Fairfield County CT Homes for Sale with Pool

/38
$3,525,000
- 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
/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
$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
/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
/38
$4,500,000
- 5 Beds
- 4.5 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
/40
$4,395,000
- 4 Beds
- 7 Baths
- 4,650 Sq Ft
72 Shorefront Park, Norwalk, CT 06854

Welcome to 72 Shorefront Park-a recently built waterfront FEMA compliant masterpiece by renowned CJT Builders, where luxury and lifestyle meet in perfect harmony. Thoughtfully designed with the finest finishes and exceptional attention to detail, this elegant residence features 4 spacious bedrooms, 4 full en suite baths, and 3 half baths. Take in sweeping water views from nearly every room, or

Peter Stuart Houlihan Lawrence

72 Shorefront Park, Norwalk, CT 06854
/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
/27
$2,550,000
- 2 Beds
- 2.5 Baths
- 1,760 Sq Ft
41 Richmondville Ave Unit Duplex 2, Westport, CT 06880

This impressive home has floor-to-ceiling windows, wood floors and a linear gas fireplace. The kitchen has an oversized island, high-end appliances, and is complete with custom cabinetry. The 2 bedrooms are on opposites sides of the home for maximum privacy. The primary suite has a generous walk-in closet and a luxurious windowed bathroom with rain shower, dual sinks, and heated floors. Stairs

Ashlei De Souza Serhant Connecticut LLC

41 Richmondville Ave Unit Duplex 2, 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
$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
/39
$1,849,000
- 3 Beds
- 6 Baths
- 9,242 Sq Ft
17 Pequot Dr, Norwalk, CT 06855

New Price! Now $1,849,000 - Incredible Value for This One-of-a-Kind Wellness Retreat Near Shorehaven Golf Club Extensively updated and expanded since 2012, this custom residence offers a unique blend of luxury, comfort, and wellness-focused living. At its heart is a spectacular 70' x 10' indoor heated lap pool, complete with advanced air filtration and climate control systems-perfect for

Mary Ann Lindwall The Riverside Realty Group

17 Pequot Dr, Norwalk, CT 06855
/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
/29
$1,650,000
- 4 Beds
- 3.5 Baths
- 3,942 Sq Ft
18 Cardinal Rd, Weston, CT 06883

Tucked away on a quiet cul-de-sac in sought-after Lower Weston, this extraordinary 4-bedroom retreat redefines modern leisure living. With unrivaled privacy and every amenity at your fingertips, each day feels like a vacation in your very own resort-style oasis. Step inside to discover sun-drenched, open-concept living spaces-perfect for family life and effortless entertaining. Expansive windows

Peter Depalo William Raveis Real Estate

18 Cardinal Rd, 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
/34
$489,900
- 3 Beds
- 3.5 Baths
- 2,822 Sq Ft
14 Kingswood Dr, Bethel, CT 06801

Bethel's Best-Kept Secret! Welcome to Kingswood - a charming, small-town complex that offers all the amenities of larger communities without the crowds. With only 89 units, you'll never have to compete for space at the pool or tennis courts. Enjoy the on-site playground and create lasting memories. This beautifully designed 3-bedroom, 3.5-bathroom townhouse offers the perfect blend of modern

Kari Rustici Coldwell Banker Realty

14 Kingswood Dr, Bethel, CT 06801
/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
/33
$365,000
- 2 Beds
- 2 Baths
- 1,196 Sq Ft
97 Richards Ave Unit AA7, Norwalk, CT 06854

Welcome to this bright and beautifully maintained ranch-style condo, ideally situated in the heart of West Norwalk! Boasting 1,196 square feet of comfortable living space, this move-in ready home features 2 spacious bedrooms and 2 full bathrooms. The open-concept layout is enhanced by gleaming hardwood floors, creating a warm and inviting ambiance throughout. The well-appointed kitchen includes

Kenneth Zerella II William Raveis Real Estate

97 Richards Ave Unit AA7, Norwalk, CT 06854
/40
$2,995,000
- 4 Beds
- 4.5 Baths
- 10,636 Sq Ft
22 Nature Ln, Shelton, CT 06484

CROWN JEWEL OF FAIRFIELD COUNTY! Spectacular custom-built mansion offering nearly 11,000 sq ft (Grand Total 12,228) of exquisite craftsmanship & architectural elegance, brilliant landscaping, pristine 1.5 acre level lot within an exclusive enclave w/ breathtaking water views! This estate features 4 spacious Bedrooms & 4.5 luxurious Bathrooms. Gated entrance & circular driveway lead to impressive

Kate Mattox Higgins Group Real Estate

22 Nature Ln, Shelton, CT 06484
/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
/15
$384,500
- Land
- 10 Acres
- $40,010 per Acre
4,10,12 River Oaks Ln, Sherman, CT 06784

