Old Greenwich, CT Homes for Sale with Acreage

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  /27

  $1,100,000

  • 4 Beds
  • 3 Baths
  • 3,368 Sq Ft

  1238 Westover Rd, Stamford, CT 06902

  After 40 years, this gracious split-level ranch on over two private acres is ready for its next chapter. With a versatile floor plan that lives like a five-bedroom home plus office, it offers exceptional flexibility for empty nesters seeking a main-level primary suite or families in need of generous space. The expansive living room, anchored by a brick wood-burning fireplace, flows into the

  

  Suzette Kraus

  Compass Connecticut, LLC

  (475) 260-0735

  1238 Westover Rd, Stamford, CT 06902
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  /31

  $8,880,000

  • 6 Beds
  • 8 Baths
  • 7,718 Sq Ft

  15 Vineyard Ln, Greenwich, CT 06831

  Location, location, location! This stunning stone colonial sits on 2 park like acres just minutes from downtown Greenwich. With over 9,000 sq ft of beautiful living space, this 6-bedroom, 6.5-bath home offers graciously scaled rooms and an exceptional floor plan. The luxurious primary suite features a fireplace, dual bathrooms, and walk-in closets. Enjoy the spacious playroom over the garage, a

  

  Megan Sullivan

  Douglas Elliman of Connecticut

  (475) 265-6175

  15 Vineyard Ln, Greenwich, CT 06831
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  /29

  $6,000,000

  • 6 Beds
  • 8 Baths
  • 6,998 Sq Ft

  9 Frost Rd, Greenwich, CT 06830

  Exquisitely renovated Cotswold-style manor on a private road, blending timeless charm with modern elegance. Set on two serene, landscaped acres overlooking Horseneck Brook, this home offers tranquility and understated sophistication. A gourmet kitchen anchors the home with high-end finishes and seamless flow for everyday living and entertaining. French doors from the living, dining, and kitchen

  

  Linna Yuen

  Coldwell Banker Realty

  (475) 252-8941

  9 Frost Rd, Greenwich, CT 06830
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  /29

  $2,450,000

  • 4 Beds
  • 4.5 Baths
  • 4,161 Sq Ft

  150 N Old Stone Bridge Rd, Greenwich, CT 06807

  Nestled at 150 N Old Stone Bridge Road in Cos Cob, this charming home seamlessly blends classic elegance with modern updates. Surrounded by mature trees and lush landscaping, it offers a peaceful retreat minutes from downtown Greenwich and train station. Inside, enjoy sunlit living spaces, a beautifully updated kitchen with high-end appliances, and a cozy fireplace in the living room. The primary

  Cesar Rabellino Compass Connecticut, LLC

  150 N Old Stone Bridge Rd, Greenwich, CT 06807
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  /13

  $727,350 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths

  142 Putnam Park, Greenwich, CT 06830

  Bright south-facing corner unit bathed in natural light, featuring three spacious bedrooms and two full bathrooms. Enjoy stunning treetop views of a magnificent blooming magnolia right outside the living room windows. This desirable second-floor home offers a private balcony overlooking the peaceful courtyard, beautiful hardwood floors throughout, and effortless access to all that downtown has to

  Christopher Triano Houlihan Lawrence

  142 Putnam Park, Greenwich, CT 06830
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  /25

  $10,995,000

  • 6 Beds
  • 11 Baths
  • 13,318 Sq Ft

  167 Zaccheus Mead Ln, Greenwich, CT 06831

  Azalea Hill is a stunning classic estate set on nearly four acres of beautifully manicured grounds. Thoughtfully reimagined, it blends timeless charm with a fresh, modern feel. Sunlit interiors showcase soaring ceilings, five fireplaces, herringbone floors, and French doors opening to terraces and vibrant azalea gardens. An infinity-edge pool and spa overlook the picturesque landscape. The chef's

  Joanne Mancuso Houlihan Lawrence

  167 Zaccheus Mead Ln, Greenwich, CT 06831
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  /73

  $5,850,000

  • 7 Beds
  • 6.5 Baths
  • 5,109 Sq Ft

  175 Cat Rock Rd, Cos Cob, CT 06807

  This picturesque farmhouse sits on 2.6 acres of landscaping with an expansive lawn & antique stone walls. The original home was totally renovated with the highest quality by a renowned architect. The spacious light filled home has generous sized rooms w/ a total of 5 fireplaces & radiant heated wide oak floors on the main level. Every room on the main floor also offers access to the beautiful

