Old Greenwich, CT Homes for Sale with Acreage

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  /36

  $5,100,000

  • 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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  /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, masterfully renovated in 2025 this 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

  

  Danielle Malloy

  Serhant Connecticut LLC

  (203) 769-9185

  34 Edgewood Dr, Greenwich, CT 06831
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  /39

  $9,250,000

  • 5 Beds
  • 6.5 Baths
  • 6,689 Sq Ft

  101 Long Neck Point Rd, Darien, CT 06820

  Perched high on the bluff of Long Neck Point, this 6680sf custom-built brick estate offers you unmatched privacy and panoramic water views, all in this captivating natural environment where land and sea converge in harmony. Set on 1.38 acres with 175 feet of shoreline, the home enjoys 180-degree views over Long Island Sound, with main floor rooms capturing the stunning scenery and the

  Becky Munro Brown Harris Stevens

  101 Long Neck Point Rd, Darien, CT 06820
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  /38

  $9,500,000

  • 8 Beds
  • 9 Baths
  • 10,328 Sq Ft

  31 Sawmill Ln, Greenwich, CT 06830

  Extraordinary 3+acre Greenwich mid country estate in a bucolic & private setting, situated within close proximity to downtown Greenwich.This recently renovated & elegantly furnished stone Georgian Colonial blends timeless character with modern aesthetics. This substantial home features gracious & luxurious living spaces, ideal for entertaining family & friends. Architectural highlights include

  Kevin Sneddon Compass Connecticut, LLC

  31 Sawmill Ln, Greenwich, CT 06830
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  /7

  $8,750,000

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

  11 Winterset Rd, Greenwich, CT 06830

  Mid Country New Construction smart home on 2.16 exquisite level acres will be completed by early fall, 2025. 10K+ SF of finished space on 4 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th en-suite bedroom on 3rd floor. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular indoor / outdoor living is designed

  Amanda Bates Houlihan Lawrence Inc.

  11 Winterset Rd, Greenwich, CT 06830
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  /31

  $13,400,000

  • 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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  /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
  • 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

  $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 Open Sun 1PM - 4PM

  • 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 facade 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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  /49

  $6,395,000

  • 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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  /35

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

  • 5 Beds
  • 4.5 Baths
  • 4,195 Sq Ft

  25 Jeffrey Rd, Greenwich, CT 06830

  Set on 1.14 wooded acres on a quiet cul-de-sac, this spacious and well-designed home offers a rare combination of comfort, privacy, and convenience just minutes to town and train. The main level features a great room with vaulted ceilings , open living and dining areas, a private primary suite, and three additional bedrooms. The finished walk-out lower level includes a guest bedroom, full bath,

  Susan Isaak Coldwell Banker Realty

  25 Jeffrey Rd, Greenwich, CT 06830
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  /29

  $2,350,000

  • 5 Beds
  • 4 Baths
  • 3,897 Sq Ft

  76 Deepwood Rd, Darien, CT 06820

  Set on a full acre in one of Darien's most sought-after neighborhoods, this property presents a rare and versatile opportunity for visionary buyers. Whether you choose to undertake a renovation-reviving the charm of mid-century modern design-or build a custom new construction estate from the ground up, the potential here is extraordinary. Surrounded by multi-million dollar homes, this centrally

  Carolyn Brook William Pitt Sotheby's Int'l

  76 Deepwood Rd, Darien, CT 06820
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  /30

  $2,850,000

  • 5 Beds
  • 6 Baths
  • 5,320 Sq Ft

  69 Fairfield Rd, Greenwich, CT 06830

  Charming, expanded farmhouse ideally located near town and within close distance to 3 Greenwich schools. Set on a beautifully landscaped 1.05-acre lot, with exceptional privacy, lush gardens, and a flat backyard perfect for play and entertaining. With over 5,000 square feet of living space, the home includes flexible areas for every need: multiple light-filled dining spaces, dedicated offices, a

