5-Bedroom Homes for Sale in Fairfield County CT

/40
$4,250,000 Open Sat 12PM - 3PM
- 6 Beds
- 8.5 Baths
- 6,897 Sq Ft
1084 Sturges Hwy, Westport, CT 06880

Luxury Living on the Fairfield/Westport Border Set in the heart of Greenfield Hill, this exceptional 6-bedroom, 8-bath estate offers a rare combination of privacy, elegance, and resort-style amenities-just minutes from the Post Road and 50 miles from NYC. Thoughtfully positioned on the Fairfield/Westport line, the residence features expansive, sun-filled interiors ideal for everyday living and

Andrew Whiteley Brown Harris Stevens

1084 Sturges Hwy, Westport, CT 06880
/35
$829,000
- 5 Beds
- 3 Baths
- 3,287 Sq Ft
152 Richards Dr, Monroe, CT 06468

Welcome to your dream home, meticulously renovated from top to bottom with no detail spared. This 5-bedroom, 3-bathroom residence offers over 3,200 sq ft of modern living space and sits on a beautifully manicured, private lot in desirable Monroe, CT. Enjoy an open-concept layout featuring a brand-new designer kitchen with stainless steel appliances, quartz countertops, abundant cabinetry, and

Abdelkader Hassan Coldwell Banker Realty

152 Richards Dr, Monroe, CT 06468
/38
$2,300,000 Open Sun 2:30PM - 4:30PM
- 7 Beds
- 3 Baths
- 3,486 Sq Ft
10 Hillcrest Ct, Ridgefield, CT 06877

Be captivated by spectacular views of Lake Mamanasco and beyond from this stunning Modern Retreat. Wake up every morning to full panoramic views of a magical sunrise and the mountains beyond. One of the most picturesque settings in Ridgefield. With amazing sight-lines from all three levels of finished space, this beautifully maintained home offers a private, year round resort-like lifestyle.

Karla Murtaugh Compass Connecticut, LLC

10 Hillcrest Ct, Ridgefield, CT 06877
/2
$739,900
- 5 Beds
- 3 Baths
- 1,732 Sq Ft
41 Young Dixon Way, Stamford, CT 06902

Excellent Investment property with Income potential,This legal 3 Family home is located on the West Side of Stamford,CT. Convenient to Train Station,I95 and walking distance to shops,hospital,parks and restaurants. Currently rented all tenants on month to month. Showings Monday through Saturday Only. This property is being sold as-is and the buyer must do their own due-diligence.

Jacqueline Castro Keller Williams Prestige Prop.

41 Young Dixon Way, Stamford, CT 06902
/37
$8,490,000
- 5 Beds
- 7 Baths
- 4,448 Sq Ft
10 W Crossway, Old Greenwich, CT 06870

See Video....Welcome to your dream vacation-like setting! This bright and spacious 5 bed 7 bath property boasts a tranquil ambiance with stunning sunsets that will take your breath away. Perfect for cozy evenings looking at the water. Multiple options for offices including bonus space above the garage are the perfect Zoom refuge. Entertain and relax on the inviting patios while taking in the

Christian Perry Sotheby's International Realty

10 W Crossway, Old Greenwich, CT 06870
/43
$3,895,000 Open Sun 2PM - 4PM
- 6 Beds
- 5.5 Baths
- 5,175 Sq Ft
119 Hendrie Ave, Riverside, CT 06878

This spacious Riverside Colonial is located on one of the less traveled streets extending from Riverside School to Binney Park. Artfully expanded & renovated from its original 40's design, the main rooms feature high ceilings, wide windows and generous scale. The dramatic three-story entrance hall is flanked by a formal living room & large family room , both w handsome fireplaces, & it extends

