Old Greenwich, CT Houses for Sale

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  /33

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 2,099 Sq Ft

  131 Henry St, Greenwich, CT 06830

  Welcome to this completely renovated 3-bedroom, 3.5-bath luxury home in Greenwich. This stunning residence has been fully updated from top to bottom, featuring a brand-new roof, plumbing, and electrical systems. Designed for modern living, the home offers high-efficiency appliances, Andersen windows, central air, gas furnace, and a tankless water heater-ensuring comfort, performance, and low

  

  Federico Martinez

  Keller Williams Prestige Prop.

  (203) 793-6238

  131 Henry St, Greenwich, CT 06830
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  /40

  $1,750,000

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

  47 Hollow Tree Ridge Rd, Darien, CT 06820

  PRICE ADJUSTMENT. 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 those seeking rental income. Historic Charm, Modern Comfort: *

  

  Karen Finn

  Gatehouse Realty Inc

  (475) 325-5924

  47 Hollow Tree Ridge Rd, Darien, CT 06820
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  /10

  $1,799,000

  • 4 Beds
  • 3 Baths
  • 2,480 Sq Ft

  116 Hillcrest Park Rd, Greenwich, CT 06870

  House sits on 1.29 acres back lot off private road boarding with wooded and wetlands, tongue and groove cedar siding with stone veneer, asphalt roof, central a/c, heat and central vacuum, vaulted ceilings, stone veneer fireplaces, second floor deck wrapping around side and back overlooking wooded and wetland areas, five-minute drive to I95 or Merritt Parkway, five-minute walk to elementary

  David White OwnerEntry.com

  116 Hillcrest Park Rd, Greenwich, CT 06870
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  /38

  $6,300,000

  • 9 Beds
  • 6.5 Baths
  • 6,841 Sq Ft

  78 Khakum Wood Rd, Greenwich, CT 06831

  78 Khakum Wood occupies a premier position in one of Greenwich's most distinguished private enclaves. Originally envisioned by Newton Phelps Stokes and developed in collaboration with the renowned Olmsted Brothers, this exceptional property is set on 2.95 beautifully landscaped acres. The residence showcases its charming Tudor architecture with the characteristic pitched gabled roof, decorative

  Deborah Huffard Houlihan Lawrence

  78 Khakum Wood Rd, Greenwich, CT 06831
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  /40

  $2,125,000

  • 5 Beds
  • 3.5 Baths
  • 4,154 Sq Ft

  75 Saddle Rock Rd, Stamford, CT 06902

  Nestled at the edge of Shippan Point, this stunning coastal retreat offers modern luxury and serene water views just moments from the Long Island Sound. Built in 2011 above the flood plain-with a transferable FEMA policy under $800/year-this 5-bedroom, 3.5-bath home combines timeless design with practical comfort across a light-filled, open layout. The heart of the home is a gourmet kitchen with

  Ryan Dichter Compass Connecticut, LLC

  75 Saddle Rock Rd, Stamford, CT 06902
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  /47

  $6,500,000

  • 5 Beds
  • 10 Baths
  • 7,632 Sq Ft

  21 Calhoun Dr, Greenwich, CT 06831

  Welcome to ''Park Hill'', a reimagined 1923 English Manor in a Prestigious Private Association. Thoughtfully refreshed for modern living while preserving the architectural character that makes it timeless. Set on 1.81 private, park-like acres, this 7,632 sq. ft. manor blends historic charm with contemporary luxury in a way few properties can. 1923 English Tudor Revival with 2025 updates. Rare

  Danielle Claroni Sotheby's International Realty

  21 Calhoun Dr, Greenwich, CT 06831
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  /23

  $470,000

  • 2 Beds
  • 2 Baths
  • 1,125 Sq Ft

  238 Madison Ave, Port Chester, NY 10573

  Make this charming two-bedroom, two-bath home your new home TODAY! Thoughtfully maintained, this home features high ceilings, skylights, LED recessed lighting, and gleaming hardwood floors throughout. The modern kitchen showcases granite countertops, a stove with hood, and state-of-the-art stainless-steel appliances, including a premium refrigerator. The partially finished, waterproofed basement

  Onyinyechi Ekpecham Keller Williams Realty NYC Grp

  238 Madison Ave, Port Chester, NY 10573
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  /43

  $24,950,000

  • 10 Beds
  • 19 Baths
  • 17,878 Sq Ft

  97 Pecksland Rd, Greenwich, CT 06831

  Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

  Robert Johnson Brown Harris Stevens CT, LLC

  97 Pecksland Rd, Greenwich, CT 06831
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  /35

  $750,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  95 Byram Rd, Greenwich, CT 06830

