Old Greenwich, CT Homes for Sale with Pool

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  /32

  $255,000

  $4K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  91 Strawberry Hill Ave Unit 425, Stamford, CT 06902

  LOCATION, LOCATION, LOCATION! Welcome to this beautifully updated, move-in-ready end-unit condominium in the highly desirable Fountain Terrace community. This bright and spacious 1-bedroom, 1-bath home features an open-concept floor plan, brand-new carpeting, abundant natural light, and a generously sized bedroom with exceptional closet space. The sun-filled living room opens to a private corner

  Irene Sorial BHGRE Shore & Country

  91 Strawberry Hill Ave Unit 425, Stamford, CT 06902
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  /21

  $16,995,000

  $2M PRICE DROP

  • 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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  /35

  $378,000

  • 2 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  50 Glenbrook Rd Unit 3D, Stamford, CT 06902

  Spacious two-bedroom, two-and-a-half-bath residence in the heart of downtown Stamford, offered at a price that reflects its potential. The open floor plan is generously proportioned and highly versatile, with ample room to relax, entertain, and work from home, while the solid layout and scale of the rooms present a rare opportunity to add real value through new flooring and a kitchen tailored

  Todd Maloof William Pitt Sotheby's Int'l

  50 Glenbrook Rd Unit 3D, Stamford, CT 06902
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  /21

  $530,000

  $12K PRICE INCREASE

  • 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''. Luxury Downtown High Rise with 24/7 Concierge. AMAZING Unobstructed VIEWS over the Mill River Park- Beautiful Sunsets. Great For Investor. Sophisticated, spacious 1BR 1100sqft with 1.5 Baths. Hardwood floors in ALL rooms. Open floorplan with Gourmet kitchen. Primary Suite with Extra-large Bedroom and EXTRA -large Walk-In-Closet! Luxurious bath with

  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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  /25

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  51 Forest Ave Unit 59, Old Greenwich, CT 06870

  Welcome to easy, one level living in the heart of Old Greenwich! This beautifully maintained 2 bedroom, 2 bath condominium at The Gables offers a bright, open layout designed for comfortable everyday living. Enjoy the convenience of one car garage parking and an unbeatable location just moments from shops, restaurants, parks, Metro-North, and Tod's Point. Residents of The Gables enjoy exceptional

  Jenny Allen Compass Connecticut, LLC

  51 Forest Ave Unit 59, Old Greenwich, CT 06870
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  /24

  $249,000

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  91 Strawberry Hill Ave Unit 235, Stamford, CT 06902

  Don't miss this turnkey 1-bedroom condo in a well-maintained gated community. The thoughtfully designed interior features durable laminate flooring throughout, an updated bathroom, and a private balcony that adds valuable outdoor living space. Enjoy resort-style amenities including a pool, gym, and security. Ideally situated near downtown, you'll have easy access to shopping, restaurants, parks,

  Priti Kothari William Raveis Real Estate

  91 Strawberry Hill Ave Unit 235, Stamford, CT 06902
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  /9

  $239,000

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  71 Strawberry Hill Ave Unit 320, Stamford, CT 06902

  Just a few minutes from downtown, you've got everything you need close by. This gated community is well-kept and comes included with in-ground pool, Owner and guest parking, 24-hour security, a playground, and a gym. Heat, water, and cooking gas are all included in the common charges. It's move-in ready and has been well cared for over the years. Whether you are an investor, or first time home

  Caleb Faustin Faustin Realty Group

  71 Strawberry Hill Ave Unit 320, Stamford, CT 06902
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  /37

  $8,995,000

  $755K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 11,567 Sq Ft

  31 Sawmill Ln, Greenwich, CT 06830

  Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot

  Joseph Barbieri Sotheby's International Realty

  31 Sawmill Ln, Greenwich, CT 06830
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  /55

  $5,495,000

  $500K PRICE DROP

  • 3 Beds
  • 5 Baths
  • 5,305 Sq Ft

  135 & 129 Zaccheus Mead Ln, Greenwich, CT 06831

  LOCATION ,LOCATION, LOCATION! Striking, sophisticated, & contemporary w/a true WOW factor. This exceptional residence is tucked within the celebrated Golden Triangle, surrounded by some of Greenwich's most prominent estates. A rare blend of timeless modern sensibility, the home showcases stunning interiors, refined elegance, & impeccable craftmanship. Designed for today's lifestyle, the layout

  Janet Milligan Sotheby's International Realty

  135 & 129 Zaccheus Mead Ln, Greenwich, CT 06831
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  /14

  $28,500,000

  • 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 with 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 Inc.

