Homes for Sale in Old Greenwich, CT with 5-Bedrooms

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  /4

  $2,525,000

  • 8 Beds
  • 3 Baths
  • 3,443 Sq Ft

  2646 Boston Post Rd, Darien, CT 06820

  Home with seasonal water views of Holly Pond. Present use: Boarding House. Sold "As Is".

  Angela Abate William Raveis Real Estate

  2646 Boston Post Rd, Darien, CT 06820
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• 

  

  

  /22

  $4,375,000

  • 5 Beds
  • 4.5 Baths
  • 3,384 Sq Ft

  118 Shore Rd, Old Greenwich, CT 06870

  Charming stone-front Shore Colonial ideally located south of Old Greenwich Village and on a quiet corner lot along desirable Ballwood Rd. This classically designed home offers 3 levels of relaxed, coastal living, featuring an open-concept kitchen and family room with expansive windows and doors that lead to a level, fenced backyard.Enjoy seamless indoor-outdoor entertaining with a large stone

  Tracey Koorbusch Sotheby's International Realty

  118 Shore Rd, Old Greenwich, CT 06870
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  /35

  $3,145,000 Open Sat 11AM - 1PM

  • 6 Beds
  • 5.5 Baths
  • 4,300 Sq Ft

  20 Sound Beach Ave, Greenwich, CT 06870

  NEW BUILD in Old Greenwich, close to BEACH! Greeted with Wide Plank White Oak hardwood floors and high end finishes throughout the home, it truly is a masterpiece. Open-concept Kitchen is full of gold accent fixtures and JennAir appliances, with a large waterfall Quartz Carrara Gold Island. Entertain your guests while admiring the electric heating fireplace in the living room which also has

  Kaltrina Xhema-Latifi Higgins Group Greenwich

  20 Sound Beach Ave, Greenwich, CT 06870
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  /38

  $2,490,000

  • 5 Beds
  • 5.5 Baths
  • 2,885 Sq Ft

  65 Sherwood Place, Greenwich, CT 06830

  Exquisite individual custom built 2014 condominium unit it a two unit complex. Prime In Town location, walk to Greenwich Avenue. Unit has four levels with four bedrooms and three baths on second floor, Bedroom and bath on attic level. Bedroom and full bath with fireplace on lower level.

  Scott Kelland CLS Group

  65 Sherwood Place, Greenwich, CT 06830
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  /7

  $639,999

  • 5 Beds
  • 2.5 Baths
  • 1,396 Sq Ft

  533 Willett Ave, Port Chester, NY 10573

  Home being sold AS IS. This is a legal 1 Family, owner using as a 2 Family. Can be converted plans in building dept. Entire home powered by electric.Gas turned off, boiler not being used. Make offers.

  Kathleen Zaccagnino Rye Port Real Estate, Inc.

  533 Willett Ave, Port Chester, NY 10573
• 

  

  /11

  $949,000

  • 6 Beds
  • 3 Baths
  • 2,037 Sq Ft

  128 Terrace Ave, Port Chester, NY 10573

  Three family house in the Village of Port Chester. Detach car garage. Excellent opportunity for a 1st time homeowner and collect rent.

  Beatriz Alvarez West Green + Assoc RE Brokers

  128 Terrace Ave, Port Chester, NY 10573
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  /18

  $985,000

  • 5 Beds
  • 2 Baths
  • 2,455 Sq Ft

  72 Haig Ave, Stamford, CT 06905

  Welcome to 72 Haig Avenue, a solidly built and thoughtfully designed two-family home nestled on a peaceful, sidewalk-lined street in Stamford. Constructed in 1950 by the owner for his family, this is the first time this home has been listed for sale. This property showcases enduring craftsmanship with a brick exterior and concrete interior, offering both character and long-lasting quality. The

  Ashley Lewis Keller Williams Prestige Prop.