  Welcome to this absolutely charming 1932 cottage-style home, nestled on a picturesque .15-acre lot in the R-6 Zone of Greenwich, Connecticut. This delightful home features a newer kitchen equipped with modern appliances, perfect for culinary enthusiasts. The interior boasts refinished hardwood floors throughout, creating a warm and inviting atmosphere. Freshly painted, this residence is move-in

  Stephen Archino Sotheby's International Realty

  95 Byram Rd, Greenwich, CT 06830
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  /49

  $3,499,000

  • 5 Beds
  • 4.5 Baths
  • 5,389 Sq Ft

  399 Stanwich Rd, Greenwich, CT 06830

  Set amid scenic beauty, this custom-built Colonial offers over 5,300± square feet of elegant living space across four levels, complete with an indoor swimming pool and a charming guest cottage. Sun-filled formal living and dining rooms showcase soaring ceilings and beautiful natural light, while the kitchen with breakfast room opens to a comfortable family room. The serene primary suite provides

  Leslie McElwreath Sotheby's International Realty

  399 Stanwich Rd, Greenwich, CT 06830
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  /6

  $1,700,000

  • 6 Beds
  • 4.5 Baths
  • 7,600 Sq Ft

  12 Old Mill Ln, Stamford, CT 06902

  Great Opportunity!! Amazing Home waiting for your touch in the Newfield Area, one hour to New York City. Close to major highways, public transportation, golf course. Subject to Bank Approval. Don't let this opportunity pass by.

  Jennifer Ramirez Smart Realty

  12 Old Mill Ln, Stamford, CT 06902
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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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  /23

  $1,495,000

  • 4 Beds
  • 3 Baths
  • 2,180 Sq Ft

  77 Maple St, Darien, CT 06820

  This classic colonial offers spacious, light-filled living and dining areas anchored by a recently renovated eat-in kitchen. A comprehensive renovation and expansion in 2007 brought modern systems, updated finishes, and a more functional layout, giving the home the fresh feel of a much newer build. With four bedrooms-three upstairs plus a generous first-floor guest room-and an optional fifth

  Genevieve Schettino Compass Connecticut, LLC

  77 Maple St, Darien, CT 06820
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  /36

  $1,899,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,977 Sq Ft

  18 Sound Beach Ave, Old Greenwich, CT 06870

  The build is complete - welcome to 18 Sound Beach Avenue! This exceptional NEW 4-bedroom, 3.5-bathroom home has been fully reconfigured and thoughtfully designed with modern elegance and functionality in mind. The exterior showcases timeless white James Hardie siding, sleek black windows, and clean architectural lines that create striking curb appeal. Step inside to a bright, open-concept main

  Karly Worth Call It Closed Realty

  18 Sound Beach Ave, Old Greenwich, CT 06870
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  /40

  $3,500,000

  • 6 Beds
  • 7.5 Baths
  • 8,543 Sq Ft

  177 Long Close Rd, Stamford, CT 06902

  Perched high on a scenic knoll off a private road and set on nearly 4 acres of manicured grounds, this timeless estate is a rare opportunity to own one of Westover's most distinguished properties. Showcasing an 8,543 sq ft Georgian brick manor, built in 1989 with masterful attention to quality and detail, this renovated home offers a luxurious lifestyle with warmth and sophistication throughout.

  Anthony Ardino William Raveis Real Estate

  177 Long Close Rd, Stamford, CT 06902
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  /30

  $8,750,000

  • 5 Beds
  • 8 Baths
  • 9,619 Sq Ft

  10 Birch Ln, Greenwich, CT 06830

  Impeccably constructed colonial in Greenwich's Golden Triangle on 1.35 acres with pool bordered by a scenic pond. A double-height foyer leads to the formal living room and library, both with fireplaces. Chef's kitchen adjoins the family room with fireplace, butler's pantry, and formal dining room. French doors open to terrace with heated pool, barbecue and firepit. Mudroom and attached 4-car

  Joseph Barbieri Sotheby's International Realty

  10 Birch Ln, Greenwich, CT 06830
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  /40

  $759,000

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  78 Warren St, Stamford, CT 06902

  Welcome to Stamford! Voted as one of the best places to live in Connecticut... it's a vibrant city that will not disappoint! Fall love with this beautifully updated home, located in the coveted "Cove" neighborhood. Set up as a magnificent single-family residence...you'll have the ability to convert (or expand) it into a 2 family, due to its current R5 Zone (should you choose). From the vaulted