  Roseann Benedict Compass Connecticut, LLC

  175 Cat Rock Rd, Cos Cob, CT 06807
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  /26

  $5,800,000

  • 5 Beds
  • 3.5 Baths
  • 4,324 Sq Ft

  8 Indian Point Ln, Riverside, CT 06878

  Tucked within the secluded Indian Point Association, this 1.55-acre waterfront sanctuary in coveted Riverside invites you to imagine the lifestyle that you have always wanted. From its sweeping southwestern vantage point, the property opens to mesmerizing views of Long Island Sound-a living canvas that shifts with every season, every tide, every change of light. A charming 1949 built house sits

  Patte Nusbaum Sotheby's International Realty

  8 Indian Point Ln, Riverside, CT 06878
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  /40

  $1,550,000

  • 4 Beds
  • 3.5 Baths
  • 4,637 Sq Ft

  1038 Westover Rd, Stamford, CT 06902

  Nestled in the heart of Stamford, Connecticut, at 1038 Westover Road, this contemporary colonial home offers 4,262 square feet of thoughtfully designed living space. With four spacious bedrooms and three and a half elegant bathrooms, plus a large family room, this home blends classic charm with modern convenience. An expansive, sun-filled family room and open-concept kitchen are perfect for both

  Juan Garcia Sunbelt Sales & Development

  1038 Westover Rd, 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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  /22

  $5,395,000

  • 5 Beds
  • 7 Baths
  • 5,446 Sq Ft

  3 Konittekock Rd, Greenwich, CT 06831

  Set on a quiet cul-de-sac in the prestigious Khakum Wood Association, this exquisitely renovated, sun-filled home offers elegant lakefront living. The kitchen opens to a spacious family room with fireplace, while a sunroom with wet bar overlooks the lake and private island. Additional highlights include a paneled living room with fireplace, dining room with built-ins, and an office. The luxurious

  Joseph Barbieri Sotheby's International Realty

  3 Konittekock Rd, Greenwich, CT 06831
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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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  /33

  $11,500,000

  • 6 Beds
  • 7 Baths
  • 8,081 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
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  /43

  $6,345,000

  • 5 Beds
  • 5.5 Baths
  • 6,233 Sq Ft

  164 Stanwich Rd, Greenwich, CT 06830

  Welcome to this exquisitely updated Colonial on 1.16 landscaped acres near Greenwich Country Club and minutes from town. A grand foyer with gleaming hardwood floors and sweeping staircase introduces the elegant interior. The main level includes a formal living room, dining room, two studies, and a gourmet kitchen with Wolf appliances, Palissandro marble, Thermador coffee station, a custom wet bar

  Jeffrey Jackson Corcoran Centric Realty LLC

  164 Stanwich Rd, Greenwich, CT 06830
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  /21

  $19,000,000

  • 6 Beds
  • 9 Baths
  • 9,565 Sq Ft

  25 Field Point Cir, Greenwich, CT 06830

  FIELD POINT CIRCLE: Grandly proportioned French-inspired manor set within the prestigious 24-hour guard-gated private Association. Sited on 2.2 level parklike acres, this limestone-clad residence with a 2014 new slate roof offers exceptional privacy for outdoor living, featuring a pool and spa. The elegant six-bedroom residence, with 7 full and two half bathrooms, is distinguished by a flexible

  Leslie McElwreath Sotheby's International Realty

  25 Field Point Cir, Greenwich, CT 06830
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  /35

  $15,995,000

  • 6 Beds
  • 8 Baths
  • 8,962 Sq Ft

  44 Khakum Wood Rd, Greenwich, CT 06831

  Located in Khakum Wood Association, a premier Greenwich location. The extensive 3 year expansion & renovation completed in 2025 is the collaboration of Top 100 Architectural Digest designers and architects: McAlpine House,Studio Mellone, Mario Neivera,with construction by the Tallman Builders.Reimagined for today's living.Pool, Carriage house with apartment, gym, Savant smart house, gardens and

