Homes for Sale in Fairfield County CT with 5-Bedrooms & a Private Pool

/31
$6,495,000
- 5 Beds
- 9 Baths
- 13,474 Sq Ft
386 North St, Greenwich, CT 06830

This magnificent 9,974 sq ft estate seamlessly blends grand scale, craftsmanship, and modern luxury following an extensive 2025-2026 renovation. Set on 2.3 parklike acres in coveted Mid-Country Greenwich, just minutes from town, the home makes an immediate impression with a soaring two-story foyer introducing exquisitely appointed interiors defined by custom details and rich materials. Completed

Jennifer Leahy Compass Connecticut, LLC

386 North St, Greenwich, CT 06830
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/30
$7,250,000
- 5 Beds
- 4.5 Baths
- 4,423 Sq Ft
16 Juniper Rd, Norwalk, CT 06853

Masterpiece in Rowayton. Originally designed by legendary architect Bruce Beinfield, this exceptional home was expanded by its current owners, who merged two properties to create one of Rowayton's truly one-of-a-kind residences. Pool. Yard. Privacy. Just steps from the beach and a short stroll to town. Tucked behind 30-foot evergreen hedges lies a true sanctuary: a 35-foot gunite pool, outdoor

Amanda Spatola Houlihan Lawrence

16 Juniper Rd, Norwalk, CT 06853
/40
$3,495,000
- 5 Beds
- 8 Baths
- 9,032 Sq Ft
253 Rivergate Dr, Wilton, CT 06897

Handsomely set on two private, resort-like acres, this timeless Nantucket-style residence offers the feel of a secluded family compound. Adjacent to a 21-acre wildlife preserve along the west bank of the Saugatuck River, the setting invites fishing by the river and peaceful walks along scenic trails through the surrounding natural landscape. Custom built by celebrated architect Tim Geitz, the

Michelle Genovesi William Raveis Real Estate

253 Rivergate Dr, Wilton, CT 06897
/37
$5,350,000
- 5 Beds
- 8 Baths
- 8,035 Sq Ft
473 Hollow Tree Ridge Rd, Darien, CT 06820

Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom

Ellen Mccue Houlihan Lawrence

473 Hollow Tree Ridge Rd, Darien, CT 06820
/39
$5,995,000
- 5 Beds
- 7 Baths
- 7,039 Sq Ft
1 Bramble Ln, Riverside, CT 06878

Exceptional custom built 5 bedroom stone and shingle home in a sought-after Riverside location. Across from Riverside school/playground and one block to Eastern Middle School, this beautifully designed and professionally decorated home showcases a two-story foyer, well proportioned and light-filled living spaces, high ceilings, exceptional finishes and craftsmanship. Spacious chef's kitchen has

Barbara Wells Houlihan Lawrence

1 Bramble Ln, Riverside, CT 06878
/40
$3,950,000
- 5 Beds
- 9 Baths
- 7,040 Sq Ft
44 Pumpkin Hill Rd, Westport, CT 06880

Set in one of Westport's most sought-after central neighborhoods, this gracious 5+ bedroom custom Colonial with a stunning gunite pool and spa offers the perfect balance of timeless elegance and modern comfort. Sun-filled interiors and thoughtful design create seamless flow for both entertaining and everyday living. The main level features a private office, elegant dining room with butler's

Christine Oleynick Keller Williams Realty

44 Pumpkin Hill Rd, Westport, CT 06880
/40
$15,945,000
- 6 Beds
- 10 Baths
- 11,211 Sq Ft
30 Meadowcroft Ln, Greenwich, CT 06830

Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold

Jeffrey Jackson Corcoran Centric Realty

30 Meadowcroft Ln, Greenwich, CT 06830
/38
$899,900
- 5 Beds
- 2.5 Baths
- 3,659 Sq Ft
34 Lindencrest Dr, Danbury, CT 06811