  Daniel D. Thomas D. Thomas Homes

  78 Warren St, Stamford, CT 06902
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  /22

  $599,000

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft

  172 Joffre Ave, Stamford, CT 06905

  Back on market - Multiple offers previously received. Inspection complete with no issues and appraisal exceeded list price! A rare second chance for qualified buyers.Welcome to this immaculate, fully renovated home in the highly desirable Newfield neighborhood! This beautifully and elegantly redone residence truly has the wow factor-just move right in and enjoy. Offering 2 bedrooms, 2 additional

  Terez DePasquale William Pitt Sotheby's Int'l

  172 Joffre Ave, Stamford, CT 06905
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  /39

  $13,995,000

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

  7 Parsonage Rd, Greenwich, CT 06830

  An extraordinary newly constructed residence in the heart of Greenwich, Seven 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 designed living

  Leslie McElwreath Sotheby's International Realty

  7 Parsonage Rd, Greenwich, CT 06830
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  /36

  $1,000,000

  • 5 Beds
  • 4 Baths
  • 3,252 Sq Ft

  136 Knobloch Ln, Stamford, CT 06902

  HIGHEST AND BEST SUBMISSIONS BY MONDAY 12/8/25 BY 5PM. Location, Location, Location! An exceptional opportunity in a sought-after Westover cul-de-sac neighborhood, this home sits on 1.4 acres of level, usable land with city water and city sewer. Thoughtfully designed, it offers generous rooms, great flow, and abundant natural light-an ideal canvas ready to shine again with your personal touch.

  Karen Sheftell William Pitt Sotheby's Int'l

  136 Knobloch Ln, Stamford, CT 06902
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  /37

  $18,500,000

  • 6 Beds
  • 9 Baths
  • 10,275 Sq Ft

  41 Meadow Wood Dr, Greenwich, CT 06830

  With breathtaking views of Long Island Sound, this custom-built Mediterranean-style home is nestled in an exclusive gated community known as Quarry Farm in Belle Haven. Featuring a terracotta-tiled roof, this luxurious home boasts 6-bedrooms and 6.3 baths on 4.7 acres of land. The central courtyard, which serves as the heart of the home, is surrounded by common living areas with extra-height

  Jennifer Ho Douglas Elliman of Connecticut

  41 Meadow Wood Dr, Greenwich, CT 06830
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  /34

  $8,250,000

  • 6 Beds
  • 9 Baths
  • 9,295 Sq Ft

  34 Dublin Hill Rd, Greenwich, CT 06830

  Ideally located on a picture-perfect cul-de sac, this Shingle Style house has had just one owner since it was built in 2005. A well-conceived 9,295 +/-SF floor plan comprises six bedrooms, seven full bathrooms and two powder rooms, plus five fireplaces. High ceilings invite an abundance of light, while exquisite millwork, rich hardwood floors and a desirable layout highlight the appealing

  Leslie McElwreath Sotheby's International Realty

  34 Dublin Hill Rd, Greenwich, CT 06830
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  /37

  $775,000

  • 3 Beds
  • 1.5 Baths
  • 1,568 Sq Ft

  90 Courtland Hill St, Stamford, CT 06906

  Welcome to this updated Colonial in the neighborhood of Glenbrook! Featuring three bedrooms, multiple baths, and flexible bonus rooms, this home offers a layout designed for both comfort and versatility. The main level includes a dining room that opens to a bright kitchen with quartz countertops and stainless-steel appliances, a separate living room, and a family room. A convenient half bath

  Jose Javier Flores BHHS Darien/New Canaan

  90 Courtland Hill St, Stamford, CT 06906
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  /28

  $997,000

  • 3 Beds
  • 3 Baths
  • 3,150 Sq Ft

  105 Houston Terrace, Stamford, CT 06902

  Single family home in The Cove. Walk to Beach, walk to public transportation, moments to I-95 at Exit 9. Can launch your boat at the Cove Harbor Marina/ramp with permit. Cove Park also offers Basketball, Tennis Courts, Ice Rink (indoor), and many acres of natural beauty (Stamford charges to access by the day). RARE OPPORTUNITY to live in a newly reconstructed home while keeping the home to a size

  Heide Moeller Coldwell Banker Realty

  105 Houston Terrace, Stamford, CT 06902
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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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  /34

