Fairfield County CT Houses for Sale 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) 264-6802

20 Blanket Meadow Rd, Monroe, CT 06468
/2
$2,575,000 Coming Soon
- 5 Beds
- 4.5 Baths
- 7,176 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
/37
$1,390,000
- 5 Beds
- 3.5 Baths
- 2,843 Sq Ft
160 Winfield St, Norwalk, CT 06855

Welcome to 160 Winfield Street - where timeless charm meets modern comfort in this beautifully maintained home nestled in the heart of Sasqua Hills minutes from Shorehaven Country Club. Offering 5 spacious bedrooms, 3.5 updated bathrooms, and over 2,800 square feet of living space, this home is ideal for anyone seeking a charming home with modern updates in a superb location. Step inside to find

Brett Lieberman

The Riverside Realty Group

(475) 207-4460

160 Winfield St, Norwalk, CT 06855
/38
$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
/49
$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
- 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
/27
$7,195,000
- 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

79 Richmond Hill Rd, Greenwich, CT 06831
/24
$9,950,000
- 6 Beds
- 8 Baths
- 8,896 Sq Ft
35 Club Rd, Riverside, CT 06878

Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acre with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors,

Andrew Smith Houlihan Lawrence

35 Club Rd, Riverside, CT 06878
/37
$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
/36
$3,999,000
- 5 Beds
- 5 Baths
- 4,078 Sq Ft
512 North St, Greenwich, CT 06830

Welcome to 512 North Street, a meticulous colonial nestled on 2.97 manicured and private acres, south of the Merritt Parkway. As you step into this distinguished home, you are greeted by an inviting formal living room adorned with a fireplace and french doors leading to a screened-in porch that offers tranquil views of the pool. Separating the living room and kitchen is a charming den with wet

Stephen Lasko Compass Connecticut, LLC

512 North St, Greenwich, CT 06830
/39
$3,350,000
- 6 Beds
- 9 Baths
- 9,483 Sq Ft
95 Kettle Creek Rd, Weston, CT 06883

A Timeless Colonial Retreat in Lower Weston less than 10 minutes from downtown Westport, 5 minutes to the Merritt, & 3 minutes from Weston Town Center, library, & award winning Weston schools. This stunning Ralph Lauren-inspired Colonial offers classic elegance with modern luxury and entertainment, making it the dream home you've been waiting for. This 9,000 SF estate features CT stone walls &

Hannelore Kaplan William Raveis Real Estate

95 Kettle Creek Rd, Weston, CT 06883
/39
$3,995,000
- 5 Beds
- 5.5 Baths
- 5,328 Sq Ft
84 Nearwater Ln, Darien, CT 06820

Nestled on Nearwater Lane just moments from the beach, this beautifully renovated 5-bedroom/5 and a half bath home offers the perfect blend of luxury, comfort, and functionality. Step inside to discover a thoughtfully designed floor plan that flows effortlessly from room to room. The heart of the home is the stunning, fully renovated kitchen-complete with top-of-the-line appliances, sleek

Janine Tienken Houlihan Lawrence

84 Nearwater Ln, Darien, CT 06820
/37
$3,695,000
- 6 Beds
- 5.5 Baths
- 6,293 Sq Ft
176 Middlesex Rd, Darien, CT 06820

Look no further-176 Middlesex Road is the home that truly has it all. Blending timeless character with modern comfort, this exceptional 6-bedroom, 5.5-bath residence offers three full floors of living space plus a beautifully finished basement-designed for effortless entertaining and relaxed everyday living. The main level features an open-concept kitchen and living area with premium appliances,

Ashley Dineen Compass Connecticut, LLC

176 Middlesex Rd, Darien, CT 06820
/40
$3,200,000
- 6 Beds
- 9 Baths
- 9,057 Sq Ft
4 Farrell Rd, Weston, CT 06883

Welcome to this custom Connecticut Colonial defined by symmetry, stonework and sophistication. With classic lines, enduring stone walls and all the comforts of modern living, this home is an inviting and comfortable retreat. Set on a lush, private 2 acre property in desirable lower Weston, this stunning residence offers impeccably appointed living spaces and exceptional indoor-outdoor flow. This