  Amanda Miller Houlihan Lawrence

  69 Fairfield Rd, Greenwich, CT 06830
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  /16

  $380,000

  • 1 Bed
  • 1 Bath
  • 985 Sq Ft

  2 Putnam Hill Unit 1K, Greenwich, CT 06830

  Enjoy the convenience of in-town living and the incredible, oversized (1,000+ sf), PRIVATE patio perfect for entertaining, relaxing, gardening and more! This spacious, first floor, 1-bedroom unit is filled with natural light and offers easy indoor/outdoor living with access to the private patio from the kitchen and large open living/dining room. Common charges include: grounds care, snow removal,

  Gloria Gimenez-Ferrer BHHS New England Properties

  2 Putnam Hill Unit 1K, Greenwich, CT 06830
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  /40

  $939,000

  • 3 Beds
  • 2.5 Baths
  • 2,970 Sq Ft

  133 Macgregor Dr, Stamford, CT 06902

  Welcome to easy living in this updated, freshly painted Westover Ranch, ideally located on a quiet cul-de-sac. Generously sized rooms and a finished lower level offer plenty of flexible space. The main level features a sunlit Living Room with fireplace, spacious Dining Room, and a refreshed Eat-In Kitchen with new quartzite counters, center island with breakfast bar, and sliders to the rear yard

  Geri Guzinski William Pitt Sotheby's Int'l

  133 Macgregor Dr, Stamford, CT 06902
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  /27

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 2,862 Sq Ft

  285 Westover Rd, Stamford, CT 06902

  Location! Welcome to an exquisite sanctuary nestled in the coveted Westover area. This stunning residence promises an elegant lifestyle with its modern touches and serene surroundings. Boasting 4 bedrooms/3.5 bathrooms this property offers a harmonious blend of sophistication and comfort. Upon entering, you'll be captivated by the chef's dream kitchen, featuring high-end appliances including a

  Noelle Iannotta Compass Connecticut, LLC

  285 Westover Rd, Stamford, CT 06902
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  /23

  $22,000,000

  • 8 Beds
  • 12 Baths
  • 14,071 Sq Ft

  8 Fox Run Ln, Greenwich, CT 06831

  Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls

  James Hoffman Houlihan Lawrence

  8 Fox Run Ln, Greenwich, CT 06831
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  /40

  $4,375,000

  • 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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  /27

  $1,999,000

  • 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

  $2,649,999

  • 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

  Anthony Gaglio Jr Hathaway, Inc.

  72 Little Hill Dr, Stamford, CT 06905
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  /51

  $4,000,000 Open Sun 1PM - 3PM

  • 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

  $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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  /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
  • 11.5 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
• 

  

  /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
  • 1.5 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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  /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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  /75

  $13,750,000

  • 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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  /20

  $1,995,000

  • 4 Beds
  • 3 Baths
  • 3,284 Sq Ft

  297 Cognewaugh Rd, Cos Cob, CT 06807

  Nestled within the serene beauty of Greenwich's sought-after Cos Cob community, this elegant property is set on two private, wooded acres. This refined 4-bedroom, 3-bathroom residence spans over 3,200 square feet of meticulously designed living space, perfect for the discerning buyer.Exquisite hardwood floors, sunlit interiors, and architectural details create an atmosphere of understated

  Mark Pruner Compass Connecticut, LLC

  297 Cognewaugh Rd, Cos Cob, CT 06807
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  /31

  $8,950,000

  • 6 Beds
  • 5.5 Baths
  • 5,040 Sq Ft

  33 Meadow Wood Dr, Greenwich, CT 06830

  In the gated Quarry Farm neighborhood of the enchanting Belle Haven Association with 24hr security, this property offers a unique opportunity to renovate or build new, 16,000+ sq ft waterfront home. Overlooking Byram Harbor and Long Island Sound, the current 6-bedroom house sits on 2.78 acres with a pool, adjacent to a 1.09-acre protected lot. Once a quarry and later acquired as part of the