  72 Haig Ave, Stamford, CT 06905
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  /47

  $3,995,000

  • 5 Beds
  • 6.5 Baths
  • 4,644 Sq Ft

  73 Lockwood Rd, Riverside, CT 06878

  This is the one that you've been waiting for! Don't miss this well-maintained Riverside home with 5 bedrooms, 6.1 bathrooms, a finished third level with a private office, and a finished basement, adding an additional 1185 square feet. Enjoy the fantastic backyard complete with an outdoor fireplace, perfect for crisp evenings on the patio. Ideally located close to Riverside Elementary and Eastern

  Stefanie Lacoff BHHS New England Properties

  73 Lockwood Rd, Riverside, CT 06878
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  /40

  $1,125,000

  • 5 Beds
  • 2.5 Baths
  • 3,216 Sq Ft

  1073 Shippan Ave, Stamford, CT 06902

  Walk to the beach by summer! Welcome to this beautifully renovated Shippan Colonial that perfectly blends modern updates w/classic charm. With 5 BRs, 2.5 baths, & multiple flex spaces, this home offers comfort & versatility. An inviting front porch sets the tone, while inside, the open flow allows light to pour in from all windows. The spacious LR flows seamlessly into the DR & showstopping

  Alyssa Bernstein Berkshire Hathaway NE Prop.

  1073 Shippan Ave, Stamford, CT 06902
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  /40

  $8,995,000

  • 6 Beds
  • 6.5 Baths
  • 7,456 Sq Ft

  546 Lake Ave, Greenwich, CT 06830

  Situated on prestigious Lake Avenue in the coveted Greenwich mid-country, the storied Chadeline is a reimagined English Manor estate evoking a private European retreat. Set on 2.83 majestic riverfront acres, this fieldstone Tudor blends historic elegance with a full modern renovation. Sunlit interiors feature soaring ceilings, original details & refined finishes. At the home's epicenter, the

  Kevin Sneddon Compass Connecticut, LLC

  546 Lake Ave, Greenwich, CT 06830
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  /32

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,446 Sq Ft

  18 Thomasina Ln, Darien, CT 06820

  Thoughtfully built and meticulously maintained, this five-bedroom colonial offers four finished levels of living on a highly desirable in-town cul-de-sac. Ideally located just moments from beaches, train, downtown Darien and Darien Commons the home blends convenience with a true neighborhood feel. The bright open layout features hardwood floors throughout, detailed millwork, and a spacious

  Robin Halsey Compass Connecticut, LLC

  18 Thomasina Ln, Darien, CT 06820
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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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  /36

  $1,849,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 4,278 Sq Ft

  6 Walnut Ridge Ct, Stamford, CT 06905

  Exceptional NEW construction in a coveted mid-city location offers the perfect blend of refined comfortable living. This sensational 5-bedroom, 4.5 bathroom home with well proportioned rooms throughout, showcases sophisticated design together with an open-concept. The gourmet kitchen serves as the heart of the home, boasting a large center island, walk-in pantry, and abundant cabinet and counter

  Barbara Hickey William Pitt Sotheby's Int'l

  6 Walnut Ridge Ct, Stamford, CT 06905
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  /20

  $1,125,000

  • 6 Beds
  • 4 Baths
  • 3,034 Sq Ft

  124 Pine Hill Ave, Stamford, CT 06906

  Well-maintained and thoughtfully updated 2-family in Stamford's highly sought-after Glenbrook neighborhood. This side-by-side property features two spacious 3BR/1.5BA units, each offering a functional and modern layout ideal for both owner-occupants and investors alike. Inside, both units showcase a bright living room that flows seamlessly into an open-concept dining area and kitchen, complete

  Aaron Ramkalawan Keller Williams Prestige Prop.

  124 Pine Hill Ave, Stamford, CT 06906
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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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  /31

  $2,350,000

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

  201 Shore Rd, Greenwich, CT 06830

  On sought-after Belle Haven peninsula near town, this 2008 expanded 5 bed, 3.2 bath home boasts breathtaking Greenwich Harbor views. Perfectly designed for harborside living & entertaining, the sunlit gourmet chef's kitchen & great room boast an expansive island, custom cabinetry and a wall of windows overlooking harbor & park. The spacious living room, complete with wood burning fireplace &

  Meg McAuley Kaicher Coldwell Banker Realty

  201 Shore Rd, Greenwich, CT 06830
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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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  /30

  $835,000

  • 7 Beds
  • 2 Baths
  • 2,408 Sq Ft

  60 Stephen St, Stamford, CT 06902

  Spacious, heart of Stamford 2 Family with great potential. Newly Updated 2nd Fl-3 Bedrooms, Office Room, Living Room, Modern Eat-In Kitchen with Quartz Countertop and New Appliances; 3rd Fl-Large Bonus Room/ Bedroom and Office. 1st Fl-2 Bedrooms, Office Room/3rd Bedroom, Living Room, Eat-In Kitchen with some new appliances-New Gas Stove, New Hood, New Sink, Etc., 2 Car Garage plus additional off