Absolutely stunning 5-bedroom, 2.5-bath Colonial offering over 3,600 sq ft on 1.23 acres in a sought-after neighborhood. A welcoming entry showcases beautiful hardwood floors throughout. The spacious living room flows seamlessly into the dining room, ideal for entertaining. The remodeled kitchen features granite countertops, stainless steel appliances, abundant cabinetry, a center island, and a

Tracey Precourt Century 21 Clemens Group

34 Lindencrest Dr, Danbury, CT 06811
/40
$3,000,000
- 6 Beds
- 5.5 Baths
- 5,952 Sq Ft
70 Meadow Ridge Rd, Fairfield, CT 06824

Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept

David Krasnoff Compass Connecticut, LLC

70 Meadow Ridge Rd, Fairfield, CT 06824
/40
$6,790,000
- 7 Beds
- 9 Baths
- 14,066 Sq Ft
4 Cowdray Park Dr, Greenwich, CT 06831

Situated within the gated enclave of Conyers Farm in backcountry Greenwich, this elegant French Chateau embodies architectural distinction, privacy, and resort-style living. Here, heritage and pastoral elegance converge, framed by rolling polo grounds, preserved countryside, and an atmosphere defined by quiet exclusivity. Set gracefully on more than 13 acres, comprised of mature woodlands, and

Vickie Kelley Camelot Real Estate

4 Cowdray Park Dr, Greenwich, CT 06831
/40
$1,925,000
- 6 Beds
- 4.5 Baths
- 5,998 Sq Ft
14 Merlins Ln, Newtown, CT 06470

Welcome to 14 Merlins Refined Luxury, Smart Living, Exceptional Privacy. Fully renovated with exceptional attention to detail inside and out. This true 6 bedroom 4 full bath home is simply exceptional. The grand foyer impresses with an 18 foot ceiling, Palladian window, and marble checkerboard floors. The new chefs kitchen is a standout with Wolf wall ovens, Wolf range with gas and induction

Connie Widmann William Raveis Real Estate

14 Merlins Ln, Newtown, CT 06470
/40
$1,990,000
- 5 Beds
- 4.5 Baths
- 4,665 Sq Ft
1209 Westover Rd, Stamford, CT 06902

Extraordinary opportunity. A gracious country estate in the highly sought-after Westover neighborhood, set on a stately and private property with mature gardens, in-ground pool, fountain and large patio ideal for outdoor entertaining. This custom built 5-bedroom, 5-bath home blends classic architecture with subtle European designer influences throughout. Meticulous care devoted to upgrade this

Catherine Aaron Berkshire Hathaway NE Prop.

1209 Westover Rd, Stamford, CT 06902
/26
$7,995,000
- 5 Beds
- 7.5 Baths
- 10,981 Sq Ft
38 Partridge Hollow Rd, Greenwich, CT 06831

Set on 8 private acres in one of Greenwich's most prestigious enclaves, 38 Partridge Hollow Road offers luxury and tranquility. This five-bedroom, 7.5-bath home blends timeless elegance with modern sophistication, featuring a first-floor primary suite with dual baths, separate closets, and access to a private office and gym. Bright, sunlit interiors and a chef's kitchen flow into inviting living

Brittany Baity Compass Connecticut, LLC

38 Partridge Hollow Rd, Greenwich, CT 06831
/40
$3,595,000
- 5 Beds
- 4.5 Baths
- 5,300 Sq Ft
245 Benedict Hill Rd, New Canaan, CT 06840

A storybook entrance framed by classic stone walls opens to four flat, park-like acres leads you to this thoughtfully updated five-bedroom Colonial layered with warmth, character, and the kind of detail that make a house feel instantly welcoming. The light filled chef's kitchen flowing seamlessly into a family room with fireplace and French doors open to the terrace, heated pool, spa, and paddle

Melissa Jones Houlihan Lawrence

245 Benedict Hill Rd, New Canaan, CT 06840
/37
$8,895,000
- 8 Beds
- 10 Baths
- 8,391 Sq Ft
212 Bedford Rd, Greenwich, CT 06831