  $22,000,000

  • 7 Beds
  • 5.5 Baths
  • 6,166 Sq Ft

  36, 38, 0 Game Cock Rd, Greenwich, CT 06830

  36, 38 and 0 Game Cock Road make up this 1.1+ acre island property that has been enjoyed as a multi generational family compound. One of only a few Island properties in Greenwich, let alone the Connecticut shoreline, to have it's own private bridge for access. The property boasts a 7 bedroom, 5 bath 6166 SQ FT main house, 3 en-suite bedroom 3238 SQ FT guest house, boathouse for entertaining,

  Brett Smith Brown Harris Stevens CT, LLC

  36, 38, 0 Game Cock Rd, Greenwich, CT 06830
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  /40

  $2,495,000

  • 7 Beds
  • 5.5 Baths
  • 6,268 Sq Ft

  31 Gray Farms Rd, Stamford, CT 06905

  31 Gray Farms Rd nails the wish list for today's buyer: new construction, high-end finishes, space to entertain, and a location that can't be beat. Over an acre in Stamford's Newfield area, the home is surrounded by other new builds and minutes to trains MetroNorth (NYC)/Amtrak, I-95, the Merritt Parkway, JCC, Sterling Farms, and houses of worship. Inside, a bright two-story foyer opens to an

  Jonathan Makovsky Compass Connecticut, LLC

  31 Gray Farms Rd, Stamford, CT 06905
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  /14

  $8,995,000

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

  11 Winterset Rd, Greenwich, CT 06830

  Ring in the New Year At Your New House — where modern luxury meets timeless Mid-Country living. This 10,000+ sq ft new construction is the latest offering by Ritzzo Development. Highlights include six en-suite bedrooms, 3rd floor room ready for a golf simulator, a custom Sub-Zero/Wolf kitchen w breakfast area, family room w striking wood burning hearth, oversized primary suite + seamless

  Amanda Bates Houlihan Lawrence

  11 Winterset Rd, Greenwich, CT 06830
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  /40

  $950,000

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft

  5 Nyselius Place, Stamford, CT 06905

  Immaculate modern LUXRY home with open floor plan ideal for entertaining, bright, sunny, spacious and inviting in the Newfield area. This luxurious and spacious 3 Bedrooms and 3 full bath Raised ranch style home with finished basement has everything. Tastefully Renovated Kitchen and bathrooms, new Central AC, gas heat, City water and public sewer. It is perfect for first time home buyer or a

  Aziz Seyal William Raveis Real Estate

  5 Nyselius Place, Stamford, CT 06905
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  /40

  $2,670,000

  • 6 Beds
  • 3.5 Baths
  • 5,031 Sq Ft

  88 Starin Dr, Stamford, CT 06902

  Experience resort-style living at 88 Starin Drive, a striking architectural estate set on over 4 acres of privacy in Stamford. Designed with dramatic volume and incredible natural light, this sprawling single-level ranch offers more than 5,000 square feet of sophisticated living space framed by walls of glass, soaring ceilings, and seamless indoor-outdoor flow. A spectacular floor-to-ceiling

  Daniel Leyden KW Legacy Partners

  88 Starin Dr, Stamford, CT 06902
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  /38

  $7,699,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 7,028 Sq Ft

  48 Lexington Ave, Greenwich, CT 06830

  Extraordinary new construction crafted by a highly regarded local builder. Every detail of this 5-bedroom, 5.1-bathroom home timeless design exudes excellence offering the best that in-town living can be! Tucked away on a quiet street, it offers the perfect balance of privacy and convenience to everything downtown Greenwich has to offer. An open floor plan, meticulously crafted with exceptional

  Stacy Young William Raveis Real Estate

  48 Lexington Ave, Greenwich, CT 06830
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  /28

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,172 Sq Ft

  30 Lenox Ave, Stamford, CT 06906

  A large colonial in the heart of Glenbrook. This home has 3 bedroom, 2 full bathrooms and a half bathroom, a large living room, formal dining room. Hardwood floors throughout. Finished walk out basement. A must see.

