial in the coveted mid country Sherwood Farm Association is sited on a picturesque level acre lot. This six bedroom

  

  Richard Higgins

  Higgins Group Bedford Square

  (203) 433-0559

  20 Sherwood Farm Ln, Greenwich, CT 06831
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  /20

  $609,000

  • 4 Beds
  • 1 Bath
  • 1,238 Sq Ft

  42 Sylvan Knoll Rd, Stamford, CT 06902

  This charming Cape in the Cove offers convenient access to the beach, and a large inviting back yard provides potential for expansion. Outdoor living space includes a covered patio that overlooks a beautifully landscaped private yard, which is ideal for entertaining or relaxing. Inside, there are four bedrooms, a living room with fireplace, a kitchen appointed with bamboo flooring, a dining room,

  

  Glenn Marr

  Marr Caruso Realty Group

  (203) 433-6729

  42 Sylvan Knoll Rd, Stamford, CT 06902
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  /29

  $9,950,000

  • 6 Beds
  • 8 Baths
  • 8,896 Sq Ft

  35 Club Rd, Riverside, CT 06878

  Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors,

  

  Andrew Smith

  Houlihan Lawrence

  (475) 265-6383

  35 Club Rd, Riverside, CT 06878
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  /34

  $853,000

  • 3 Beds
  • 3.5 Baths
  • 4,433 Sq Ft

  53 W Hill Cir, Stamford, CT 06902

  ** Highest and Best by Monday, July 28, 2025 at 12:00 PM (Noon) ** Lovingly owned by one family for 63 years, this expansive custom-built Westover ranch offers incredible space, versatility, and untapped potential! With over 3,000 SF on the main level and an additional ~1,423 SF in the walk-out lower level, this home is ideal for multigenerational living, entertaining, or future in-law/guest

  Linda Lang-Bankowski The Real Estate Boutique, LLC

  53 W Hill Cir, Stamford, CT 06902
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  /37

  $8,490,000

  • 5 Beds
  • 7 Baths
  • 4,448 Sq Ft

  10 W Crossway, Old Greenwich, CT 06870

  Welcome to your dream vacation-like setting! This bright and spacious 5 bed 7 bath property boasts a tranquil ambiance with stunning sunsets that will take your breath away. Perfect for cozy evenings looking at the water. Multiple options for offices including bonus space above the garage are the perfect Zoom refuge. Entertain and relax on the inviting patios while taking in the breathtaking

  Christian Perry Sotheby's International Realty

  10 W Crossway, Old Greenwich, CT 06870
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  /43

  $3,895,000

  • 6 Beds
  • 5.5 Baths
  • 5,175 Sq Ft

  119 Hendrie Ave, Riverside, CT 06878

  This spacious Riverside Colonial is located on one of the less traveled streets extending from Riverside School to Binney Park. Artfully expanded & renovated from its original 40's design, the main rooms feature high ceilings, wide windows and generous scale. The dramatic three-story entrance hall is flanked by a formal living room & large family room , both w handsome fireplaces, & it extends

  Heather Platt Sotheby's International Realty

  119 Hendrie Ave, Riverside, CT 06878
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  /28

  $3,895,000

  • 5 Beds
  • 3.5 Baths
  • 3,647 Sq Ft

  258 Riverside Ave, Riverside, CT 06878

  Tucked away down a private driveway off Riverside Avenue, this stylishly updated, cedar-clad home offers the perfect blend of classic charm and modern farmhouse appeal. Set on over a half an acre of level lawn, this peaceful retreat is just minutes from the train, town and coastline. The sun-filled living room, framed by twin picture windows, sets a warm and welcoming tone. At the center

  Tracey Koorbusch Sotheby's International Realty

  258 Riverside Ave, Riverside, CT 06878
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  /7

  $8,750,000

  • 6 Beds
  • 7.5 Baths
  • 10,400 Sq Ft

  11 Winterset Rd, Greenwich, CT 06830

  Mid Country New Construction smart home on 2.16 exquisite level acres will be completed by early fall, 2025. 10K+ SF of finished space on 4 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th en-suite bedroom on 3rd floor. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular indoor / outdoor living is designed

  Amanda Bates Houlihan Lawrence Inc.