  Irene Cheung BHGRE Shore & Country

  60 Stephen St, Stamford, CT 06902
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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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  /35

  $3,375,000

  • 5 Beds
  • 3.5 Baths
  • 5,213 Sq Ft

  12 Ricki-Beth Ln, Old Greenwich, CT 06870

  Tucked at the end of a quiet cul-de-sac in coveted Hillcrest Park, this superbly renovated 5-bedroom, 3.1-bath Colonial offers 5,213 square feet of refined living on 1.11 manicured acres in the heart of Old Greenwich, CT. Close distance to top-rated North Mianus Elementary School and just minutes from the Old Greenwich train station, downtown shops, and the beach, this is the rare Greenwich

  Jeffrey Jackson Corcoran Centric Realty LLC

  12 Ricki-Beth Ln, Old Greenwich, CT 06870
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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

  $2,900,000

  • 5 Beds
  • 6 Baths
  • 4,966 Sq Ft

  1 Duffys Ln, Darien, CT 06820

  Welcome to One Duffy's Lane, an exceptional 5-bedroom, 4.2-bath residence offering 4,966 square feet of refined living space on a private .65-acre lot. Perfectly positioned at the entrance of a highly sought-after cul-de-sac, this home combines timeless design with modern comfort. A spacious two-story foyer welcomes you upon entry, featuring a sweeping staircase and dramatic ceiling heights.

  Eileen Murphy William Pitt Sotheby's Int'l

  1 Duffys Ln, Darien, CT 06820
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  /40

  $2,950,000 Open Sat 1PM - 3PM

  • 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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  /34

  $3,345,000

  • 5 Beds
  • 4.5 Baths
  • 6,195 Sq Ft

  5 Middlesex Rd, Darien, CT 06820

  Step into a truly special offering- a stately New England home, thoughtfully RENOVATED and completely MOVE-IN READY. Conveniently located close to train, elementary school, downtown shopping/dining, and parks. South-facing and situated on over half an acre, this gracious residence offers 6,195 sqft of character, elegance, and modern convenience. The gourmet kitchen is thoughtfully appointed with

  Allison Santopietro William Raveis Real Estate

  5 Middlesex Rd, Darien, CT 06820
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  /5

  $1,390,000

  • 6 Beds
  • 1,560 Sq Ft

  117 North St, Stamford, CT 06901

  Unique mixed-use opportunity in the heart of Stamford! This versatile property features a residential home in the front, zoned RH, offering comfortable living with strong rental or owner-occupant potential. The rear of the property is commercially zoned and includes a grandfathered welding shop, making it ideal for contractors, tradespeople, or investors seeking an established workspace with

  Silvana Orsaia BHGRE Shore & Country

  117 North St, Stamford, CT 06901
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  /8

  $7,995,000 New Construction

  • 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. Walk 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 room

  Nina Frandson Berkshire Hathaway NE Prop.

  68 Dearfield Dr, Greenwich, CT 06831
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  /40

  $2,495,000 Open Fri 11AM - 1PM

  • 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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  /30

  $2,950,000

  • 5 Beds
  • 5.5 Baths
  • 4,539 Sq Ft

  44 Maple St, Darien, CT 06820

  Welcome to 44 Maple Street, a beautifully maintained and thoughtfully updated home in one of Darien's most convenient locations. Just half a mile from Noroton Heights' shops, dining, and train, this property makes everyday errands simple, and commuting a breeze. Originally built by Giannattasio builders in 2017 and enhanced with quality updates by Ruddy Builders, the home has been meticulously

  Amanda Spatola Houlihan Lawrence

  44 Maple St, Darien, CT 06820
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  /40

  $1,275,000

  • 7 Beds
  • 4 Baths
  • 2,340 Sq Ft

  62 Dyke Ln, Stamford, CT 06902

  Diamond in the rough. Harbor Point mixed use in need of minor upgrades to achieve a 125K NOI. 3 residential apartments, an office and 2 bay garage with loft for a total of 5 revenue streams. Walk to Koscuzo Park, Commons Park and all that Harbor Point has to offer. Nice back yard, Financials available upon request for qualified buyers.

