Old Greenwich, CT Homes for Sale with Acreage

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  /36

  $5,495,000

  • 6 Beds
  • 8 Baths
  • 7,930 Sq Ft

  20 Sherwood Farm Ln, Greenwich, CT 06831

  Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! A stunning custom built white Georgian Colonial in the coveted mid country Sherwood Farm Association is sited on a picturesque level acre lot. This six bedroom

  

  Richard Higgins

  Higgins Group Bedford Square

  (203) 433-0559

  20 Sherwood Farm Ln, Greenwich, CT 06831
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  /31

  $13,900,000

  • 6 Beds
  • 9 Baths
  • 11,157 Sq Ft

  31 Meadow Ln, Greenwich, CT 06831

  Exceptional Tanner White ultra-luxurious six-bedroom modern residence in the estate area of Greenwich. The open floor plan with 12+ foot ceilings is filled with natural light and allows for versatile use of the dramatic formal and casual rooms, all leading to a captivating outdoor living space complete with a fireplace overlooking the serene pool with spa and verdant lawn. The interior design and

  Leslie McElwreath Sotheby's International Realty

  31 Meadow Ln, Greenwich, CT 06831
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  /28

  $6,595,000

  • 6 Beds
  • 8 Baths
  • 5,210 Sq Ft

  2 Sparrow Ln, Greenwich, CT 06830

  Redesigned in 2019 by renowned architect Doug Vanderhorn, this 6-bedroom, 6.5-bathroom home blends exceptional craftsmanship with natural light throughout. The main level features formal living and dining rooms, a private office, and an open-concept kitchen and family room, all opening to a patio and level grounds with a playground. Upstairs, the second level features 5 en-suite bedrooms,

  Jennifer Leahy Compass Connecticut, LLC

  2 Sparrow Ln, Greenwich, CT 06830
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  /42

  $13,995,000

  • 7 Beds
  • 12 Baths
  • 14,169 Sq Ft

  7 Dairy Rd, Greenwich, CT 06830

  New Luxury abounds in this meticulously crafted home, where carefully curated finishes and the highest building standards are evident throughout. Oversized European custom windows bathe the interiors in natural light, highlighting the chic modernity of the white oak floors that flow seamlessly across the main level.The heart of the home is the stunning Taj Mahal quartzite, open-plan kitchen - a

  Avi Barkai Pine Capital Ventures LLC

  7 Dairy Rd, Greenwich, CT 06830
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  /50

  $14,250,000

  • 6 Beds
  • 8 Baths
  • 9,418 Sq Ft

  52 Carriglea Dr, Riverside, CT 06878

  Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

  Stephen Archino Sotheby's International Realty

  52 Carriglea Dr, Riverside, CT 06878
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  /38

  $6,300,000

  • 9 Beds
  • 7 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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  /52

  $13,995,000

  • 5 Beds
  • 9 Baths
  • 10,431 Sq Ft

  190 North St, Greenwich, CT 06830

  Nor Tor stands as one of Greenwich's finest English Manors, an extraordinary estate spanning nearly 3.5 acres of breathtaking beauty. Meticulously preserved, the manor underwent an extensive three year restoration and expansion, completed in 2010, blending historical integrity with seamless enhancements. This masterful renovation was led by architect Ira Grandberg, resulting in a breathtaking

  Leslie McElwreath Sotheby's International Realty

  190 North St, Greenwich, CT 06830
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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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  /50

  $6,400,000

  • 5 Beds
  • 8 Baths
  • 7,492 Sq Ft

  101 Perkins Rd, Greenwich, CT 06830

  Situated high above Perkins Road on 2.6 acres this gated mid country 5 bedroom/5 bath residence is the ultimate in CHIC style and architectural SOPHISTICATION while also offering cozy comfort. It is the perfect MULTI-GENERATIONAL home: 2 wings offering privacy for all with generous central gathering spaces. This beautiful property has recently been updated by the current owner with many major

