Old Greenwich, CT Homes for Sale with Pool

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  /24

  $599,000

  • 2 Beds
  • 2 Baths
  • 1,199 Sq Ft

  2289 Bedford St Unit G2, Stamford, CT 06905

  Welcome to this beautiful 2-bedroom, 2-bathroom condominium featuring its own private garage with additional storage in the desirable Chesterfield Condominium Assoc. This bright and inviting home offers a living room with soaring cathedral ceilings, skylights, fireplace, and new hardwood floors. The dining room and well-appointed kitchen with granite countertops and a dry bar both provide access

  Dannel Malloy NestSeekers International

  2289 Bedford St Unit G2, Stamford, CT 06905
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  /32

  $4,495,000

  • 5 Beds
  • 5.5 Baths
  • 4,259 Sq Ft

  16 Ridgebrook Rd, Greenwich, CT 06830

  Just minutes from downtown Greenwich, this beautifully renovated Colonial offers the ideal blend of luxury, comfort, and convenience. The bright, open interior features soaring ceilings, hardwood floors, a custom kitchen with stone countertops and stainless steel appliances, and an impressive great room with fireplace overlooking the backyard. Designed for today's lifestyle, all bedrooms feature

  Jose Cuartas Corcoran Centric Realty LLC

  16 Ridgebrook Rd, Greenwich, CT 06830
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  /32

  $259,000

  • 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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  /44

  $3,095,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,543 Sq Ft

  51 Dandy Dr, Cos Cob, CT 06807

  Idyllic 1.03-acre luxury oasis. Four bedroom home blends elegant design with seamless indoor-outdoor living. Sun-drenched great room boasts vaulted beamed ceilings, arched windows & French doors to expansive decks. Chef's kitchen features premium Wolf/Sub-Zero appliances, granite counters, island & breakfast bar. Formal living room/library offers custom built-ins. Primary suite features walk-in

  Jennifer O'Brien Houlihan Lawrence

  51 Dandy Dr, Cos Cob, CT 06807
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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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  /19

  $325,000

  • 1 Bath
  • 800 Sq Ft

  1 Landmark Square Unit 327, Port Chester, NY 10573

  Experience Manhattan-Style Luxury in this chic corner loft, nestled within the renowned Historic Landmark Building. The open-concept style living boasts soaring ceilings with impressive windows that flood the space with natural light. It’s the kind of airy, vibrant atmosphere that’s hard to find, perfectly complemented by a beautifully updated kitchen and a sleek, modern bathroom. Plus, you’ll

  Deirdre Coffey Compass Greater NY, LLC

  1 Landmark Square Unit 327, Port Chester, NY 10573
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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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  /32

  $2,395,000

  • 4 Beds
  • 4.5 Baths
  • 4,023 Sq Ft

  106 Pond Rd, Stamford, CT 06902

  Exceptional craftsmanship, timeless elegance, and modern luxury define this stunning 4-bedroom, 5.5-bath Colonial in coveted Westover. Situated on .46 acres of beautifully landscaped, park-like grounds, the property offers a heated pool, expansive patios, and exceptional outdoor living spaces. Built by a master craftsman with uncompromising attention to detail, this home showcases premium

  Karen Sheftell William Pitt Sotheby's Int'l

  106 Pond Rd, Stamford, CT 06902
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  /37

  $9,750,000

  • 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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  /34

  $875,000

  • 1 Bed
  • 1 Bath
  • 1,145 Sq Ft

  51 Forest Ave Unit 139, Old Greenwich, CT 06870

  Located on the top floor of Old Greenwich Gables, this bright and spacious one-bedroom home offers something truly special - soaring ceilings, a wood-burning fireplace, and a loft bathed in natural light from two skylights, currently used as both a guest room and homeoffice. The open living room feels generous and welcoming, with high ceilings and the fireplace as its centerpiece. The loft

  Stefanie Lacoff BHHS New England Properties

  51 Forest Ave Unit 139, Old Greenwich, CT 06870
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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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  /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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  /44

  $3,395,000

  Open Sun 1PM - 4PM $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,150 Sq Ft

  38 Byfield Ln, Greenwich, CT 06830

  Peaceful elegance awaits at 38 Byfield Lane. This 5BR, 4/1BA house is on a prestigious cul-de-sac with a beautiful pool and large stone patio for entertaining, all on 2.0 acres. The first floor has the DR, office, Family Room, chef style kitchen and a sunroom. Two FPs make the first floor feel cozy in the winter and the A/C makes it cool and dry in the summer. On the 2nd floor, the Primary suite

  Mark Pruner Compass Connecticut, LLC

  38 Byfield Ln, 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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  /20

  $359,000

  $10K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 1,079 Sq Ft

  50 Glenbrook Rd Unit 8E, Stamford, CT 06902

  Welcome home to Unit 8E at 50 Glenbrook Road, where city convenience seamlessly blends with comfort. Arriving at the Soundview Towers, you are greeted by a warm sense of security and community, supported by a welcoming front desk receptionist and a secure, polished lobby. Inside, this remarkably spacious 1,079 square foot residence gives you an immediate sense of openness. The layout maximizes

  Dezso Slezak Houlihan Lawrence

  50 Glenbrook Rd Unit 8E, Stamford, CT 06902
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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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  /21

