5-Bedroom Homes for Sale in Fairfield County CT

/40
$2,950,000 Open Sun 12PM - 2PM
- 6 Beds
- 8 Baths
- 6,475 Sq Ft
19A Darbrook Rd, Westport, CT 06880

Tucked away on a private cul-de-sac just minutes from downtown Westport, beaches, and award-winning restaurants, this 6-bedroom, 8-bath residence combines modern architectural design with serene natural surroundings. Set on beautifully landscaped grounds, the property backs onto a gentle brook, creating a peaceful, retreat-like setting. Once home to a celebrated local artist, the interiors

Nanci Lewis Keller Williams Realty

19A Darbrook Rd, Westport, CT 06880
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/36
$3,950,000
- 5 Beds
- 4 Baths
- 4,060 Sq Ft
353 Old Dam Rd, Fairfield, CT 06824

Extraordinary waterfront sanctuary offering unmatched privacy and expansive 1.5 acre property in Pine Creek Beach neighborhood. Net Zero, architecturally award-winning home stunningly designed with materials selected for visual appeal, efficiency, longevity. The striking open floorplan flows seamlessly from kitchen to living room and dining area, walls of floor to ceiling windows offer

Katie O'Grady Compass Connecticut, LLC

353 Old Dam Rd, Fairfield, CT 06824
/40
$2,999,000
- 6 Beds
- 5 Baths
- 4,640 Sq Ft
136 South Ave, New Canaan, CT 06840

Luxury In-Town Living! Discover timeless elegance and modern ease in this beautiful, fully-renovated Colonial home, just steps from the heart of downtown New Canaan. With 6 bedrooms and 5 baths (3 full and 2 half baths) across three impeccably finished levels, this home offers the perfect blend of comfort, style, and sophistication. Renovations by SOHO Group Architectural Design, completed in

Deborah Burnaman William Raveis Real Estate

136 South Ave, New Canaan, CT 06840
/35
$3,399,000
- 5 Beds
- 5.5 Baths
- 4,300 Sq Ft
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
/14
$3,485,000 Open Sun 2PM - 4PM
- 5 Beds
- 4.5 Baths
- 5,056 Sq Ft
16 Burr School Rd, Westport, CT 06880

A masterful full renovation by acclaimed Coastal Luxury Homes, this extraordinary modern residence redefines sophistication in the heart of Westport. Set on a pristine, private acre on a coveted cul-de-sac, the home dazzles with soaring ceilings, dramatic walls of glass, and exquisite luxury finishes throughout. Designed for the way you live today, it offers two primary suite options, an

Danna Rogers Higgins Group Bedford Square

16 Burr School Rd, Westport, CT 06880
/40
$3,699,000
- 5 Beds
- 4.5 Baths
- 4,856 Sq Ft
254 Penfield Rd, Fairfield, CT 06824

Rare beach area gem that checks ALL the boxes! With almost 5,000 square feet of living space on a rare and very private .43-acre lot, this highly custom home features a heated saltwater pool, spa/hot tub, 4-floor elevator, and so many high-end amenities. With an exceptionally wide footprint, this home offers 5-6 bedrooms, 4.5 bathrooms, 9-foot ceilings, front and back decks, a full-house

Ava Fisher Coldwell Banker Realty

254 Penfield Rd, Fairfield, CT 06824
/40
$2,750,000
- 5 Beds
- 4.5 Baths
- 4,198 Sq Ft
5 Ridgewood Ln, Westport, CT 06880

This modern farmhouse was praised for its remodel, receiving the HOBI Award for Outstanding Spec Home in 2017. Set on a secluded + conveniently located Old Hill cul-de-sac, the home has tremendous curb appeal w/an expansive front porch overlooking the wide front lawn. The interior finishes are remarkable, reclaimed + repurposed, the energy-efficient home uses materials such as antique woods,