Exceptional opportunity to purchase a 3-lot package totaling 9.62 acres in the prestigious gated community of The Club at River Oaks in Sherman, CT. This private enclave features 66 home sites spread across 350 acres, centered around an 18-hole, par-70 golf course that flows naturally through the Berkshire foothills. The three lots-4 River Oaks Lane (3.12 acres) 10 River Oaks Lane(3.07 acres),

David Landau RE/MAX Right Choice

4,10,12 River Oaks Ln, Sherman, CT 06784
/64
$43,000,000
- 6 Beds
- 11 Baths
- 11,500 Sq Ft
579 Indian Field Rd, Greenwich, CT 06830

This stunning 2.72 acre waterfront property in Mead Point has panoramic South and Easterly views across the Sound to Long Island, New York and to Tods Point and Riverside. Enjoy sunrises from almost every room in this custom-built stone and shingle colonial. The current owners intention to preserve the original house, was not possible, and they built new with the goal of retaining old world

Heather Platt Sotheby's International Realty

579 Indian Field Rd, Greenwich, CT 06830
/40
$25,000,000
- 6 Beds
- 11 Baths
- 19,569 Sq Ft
1131 Sasco Hill Rd, Fairfield, CT 06824

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

1131 Sasco Hill Rd, Fairfield, CT 06824
/26
$1,350,000
- 4 Beds
- 3.5 Baths
- 7,232 Sq Ft
40 Old Bridge Rd, Brookfield, CT 06804

Celebrate summer in style in this meticulously crafted, custom-built home. Impeccably well maintained with beautiful hardwood floors, exquisite custom woodwork and 9 ft ceilings that add a touch of style to every room. The versatile floor plan seamlessly guides you from the spacious entry, past the formal living room and through the oversized dining room, into the heart of the home - a center

Patricia Guarantano William Pitt Sotheby's Int'l

40 Old Bridge Rd, Brookfield, CT 06804
/46
$17,500,000
- 7 Beds
- 13 Baths
- 16,597 Sq Ft
11 Conyers Farm Dr, Greenwich, CT 06831

Breathtaking lake, waterfall and nature views enhance this architecturally sundrenched Colonial with unrivaled amenities on 19.69 private acres-best location in Conyers Farm. On the market for the 1st time, this custom designed Home by architect Robert Lamb Hart takes full advantage of the beautiful setting with walls of windows overlooking the lake in a stunning open floor plan. Easy access to

Anne Ward Houlihan Lawrence

11 Conyers Farm Dr, Greenwich, CT 06831
/9
$11,900,000
- 6 Beds
- 9 Baths
- 9,836 Sq Ft
32 Pheasant Ln, Greenwich, CT 06830

Welcome to 32 Pheasant Lane, a stunning completely rebuilt and expanded modern Colonial on one of Greenwich's most coveted streets. This exceptional 6 bedroom, 7.2 bath home offers over 9800 square feet of luxurious finished living space on 4 levels. An expansive front porch invites you inside where you will discover an open, airy floor plan with 10ft ceilings and custom details. White oak floors

Maria Crowley Houlihan Lawrence

32 Pheasant Ln, Greenwich, CT 06830
/39
$1,999,000
- 4 Beds
- 4.5 Baths
- 5,427 Sq Ft
5 Stone Wall Ln, Sherman, CT 06784

Introducing an unparalleled residence crafted by a luxury builder as their sanctuary in Southern Sherman, where every detail reflects quality and design. Step into a foyer that leads to an expansive open-concept living area. The space features vaulted 12-foot ceilings adorned with craftsman trim work. Natural light bathes it, highlighting the rich maple hardwood floors and a striking

Trish McFadden Houlihan Lawrence

5 Stone Wall Ln, Sherman, CT 06784
/36
$10,995,000
- 7 Beds
- 11 Baths
- 16,008 Sq Ft
358 Lukes Wood Rd, New Canaan, CT 06840

This exquisite 7 bedroom & 11 bath colonial residence & compound set on 4.78 acres offers old world aesthetics with modern artistry. The craftsmanship of the millwork, finishes and features is unparalleled including reclaimed oak flooring imported from France and Hope's custom designed steel windows and doors. The harmonious transition between interior and outdoors is facilitated by numerous

Jennifer Crowley Douglas Elliman of Connecticut

358 Lukes Wood Rd, New Canaan, CT 06840
/75
$13,750,000
- 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
/20
$1,995,000
- 4 Beds
- 3 Baths
- 3,284 Sq Ft
297 Cognewaugh Rd, Cos Cob, CT 06807

Nestled within the serene beauty of Greenwich's sought-after Cos Cob community, this elegant property is set on two private, wooded acres. This refined 4-bedroom, 3-bathroom residence spans over 3,200 square feet of meticulously designed living space, perfect for the discerning buyer.Exquisite hardwood floors, sunlit interiors, and architectural details create an atmosphere of understated

Mark Pruner Compass Connecticut, LLC

297 Cognewaugh Rd, Cos Cob, CT 06807
/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
/17
$900,000
- 4 Beds
- 3.5 Baths
- 1,680 Sq Ft
5 Brentwood Cir Unit 5, Danbury, CT 06810