  Valeria Amarante Century 21 Scala Group

  30 Lenox Ave, Stamford, CT 06906
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  /16

  $4,250,000

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

  6 Benedict Place, Greenwich, CT 06830

  Welcome to this newly renovated 3,500 sq ft gem nestled in the heart of downtown Greenwich, CT. A quick walk to MetroNorth and steps away from the amenities, restaurants and shops, this unique space is designed with the modern executive or family in mind. The home seamlessly blends comfort, functionality, and style and can be adapted effortlessly to suit your needs.Benedict Place is

  Wendy Hill Sotheby's International Realty

  6 Benedict Place, Greenwich, CT 06830
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  /26

  $2,285,000

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  200 Davis Ave, Greenwich, CT 06830

  Beautifully updated and move-in ready, this bright 3-bed, 2-bath home offers a prime in-town location moments from shops, parks, and train. Features include a sun-filled living room, modern kitchen with stainless appliances, spacious bedrooms, and a private backyard perfect for entertaining. Enjoy ease of living close proximity to all Greenwich amenities. A rare opportunity for convenience,

  Stephen Archino Sotheby's International Realty

  200 Davis Ave, Greenwich, CT 06830
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  /9

  $3,995,000

  • 4 Beds
  • 2.5 Baths
  • 3,650 Sq Ft

  30 Milbank Ave, Greenwich, CT 06830

  Welcome to The Robert Mead House - a magnificent 1854 Federal with a prominent downtown location in Greenwich. Sensitively preserved and extensively renovated over the past 18 years, this elegant building has immense character and charm. Large scale rooms, 12' ceiling height with beautiful mill work and tall windows throughout. With many different ways to enjoy this property please see

  B.K. Bates Houlihan Lawrence

  30 Milbank Ave, Greenwich, CT 06830
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  /45

  $6,500,000

  • 6 Beds
  • 8 Baths
  • 5,590 Sq Ft

  16 Martin Dale N, Greenwich, CT 06830

  Exceptional design and the finest craftsmanship defines this pristine, all-ensuite 6-bedroom home on one of central Greenwich's highly coveted streets. Soaring ceilings, white oak wood flooring, a gourmet kitchen, all Waterworks bathrooms, solid Mahogany windows, and bespoke European materials encompass the home. With a smart flow and endless light, the first floor is captivating offering a

  Meg McQuillan Sotheby's International Realty

  16 Martin Dale N, Greenwich, CT 06830
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  /64

  $16,750,000

  • 5 Beds
  • 9 Baths
  • 13,031 Sq Ft

  50 Dingletown Rd, Greenwich, CT 06830

  Peace and tranquility amid 7.37 lush acres, just minutes from Downtown Greenwich: this is Harkaway Farm, a distinguished Georgian Colonial estate set behind stately stone pillars and impressive gates. A meandering drive carries you over a stone bridge fording a gentle stream, to the recently transformed home. Built exceptional craftsmanship the facade of the stately manner was preserved and

  Francine Ehrlich Sotheby's International Realty

  50 Dingletown Rd, Greenwich, CT 06830
• 

  

  /23

  $1,675,000

  • 4 Beds
  • 3.5 Baths
  • 3,892 Sq Ft

  151 Hamilton Ave, Greenwich, CT 06830

  Beautifully refreshed, this inviting 4-bedroom home blends classic character with modern comfort just moments from downtown Greenwich. As one of only two homes in a Planned Unit Development, this charming home features an updated kitchen that opens to a comfortable family room, along with a welcoming living room and formal dining room - ideal for both everyday living and entertaining. The second

  Joanne Mancuso Houlihan Lawrence

  151 Hamilton Ave, Greenwich, CT 06830
• 

  

  /22

  $649,900

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

  28 Aquila Rd, Stamford, CT 06902

  LIVE THE COVETED COASTAL LIFESTYLE IN STAMFORD'S SOUGHT-AFTER COVE PARK COMMUNITY. Just one block from the beach, this picture-perfect Cape Cod home sits on a quiet cul-de-sac with a large, flat lot and views of the Long Island Sound right from your front door. Whether you're ready to move right in or envision expanding, this property offers rare flexibility in an unbeatable location. Enjoy

  Jennifer Gainer Preston Gray Real Estate

  28 Aquila Rd, Stamford, CT 06902
• 

  

  /35

  $5,575,000

  • 6 Beds
  • 8 Baths
  • 6,520 Sq Ft

  25 Dialstone Ln, Riverside, CT 06878

  Experience exceptional craftsmanship in this new construction 6-bedroom, 6.2-bath home on a desirable Riverside cul-de-sac. Spanning over 6,500 sq. ft. across four levels, this thoughtfully designed residence blends luxury, comfort, and convenience. The main level features 10-foot ceilings, white oak floors, and a dramatic double-height family room with a gas fireplace. The show-stopping eat-in

  Jennifer Leahy Compass Connecticut, LLC

  25 Dialstone Ln, Riverside, CT 06878

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