5-Bedroom Homes for Sale in Fairfield County CT

/40
$4,395,000
- 5 Beds
- 4.5 Baths
- 6,013 Sq Ft
29 Covelee Dr, Norwalk, CT 06855

Welcome to Saugatuck Shores, an exceptional waterfront enclave offering unparalleled luxury and privacy.A boater's dream come true w/ your own dock and direct access to LI Sound.This hidden gem neighborhood has a labyrinth of quiet,walkable streets, culminating in a cul-de-sac.Private Covlee Assn membership w/ sandy beach & social gatherings.The 5 bedroom high-end masterpiece w/ elevator was

Julie Vanderblue Higgins Group Real Estate

29 Covelee Dr, Norwalk, CT 06855
/31
$6,500,000
- 6 Beds
- 4 Baths
- 2,833 Sq Ft
0 Rich Island Unit 24092237, Greenwich, CT 06830

A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

Margriet McGowan Sotheby's International Realty

0 Rich Island Unit 24092237, Greenwich, CT 06830
/37
$6,500,000
- 6 Beds
- 4 Baths
- 2,833 Sq Ft
0 Rich Island Unit KEY855821, Greenwich, CT 06830

A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

Margriet McGowan Sotheby's International Realty

0 Rich Island Unit KEY855821, Greenwich, CT 06830
/37
$6,500,000
- 6 Beds
- 4 Baths
- 2,833 Sq Ft
0 Rich Island Unit 122625, Greenwich, CT 06830

A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

Margriet McGowan Sotheby's International Realty

0 Rich Island Unit 122625, Greenwich, CT 06830
/40
$2,895,000
- 6 Beds
- 4.5 Baths
- 6,856 Sq Ft
5 Northside Ln, Westport, CT 06880

A true Westport landmark, Staffordshire Hall is an extraordinary gated stone estate blending timeless grandeur with modern luxury. Privately nestled on manicured grounds, this bespoke manor spans three levels of meticulously crafted living space. A sweeping circular drive leads to the columned entrance. The Great Hall stuns with a stone hearth, coffered ceilings, and French doors opening to the

Alex Chingas Coldwell Banker Realty

5 Northside Ln, Westport, CT 06880
/38
$2,175,000
- 5 Beds
- 5 Baths
- 2,775 Sq Ft
39 Riverside Ave, Riverside, CT 06878

This light and bright 5BR, 4.1BA Colonial, renovated to the studs in 2021, features modern conveniences with original charm. The open floor plan offers a gourmet kitchen with quartz/marble countertops, new luxury baths, a woodburning fireplace, built-ins, convenient laundry/mudroom, and a finished 3rd floor with office, bedroom and full bath. Finished lower level (additional 365+ sf) with

Gloria Gimenez-Ferrer BHHS New England Properties

39 Riverside Ave, Riverside, CT 06878
/37
$1,150,000
- 5 Beds
- 4 Baths
- 5,148 Sq Ft
1115 Monroe Turnpike, Monroe, CT 06468

Step into timeless elegance with this stunning c.1800 Greek Revival Colonial. Offering over 5,100 sq ft of grand living space, this extraordinary home features a wealth of architectural charm throughout. Soaring high ceilings, original hardwood floors, 4 fireplaces set the tone for gracious living, while very large rooms provide space and storage rarely found in antique homes. A thoughtfully

Christopher Constand Higgins Group Real Estate

1115 Monroe Turnpike, Monroe, CT 06468
/40
$4,300,000
- 7 Beds
- 8 Baths
- 6,981 Sq Ft
102 Compo Rd S, Westport, CT 06880

THE ESTATES AT SOUTH COMPO - SIR Development presents a stunning new enclave of two luxury residences set back on beautiful property, each with their own distinct Modern style and pool. Officially designated by the State of CT as a Scenic Roadway, this location offers ultimate convenience to every amenity that makes Westport one of the most highly desired towns in the nation. This home begins

Doug Bross Coldwell Banker Realty

102 Compo Rd S, Westport, CT 06880
/38
$3,525,000 Open Sun 1PM - 3PM
- 5 Beds
- 6 Baths
- 4,668 Sq Ft
91 Turkey Hill Rd S, Westport, CT 06880

