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All Greenwich Mid Country Houses For Sale

39 Brookridge Drive, Greenwich image
39 Brookridge Drive, Greenwich $28,500,000

Set along a quiet, serene in-town street, this exceptional 2027 new construction blends timeless architecture with modern livability. A striking white brick façade, steep...

  • 7 Beds
  • 12 Baths
  • 124682 MLS
16 Doubling Road, Greenwich image
16 Doubling Road, Greenwich $19,950,000 ▼

GREAT INVESTMENT OPPORTUNITY-Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2....

  • 9 Beds
  • 13 Baths
  • 124884 MLS
8 Fox Run Lane, Greenwich image
8 Fox Run Lane, Greenwich $19,950,000 ▼

Perfectly sited on a quiet lane minutes from Greenwich Avenue, this 2024 SBP home offers serenity on nearly 5.5 gated acres. Walls of glass flood the interiors with natur...

  • 8 Beds
  • 12 Baths
  • 124865 MLS
19 Khakum Drive, Greenwich image
19 Khakum Drive, Greenwich $17,995,000

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural ...

  • 7 Beds
  • 10 Baths
  • 124980 MLS
4 Rockwood Lane Spur, Greenwich image
4 Rockwood Lane Spur, Greenwich $15,000,000

Modern planning, superior craftsmanship and bespoke details define this extraordinary newly built Transitional home by visionary leaders Christopher Pagliaro Architects, ...

  • 6 Beds
  • 11 Baths
  • 125072 MLS
133 Doubling Road, Greenwich image
133 Doubling Road, Greenwich $14,750,000 ▲

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 traditiona...

  • 7 Beds
  • 9 Baths
  • 124281 MLS
164 Round Hill Road, Greenwich image
164 Round Hill Road, Greenwich $14,600,000 ▼

Unrivaled in its beauty, design, build and landscape, this unparalleled Mid-Country estate showcases an extensive 4 year restoration and renovation by leading industry vi...

  • 8 Beds
  • 14 Baths
  • 124477 MLS
137 Doubling Road Unit A, Greenwich image
137 Doubling Road Unit A, Greenwich $14,450,000

*Complete this Summer* Privately gated on 1.65 acres in Greenwich's coveted mid-country, this home blends timeless architecture by Alex Kaali-Nagy AIA with modern ele...

  • 6 Beds
  • 10 Baths
  • 125004 MLS
7 Loch Lane, Greenwich image
7 Loch Lane, Greenwich $13,495,000

Privately tucked away at the end of a tranquil lane in prestigious Mid-Country Greenwich, this custom built stone manor is a rare offering of timeless architecture, excep...

  • 6 Beds
  • 10 Baths
  • 125145 MLS
7 Parsonage Road, Greenwich image
7 Parsonage Road, Greenwich $13,100,000

SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, ...

  • 6 Beds
  • 8 Baths
  • 124868 MLS
524 Lake Avenue, Greenwich image
524 Lake Avenue, Greenwich $12,100,000

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 res...

  • 6 Beds
  • 13 Baths
  • 124826 MLS
31 Sawmill Lane, Greenwich image
31 Sawmill Lane, Greenwich $9,750,000

Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated ...

  • 6 Beds
  • 8 Baths
  • 125090 MLS
12 Woodside Road, Greenwich image
12 Woodside Road, Greenwich $9,350,000

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...

  • 6 Beds
  • 8 Baths
  • 125174 MLS
15 Vineyard Lane, Greenwich image
15 Vineyard Lane, Greenwich $8,880,000

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...

  • 6 Beds
  • 8 Baths
  • 124403 MLS
55 Calhoun Dr, Greenwich image
55 Calhoun Dr, Greenwich $8,795,000

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association....

  • 6 Beds
  • 10 Baths
  • 24177074 MLS
55 Calhoun Drive, Greenwich image
55 Calhoun Drive, Greenwich $8,795,000

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association....

  • 6 Beds
  • 10 Baths
  • 125058 MLS
174 Round Hill Road, Greenwich image
174 Round Hill Road, Greenwich $8,500,000

Set high on two exceptional acres in the coveted Golden Triangle, this custom-built home offers a great lifestyle just minutes from town and schools. The sun-filled six-b...

  • 6 Beds
  • 8 Baths
  • 125515 MLS
546 Lake Avenue, Greenwich image
546 Lake Avenue, Greenwich $7,995,000 ▼

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. S...

