Fairfield County CT Homes for Sale with Private Pool

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

A Private Oasis: Discover an unparalleled opportunity at 32 Beeholm Rd, where an 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

Ellen Garcia

Brown Harris Stevens

(475) 291-4216

32 Beeholm Rd, Redding, CT 06896
/40
$1,125,000 Open Sat 12PM - 2PM
- 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
$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
$580,000 Open Sun 1PM - 3PM
- 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
/40
$359,999 Open Sun 12PM - 2PM
- 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
/39
$2,995,000
- 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
/37
$874,900
- 4 Beds
- 2.5 Baths
- 3,923 Sq Ft
32 Pine Tree Hill Rd, Newtown, CT 06470

Welcome to 32 Pine Tree Hill Road, the location of this exquisite four-bedroom, two-and-a-half-bathroom center-hall colonial. Situated on over two acres, the property provides a secluded retreat surrounded by the expansive open space of the Newtown Forest Association. Upon entering, you'll discover a two-story foyer featuring a transom window that inundates the space with natural light,

Pamela Dostilio

Coldwell Banker Realty

(475) 291-4179

32 Pine Tree Hill Rd, Newtown, CT 06470
/39
$800,000
- 2 Beds
- 3 Baths
- 1,723 Sq Ft
2 Old Kings Hwy, Norwalk, CT 06850

Located in the heart of the Silvermine Historic District, this enchanting home offers classic New England charm and a prime location just a short stroll to the acclaimed GrayBarns Inn & Tavern and the Silvermine Arts Center. This location blends heritage, culture, and natural beauty in one of Norwalk's most coveted enclaves. A light and bright spacious foyer greets you as you enter the home. With

Pam Toner

Berkshire Hathaway NE Prop.

(475) 263-4644

2 Old Kings Hwy, Norwalk, CT 06850
/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
/5
$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
/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
$1,150,000 Open Sun 12PM - 2PM
- 4 Beds
- 4.5 Baths
- 4,914 Sq Ft
26 Oak Ridge Dr, Newtown, CT 06470

Set on 3+ private acres, this remarkable Oak Ridge residence is an entertainer's delight. Outdoors, an inviting inground pool is framed by mature landscaping, masonry walls, and lawn space ideal for play or gardening, all set against a serene backdrop. An expansive deck, accessible from both the kitchen & family rm, offers the ideal spot for alfresco dining, sunsets, or celebrations. Perfect for

Elizabeth Newnham William Pitt Sotheby's Int'l

26 Oak Ridge Dr, Newtown, CT 06470
/40
$3,750,000
- 6 Beds
- 7.5 Baths
- 14,110 Sq Ft
21 Queens Grant Dr, Fairfield, CT 06824

Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

Michael Debiase Keller Williams Realty

21 Queens Grant Dr, Fairfield, CT 06824
/30
$2,490,000
- 3 Beds
- 4.5 Baths
- 6,900 Sq Ft
88 Green Ln, Ridgefield, CT 06877

Mid-Century Modern - Inspired Turnkey Connecticut Contemporary Design - influenced by the works of Frank Lloyd Wright and Philip Johnson: Including spacious indoor/outdoor living, more than 100 picture windows, skylights, and the delight of a brook that runs beneath the great room which sports 22-foot-high ceilings above -- and a see-through glass table next to the two-sided fireplace -- below.

Karen Heller Coldwell Banker Realty

88 Green Ln, Ridgefield, CT 06877
/34
$3,450,000
- 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
/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
/40
$2,495,000
- 4 Beds
- 5.5 Baths
- 3,392 Sq Ft
35 Blackberry Ln, Shelton, CT 06484

Gated estate on a private cu-de-sac with 2 driveways, park like grounds and extraordinary Reservoir views all completely fenced in. The Main house has a Gunite pool w/ a waterfall and hot tub and is surrounded by a gorgeous Limestone patio. The main house has an attached 3-car garage as well as 2-car garage attached to finished lower level. The separate Carriage House has a loft & 2 additional

Tracy Schauwecker-Perry Real Estate Two

35 Blackberry Ln, Shelton, CT 06484
/49
$5,200,000
- 6 Beds
- 9 Baths
- 7,738 Sq Ft
897 Lake Ave, Greenwich, CT 06831

Peaceful, serene and private best describes this property located on a lane off Lake Avenue adjacent conservation. Meticulously renovated with both functionality and playfulness in mind. The stunning entry foyer has soaring windows inviting in an abundance of natural light. A Bilotta designed kitchen, has custom cabinetry and high-end appliances and finishes. There is a spacious primary with

