Fairfield County CT Houses for Sale with Private Pool

/40
$995,000
- 7 Beds
- 4 Baths
- 3,167 Sq Ft
29 Priscilla Rd, Norwalk, CT 06850

Location, Location!! Beautiful big house in the heart of Norwalk, 7-Beds, 4-Baths, 2 spacious garages. Don't miss the opportunity to live just 40min from NYC. Close to MCC. Vacancy subject to owner finding a suitable home within the next 60 days

Miguel Jaraba Marquez

Whitestone Real Estate Group

(203) 769-9354

29 Priscilla Rd, Norwalk, CT 06850
/53
$4,995,000
- 4 Beds
- 6 Baths
- 5,244 Sq Ft
34 Edgewood Dr, Greenwich, CT 06831

Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, masterfully renovated in 2025 this Colonial offers a harmonious blend of heritage architecture and sophisticated modernity. Designed to accommodate both grand-scale entertaining and intimate daily living, the residence unfolds across three levels and over 7,000 square feet of meticulously curated

Danielle Malloy

Serhant Connecticut LLC

(203) 769-9185

34 Edgewood Dr, Greenwich, CT 06831
/40
$2,250,000
- 5 Beds
- 4 Baths
- 2,452 Sq Ft
32 Beeholm Rd, Redding, CT 06896

Your exceptional 24+ acre private oasis awaits. This significant piece of Redding's natural beauty offers more than just a home; it includes two charming rustic cottages, adding an impressive 1,023 sq. ft. (#A) and 982 sq. ft. (#B) of versatile living space. Each cottage features 1 bedroom and 1 bath, providing ideal accommodations for guests, extended family, caretakers, or a steady revenue

Ellen Garcia

Brown Harris Stevens

(475) 291-4216

32 Beeholm Rd, Redding, CT 06896
/27
$675,000
- 2 Beds
- 4 Baths
- 1,776 Sq Ft
5 Gingham Ct Unit 5, Danbury, CT 06810

Welcome to 5 Gingham Court in Danbury, a beautifully maintained condo built in 2019 offering 2 bedrooms, 2 full bathrooms, and over 1,700 square feet of modern living space in the sought after Rivington Community. This home features a spacious open layout with pristine finishes, and versatile areas perfect for a home office or guest space. Enjoy the convenience of an attached garage, a private

Adam Wagner

Keller Williams Prestige Prop.

(203) 802-6473

5 Gingham Ct Unit 5, Danbury, CT 06810
/34
$750,000
- 4 Beds
- 2.5 Baths
- 3,587 Sq Ft
45 Ball Pond Rd, New Fairfield, CT 06812

Welcome to this beautiful West Side 4-bedroom center-hall colonial in desirable New Fairfield. Set back from the road, the home makes a great first impression with lighted stone pillars and a nearly level driveway. Inside, a wide foyer opens to a spacious living room and connects seamlessly to the formal dining room-ideal for gatherings. The kitchen is both functional and inviting, with ample

Jean Flynn

Luks Realty

(475) 267-2684

45 Ball Pond Rd, New Fairfield, CT 06812
/40
$749,000
- 3 Beds
- 2 Baths
- 2,612 Sq Ft
102 Hanover Rd, Newtown, CT 06470

Three Bedrooms and Two full Baths Contemporary Cape. With an open floor plan, a large Family Room with a Wood stove, a Sun Room, and a screened-in Hot Tub room. The kitchen has granite countertops and stainless steel appliances. The main level has a split A/C heating unit and skylights throughout. Outside with an above-ground pool and abundant Nature. An oversized deck that steps down to a patio

Edmundo DaSilva

eXp Realty

(203) 590-9796

102 Hanover Rd, Newtown, CT 06470
/40
$4,650,000
- 3 Beds
- 3 Baths
- 2,650 Sq Ft
34 Shorehaven Rd, Norwalk, CT 06855

Exclusive Waterfront Retreat in Gated Island Community - Just One Hour from NYC. Welcome to a rare opportunity to own one of only twelve homes on a secluded private island on the Long Island Sound. This 3-bedroom, 3-bathroom waterfront home offers the perfect escape from city life while remaining effortlessly connected to the best of Fairfield County. Perched between the sparkling waters of Long

Toni Mickiewicz

William Pitt Sotheby's Int'l

(475) 405-1946

34 Shorehaven Rd, Norwalk, CT 06855
/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 Malloy

Serhant Connecticut, LLC

(475) 445-2580

544 Oenoke Ridge, New Canaan, CT 06840
/25
$3,999,000
- 6 Beds
- 8 Baths
- 6,000 Sq Ft
57 Evergreen Ave, Westport, CT 06880

Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

Hyleri Katzenberg

Compass Connecticut, LLC

(475) 253-3404

57 Evergreen Ave, Westport, CT 06880
/40
$525,000
- 3 Beds
- 1.5 Baths
- 1,480 Sq Ft
50 Hortense St, Stratford, CT 06614

Make this beautiful three-bed 1.5 bath colonial nestled on a quiet dead-end street that exudes character inside and out your new home. Inside, the spacious eat-in kitchen features sufficient cabinetry and stainless steel appliances. The sliders off the dining area lead to the level backyard. The half bath and laundry room, which features a washer/dryer, are located on the main level. Upstairs are

Rudolph Perkins

Coldwell Banker Realty

(475) 253-3283

50 Hortense St, Stratford, CT 06614
/27
$6,250,000 Open Sun 11AM - 1PM
- 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

(203) 601-7487

79 Richmond Hill Rd, Greenwich, CT 06831
/40
$359,999
- 3 Beds
- 2 Baths
- 1,360 Sq Ft
98 Boston Terrace, Bridgeport, CT 06610

Located just minutes from Edison Elementary, this beautifully renovated 3-bedroom, 2-bathroom home blends modern updates with timeless charm. Step inside and immediately feel at home with rich hardwood floors, recessed lighting, and an inviting, open layout. The kitchen is designed to impress, featuring granite countertops, stainless steel Samsung appliances, and generous counter space perfect

Mike Albert

RE/MAX RISE

(475) 335-8321

98 Boston Terrace, Bridgeport, CT 06610
/40
$2,995,000 Open Sun 1PM - 3PM
- 5 Beds
- 5.5 Baths
- 5,965 Sq Ft
2015 Redding Rd, Fairfield, CT 06824

Majestically sited on 2 private acres of professionally landscaped grounds, this exceptional SMART modern farmhouse surpasses new construction standards with uncompromising attention to detail. This 5,500+ SF estate exemplifies architectural integrity with handcrafted millwork and bespoke finishes throughout. Superior craftsmanship shines in every detail-from rich white oak hardwood floors to

Susan Lieberman

The Riverside Realty Group

(475) 252-9450

2015 Redding Rd, Fairfield, CT 06824
/5
$4,895,000 New Construction
- 6 Beds
- 9 Baths
- 9,224 Sq Ft
21 Warnock Dr, Westport, CT 06880

Expected for completion Fall 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
/40
$995,000
- 5 Beds
- 4 Baths
- 3,652 Sq Ft
55 Mimosa Ct, Ridgefield, CT 06877

Welcome to Mimosa Estates, one of Ridgefield's most desirable neighborhoods just minutes from the vibrant town center with its shops, restaurants, cultural venues, and theaters. Residents here enjoy incredible community amenities, including a pool, tennis and basketball courts, a clubhouse, a playground, and sports fields-all just steps from home. This spacious residence is privately situated on

Chip & Heather Neumann Houlihan Lawrence

55 Mimosa Ct, Ridgefield, CT 06877
/40
$3,999,999
- 5 Beds
- 9 Baths
- 11,450 Sq Ft
64 Old Redding Rd, Weston, CT 06883

Discover a stunning custom-crafted luxury home, complete with a separate one-bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished. Nestled on meticulously landscaped grounds with picturesque views of Pawtucket Valley Country Club, this grand colonial residence offers every amenity for a refined lifestyle. As you enter the soaring foyer, you are

Anissa Paolillo Redfin Corporation

64 Old Redding Rd, Weston, CT 06883
/7
$2,090,000
- 5 Beds
- 7 Baths
- 5,100 Sq Ft
0 Mountain Rd, Wilton, CT 06897

This proven luxury home builder wants to build your future dream home on this rarely available one of a kind private lot. Drive down a private, hidden 1000+ foot driveway to find a property totaling over 2.00+ acres of unmatched and untouched exclusivity surrounded by protected state land. Add pool and tennis too! Two amazing potential lot sites. In addition, and even a possibility of

Evan Sheftel Millstone Real Estate Corp

0 Mountain Rd, Wilton, CT 06897
/40
$6,450,000
- 5 Beds
- 4.5 Baths
- 4,791 Sq Ft
22 Apple Tree Trail, Westport, CT 06880