  11 Winterset Rd, Greenwich, CT 06830
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  /31

  $3,450,000

  • 4 Beds
  • 3.5 Baths
  • 3,187 Sq Ft

  87 Orchard Dr, Greenwich, CT 06830

  Chic California-style residence in the coveted Milbrook Association, set on .88 acre with sweeping lake views and 200 ft of waterfront. Tucked at the end of a peaceful road, this light-filled home features floor-to-ceiling windows, skylight, original English brick fireplace, and an open layout perfect for entertaining. Gourmet kitchen with Sub-Zero and Wolf appliances, vaulted family room,

  Krissy Blake Sotheby's International Realty

  87 Orchard Dr, Greenwich, CT 06830
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  /40

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 5,025 Sq Ft

  22 Gardiner St, Darien, CT 06820

  Welcome to 22 Gardiner Street - a 2015 custom built colonial. Walk through the front door and be greeted by a bright and spacious open floor plan including a living room and dinning room, eat-in kitchen and family room - all boasting 9 ft. ceilings, custom millwork and beautiful hardwood floors. The gourmet kitchen includes custom cabinetry, top-of-the-line appliances, a generous center island

  Kimberly Hyde William Pitt Sotheby's Int'l

  22 Gardiner St, Darien, CT 06820
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  /35

  $3,500,000

  • 3 Beds
  • 2 Baths
  • 2,859 Sq Ft

  40 Bruce Park Dr, Greenwich, CT 06830

  Nestled on a scenic knoll in the heart of Greenwich, just moments from downtown & directly across from the picturesque Bruce Park, this fully renovated home offers the perfect blend of timeless mid-century design & modern luxury. Boasting an open-concept layout, the sun-drenched interior features three spacious bedrooms & two elegant bathrooms. The gourmet kitchen flows effortlessly into the

  Danielle Claroni Sotheby's International Realty

  40 Bruce Park Dr, Greenwich, CT 06830
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  /35

  $3,275,000

  • 5 Beds
  • 2.5 Baths
  • 3,670 Sq Ft

  14 Highview Ave, Old Greenwich, CT 06870

  RARE OPPORTUNITY AND ENDLESS POSSIBILITIES ON OVERSIZED LOT IN THE HEART OF OLD GREENWICH! Charming, lived in and loved, this 1918 Colonial sits on one of OG's most desirable streets in The Village. The 3,670sf home blends timeless architecture with a welcoming layout and high ceilings. Additional FAR available for expansion. A wide wraparound front porch opens to well-proportioned entry hall,

  Christine McKelvey Corcoran Centric Realty LLC

  14 Highview Ave, Old Greenwich, CT 06870
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  /49

  $3,450,000

  • 4 Beds
  • 6 Baths
  • 4,382 Sq Ft

  15 Deepwoods Ln, Old Greenwich, CT 06870

  This beautifully designed home offers grand living space with modern luxury. 4 Spacious Bedrooms + den/study, gorgeous Living room, formal dining room, gourmet kitchen with 2 refrigerators, family room overlooking backyard and conservation land. Large basement is equipped with wet bar/island and great for entertainment.Quiet tree lined street yet convenient to all. Binney park, Library,

  Miyoko Matsuo Relo Redac, Inc

  15 Deepwoods Ln, Old Greenwich, CT 06870
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  /53

  $4,995,000

  • 4 Beds
  • 6 Baths
  • 5,244 Sq Ft

  34 Edgewood Dr, Greenwich, CT 06831

  Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, masterfully renovated in 2025 this Colonial offers a harmonious blend of heritage architecture and sophisticated modernity. Designed to accommodate both grand-scale entertaining and intimate daily living, the residence unfolds across three levels and over 7,000 square feet of meticulously curated

