Old Greenwich, CT Homes for Sale with Pool

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  /39

  $1,195,000

  • 3 Beds
  • 2.5 Baths
  • 3,579 Sq Ft

  6 Nyselius Place, Stamford, CT 06905

  Step into a lifestyle of pure WOW where over 2,300 square feet of updated living space, crowned by dramatic, soaring cathedral ceilings, invites you to an open-concept masterpiece. The heart of this split-level sanctuary is the combined gourmet Kitchen, featuring quartz countertops, an oversized island, & endless storage, & the Living Room/Dining area where a stunning floor-to-ceiling fireplace

  Cynde Koritzinsky William Pitt Sotheby's Int'l

  6 Nyselius Place, Stamford, CT 06905
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  /38

  $319,000

  $20K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft

  91 Strawberry Hill Ave Unit 139, Stamford, CT 06902

  WELCOME to EASY LIVING in Most Desired Complex in the HEART of DOWNTOWN. No Hassel of elevator & steps. Beautifully Renovated, move in ready, this 1St Floor 2 bedrooms & 1 Bath apt is thoughtfully designed for everyday living. Freshley painted interior & new Flooring creates a bright & Contemporary feel. Open concept Living Room & Dining area leads to the Balcony. 2 generous size bedrooms

  Meera Banta BHGRE Shore & Country

  91 Strawberry Hill Ave Unit 139, Stamford, CT 06902
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  /29

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 2,215 Sq Ft

  20 Priscilla Ln, Port Chester, NY 10573

  Nestled in one of the most sought-after neighborhoods in town, Priscilla Lane, this spacious four-bedroomtwo bath home is set on a large beautifully sized lot offering both privacy and room to enjoy outdoor living on the covered patio and in ground pool. Designed for comfortable everyday living and entertaining alike. The home features an eat-in-kitchen perfect for casual meals, a formal

  Kathleen Zaccagnino Rye Port Real Estate, Inc.

  20 Priscilla Ln, Port Chester, NY 10573
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  /6

  $24,500,000

  • 9 Beds
  • 13 Baths
  • 16,154 Sq Ft

  16 Doubling Rd, Greenwich, CT 06830

  Bellavista is a 16,000+sf estate designed by Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus LI Sound views from the 2nd and 3rd floors,A truly sophisticated modern lifestyle.The residence is

  Jill Kelly Sotheby's International Realty

  16 Doubling Rd, Greenwich, CT 06830
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  /25

  $19,000,000

  • 5 Beds
  • 8.5 Baths
  • 8,248 Sq Ft

  207 Long Neck Point Rd, Darien, CT 06820

  This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned

  Shelly Tretter Lynch Compass Connecticut, LLC

  207 Long Neck Point Rd, Darien, CT 06820
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  /21

  $518,000

  • 1 Bed
  • 1.5 Baths
  • 1,106 Sq Ft

  1 Broad St Unit 17C, Stamford, CT 06901

  High Style luxury living at ''1 BROAD STREET''. For Sale with TENANT Renewed Lease 12-2026. Luxury Downtown High Rise with 24/7 Concierge. AMAZING Unobstructed VIEWS over the Mill River Park- Beautiful Sunsets. Great for Buyer who does can wait to move-in yet or Investor. Sophisticated, spacious 1BR 1100sqft with 1.5 Baths. Hardwood floors in ALL rooms. Open floorplan with Gourmet kitchen.

  Sharon Giglio Sharon Giglio Luxury Real Estate

  1 Broad St Unit 17C, Stamford, CT 06901
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  /23

  $10,350,000

  • 5 Beds
  • 4 Baths
  • 8,223 Sq Ft

  111 Byram Shore Rd, Greenwich, CT 06830

  Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage

  Joseph Barbieri Sotheby's International Realty

  111 Byram Shore Rd, Greenwich, CT 06830
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  /16

  $28,500,000

  New Construction

  • 7 Beds
  • 12 Baths
  • 18,370 Sq Ft

  39 Brookridge Dr, Greenwich, CT 06830

  Set along a quiet street 3 mins from town, this exceptional 2027 new construction blends timeless architecture w modern livability. A striking white brick façade, steep gables, and dark-framed windows create a refined yet welcoming presence. Warm interior light highlights expansive living spaces, including a dramatic kitchen and family room designed for both everyday living and elevated

  Amanda Bates Houlihan Lawrence

  39 Brookridge Dr, Greenwich, CT 06830
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  /39

  $42,995,000

  • 6 Beds
  • 9 Baths
  • 12,492 Sq Ft

  545 Indian Field Rd, Greenwich, CT 06830

  A rare waterfront estate of true scale and presence, this reimagined coastal masterpiece commands 1.6 acres on the Long Island Sound with sweeping, unobstructed horizon views. Rebuilt from the foundation up, the home delivers level beachfront living with powerful architectural lines, floor-to-ceiling glass, and a seamless connection to the water at every turn. The approach opens to a 19-foot