Heather Platt Sotheby's International Realty

119 Hendrie Ave, Riverside, CT 06878
/35
$439,900
- 6 Beds
- 2 Baths
- 2,260 Sq Ft
330 French St, Bridgeport, CT 06606

Welcome to 330 French Street! If you're searching for the perfect home for an extended or growing family, look no further. This spacious residence offers three full levels of living space, ideal for comfort, flexibility, and functionality. Step into a large foyer that leads into an open-concept dining area and kitchen-perfect for entertaining, with room to seat up to 20 guests. The enormous

Nina Nyrop RE/MAX Right Choice

330 French St, Bridgeport, CT 06606
/37
$1,695,000 Open Sat 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 3,480 Sq Ft
59 Snowberry Ln, New Canaan, CT 06840

Opportunity Awaits! Bring your vision to this COLONIAL in desirable New Canaan. Potential for customization is limitless. Gorgeous 2 park-like acres with pond access and aerator welcomes you. Property features a peaceful yard, mature shade trees that line the driveway and lend privacy. Picturesque walking/biking community where neighbors gather. Wrap around porch invites you to sit, read, chat

Heather McGuinness William Raveis Real Estate

59 Snowberry Ln, New Canaan, CT 06840
/24
$949,900
- 14 Beds
- 8 Baths
- 5,052 Sq Ft
40 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, ample closet

Ben Weinberg Oxford Realty

40 Jane St, Bridgeport, CT 06608
/29
$429,900
- 6 Beds
- 3 Baths
- 2,493 Sq Ft
295 Shelton St, Bridgeport, CT 06608

Welcome to 295 Shelton Street, a well-positioned 3-family property featuring three spacious 2-bedroom, 1-bath units. Perfect for investors seeking cash flow with upside, this property offers a solid layout, separate utilities, and strong rental demand in the area. Each unit provides a functional floor plan with great potential for updates to significantly increase rental income and overall value.

Anthony La Penna Complete Real Estate

295 Shelton St, Bridgeport, CT 06608
/7
$8,750,000
- 6 Beds
- 7.5 Baths
- 10,400 Sq Ft
11 Winterset Rd, Greenwich, CT 06830

Mid Country New Construction smart home on 2.16 exquisite level acres will be completed by early fall, 2025. 10K+ SF of finished space on 4 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th en-suite bedroom on 3rd floor. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular indoor / outdoor living is designed

Amanda Bates Houlihan Lawrence Inc.

11 Winterset Rd, Greenwich, CT 06830
/40
$6,950,000
- 5 Beds
- 7.5 Baths
- 14,038 Sq Ft
11 Beachside Common, Westport, CT 06880

A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive homes on the Connecticut coast-known to anyone who's ever strolled Burying Hill Beach. Set on 2.6 waterfront acres, the property offers sweeping southern views over Sherwood Island and Long Island Sound, with sunsets that rival the Low Country and birdlife that fills the surrounding marsh with movement and

Wendy Ryan Brown Harris Stevens

11 Beachside Common, Westport, CT 06880
/39
$749,000
- 5 Beds
- 2.5 Baths
- 3,463 Sq Ft
21 Lillinonah Dr, Brookfield, CT 06804

Savor the amazing views of Lake Lillinonah from this classic split-level home set on over 2 acres of park-like grounds. Elevated to maximize its scenic surroundings, the property offers sweeping vistas of the nearby waterfront, with mature landscaping, stone walls, and a gracious front lawn shaded by stately trees. Inside, the versatile layout provides generous space for both comfortable daily

Kellie Martone William Pitt Sotheby's Int'l

21 Lillinonah Dr, Brookfield, CT 06804
/40
$1,950,000
- 5 Beds
- 7 Baths
- 6,127 Sq Ft
124 Princess Pine Ln, Fairfield, CT 06824

Set on 2.98 private acres at the end of a cul-de-sac in coveted Greenfield Hill, this elegant 4627+ SF Colonial offers the perfect blend of luxury, space, and functionality. From the grand 2-story foyer to the exquisite crown moldings, every detail exudes timeless sophistication. Designed for entertaining, the home features a gracious flow with expansive living and gathering spaces, a gourmet