Welcome to 91 Turkey Hill Rd S a beautifully upgraded 5 bed 4 full and 2 half bath home blending classic charm with modern luxury. Every inch of this residence reflects thoughtful design and top tier craftsmanship. Step inside to discover 6 brand-new, spa-inspired bathrooms, meticulously renovated with the finest materials for a truly indulgent experience. HW floors and soaring ceilings thruout

Robert Appell Coldwell Banker Realty

91 Turkey Hill Rd S, Westport, CT 06880
/38
$1,599,000
- 5 Beds
- 4.5 Baths
- 4,930 Sq Ft
9 Blue Spruce Cir, Weston, CT 06883

Luxury & Convenience: Stunning Home Just Minutes from Merritt Parkway! Welcome to 9 Blue Spruce Circle-a masterfully designed, meticulously maintained 5-bedroom, 41/2-bath colonial, nestled on 2.03 private acres in picturesque Weston. Tucked away on a coveted cul-de-sac, this home seamlessly blends tranquility and convenience, with a charming pathway leading directly to Morehouse Farm Park.

Maria Tziolis William Pitt Sotheby's Int'l

9 Blue Spruce Cir, Weston, CT 06883
/40
$2,799,000
- 5 Beds
- 6.5 Baths
- 7,269 Sq Ft
342 Midlock Rd, Fairfield, CT 06824

Welcome to Summer Tree Gardens, an extraordinary stately home nestled on over 2 acres of meticulously maintained grounds in the prestigious Greenfield Hill neighborhood of Fairfield, CT. This expansive 7,269 sq. ft. home boasts 5 en-suite bedrooms, 8.5 baths, and an array of luxurious features that blend timeless elegance with modern updates. The home was built by builder Christer Krook. Step

Ken Osborn Higgins Group Bedford Square

342 Midlock Rd, Fairfield, CT 06824
/40
$2,350,000
- 5 Beds
- 4 Baths
- 3,099 Sq Ft
551 River Rd, Cos Cob, CT 06807

Bright newer five bedroom Center Hall Colonial near North Mianus school and minutes to Eastern Middle school , Riverside and Cos Cob shopping and RR stations. Third floor separate suite with bedroom, bath and office or sitting room. Hardwood floors , fenced in backyard. Great flow for day-to-day indoor and outdoor living and entertaining. Move-in condition.

Maria Arning BHHS New England Properties

551 River Rd, Cos Cob, CT 06807
/40
$5,950,000
- 6 Beds
- 9 Baths
- 8,817 Sq Ft
29 Sturges Commons, Westport, CT 06880

Masterfully crafted by Mattera Construction, this 12,000+/- sq ft residence sits on 1.3+/- pastoral acres on coveted Sturges Commons, a vibrant neighborhood known for block parties and a strong sense of community. Designed for both luxury and functionality, this home boasts exquisite custom finishes, soaring ceilings, and impeccable interior design. The main level offers a chef's kitchen, a

Doug Bross Coldwell Banker Realty

29 Sturges Commons, Westport, CT 06880
/33
$3,195,000
- 20 Beds
- 20 Baths
- 12,834 Sq Ft
191 Oak St, Bridgeport, CT 06604

Seize this exclusive investment opportunity at 191 Oak Street in Bridgeport, CT, now available through Top Tier Realty Group. This impeccable 3-story maintained brick building built in 1966 delivers immediate value with its 20 units-18 spacious one-bedrooms and 2 studios- all designed to maximize tenant satisfaction and minimize vacancies. Each thoughtfully configured apartment features the ideal

Lisa Nussbaum Top Tier Realty Group, LLC

191 Oak St, Bridgeport, CT 06604
/50
$6,800,000
- 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
/31
$699,000
- 5 Beds
- 3.5 Baths
- 3,168 Sq Ft
65 Cloverdale Ave, Shelton, CT 06484

This home can easily function as one level living- 3 bedrooms (including main bedroom), 2 1/2 baths, eat in kitchen, living room, dining room, family room with floor to ceiling field stone fireplace and spiral staircase, sun room, oversized garage and laundry all on ground level! Upstairs are 2 more bedrooms (one being used as an office), a full bath, great room with skylights, parque floor, wood

