5-Bedroom Homes for Sale in Fairfield County CT with Private Pool

/38
$1,450,000
- 5 Beds
- 3.5 Baths
- 5,044 Sq Ft
20 Blanket Meadow Rd, Monroe, CT 06468

Welcome to 20 Blanket Meadow Rd. This stunning custom-built Colonial sits on nearly 2.5 flat acres in one of Monroe's most desirable neighborhoods, offering over 5,000 sq.ft. across three levels. The main level features an expansive open-concept kitchen with solid wood cabinetry, granite countertops, a gas range, and double ovens, seamlessly flowing into the family room where you'll be welcomed

Terri Tournas

Coldwell Banker Realty

(475) 271-1784

20 Blanket Meadow Rd, Monroe, CT 06468
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/39
$2,575,000
- 5 Beds
- 4.5 Baths
- 10,139 Sq Ft
194 Long Close Rd, Stamford, CT 06902

An unparalleled beauty, this European Chateau was custom built with the finest materials. As you pass through the stone pillars of 194 Long Close Rd, you are immediately impressed by its park-like manicured grounds.The Spanish imported brick exterior & new Cedar shingle roof accentuates the beauty of these grounds. Entering the two-story foyer you are enveloped in opulence with the marble floors,

Terri Tournas

Coldwell Banker Realty

(475) 271-1607

194 Long Close Rd, Stamford, CT 06902
/27
$6,950,000
- 6 Beds
- 8 Baths
- 7,447 Sq Ft
79 Richmond Hill Rd, Greenwich, CT 06831

Completely renovated exquisitely designed Colonial-style home, nestled on 4 park-like acres. Custom millwork, built-ins, designer lighting, and European fixtures. Light-filled family dining area featuring a 20-foot curved sliding glass wall that opens to the patio and pool. The Primary Suite boasts private balcony, large dressing room, and luxurious bath complete with radiant heated floors,

Kevin Stone

Sotheby's International Realty

(475) 255-6696

79 Richmond Hill Rd, Greenwich, CT 06831
/2
$4,895,000 New Construction
- 6 Beds
- 9 Baths
- 9,224 Sq Ft
21 Warnock Dr, Westport, CT 06880

Expected for completion end of summer 2025, this striking architectural design meets refined luxury in a meticulously crafted 9,200+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern

Brett Lieberman

The Riverside Realty Group

(475) 255-6647

21 Warnock Dr, Westport, CT 06880
/38
$7,250,000
- 5 Beds
- 6 Baths
- 6,714 Sq Ft
21 Aiken Rd, Greenwich, CT 06831

Introducing a timeless Round Hill estate, on the market for the first time in over 50 years. Nestled midway along a quiet cul-de-sac, this pastoral property spans over 10 sweeping, private acres, overlooks a tranquil pond, and offers access to riding trails. The main residence features beautifully proportioned, sun-filled rooms, 5 bedrooms, 4 full and 2 half baths, and a walk-out lower level that

Krissy Blake Sotheby's International Realty

21 Aiken Rd, Greenwich, CT 06831
/37
$5,200,000
- 6 Beds
- 9 Baths
- 5,816 Sq Ft
427 Taconic Rd, Greenwich, CT 06831

Neighboring Greenwich's most significant equestrian property, this peerless estate sits less than one short mile from the Banksville shopping center where the acclaimed gourmet & coffee shop entices locals to linger and chat. A 3-story entry is flooded with natural light from the glass dome above, and open plan living flows seamlessly. Formal living & dining rooms give way to the kitchen/great

Julie Grace Burke Compass Connecticut, LLC

427 Taconic Rd, Greenwich, CT 06831
/40
$6,195,000
- 6 Beds
- 7 Baths
- 7,336 Sq Ft
945 Oenoke Ridge, New Canaan, CT 06840

Set on over five private acres along New Canaan's coveted Oenoke Ridge, this extraordinary estate is a reimagined 1890s cow barn masterfully transformed by the Hobbs family with architects Joeb Moore and Louise Brooks. Blending agrarian charm with refined modern design, the residence honors its heritage while offering sophisticated comfort. A tree-lined drive and landscape lighting set a