Elizabeth Tritschler William Raveis Real Estate

124 Princess Pine Ln, Fairfield, CT 06824
/26
$3,895,000
- 5 Beds
- 3.5 Baths
- 3,647 Sq Ft
258 Riverside Ave, Riverside, CT 06878

Tucked away down a private driveway off Riverside Avenue, this stylishly updated, cedar-clad home offers the perfect blend of classic charm and modern farmhouse appeal. Set on over a half an acre of level lawn, this peaceful retreat is just minutes from the train, town and coastline. The sun-filled living room, framed by twin picture windows, sets a warm and welcoming tone. At the center of the

Tracey Koorbusch Sotheby's International Realty

258 Riverside Ave, Riverside, CT 06878
/40
$4,295,000 Open Sun 1PM - 3PM
- 5 Beds
- 9 Baths
- 13,457 Sq Ft
1247 Oenoke Ridge, New Canaan, CT 06840

AMAZING opportunity to breathe fresh life into this Magnificent Estate! Luxurious style and surroundings including pool and pool house on four acres at this stately address. Over 13,400 square feet of luxury on four finished floors with elegant rooms and flow, including a double story library, lavish primary suite, and fantastic lower level with bar, wine cellar and gym.

Kelly Defrancesco William Raveis Real Estate

1247 Oenoke Ridge, New Canaan, CT 06840
/11
$689,000
- 6 Beds
- 4 Baths
- 2,956 Sq Ft
315 Nichols St, Bridgeport, CT 06608

315 Nichols St #317, Bridgeport provides 4 recently upgraded residential apartments and 1 detached garage. The property is located on a corner lot providing unobstructed access to the rear yard and detached garage. Easy access to Amtrak/Metro North Station, Interstate 95, Routes 8, 25, 1, 15, 111, 59, 130 and 127. The immediate area includes Boca Oyster Bar & Marina and the Hartford Amphitheater.

Aileen O'Connell Coldwell Banker Realty

315 Nichols St, Bridgeport, CT 06608
/40
$1,115,900
- 5 Beds
- 4 Baths
- 3,717 Sq Ft
43 Moose Hill Rd, Trumbull, CT 06611

This beautifully built 5-bedroom, 4-bath colonial blends classic elegance with modern luxury in a serene interior lot setting. Meticulously rebuilt from the ground up, the home now boasts an additional $30000 in professional landscaping, including 30 fast growing trees for added privacy. Inside, the open-concept main level is a showstopper. The chef's kitchen is outfitted with granite

Douglas Ledewitz Pulse Realty LLC

43 Moose Hill Rd, Trumbull, CT 06611
/40
$1,475,000
- 6 Beds
- 8 Baths
- 5,797 Sq Ft
20 Fieldstone Dr, Easton, CT 06612

D. FAIRCHILD WHEELER ESTATE - Built in 1949 for the well-known philanthropist, this stately home sits majestically atop a sweeping front lawn w/ breathtaking views. This 5+ acre estate includes the 6-bedroom home w/ adjacent 2-bedroom in-law apartment/legal rental, a gunite pool & spa tub, multiple outbuildings & scenic views in every direction. The main house is brimming w/ old world charm

Gayle Worthington William Raveis Real Estate

20 Fieldstone Dr, Easton, CT 06612
/19
$1,399,000
- 7 Beds
- 3 Baths
- 2,760 Sq Ft
212 Davis Ave, Greenwich, CT 06830

Renovated 3-Unit Multi-Family - Prime Location in Greenwich, CT! Whether you're looking to generate solid rental income or occupy one unit while renting out the others, this is a rare opportunity in the heart of Greenwich. Conveniently located near Greenwich Avenue, parks, schools, Metro-North, and I-95. Updates include: new roof, siding, insulation, electrical...