  Francine Ehrlich Sotheby's International Realty

  101 Perkins Rd, Greenwich, CT 06830
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  /40

  $5,495,000

  • 6 Beds
  • 5.5 Baths
  • 6,543 Sq Ft

  86 Wallacks Dr, Stamford, CT 06902

  Prestigious Waterfront Estate at Wallack's Point Experience the pinnacle of coastal luxury with this once-in-a-lifetime opportunity to own 1.46 acres of DIRECT Long Island Sound frontage in the gated enclave of Wallack's Point. With sweeping, unobstructed water views and nightly sunsets that feel like art, this premier waterfront property is among the most coveted on the Connecticut shoreline.

  Carla Kupiec William Raveis Real Estate

  86 Wallacks Dr, Stamford, CT 06902
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  /50

  $6,800,000

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

  21 Calhoun Dr, Greenwich, CT 06831

  Welcome to ''Park Hill'', a stunning English Tudor Revival Manor known as ''The House of Seven Gables''. Updated in 2025, this historic gem nestled in the heart of Greenwich on a 1.81-acre oversized lot, offers privacy & a unique blend of timeless elegance with modern conveniences. Located in the desirable Calhoun Drive Association, this property boasts both beauty & charm. The manor's

  Danielle Claroni Sotheby's International Realty

  21 Calhoun Dr, Greenwich, CT 06831
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  /44

  $6,750,000

  • 5 Beds
  • 9 Baths
  • 9,974 Sq Ft

  386 North St, Greenwich, CT 06830

  This 9,974 sq. ft. estate, nestled in 2.3 acres of pristine, park-like grounds, epitomizes understated luxury. A handcrafted brick façade and hand-split shingle roof frame interiors adorned with rare materials and custom millwork. A grand, 2-story foyer leads to a formal area designed for refined entertaining. The luxury primary suite provides a serene retreat with a double private office and a

  Stephen Archino Sotheby's International Realty

  386 North St, Greenwich, CT 06830
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  /34

  $5,595,000

  • 5 Beds
  • 5 Baths
  • 3,231 Sq Ft

  477 Lake Ave, Greenwich, CT 06830

  Seize the opportunity to own a rare piece of Greenwich's prestigious ''Golden Triangle.'' This exceptional 2.83-acre property, available for the first time since 1988, is a true gem, offering a private, level, and beautifully landscaped lot. With town water, gas, and sewer already in place, this is an unparalleled find. This 1962 classic brick and clapboard home spans 3,231 sq. ft. of refined

  Stephen Archino Sotheby's International Realty

  477 Lake Ave, Greenwich, CT 06830
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  /49

  $7,250,000

  • 7 Beds
  • 8 Baths
  • 8,068 Sq Ft

  2 Winding Ln, Greenwich, CT 06831

  LOCATION, LOCATION LOCATION Set back on 2 private acres very close to town & landscaped to perfection, this exquisite property with over sized salt water pool, tennis court, children's playground, exquisite gardens & entertaining terraces offer today's buyers the perfect lifestyle. 8000+sq.ft. brick residence w/ new slate composite roof features 6 bdrms/6 bths, private office., lg light filled

  Helene Barre Sotheby's International Realty

  2 Winding Ln, Greenwich, CT 06831
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  /30

  $5,900,000

  • 7 Beds
  • 4 Baths
  • 6,636 Sq Ft

  14 Zaccheus Mead Ln, Greenwich, CT 06831

  First time on the market in over 50 years, 1906 stone house fashioned after European castle with two guest cottages on 7.81 acres (2-acre zone) in the private Rock Ridge Association. Sited atop a hill surrounded by mature trees, the one-of-a-kind main house is filled with antique wood carvings, original paneling, beamed and tracery plaster ceilings. A 2-bedroom guest cottage shares the main