  Jesse Marinak Serhant Connecticut LLC

  545 Indian Field Rd, Greenwich, CT 06830
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  /40

  $14,995,000

  • 11 Beds
  • 17 Baths
  • 15,479 Sq Ft

  326 Stanwich Rd, Greenwich, CT 06830

  Welcome to An Extraordinary Lakeside Retreat in GreenwichEncompassing an incredible assemblage of 9.4 lakeside acres ideally situated within the Greenwich mid country, Frye Lake Compound is the ultimate sanctuary for those seeking a world of elevated privacy, scenery and architecture. Nestled around the serene 11-acre Frye Lake, this incomparable park-like estate represents an idyllic

  Kevin Sneddon Compass Connecticut, LLC

  326 Stanwich Rd, Greenwich, CT 06830
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  /40

  $2,950,000

  • 6 Beds
  • 3.5 Baths
  • 5,105 Sq Ft

  40 Rogers Rd, Stamford, CT 06902

  Tucked within Stamford's coveted Shippan Point, 40 Rogers Road presents a refined coastal offering just moments from the water. Thoughtfully reimagined, the residence blends timeless character with a comprehensive suite of recent upgrades, delivering a turnkey living experience. Sun-filled interiors offer well-proportioned spaces with seamless flow for everyday living and entertaining. The second

  Ryan Dichter Compass Connecticut, LLC

  40 Rogers Rd, Stamford, CT 06902
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  /32

  $850,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  77 Havemeyer Ln Unit 324, Stamford, CT 06902

  Palmer Hill luxury 2 bedroom, 2 baths, condo located on the Old Greenwich/Stamford border. The vaulted ceilings, updated kitchen, wide-plank hardwood floors throughout, updated primary bath and enlarged entry hall, make this an exceptional unit located on the top (3rd) floor. This light filled unit with two story windows in the living room and both bedrooms features a lovely south facing balcony

  Emile de Neree Compass Connecticut, LLC

  77 Havemeyer Ln Unit 324, Stamford, CT 06902
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  /32

  $430,000

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  154 Cold Spring Rd Unit 5, Stamford, CT 06905

  Welcome to Candlelight Terrace, where comfort meets convenience. This beautifully maintained condo offers a bright, open layout with spacious living areas and abundant natural light. Enjoy the ease of living with heat, hot water, and water included in the common charges, adding exceptional value and peace of mind. Set in a well-kept community with ample parking, all just minutes from shopping,

  Claribel Bueno eXp Realty

  154 Cold Spring Rd Unit 5, Stamford, CT 06905
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  /25

  $15,000,000

  Coming Soon

  • 6 Beds
  • 11 Baths
  • 10,523 Sq Ft

  4 Rockwood Lane Spur, Greenwich, CT 06830

  Modern planning, superior craftsmanship and bespoke details define this extraordinary newly built Transitional home by visionary leaders Christopher Pagliaro Architects, East Coast Structures and M&N Development. Private 1.64 acres showcase resort style amenities indoors and out. Brick and cast stone facade home offers 10,573 sq. ft. on four customized levels with oversized European Klar windows,

  Deborah Needle Houlihan Lawrence

  4 Rockwood Lane Spur, Greenwich, CT 06830
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  /28

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  89 Harbor Dr Unit 206, Stamford, CT 06902

  Three-level, 3-bedroom, 2.5-bathroom townhouse at Schooner Cove in Stamford, Connecticut - with a deeded garage, deeded 32-foot boat slip, and partial water views from two private balconies.This townhouse at Schooner Cove delivers a rare marina lifestyle with low-maintenance living in one of Stamford's most sought-after waterfront communities. The open-concept main level combines kitchen, dining,

  Hannah Driscoll Berkshire Hathaway NE Prop.

  89 Harbor Dr Unit 206, Stamford, CT 06902
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  /6

  $3,495,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 3,517 Sq Ft

  97 Riverside Ave, Riverside, CT 06878

  Rare opportunity in Riverside. Set on .42 acres of beautifully landscaped grounds with an in-ground pool, this exceptional 3,500 SF home offers timeless elegance, expansive living space, and incredible potential. Featuring 3 bedrooms and 2.1 baths, the home can be expanded to approximately 5,700 SF, plus an additional 1,200+ SF lower level ready to be finished.Designed for both everyday

  Jennifer Danzi-glenn Jennifer M Danzi, Broker

  97 Riverside Ave, Riverside, CT 06878
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  /38

  $12,100,000

  • 6 Beds
  • 13 Baths
  • 11,668 Sq Ft

  524 Lake Ave, Greenwich, CT 06830

  A gated drive opens to this elegant six-bedroom Mid-Country Manor overlooking tranquil views of Horseneck Brook. A stone courtyard introduces the dramatic four-story residence with elegant foyer, where sweeping butterfly staircases and limestone floors create a striking architectural welcome. From the gracious gallery hall, beautifully proportioned formal and informal rooms unfold-including