Persefone Burnett BHGRE Gaetano Marra Homes

65 Cloverdale Ave, Shelton, CT 06484
/17
$850,000
- 11 Beds
- 4 Baths
- 4,938 Sq Ft
1621 Stratford Ave, Stratford, CT 06615

Excellent Investment Opportunity with great cash flow. Legal 4 Family with 3 units occupied. Corner Building, Lot of parking space. Some units are recently remodeled. Rents can be higher, Long term tenants. Very Convenient Location - Close to I95 and bus line.

Aziz Seyal William Raveis Real Estate

1621 Stratford Ave, Stratford, CT 06615
/38
$4,500,000
- 5 Beds
- 5 Baths
- 5,272 Sq Ft
33 Cliffdale Rd, Greenwich, CT 06831

Stunning estate in Greenwich's prestigious Back Country. Set on 4 acres of rolling lawns, this 5,200+ sq ft Colonial blends timeless charm with modern luxury and privacy. Enter through a gated stone entrance to a home beautifully renovated by renowned Lighthouse Architects, with plans for expansion. The magnificent primary suite features a private boudoir, mahogany vaulted ceiling, and fireplace.

Marli Meier Corcoran Centric Realty LLC

33 Cliffdale Rd, Greenwich, CT 06831
/34
$3,195,000 Open Sun 1PM - 4PM
- 5 Beds
- 4.5 Baths
- 5,931 Sq Ft
148 W Hills Rd, New Canaan, CT 06840

Modern Elegance Meets Timeless Charm in Prime West Side Location. Welcome to the one you've been waiting for-where location, lifestyle, and luxury converge. Perfectly situated on 2 lush acres in a quiet neighborhood minutes from New Canaan village, this completely reimagined five-bedroom, four and a half bath home is the epitome of turnkey sophistication.Property Highlights include:The new

Hannelore Kaplan William Raveis Real Estate

148 W Hills Rd, New Canaan, CT 06840
/11
$679,000
- 8 Beds
- 3 Baths
- 3,749 Sq Ft
53-55 Fremont St, Bridgeport, CT 06605

Three Family house located in BRIDGEPORT CT . Legal three family fully rented and producing income. Welcome all investors to this great opportunity featuring 12 rooms, 8 bedrooms, three full baths approximately 3,000 sq ft, good sized units. If you are looking for an income investment look no further. Make an appointment for your tour today!

Rosania Melo Century 21 Scala Group

53-55 Fremont St, Bridgeport, CT 06605
/42
$27,950,000
- 8 Beds
- 12 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
/31
$2,700,000
- 5 Beds
- 3 Baths
- 4,170 Sq Ft
70 Redding Rd, Easton, CT 06612

This magnificent country estate includes the historic Thorp House on 8.8 acres of riverfront property, as well as a charming one bedroom cottage with attached 2 car garage. The main house, built in 1750, is listed on the National Register of Historic Places. Authentic period details grace the home with unique old world charm. Cathedral ceilings in the kitchen and great room make a stately

Charlotte Cotton William Raveis Real Estate

70 Redding Rd, Easton, CT 06612
/22
$4,900,000
- 7 Beds
- 5.5 Baths
- 7,995 Sq Ft
37 Green Acre Ln, Westport, CT 06880

A rare investment opportunity to own a storied 1936 estate on a desirable, private street in the heart of Westport. Set on 4.3 acres at the end of a tranquil cul-de-sac, this legacy property offers the ultimate in privacy and location, just one mile from both Westport's vibrant town center and the beach. The primary residence spans approximately 8,000 square feet, rich with timeless architecture

Lisa Bortz William Pitt Sotheby's Int'l

37 Green Acre Ln, Westport, CT 06880
/31
$6,500,000
- 6 Beds
- 6.5 Baths
- 6,585 Sq Ft
69 Beachside Ave, Westport, CT 06880

Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated

Doug Bross Coldwell Banker Realty

69 Beachside Ave, Westport, CT 06880
/39
$2,795,000
- 6 Beds
- 8 Baths
- 5,811 Sq Ft
463 N Salem Rd, Ridgefield, CT 06877

This gracious country estate's idyllic setting is the perfect backdrop for large family gatherings & joyous celebrations. For over 40 years, the Rosenthal family has cherished this sprawling sanctuary, creating a legacy of warmth & hospitality that is unmatched. Now the doors are open for a new owner to create timeless memories - whether poolside; sitting by the outdoor fireplace; cooking in the

Jay Contessa William Pitt Sotheby's Int'l

463 N Salem Rd, Ridgefield, CT 06877
/5
$769,000
- 8 Beds
- 4 Baths
- 2,390 Sq Ft
56 Calhoun Ave, Bridgeport, CT 06604

Four Family house located in BRIDGEPORT CT . Legal 4 family fully rented and producing income. Welcome all investors to this great opportunity featuring 16 rooms, 8 bedrooms, three full baths approximately 3,000 sq ft, good sized units. If you are looking for an income investment look no further. Make an appointment for your tour today!

Rosania Melo Century 21 Scala Group

56 Calhoun Ave, Bridgeport, CT 06604
/40
$2,400,000
- 5 Beds
- 3.5 Baths
- 2,889 Sq Ft
57 Main St, Ridgefield, CT 06877

Welcome to a timeless gem at 57 Main Street, Ridgefield, CT. This fabulous vintage Farmhouse Colonial has been completely renovated to the highest standards, blending sophistication with a casual, inviting vibe. The attention to detail is remarkable and features the latest design finishes and designer lighting. Nestled on a prime 1-acre level parcel, this home offers a highly desirable Main

Karla Murtaugh Compass Connecticut, LLC

57 Main St, Ridgefield, CT 06877
/40
$1,779,000
- 5 Beds
- 5.5 Baths
- 7,611 Sq Ft
28 Old Orchard Dr, Weston, CT 06883

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer.

Barbara Bross Coldwell Banker Realty

28 Old Orchard Dr, Weston, CT 06883
/40
$1,375,000
- 5 Beds
- 3.5 Baths
- 3,327 Sq Ft
64 Old Kings Hwy S, Darien, CT 06820

Own a piece of history with the Quintard-Frost House, a stunning antique Dutch Colonial home built in 1715 that seamlessly blends historic charm with modern comfort. This 5-bedroom, 3.5-bathroom residence showcases timeless craftsmanship, including original wide-plank floors, exposed beams, and period details throughout. At the heart of the home is a true antique bar with fireplace, a rare and

Seema Dohil Brown Harris Stevens

64 Old Kings Hwy S, Darien, CT 06820
/24
$965,000
- 14 Beds
- 8 Baths
- 5,052 Sq Ft
40-42 Jane St, Bridgeport, CT 06608

Welcome to 40-42 Jane St. in Bridgeport, Connecticut. Opportunity to own a spacious six family property with two large four bedroom one and a half bathroom apartments, two spacious two bedroom and one full bathroom apartments, and two large one bedroom one full bathroom apartments. Each apartment comes with an updated kitchen and bathroom, light and bright living room dining room, amole closet

Ben Weinberg Oxford Realty

40-42 Jane St, Bridgeport, CT 06608
/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
/40
$2,775,000
- 6 Beds
- 8 Baths
- 6,781 Sq Ft
47 Peaceable St, Ridgefield, CT 06877

Welcome to Peaceable Acres, a gracious turn-of-the-century estate situated on 2.14 picturesque acres in a walk-to-town location. Built in 1906 in the classic French Chateau style by renowned banker Albert Wiggin, this 6BR, 6/2 Bath property has been lovingly restored with an eye to preserve her original elegance. The home is an entertainer's dream with relaxed sophistication at every turn.