  • 6 Beds
  • 7 Baths
  • 124576 MLS
24 Stillman Ln, Greenwich image
24 Stillman Ln, Greenwich $7,599,000

Sport Lovers Dream - Set at end of a quiet cul-de-sac on Stillman Lane, this custom-built 2013 residence offers 4 finished levels of thoughtfully designed living space on...

  • 5 Beds
  • 9 Baths
  • 24191514 MLS
24 Stillman Lane, Greenwich image
24 Stillman Lane, Greenwich $7,599,000

Sport Lovers Dream - Set at end of a quiet cul-de-sac on Stillman Lane, this custom-built 2013 residence offers 4 finished levels of thoughtfully designed living space on...

  • 5 Beds
  • 9 Baths
  • 125424 MLS
64 Hillside Rd, Greenwich image
64 Hillside Rd, Greenwich $7,495,000

A rare opportunity to own a newly built 2027 residence just mins from Greenwich's finest shops, restaurants + schools. Set on .72 acres, 3 finished levels connected by el...

  • 5 Beds
  • 8 Baths
  • 24194488 MLS
736 Lake Avenue, Greenwich image
736 Lake Avenue, Greenwich $7,450,000

Timeless 1925 Colonial reimagined for modern living. Set on oversized, stunning 3.43 private acres in a coveted Mid-Country Greenwich location, this exceptional estate of...

  • 6 Beds
  • 7 Baths
  • 125248 MLS
74 Rock Maple Road, Greenwich image
74 Rock Maple Road, Greenwich $7,450,000 ▼

Set on four beautifully landscaped acres in Greenwich, 74 Rock Maple Road is a classic Georgian-style residence that blends timeless architecture with exceptional modern ...

  • 5 Beds
  • 9 Baths
  • 125052 MLS
21 Calhoun Drive, Greenwich image
21 Calhoun Drive, Greenwich $6,250,000 ▼

Welcome to Park Hill, a legacy property--reimagined for the way you live today. This 1923 English Manor tucked within a prestigious private association, offering the perf...

  • 5 Beds
  • 10 Baths
  • 122588 MLS
21 Pecksland Road, Greenwich image
21 Pecksland Road, Greenwich $5,850,000

One level living at its best! A gated drive introduces this beautifully appointed stone residence, gracefully set on over two exquisitely landscaped Mid-Country acres. Li...

  • 5 Beds
  • 6 Baths
  • 125265 MLS
135 & 129 Zaccheus Mead Lane, Greenwich image
135 & 129 Zaccheus Mead Lane, Greenwich $5,495,000 ▼

LOCATION ,LOCATION, LOCATION! Striking, sophisticated, & contemporary w/a true WOW factor. This exceptional residence is tucked within the celebrated Golden Triangle, sur...

  • 3 Beds
  • 5 Baths
  • 124681 MLS
583 Lake Avenue, Greenwich image
583 Lake Avenue, Greenwich $5,495,000

Exquisite 1942 washed brick colonial, in the highly coveted ''Golden Triangle'' abutting Rockwood Lane. Flanked by stone pillars and a circular drive set back from the ro...

  • 5 Beds
  • 7 Baths
  • 123963 MLS
20 Oak Street, Greenwich image
20 Oak Street, Greenwich $5,400,000

Set on a quiet private lane, this 8,600-square-foot residence spans four finished levels with elevator access throughout. A marble entry gallery with soaring ceilings int...

  • 5 Beds
  • 9 Baths
  • 125038 MLS
16 Annjim Dr, Greenwich image
16 Annjim Dr, Greenwich $5,250,000

An exceptional opportunity to own a thoughtfully crafted 2015 Colonial in one of Greenwich's most desirable in-town neighborhoods. Set on level grounds at the end of a qu...

  • 5 Beds
  • 6 Baths
  • 24191535 MLS
16 Annjim Drive, Greenwich image
16 Annjim Drive, Greenwich $5,250,000

An exceptional opportunity to own a thoughtfully crafted 2015 Colonial in one of Greenwich's most desirable in-town neighborhoods. Set on level grounds at the end of a qu...

  • 5 Beds
  • 6 Baths
  • 125397 MLS
121 Round Hill Road, Greenwich image
121 Round Hill Road, Greenwich $4,895,000 ▲

A Rare Convergence of Beauty, Vision and Readiness in Greenwich's Golden Triangle. This property is for a discerning buyer who values time and predictability. This 2.3-ac...