  Danielle Scialpi-Malloy Serhant Connecticut LLC

  34 Edgewood Dr, Greenwich, CT 06831
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  /27

  $2,925,000

  • 5 Beds
  • 4.5 Baths
  • 4,108 Sq Ft

  32 Meyer Place, Riverside, CT 06878

  This attractive and spacious 5-bedroom Colonial on peaceful cul-de-sac in Riverside was rebuilt and expanded in 2006 with a modern floor plan. The interior extends to 4,100 sq ft. with recent upgrades and extra ceiling height in many of the rooms providing generous scale and abundant natural light. The large kitchen with breakfast area flows to the expansive family room with fireplace. French

  Christopher Finlay Brown Harris Stevens CT, LLC

  32 Meyer Place, Riverside, CT 06878
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  /19

  $3,495,000

  • 6 Beds
  • 4.5 Baths
  • 3,515 Sq Ft

  22 Tomac Ave, Old Greenwich, CT 06870

  Terrific Old Greenwich location with easy access to south of the village with sidewalks to town, school and train. This gracious Shore Colonial is on an over-sized o.46 acre level lot (FAR in the R-12 zone could allow 6,300+ sf home), is warm and welcoming with 5 bedrooms and 3 full baths PLUS an additional studio on the main level that could be used in so many ways, as a main floor bedroom,

  Jackie Hammock Coldwell Banker Realty

  22 Tomac Ave, Old Greenwich, CT 06870
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  /39

  $2,799,999

  • 6 Beds
  • 9 Baths
  • 6,191 Sq Ft

  72 Little Hill Dr, Stamford, CT 06905

  72 Little Hill Drive - Stately Colonial in the Heart of Newfield Privately nestled in one of Newfield's most sought-after neighborhoods, this grand colonial offers over 6,300 sq ft of beautifully finished living space, including 6 bedrooms, 5 full and 4 half baths, and a 4-car garage. Built in 1865 and fully renovated, the home blends timeless charm with modern luxury. The expansive backyard is

  Anthony Gaglio Jr Hathaway, Inc.

  72 Little Hill Dr, Stamford, CT 06905
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  /32

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,476 Sq Ft

  52 Morningside Dr, Greenwich, CT 06830

  This stunning 5-bedroom, 4-bathroom home, built in 2023, offers contemporary living w/high ceilings & grand two-story entrance. The kitchen opens to a cozy family room w/fireplace & French doors. First level includes a living room, dining room w/Butler's pantry, bedroom, full bath & mudroom. The second level boasts a primary suite w/spa-like bathroom, three additional bedrooms, two full

  Kelly Feda Coldwell Banker Realty

  52 Morningside Dr, Greenwich, CT 06830
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  /69

  $2,730,000

  • 4 Beds
  • 4.5 Baths
  • 3,826 Sq Ft

  681 River Rd, Cos Cob, CT 06807

  Timeless , this architecturally designed contemporary home blends soaring vaulted ceilings with panoramic views, creating a seamless connection to the outdoors. Thoughtfully sited on 2.32 peaceful, private acres, the home embraces natural light as the seasons change, all while remaining minutes from every convenience possible.The open-concept floor plan is ideal for both grand entertaining

  Paula Waldman BHHS New England Properties

  681 River Rd, Cos Cob, CT 06807
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  /19

  $2,799,000

  • 5 Beds
  • 5.5 Baths
  • 4,525 Sq Ft

  32 Jeffrey Rd, Greenwich, CT 06830

  A hidden gem close to town, updated and at the end of a cul-de-sac on a great quiet street, this beautiful 4,525-square-ft home on 1 acre offers a perfect blend of tranquility and convenience, located just minutes from town, the property boasts offices, 5 bedrooms, 5.5 baths, creating flexible layout, a perfect lifestyle for today's owner. Perfect for working from home or pursuing your passions.