  Joseph Barbieri Sotheby's International Realty

  33 Meadow Wood Dr, Greenwich, CT 06830
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  /69

  $2,730,000

  • 4 Beds
  • 4.5 Baths
  • 3,826 Sq Ft

  681 River Rd, Cos Cob, CT 06807

  Timeless , this architecturally designed contemporary home blends soaring vaulted ceilings with panoramic views, creating a seamless connection to the outdoors. Thoughtfully sited on 2.32 peaceful, private acres, the home embraces natural light as the seasons change, all while remaining minutes from every convenience possible.The open-concept floor plan is ideal for both grand entertaining

  Paula Waldman BHHS New England Properties

  681 River Rd, Cos Cob, CT 06807
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  /23

  $33,000,000

  • 8 Beds
  • 14 Baths
  • 18,954 Sq Ft

  555 Lake Ave, Greenwich, CT 06830

  Overlooking 8+park-like acres, this majestic brick Georgian was transformed to blend top of the line appointments with a rich array of custom detailing. Crowned by a 3-story chandelier, the impressive reception hall with Wenge walnut parquetry floor opens to a formal Dining Room with fireplace and elegant Living Room with fireplace and custom bar. Distinguished two-story English mahogany library

  Leslie McElwreath Sotheby's International Realty

  555 Lake Ave, Greenwich, CT 06830
• 

  

  /23

  $4,350,000

  • 6 Beds
  • 4.5 Baths
  • 4,958 Sq Ft

  121 Round Hill Rd, Greenwich, CT 06831

  Rare find - property on one of Greenwich' estate roads, Round Hill Rd. Oversized, private property, pool, stable, with a perfect blend of tranquil, manicured and natural landscapes. Enjoy your morning coffee gazing across beautiful east-facing rear vistas.Move right into this 5 bedroom 4 1/2 bath home, featuring upgrades like generator, irrigation, and largely new windows. Create your

  Sabine Schoenberg PrimeSites, Inc.

  121 Round Hill Rd, Greenwich, CT 06831
• 

  

  /17

  $7,995,000

  • Land
  • 1.90 Acres
  • $4,207,895 per Acre

  2 Vista Dr, Greenwich, CT 06830

  Stunning waterfront building lot in the private downtown Indian Harbor Association with 24-hour security. This gated community has many luxury waterfront homes in the district. The expansive lot has 1.9 acres in a 1/2 zone, allowing for a substantial home to be built. This lot is not subdividable. There is 290 feet of waterfront on Long Island Sound with its own pier and dock. The owners had

  Barbara Wells Houlihan Lawrence

  2 Vista Dr, Greenwich, CT 06830
• 

  

  /17

  $7,995,000

  • Land
  • 1.90 Acres
  • $4,207,895 per Acre

  2 Vista Dr, Greenwich, CT 06830

  Stunning waterfront building lot in the private downtown Indian Harbor Association with 24-hour security. This gated community has many luxury waterfront homes in the district. The expansive lot has 1.9 acres in a 1/2 zone, allowing for a substantial home to be built. This lot is not subdividable. There is 290 feet of waterfront on Long Island Sound with its own pier and dock. The owners had

  Barbara Wells Houlihan Lawrence

  2 Vista Dr, Greenwich, CT 06830
• 

  

  /19

  $2,799,000

  • 5 Beds
  • 5.5 Baths
  • 4,525 Sq Ft

  32 Jeffrey Rd, Greenwich, CT 06830

  A hidden gem close to town, updated and at the end of a cul-de-sac on a great quiet street, this beautiful 4,525-square-ft home on 1 acre offers a perfect blend of tranquility and convenience, located just minutes from town, the property boasts offices, 5 bedrooms, 5.5 baths, creating flexible layout, a perfect lifestyle for today's owner. Perfect for working from home or pursuing your passions.

  Lin Lavery Coldwell Banker Realty

  32 Jeffrey Rd, Greenwich, CT 06830

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