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5-Bedroom Homes for Rent in Old Greenwich, CT

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  • /27

    $6,750 per month

    • 5 Beds
    • 3.5 Baths
    • 4,776 Sq Ft
    • House for Rent

    208 Guinea Rd, Stamford, CT 06903

    Pristine and spacious 5-bedroom Colonial for rent near the Greenwich border, perfect for both everyday living and entertaining. Recently renovated throughout with fresh interior/exterior paint, brand new bathrooms, updated flooring, kitchen improvements, and electrical upgrades. The classic center hall layout includes a formal dining room, a living room with a fireplace, and a large eat-in

    Agent Photo

    Laura Danforth

    William Raveis Real Estate

    (203) 801-8001

    208 Guinea Rd, Stamford, CT 06903
  • /17

    $20,000 per month

    • 5 Beds
    • 3 Baths
    • 3,517 Sq Ft
    • House for Rent

    22 Tomac Ave, Old Greenwich, CT 06870

    End of summer into Fall furnished rental at $5,000 pre WEEK. Convenient location for easy access to Old Greenwich south of the village w/sidewalks to town, school & train. This spacious Shore Colonial is warm & welcoming with 5 bedrooms and 3 full baths. Easy access to nearby Tomac Cove for fishing. The home has a large LL game room for hours of fun, opens to yard. Living room has a

    Jackie Hammock Coldwell Banker Realty

    22 Tomac Ave, Old Greenwich, CT 06870
  • /35

    $32,000 per month

    • 5 Beds
    • 5.5 Baths
    • 4,300 Sq Ft
    • House for Rent

    20 Sound Beach Ave, Greenwich, CT 06870

    NEW BUILD in coveted Old Greenwich, close to BEACH! Greeted with Wide Plank White Oak hardwood floors and high end finishes throughout the home, it truly is a masterpiece. Open-concept Kitchen is full of gold accent fixtures and JennAir appliances, with a large waterfall Quartz Carrara Gold Island. Entertain your guests while admiring the electric heating fireplace in the living room which also

    Kaltrina Xhema-Latifi Higgins Group Greenwich

    20 Sound Beach Ave, Greenwich, CT 06870
  • /35

    $18,000 per month

    • 6 Beds
    • 9.5 Baths
    • 11,648 Sq Ft
    • House for Rent

    229 Stanwich Rd, Greenwich, CT 06830

    Timeless Grandeur Meets Modern Luxury in Greenwich. Welcome to an extraordinary estate that redefines elegant living. Perfectly sited on over five acres in prestigious Greenwich, this elegant Center Hall Colonial offers the ultimate in privacy and sophistication. With six spacious bedrooms, twelve beautifully appointed bathrooms, this expansive residence seamlessly blends classic architectural

    Patricia Hinkley Coldwell Banker Katonah

    229 Stanwich Rd, Greenwich, CT 06830
  • /50

    $7,850 per month

    • 5 Beds
    • 2.5 Baths
    • 4,928 Sq Ft
    • Condo for Rent

    92 Valley Rd Unit A, Cos Cob, CT 06807

    FULLY FURNISHED 5 BEDROOM AND 2.5 BATHROM end townhouse-style unit with a private spacious patio (feels more like a single-family home than a townhouse). All new furniture and Picasso-style decor. This spacious townhouse is updated all over: new kitchen, new appliances, new floors, new bathrooms. Every decoration item has been hand-picked to match the style. The house is a close distance to

    Victoria Tashash Higgins Group Greenwich

    92 Valley Rd Unit A, Cos Cob, CT 06807
  • /35

    $12,000 per month

    • 5 Beds
    • 3.5 Baths
    • 3,634 Sq Ft
    • House for Rent

    551 River Rd, Cos Cob, CT 06807

    Bathed in natural light, this 5-bedroom, 3.5-bath Center Hall Colonial blends classic design with modern comfort. Conveniently located in the sought-after North Mianus Elementary and Eastern Middle School districts, with the elementary school just down the block. A dramatic two-story foyer opens to formal living and dining rooms. The chef's kitchen with casual dining flows to a spacious family

    Rachel Overton Berkshire Hathaway HS NE Prop.