  • 6 Beds
  • 7 Baths
  • 122279 MLS
248 Stanwich Road, Greenwich image
248 Stanwich Road, Greenwich $4,500,000

Set on 1.21 acres, this beautifully maintained home has exceptional indoor and outdoor living designed for entertaining. Home was completely taken down to the studs in 20...

  • 3 Beds
  • 4 Baths
  • 125500 MLS
16 Ridgebrook Rd, Greenwich image
16 Ridgebrook Rd, Greenwich $4,495,000 ▼

Just minutes from downtown Greenwich, this beautifully renovated Colonial offers the ideal blend of luxury, comfort, and convenience. The bright, open interior features s...

  • 5 Beds
  • 6 Baths
  • 24188162 MLS
16 Ridgebrook Road, Greenwich image
16 Ridgebrook Road, Greenwich $4,495,000 ▼

Just minutes from downtown Greenwich, this beautifully renovated Colonial offers the ideal blend of luxury, comfort, and convenience. The bright, open interior features s...

  • 5 Beds
  • 6 Baths
  • 125396 MLS
108 Perkins Road, Greenwich image
108 Perkins Road, Greenwich $4,425,000

Welcome home to 108 Perkins Road. Set on over 2 private, beautifully landscaped acres in Midcountry, this classic Colonial offers the perfect blend of timeless elegance, ...

  • 4 Beds
  • 6 Baths
  • 125507 MLS
16 Vineyard Lane, Greenwich image
16 Vineyard Lane, Greenwich $4,250,000 ▼

Set on two picturesque acres in a premier Greenwich estate neighborhood, this exceptional property offers the perfect canvas to design and build your ultimate dream home....

  • 5 Beds
  • 6 Baths
  • 125144 MLS
34 Thunder Mountain Road, Greenwich image
34 Thunder Mountain Road, Greenwich $3,990,000 ▼

Welcome to 34 Thunder Mountain Rd - Set on a quiet cul-de-sac with easy access to Glenville, Central Greenwich and Westchester. Substantially re-built in 2024/2025 this m...

  • 5 Beds
  • 6 Baths
  • 125270 MLS
55 Will Merry Lane, Greenwich image
55 Will Merry Lane, Greenwich $3,595,000

Handsome brick Georgian just off Round Hill Road, renovated and expanded in 2010 with pool and spa, set on 2.41 landscaped and private acres. Custom built with exceptiona...

  • 5 Beds
  • 8 Baths
  • 125361 MLS
11 Butternut Hollow Rd, Greenwich image
11 Butternut Hollow Rd, Greenwich $3,495,000

Sun-filled Colonial set on 2 private acres with desirable east/west exposures, offering exceptional privacy and natural beauty. Thoughtfully updated throughout, the home ...

  • 5 Beds
  • 6 Baths
  • 24185738 MLS
11 Butternut Hollow Road, Greenwich image
11 Butternut Hollow Road, Greenwich $3,495,000 ▲

Private 2 acres in fabulous location! Discover this beautifully updated Colonial nestled on two private acres, offering exceptional privacy, picturesque grounds, and a p...

  • 5 Beds
  • 6 Baths
  • 125316 MLS
33 Hillside Road, Greenwich image
33 Hillside Road, Greenwich $3,250,000

A unique opportunity awaits the new owner to put their own footprint on this lovely 1911 home. This house is beautifully sited on 2.27 acres in one acre zoning and cannot...

  • 7 Beds
  • 5 Baths
  • 125092 MLS
219 Orchard Street, Cos Cob image
219 Orchard Street, Cos Cob $3,195,000

Nestled behind thoughtful & mature landscaping, 219 Orchard St is a beautifully crafted Colonial that combines timeless architecture with a floor plan of 5,442sf on 4 fin...

  • 6 Beds
  • 6 Baths
  • 125546 MLS
12 Bailiwick Road, Greenwich image
12 Bailiwick Road, Greenwich $3,095,000

Mesmerizing lakefront living in desirable Bailiwick Association. Extensively renovated, 3,843 sq.ft. light-filled, 4 Bedroom/4.5 bath contemporary home with open spaces, ...

  • 4 Beds
  • 5 Baths
  • 125076 MLS
46 Valleywood Rd, Greenwich image
46 Valleywood Rd, Greenwich $2,695,000

Inviting four-bedroom Tudor enjoys a beautiful, private backyard elevated by bluestone patio and lush, mature plantings on a desirable road near schools, shops and trains...