Danielle Scialpi-Malloy Serhant Connecticut, LLC

945 Oenoke Ridge, New Canaan, CT 06840
/38
$6,300,000
- 9 Beds
- 7 Baths
- 6,841 Sq Ft
78 Khakum Wood Rd, Greenwich, CT 06831

Remarkably, 78 Khakum Wood has been treasured by only 2 owners. Built in 1906, this was the first structure in the private community envisioned by Newton Phelps Stokes in collaboration with the esteemed landscape firm of Olmstead Brothers. Sited on 2.95 acres , this was the original gate house for the Stokes estate serving as the stables, the kennels and staff living quarters. The unique Tudor

Deborah Huffard Houlihan Lawrence

78 Khakum Wood Rd, Greenwich, CT 06831
/39
$4,999,000
- 5 Beds
- 3.5 Baths
- 6,172 Sq Ft
21 Oak Ridge Park, Westport, CT 06880

Centrally located in the heart of Saugatuck. An unexpected hidden oasis awaits you! The setting is nothing short of magical, nestled amid lush greenery with panoramic views of the Saugatuck River and neighboring parkland. South and southwest facing, the home is bathed in natural light throughout the day and offers stunning sunsets. Whether you're lounging poolside or relaxing indoors, the

Tanya Sprague William Raveis Real Estate

21 Oak Ridge Park, Westport, CT 06880
/36
$8,750,000
- 5 Beds
- 8 Baths
- 8,744 Sq Ft
170 John St, Greenwich, CT 06831

BELLE HILL FARM. Reminiscent of the great country estates of Normandy. Long drive through manicured grounds to circle surrounding a majestic Sargent's Weeping Hemlock. Absolutely breathtaking grounds with specimen trees & manicured gardens. Impressive Brick & Stucco European Manor, circa 1942. Spectacular restoration & addition using the finest materials. Rooms of perfect proportion with

Daniel Ginnel Ginnel Real Estate

170 John St, Greenwich, CT 06831
/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
/40
$4,995,000
- 5 Beds
- 6 Baths
- 8,004 Sq Ft
3113 Bronson Rd, Fairfield, CT 06824

Nestled in the heart of historic Greenfield Hill, just steps from the iconic town green, this timeless 1840 Colonial has been meticulously restored and thoughtfully expanded to meet the needs of today's discerning buyer. With a provenance that includes architectural contributions by Cameron Clark (1930s) and Jim Thompson (2004), this home is a blend of historic integrity and modern elegance. Set

Andrew Whiteley Brown Harris Stevens

3113 Bronson Rd, Fairfield, CT 06824
/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
/35
$5,100,000
- 5 Beds
- 5 Baths
- 5,704 Sq Ft
59 Hillside Rd, Greenwich, CT 06830

Exceptional opportunity to own a turnkey Colonial on 1.5 park-like acres just moments from town. Throughout the light-filled interiors, refined formal details blend seamlessly with modern upgrades throughout. A chef's kitchen opens to a family room with fireplace. A fabulous recent addition offers a spacious office, family room, bedroom suite, and mudroom. French doors lead to an expansive

Krissy Blake Sotheby's International Realty

59 Hillside Rd, Greenwich, CT 06830
/39
$4,295,000 Open Sat 1PM - 3PM
- 5 Beds
- 6 Baths
- 6,388 Sq Ft
1580 Ponus Ridge, New Canaan, CT 06840

California meets New Canaan in this William Wurster inspired transitional-style masterpiece set on 2.54 private acres on New Canaan's desirable west side that's so convenient to town. This extensively renovated home has over 100 custom windows and 16 doors bringing the outside in from every room. Amazing sun-drenched living space with wonderful views from EVERYWHERE. French doors lead to

Kelly Defrancesco William Raveis Real Estate

1580 Ponus Ridge, New Canaan, CT 06840
/55
$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
$5,495,000
- 6 Beds
- 9 Baths
- 9,620 Sq Ft
17 Wardwell Dr, New Canaan, CT 06840