Step into the reimagined 'Sunset Farm,' where historic charm meets modern luxury. Originally a Dutch Colonial from 1840, this landmarked property was completely rebuilt in 2006, blending timeless craftsmanship with contemporary elegance. The grand living and dining rooms, showcasing custom moldings and bespoke details, are perfect for entertaining, while the spacious chef's kitchen flows into a

Yashmin Lloyds Compass Connecticut, LLC

212 Bedford Rd, Greenwich, CT 06831
/40
$1,100,000
- 5 Beds
- 4 Baths
- 4,473 Sq Ft
13 Surrey Ln, Monroe, CT 06468

13 Surrey Lane * 5 Bedrooms * 3,283 Sq Ft * 1.57 Acres * Cul-de-Sac Setting * Main-Level Bedroom * Quartz Kitchen * Wood-Burning Fireplace * City Water & Sewer Set on 1.57 private acres at the end of a cul-de-sac in Monroe, Connecticut, 13 Surrey Lane offers 3,283 square feet of refined living space across three finished levels. Built in 2000, this five-bedroom colonial blends classic

Darwin Montenegro BHHS Darien/New Canaan

13 Surrey Ln, Monroe, CT 06468
/35
$7,750,000
- 6 Beds
- 10 Baths
- 15,399 Sq Ft
119 Proprietors Crossing, New Canaan, CT 06840

119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere.

Molly Rubins NestSeekers International

119 Proprietors Crossing, New Canaan, CT 06840
/40
$2,575,000
- 6 Beds
- 4.5 Baths
- 5,083 Sq Ft
4 the Fenway, Westport, CT 06880

Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled

Mary Kate Klemish-Boehm Brown Harris Stevens

4 the Fenway, Westport, CT 06880
/37
$24,900,000
- 7 Beds
- 8 Baths
- 18,217 Sq Ft
44 & 40 Mayo Ave, Greenwich, CT 06830

Nestled within the prestigious Belle Haven, Fairholme Estate is a magnificent English Manor that exudes timeless elegance and grandeur. Set on 2.74 beautifully landscaped acres, this seven-bedroom masterpiece features a spectacular pool, gracious wraparound porch, formal gardens, and expansive lawns, complemented by a charming coachman's cottage. Meticulously preserved to honor its historic

Joanne Mancuso Houlihan Lawrence

44 & 40 Mayo Ave, Greenwich, CT 06830
/40
$4,300,000
- 6 Beds
- 9 Baths
- 9,525 Sq Ft
278 North Ave, Westport, CT 06880

Set in a coveted estate enclave prized by CEOs and captains of industry, this exceptional, shingle-style residence embodies timeless architecture, extraordinary craftsmanship, and meticulous attention to detail. Built custom for a CEO, the home showcases uncompromising quality and gracious curb appeal that leave a lasting impression. Designed for seamless indoor-outdoor living and grand-scale

Cyd Hamer William Pitt Sotheby's Int'l

278 North Ave, Westport, CT 06880
/20
$21,000,000
- 8 Beds
- 12 Baths
- 14,071 Sq Ft
8 Fox Run Ln, Greenwich, CT 06831

Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls of

James Hoffman Houlihan Lawrence

8 Fox Run Ln, Greenwich, CT 06831
/40
$3,895,000
- 8 Beds
- 9 Baths
- 12,853 Sq Ft
27 Country Club Rd, Ridgefield, CT 06877

"HOMEWOOD" - This remarkable country compound is one of the precious few 18th/19th century shingle style colonial revival estates remaining in Fairfield Cty. Dating back to 1750, the original pre-revolutionary war home captivated the attention of prominent NYC banker, George Haven, who purchased the home in 1890 & expanded it significantly including a glorious 50' ballroom designed by Elsie de

Laura Ancona William Pitt Sotheby's Int'l

27 Country Club Rd, Ridgefield, CT 06877
/50
$75,000,000
- 8 Beds
- 14 Baths
- 15,944 Sq Ft
1233 Rock Rimmon Rd, Stamford, CT 06903