Marjorie Marianacci Coldwell Banker Realty

897 Lake Ave, Greenwich, CT 06831
/40
$2,249,000 Open Sun 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 4,343 Sq Ft
545 Shrub Oak Ln, Fairfield, CT 06824

Welcome to 545 Shrub Oak Lane, an expanded Colonial on 2 private acres in Greenfield Hill. This home sits on a beautifully flat front yard that enhances its curb appeal. Fully renovated in 2012, the family room and oversized kitchen is the heart of the home. The custom designed kitchen has an 10 foot mahogany island with granite countertops, walk-in panty, and mahogany wood framed glass doors

Christine Howard William Raveis Real Estate

545 Shrub Oak Ln, Fairfield, CT 06824
/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
/39
$3,395,000
- 5 Beds
- 4.5 Baths
- 5,442 Sq Ft
9 Milton Place, Norwalk, CT 06853

This is the one you've been waiting for in Rowayton! Walk to town with sea breezes guiding the way. Freshly painted and professionally staged, this sun-filled Colonial with many updates and in-ground pool is perfect for those who want extra room for friends and family, but offers a cozy feel when it's 'just you'! The open-concept kitchen and spacious dining area overlook the private backyard and

Julie Carney William Raveis Real Estate

9 Milton Place, Norwalk, CT 06853
/39
$6,495,000
- 6 Beds
- 8.5 Baths
- 10,942 Sq Ft
250 Carter St, New Canaan, CT 06840

Convenience & sophisticated style is what you get with this ultra-chic 6 bedroom, 8.5 bathroom masterpiece perfectly sited on a picturesque 2 flat acres with 20x40 pool and private gate entry. Built with the best finishes In mind, you'll enjoy 10ft ceilings, flexible open floor plan, private office with French doors, formal rooms that flow seamlessly from one to another, and the ultimate dream

Edward Zislis Higgins Group Real Estate

250 Carter St, New Canaan, CT 06840
/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
/40
$2,249,000
- 6 Beds
- 7.5 Baths
- 6,560 Sq Ft
85 Spring Valley Rd, Ridgefield, CT 06877

Tucked away on 6 gorgeous acres of privacy & possibility, 85 Spring Valley Rd isn't just a home - it's an experience. Whether you're hosting a crowd, escaping the city, or saddling up for a morning ride, this 6,560sf retreat was designed to live large, breathe easy & entertain beautifully. Inside, 6 en-suite BRs and 7.5 baths offer plenty of space for family & guests, each with its own private

Tim Dent Coldwell Banker Realty

85 Spring Valley Rd, Ridgefield, CT 06877
/40
$4,300,000
- 8 Beds
- 9 Baths
- 9,208 Sq Ft
88 Main St, Ridgefield, CT 06877

Welcome to one of Ridgefield's most iconic estates-a true Crown Jewel-nestled in the heart of the town's historic village and Connecticut's first designated Cultural District. Framed by stunning stone walls at the entrance, this grand estate is a masterclass in timeless elegance and modern luxury. Impeccably restored and thoughtfully reimagined, this home offers refined living space across four

Julie Setterlund William Pitt Sotheby's Int'l

88 Main St, Ridgefield, CT 06877
/37
$2,350,000
- 4 Beds
- 4.5 Baths
- 5,746 Sq Ft
27 Golden Farm Rd, Stamford, CT 06903

Welcome to your dream home, where resort-style living meets the convenience of an easy commute to NYC and Westchester County locations! Impeccably maintained and thoughtfully improved, this stunning property offers an array of features designed for both relaxation and entertainment. Head outside to your own private oasis, complete with a luxurious pool and spa, great for unwinding after a busy

Denise Taylor Coldwell Banker Realty

27 Golden Farm Rd, Stamford, CT 06903
/40
$2,650,000
- 5 Beds
- 4.5 Baths
- 3,703 Sq Ft
2821 Congress St, Fairfield, CT 06824

Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

Andrew Whiteley Brown Harris Stevens

2821 Congress St, Fairfield, CT 06824
/28
$2,500,000
- 5 Beds
- 4 Baths
- 3,772 Sq Ft
43 Buckfield Ln, Greenwich, CT 06831