  Leslie McElwreath Sotheby's International Realty

  524 Lake Ave, Greenwich, CT 06830
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  /32

  $490,000

  Open Thu 4PM - 6PM

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

  2289 Bedford St Unit A9, Stamford, CT 06905

  Sun-drenched two-Story condo in the coveted Chesterfield Complex - 2289 Bedford Street. Discover refined condo living in one of the area's most sought-after communities. This stunning 1-bedroom, 2-bath residence spans two beautifully designed floors, flooded with natural light from every angle to create a warm, airy atmosphere throughout. Inside, you'll find a tastefully updated kitchen and

  Jacqueline Rabinowitz Houlihan Lawrence

  2289 Bedford St Unit A9, Stamford, CT 06905
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  /12

  $340,000

  • 1 Bed
  • 1 Bath
  • 879 Sq Ft

  85 Riverside Ave Unit C5, Stamford, CT 06905

  This sun-drenched, ranch style condo features a sparkling, resort style pool with river views just steps from your door. Other features include oversized rooms with sliders to deck, ample closets, reserved parking, low HOA and additional storage. Updated appliances, new Tub surround, freshly painted and professionally cleaned. Bring your design expertise to make this condo your forever home.

  Jo-Ann Fiore Coldwell Banker Realty

  85 Riverside Ave Unit C5, Stamford, CT 06905
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  /15

  $299,000

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft

  71 Strawberry Hill Ave Unit 119, Stamford, CT 06902

  Welcome to this bright and comfortable first floor 2BR condo at Fountain Terrace, offering effortless living in a prime Stamford location. The open layout provides great flow, with large windows that bring in natural light throughout the day. Residents enjoy a well-maintained community featuring 24hour security, a seasonal outdoor pool, secure entry, laundry facilities, and onsite management. The

  Richard Wilson Coldwell Banker Realty

  71 Strawberry Hill Ave Unit 119, Stamford, CT 06902
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  $2,350,000

  • 5 Beds
  • 2.5 Baths
  • 3,340 Sq Ft

  12 Old Post Rd, Cos Cob, CT 06807

  A special opportunity to own this charming oasis close to town. Tucked behind iron gates awaits an enclave with pool, mature trees and ivy. The main floor has a spacious living room that leads to a heated sunroom, a formal dining room and a kitchen with a commercial cooktop and vent system. The second floor has a primary bedroom with a marble bath and shower and en-suite sitting room/closet. 2

  Mie Glenn BHHS New England Properties

  12 Old Post Rd, Cos Cob, CT 06807
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  /10

  $14,750,000

  New Construction $900K PRICE INCREASE

  • 7 Beds
  • 9 Baths
  • 10,496 Sq Ft

  133 Doubling Rd, Greenwich, CT 06830

  Stunning 6-bedroom Colonial in Mid-Country currently underway (Summer '26 completion). Designed to impress by the renowned Alex Kaali-Nagy Architect AIA with a traditional exterior look, quintessential Greenwich, but a transitional interior with 4 finished levels and thoughtful design touches throughout, including extensive millwork. Exceptional primary suite with walk-in dressing rooms, plus 5

  Amanda Miller Houlihan Lawrence

  133 Doubling Rd, Greenwich, CT 06830
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  /49

  $100,000,000

  • 8 Beds
  • 14 Baths
  • 13,163 Sq Ft

  108 Cedar Cliff Rd, Riverside, CT 06878

  Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of

  Leslie McElwreath Sotheby's International Realty

  108 Cedar Cliff Rd, Riverside, CT 06878
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  $660,000

  • 2 Beds
  • 3.5 Baths
  • 2,211 Sq Ft

  2435 Bedford St Unit 14D, Stamford, CT 06905

  Welcome to Chesterfield, one of Stamford's most prestigious condominium complexes. This lovely townhome exhibits pride of ownership throughout: freshly painted and new carpeting as well as a refreshed kitchen with stainless appliances (microwave and dishwasher are brand new) and new quartz countertops. The main level boasts hardwood floors with an open concept living and dining room, wood burning

  Mary Russo Keller Williams Prestige Prop.

  2435 Bedford St Unit 14D, Stamford, CT 06905
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  /7

  $10,350,000

  $500K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 7,072 Sq Ft

  12 Woodside Rd, Greenwich, CT 06830

  DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive,

  Leslie McElwreath Sotheby's International Realty

  12 Woodside Rd, Greenwich, CT 06830
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  /39

  $13,100,000

  • 6 Beds
  • 8 Baths
  • 10,286 Sq Ft

  7 Parsonage Rd, Greenwich, CT 06830

  SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously

  Leslie McElwreath Sotheby's International Realty

  7 Parsonage Rd, Greenwich, CT 06830
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  /20

  $899,000

  • 4 Beds
  • 2 Baths
  • 1,737 Sq Ft

  73 High Clear Dr, Stamford, CT 06905

  Charming and beautifully maintained 1956 Cape Cod offering timeless character with thoughtful updates throughout. This inviting 4-bedroom, 2-bath home features an updated kitchen, warm and comfortable living that creates exceptional curb appeal. Enjoy outdoor entertaining or quiet relaxation on the private patio surrounded by established landscaping. A perfect blend of classic charm and modern

  James Capparelle Coldwell Banker Realty

  73 High Clear Dr, Stamford, CT 06905

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