An extraordinary 268-acre legacy estate spanning the New York-Connecticut border, Hillandale offers unrivaled privacy and timeless grandeur. Once owned by the Sulzberger family of the New York Times, the 15,000+ sq ft, eight-bedroom European-inspired manor has been meticulously restored and features magnificent formal entertaining rooms, 11 fireplaces, two elevators, a paneled library, sun-filled

Leslie McElwreath Sotheby's International Realty

1233 Rock Rimmon Rd, Stamford, CT 06903
/24
$11,250,000
- 5 Beds
- 6.5 Baths
- 6,966 Sq Ft
188 Round Hill Rd, Greenwich, CT 06831

Spanning 11 remarkable Mid-Country acres on Round Hill Road, this exceptional property offers sweeping western exposures over rolling meadow land framed by mature specimen trees--an increasingly rare and investment-worthy setting. The five bedroom main residence, designed by renowned architect Mott B. Schmidt, showcases elegant formal spaces, an eat-in kitchen, and a tranquil primary suite with

Leslie McElwreath Sotheby's International Realty

188 Round Hill Rd, Greenwich, CT 06831
/7
$10,350,000
- 6 Beds
- 8 Baths
- 7,072 Sq Ft
12 Woodside Rd, Greenwich, CT 06830

DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive,

Leslie McElwreath Sotheby's International Realty

12 Woodside Rd, Greenwich, CT 06830
/40
$3,900,000
- 6 Beds
- 11 Baths
- 9,974 Sq Ft
76 Lords Hwy, Weston, CT 06883

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every

Alex Chingas Coldwell Banker Realty

76 Lords Hwy, Weston, CT 06883
/56
$8,000,000
- 5 Beds
- 5 Baths
- 3,669 Sq Ft
640 Round Hill Rd, Greenwich, CT 06831

This is an opportunity to own a piece of Greenwich history. A fully restored antique farmhouse offering approximately 3,669 square feet of refined living space, set on extraordinary level acreage with sweeping meadow views and an irreplaceable country setting across from protected conservation land with direct access to the Greenwich Riding Trails. The residence blends historic authenticity with

Monica Webster Douglas Elliman of Connecticut

640 Round Hill Rd, Greenwich, CT 06831
/33
$13,000,000
- 5 Beds
- 10 Baths
- 9,564 Sq Ft
10 Shorehaven Rd, Norwalk, CT 06855

Rarely does an opportunity arise to own a home in the coastal enclave of Shorehaven, and 10 Shorehaven Road is a true masterpiece. This Nantucket-inspired estate blends timeless elegance with relaxed coastal charm, offering unmatched luxury and tranquility. Set along the serene waterfront, the lush, landscaped grounds feature a sparkling pool, spa, and private dock-perfect for boating adventures

Laurie Morris Compass Connecticut, LLC

10 Shorehaven Rd, Norwalk, CT 06855
/40
$1,950,000
- 5 Beds
- 5.5 Baths
- 8,530 Sq Ft
63 Parmalee Hill Rd, Newtown, CT 06470

This home is sold WITH the adjacent Building Lot #65 Parmalee Hill Road. TOTAL of 4.09 ACRES. #65 Parmalee Hill Rd is a R-2 Zoned lot (2.04) with shed/barn on property. Beautifully appointed Colonial Style home, built in 2006, with breathtaking views of the surrounding valley. Located in a residential, semi-rural section of Newtown, with easy access to major routes. Throughout the home you will

Erika Portanova Songer William Pitt Sotheby's Int'l

63 Parmalee Hill Rd, Newtown, CT 06470
/39
$7,395,000
- 6 Beds
- 10 Baths
- 9,051 Sq Ft
33 Highland Farm Rd, Greenwich, CT 06831

Tucked away on over seven quiet acres off prestigious Round Hill Road, this private estate offers a serene blend of luxury, space, and style. The main residence is complemented by a beautiful pool/guest house designed for effortless entertaining and resort-style living. At the heart of the home, a Christopher Peacock kitchen showcases statuary marble countertops and backsplash, double islands,

Joy Kim Metalios Houlihan Lawrence

33 Highland Farm Rd, Greenwich, CT 06831
/27
$12,495,000
- 6 Beds
- 11 Baths
- 10,421 Sq Ft
537 North St, Greenwich, CT 06830