  Joseph Barbieri Sotheby's International Realty

  14 Zaccheus Mead Ln, Greenwich, CT 06831
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  /4

  $7,995,000 New Construction

  • 6 Beds
  • 7.5 Baths
  • 9,460 Sq Ft

  11 Winterset Rd, Greenwich, CT 06830

  Move in late summer 2025 to this Mid Country New Construction smart home on 2.16 exquisite level acres will be ready for mid fall move in. 9400+ SF of finished space on 3 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th bedroom in the walkup lower level. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular

  Amanda Bates Houlihan Lawrence

  11 Winterset Rd, Greenwich, CT 06830
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  /40

  $4,500,000

  • 6 Beds
  • 6 Baths
  • 8,107 Sq Ft

  336 Ocean Dr W, Stamford, CT 06902

  Stately Shippan Point Estate set on a rare 1.64-acre parcel with distant views of Long Island Sound, this distinguished Colonial residence offers an extraordinary living experience in Stamford's most coveted waterfront neighborhood. Included in the sale is an adjoining property with a fully renovated 1,900-square-foot Carriage House, creating a significant compound ideal for entertaining and

  Joshua Weisman William Raveis Real Estate

  336 Ocean Dr W, Stamford, CT 06902
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  /53

  $4,995,000

  • 4 Beds
  • 6 Baths
  • 5,244 Sq Ft

  34 Edgewood Dr, Greenwich, CT 06831

  Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, this masterfully renovated Colonial offers a harmonious blend of heritage architecture and sophisticated modernity. Designed to accommodate both grand-scale entertaining and intimate daily living, the residence unfolds across three levels and over 7,000 square feet of meticulously curated interiors.The

  Danielle Scialpi-Malloy Serhant Connecticut LLC

  34 Edgewood Dr, Greenwich, CT 06831
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  /40

  $1,197,000

  • 5 Beds
  • 3 Baths
  • 2,760 Sq Ft

  517 W Hill Rd, Stamford, CT 06902

  Exquisitely transformed, like-new construction! Westover close to Greenwich border w/city water & (newly connected) sewer on beautifully landscaped acre. Exceptional craftsmanship w/impressive visual appeal from every angle. Strikingly gorgeous EIK w/quartz countertops, sparkling SS (new GE convection oven w/air fryer & Miele dishwasher), open dining area, new cleverly designed dry bar & Trex

  Nicole J Bates William Raveis Real Estate

  517 W Hill Rd, Stamford, CT 06902
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  /10

  $1,600,000

  • Land
  • 1.15 Acres
  • $1,391,304 per Acre

  20 Stepping Stone Ln, Greenwich, CT 06830

  Gorgeous land on a cul de sac in the North Street School district. This land at 20 Stepping Stone Lane is a back lot, adjacent to a property with a house that is also on the market, #22 Stepping Stone Lane, 1.0 acres, $2,800,000. Land is staked, perc tests done (5 bedroom septic), small amount of wetlands in the left rear of the property. FAR is approximately 6,000 sq ft.

  Patte Nusbaum Sotheby's International Realty

  20 Stepping Stone Ln, Greenwich, CT 06830
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  /40

  $2,800,000

  • 4 Beds
  • 5 Baths
  • 4,836 Sq Ft

  22 Stepping Stone Ln, Greenwich, CT 06830

  4 bedroom/4.1 bath colonial home on 1.0 gorgeous acre on a cul-de-sac in mid-country. Built in 1976, renovated in 2005, added onto in 2015. Meticulously maintained. Family room addition in 2015, cathedral ceiling and 3 exposures for maximum light. Property has a 6 bedroom septic. Second floor family room could be a 5th bedroom.