    551 River Rd, Cos Cob, CT 06807
  • /19

    $15,500 per month

    • 5 Beds
    • 3.5 Baths
    • House for Rent

    34 Park Ave, Old Greenwich, CT 06870

    In the heart of Old Greenwich with close proximity to the village, schools and train, this charming rental property is available for occupancy on October 15th for long term. 2019 renovations inside and out with bonus garage apartment perfect for visiting guests, staff, gym or separate home office. Great private back yard and shaded deck.

    Robert Johnson Brown Harris Stevens CT, LLC

    34 Park Ave, Old Greenwich, CT 06870
  • /40

    $6,000 per month

    • 6 Beds
    • 4 Baths
    • 2,924 Sq Ft
    • House for Rent

    34 Hundley Ct, Stamford, CT 06902

    Stunning Newly Remodeled Glenbrook neighborhood home with Finished Walkout Basement~Family Room, Home Office Room, New Full Bath; 1st Fl~Open Concept Large Eat-In Kitchen, Living Room, Bedroom#4, Bedroom#5, New Full Bath; 2nd Fl~ 3 Bedrooms, New Full Bath, Laundry Area; 3rd Fl~ Den/ Bedroom#6, New Full Bath (independent access from side staircase). Garage with new remote door and additional

    Irene Cheung BHGRE Shore & Country

    34 Hundley Ct, Stamford, CT 06902
  • /37

    $15,000 per month

    • 5 Beds
    • 5.5 Baths
    • 5,676 Sq Ft
    • House for Rent

    31 Vineyard Ln, Greenwich, CT 06831

    Immediate rental opportunity! Secluded five-bedroom Contemporary boasts recent updates with walls of windows, inviting decks overlooking Horseneck Brook, elevator, indoor pool on two lush acres. Set back off a convenient lane close to town. Features upgraded eat-in kitchen with new floors, Quartz-clad counters, appliances; freshly painted interior and new mudroom. Main floor showcases fireplaces

    Spencer Sodokoff Houlihan Lawrence

    31 Vineyard Ln, Greenwich, CT 06831
  • /36

    $10,000 per month

    • 6 Beds
    • 5.5 Baths
    • 3,266 Sq Ft
    • House for Rent

    254 West Ave, Darien, CT 06820

    Located in the highly sought-after Noroton Heights neighborhood of Darien, this move-in-ready 6 bedroom with 5.5 bath residence offers the perfect blend of convenience and flexibility. Just steps from the vibrant new Darien Commons, residents will enjoy easy access to shopping, dining, school, health club, Metro-North for commuters & major highways, making this an ideal location for today's

    AnneMarie Rayhill Houlihan Lawrence

    254 West Ave, Darien, CT 06820
  • /25

    $15,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,378 Sq Ft
    • House for Rent

    23 Oak St, Greenwich, CT 06831

    Newly refreshed home, close to Town. Covered indoor pool, large usable yard.Primary bedroom includes a large sitting room with a fireplace, private office and luxurious bath.

    Michele Klosson Sotheby's International Realty

    23 Oak St, Greenwich, CT 06831
  • /17

    $17,500 per month

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    420 Davis Ave, Greenwich, CT 06830

    Location and Charm with serene tidal views of sea grass and winged wildlife make this spacious Central Greenwich home a nature lover's paradise. There is a private dock to launch your kyack. Across from scenic Bruce Park with paths, tennis, playing fields & bocce. Deeded walking access to ''Mead Point Beach'' in a private gated association. Renovations include new kitchen, baths, windows, Hvac

    Marjorie Marianacci Coldwell Banker Realty

    420 Davis Ave, Greenwich, CT 06830
  • /29

    $16,500 per month

    • 5 Beds
    • 5 Baths
    • 3,994 Sq Ft
    • House for Rent

    39 Indian Mill Rd, Cos Cob, CT 06807

    AVAILABLE IMMEDIATELY. Situated on a quiet lane in North Street School District, with a path to North Mianus Park at end of cul-de-sac. Sun-filled five-bedroom Colonial, with a heated pool, is thoughtfully designed with an open floor plan seamlessly connecting indoor and outdoor living. The main level offers a mix of formal and informal spaces, including a bright kitchen with breakfast nook,