Karen Scott Compass Connecticut, LLC

5 Ridgewood Ln, Westport, CT 06880
/40
$3,050,000
- 5 Beds
- 8 Baths
- 8,148 Sq Ft
125 Middlebrook Farm Rd, Wilton, CT 06897

This spectacular residence blends timeless elegance with modern sophistication, having been meticulously updated with the finest finishes throughout. Spacious yet effortlessly inviting, the home is bathed in natural light from walls of glass that frame every room. The main level is thoughtfully designed for both grand-scale entertaining and comfortable everyday living, with a seamless flow that

Leslie McElwreath Sotheby's International Realty

125 Middlebrook Farm Rd, Wilton, CT 06897
/40
$3,499,000
- 5 Beds
- 7 Baths
- 8,110 Sq Ft
4 Jennings Ct, Westport, CT 06880

Tucked away on a sought-after Westport cul-de-sac, this elegant 5-bedroom home offers the perfect blend of luxury, comfort, and convenience. Set on over an acre of beautifully landscaped property, enjoy resort-style living with a stunning gunite pool, private patio, and lush lawn-ideal for summer entertaining or peaceful relaxation. The spacious first-floor primary suite is a true retreat,

Linda Skolnick Coldwell Banker Realty

4 Jennings Ct, Westport, CT 06880
/38
$3,375,000
- 5 Beds
- 6 Baths
- 4,668 Sq Ft
91 Turkey Hill Rd S, Westport, CT 06880

Welcome to a home that lives as beautifully as it looks. In the heart of Greens Farms, this timeless 5 bedroom, 6 bath Colonial is where classic elegance meets modern ease, designed for how you live, work, and entertain today. A circular drive, stone walls, and a charming front porch create an inviting first impression. Inside, a sun-filled double-height entry sets the tone for open, gracious

Chrissie Rodriguez Higgins Group Real Estate

91 Turkey Hill Rd S, Westport, CT 06880
/39
$2,595,000
- 5 Beds
- 3 Baths
- 4,250 Sq Ft
181 Highland Ave, Norwalk, CT 06853

This architect-designed home offers approximately 4,250 square feet of living space with five bedrooms and three bathrooms. It is situated on over a half acre of flat property including a refreshing in-ground pool, an expansive patio, mature plantings and cedar fence. The first floor features a private bedroom suite with separate outdoor access, a state-of-the-art kitchen, living room with

Mary Petro Noonan Coldwell Banker Realty

181 Highland Ave, Norwalk, CT 06853
/22
$1,999,999
- 5 Beds
- 3 Baths
- 2,384 Sq Ft
12 Outer Rd, Norwalk, CT 06854

Rare mid-century modern elevated waterfront property with extraordinary views in historic Village Creek. A fabulous opportunity to restore and enhance the prized founders lot in this unique coastal community offering a marina, sandy beach, tennis courts and park--just minutes from SoNo, Rowayton, and the train to NYC. The interior of the 5 bedroom house has been demoed, and is offered with P&Z

Kristi Law William Pitt Sotheby's Int'l

12 Outer Rd, Norwalk, CT 06854
/35
$689,900 Open Sat 12PM - 3PM
- 6 Beds
- 2 Baths
- 2,441 Sq Ft
192 Scofield Ave, Bridgeport, CT 06605

An incredible investment opportunity in the highly desirable Black Rock neighborhood! This well-maintained two-unit multifamily property is perfect for investors or owner-occupants looking to generate rental income. 1st floor apartment features updated kitchen, dining room, living room, 3 bedrooms and 1 full bath. Laundry in unit. 2nd floor apartment features kitchen, dining room, 3/4 bedrooms, 1

Marissa Papa Preston Gray Real Estate

192 Scofield Ave, Bridgeport, CT 06605
/40
$449,000
- 5 Beds
- 3 Baths
- 1,108 Sq Ft
5 Staples St, Danbury, CT 06810

Surprisingly exceptional, this updated raised ranch offers the kind of quality rarely found at this price point. Meticulously maintained and pre-inspected for peace of mind, it's truly move-in ready with no hidden costs. The custom-designed kitchen features top-tier appliances and finishes typically reserved for luxury homes. Crisp white crown molding and replaced doors add a refined touch