Nestled at the end of a quiet street in one of the most prestigious towns in the country, this rare 8.5-acre estate in Greenwich, offers an exceptional opportunity for those seeking space, privacy, and potential. Built in 1936, this stately residence features 5 bedrooms, 4 full bathrooms, and over 3,700 square feet of living space, all set on a sprawling flat parcel rarely found in the area. The

Jolanta Rojek eXp Realty

43 Buckfield Ln, Greenwich, CT 06831
/40
$2,299,000
- 4 Beds
- 3 Baths
- 4,412 Sq Ft
8 Northfield Dr, Westport, CT 06880

This is the perfect house in the perfect location-just minutes from top-rated schools, playgrounds, ballfields, and houses of worship. Set on a picture-perfect acre of lush, manicured lawn, this Colonial style home offers serene views of a large pond while overlooking 8+ acres of private, protected meadowland. A gas-fired, whole-house generator provides seamless backup power for year-round peace

Helen Cusa Brown Harris Stevens

8 Northfield Dr, Westport, CT 06880
/40
$3,300,000
- 5 Beds
- 8 Baths
- 6,414 Sq Ft
750 Burr St, Fairfield, CT 06824

Lions Gate: No need to move to the south of France as this extraordinary residence is right here in coveted Fairfield. Enter through grand gates into a world of privacy where character, convenience, security & serenity magically meet. Magazine-worthy grounds are the soul of the estate-lush, expansive, & exquisitely curated. With a shimmering pool, spectacular California Redwood Pool House with

Julie Vanderblue Higgins Group Real Estate

750 Burr St, Fairfield, CT 06824
/40
$2,495,000
- 4 Beds
- 5 Baths
- 7,046 Sq Ft
96 Norrans Ridge Dr, Ridgefield, CT 06877

Be in before school starts! Timeless Elegance Minutes from Downtown Ridgefield. As you enter the property, you're immediately welcomed by refined elegance and serene privacy, just minutes from the heart of Ridgefield's vibrant downtown. This meticulously maintained residence is a true showcase of luxury, craftsmanship, and thoughtful design. As you enter the grand foyer the newly refinished

Jay Contessa William Pitt Sotheby's Int'l

96 Norrans Ridge Dr, Ridgefield, CT 06877
/39
$2,749,000
- 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
$2,575,000
- 6 Beds
- 4.5 Baths
- 5,083 Sq Ft
4 the Fenway, Westport, CT 06880

Timeless elegance in Westport's prestigious Old Hill. First time on the market in 29 years! This expansive 5-6 bedroom, 4.5 bath farmhouse is gracefully set on 2.22 serene acres, featuring a heated gunite pool, picturesque pond, and a very rare blend of privacy and proximity to town. The sun-drenched primary suite is a true retreat with a fireplace, spa-like bath, and generous walk-in closet. A

Mary Kate Klemish-Boehm Brown Harris Stevens

4 the Fenway, Westport, CT 06880
/40
$3,450,000
- 5 Beds
- 5 Baths
- 3,561 Sq Ft
6 Over Rock Ln, Westport, CT 06880

Welcome to 6 Over Rock Lane - a stunning 1920s colonial retreat in the heart of Westport, Connecticut blending timeless New England charm with sophisticated modern living. A unique move-in opportunity with curated designer furniture offered. Set on a quiet, luxurious street in one of Westport's most desirable neighborhoods, this property offers peace, privacy, and proximity - just minutes from

Judy Michaelis Coldwell Banker Realty

6 Over Rock Ln, Westport, CT 06880
/40
$2,895,000 Open Sun 1PM - 3PM
- 4 Beds
- 4.5 Baths
- 4,643 Sq Ft
44 Scofield Farms, Darien, CT 06820

Nestled at the end of a serene cul-de-sac is a 4-acre sanctuary where luxury and enchantment intertwine. Designed for the ultimate entertainer, the heated pool, complete with a swim-up bar, invites endless summer soirees under the stars, while the adjacent outdoor kitchen transforms every gathering into a culinary spectacle. A full tennis court and full basketball court promises spirited matches

Melissa Engel Douglas Elliman of Connecticut

44 Scofield Farms, Darien, CT 06820

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