  • 4 Beds
  • 4 Baths
  • 24188511 MLS
46 Valleywood Road, Greenwich image
46 Valleywood Road, Greenwich $2,695,000

Inviting four-bedroom Tudor enjoys a beautiful, private backyard elevated by bluestone patio and lush, mature plantings on a desirable road near schools, shops and train...

  • 4 Beds
  • 4 Baths
  • 125410 MLS
73 Thunder Mountain Road, Greenwich image
73 Thunder Mountain Road, Greenwich $2,650,000

Charming center hall colonial at the end of a quiet mid country cul-de-sac. The location is convenient yet offers wonderful seclusion. Set on a park-like, level 2.3 acres...

  • 4 Beds
  • 4 Baths
  • 125114 MLS
51 Glen Road, Greenwich image
51 Glen Road, Greenwich $2,499,999 ▼

Close to town from this rare in-town Greenwich gem -- a corner lot home on a quiet cul-de-sac, just steps from Greenwich Avenue's shops, restaurants, and cafés, the Green...

  • 5 Beds
  • 4 Baths
  • 124257 MLS
65 Sherwood Pl Unit 65, Greenwich image
65 Sherwood Pl Unit 65, Greenwich $2,490,000

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 a...

  • 5 Beds
  • 6 Baths
  • 24188704 MLS
12 Sawmill Terrace, Greenwich image
12 Sawmill Terrace, Greenwich $2,149,000 ▼

Serene & Private Escape. With a trending modern sensibility, this light-filled residence showcases oversized windows and doors, and soaring ceilings throughout the home. ...

  • 3 Beds
  • 3 Baths
  • 124059 MLS
1 Putnam Hill Unit 3C, Greenwich image
1 Putnam Hill Unit 3C, Greenwich $780,000

Move right in! Downtown Greenwich Living at Its Finest Experience the perfect blend of serenity and convenience in this secure, private enclave set on a beautifully main...

  • 2 Beds
  • 2 Baths
  • 125126 MLS
386 North Street, Greenwich image
386 North Street, Greenwich $40,000

Experience the pinnacle of Mid-Country Greenwich living in this sprawling 10,000 sq ft estate, set on 2.3 manicured acres. Extensively updated in 2026, the residence blen...

  • 5 Beds
  • 9 Baths
  • 125394 MLS
83 Burning Tree Road, Greenwich image
83 Burning Tree Road, Greenwich $28,000 ▼

A unique blend of privacy, serenity, and endless lake activities. Welcome to Lakefront Living. Enjoy the tranquility of Frye Lake with stunning water views, a deck, and ...

  • 6 Beds
  • 5 Baths
  • 124581 MLS
30 Brookridge Drive, Greenwich image
30 Brookridge Drive, Greenwich $25,000

Live the ultimate Greenwich lifestyle in this private sanctuary set on 3.02 park-like acres, featuring grounds designed by the visionary behind the Brooklyn Botanical Gar...

  • 4 Beds
  • 6 Baths
  • 125321 MLS
25 Will Merry Lane, Greenwich image
25 Will Merry Lane, Greenwich $23,000 ▼

Fabulous single family estate with gorgeous pool. Stylish six-bedroom Colonial set back on two Mid-Country acres. Private backyard retreat with heated pool, stone terrace...

  • 6 Beds
  • 7 Baths
  • 125227 MLS
9 Park Place, Greenwich image
9 Park Place, Greenwich $22,500 ▼

Spend the summer in this stylishly remodeled & fully furnished/equipped home situated on the most beautiful street in downtown Greenwich. This timeless & handsome Colonia...

  • 4 Beds
  • 5 Baths
  • 125133 MLS
546 Lake Avenue, Greenwich image
546 Lake Avenue, Greenwich $20,000

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 - ...

  • 6 Beds
  • 6 Baths
  • 125567 MLS
42 Oak Street, Greenwich image
42 Oak Street, Greenwich $15,000

Fabulous rental opportunity in Greenwich, offering a private and peaceful setting just minutes from town, the train station, top-rated schools, shopping, and dining. Impe...

  • 5 Beds
  • 3 Baths
  • 125577 MLS
63 Church Street Unit 1, Greenwich image
63 Church Street Unit 1, Greenwich $15,000

Welcome to The Madrid at The Five Greenwich. Presented by Corner North Ventures & designed by Fofie & Mia's, this designer-furnished luxury townhome blends modern Europea...