  Patte Nusbaum Sotheby's International Realty

  22 Stepping Stone Ln, Greenwich, CT 06830
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  /40

  $4,675,000

  • 6 Beds
  • 8 Baths
  • 6,762 Sq Ft

  66 Stanton Rd, Darien, CT 06820

  Welcome to 66 Stanton Rd! Yes, that fabulous home with the beautiful VT slate roof! Sitting proudly atop 1.34 manicured acres, this handsome 1938 clapboard clad colonial demands to be noticed. This house underwent a major renovation and expansion that was completed in 2009. Entertaining spaces abound both formal and casual, perfect for hosting both gatherings intimate and large in scale. Step

  Nancy Peter Houlihan Lawrence

  66 Stanton Rd, Darien, CT 06820
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  /35

  $1,269,000

  • 4 Beds
  • 2.5 Baths
  • 3,193 Sq Ft

  656 Westover Rd, Stamford, CT 06902

  Historic Charm Meets Modern Luxury - Once the carriage house for the famed 1760s estate "The Owl's Nest," this exquisitely renovated home blends timeless charm with today's comforts. Original doors and vintage details have been preserved, while high-end updates elevate every space. Inside, enjoy 9-ft ceilings, gleaming hardwood floors, and two stunning fireplaces (one stone, one brick). The

  Karen Sheftell William Pitt Sotheby's Int'l

  656 Westover Rd, Stamford, CT 06902
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  /29

  $5,000,000

  • 5 Beds
  • 7 Baths
  • 5,071 Sq Ft

  1 Brookside Park, Greenwich, CT 06831

  Situated on a serene 1.23-acre, private street just minutes from the shops & restaurants on Greenwich Avenue, this custom 5BR/6.5BA stone and shingle home is a showcase of timeless architecture & exceptional craftsmanship, built by acclaimed builder Jonathan Sparks. A dramatic two-story foyer sets the tone for the elegant interior, where high ceilings and light filled spaces flow seamlessly

  Maria Crowley Houlihan Lawrence

  1 Brookside Park, Greenwich, CT 06831
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  /37

  $1,350,000

  • 4 Beds
  • 2.5 Baths
  • 4,831 Sq Ft

  20 Winding Brook Ln, Stamford, CT 06902

  Set in Stamford's sought-after Westover neighborhood, this beautifully updated Colonial offers space, style, and comfort in a tranquil, tree-lined setting. A two-story foyer welcomes you into sunlit interiors with hardwood floors throughout. The living room and family room each feature a gas fireplace, creating warm, inviting spaces. The kitchen boasts abundant cabinetry, stainless steel

  Chris Carozza RE/MAX Right Choice

  20 Winding Brook Ln, Stamford, CT 06902
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  /27

  $2,379,000

  • 5 Beds
  • 4 Baths
  • 4,082 Sq Ft

  116 West Ln, Stamford, CT 06905

  The perfect blend of classic charm and modern elegance in this completely remodeled and reimagined 1950 farmhouse colonial, nestled on a lush acre in the sought-after Revonah Woods area. This stunning home boasts five well-appointed bedrooms, including a versatile main-level bedroom that can serve as a home office or guest room with a full bath. An open flow concept seamlessly connects the living

  Barbara Webski William Pitt Sotheby's Int'l

  116 West Ln, Stamford, CT 06905
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  /39

  $2,799,999

  • 6 Beds
  • 9 Baths
  • 6,191 Sq Ft

  72 Little Hill Dr, Stamford, CT 06905

  72 Little Hill Drive - Stately Colonial in the Heart of Newfield Privately nestled in one of Newfield's most sought-after neighborhoods, this grand colonial offers over 6,300 sq ft of beautifully finished living space, including 6 bedrooms, 5 full and 4 half baths, and a 4-car garage. Built in 1865 and fully renovated, the home blends timeless charm with modern luxury. The expansive backyard is

  Tim DeBowes Hathaway, Inc.