Take advantage of this final opportunity to secure this newly reduced price on a stunning residence where coastal living meets modern luxury. Just two blocks from Compo Beach, this brand-new 4,791 sq. ft. home sits on a quiet private road on .37 acres. Combining timeless elegance with a move-in-ready lifestyle, this home features soaring 9+ ft ceilings, white oak floors, and custom Italian

Deborah Aulfinger Gold & Home Realty

22 Apple Tree Trail, Westport, CT 06880
/37
$1,895,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 5,474 Sq Ft
5 New England Dr, Stamford, CT 06903

Welcome to 5 New England Drive-a spacious and thoughtfully designed ranch set on a level one-acre corner lot in North Stamford, offering the rare advantage of natural gas and public water. The beautifully maintained grounds provide a true retreat with a tennis court, in-ground pool, courtyard, covered outdoor dining area with pizza oven, and a fully fenced backyard. Inside, you'll find 5,474 sq

Stephen Lasko Compass Connecticut, LLC

5 New England Dr, Stamford, CT 06903
/40
$3,795,000 Open Sun 12PM - 3PM
- 4 Beds
- 6 Baths
- 6,704 Sq Ft
5 Sail Harbour Dr, Sherman, CT 06784

Grand FULLY FURNISHED 6,700 SF Mediterranean, direct waterfront on two seriously private acres in Sail Harbor Club. Entertainer's paradise offers unlimited possibilities. Dramatic NEW 26x13 Sun Room displays exciting wall of glass that overlooks NEW 36x14 porcelain tiled deck above sprawling NEW 39x21 covered porcelain tiled patio. NEW 90' deck surrounds 45' saltwater gunite pool having its own

Paul Valeri Paul Valeri, Realtors

5 Sail Harbour Dr, Sherman, CT 06784
/25
$3,495,000
- 5 Beds
- 4.5 Baths
- 4,670 Sq Ft
49 Sumner Rd, Greenwich, CT 06831

Step into a world of light and space as soaring ceilings and expansive windows welcome you into this tastefully renovated home, nestled on a quiet cul-de-sac in Greenwich's coveted back country. Set on four lush acres, this residence offers privacy, elegance, and effortless indoor-outdoor living. The dramatic vaulted entryway leads to a gracious living room anchored by a cozy fireplace, and a

Leslie McElwreath Sotheby's International Realty

49 Sumner Rd, Greenwich, CT 06831
/27
$4,475,000 Open Sat 1PM - 3PM
- 5 Beds
- 5.5 Baths
- 6,135 Sq Ft
261 Hollow Tree Ridge Rd, Darien, CT 06820

This charming 5-bedroom Cape Cod home is the perfect blend of classic elegance and modern comfort. Nestled in a highly sought-after neighborhood, the property offers spacious living with timeless details throughout. From the moment you step inside, you're greeted by beautiful hardwood floors, crown molding, and fireplaces that enhance the inviting atmosphere of the living spaces. The large,

Catherine Russell Brown Harris Stevens

261 Hollow Tree Ridge Rd, Darien, CT 06820
/31
$3,799,000 Open Sun 1PM - 3PM
- 6 Beds
- 6.5 Baths
- 7,899 Sq Ft
3 Bolton Ln, Westport, CT 06880

This beautiful home with undeniable curb appeal crafted by Andy Frank, sits on a flat, centrally located acre in the heart of Westport. Designed with light-filled spaces and an open, eat in kitchen, the home is finished across 4 levels, offering versatile living for today's lifestyle. Enjoy 6 bedrooms, sun drenched interiors, private home office, and a walk-out lower level perfect for recreation

Jen Kass Higgins Group Bedford Square

3 Bolton Ln, Westport, CT 06880
/21
$3,000,000 Open Sun 1PM - 3PM
- 4 Beds
- 3.5 Baths
- 3,978 Sq Ft
5 Wooddale Rd, Greenwich, CT 06830

New to market. This mid-century 4 bedroom & 3 1/2 bath home sits on an oversized 2.23-acre lot in a sought-after cul-de-sac off Lake Avenue, in a 2-acre zone. The sun-drenched, open floor plan spans 4,000 sq ft, with a true walk-out finished lower level overlooking the private, lush grounds. Whether you're looking to renovate/expand or build your dream home, this meticulously maintained property

Ellen Mosher Houlihan Lawrence

5 Wooddale Rd, Greenwich, CT 06830
/38
$4,000,000
- 5 Beds
- 6.5 Baths
- 5,789 Sq Ft
221 Greens Farms Rd, Westport, CT 06880

THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb antique homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and

Leslie Riback Coldwell Banker Realty

221 Greens Farms Rd, Westport, CT 06880
/62
$6,395,000
- 6 Beds
- 4.5 Baths
- 4,629 Sq Ft
508 Round Hill Rd, Greenwich, CT 06831

Welcome to this stunning Round Hill estate in Greenwich, Connecticut, set in a private, knoll-top setting that ensures tranquility and picturesque views. This exquisite property spans four glorious acres and features six spacious bedrooms and four and a half baths, providing ample room for family and guests. Enjoy beautiful east and west exposures that fill the home with natural light. The

Stephen Archino Sotheby's International Realty

508 Round Hill Rd, Greenwich, CT 06831
/40
$3,500,000 Open Sat 12PM - 3PM
- 6 Beds
- 9 Baths
- 9,597 Sq Ft
9 Banks Dr, Weston, CT 06883

Exceptional Jack Franzen designed shingle style estate offering 9,000+ sq. ft. of refined living space on a private cul-de-sac in bucolic Weston. Nestled on 6.5+ acres abutting 33 acres of protected land, this rare property also includes a separate 3+ acre buildable lot-perfect for future expansion, a family compound, or simply to enjoy lasting privacy. The timeless layout showcases formal living

Julie Vanderblue Higgins Group Real Estate

9 Banks Dr, Weston, CT 06883
/39
$2,850,000 Open Sat 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 6,144 Sq Ft
650 Laurel Rd, New Canaan, CT 06840

Through stone columns along a scenic approach is this first time on market custom-built five bedroom brick house on four private acres. Spacious rooms with 10ft ceilings and detailed mill work on the main floor include a cathedral height family room with dramatic fireplace, a front-to-back living room, a wood paneled office, and a four-season sun room to enjoy the stunning property. The large

Leslie Razook William Pitt Sotheby's Int'l

650 Laurel Rd, New Canaan, CT 06840
/40
$2,850,000
- 3 Beds
- 3.5 Baths
- 4,643 Sq Ft
5060 Main St, Stratford, CT 06614

Welcome to this stunning waterfront retreat on the scenic Housatonic River, offering panoramic views, luxury, and comfort. Perfect for relaxing or entertaining, this home features 3 spacious bedrooms, 3.5 baths, and a finish able bonus room above the 2-car garage-ideal for a guest suite or office. Elevator to all three levels provides added convenience. A stone wall and gated entry lead to a

Karen Cross William Raveis Real Estate

5060 Main St, Stratford, CT 06614
/36
$2,495,000 Open Sat 12PM - 2PM
- 5 Beds
- 3 Baths
- 3,072 Sq Ft
56 Charcoal Hill Rd, Westport, CT 06880

A rare offering, this remarkable Frazier Peters stone home is a masterful blend of historic character and timeless elegance, set impressively at the top of Charcoal Hill on 2.3 breathtaking acres of fully-gated privacy. Obsessively maintained and reimagined by the current owners, the home was designed with Peters' signature use of native stone, rich wood, and artisan detail, making the residence

Cyd Hamer William Pitt Sotheby's Int'l

56 Charcoal Hill Rd, Westport, CT 06880
/40
$3,649,000 Open Sun 2PM - 4PM
- 5 Beds
- 4.5 Baths
- 6,607 Sq Ft
2683 Bronson Rd, Fairfield, CT 06824

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate offers a rare opportunity in one of Fairfield's most coveted locations. Set on more than two acres of beautifully landscaped grounds with distant views of Long Island Sound, the property reflects timeless elegance and a sense of place that is hard to replicate today. Across from a distinguished

Tara Hawley Coldwell Banker Realty

2683 Bronson Rd, Fairfield, CT 06824
/23
$2,995,000 Open Sun 1PM - 3PM
- 3 Beds
- 3 Baths
- 2,882 Sq Ft
267 Riversville Rd, Greenwich, CT 06831

Nestled at the end of a quiet dead -end street, this 3- bedroom, 3- bath, home offers a rare blend of privacy and possibility. Surrounded by a peaceful setting, the property provides an excellent canvas for updates and customization, allowing the creation of something truly special. This open and airy home has a flexible floor plan and a primary bedroom with easy access to a private pool and