Ellen Fusco Compass Connecticut, LLC

4 Farrell Rd, Weston, CT 06883
/38
$3,475,000
- 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
/40
$3,715,000
- 4 Beds
- 6 Baths
- 6,924 Sq Ft
291 Laurel Rd, New Canaan, CT 06840

Nestled on a serene private lane, this stunning updated colonial exudes charm and sophistication, offering a picturesque escape from the hustle and bustle of daily life. As you approach the property, you are greeted by a meticulously landscaped front yard that sets the tone for the beauty that lies within. The home features a chef's kitchen that is a culinary masterpiece, equipped with top-notch

Kerry O'Dea William Raveis Real Estate

291 Laurel Rd, New Canaan, CT 06840
/38
$3,750,000
- 6 Beds
- 7 Baths
- 7,775 Sq Ft
652 Ponus Ridge, New Canaan, CT 06840

Welcome to 652 Ponus Ridge Road, a stunning estate nestled on a quiet cul-de-sac surrounded by stone walls and a private gated entrance. This gracious home offers six spacious bedrooms featuring a pristine open kitchen with abundant natural light while, the adjacent multi-purpose prep kitchen and coffee bar serve to enhance everyday ease and entertaining. The expansive great room seamlessly

Marsha Charles Coldwell Banker Realty

652 Ponus Ridge, New Canaan, CT 06840
/40
$3,950,000
- 6 Beds
- 6.5 Baths
- 5,465 Sq Ft
208 Canoe Hill Rd, New Canaan, CT 06840

Historic New Canaan Landmark... Experience the allure of New Canaan's rich past with this extraordinary estate, originally The Waring Farm established in 1863. Enclosed by timeless New England stone walls and adorned with climbing hydrangea, the 3-acre property exudes charm from the moment you arrive. This distinguished residence masterfully blends historic elegance with modern luxury across

Janis Hennessy William Raveis Real Estate

208 Canoe Hill Rd, New Canaan, CT 06840
/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
/13
$4,500,000
- 5 Beds
- 4.5 Baths
- 3,858 Sq Ft
121 Round Hill Rd, Greenwich, CT 06831

This home was built with great bones and is now ready for a full renovation. OR, take it down and build new - see photos. Gorgeous 2.3 acres combine with a premier Round Hill Rd. address! The topography of 121 Round Hill Road offers uncommon long vistas from all floors with a unique blend of openness and privacy. Irrigated, manicured lawns, plantings, old stonewalls, and natural areas provide a

Sabine Schoenberg Primesites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/13
$3,200,000
- 4 Beds
- 5 Baths
- 3,816 Sq Ft
9 Hillside Dr, Greenwich, CT 06831

This unique home offers the best of Greenwich with a private, park like setting in the exclusive Rock Ridge Association. Originally built in 1911, the large scaled public rooms are highlighted with natural light and beautiful detail. The open foyer welcomes you to the timeless characteristics throughout the house. Updated Kitchen with breakfast nook, primary bedroom suite, and outdoor

Shelly Tretter Lynch Compass Connecticut, LLC

9 Hillside Dr, Greenwich, CT 06831
/17
$4,500,000
- 6 Beds
- 5 Baths
- 4,958 Sq Ft
121 Round Hill Rd, Greenwich, CT 06831

This home was built with great bones and is now ready for a full renovation. Or build a brand new home. Fast track with carefully considered plans or create your own on these gorgeous 2.3 acres Premier Round Hill Rd. LOCATION! See also land list.The topography of 121 Round Hill Road offers uncommon long vistas from all floors with a unique blend of openness and privacy. Irrigated,

Sabine Schoenberg PrimeSites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/39
$4,200,000
- 6 Beds
- 10 Baths
- 12,071 Sq Ft
637 Valley Rd, New Canaan, CT 06840