  39 Brookridge Dr, Greenwich, CT 06830
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  /19

  $629,500

  • 2 Beds
  • 2 Baths
  • 1,371 Sq Ft

  25 Forest St Unit 6L, Stamford, CT 06901

  Welcome to elevated city living in the heart of downtown Stamford. This stunning 2-bedroom luxury high-rise condo offers 1,371 sq ft of sun-filled living space, hardwood floors throughout, designer finishes, and unmatched convenience just minutes from Manhattan. Perfectly positioned in downtown Stamford, you're a 3-minute walk to 50+ restaurants and bars, steps from CVS, the Avon Theatre and

  Alexander Walton RE/MAX Heritage

  25 Forest St Unit 6L, Stamford, CT 06901
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  /60

  $7,450,000

  $500K PRICE DROP

  • 5 Beds
  • 9 Baths
  • 8,911 Sq Ft

  74 Rock Maple Rd, Greenwich, CT 06830

  Set on four beautifully landscaped acres in Greenwich, 74 Rock Maple Road is a classic Georgian-style residence that blends timeless architecture with exceptional modern amenities. Recently updated with a stunning new kitchen and beautifully renovated bathrooms, the home is designed for both elegant entertaining and comfortable everyday living. Gracious sun-filled interiors, a thoughtful floor

  Jenny Allen Compass Connecticut, LLC

  74 Rock Maple Rd, Greenwich, CT 06830
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  /28

  $380,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,082 Sq Ft

  1 Landmark Square Unit 217, Port Chester, NY 10573

  Welcome to 1 Landmark Square #217, a spacious one-bedroom, one-bath condominium located within the iconic Landmark Condominium, the beautifully restored former Life Savers Building and one of Westchester County's most historic and recognizable buildings. Rich in architectural character, the building showcases soaring ceilings, oversized factory windows, and original industrial details that

  Samuel Lombara Keller Williams Realty Group

  1 Landmark Square Unit 217, Port Chester, NY 10573
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  /40

  $675,000

  • 4 Beds
  • 3 Baths
  • 1,491 Sq Ft

  28 Ridgewood Ave, Stamford, CT 06907

  Welcome to this spacious 4-bedroom, 3-full-bath home set on a desirable corner lot with two driveways offering plenty of off-street parking. Inside, you'll find a comfortable and versatile layout featuring hardwood floors, a bright living room, dining area, and two bedrooms conveniently located on the main level. Upstairs are two additional generously sized bedrooms and a full bath. The finished

  Justin Michael Morhunsky Sunbelt Sales & Development

  28 Ridgewood Ave, Stamford, CT 06907
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  /37

  $1,189,000

  • 5 Beds
  • 2 Baths
  • 2,118 Sq Ft

  42 Gerry St, Greenwich, CT 06830

  Welcome to 42 Gerry Street, a thoughtfully updated two-family property where the big-ticket improvements are already checked off the list, so you can spend more time enjoying the investment and less time making repair calls. Both units were renovated within the last two years, with the upper-level unit receiving the most recent refresh, including a brand-new dishwasher, newer appliances, and

  Daniel Durante Criterion Real Estate LLC

  42 Gerry St, Greenwich, CT 06830
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  /40

  $315,000

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft

  91 Strawberry Hill Ave Unit 533, Stamford, CT 06902

  Here is YOUR opportunity to join this robust community. Conveniently located in the heart of downtown Stamford! Each room in this 2 bedroom unit is oversized and offers ample room to stretch out. Primary bedroom offers a wall of closets and is huge! The 2nd bedroom is a good size and has a large closet. Updated full bathroom with tub/shower combination. There are SO many closets in this unit you