UNDERSTATED GRANDEUR. UNFORGETTABLE LIVING. At the end of a quiet New Canaan cul-de-sac stands a rare blend of timeless elegance and modern livability. Architect-designed and set amidst landscape architect-crafted gardens, this stone and shingle estate is grand yet understated with every inch reflecting thoughtful design & refined materials. The gracious foyer leads to a sunlit living room,

Rita Kirby William Pitt Sotheby's Int'l

17 Wardwell Dr, New Canaan, CT 06840
/40
$4,900,000
- 6 Beds
- 12 Baths
- 13,979 Sq Ft
2959 Congress St, Fairfield, CT 06824

Prepare to be wowed by this extraordinary estate featuring six bedrooms and ten-and-a-half bathrooms, spanning four meticulously designed floors. Enter through a breathtaking two-story grand foyer, leading into beautifully appointed formal and informal rooms perfect for entertaining and a gourmet kitchen that any discerning chef would envy. The luxurious primary suite serves as a private

Anissa Paolillo Redfin Corporation

2959 Congress St, Fairfield, CT 06824
/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
/40
$4,500,000 Open Sun 12PM - 2PM
- 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
/40
$4,800,000 Open Sun 12PM - 2PM
- 7 Beds
- 8 Baths
- 7,259 Sq Ft
104 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. Refined modern

Doug Bross Coldwell Banker Realty

104 Compo Rd S, Westport, CT 06880
/40
$5,950,000
- 6 Beds
- 9 Baths
- 12,139 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
/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
/45
$5,500,000
- 5 Beds
- 6 Baths
- 5,012 Sq Ft
50 North St, Greenwich, CT 06830

Nestled in the heart of Greenwich, this romantic 1905 Victorian home sits on an oversized .94 acre flat lot with mature trees. High ceilings, expansive rooms & private terraces exude timeless elegance. This spacious home features 5 bedrooms, 5 1/2 bathrooms & two-car garage with port cochere. The sports court, pool, & spacious pool house welcome you home for a relaxing day. Enjoy your front

Danielle Claroni Sotheby's International Realty

50 North St, Greenwich, CT 06830
/61
$5,595,000
- 6 Beds
- 8 Baths
- 5,634 Sq Ft
44 N Porchuck Rd, Greenwich, CT 06831

Elegantly renovated 6 bed, 6.2 bath Georgian Colonial w/stunning finishes on 4+ acres bordering the Fairchild Wildflower Sanctuary providing privacy. The stunning new kitchen & adjacent family rm., opens to spacious outdoor living for entertaining w/expansive terraces, heated pool w/spa, BBQ, pool house w/kitchen & a paddock w/3 stall stable. Arched doorways lead into the living rm., formal

Giselle Gibbs BHHS New England Properties

44 N Porchuck Rd, Greenwich, CT 06831
/24
$4,900,000
- 7 Beds
- 5.5 Baths
- 7,995 Sq Ft
37 Green Acre Ln, Westport, CT 06880

Enjoy the best of Westport lifestyle at this elegant 4.4-acre private estate. The property is two minutes from the beach, town center, I-95, and the Saugatuck Hamlet rail station. This classic 1936 gracious ~8,000 Sq/Ft residence includes 7 bedrooms and 5.1 baths, four grand fireplaces, a former ballroom, an antique stone-and-beamed family room, and a gourmet kitchen with professional appliances

Lisa Bortz William Pitt Sotheby's Int'l

37 Green Acre Ln, Westport, CT 06880
/34
$5,595,000
- 5 Beds
- 5 Baths
- 3,231 Sq Ft
477 Lake Ave, Greenwich, CT 06830

Seize the opportunity to own a rare piece of Greenwich's prestigious ''Golden Triangle.'' This exceptional 2.83-acre property, available for the first time since 1988, is a true gem, offering a private, level, and beautifully landscaped lot. With town water, gas, and sewer already in place, this is an unparalleled find. This 1962 classic brick and clapboard home spans 3,231 sq. ft. of refined