  Lin Lavery Coldwell Banker Realty

  32 Jeffrey Rd, Greenwich, CT 06830
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  /29

  $2,499,000

  • 5 Beds
  • 5 Baths
  • 3,598 Sq Ft

  201 Shore Rd, Greenwich, CT 06830

  1st house on Belle Haven peninsula offers bucolic commuter convenience in a most sought-after enclave overlooking Greenwich Harbor. Positioned atop slope with outstanding Harbor views, this 5 bed, 3 full & two half bathroom residence spans 3,598 sqft. Cleverly renovated to maximize water views with upgraded systems & interior improvements, this home marries smart functional privacy with today's

  Meg McAuley Kaicher Coldwell Banker Realty

  201 Shore Rd, Greenwich, CT 06830
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  /40

  $1,399,000

  • 3 Beds
  • 3 Baths
  • 2,175 Sq Ft

  88 Indian Field Rd, Greenwich, CT 06830

  Welcome to 88 Indian Field Road, where convenience meets comfort in this updated 3 bed, 3 bath cape. Seconds from the Cos Cob Train station, Greenwich schools, parks, and dozens of dining & shopping options, this home offers unparalleled accessibility. Highlights of the surprisingly spacious layout include the living room's w/b fireplace, renovated kitchen and inviting family room perfect for

  PJ Collins Keller Williams Realty Group

  88 Indian Field Rd, Greenwich, CT 06830
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  /40

  $2,149,500

  • 4 Beds
  • 3.5 Baths
  • 2,531 Sq Ft

  47 Grey Rock Dr, Greenwich, CT 06831

  Be the first to enjoy this thoughtfully renovated 4-bedroom home in the heart of historic Glenville which has been completely remodeled and expanded in 2025 with a low maintenance lifestyle in mind. The home is flooded with natural light and features an open floor plan with the option of a first-floor primary bedroom. The kitchen and dining area includes a large island, stainless steel appliances

  Marje Vance Allocco Sotheby's International Realty

  47 Grey Rock Dr, Greenwich, CT 06831
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  /12

  $794,000

  • 3 Beds
  • 2.5 Baths
  • 1,830 Sq Ft

  99 Woodbury Ave, Stamford, CT 06907

  Opportunity awaits in this expanded Cape-style home located in the heart of sought-after Springdale! Set on a spacious and private 0.35-acre lot, this charming property features a fenced-in yard and an attached garage-offering both space and potential. Inside, you'll find 1,830 square feet of living space with 8 rooms, including 3 bedrooms and 2.5 bathrooms. Built in 1940, the home offers

  Jolanta Rojek eXp Realty

  99 Woodbury Ave, Stamford, CT 06907
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  /33

  $779,000

  • 3 Beds
  • 1.5 Baths
  • 1,744 Sq Ft

  108 4th St, Stamford, CT 06905

  A rare find in this oh so convenient walk to town location where sidewalks line the streets. Vintage 1929 Tudor style home with detached two car garage has been impeccably maintained both in and out. This timeless beauty has its original interior doors with glass knobs and boasts three bedrooms and one and a half baths. Oversized living room with fireplace extends into a window walled sunroom,

  Barbara Hickey William Pitt Sotheby's Int'l

  108 4th St, Stamford, CT 06905
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  /40

  $1,199,000 Open Thu 4:30PM - 6:30PM

  • 4 Beds
  • 3.5 Baths
  • 2,802 Sq Ft

  220 Halliwell Dr, Stamford, CT 06902

  Stunning updated Colonial! Life doesn't get sweeter than this beautiful 4-bedroom, 3.5-bath Center Hall Colonial nestled in the desirable Hycliff community. Thoughtfully updated with all the bells and whistles, this home perfect blends classic charm & modern comfort! Step inside to an inviting open floor plan that connects the kitchen & dining areas-ideal for entertaining! The sleek, updated