Showcasing the unparalleled 637 Valley Road estate, a majestic stone Georgian Colonial that offers an enchanting lifestyle along the tranquil banks of the Silvermine River. Spanning over 7.04 acres of idyllic park-like grounds, this 12,000 square foot masterpiece with a charming guest cottage is a treasure not to be missed. The estate boasts an expansive chef's kitchen, a stately home library,

JoAnne Fisher William Pitt Sotheby's Int'l

637 Valley Rd, New Canaan, CT 06840
/37
$3,750,000
- 4 Beds
- 6 Baths
- 8,912 Sq Ft
266 Great Plain Rd, Danbury, CT 06811

Welcome Home to this incredible lakefront oasis! Exclusive access to Candlewood Lake awaits you at this pristine, elegant masterpiece. Spectacular views abound from every room of the spacious, yet relaxed home. The open-concept main level includes a vaulted living room, resplendent dining room, comfortable great room with floor-to-ceiling stone fireplace, stunning office with built-ins and

Chip & Heather Neumann Houlihan Lawrence

266 Great Plain Rd, Danbury, CT 06811
/41
$3,250,000
- 6 Beds
- 8 Baths
- 6,635 Sq Ft
8 Tinker Ln, Greenwich, CT 06830

Located just 8 min. from downtown GR & tucked away at the end of a quiet cul-de-sac off of Lake Ave, this exceptional property offers privacy and space. Spanning 2.07 acres of beautiful grounds with a circular driveway, this timeless home offers 6,636SF of living space designed for both comfort and grand-scale entertaining. With 6 bedrooms, 5 full baths and 3 half baths, every detail of this

Joan Suter BHHS New England Properties

8 Tinker Ln, Greenwich, CT 06830
/40
$3,450,000
- 4 Beds
- 3.5 Baths
- 3,774 Sq Ft
40 Fairfield Beach Rd, Fairfield, CT 06824

Gorgeous coastal retreat w/ Long Island Sound views, stunning sunrises & steps to miles of sandy beaches - Welcome Home to 40 Fairfield Beach Road. An incredible location combined w/ a designer home meticulously renovated & completed in 2025. Every detail in this custom home was thoughtfully planned & executed. The homeowner spared no expense in creating a 10 room magazine worthy home. The new

Jackie Davis William Raveis Real Estate

40 Fairfield Beach Rd, Fairfield, CT 06824
/37
$4,595,000
- 5 Beds
- 8 Baths
- 6,725 Sq Ft
490 North St, Greenwich, CT 06830

Rare opportunity to own a 200 year old Barn on one mid-country acre, designed in the 70's by renowned architect Charles Gwathmey. Owners updated it to add additional bedrooms and seamlessly connect indoor and outdoor spaces offering year-round entertainment. Main entrance opens to an expansive 30 X 35' Great room filled with natural light, original beams, and impressive fireplace. A generous

Spencer Sodokoff Houlihan Lawrence

490 North St, Greenwich, CT 06830
/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
/40
$800,000
- 3 Beds
- 3.5 Baths
- 3,874 Sq Ft
7 Williams Ln, Newtown, CT 06470

Welcome to 7 Williams Lane, tucked at the end of a quiet cul-de-sac in one of Newtown's most desirable neighborhoods, this beautifully cared-for Colonial has been thoughtfully updated and maintained over the years. From the roof and windows to the mechanical systems, the work has already been done-giving you peace of mind and a move-in ready experience. Inside, the layout is both classic and

Kris Kling Around Town Real Estate LLC

7 Williams Ln, Newtown, CT 06470
/38
$950,000
- 4 Beds
- 3.5 Baths
- 3,272 Sq Ft
186 Isinglass Rd, Shelton, CT 06484

The perfect recipe for daily living includes all the simple joys - nature, relaxation, connection, ambiance and flow. With its relaxed casual vibe 186 Isinglass checks all those boxes and more. What began as a charming country cape grew to over 4,200 square feet of classic comfort. An ideal gathering place for family and friends, the heart of this home is the definition of a "great room". It's