Nico Jackson Corcoran Centric Realty

212 Davis Ave, Greenwich, CT 06830
/32
$999,000 Open Sat 1PM - 3PM
- 5 Beds
- 2 Baths
- 1,952 Sq Ft
Unlisted Address

Discover a rare opportunity to own this light-filled and versatile one-level ranch with a fully finished walk-out lower level-perfect for a young adult suite, nanny or in-law. Thoughtfully designed for flexibility and comfort, this home offers 5 bedrooms and 2 full bathrooms, including brand-new stainless steel appliances in the eat-in kitchen. Enjoy the warmth of the fireplace in the living

Kerri Curtin William Pitt Sotheby's Int'l

Unlisted Address
/40
$5,725,000
- 7 Beds
- 9 Baths
- 13,615 Sq Ft
9 Greenbrier Rd, Westport, CT 06880

Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage with modern luxury. At its core: a preserved 1930 Frazier Peters stone cottage-now a 2-bed, 2-bath guest house. At its heart: a 2007 custom-built

Cindy Raney Coldwell Banker Realty

9 Greenbrier Rd, Westport, CT 06880
/40
$1,895,000
- 5 Beds
- 4 Baths
- 4,056 Sq Ft
31 Riverfield Dr, Weston, CT 06883

The Perfect Trifecta: River, Pool, Court with special appointments. This breathtaking estate is a true love letter to both nature and craftsmanship. A rare and intimate retreat, it offers a private sanctuary where the rhythm of the river sets the pace of life. Imagine waking to the gentle murmur of water, with the beauty of the river unfurling before whether you're kayaking at sunrise or fishing

Betty Stroll William Raveis Real Estate

31 Riverfield Dr, Weston, CT 06883
/40
$1,500,000
- 5 Beds
- 6 Baths
- 5,189 Sq Ft
40 Walnut St, Monroe, CT 06468

Welcome to this magnificent custom-built raised ranch known as 40 Walnut Street located in Fairfield County in the Town of Monroe. Monroe is a beautiful community that offers a balanced blend of suburban amenities, many opportunities for recreation, scenic beauty and rural character. Whitney Farms Golf Course is a three-minute drive and features a clubhouse, pro-shop and catering facility for all

Stephen Hodson Hodson Realty, Inc.

40 Walnut St, Monroe, CT 06468
/34
$949,000
- 5 Beds
- 4.5 Baths
- 3,862 Sq Ft
21 October Ln, Trumbull, CT 06611

Beautifully updated colonial with luxury finishes and exceptional outdoor Space. Welcome to this stunning, fully updated Colonial offering 5 spacious bedrooms and 4.5 beautifully appointed bathrooms. From the moment you step inside, gleaming hardwood floors and timeless architectural details set the tone for refined living. The heart of the home is the gourmet kitchen, featuring custom cabinetry,

Jaime Pote Coldwell Banker Realty

21 October Ln, Trumbull, CT 06611
/40
$1,400,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 3,817 Sq Ft
7 Topping Ln, Norwalk, CT 06854

Tucked away at the end of a private road in Norwalk's Brookside neighborhood, 7 Topping Lane offers rare privacy and space on 2.39 acres. This 5-bedroom 4.5-bath Tudor-style home combines timeless charm with modern updates. The open-concept main level features dramatic 17-foot cathedral ceilings, a striking wood-burning stone fireplace, and exposed beams. The updated kitchen boasts quartz

Brandy Hall Higgins Group Real Estate

7 Topping Ln, Norwalk, CT 06854
/13
$639,000
- 6 Beds
- 3 Baths
- 3,687 Sq Ft
170 Livingston Place Unit 172, Bridgeport, CT 06610

First time on market. Large three family in beautiful Beardsley Park area. Six rooms first and second floors include enclosed heated porches. Living room dining room and two bedrooms each , with four rooms on third floor. Two car detached garage and cute little back yard. All apartments are rented $2050 $1600 $1500

Cynthia Gennarini Town & Country Investments

170 Livingston Place Unit 172, Bridgeport, CT 06610
/40
$1,395,000 Open Sat 2PM - 4PM
- 6 Beds
- 3.5 Baths
- 3,508 Sq Ft
1135 Hulls Farm Rd, Southport, CT 06890