    Ellen Mosher Houlihan Lawrence

    39 Indian Mill Rd, Cos Cob, CT 06807
  • /45

    $15,500 per month

    • 5 Beds
    • 3.5 Baths
    • 3,339 Sq Ft
    • House for Rent

    92 Hillcrest Park Rd, Old Greenwich, CT 06870

    This charming Colonial home in Hillcrest Park is nestled on a one-acre property beautifully blends elegance and comfort. Features 5 spacious bedrooms and 3.5 baths. Chef's kitchen is equipped with high-end appliances and an inviting eat-in area bathed in sunlight. French doors open to a serene patio and garden, creating a seamless indoor-outdoor living experience. Adjacent to the kitchen are a

    Dee Darce William Raveis Real Estate

    92 Hillcrest Park Rd, Old Greenwich, CT 06870
  • /80

    $75,000 per month

    • 6 Beds
    • 6.5 Baths
    • House for Rent

    546 Lake Ave, Greenwich, CT 06830

    'Chateau Chadeline' an architectural landmark blending classic charm and modern refinement is located in the heart of mid country on Lake Avenue. This stunning complete renovation has 6 ensuite bedrooms, 2 saunas, and is nestled in 2.83 park- like acres. An over sized pool, tennis court, 2 bedroom guest cottage complete this spectacular home boasting spa like amenities. Sited above Horseneck

    Mary Jones Sotheby's International Realty

    546 Lake Ave, Greenwich, CT 06830
  • /43

    $45,000 per month

    • 6 Beds
    • 8 Baths
    • 10,328 Sq Ft
    • House for Rent

    31 Sawmill Ln, Greenwich, CT 06830

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

    Kevin Sneddon Compass Connecticut, LLC

    31 Sawmill Ln, Greenwich, CT 06830
  • /45

    $22,000 per month

    • 7 Beds
    • 8 Baths
    • 7,148 Sq Ft
    • House for Rent

    190 Lake Ave, Greenwich, CT 06830

    Stylish & cozy, sunlit flooded fully furnished flexible term rental. Tenants need only to bring personal belongings. Enter through a private courtyard. Main house 1st floor rooms all open from the foyer: living room with French doors to terrace. Dining room 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
  • /37

    $8,900 per month

    • 6 Beds
    • 5 Baths
    • 2,950 Sq Ft
    • House for Rent

    53 Indian Field Rd, Greenwich, CT 06830

    Classic Colonial Living in Central Greenwich - 6 Beds, 5 Baths, Walk to Town! Discover timeless elegance and unbeatable convenience in this sun-drenched 6-bedroom, 5-bath Colonial located in the heart of Central Greenwich. Just moments from downtown shops, schools, and easy access to major highways, and Metro-North Train, this beautiful home offers both comfort and location. Step inside to find

    Hannah Driscoll Berkshire Hathaway NE Prop.

    53 Indian Field Rd, Greenwich, CT 06830
  • /16

    $11,650 per month

    • 5 Beds
    • 3 Baths
    • 2,889 Sq Ft
    • House for Rent

    41 Meyer Place, Riverside, CT 06878

    Welcome to this beautifully renovated 5-bedroom, 3-bathroom home in the heart of Riverside, one of the town's most desirable neighborhoods! Fully updated in 2025.Situated on a quiet cul-de-sac and just minutes from the Riverside train station, highly rated Riverside Elementary and Eastern Middle Schools, shops, dining, and Tod's point. Everything you may need is just a short distance

    Lisa Castellana BHGRE Shore & Country Properties

    41 Meyer Place, Riverside, CT 06878
  • /54

    $23,000 per month

    • 5 Beds
    • 5.5 Baths
    • 4,553 Sq Ft
    • House for Rent

    127 Dingletown Rd, Greenwich, CT 06830

    Mid-Country Classic Colonial nestled in a park-like setting sprawling over 2 acres located minutes to Central Greenwich. Boasting 5 en-suite bedrooms, 5.5 luxurious bathrooms, formal living room with wet bar, multiple fireplaces, Gourmet Kitchen with an oversized island, Au pair suite with a private entrance spread out over 4,500 square feet. Beautiful stone walled gardens and terraces, fire