Stephen Archino Sotheby's International Realty

477 Lake Ave, Greenwich, CT 06830
/30
$5,200,000
- 6 Beds
- 7.5 Baths
- 9,630 Sq Ft
355 Greens Farms Rd, Westport, CT 06880

Exceptional Gated Estate in Greens Farms! Welcome to 355 Greens Farms Rd, a spectacular 2.25 acres estate designed for luxurious living and ultimate entertaining. This stunning home is a dream for car enthusiasts, featuring a four-car garage with room for lifts, making it perfect for showcasing and maintaining your collection. Step inside to find a brand-new kitchen and a newly designed primary

Meredith Cohen Serhant Connecticut, LLC

355 Greens Farms Rd, Westport, CT 06880
/42
$4,750,000
- 7 Beds
- 7 Baths
- 7,139 Sq Ft
69 Taconic Rd, Greenwich, CT 06831

A true home connoisseur's dream! Renovated and spectacular Mid-century modern home! This home offers a RARE opportunity positioned to attract positive energy, from the harmonizing nature embracing the home, via walls of glass, as well as exquisite top line physical features like SS appliances and designer bath finishes. Positioned on over 4 serene acres, yet minutes to the train station.

Tina Angelos BHHS New England Properties

69 Taconic Rd, Greenwich, CT 06831
/50
$14,250,000
- 6 Beds
- 8 Baths
- 9,418 Sq Ft
52 Carriglea Dr, Riverside, CT 06878

Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

Stephen Archino Sotheby's International Realty

52 Carriglea Dr, Riverside, CT 06878
/40
$1,930,000
- 7 Beds
- 10 Baths
- 5,883 Sq Ft
49 Great Ring Rd, Sandy Hook, CT 06482

Welcome to 49 Great Ring Road-an iconic estate with breathtaking views and a classic 1940 built home full of charm and elegance. Step into the front-to-back foyer and take in the sight lines to the expansive stone patio and sparkling pool. At the heart of the home is the great room, featuring a soaring ceiling and a grand fireplace-perfect for gatherings. The custom cherry sunroom is a

Connie Widmann William Raveis Real Estate

49 Great Ring Rd, Sandy Hook, CT 06482
/40
$2,300,000 Open Thu 11:30AM - 2PM
- 6 Beds
- 4.5 Baths
- 4,471 Sq Ft
7 Sherwood Farms, Westport, CT 06880

Set in Greens Farms on the premier "Sherwood Farms" cul-de-sac of upscale homes with an Association pool and clubhouse, this Nantucket Shingle-style residence designed by prominent architect, Roger Ferris, is in excellent, move-in condition. Meticulously maintained, this 6-bedroom home offers thoughtful updates throughout the spacious floor plan. The gracious interior begins with a soaring

Alex Chingas Coldwell Banker Realty

7 Sherwood Farms, Westport, CT 06880
/40
$875,000
- 5 Beds
- 3 Baths
- 3,524 Sq Ft
99 Bouton St W, Stamford, CT 06907

Welcome to 99 Bouton Street West, one of Stamford's most popular neighborhoods - Springdale. A beautiful level grassy yard w/ In-ground pool, Pool House, patio, garden area & huge driveway. Originally a Cape Cod style home w/ additions making it a true Colonial Cape. A versatile floor plan offers numerous possibilities - 5 bedrooms is perfect for the large family, maybe a possible 1st floor

Tony Matteis Jr. AJM Real Estate Services, Inc.