A prime Southport estate location at the Westport line is home to this gracious 5 Bedroom Colonial featuring a rarely found attached main level IN-LAW / AU PAIR APARTMENT with a private entrance, Living/Dining Room, Bedroom and a full Bath. Additionally appreciated, and perfect for today's work from home buyer, is an OFFICE/STUDIO over the barn style oversized detached two car garage. Approached

Paul Triantafel William Pitt Sotheby's Int'l

1135 Hulls Farm Rd, Southport, CT 06890
/37
$3,399,000 Open Sat 12PM - 2PM
- 5 Beds
- 5 Baths
- 3,961 Sq Ft
318 320 Pine Creek Ave, Fairfield, CT 06824

Welcome to a truly exceptional opportunity-a direct waterfront compound offering expansive views of Long Island Sound, a dock, &endless showstopping sunsets. This remarkable property features 2 residences: a fully renovated, FEMA-compliant main house AND a charming, income-generating guest cottage.The Main Residence (320)is a modern coastal retreat offering 3,129 sq ft of sun-drenched living

Deirdre Andreoli Compass Connecticut, LLC

318 320 Pine Creek Ave, Fairfield, CT 06824
/21
$6,600,077 Open Sun 1PM - 3PM
- 6 Beds
- 7.5 Baths
- 7,580 Sq Ft
14 5 Mile River Rd, Darien, CT 06820

World class one of a kind newly constructed modern masterpiece designed by award winning architect Vita Design with stunning unobstructed water views from every room in the house. This custom coastal build sets luxury to the highest level. The home features tall ceilings with an abundance of open space filled with natural light coming in through the floor to ceiling oversized European style

Jennifer DaSilva Mixer William Raveis Real Estate

14 5 Mile River Rd, Darien, CT 06820
/37
$1,139,000
- 5 Beds
- 3 Baths
- 4,359 Sq Ft
4 Whippoorwill Ln, Weston, CT 06883

Discover exceptional living at this distinguished 5-bedroom, 3-bathroom ranch home spanning over 5,000 square feet on prestigious Whippoorwill Lane in coveted Weston. Built in 1955 and situated on a magnificent 1.72-acre lot, this timeless residence offers the perfect blend of classic New England charm and modern potential in one of the most sought-after communities. Ready for a new homeowners

Christine Oleynick Keller Williams Realty

4 Whippoorwill Ln, Weston, CT 06883
/40
$3,995,000
- 8 Beds
- 9 Baths
- 12,853 Sq Ft
27 Country Club Rd, Ridgefield, CT 06877

"HOMEWOOD" - This remarkable country compound is one of the precious few 18th/19th century shingle style colonial revival estates remaining in Fairfield Cty. Dating back to 1750, the original pre-revolutionary war home captivated the attention of prominent NYC banker, George Haven, who purchased the home in 1890 & expanded it significantly including a glorious 50' ballroom designed by Elsie de

Laura Ancona William Pitt Sotheby's Int'l

27 Country Club Rd, Ridgefield, CT 06877
/40
$2,398,000
- 10 Beds
- 7.5 Baths
- 4,403 Sq Ft
465 Edward St, Fairfield, CT 06824

Extremely rare opportunity to own a side-by-side, Colonial style duplex with over 4400sqft in total and 10 bedrooms-in the heart of the Fairfield beach area. The home is currently rented each academic year through May 2028. Cap spreadsheet is in attachments, illustrating the very positive income flow. Academic rental $19,000-$21,000 per month for entire house. Converting to a 10-month lease after

Jessica Walsh William Raveis Real Estate

465 Edward St, Fairfield, CT 06824
/15
$460,000
- 5 Beds
- 2 Baths
- 1,344 Sq Ft
6 Lane Ave, Trumbull, CT 06611

Cozy Cape Cod style home just waiting for you! five rooms, three bedrooms, two full baths, living room with light bright windows, dining room, updated kitchen and finished basement that gives you opportunity for more livable space! good size level yard and a oversized front porch for sitting & relaxing morning, noon or night. Tankless gas water heating. DO NOT MISS THIS OPPORTUNITY To turn this