Linda McCaffrey Coldwell Banker Realty

5 Staples St, Danbury, CT 06810
/35
$2,200,000
- 6 Beds
- 4.5 Baths
- 4,893 Sq Ft
38 Davis Hill Rd, Weston, CT 06883

Welcome to 38 Davis Hill Road, Weston - a beautifully appointed Colonial residence set on just over 2 private acres with meticulously landscaped gardens, mature plantings, and multiple patios. Designed for both relaxation and entertaining, the grounds feature a heated gunite pool with attached spa, a pool house, and exceptional outdoor living spaces. Inside, enjoy more than 4,500 sq. ft. of

Benjamin Howell Coldwell Banker Realty

38 Davis Hill Rd, Weston, CT 06883
/35
$649,000
- 5 Beds
- 3 Baths
- 2,392 Sq Ft
186 Grasmere Ave, Fairfield, CT 06824

RARE 3 FAMILY! Calling all Investors and Creative Visionaries! Great income producing opportunity. Walking distance to the Fairfield Black Rock MetroNorth train station, this solidly built 3-unit home was recently fully occupied, but is now vacant and ready for updating. Original features include hardwood flooring, porches for each unit, solid wooden doors, and a spacious full basement divided

Rita Tanis Berkshire Hathaway NE Prop.

186 Grasmere Ave, Fairfield, CT 06824
/36
$1,795,000 Open Sun 1PM - 3PM
- 6 Beds
- 4.5 Baths
- 6,015 Sq Ft
212 Fence Row Dr, Fairfield, CT 06824

Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a

Adele Higgins Higgins Group Real Estate

212 Fence Row Dr, Fairfield, CT 06824
/38
$649,900 Open Sun 12PM - 2PM
- 7 Beds
- 3 Baths
- 3,459 Sq Ft
63 Grand St, Danbury, CT 06810

Welcome to 63 Grand Street, a fully updated three-family property offering strong rental potential in the heart of Danbury. This well-maintained building features two spacious 3-bedroom units and one bright 1-bedroom unit, all vacant and move-in ready. Each apartment has been tastefully updated with modern finishes, making this property an excellent choice for investors seeking immediate income

Sean Doran William Raveis Real Estate

63 Grand St, Danbury, CT 06810
/5
$549,900
- 6 Beds
- 2 Baths
- 3,730 Sq Ft
53 Calvin Ave Unit 55, Bridgeport, CT 06604

Excellent Investment Opportunity With this Large Legal Two family Home. Great Location in the Heart of Brooklawn. Convenient to every necessity. Close to SHU, UB and Shopping. Walking into each unit a Large Foyers Unbelievable Spacious Living rooms and Dining rooms an Eat in Kitchens with large pantries. Third Level has 3 rooms with possibility of 5 rooms. Full basement, two car detached garage.

Maria Vaz Coldwell Banker Realty

53 Calvin Ave Unit 55, Bridgeport, CT 06604
/40
$725,000 Open Sun 1PM - 3PM
- 6 Beds
- 2 Baths
- 3,219 Sq Ft
592 Courtland Ave Unit 594, Bridgeport, CT 06605

Welcome to this exceptional and fully renovated two-family home in the heart of Black Rock. Ideally situated just moments from St. Mary's by the Sea, local restaurants, shops, I-95, and the Metro North train station, this property offers charm, convenience and incredible versatility. Each spacious unit features three full bedrooms. The living rooms in both units are anchored by functioning

Hillary Waite William Raveis Real Estate

592 Courtland Ave Unit 594, Bridgeport, CT 06605
/25
$2,795,000
- 5 Beds
- 3.5 Baths
- 3,800 Sq Ft
11 Orchard Place Unit B, Greenwich, CT 06830