Don't miss this stunning original model home-loaded with high-end upgrades and ready to impress! This sought-after end unit features a beautifully expanded kitchen with an extra 8 feet of custom cabinetry and elegant under-cabinet lighting-perfect for both entertaining and everyday living. You'll love the luxurious, top-of-the-line flooring throughout, and the sleek, modern conveniences including

Marvin and Laura Beninson Keller Williams Realty

5 Brentwood Cir Unit 5, Danbury, CT 06810
/13
$224,900
- 1 Bed
- 1 Bath
- 672 Sq Ft
4 Heather Ridge Unit 4, Shelton, CT 06484

Light and Bright one bedroom end unit with wood floors. Living room with sliders to covered deck. Updated eat-in kitchen with newer appliances. Oversized primary bedroom with walk-in closet. Updated bathroom, common laundry room on premises, plenty of open parking, Convenient commuter location, close to RT8, RT15 and I-95. The HOA also has a lovely pool.

Edain Connery Coldwell Banker Realty

4 Heather Ridge Unit 4, Shelton, CT 06484
/31
$8,950,000
- 6 Beds
- 5.5 Baths
- 5,040 Sq Ft
33 Meadow Wood Dr, Greenwich, CT 06830

In the gated Quarry Farm neighborhood of the enchanting Belle Haven Association with 24hr security, this property offers a unique opportunity to renovate or build new, 16,000+ sq ft waterfront home. Overlooking Byram Harbor and Long Island Sound, the current 6-bedroom house sits on 2.78 acres with a pool, adjacent to a 1.09-acre protected lot. Once a quarry and later acquired as part of the

Joseph Barbieri Sotheby's International Realty

33 Meadow Wood Dr, Greenwich, CT 06830
/40
$12,400,000
- 12 Beds
- 16 Baths
- 18,000 Sq Ft
544 Oenoke Ridge, New Canaan, CT 06840

A rare opportunity to own a legacy estate that would command over $50 million to recreate in today's market. Orchard's End, built in 1929 designed by New York architect William B. Tubby, his outstanding designs include Waveny House in New Canaan, Dunnellen Hall in Greenwich and the William H. Childs House in Brooklyn. Beginning in 2014, the current owners retained world renowned architect Dinyar

Danielle Scialpi-Malloy Serhant Connecticut, LLC

544 Oenoke Ridge, New Canaan, CT 06840
/23
$33,000,000
- 8 Beds
- 14 Baths
- 18,954 Sq Ft
555 Lake Ave, Greenwich, CT 06830

Overlooking 8+park-like acres, this majestic brick Georgian was transformed to blend top of the line appointments with a rich array of custom detailing. Crowned by a 3-story chandelier, the impressive reception hall with Wenge walnut parquetry floor opens to a formal Dining Room with fireplace and elegant Living Room with fireplace and custom bar. Distinguished two-story English mahogany library

Leslie McElwreath Sotheby's International Realty

555 Lake Ave, Greenwich, CT 06830
/40
$4,375,000
- 6 Beds
- 11 Baths
- 10,414 Sq Ft
5 Boxwood Ln, Westport, CT 06880

Refined living awaits on Boxwood Lane, a prime Hunt Club cul-de-sac featuring tranquil private entrances to stately colonial style homes. From its cobblestone-lined, semi-circular driveway to the backyard pool and bluestone patio oasis, the grounds of 5 Boxwood Lane are simply spectacular. The home itself stands apart, meticulously designed with exquisite details and custom amenities. Four

Karen Scott Compass Connecticut, LLC

5 Boxwood Ln, Westport, CT 06880
/39
$5,000,000
- 4 Beds
- 7 Baths
- 6,625 Sq Ft
155 Long Ridge Rd, Danbury, CT 06810

ROADSIDE - A Storied 53-Acre Private Estate in Fairfield County CT Escape to your own private nature retreat at ROADSIDE, a rare 53-acre country estate just 90 minutes from Manhattan. This legacy property blends historic charm with modern luxury in a setting that feels worlds away-yet is 1.5M from the Redding train station and the cultural vibrancy of Fairfield County. Set within a fully fenced,

Kathleen Harrison Coldwell Banker Realty

155 Long Ridge Rd, Danbury, CT 06810
/47
$25,000,000
- 6 Beds
- 12 Baths
- 12,312 Sq Ft
24 Conyers Farm Dr, Greenwich, CT 06831

In one of the most beautiful settings in the exclusive Conyers Farm Association, this stately, ivy-clad stone manor is majestically sited overlooking 25 rolling acres. Long southern views extend over 2 lots, with exquisite formal gardens, an inviting pool and putting green. Recently renovated with impeccable taste, the gracefully scaled 12,312 sq ft floorplan offers 6 bedrooms and 6 baths.

Joseph Barbieri Sotheby's International Realty

24 Conyers Farm Dr, Greenwich, CT 06831

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