  Fiona Porter Keller Williams Realty

  220 Halliwell Dr, Stamford, CT 06902
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  /32

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 2,347 Sq Ft

  263 Byram Rd, Greenwich, CT 06830

  A welcoming front porch invites you to this bright and sunny four bedroom, two and a half bath Center Hall Colonial. The inviting entryway leads to a bright and airy main level, where you can enjoy family gatherings. There is 2347 square feet of living space with plenty of storage in the partially finished basement and garage. Conveniently located, this home is just minutes away from Byram

  Diana Whyte BHHS New England Properties

  263 Byram Rd, Greenwich, CT 06830
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  /40

  $950,000

  • 5 Beds
  • 3 Baths
  • 4,219 Sq Ft

  1014 Cove Rd, Stamford, CT 06902

  Welcome to the Cove, where coastal living is affordable! This stunning water community home has just been freshly painted and features designer lighting that sparkles with charm. Experience the enchantment of this meticulously staged coastal residence, perfectly maintained and brimming with love, just waiting for the next family to cherish it. Imagine being just a short stroll away from the

  Mar Jennings Higgins Group Bedford Square

  1014 Cove Rd, Stamford, CT 06902
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  /40

  $585,000

  • 2 Beds
  • 1.5 Baths
  • 1,062 Sq Ft

  57 Palmer St, Stamford, CT 06907

  Springdale home owned and cared for by the same family since 1941 offers easy living and convenience to new owners who are ready to simply refresh or tap the tremendous potential to make it their own. Originally configured as a 3-bedroom home, a wall can be added back to the large primary bedroom to restore the space. Finishing the already enclosed front and back porches as well as the bright

  Randi Skrelja William Pitt Sotheby's Int'l

  57 Palmer St, Stamford, CT 06907
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  /29

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft

  33 Halsey Dr, Old Greenwich, CT 06870

  This charming Old Greenwich home in the highly sought-after North Mianus/ Eastern school district is the perfect starter or the best condo alternative. A picturesque setting, this single-family dwelling comes with low property taxes, low maintenance responsibilities and costs. The first floor offers comfortable living and family room spaces, a newer kitchen with quartz countertop and stainless

  Anthony Ardino William Raveis Real Estate

  33 Halsey Dr, Old Greenwich, CT 06870
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  /15

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 2,073 Sq Ft

  15 Ridge Rd, Cos Cob, CT 06807

  Elegant Cape-Style Home in the Heart of Cos Cob Nestled in the desirable heart of Cos Cob, this beautifully maintained Cape offers timeless charm and spacious comfort. Featuring four well-appointed bedrooms and two full baths, the home boasts a gracious living and dining area, a sunlit eat-in kitchen that flows seamlessly into a cozy family room, and abundant storage-including a cedar-lined

  Ryan Ciambriello Houlihan Lawrence

  15 Ridge Rd, Cos Cob, CT 06807
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  /21

  $1,675,000

  • 3 Beds
  • 3.5 Baths
  • 3,104 Sq Ft

  150 Pemberwick Rd, Greenwich, CT 06831

  This modern residence offers an open floor plan with oversized windows and doors framing stunning views of the Byram River. Set high above the water, it combines privacy with scenic beauty. Beautiful and spacious fenced play yard.Features include three ensuite bedrooms with marble baths and custom walk-in closets, a sleek white kitchen with stainless steel appliances and marble finishes, a

  Amanda Miller Houlihan Lawrence

  150 Pemberwick Rd, Greenwich, CT 06831
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  /25

  $1,250,000

  • 3 Beds
  • 1.5 Baths
  • 1,333 Sq Ft

  5 Hunter St, Old Greenwich, CT 06870

  Great opportunity to own this well maintained 3 bedroom 1 1⁄2 bath colonial located at the end of a cul-de-sac in Old Greenwich. Home has an eat-in kitchen, formal dining room, living room with fireplace, spacious three season sunroom off the kitchen, deck, covered front porch, a 1 car garage, and a large .38 of an acre parcel of land.