  $629,500

  Open Sat 11AM - 2PM

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

  25 Forest St Unit 6L, Stamford, CT 06901

  Rarely available and ready for its next chapter, this expansive 1,371 sq ft residence offers what downtown Stamford buyers chase and seldom find: real space, a...Rarely available and ready for its next chapter, this expansive 1,371 sq ft residence offers what downtown Stamford buyers chase and seldom find: real space, all on one level, in the heart of the city. Set on the sixth floor of a brick

  Alexander Walton RE/MAX Heritage

  25 Forest St Unit 6L, Stamford, CT 06901
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  /35

  $359,000

  $39K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,295 Sq Ft

  1 Landmark Square Unit 621, Port Chester, NY 10573

  Priced to Sell Rare Penthouse Unit with Panoramic Views & Oversized Rooftop Patio at The Landmark, The Iconic 1920 Life Savers Building in Port Chester, New York. Live, Work, Play Lifestyle Opportunity. Walk to all Location including Train, Restaurants, Shops, Boat Marina, Capital Theater and all that Port Chester has to Offer. Special features include Art Deco Design, Open Concept Top floor

  Lorenzo Signorile Berkshire Hathaway HS NY Prop

  1 Landmark Square Unit 621, Port Chester, NY 10573
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  /58

  $7,950,000

  • 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

  $400,000

  Open Fri 12PM - 2PM

  • 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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  /25

  $15,000,000

  • 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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  /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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  /40

  $799,000

  Open Thu 4PM - 6PM

  • 4 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  151 5th St, Stamford, CT 06905

  Opportunity knocks in the heart of Mid City, one of Stamford's most desirable neighborhoods. This 3,200 sq ft Colonial is a rare chance to create your dream home or your next standout project, in a location that simply can't be beat. The historic charm is unmistakable, from the elegant crown molding to the oak hardwood floors that run throughout - original details just waiting to be preserved and

  Brian Barran Keller Williams Prestige Prop.

  151 5th St, Stamford, CT 06905
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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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  /29

  $660,000

  $105K PRICE DROP

  • 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, 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, and living areas around a

  Hannah Driscoll Berkshire Hathaway NE Prop.

  89 Harbor Dr Unit 206, 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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  /12

  $295,000

  $45K PRICE DROP

  • 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 #10, low HOA and additional storage. Updated appliances, new Tub surround, Bosch W/D in unit, freshly painted and professionally cleaned. Bring your design expertise to make this condo

  Jo-Ann Fiore Coldwell Banker Realty

  85 Riverside Ave Unit C5, Stamford, CT 06905
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  /26

  $1,495,000

  • 4 Beds
  • 3 Baths
  • 2,259 Sq Ft

  52 Center Dr, Old Greenwich, CT 06870

  Enjoy the summer in this 4 bedroom Old Greenwich home, where character, comfort, and outdoor enjoyment come together. The inviting living room with fireplace creates a warm and welcoming space, while the spacious family room offers additional room to relax and entertain. A lovely formal dining room provides even more space for gatherings. The eat-in kitchen flows to the deck and private fenced

  Jen Turano Compass Connecticut, LLC

  52 Center Dr, Old Greenwich, CT 06870
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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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  /34

  $589,000

  Open Sat 1PM - 4PM $30K PRICE DROP

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

  9 Old North Stamford Rd Unit 35C, Stamford, CT 06905

  Welcome to Chesterfield, Stamford's premier gated community! This beautifully maintained tri-level townhouse offers the perfect blend of comfort, privacy, convenience, and what a view!! NOTICE, the tax card for town is incorrect, this is a 2 full bathroom and one half bath, 3 level 1600 sq foot townhome, with second bedroom on lower level. Nestled on a quiet cul-de-sac this home features a

  Daniel Hayes Compass Connecticut, LLC

  9 Old North Stamford Rd Unit 35C, Stamford, CT 06905
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  /14

  $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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  /17

  $274,900

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  91 Strawberry Hill Ave Unit 927, Stamford, CT 06902

  Located in the heart of downtown Stamford, this updated 1 bedroom, 1 bathroom condo offers a convenient location just minutes from I-95, Metro North, Bedford Street, restaurants, shopping and nightlife. The unit features an updated kitchen with stainless steel appliances and a gas cooktop, a spacious living room with a fireplace, and access to a private balcony overlooking downtown Stamford. The

  Eric Chou eXp Realty

  91 Strawberry Hill Ave Unit 927, Stamford, CT 06902
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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

  $679,000

  • 2 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  2435 Bedford St Unit 17B, Stamford, CT 06905

  Quiet oasis with Mid-City convenience! Welcome to this spacious, airy 2-bedroom, 2.5-bath townhome in the coveted, gated Chesterfield II community-where comfort, convenience, and lifestyle meet seamlessly. Designed for everyday living and entertaining, the open-concept layout features a dining room and living room with a cozy fireplace and sliders to a private deck surrounded by mature trees -

  Geri Guzinski William Pitt Sotheby's Int'l

  2435 Bedford St Unit 17B, Stamford, CT 06905
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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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  /41

  $1,245,000

  • 2 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  51 Forest Ave Unit 48, Old Greenwich, CT 06870

  Enjoy this move-in condition Townhome. The primary Bedroom and Bath plus a Powder Room are on the main floor. The 2nd Bedroom and full Bath are on the Second Floor. Eat-in Kitchen, Dining area and Living Room with Fireplace open through sliding glass doors leading to the private Balcony. There are hardwood floors throughout and all rooms have been recently painted. The separate laundry room is

  Catherine Stahl Sotheby's International Realty

  51 Forest Ave Unit 48, Old Greenwich, CT 06870
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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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