    Daniel DiPaolo BHHS New England Properties

    127 Dingletown Rd, Greenwich, CT 06830
  • /33

    $8,500 per month

    • 5 Beds
    • 3 Baths
    • 2,478 Sq Ft
    • House for Rent

    41 Leonard Ave, Riverside, CT 06878

    Riverside 5 bedroom colonial on .27 acres. Sun-filled with ideal flow for entertainment. Spacious formal rooms. Large family room with fireplace opens to amazing top of the line center island kitchen with granite counter tops and Viking, Sub-Zero and Fisher Paykel stainless steel appliances . Wood flooring and high-end lighting fixtures add to this level and full bath. French doors from the

    Ann Simpson BHHS New England Properties

    41 Leonard Ave, Riverside, CT 06878
  • /30

    $15,000 per month

    • 5 Beds
    • 5.5 Baths
    • 3,782 Sq Ft
    • House for Rent

    20 Martin Dale, Greenwich, CT 06830

    Ideally located , sun filled modern rental on .67 acres at the end of a coveted cul-de-sac just minutes from all the amenities that Greenwich offers. Close proximity to Brunswick, GA , North Street and GCDS schools . Living room with fireplace , formal dining room ,library / den , new kitchen with breakfast area and butler's pantry. Family room opens to terrace overlooking a beautifully

    Ryan Ciambriello Houlihan Lawrence

    20 Martin Dale, Greenwich, CT 06830
  • /40

    $16,000 per month

    • 7 Beds
    • 6.5 Baths
    • 8,954 Sq Ft
    • House for Rent

    57 Overbrook Dr, Stamford, CT 06906

    On one of Stamford's most beloved storybook streets, 57 Overbrook Drive offers charm, space, and a location that checks every box. Tucked on a quiet block, you'll enjoy a peaceful neighborhood feel just minutes from the train, shopping, schools, houses of worship, downtown, I-95, and the Merritt Parkway. With four finished levels, over 7,000 sq ft, and nearly two-thirds of an acre, the home is

    Jonathan Makovsky Compass Connecticut, LLC

    57 Overbrook Dr, Stamford, CT 06906
  • /61

    $16,000 per month

    • 5 Beds
    • 3.5 Baths
    • 2,874 Sq Ft
    • House for Rent

    1 Cherry Ln, Old Greenwich, CT 06870

    Location, Location, Location! Wonderful long term OG rental, south of the village on Cherry Lane. 5 Bed Rooms, 3.5 renovated bath rooms. mudroom, home office, formal living and dining rooms, eat in kitchen & family room with fireplace, large wrap around deck. Great outdoor entertaining space. Nice green yard to enjoy and garden. One car detached garage with storage. Garden Shed. Move in and

    Sheila Goggin BHHS New England Properties

    1 Cherry Ln, Old Greenwich, CT 06870
  • /68

    $39,500 per month

    • 6 Beds
    • 9 Baths
    • 8,482 Sq Ft
    • House for Rent

    59 Cat Rock Rd, Cos Cob, CT 06807

    The ideal country House for your unforgettable Summer/Fall In Greenwich. Available from August 1st - November 30th. This amazing shingle style home was custom built in 2010 and offers 8482 square feet of beautifully detailed interior spaces with high ceilings Throughout. Offering graciously scaled public rooms, a private study, gorgeous formal dining room, a gourmet kitchen with breakfast room,

    Stephen Archino Sotheby's International Realty

    59 Cat Rock Rd, Cos Cob, CT 06807
  • /49

    $20,000 per month

    • 6 Beds
    • 3.5 Baths
    • 3,275 Sq Ft
    • House for Rent

    13 Lockwood Ave, Old Greenwich, CT 06870

    SUMMER OR SHORT TERM FURNISHED RENTALLocated south of the village in Old Greenwich, a charming furnished 6 bedroom, 3 full bath Colonial with private, oversized backyard and large flagstone patio with lovely lush gardens for outdoor living. Bright, open floor plan with plenty of space. And a bonus Studio apartment over the Garage! The Studio has a Kitchen and full bath. Close to town, library,

    Sheila Goggin BHHS New England Properties

    13 Lockwood Ave, Old Greenwich, CT 06870
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