5-Bedroom Homes for Sale in Fairfield County CT

/37
$3,100,000 Open Sat 1PM - 4PM
- 5 Beds
- 4.5 Baths
- 4,000 Sq Ft
450 Penfield Rd, Fairfield, CT 06824

New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury-just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, the train, and top-rated schools. With 5-6 bedrooms, 4.5 baths, and 3 finished levels, this elevator-ready home offers exceptional design, flow, and comfort. The open concept kitchen is both functional and

Julie Vanderblue Higgins Group Real Estate

450 Penfield Rd, Fairfield, CT 06824
/39
$999,999 Open Sat 12PM - 3PM
- 6 Beds
- 7 Baths
- 4,769 Sq Ft
7 Old Bethel Rd, Newtown, CT 06470

Secluded Luxury - Your Private Country Estate Awaits Set on 8.32 private acres of rolling woodlands and open meadows, this fantastic estate offers an exceptionally private setting-tucked high above the road and wrapped in natural beauty. Experience peace and quiet in a truly tranquil environment, while still being just minutes from the town center, shopping, and everyday amenities. The private

Stephanie Barnes William Raveis Real Estate

7 Old Bethel Rd, Newtown, CT 06470
/38
$4,395,000
- 5 Beds
- 4 Baths
- 4,791 Sq Ft
9 Sylvester Ct, Norwalk, CT 06855

Unbelievable value directly on the water with a private dock! On the coveted shores of Gregory Point and Norwalk Harbor sits this spectacular waterfront property. Welcome to a home where every room is graced by sweeping water views, and every sunset feels like a private show. This renovated farm style home is more than just move in ready, it is coastal living at its finest. The heart of the house

Meghan Gatt William Raveis Real Estate

9 Sylvester Ct, Norwalk, CT 06855
/52
$13,995,000
- 5 Beds
- 9 Baths
- 10,431 Sq Ft
190 North St, Greenwich, CT 06830

Nor Tor stands as one of Greenwich's finest English Manors, an extraordinary estate spanning nearly 3.5 acres of breathtaking beauty. Meticulously preserved, the manor underwent an extensive three year restoration and expansion, completed in 2010, blending historical integrity with seamless enhancements. This masterful renovation was led by architect Ira Grandberg, resulting in a breathtaking

Leslie McElwreath Sotheby's International Realty

190 North St, Greenwich, CT 06830
/34
$7,495,000
- 6 Beds
- 11 Baths
- 7,528 Sq Ft
229 Umpawaug Rd, Redding, CT 06896

Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and

Stacy Young William Raveis Real Estate

229 Umpawaug Rd, Redding, CT 06896
/29
$599,999
- 10 Beds
- 3 Baths
- 3,162 Sq Ft
485 Laurel Ave, Bridgeport, CT 06605

Investors take note! CASH offers preferred! BIG PRICE REDUCTION-$$$ 13 room- licensed rooming house(Residential Business zone) with excellent income potential. Check with your lender for applicable loans! Opportunities abound to start to choose your own tenants at market rate. Well maintained and code compliant property includes open concept kitchen, dining area, living room, sunroom with

Joe Martin VP Realty, Inc.

485 Laurel Ave, Bridgeport, CT 06605
/7
$925,000
- 12 Beds
- 3.5 Baths
- 8,596 Sq Ft
483 Barnum Ave, Bridge Port, CT 06608

This well-maintained mixed-use investment is in the heart of Bridgeport, CT. This large brick corner building features four spacious 3-bedroom residential units, two income-producing storefronts, a 600 SF garage, and an additional industrial parcel at 489 Barnum Ave also available. Utilities are separately metered, offering ease of management and long-term added value.

John Grubiak Surf Realty LLC

483 Barnum Ave, Bridge Port, CT 06608
/37
$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
/3
$925,000
- 6 Beds
- 4 Baths
- 5,200 Sq Ft
32 Echo Valley Rd, Newtown, CT 06470

BEAUTIFULL COLONIAL HOME APPROXIMATELY 1 HOUR AWAY FROM NEW YORK CITY

Jose Soto Essential Realty Group LLC

32 Echo Valley Rd, Newtown, CT 06470
/27
$11,500,000
- 7 Beds
- 12 Baths
- 10,058 Sq Ft
35 Andrews Farm Rd, Greenwich, CT 06831

Elegantly updated & impeccably maintained, this 10K+ SF estate is set on 8 manicured acres in the exclusive, gated Andrews Farm Association. Offering 7 bedrooms & 7.5 baths, this timeless home blends classic architecture with modern convenience, including a recent renovation featuring modern systems & smart home technology. The grounds, designed by renowned landscape architect Penelope Hobhouse,

Kevin Sneddon Compass Connecticut, LLC

35 Andrews Farm Rd, Greenwich, CT 06831
/26
$9,500,000
- 7 Beds
- 12 Baths
- 10,058 Sq Ft
35 Andrews Farm Rd, Greenwich, CT 06831

Exquisitely designed home defines elegance and exclusivity. This one of a kind 7 bedroom, 7/5 bath, 10,000+ square foot estate home in the Andrews Farm Association, nestled in the prestigious back country of Greenwich. Situated on 4 manicured acres, this property boasts an awe-inspiring garden designed by Penelope Hobhouse; featuring fruit orchards, a greenhouse, raised vegetable gardens,