Kenny Rhodes eXp Realty

47 Peaceable St, Ridgefield, CT 06877
/40
$1,999,000 Open Sun 1PM - 3PM
- 5 Beds
- 7 Baths
- 7,166 Sq Ft
275 Newtown Turnpike, Weston, CT 06883

Nestled in a serene and private setting, this stunning custom colonial offers the perfect blend of elegance and comfort. Tucked away on over 2 acres of pristine landscape, this meticulously maintained home boasts an inviting layout with exceptional craftsmanship throughout. The sun-filled interior features a beautifully designed custom kitchen, perfect for entertaining. Step outside to a

Adriana Radu Coldwell Banker Realty

275 Newtown Turnpike, Weston, CT 06883
/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
/15
$825,000
- 5 Beds
- 4.5 Baths
- 2,670 Sq Ft
5 Betmarlea Rd, Norwalk, CT 06850

Fabulous 5-Bedroom Cape on a Picturesque Pond Welcome to this charming 5-bedroom Cape nestled beside a serene pond-perfect for those who love peaceful views and outdoor entertaining. Relax or host guests on the spacious patio overlooking the water, creating the ideal setting for memorable gatherings. Inside, the home offers incredible potential with a flexible layout. A separate entrance leads

Lisa Sader-Goede Aspen Realty Group

5 Betmarlea Rd, Norwalk, CT 06850
/31
$999,000
- 9 Beds
- 3 Baths
- 4,645 Sq Ft
439 Charles St Unit 443, Bridgeport, CT 06606

Very spacious legal three family home approximately 4,645 square feet of livable space in great condition, very well maintained! First floor features Open floor plan, central air, five rooms, two bedrooms, one full bath. Second floor unit with open floor plan five rooms, two bedrooms, one full bath. third floor unit with four rooms, two bedrooms, one full bath. Hardwood flooring throughout home,

Rosania Melo Century 21 Scala Group

439 Charles St Unit 443, Bridgeport, CT 06606
/38
$3,375,000
- 5 Beds
- 4 Baths
- 3,700 Sq Ft
3 Nassau Rd, Westport, CT 06880

Discover Westport's Premier Coastal Gem. Immerse yourself in modern elegance with this stunning new beach house, located in the highly sought-after Saugatuck Shores neighborhood. Constructed in 2022, this five-bedroom, four-and-a-half-bathroom residence spans over 3,700 square feet of finished living space. Tucked away on a peaceful cul-de-sac, the home offers easy access to the vibrant energy

Doug Bross Coldwell Banker Realty

3 Nassau Rd, Westport, CT 06880
/5
$779,000
- 10 Beds
- 4 Baths
- 3,424 Sq Ft
287 Dover St Unit 293, Bridgeport, CT 06610

Investor Opportunity or Perfect Owner-Occupied Multi-Family! Welcome to 287 Dover Street, Bridgeport, CT-an exceptional brick 4-family home offering a rare opportunity to own a solid, income-generating property in a convenient location. This well-maintained building features four spacious units, each with reliable, long-term tenants who pay on time every month-making it a turnkey investment from

Lisa Nussbaum Top Tier Realty Group, LLC

287 Dover St Unit 293, Bridgeport, CT 06610
/34
$6,995,000
- 5 Beds
- 7 Baths
- 8,685 Sq Ft
118 John St, Greenwich, CT 06831

Extraordinary, custom-built 5 bedroom stone + shingle Colonial is tucked away on 10 beautifully landscaped gated acres in serene backcountry. Sunlit 8685SF interior boasts generously scaled rooms w high ceils + stunning details incl four WB FPs + wide plank floors. The house is designed to take full advantage of picturesque setting bringing the outside in from all rooms. 1st floor has an open

B.K. Bates Houlihan Lawrence

118 John St, Greenwich, CT 06831
/37
$1,150,000
- 5 Beds
- 4.5 Baths
- 5,906 Sq Ft
65 Joes Hill Rd, Danbury, CT 06811

Grand Estate Opportunity in Danbury's Coveted Aunt Hack Neighborhood. Discover a fabulous opportunity to own a distinguished and architecturally striking home in the highly sought-after Aunt Hack neighborhood on Danbury's west side. Set back on 1.84 private, park-like acres, this stately 5906 sq. ft residence offers timeless curb appeal and the potential to craft your dream estate. From the

Patty Wagner Compass Connecticut, LLC

65 Joes Hill Rd, Danbury, CT 06811

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