99 Bouton St W, Stamford, CT 06907
/38
$2,995,000 Open Sun 1PM - 3PM
- 5 Beds
- 6 Baths
- 5,348 Sq Ft
4 Echo Dr, Darien, CT 06820

Welcome home to this fabulous like new construction home on a sought after street in Darien. Incredible updates and high end finishes will blow you away including light fixtures and window treatments throughout. Opportunity awaits to live in this amazing 5348 SF center hall colonial with gorgeous Wagner pool! Flow is everything here at 4 Echo Drive. Sun drenched rooms flow into the next with

Keiley Fuller Compass Connecticut, LLC

4 Echo Dr, Darien, CT 06820
/40
$1,479,000
- 6 Beds
- 3.5 Baths
- 6,074 Sq Ft
13 Sugar St, Newtown, CT 06470

Welcome to one of Newtown's most iconic homes-where timeless elegance meets unforgettable charm. Built in 1888 by New York City railroad director I.B. Harris and his wife Jane Glover Harris, a proud Newtown native and descendant of one of the town's founding families, this grand Victorian masterpiece is a living piece of local history. The home's stunning three-story tower with curved glass

Christine Fairchild Coldwell Banker Realty

13 Sugar St, Newtown, CT 06470
/40
$3,500,000
- 5 Beds
- 7 Baths
- 7,498 Sq Ft
67 Peaceable St, Ridgefield, CT 06877

Beautifully sited down a private lane is a Premier In-Town Estate with timeless elegance offering breathtaking views of Ward Acres Farms. This exceptional Nantucket Shingle Style Home sits on 4.04 acres of natural beauty. This stunning residence features 5 spacious Bedrooms, 5 full Bathrooms & 2 Half Baths. Hardwood floors flowing throughout, custom millwork & detailing. The Main Level boasts

Karla Murtaugh Compass Connecticut, LLC

67 Peaceable St, Ridgefield, CT 06877
/40
$2,475,000
- 7 Beds
- 7.5 Baths
- 6,519 Sq Ft
15 Arrowhead Way, Weston, CT 06883

Welcome to 15 Arrowhead Way, a contemporary gem located just minutes from Westport's vibrant Main Street in the serene charm of Lower Weston, CT. This 3-story home is nestled at the end of a quiet cul-de-sac, offering both privacy & convenience. With quick access to top rated schools & the Merritt Parkway, this property boasts an expansive back & side lawn featuring a pool & a pickleball/tennis

Karen Hagen Compass Connecticut, LLC

15 Arrowhead Way, Weston, CT 06883
/37
$2,750,000 Open Sat 12PM - 2PM
- 5 Beds
- 5.5 Baths
- 8,612 Sq Ft
127 Easton Rd, Westport, CT 06880

This custom-built Colonial set along the Aspetuck River offers stunning curb appeal, privacy, serene surroundings, and thoughtfully designed spaces for both everyday living and elegant entertaining. Step into a dramatic foyer followed by light-filled interiors with soaring ceilings and oversized transom windows. The main level features both formal living and dining rooms with gas fireplaces, an

Polly Sykes Compass Connecticut, LLC

127 Easton Rd, Westport, CT 06880
/40
$3,750,000 Open Sat 1PM - 4PM
- 6 Beds
- 8 Baths
- 7,300 Sq Ft
971 Hulls Farm Rd, Southport, CT 06890

Tucked behind gates on two lush, private acres in Southport, this exceptional residence-featured in Fairfield Magazine-offers the ultimate blend of luxury, comfort, and convenience. Built by renowned Tallman Segerson builders, the transitional Georgian colonial was thoughtfully designed to evoke the feeling of a weekend retreat every day. Once a serene apple orchard, the property has been

Elizabeth Tritschler William Raveis Real Estate

971 Hulls Farm Rd, Southport, CT 06890
/45
$19,900,000
- 6 Beds
- 11 Baths
- 11,500 Sq Ft
11 Round Hill Club Rd, Greenwich, CT 06831

Spectacular custom limestone manor house situated on prestigious Round Hill Club Rd. Set on a prime, level, 3 acre parcel in the heart of sought after mid-country Greenwich. Meticulously landscaped and gated property is an extremely private, park-like oasis. Extensive list of many upgrades available upon request - including tennis court, pool house, finished lower level plus much more. Pear tree

Robert Johnson Brown Harris Stevens CT, LLC

11 Round Hill Club Rd, Greenwich, CT 06831

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5-Bedroom Homes for Sale in Fairfield County CT with Private Pool

5-Bedroom Homes for Sale with Private Pool in Fairfield County, CT

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