Welcome to one of the largest townhouses in Greenwich! 11 Orchard is located in a super convenient Greenwich location; close to the train, town, and next door to the lovely Bruce Park. The main floor boasts a formal living room with fireplace, dining room, and expansive eat-in kitchen plus living room, which flows to the rear patio and yard. High end kitchen appliances and a huge island make for

Daniel Berger RE/MAX Prestige Properties

11 Orchard Place Unit B, Greenwich, CT 06830
/34
$1,749,000 Open Sat 12PM - 2PM
- 5 Beds
- 3 Baths
- 3,601 Sq Ft
108 Witch Ln, Norwalk, CT 06853

Set on a sweeping acre in Rowayton, this renovated home offers 3,601 sq. ft. of sunlit interiors, a private pool, and modern updates. A welcoming entry opens into a bright, open-concept layout with new hardwood floors throughout. The updated kitchen features a 4-seat quartz island and Bosch stainless steel appliances, flowing seamlessly into the dining area, living room, and large family room.

Kris Lippi Get Listed Realty

108 Witch Ln, Norwalk, CT 06853
/35
$9,350,000
- 7 Beds
- 10 Baths
- 9,649 Sq Ft
18 Tokeneke Trail, Darien, CT 06820

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately

Robin Stineman William Pitt Sotheby's Int'l

18 Tokeneke Trail, Darien, CT 06820
/40
$1,800,000 Open Sun 11AM - 1PM
- 5 Beds
- 4.5 Baths
- 5,645 Sq Ft
225 Good Hill Rd, Weston, CT 06883

Welcome to 225 Good Hill Road in Weston, Connecticut - a modern transitional Colonial where timeless elegance meets contemporary design. Meticulously crafted with no expense spared, this home is a masterpiece of design and craftsmanship, set on two private acres in one of Weston's most desirable neighborhoods. The kitchen is designed with bright white custom cabinetry and top-of-the-line

Judy Michaelis Coldwell Banker Realty

225 Good Hill Rd, Weston, CT 06883
/24
$499,900
- 5 Beds
- 3.5 Baths
- 1,740 Sq Ft
242 Pearl Harbor St, Bridgeport, CT 06610

Charming side- by- side brick ranch duplex, nestled on a quiet cul-de-sac. Hardwood floors throughout and a newer roof are among many updates. One unit offers 3 bedrooms, 1.5 baths. Second unit 2beds, 1 bath. Both units are very well kept and turn key. Enjoy the durability and low maintenance of brick exterior. Both units have a nice private, fenced in yard. It offers a fantastic opportunity for

Jorge Cintron Vylla Home (CT) LLC

242 Pearl Harbor St, Bridgeport, CT 06610
/39
$2,395,000 Open Sun 1PM - 3PM
- 5 Beds
- 7 Baths
- 7,336 Sq Ft
185 Sturges Ridge Rd, Wilton, CT 06897

This stately 5 BR shingle style colonial with over 7000 sf in favored Sturges Ridge neighborhood is a memory-making treasure! With a level backyard that plays host to games, gardens and gatherings including a lobster bake, birthday parties with water slides, badminton, croquet, the view to witness joyful connection is endless. The home is a haven of warmth and sophistication, and offers large

Julie Carney William Raveis Real Estate

185 Sturges Ridge Rd, Wilton, CT 06897
/37
$1,569,000 Open Sat 12PM - 2PM
- 5 Beds
- 5.5 Baths
- 3,579 Sq Ft
145 Lyons Plain Rd, Weston, CT 06883

Historic Elegance meets today's lifestyle in this 1845 Antique w/ 145' of scenic river frontage but not in the flood zone, in Lower Weston. A property rich in history, timeless charm & character is known as the Curtis Wood House. This beautifully restored & thoughtfully modernized home features 5BRS, & 4.5 baths in the main house & a legal rental cottage (480 sf included in the SF) w/ a LR,