Rosania Melo Century 21 Scala Group

6 Lane Ave, Trumbull, CT 06611
/29
$735,000
- 6 Beds
- 3 Baths
- 3,054 Sq Ft
155 Summerfield Ave Unit 157, Bridgeport, CT 06610

Well maintained 3 multi-family property in nice neighborhood near hospital and highway. First floor unit newly renovated with closed in front sun porch. Large background for entertainment. All units have separate meters and washer & dryer hook up in the units. Great cash flow investment. A must see.

Marilyn Profit Coldwell Banker Realty

155 Summerfield Ave Unit 157, Bridgeport, CT 06610
/40
$2,500,000
- 5 Beds
- 7 Baths
- 10,208 Sq Ft
7 Taunton Ln, Newtown, CT 06470

Discover this one-of-a-kind custom built Cape style home set on a breathtaking 15-acre estate. Designed with luxury and functionality in mind, this 5 to 6 bedroom, 5 full, 2 half-bath residence offers expansive living spaces and extraordinary attention to detail. The heart of the home is a gourmet kitchen featuring granite countertops, high-end SS appliances, custom cabinetry, and a sun-drenched

Jen Sanderson William Raveis Real Estate

7 Taunton Ln, Newtown, CT 06470
/24
$1,250,000
- 5 Beds
- 4 Baths
- 3,209 Sq Ft
36 N Taylor Ave, Norwalk, CT 06854

Opportunity Knocks in the Heart of Norwalk! 36 Taylor Avenue offers the perfect blend of location, income potential, and long-term upside. This 4-unit multifamily is a true cash flow opportunity-turnkey and ready to generate rental income from day one. Whether you're a seasoned investor looking to expand your portfolio or a new comer seeking passive income, this property checks all the boxes.

Arian Hoxha Serhant Connecticut, LLC

36 N Taylor Ave, Norwalk, CT 06854
/40
$1,699,000 Open House 9/14
- 5 Beds
- 4.5 Baths
- 4,010 Sq Ft
92 Westwood Rd, Fairfield, CT 06825

Gorgeous new construction on a private cul-de-sac backing up to Brooklawn Country Club. Absolutely amazing level yard on almost a half acre w sprinkler system, substantial patio and room for a pool and in addition, space for many other outdoor toys. This 5 bedroom, 4.5 bath home is spectacular from top to bottom. Over 3000 sq. ft on two levels. First level with living room w stunning New Mont

Bette Gigliotti William Raveis Real Estate

92 Westwood Rd, Fairfield, CT 06825
/40
$1,299,000
- 5 Beds
- 3.5 Baths
- 3,611 Sq Ft
101 Golden Hill St, Trumbull, CT 06611

"A Premier Waterfront Sanctuary"! Please view the fabulous virtual tour of this property at (101goldenhill.com) for spectacular drone imaging here on tranquil "Dogwood Lake", (spring fed) in historic "Nichols" & the award winning "Booth Hill School District". Resort styled living inside & out w/established perennial & raised bed vegetable gardens, level lawn spaces, (irrigated) stretching out to

Kenneth Martin William Raveis Real Estate

101 Golden Hill St, Trumbull, CT 06611
/37
$2,000,000
- 5 Beds
- 4.5 Baths
- 6,370 Sq Ft
40 Cascade Rd, Stamford, CT 06903

Welcome to 40 Cascade Road, a beautifully appointed and expansive home offering timeless elegance, modern amenities, and a layout designed for luxurious living and effortless entertaining. As you enter through the grand two-story foyer, you're greeted by gleaming hardwood floors and an abundance of natural light that flows throughout. The spacious living room, featuring a gas-burning fireplace,

Chris Carozza RE/MAX Right Choice

40 Cascade Rd, Stamford, CT 06903

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