  • 2 Beds
  • 3 Baths
  • 125481 MLS
23 Copper Beech Road, Greenwich image
23 Copper Beech Road, Greenwich $12,500

Wonderful opportunity to rent in the heart of Mid-Country. Ideally located on a beautiful street with convenient access to public and private schools, downtown Greenwich,...

  • 4 Beds
  • 4 Baths
  • 125479 MLS
88 Orchard Street, Cos Cob image
88 Orchard Street, Cos Cob $12,500

Located in a sought-after Cos Cob neighborhood, this spacious and sun-filled home offers approximately 3,800 square feet of finished living space across three levels. Des...

  • 5 Beds
  • 4 Baths
  • 125290 MLS
46 Valleywood Road, Greenwich image
46 Valleywood Road, Greenwich $12,250

Wonderful opportunity to rent a furnished or unfurnished, updated four-bedroom Tudor with bluestone patio and beautiful, private backyard on a desirable road near school...

  • 4 Beds
  • 4 Baths
  • 125411 MLS
18 Cornelia Drive, Greenwich image
18 Cornelia Drive, Greenwich $12,250

Located on a quiet mid country lane in the North Street school district, this center hall colonial offers privacy and tranquility with views of the one and a half acre pr...

  • 4 Beds
  • 4 Baths
  • 125264 MLS
20 Church Street Unit A24, Greenwich image
20 Church Street Unit A24, Greenwich $10,500 ▼

Welcome to this Manhattan style 3 bedroom 2 bathroom apartment in Downtown Greenwich. As you go inside, you'll notice the beautiful hardwood flooring and custom millwork....

  • 3 Beds
  • 2 Baths
  • 125190 MLS
63 Church Street Unit 3, Greenwich image
63 Church Street Unit 3, Greenwich $10,000

Welcome to The Tokyo at The Five Greenwich. Presented by Corner North Ventures & designed by Fofie & Mia's, this fully furnished luxury residence delivers a rare downtown...

  • 1 Beds
  • 2 Baths
  • 125561 MLS
63 Church Street Unit 5, Greenwich image
63 Church Street Unit 5, Greenwich $10,000

Welcome to The Capri at The Five Greenwich. Presented by Corner North Ventures & designed by Fofie & Mia's, this fully furnished luxury residence blends sophisticated con...

  • 1 Beds
  • 2 Baths
  • 125108 MLS
63 Church Street Unit 4, Greenwich image
63 Church Street Unit 4, Greenwich $9,000

Welcome to The Paris at The Five Greenwich. Presented by Corner North Ventures & designed by Fofie & Mia's, this fully furnished luxury residence delivers a rare downtown...

  • 1 Beds
  • 2 Baths
  • 125559 MLS
147 Holly Hill Lane Unit 10, Greenwich image
147 Holly Hill Lane Unit 10, Greenwich $8,500 ▼

One of ten residences in a private, professionally managed enclave, this beautifully updated luxury townhome delivers the space and serenity of single-family living with ...

  • 2 Beds
  • 3 Baths
  • 125308 MLS
63 Church Street Unit 2, Greenwich image
63 Church Street Unit 2, Greenwich $8,000

Welcome to The Monaco at The Five Greenwich. Presented by Corner North Ventures & designed by Fofie & Mia's, this fully furnished luxury residence delivers a rare downtow...

  • 1 Beds
  • 2 Baths
  • 125562 MLS
14 Grove Lane, Greenwich image
14 Grove Lane, Greenwich $6,250

CHARMING HOME LOCATED IN AN IN-TOWN ESTATE AREA. 3BR/2BATH WITH 1 CAR GARAGE. VERY PRIVATE YET CLOSE TO DOWNTOWN, TRANSPORTATION, LIBRARY, SHOPS AND RESTAURANTS. FIRST FL...

  • 3 Beds
  • 2 Baths
  • 125544 MLS
47 Church Street Unit 1, Greenwich image
47 Church Street Unit 1, Greenwich $3,950

Experience the perfect blend of suburban charm and urban convenience. This bright and airy 2-bedroom, 1-bathroom first-floor residence offers an unmatched lifestyle in do...

  • 2 Beds
  • 1 Baths
  • 125517 MLS
243 Glenville Road Unit 2nd Floor, Greenwich image
243 Glenville Road Unit 2nd Floor, Greenwich $2,400

Sun pours into this adorable one bedroom, with all utilities included! Close to shopping, restaurants, schools, park & beaches...just in time for Summer! Cats OK, sorry n...

  • 1 Beds
  • 1 Baths
  • 125391 MLS

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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