Marilyn Heffers Coldwell Banker Realty

145 Lyons Plain Rd, Weston, CT 06883
/38
$999,999
- 5 Beds
- 4 Baths
- 4,589 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
/36
$899,000 Open Sat 12PM - 2PM
- 5 Beds
- 3.5 Baths
- 2,261 Sq Ft
73 Maitland Rd, Stamford, CT 06906

Welcome to 73 Maitland Road, a stunning 5-bedroom, 3.5-bath home in Stamford that's been completely reimagined for modern living. The main level offers two bedrooms, a brand-new kitchen with quartz countertops and soft-close cabinetry, and sliders that open to a brand-new Trex deck overlooking a private flat backyard-perfect for entertaining or relaxing. Upstairs, you'll find a spacious primary

Michael Spindler RE/MAX Right Choice

73 Maitland Rd, Stamford, CT 06906
/40
$1,999,999 Open Sat 12PM - 3PM
- 5 Beds
- 3 Baths
- 4,106 Sq Ft
215 Old Post Rd, Fairfield, CT 06824

Old Post Road perfection! Step on to the gracious front porch and be swept away by timeless architecture, graceful design and superb finishes. Beautifully renovated home with so many improvements/amenities including gorgeous expanded kitchen, renovated bathrooms, plantation shutters, new windows, new roof, fresh exterior paint, fencing and more. The inviting foyer welcomes you to a living room

Katie O'Grady Compass Connecticut, LLC

215 Old Post Rd, Fairfield, CT 06824
/40
$1,095,000
- 5 Beds
- 3.5 Baths
- 3,778 Sq Ft
51 Farview Farm Rd, Redding, CT 06896

Stately colonial home, set high on 2.04 acres with rolling level lawn in Redding's most sought after neighborhood, Farview Farms, w/private recreational association including Olympic-sized pool, tennis, clubhouse, plus hiking trails & pond for fishing/skating. Picture perfect setting w/sweeping drive, stone walls, expansive deck & mature trees. This generous home offers 3,778sf with modern open

Laura Ancona William Pitt Sotheby's Int'l

51 Farview Farm Rd, Redding, CT 06896
/30
$4,300,000 Open Sat 1PM - 4PM
- 5 Beds
- 5.5 Baths
- 5,400 Sq Ft
57 Lockwood Ave, Old Greenwich, CT 06870

This beautifully scaled five-bedroom Colonial offers refined living in one of Old Greenwich's most coveted neighborhoods, just moments from the beach, park, train, schools and dining. Set on a meticulously landscaped 1/2 acre, the 5400-square-foot sun-drenched five bedroom boasts a stone terrace, French doors, wraparound porch, butler's pantry, grand chef's kitchen with island open to the family

Noah Finz Houlihan Lawrence

57 Lockwood Ave, Old Greenwich, CT 06870
/26
$529,900 Open Sat 1PM - 3PM
- 5 Beds
- 3 Baths
- 1,700 Sq Ft
318 Center St, Bridgeport, CT 06604

Welcome to this well-maintained 2-family home with additional finished living space in the basement. This property has been thoughtfully updated and is move-in ready, making it a great option for both owner-occupants and investors. The first-floor unit offers a spacious layout with new flooring and nicely updated interiors. The second-floor unit features new flooring throughout, a renovated

Jithu Sajeevan Serhant Connecticut, LLC

318 Center St, Bridgeport, CT 06604
/39
$10,895,000
- 6 Beds
- 4.5 Baths
- 7,174 Sq Ft
17 Contentment Island Rd, Darien, CT 06820

Introducing one of Tokeneke's most iconic waterfront estates-available for the first time in 50 years. This rare and storied compound is set on 2.4 acres of exquisitely landscaped grounds with 180 feet of private shoreline along Long Island Sound. It offers an unrivaled blend of historic charm, timeless elegance, and breathtaking coastal beauty. A sweeping two-story paneled foyer leads to a