  Robin Kencel Compass Connecticut, LLC

  44 Khakum Wood Rd, Greenwich, CT 06831
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  /18

  $7,450,000

  • 4 Beds
  • 5.5 Baths
  • 5,140 Sq Ft

  47 Husted Ln, Greenwich, CT 06830

  Elegant Regency style single-level living in a fabulous Greenwich location. This beautifully designed four-bedroom, five-and-one-half bath Home offers approximately 5,100 square feet of sun-filled living space with refined finishes and gracious proportions throughout. Expansive living and entertaining rooms, a stunning dining room, and a beautifully appointed kitchen create an effortless flow for

  Salley Maloney Houlihan Lawrence

  47 Husted Ln, Greenwich, CT 06830
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  /40

  $2,195,000

  • 4 Beds
  • 5.5 Baths
  • 7,500 Sq Ft

  14 Windermere Ln, Stamford, CT 06902

  14 Windermere Lane - Elegance and modern comfort converge in this comprehensively renovated 6-bedroom, 5.5-bath residence, where every detail has been thoughtfully curated. A full-home renovation includes beautifully updated bathrooms throughout and a stunning open-concept kitchen designed for both effortless daily living and refined entertaining. The home also offers the convenience and

  Ryan Dichter Compass Connecticut, LLC

  14 Windermere Ln, Stamford, CT 06902
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  /31

  $6,495,000

  • 5 Beds
  • 9 Baths
  • 13,474 Sq Ft

  386 North St, Greenwich, CT 06830

  This magnificent 9,974 sq ft estate seamlessly blends grand scale, craftsmanship, and modern luxury following an extensive 2025-2026 renovation. Set on 2.3 parklike acres in coveted Mid-Country Greenwich, just minutes from town, the home makes an immediate impression with a soaring two-story foyer introducing exquisitely appointed interiors defined by custom details and rich materials. Completed

  Jennifer Leahy Compass Connecticut, LLC

  386 North St, Greenwich, CT 06830
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  /30

  $4,995,000

  • 4 Beds
  • 3.5 Baths
  • 6,915 Sq Ft

  177 Indian Head Rd, Riverside, CT 06878

  One of Riverside's most coveted waterfront enclaves, this elegant colonial offers refined living with a sense of privacy and tranquility set on nearly 2 acres. A new cedar just completed in 2025. The first level features a living room with fireplace, expansive family room, formal dining room, and sunny gallery passageway with French doors. Access the secluded back patio from the open kitchen,

  Remy Cook Corcoran Centric Realty LLC

  177 Indian Head Rd, Riverside, CT 06878
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  /28

  $2,375,000

  • 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
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  /40

  $15,945,000

  • 6 Beds
  • 10 Baths
  • 11,211 Sq Ft

  30 Meadowcroft Ln, Greenwich, CT 06830

  Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold

  Jeffrey Jackson Corcoran Centric Realty

  30 Meadowcroft Ln, Greenwich, CT 06830
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  /26

  $960,000

  • 2 Beds
  • 2 Baths
  • 1,263 Sq Ft

  1215 Westover Rd, Stamford, CT 06902

  Private three bedroom country cottage in the sought-after Westover neighborhood, re-built from the studs in 1992, set on a level property with exceptional privacy and mature landscaping. This bright, open-concept home features a welcoming foyer, spacious living and dining areas with large windows overlooking the garden and a white kitchen with stainless steel appliances. The primary bedroom

  Catherine Aaron Berkshire Hathaway NE Prop.

  1215 Westover Rd, Stamford, CT 06902
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  /40

  $1,990,000

  • 5 Beds
  • 4.5 Baths
  • 4,665 Sq Ft

  1209 Westover Rd, Stamford, CT 06902

  Extraordinary opportunity. A gracious country estate in the highly sought-after Westover neighborhood, set on a stately and private property with mature gardens, in-ground pool, fountain and large patio ideal for outdoor entertaining. This custom built 5-bedroom, 5-bath home blends classic architecture with subtle European designer influences throughout. Meticulous care devoted to upgrade this

  Catherine Aaron Berkshire Hathaway NE Prop.