Exquisite six-bedroom stone manor, executed to the highest standards, and sited atop a majestic knoll on 2.97 picturesque acres in the heart of Mid-Country Greenwich. Chic, sophisticated interiors by Amy Hirsch unfold across three levels of light-filled living space, highlighted by soaring ceilings, oversized custom windows, and every modern amenity. An elegant double-height entry hall with

Leslie McElwreath Sotheby's International Realty

537 North St, Greenwich, CT 06830
/37
$13,000,000
- 5 Beds
- 10 Baths
- 10,197 Sq Ft
865 Hollow Tree Ridge Rd, Darien, CT 06820

Set on 7 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational

Ashley Dineen Compass Connecticut, LLC

865 Hollow Tree Ridge Rd, Darien, CT 06820
/39
$15,000,000
- 5 Beds
- 10 Baths
- 10,197 Sq Ft
865 Hollow Tree Ridge Rd, Darien, CT 06820

Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house

Ashley Dineen Compass Connecticut, LLC

865 Hollow Tree Ridge Rd, Darien, CT 06820
/40
$4,400,000
- 5 Beds
- 8 Baths
- 9,819 Sq Ft
1 Flower Farm Ln, Westport, CT 06880

Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

Heather Fitzgerald Coldwell Banker Realty

1 Flower Farm Ln, Westport, CT 06880
/40
$4,999,000
- 5 Beds
- 9 Baths
- 7,070 Sq Ft
294 Maple Rd, Easton, CT 06612

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 6 acres on a cul-de-sac, offering a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered

Linda Toscano Coldwell Banker Realty

294 Maple Rd, Easton, CT 06612
/40
$5,499,000
- 5 Beds
- 9 Baths
- 7,070 Sq Ft
294 Maple Rd, Easton, CT 06612

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood

Linda Toscano Coldwell Banker Realty

294 Maple Rd, Easton, CT 06612
/34
$874,959
- 6 Beds
- 3.5 Baths
- 4,514 Sq Ft
190 5th Ave, Stratford, CT 06615

Life at the beach is a year round vacation in the coveted community of Lordship. A charming yet spacious home has been part of one family's history for generations. This lovingly maintained & carefully updated home has almost 3200 SF & is considered to be 7 BRS by the town w/ 3.5 Baths. The perfect home for family & friends to gather! Upon entering this home you experience the best of beach

Marilyn Heffers Coldwell Banker Realty

190 5th Ave, Stratford, CT 06615
/28
$24,000,000
- 10 Beds
- 16 Baths
- 15,820 Sq Ft
5 & 7 John St, Greenwich, CT 06831

Robin Hill Farm' and 'Smokey Hill Farm' are situated at one of the highest points in Greenwich in bucolic backcountry. This magnificent estate encompasses the main house, represented in this listing data sheet, two cottages, stables and gorgeous paddocks, Indoor and outdoor pools, tennis house, tennis court, and two ethereal fountains. Originally designed in 1937 by Augusta L.Noel (designer of

Shelly Tretter Lynch Compass Connecticut, LLC

5 & 7 John St, Greenwich, CT 06831
/23
$10,350,000
- 5 Beds
- 4 Baths
- 8,223 Sq Ft
111 Byram Shore Rd, Greenwich, CT 06830

Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage

Joseph Barbieri Sotheby's International Realty

111 Byram Shore Rd, Greenwich, CT 06830
/47
$3,499,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 5,389 Sq Ft
399 Stanwich Rd, Greenwich, CT 06830

Set amid scenic beauty, this custom-built Colonial offers over 5,300± square feet of elegant living space across four levels, complete with an indoor swimming pool and a charming guest cottage. Sun-filled formal living and dining rooms showcase soaring ceilings and beautiful natural light, while the kitchen with breakfast room opens to a comfortable family room. The serene primary suite provides

Leslie McElwreath Sotheby's International Realty

399 Stanwich Rd, Greenwich, CT 06830

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