  72 Little Hill Dr, Stamford, CT 06905
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  /39

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,233 Sq Ft

  90 Akbar Rd, Stamford, CT 06902

  Wonderful spacious Westover home on a lovely level private level acre + property with a tranquil pond. Light and bright with an open floor plan. Spacious living room with a fireplace open to the dining room with bay windows & scenic views of the property. There is a bright white kitchen with granite counters & stainless steel appliances with a door to deck. There are 3 bedrooms on the main level

  Elaine Parruccini William Raveis Real Estate

  90 Akbar Rd, Stamford, CT 06902
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  /52

  $4,000,000

  • 7 Beds
  • 8 Baths
  • 7,148 Sq Ft

  190 Lake Ave, Greenwich, CT 06830

  Lower Lake Avenue family compound, enter through a historic courtyard, foyer boasts hardwood and marble floors. All main house rooms open from the foyer: living room with built-ins and French doors to a terrace. Dining room with 3 exposures is light filled and has gorgeous views of the 1-acre level, fenced, beautifully landscaped property. The open, eat-in kitchen and family room are perfect for

  Patte Nusbaum Sotheby's International Realty

  190 Lake Ave, Greenwich, CT 06830
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  /52

  $2,699,000

  • 4 Beds
  • 4 Baths
  • 4,044 Sq Ft

  254 Stanwich Rd, Greenwich, CT 06830

  Welcome to your dream retreat! Discover this stunning, brightly illuminated home built in 1986 and thoughtfully renovated in 2024. Offering an expansive 4,044 sqft of beautifully designed living space, this residence features 4 bedrooms with the potential for a 5th on the main level and 5 bathrooms all nestled on a serene 1.37-acre lot in a desirable mid-country location, just minutes from town,

  Joan Suter BHHS New England Properties

  254 Stanwich Rd, Greenwich, CT 06830
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  /39

  $1,650,000

  • 4 Beds
  • 5 Baths
  • 4,663 Sq Ft

  108 Canfield Dr, Stamford, CT 06902

  Stylish new renovation and addition enhances this classic four-bedroom colonial on one quiet acre with easy access to hiking trails in Mianus River Park located in coveted Westover neighborhood. Exquisite architectural details complement the sun-filled interior with center hall entry, remodeled and expanded chef's eat-in kitchen open to sunroom with private wraparound deck; living room with

  Megan Epand Houlihan Lawrence

  108 Canfield Dr, Stamford, CT 06902
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  /39

  $2,350,000

  • 3 Beds
  • 4 Baths
  • 2,883 Sq Ft

  1 Broad St Unit PHD5, Stamford, CT 06901

  A crown jewel atop Stamford's skyline, this one-of-a-kind Penthouse Duplex crowns the top two floors of Park Tower—Stamford's tallest building and the highest residential address in Fairfield County. One of only six duplex penthouses, this 3-bedroom, 3.5-bath residence offers cinematic, east-facing views of Long Island Sound and downtown Stamford through floor-to-ceiling windows. Enjoy

  Andrei Balaj Higgins Group Real Estate

  1 Broad St Unit PHD5, Stamford, CT 06901
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  /51

  $11,400,000

  • 8 Beds
  • 10 Baths
  • 10,935 Sq Ft

  151 Old Church Rd, Greenwich, CT 06830

  ''Oak Castle Farm'', an extraordinary 7-bedroom turn-of-the-century English-style granite and shingle home, masterfully renovated and expanded under the supervision of noted architect, Alisberg Parker. Stunning 2014 transition incorporates relaxed grandeur with all modern-day luxuries. Exquisite detail, quality and scale with high ceilings throughout. Spectacular landscape and manicured grounds

  John McAtee Coldwell Banker Realty

  151 Old Church Rd, Greenwich, CT 06830
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  /42

  $27,950,000

  • 8 Beds
  • 12 Baths
  • 13,428 Sq Ft

  45 Binney Ln, Old Greenwich, CT 06870

  This unparalleled custom-built modern waterfront estate, winner of 2021 HOBI-award, is a true oasis with 300'+ water frontage, pool, guest house, boat house, spa, expansive terraces integrated with gardens and deep water pier. Joeb Moore + Partners, Arthur Dunnam for Jed Johnson Studio, Reed Hilderbrand & Prutting Custom Builders collaborated on this spectacular LEED certified 13,428 sf compound