Kevin Sneddon Compass Connecticut, LLC

35 Andrews Farm Rd, Greenwich, CT 06831
/41
$5,900,000
- 6 Beds
- 10 Baths
- 7,438 Sq Ft
27 Stiles Ln, Greenwich, CT 06831

Grand Greenwich Estate | Luxurious Living on 4.3 Acres Nestled at the end of a quiet cul-de-sac, 27 Stiles Lane is a magnificent brick manor set on 4.3 private acres of lush, manicured grounds. Offering 7,438 square feet of refined living space, this exceptional estate is designed for those who appreciate elegance, comfort, and unparalleled amenities. Inside, the grandeur unfolds with six ensuite

Fatou Niang Julia B Fee Sothebys Int. Rlty

27 Stiles Ln, Greenwich, CT 06831
/40
$2,599,000
- 5 Beds
- 6.5 Baths
- 5,506 Sq Ft
79 Comstock Hill Ave, Norwalk, CT 06850

This stunning architectural masterpiece, nestled in the prestigious Silvermine neighborhood, offers nearly 8,000 square feet of unparalleled luxury. Upon entry, a grand two-story foyer makes an unforgettable first impression, featuring a striking marble staircase and an ornate chandelier that sets the tone for elegance throughout. Radiant floor heating ensures warmth and comfort during the cooler

Demetrios Frazis William Pitt Sotheby's Int'l

79 Comstock Hill Ave, Norwalk, CT 06850
/26
$2,790,000
- 9 Beds
- 5.5 Baths
- 7,437 Sq Ft
26 Shady Ln, Greenwich, CT 06831

Discover the enduring beauty of this stately 1900 Georgian Colonial. Set on a corner lot on one acre offers over 7,500 square feet of living space, 9 bedrooms, 5 full bathrooms, and 8 working fireplaces, a true testament to timeless elegance and old-world craftsmanship. Step inside and you're greeted by exquisite period details, ornate millwork, soaring 12ft ceilings, original leaded glass

Kaori Higgins Higgins Group Greenwich

26 Shady Ln, Greenwich, CT 06831
/51
$11,400,000
- 8 Beds
- 10 Baths
- 10,935 Sq Ft
151 Old Church Rd, Greenwich, CT 06830

''Oak Castle Farm'', an extraordinary 7-bedroom turn-of-the-century English-style granite and shingle home, masterfully renovated and expanded under the supervision of noted architect, Alisberg Parker. Stunning 2014 transition incorporates relaxed grandeur with all modern-day luxuries. Exquisite detail, quality and scale with high ceilings throughout. Spectacular landscape and manicured grounds

John McAtee Coldwell Banker Realty

151 Old Church Rd, Greenwich, CT 06830
/57
$5,495,000
- 5 Beds
- 10 Baths
- 10,640 Sq Ft
8 Chieftans Rd, Greenwich, CT 06831

GRAND, GRAND, GRAND with 10,000+ sq.ft. lifestyle. Greenwich's prestigious loc. CHIEFTANS offering 24/7 gatehouse sec.+concierge serv. Impressive wrought iron gates swing open, they reveal the allee of pear trees to paradise.This est's prop. was the orig. 1911 Borden Milk fortune. Bespoke without maintenance. One of the larger palatial gems sitting back against the Fairchild Gardens Nature

Janet Milligan Sotheby's International Realty

8 Chieftans Rd, Greenwich, CT 06831
/40
$2,995,000
- 5 Beds
- 8 Baths
- 6,905 Sq Ft
1187 Smith Ridge Rd, New Canaan, CT 06840

Nestled at the end of a private lane and set on 4.4 beautifully landscaped acres, this stunning brick colonial-crafted by award-winning builder Kaali-Nagy-offers nearly 7,000 square feet of luxurious living space. A dramatic three-story entryway fills the home with natural light, leading into a formal living room with a fireplace and French doors. A richly paneled office tucked just behind the

Melissa Rwambuya William Raveis Real Estate

1187 Smith Ridge Rd, New Canaan, CT 06840
/40
$5,495,000
- 6 Beds
- 5.5 Baths
- 6,543 Sq Ft
86 Wallacks Dr, Stamford, CT 06902

Prestigious Waterfront Estate at Wallack's Point Experience the pinnacle of coastal luxury with this once-in-a-lifetime opportunity to own 1.46 acres of DIRECT Long Island Sound frontage in the gated enclave of Wallack's Point. With sweeping, unobstructed water views and nightly sunsets that feel like art, this premier waterfront property is among the most coveted on the Connecticut shoreline.

Carla Kupiec William Raveis Real Estate

86 Wallacks Dr, Stamford, CT 06902
/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
$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
/25
$2,350,000
- 5 Beds
- 3.5 Baths
- 3,634 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. Total Sq. footage includes 535 sq. ft. below grade.

Maria Arning BHHS New England Properties

551 River Rd, Cos Cob, CT 06807
/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
/34
$3,195,000
- 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
/42
$27,950,000
- 8 Beds
- 11.5 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
/26
$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
/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
/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
/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
$810,000
- 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

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