  1209 Westover Rd, Stamford, CT 06902
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  /24

  $2,050,000

  • 4 Beds
  • 2.5 Baths
  • 2,171 Sq Ft

  189 Riversville Rd, Greenwich, CT 06831

  Charming home once part of a majestic Greenwich estate is set on 2.03 picturesque acres framed by classic stone walls. Thoughtfully updated while preserving its timeless charm and intimate scale, the farmhouse-style home blends character with modern comfort. Sun-filled interiors feature hardwood floors throughout, an updated kitchen that opens seamlessly to the family room & dining area, ideal

  Maria Crowley Houlihan Lawrence

  189 Riversville Rd, Greenwich, CT 06831
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  /37

  $24,900,000

  • 7 Beds
  • 8 Baths
  • 18,217 Sq Ft

  44 & 40 Mayo Ave, Greenwich, CT 06830

  Nestled within the prestigious Belle Haven, Fairholme Estate is a magnificent English Manor that exudes timeless elegance and grandeur. Set on 2.74 beautifully landscaped acres, this seven-bedroom masterpiece features a spectacular pool, gracious wraparound porch, formal gardens, and expansive lawns, complemented by a charming coachman's cottage. Meticulously preserved to honor its historic

  Joanne Mancuso Houlihan Lawrence

  44 & 40 Mayo Ave, Greenwich, CT 06830
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  /20

  $21,000,000

  • 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 of

  James Hoffman Houlihan Lawrence

  8 Fox Run Ln, Greenwich, CT 06831
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  /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
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  /31

  $3,120,000

  • 3 Beds
  • 3.5 Baths
  • 3,512 Sq Ft

  403 Stanwich Rd, Greenwich, CT 06830

  Come see this total and complete renovation!. New design, expanded Sq ft, custom hand built kitchen, all new mechanicals, roof, siding, windows, baths, etc. New granite pool deck, private 1.23 acres on desirable Stanwich rd. location.

  Stephen Kane Sotheby's International Realty

  403 Stanwich Rd, Greenwich, CT 06830
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  /27

  $12,495,000

  • 6 Beds
  • 11 Baths
  • 10,421 Sq Ft

  537 North St, Greenwich, CT 06830

  Exquisite six-bedroom stone manor, executed to the highest standards, and sited atop a majestic knoll on 2.97 picturesque acres in the heart of Mid-Country Greenwich. Chic, sophisticated interiors by Amy Hirsch unfold across three levels of light-filled living space, highlighted by soaring ceilings, oversized custom windows, and every modern amenity. An elegant double-height entry hall with

  Leslie McElwreath Sotheby's International Realty

  537 North St, Greenwich, CT 06830
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  /34

  $8,250,000

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

  34 Dublin Hill Dr, 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 Dr, Greenwich, CT 06830
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  /40

  $2,475,000

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

  681 River Rd, Cos Cob, CT 06807

  Chalet d'Amour You've never seen a house like this. An architecturally crafted contemporary on 2.32 private acres. Soaring vaulted ceilings, two stone fireplaces, walls of glass, and light that pours in from every angle. First floor primary suite with cathedral ceiling, dual baths, dual walk-in closets and a grand whirlpool tub beneath peaked windows. Three more bedrooms up, all en suite, one

  Paula Waldman Berkshire Hathaway NE Prop.

  681 River Rd, Cos Cob, CT 06807
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  /23

  $10,350,000

  • 5 Beds
  • 4 Baths
  • 8,223 Sq Ft

  111 Byram Shore Rd, Greenwich, CT 06830

  Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage

  Joseph Barbieri Sotheby's International Realty

  111 Byram Shore Rd, Greenwich, CT 06830
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  /28

  $2,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  12 Sawmill Terrace, Greenwich, CT 06830

  Tucked away down a quiet mid-country lane, surrounded by pretty woodlands, is this modern styled one level home with 3 bedroom septic. Large open reception hall, large living room with fireplace, high ceilings, study/office area, and large formal south-facing dining room with oversized windows that overlook the front yard and lovely mature trees. A step down from the dining room through French

  Edward Mortimer Sotheby's International Realty

  12 Sawmill Terrace, Greenwich, CT 06830
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  /47

  $3,499,000 Open Sun 1PM - 3PM

  • 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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  /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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  /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

  $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
• 

  

  /44

  $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
• 

  

  /47

  $6,395,000 Open Sun 1PM - 3PM

  • 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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