  Daniel Kolich William Raveis Real Estate

  62 Dyke Ln, Stamford, CT 06902
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  /40

  $1,780,000 New Construction

  • 6 Beds
  • 5 Baths
  • 3,744 Sq Ft

  173 Belltown Rd, Stamford, CT 06905

  Stunning NEW CONSTRUCTION in the centrally located Springdale neighborhood of Stamford, CT. Built by a two-year HOBI Awards winner, this modern Colonial blends exceptional craftsmanship with thoughtful design. Offering 6 bedrooms and 5 full bathrooms, this home features a bright, open layout perfect for both everyday living and entertaining. The gourmet kitchen is equipped with fully integrated

  Natalia LLano Compass Connecticut, LLC

  173 Belltown Rd, Stamford, CT 06905
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  /30

  $1,495,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,119 Sq Ft

  12 Walnut Ridge Ct, Stamford, CT 06905

  Don't miss this rare opportunity to own NEW construction in a desirable mid city, cul de sac neighborhood location. One of only two homes remaining in this 10-lot subdivision. This 5 bedroom, 3.5 bath colonial is comfortably proportioned and thoughtfully designed throughout with a relaxed, transitional style. The main level features an open and welcoming floor plan that easily connects living

  Barbara Hickey William Pitt Sotheby's Int'l

  12 Walnut Ridge Ct, Stamford, CT 06905
• 

  

  /39

  $3,250,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 4 Baths
  • 4,567 Sq Ft

  18 Phillips Ln, Darien, CT 06820

  18 Phillips Lane offers a rare combination of neighborhood energy and privacy, set on one of Darien's most sought-after cul-de-sacs. Phillips Lane is known for it's close-knit community; enjoy spontaneous yard-to-yard socializing, biking on the cul de sac with friends, trick-or-treating, and walks to school. Inside, natural light pours through more than 4,200 square feet of thoughtfully designed

  Amanda Spatola Houlihan Lawrence

  18 Phillips Ln, Darien, CT 06820
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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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  /33

  $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 master 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

  • 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
• 

  

  /34

  $11,500,000

  • 6 Beds
  • 7 Baths
  • 9,081 Sq Ft

  19 Hawkwood Ln, Greenwich, CT 06830

  Set on 2 private, gated acres off North Street, this exceptional Greenwich mid-country estate offers rare privacy, timeless architecture & refined modern luxury. Originally designed in 1938 by renowned architect Nora Stanton Barney and completely rebuilt & expanded in 2005, the stately brick residence features elegant formal rooms plus relaxed indoor & outdoor living spaces. A 2021 renovation

  Kevin Sneddon Compass Connecticut, LLC

  19 Hawkwood Ln, Greenwich, CT 06830
• 

  

  /38

  $1,395,000

  • 8 Beds
  • 8.5 Baths
  • 5,530 Sq Ft

  75 Coolidge Ave, Stamford, CT 06906

  Don't miss this fabulous two-family home, where each unit lives like a 4-5 bedroom single-family house. Newly re-built in 2023, this 5530 sq ft home has so much to offer, with enough room for the whole family. Four to five bedrooms and 4 full bathrooms in each unit plus a large finished walk-up third floor in each unit and a full finished basement in unit 2, both can be used as an office, play

  Stefanie Lacoff Berkshire Hathaway NE Prop.

  75 Coolidge Ave, Stamford, CT 06906
• 

  

  /7

  $10,350,000

  • 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
• 

  

  /28

  $2,195,000

  • 6 Beds
  • 4.5 Baths
  • 10,746 Sq Ft

  677 W Hill Rd, Stamford, CT 06902

  Rare 3.75-Acre Builder Opportunity on W Hill Road Exceptional opportunity to own 3.75 private acres in one of the area's most prestigious and sought-after locations-W Hill Road. This unique property features an existing 4,400 sq ft main residence plus a separate 900 sq ft cottage, offering endless possibilities for builders, investors, or end-users seeking a private estate setting. The current

  Antonio LaRocca The LaRocca Group

  677 W Hill Rd, Stamford, CT 06902

Showing Results 41 - 80, Page 2 of 3