Barbara Zaccagnini Coldwell Banker Realty

267 Riversville Rd, Greenwich, CT 06831
/27
$3,695,000
- 6 Beds
- 7 Baths
- 5,510 Sq Ft
2 Webb Rd, Westport, CT 06880

NEW CONSTRUCTION with Pool, on a quiet cul-de-sac, in a neighborhood that is great for walking/biking in central Westport. Walk to Post Rd shops/restaurants, Winslow Dog Park, even Main St, Library, and the Levitt Pavilion! 6 bedrooms/5 full baths/ 2 half baths. 4 finished floors of living space. Gunite Pool w/Automatic Safety Cover and Room for Cabana. HUGE, FLAT, FENCED IN YARD for

Lori Popkin Coldwell Banker Realty

2 Webb Rd, Westport, CT 06880
/39
$2,499,000
- 4 Beds
- 6 Baths
- 3,726 Sq Ft
634 S Benson Rd, Fairfield, CT 06824

From the moment you arrive, you are captivated w/ blooming gardens & privacy trees that create an inviting curb appeal that welcomes you in. Architecturally gorgeous w/ brilliant craftmanship, this coastal home is a rare find in the Beach neighborhood. Featuring 4 spacious en-suite bedrooms, 12 rooms, 3 levels & an elevator servicing all floors, this home sets a new standard for exceptional

Jackie Davis William Raveis Real Estate

634 S Benson Rd, Fairfield, CT 06824
/40
$2,395,000
- 3 Beds
- 4.5 Baths
- 7,136 Sq Ft
88 Green Ln, Ridgefield, CT 06877

Architecturally significant modern home, influenced by the works of Frank Lloyd Wright & Philip Johnson, nestled privately on 2 acres at the end of a cul de sac in sought after West Mountain Estates w/recreational assoc. for pool, tennis, basketball, ball fields, pavillion & neighborhood social events. This true work of art is the result of a $2M+ gut renovation & expansion of the original home,

Laura Ancona William Pitt Sotheby's Int'l

88 Green Ln, Ridgefield, CT 06877
/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
/40
$2,849,000
- 4 Beds
- 4.5 Baths
- 3,530 Sq Ft
800 Rowland Rd, Fairfield, CT 06824

Enjoy life just 44 steps from a private beach path in this completely renovated coastal home, where every detail has been designed for year-round enjoyment. Featuring a sparkling pool, custom outdoor firepit, and spa with panoramic water and Penfield Lighthouse views, this property offers the ultimate blend of luxury and relaxation - all within walking distance to the heart of Fairfield's shops,

Carrie Sakey Coldwell Banker Realty

800 Rowland Rd, Fairfield, CT 06824
/40
$3,200,000
- 4 Beds
- 6 Baths
- 6,000 Sq Ft
29 Goodsell Hill Rd, Redding, CT 06896

Exceptional custom-built home by top tier builder - Fletcher Custom Homes and designed by acclaimed architect Chris Pagliaro with interiors by Mark Finley. Sophistication and architectural details at every turn. The Main Level impresses with soaring ceilings, radiant heated floors, and walls of glass. An impressive Chef's Kitchen features 2" waterfall island tops and a stunning glass wine wall

Karla Murtaugh Compass Connecticut, LLC

29 Goodsell Hill Rd, Redding, CT 06896
/40
$2,995,000 Open Sun 2PM - 4PM
- 5 Beds
- 6 Baths
- 4,142 Sq Ft
40 Hermit Ln, Westport, CT 06880

Set on more than two acres of exquisite, park-like property in the coveted Red Coat estate section of Westport, this spectacular modern home with a glorious gunite pool offers an ideal lifestyle. A designer's own residence, this home showcases uncompromising quality with intuitive features. The landscaped approach begins with a large stone parking court that accommodates entertaining on a grand

Alex Chingas Coldwell Banker Realty

40 Hermit Ln, Westport, CT 06880
/39
$3,250,000
- 6 Beds
- 7.5 Baths
- 14,110 Sq Ft
21 Queens Grant Dr, Fairfield, CT 06824

There are houses you tour, and then there are estates that capture your imagination. This extraordinary Greenfield Hill Colonial is the latter-a 9,700+ sq. ft. residence set on a pristine 2-acre corner lot in one of Fairfield's most prestigious neighborhoods. A paver-stone drive winds past manicured gardens to a grand two-story entry with a sweeping staircase, setting the tone for elegant living.

Elizabeth Tritschler William Raveis Real Estate

21 Queens Grant Dr, Fairfield, CT 06824

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