Linda Farber RE/MAX Heritage

186 Isinglass Rd, Shelton, CT 06484
/40
$27,950,000
- 8 Beds
- 12 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
/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 & custom millwork on 4+ acres bordering the Greenwich Audubon providing privacy. The stunning new kitchen & adjacent family rm., opens to spacious outdoor living for entertaining w/expansive terraces, heated pool w/spa, outdoor BBQ, pool house w/kitchen & also a paddock with 3 stall stable. Arched doorways lead into the

Giselle Gibbs BHHS New England Properties

44 N Porchuck Rd, Greenwich, CT 06831
/10
$4,900,000
- 7 Beds
- 5.5 Baths
- 7,995 Sq Ft
37 Green Acre Ln, Westport, CT 06880

The most private and serene of the remaining multi-acre estates in central-most Westport... Just two minutes from the beach, town center, I-95, and the Saugatuck Hamlet rail station. Located Near several well-regarded school systems in Connecticut. This grand estate offers space for recreation, relaxation, and entertaining. A stone-gated, walled circular driveway marks the end of a private road

Lisa Bortz William Pitt Sotheby's Int'l

37 Green Acre Ln, Westport, CT 06880
/31
$6,900,000
- 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
/40
$2,350,000
- 5 Beds
- 4.5 Baths
- 5,445 Sq Ft
20 Silver City Rd, Newtown, CT 06470

Welcome to 20 Silver City, a truly exceptional estate offering magnificent views, total privacy, and effortless luxury. Set on 18.57 secluded acres at the end of a cul-de-sac, this sophisticated ranch-style home combines modern updates with timeless design. Step inside to discover a bright, open floor plan ideal for everyday living and entertaining. The living and dining areas flow seamlessly

Connie Widmann William Raveis Real Estate

20 Silver City Rd, Newtown, CT 06470
/40
$2,445,000
- 4 Beds
- 4.5 Baths
- 3,764 Sq Ft
16 Morningside Ln, Westport, CT 06880

Tucked away at the end of a peaceful cul-de-sac, this custom-built home offers comfortable living, an abundance of natural light throughout, & unmatched convenience, being 5 minutes from schools & Green's Farms train station. With 4 bedrooms, 4.5 bathrooms, & flexible living spaces, this home is designed for entertaining & everyday family living. A double-height foyer welcomes you with a feature

Karen Liss-uomoleale William Raveis Real Estate

16 Morningside Ln, Westport, CT 06880
/35
$1,950,000
- 4 Beds
- 3.5 Baths
- 3,173 Sq Ft
7 Apache Trail, Westport, CT 06880

Set on a picturesque cul-de-sac, this elegant Colonial offers timeless charm and modern amenities. Nestled on a level two-acre lot, the home boasts lovely curb appeal and a private, fully fenced backyard perfect for entertaining, play, and recreation. Inside, you'll find four spacious bedrooms with the option for a fifth bedroom or private home office on the main level, complete with a full bath.

Meredith Kamo Compass Connecticut, LLC

7 Apache Trail, Westport, CT 06880
/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
/40
$2,395,000
- 6 Beds
- 5.5 Baths
- 7,000 Sq Ft
3010 Redding Rd, Fairfield, CT 06824

Perched at the end of a private, tree-lined drive, this grand 5/6 bedroom, 5 full and 1 half bathroom, Georgian-style home seamlessly blends form and function. Designed to highlight the property's exquisite natural beauty, each room looks out onto lush, professionally landscaped lawns, gardens, & mature trees. Sunrises and sunsets are stunning. In every room, out every window are the most

Terry Keegan Fairfield County Real Estate

3010 Redding Rd, Fairfield, CT 06824
/39
$1,995,000
- 3 Beds
- 6 Baths
- 9,242 Sq Ft
17 Pequot Dr, Norwalk, CT 06855

Extensively updated and expanded beginning in 2012, this exceptional home blends luxury, comfort, and wellness-focused living. At the center is a remarkable 70' x 10' heated indoor lap pool, featuring advanced air filtration and heating systems for year-round enjoyment. A spa-like locker room with steam shower, double vanities, and poolside shower elevates the experience. Above the four-car

Mary Ann Lindwall The Riverside Realty Group

17 Pequot Dr, Norwalk, CT 06855

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