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Browse All Greenwich CT 5 Bedroom Properties for Sale

99 Porchuck Rd, Greenwich image
99 Porchuck Rd, Greenwich $3,000,000

Impeccably updated 5 bedroom colonial with a modern feel, convenient to town, yet private and quiet. Beautiful hardwood floors, 9 ft ceilings on the main level. Gourmet k...

  • 5 Beds
  • 5 Baths
  • 24206695 MLS
58 Halsey Dr, Greenwich image
58 Halsey Dr, Greenwich $4,674,000

Experience exceptional new construction by Build Casa Tua on Halsey Drive. Spanning four finished levels, this home blends timeless architecture with modern luxury. A dra...

  • 5 Beds
  • 7 Baths
  • 24206524 MLS
58 Shore Rd, Greenwich image
58 Shore Rd, Greenwich $19,995,000

You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineer...

  • 5 Beds
  • 7 Baths
  • 24164225 MLS
21 Calhoun Dr, Greenwich image
21 Calhoun Dr, Greenwich $6,150,000

A rare opportunity in one of Greenwich's most coveted in-town settings, 21 Calhoun Drive combines the timeless presence and character of a classic Greenwich estate with e...

  • 5 Beds
  • 8 Baths
  • 24205524 MLS
18 Shady Brook Ln, Greenwich image
18 Shady Brook Ln, Greenwich $3,450,000

Beautifully renovated by the current owners, this 5 bedroom, 5 bath home features refinished hardwood floors throughout, a modern open floor plan with eat-in kitchen/dini...

  • 5 Beds
  • 5 Baths
  • 24202309 MLS
61 Center Dr, Greenwich image
61 Center Dr, Greenwich $1,549,000

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home at the end of a cul de sac. Thoughtfully updated across two levels, this 5-bedroom, 3-full bath home offers...

  • 5 Beds
  • 3 Baths
  • 24200241 MLS
89 Indian Field Rd, Greenwich image
89 Indian Field Rd, Greenwich $3,495,000

Beautifully designed and thoughtfully finished, this exceptional New home blends sophisticated style with modern comfort and effortless everyday living. From the moment y...

  • 5 Beds
  • 5 Baths
  • 24201665 MLS
7 Bailiwick Rd, Greenwich image
7 Bailiwick Rd, Greenwich $4,250,000

Exceptional custom-built residence in Greenwich's coveted Bailiwick Association, thoughtfully designed with the finest materials, craftsmanship and an effortless connecti...

  • 5 Beds
  • 6 Baths
  • 24205146 MLS
739 Lake Ave, Greenwich image
739 Lake Ave, Greenwich $4,500,000

Your own private oasis in a prime Midcountry location. 739 Lake Avenue blends peaceful private living with easy access to downtown and all that Greenwich has to offer. Th...

  • 5 Beds
  • 6 Baths
  • 24204371 MLS
37 Mary Ln, Greenwich image
37 Mary Ln, Greenwich $2,999,000

Completely reimagined and expanded to nearly twice its original footprint, this exceptional Riverside residence is the result of a meticulous gut renovation by Abode Inte...

  • 5 Beds
  • 4 Baths
  • 24201047 MLS
74 Glenville Rd, Greenwich image
74 Glenville Rd, Greenwich $4,500,000

A Greenwich classic, this distinguished five-bedroom residence combines timeless architecture, exceptional craftsmanship, and grand-scale rooms designed for both entertai...

  • 5 Beds
  • 6 Baths
  • 24202628 MLS
42 Gerry St, Greenwich image
42 Gerry St, Greenwich $1,189,000

Welcome to 42 Gerry Street, a thoughtfully updated two-family property where the big-ticket improvements are already checked off the list, so you can spend more time enjo...

  • 5 Beds
  • 2 Baths
  • 24198916 MLS
203 Shore Rd, Greenwich image
203 Shore Rd, Greenwich $9,875,000

Hamptons-Inspired Elegance in Waterfront Lucas Point Experience the ease of coastal living just one hour from New York City in the coveted private waterfront association ...

  • 5 Beds
  • 6 Baths
  • 24196984 MLS
1 Hendrie Dr Extension, Greenwich image
1 Hendrie Dr Extension, Greenwich $3,300,000

A once-in-a-generation waterfront opportunity in Old Greenwich, perched above Greenwich Cove with breathtaking sunsets, expansive water views, and direct access to "The C...

  • 5 Beds
  • 3 Baths
  • 24194050 MLS
64 Hillside Rd, Greenwich image
64 Hillside Rd, Greenwich $7,495,000

Exceptional, new 2027 construction showcases an architecturally stunning in-town Colonial on .72 acres with pool, private yard and resort-style amenities close to world-c...

  • 5 Beds
  • 8 Baths
  • 24194488 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
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
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
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
991 Lake Ave, Greenwich image
991 Lake Ave, Greenwich $6,750,000

Some properties simply need to be experienced in person, and 991 Lake Avenue is one of them. Set on four beautifully landscaped and exceptionally private acres, this dist...

  • 5 Beds
  • 7 Baths
  • 24182061 MLS
4 Little Cove Ln, Greenwich image
4 Little Cove Ln, Greenwich $13,890,000 ▼

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree ...

  • 5 Beds
  • 7 Baths
  • 24172344 MLS
38 Partridge Hollow Rd, Greenwich image
38 Partridge Hollow Rd, Greenwich $6,995,000 ▼

Set on 8 private acres in one of Greenwich's most prestigious enclaves, 38 Partridge Hollow Road offers luxury and tranquility and the ultimate privacy. Boarded by protec...

  • 5 Beds
  • 8 Baths
  • 24164139 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.

5 Bedroom Greenwich Real Estate

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You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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Michael Parsell
Trusted Realty Partners
(203) 880-9675
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Trusted Realty Partners, LLC

324 Elm Street, Suite 105B

Monroe, CT 06468

Broker: John Fontana REB.0794755

(203) 880-9675
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