Douglas Milne Houlihan Lawrence

17 Contentment Island Rd, Darien, CT 06820
/25
$1,790,000 Open Sat 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 5,499 Sq Ft
279 E Middle Patent Rd, Greenwich, CT 06831

This exceptional 5-bedroom, 4-bath center hall colonial underwent a complete renovation in 2007 and was thoughtfully updated again in 2023. Privately set back on over 2.5 acres abutting Mianus River Park, this home offers a rare combination of tranquility and convenience, located just minutes from downtown Greenwich and under an hour to NYC. Enter through a gracious double-height foyer from the

Stacy Young William Raveis Real Estate

279 E Middle Patent Rd, Greenwich, CT 06831
/40
$1,899,000 Open Sat 1PM - 4PM
- 5 Beds
- 4.5 Baths
- 4,079 Sq Ft
68 Figlar Ave, Fairfield, CT 06824

A rare find in today's market & a stunning example of high-end new construction in the sought-after University area awaits - Welcome to 68 Figlar Avenue. This beautifully designed 5 bedroom, 4.5 bath, 11 room home offers 4 levels of living space filled w/ great light & thoughtful details. From the natural white oak flooring to the exquisite millwork & custom built-ins, craftsmanship is evident.

Jackie Davis William Raveis Real Estate

68 Figlar Ave, Fairfield, CT 06824
/38
$1,899,000 Open Sun 1PM - 3PM
- 6 Beds
- 4.5 Baths
- 4,344 Sq Ft
15 Barton Rd, Fairfield, CT 06824

Your storybook home-complete with a classic white picket fence-awaits! Where natural light fills inviting spaces, every detail is intentional, & comfort meets elegance. From quiet mornings on the sun-drenched porch to lively evenings around the large kitchen island, this home offers beauty, privacy, & seamless indoor-outdoor living. This newly finished, meticulously custom crafted, all new

Jennifer DeLaurentis Compass Connecticut, LLC

15 Barton Rd, Fairfield, CT 06824
/40
$2,150,000
- 5 Beds
- 4.5 Baths
- 4,035 Sq Ft
33 Pequot Trail, Westport, CT 06880

Welcome to 33 Pequot Trail in Westport, Connecticut. Nestled in the highly desirable Old Hill neighborhood, this timeless Colonial blends classic charm with modern living. Step inside to a bright, welcoming foyer. Clean lines, stunning hardwood floors, and natural light set the tone. The formal living room is elegant yet comfortable-a relaxing space for quiet mornings or entertaining evenings.

Judy Michaelis Coldwell Banker Realty

33 Pequot Trail, Westport, CT 06880
/39
$1,949,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 4,474 Sq Ft
31 High Ridge Rd, Fairfield, CT 06825

This new construction home is brought to you by reputable, local, HOBI award-winning builder DeLaurentis Developments. Architecturally designed & engineered w/ its beautiful lot & today's buyer in mind. This thoughtfully designed, open concept, flexible floor plan includes 5-6 bedrooms, 4.1 bathrooms, 2-car attached garage w/ wifi enabled doors & EV charging outlet, mudroom, dining room, living

Jennifer DeLaurentis Compass Connecticut, LLC

31 High Ridge Rd, Fairfield, CT 06825
/34
$12,450,000
- 5 Beds
- 7 Baths
- 8,306 Sq Ft
21 Guinea Rd, Greenwich, CT 06830

Hidden beyond a private gated drive, majestically sited atop 5.5 enchanting acres, Fox Lair reveals herself. A 1938 English manor reimagined for today, timeless architectural detail meets modern updates resulting in a home equally suited to formal entertaining or the rigors & joys of family life. The romance of a bygone era blends seamlessly with the spacious gourmet kitchen, family

Julie Grace Burke Compass Connecticut, LLC

21 Guinea Rd, Greenwich, CT 06830

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