  Arlene Bubbico Coldwell Banker Realty

  91 Strawberry Hill Ave Unit 533, Stamford, CT 06902
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  /18

  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 3,254 Sq Ft

  77 Havemeyer Ln Unit 11, Stamford, CT 06902

  Welcome to this beautifully maintained townhouse offering the perfect blend of comfort, style, and convenience. Filled with natural light, this spacious home features an open-concept floor plan, an updated kitchen with modern finishes, generous living and dining areas, and well-appointed bedrooms designed for everyday living. Enjoy seamless indoor-outdoor living with a private patio, perfect for

  Cecilia Fernandez Anderson Associates LTD

  77 Havemeyer Ln Unit 11, Stamford, CT 06902
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  /40

  $14,500,000

  • 6 Beds
  • 8 Baths
  • 8,738 Sq Ft

  379 Ocean Dr W, Stamford, CT 06902

  Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal

  Joshua Weisman William Raveis Real Estate

  379 Ocean Dr W, Stamford, CT 06902
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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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  /35

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  77 Havemeyer Ln Unit 310, Stamford, CT 06902

  Experience the perfect blend of luxury, convenience, and resort-style amenities in Palmer Hill, a premier gated community nestled on the Greenwich/Stamford border. This beautifully updated second-floor midrise home offers effortless single-level living. Flooded with natural light, walls of windows in every room showcase serene, park-like views of the courtyard's flowering trees. Flexible living

  Bradley Brammer William Pitt Sotheby's Int'l

  77 Havemeyer Ln Unit 310, Stamford, CT 06902
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  /9

  $1,075,000

  Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,183 Sq Ft

  45 Hemlock Dr, Stamford, CT 06902

  Welcome to Your Westover Oasis! Set on a quiet, tree-lined street in one of Stamford's most desirable neighborhoods, this inviting 3-bedroom, 3-bath Ranch offers easy living, wonderful indoor-outdoor spaces, and a fabulous pool setting. The main level is open and airy, featuring a spacious Living Room with gas fireplace, lovely Dining Room overlooking the beautiful yard and pool, and a

  Geri Guzinski William Pitt Sotheby's Int'l

  45 Hemlock Dr, Stamford, CT 06902
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  /32

  $5,850,000

  • 5 Beds
  • 6 Baths
  • 4,946 Sq Ft

  21 Pecksland Rd, Greenwich, CT 06831

  One level living at its best! A gated drive introduces this beautifully appointed stone residence, gracefully set on over two exquisitely landscaped Mid-Country acres. Light-filled interiors offer a rare combination of scale and comfort, and are defined by dramatic ceiling heights, expansive windows, and beautifully proportioned spaces. A generous entry flows to the formal dining and living

  Leslie McElwreath Sotheby's International Realty

  21 Pecksland Rd, Greenwich, CT 06831
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  /16

  $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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  /40

  $1,900,000

  • 4 Beds
  • 5 Baths
  • 3,164 Sq Ft

  47 Summit Ridge Rd, Stamford, CT 06902

  Modern Sophistication Meets Suburban Serenity in Westover - Tucked away on a tranquil cul-de-sac, this recently built architectural gem offers a masterclass in modern living, blending refined elegance with the vibrant energy of nearby downtown Stamford. The residence unfolds through a dramatic two-story foyer into a sun-drenched, open-concept sanctuary, where a chef-inspired kitchen-adorned with

  Jaime Sneddon William Pitt Sotheby's Int'l

  47 Summit Ridge Rd, Stamford, CT 06902
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  /33

  $465,000

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft

  25 Forest St Unit 4F, Stamford, CT 06901

  Experience refined luxury living at The Classic, one of downtown Stamford's most prestigious high-rise residences. This fully remodeled 1BR 1BA condominium blends sophisticated design with exceptional convenience, creating the perfect urban retreat. The elegant doorman building welcomes residents with a beautifully appointed lobby. Inside, the sun-drenched unit showcases brand-new designer

  Aaron Ramkalawan Keller Williams Prestige Prop.

  25 Forest St Unit 4F, Stamford, CT 06901
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  /47

  $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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  /21

  $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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