  Ellen Mosher Houlihan Lawrence

  45 Binney Ln, Old Greenwich, CT 06870
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  /18

  $11,000,000

  • 8 Beds
  • 7 Baths
  • 8,751 Sq Ft

  111 Byram Shore Rd, Greenwich, CT 06830

  Experience panoramic views from this 1.5-acre waterfront estate. The views stretch across the Long Island Sound from Greenwich to Oyster Bay, allowing you to enjoy both sunrises and sunsets over the water- all in complete privacy from neighboring properties. This one-of-a-kind distinctive contemporary offers a truly unique blend of cutting-edge modern design and historic charm, complete with

  Julie Church Houlihan Lawrence

  111 Byram Shore Rd, Greenwich, CT 06830
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  /13

  $1,995,000

  • Land
  • 1.00 Acre
  • $1,995,000 per Acre

  33 Parsonage Rd, Greenwich, CT 06830

  Beautiful property, on a desirable road, in the heart of Greenwich. Conveniently located close to schools and downtown. Move in, renovate, or build your dream home!*newly subdivided lot, assessment and taxes determined at time of sale.

  Bryan Tunney Brown Harris Stevens CT, LLC

  33 Parsonage Rd, Greenwich, CT 06830
• 

  

  /13

  $1,995,000

  • 4 Beds
  • 2 Baths

  33 Parsonage Rd, Greenwich, CT 06830

  Beautiful property, on a desirable road, in the heart of Greenwich. Conveniently located close to schools and downtown. Move in, renovate, or build your dream home!*newly subdivided lot, assessment and taxes determined at time of sale.

  Bryan Tunney Brown Harris Stevens CT, LLC

  33 Parsonage Rd, Greenwich, CT 06830
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  /64

  $43,000,000

  • 6 Beds
  • 11 Baths
  • 11,500 Sq Ft

  579 Indian Field Rd, Greenwich, CT 06830

  This stunning 2.72 acre waterfront property in Mead Point has panoramic South and Easterly views across the Sound to Long Island, New York and to Tods Point and Riverside. Enjoy sunrises from almost every room in this custom-built stone and shingle colonial. The current owners intention to preserve the original house, was not possible, and they built new with the goal of retaining old world

  Heather Platt Sotheby's International Realty

  579 Indian Field Rd, Greenwich, CT 06830
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  /31

  $1,895,000

  • 3 Beds
  • 4 Baths
  • 2,292 Sq Ft

  101 Lewis St Unit E, Greenwich, CT 06830

  Chic and sleek design one block from Greenwich Ave. Enjoy the ease of downtown living with all amenities nearby. Leave the car at home and head to restaurants, shopping, library and coffee! This fabulous 3 bedroom end unit offers an open floor plan with upscale kitchen and access to the patio from the living and dining rooms. Hardwood floors throughout. 1 1/2 car garage allows space for a

  Laurie Meyer Brown Harris Stevens CT, LLC

  101 Lewis St Unit E, Greenwich, CT 06830
• 

  

  /9

  $11,900,000

  • 6 Beds
  • 9 Baths
  • 9,836 Sq Ft

  32 Pheasant Ln, Greenwich, CT 06830

  Welcome to 32 Pheasant Lane, a stunning completely rebuilt and expanded modern Colonial on one of Greenwich's most coveted streets. This exceptional 6 bedroom, 7.2 bath home offers over 9800 square feet of luxurious finished living space on 4 levels. An expansive front porch invites you inside where you will discover an open, airy floor plan with 10ft ceilings and custom details. White oak floors

  Maria Crowley Houlihan Lawrence

  32 Pheasant Ln, Greenwich, CT 06830

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