  Calvin Darula William Raveis Real Estate

  5 Hunter St, Old Greenwich, CT 06870
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  /16

  $810,000

  • 2 Beds
  • 1.5 Baths
  • 1,463 Sq Ft

  115 Top Gallant Rd Unit 6, Stamford, CT 06902

  Welcome to 115 Top Gallant Road, Unit 6 - a beautifully maintained and thoughtfully updated townhome nestled adjacent to Stamford's Dolphin Cove and Southfield Point, with easy access to downtown and nearby Old Greenwich. This light-filled 2-bedroom, 1.5-bath home offers the perfect blend of charm, comfort, and convenience. Step inside to find soaring ceilings, a cozy gas fireplace, and an open

  Katharine Gray Bunoski Compass Connecticut, LLC

  115 Top Gallant Rd Unit 6, Stamford, CT 06902
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  /33

  $1,595,000

  • 4 Beds
  • 2.5 Baths
  • 2,884 Sq Ft

  24 Noroton Ave, Darien, CT 06820

  Just beyond a lovely fieldstone wall is 24 Noroton Avenue - a charming traditional Connecticut colonial in the heart of Darien, close to both Darien beaches, Baker Park, Blue Ribbon Hindley Elementary School and Roost Coffee just to name a few. The new Darien Commons, Heights Crossing along with the Noroton Train Station are also a short distance away with sidewalk access. The first floor

  Robyn DeCastro Brown Harris Stevens

  24 Noroton Ave, Darien, CT 06820
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  /35

  $1,600,000

  • 4 Beds
  • 3.5 Baths
  • 3,472 Sq Ft

  347 West Ave, Darien, CT 06820

  This stunning colonial in Darien, CT offers 3,472 sq ft of elegant living space with four bedrooms, including a luxurious primary suite with a full bath, a private ensuite bedroom, and two additional bedrooms share a Jack and Jill bath. Features include beautiful, oak hardwood floors, a finished lower level, a spacious deck, and a lush landscape maintained by a smart irrigation system. The home

  Keith Evans William Raveis Real Estate

  347 West Ave, Darien, CT 06820
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  /40

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,641 Sq Ft

  15 Albin Rd, Stamford, CT 06902

  Welcome to the vibrant 15 Albin Road, a sunlit Cape Cod charmer in Stamford's coveted Cove! Designer owned, This colorful coastal escape offers an open-concept flowing seamlessly from family room to kitchen to living room with fireplace, ideal for entertaining. The first floor spacious primary suite features an expansive walk-in closet and a spa-like bath with fresh, modern touches. Upstairs

  Kim Tromba Keller Williams Realty

  15 Albin Rd, Stamford, CT 06902
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  /31

  $769,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  20 Wild Horse Rd, Stamford, CT 06905

  Tucked away in the charming and welcoming area of Turn of River this lovingly maintained colonial home feels warm and charming. Inside this 3 bedroom, 2 bath home you'll find a home that's been cared for with 1890 square feet of comfortable living space on a beautifully kept lot offering a peaceful retreat that's perfect for anyone looking to settle into a cozy, private setting. The cute

  Teresa K Real Estate By Teresa LLC

  20 Wild Horse Rd, Stamford, CT 06905
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  /27

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 2,862 Sq Ft

  285 Westover Rd, Stamford, CT 06902

  Location! Welcome to an exquisite sanctuary nestled in the coveted Westover area. This stunning residence promises an elegant lifestyle with its modern touches and serene surroundings. Boasting 4 bedrooms/3.5 bathrooms this property offers a harmonious blend of sophistication and comfort. Upon entering, you'll be captivated by the chef's dream kitchen, featuring high-end appliances including a

  Noelle Iannotta Compass Connecticut, LLC

  285 Westover Rd, Stamford, CT 06902

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