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203 Wildflower Ln, Fairfield
$1,785,000
5 Beds ⋅ 4 Baths ⋅ 24214910 MLS
Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this newly renovated home sits on a private 2.4-acre lot and offers Fairfield living at its finest. This 5-bedroom home, with four full and two half bathrooms, boasts spacious interiors, an open floor plan, all-new finishes, and a brand-new primary bedroom suite addition above a three-car garage. The exterior is just as stunning as the interior, featuring custom stonework and a fully updated gunite inground pool, ready to be enjoyed this summer. The home offers an effortless indoor-outdoor lifestyle, perfect for relaxing at home or entertaining guests. Move-in ready, 203 Wildflower Lane is the perfect blend of quality, privacy, and location. Brand new property drainage system installed in October 2026.

203 Wildflower Ln, Fairfield

50 Judges Hollow Rd, Fairfield
$1,475,000
4 Beds ⋅ 3 Baths ⋅ 24215458 MLS
Nestled among 3.56 acres of beautiful woodlands, this classic four-bedroom Dutch Colonial offers an inviting blend of timeless character and comfortable living. Enjoy tranquility with easy access to all that Fairfield has to offer. There are hardwood floors throughout, a welcoming foyer, a large living room with fireplace, and sliding doors that lead to an amazing screened porch surrounded by nature, making it the perfect spot for your morning coffee. An updated kitchen and spacious dining room with doors leading to a private patio are perfect for entertaining. Completing the main level are an office and half-bath. Upstairs you will find four bedrooms, two bathrooms, and a large bonus room. The lower level has a recreation room and plenty of storage. Be sure not to miss the two-story barn on the property. It's perfect for the animal enthusiast or as extra space for creative projects and hobbies. It even has a second story that can be transformed into a home office-or just a cool place to hang out! This home is a must see; a real stunner.

50 Judges Hollow Rd, Fairfield

88 Springer Rd, Fairfield
$1,599,000
4 Beds ⋅ 3 Baths ⋅ 24214100 MLS
Welcome to this gracious, 4-bedroom center hall Colonial, ideally situated on .61 acres in Fairfield's sought-after lower Greenfield Hill area. Offering 3,421 square feet of living space, plus an additional 600 finished square feet in the lower level, this sun-filled home combines classic details with a comfortable, open floor plan. 9-foot ceilings, 2 fireplaces, hardwood floors and custom millwork add character throughout. The spacious family room features a dramatic floor-to-ceiling stone fireplace and opens to the eat-in kitchen, complete with stainless steel appliances, double ovens and abundant cabinetry. An elegant dining room, living room with fireplace, powder room, and laundry room complete the main level. Upstairs, four generously sized bedrooms include a primary suite with a walk-in closet and an expansive full bath featuring a double vanity, Jacuzzi tub, and separate shower. Three additional bedrooms offer ample closet space and share a full bath with a tub/shower combination. The lower level features a 36 X 15 finished space perfect for a recreation room, playroom, office, media room or a combination of these! A large unfinished area offers abundant storage space. Outside, the fully fenced backyard with bluestone patio offers a private and peaceful setting bordering wooded, town-owned land. Complete with mudroom, attached 2-car garage, full house generator and security system, this move-in-ready home is centrally located to enjoy ALL that Fairfield has to offer!

88 Springer Rd, Fairfield

18 Merry Meet Cir, Fairfield
$2,300,000
4 Beds ⋅ 8 Baths ⋅ 24214588 MLS
Welcome to 18 Merry Meet Circle, an architecturally distinctive residence nestled within The Ridge, Fairfield's prestigious gated community. Ideally situated near the end of a quiet cul-de-sac in desirable Greenfield Hill, this exceptional home offers remarkable privacy, mature landscaping, and a resort-inspired lifestyle. Residents enjoy a 24-hr. staffed gatehouse, a private clubhouse, a heated Gunite swimming pool, lighted Har-Tru tennis courts, a skating pond, bridle & walking trails. A circular stone driveway welcomes you to a home showcasing distinctive architectural details, natural stone, rich wood accents, and exceptional craftsmanship. Beautifully designed living spaces include a spacious kitchen, separate dining room, and expansive living room with a magnificent stone fireplace. A custom stone-and-wood staircase adds a striking architectural focal point. The thoughtfully designed lower level is an entertainer's dream, featuring a private fitness retreat with gym and authentic sauna, bar area, theater room, butler's pantry, private office, and additional living space. Expansive glass walls and doors create an inviting atmosphere, additional rooms and staff quarters offer flexibility for a variety of needs. Recent improvements include a new roof, updated mechanical systems, new water heater, and whole-home dehumidification system. Residents of The Ridge enjoy a 24-hour staffed gatehouse, private clubhouse and recreation center, heated Gunite pool. Total Sq. Ft. 7,100

18 Merry Meet Cir, Fairfield

443 Brambley Hedge Cir, Fairfield
$2,695,000
4 Beds ⋅ 7 Baths ⋅ 24211002 MLS
Approached by a winding drive at the end of a quiet cul-de-sac in Fairfield County's premier gated community, The Ridge, this distinguished Colonial Revival residence is privately sited atop a gentle knoll on two beautifully landscaped acres. Expansive lawns, mature plantings, and private terraces create a tranquil setting with exceptional privacy. Spanning Four levels and approximately 7,300 square feet the home is designed for both comfortable everyday living and grand scale entertaining. A spectacular Great Room with fireplace flows into the light filled Kitchen and dramatic 2 story Breakfast Room, with both spaces opening to the terrace for effortless indoor-outdoor living and al fresco dining. A 2-story Foyer, formal Dining Room, Mudroom and home Office complete the main level. Accessed by front and back stairs the second level offers a luxurious Primary Bedroom featuring a fireplace, spa-like Bath and walk in closet, 3 additional en-suite Bedrooms and a large Bonus/Play Room. A sizeable third floor Craft/Office/Multipurpose Room provides exceptional flexibility including possible 5th Br. The home's striking appeal continues in the finished walk out lower level with mirror walled Gym and impressive Party/Game Room with fpl and fully equipped wet bar with wine cooler, ice maker and double drawer under counter refrigerators. Ideally located along the Fairfield/Westport line, The Ridge offers a true Country Club lifestyle with Clubhouse, Pool, Tennis Courts and Playground.

443 Brambley Hedge Cir, Fairfield

590 Sturges Hwy, Fairfield
$5,975,000
6 Beds ⋅ 8 Baths ⋅ 24209002 MLS
For those who believe luxury should never feel predictable. This remarkable Southport estate is a masterful reinvention of new construction...where timeless architecture meets modern artistry, extraordinary craftsmanship, and effortless living. Every element feels intentional, from dramatic windows and beautifully scaled rooms to custom millwork, sophisticated lighting, advanced technology, and finishes chosen for beauty rather than trend. Walls of glass dissolve the boundary between indoors and out, revealing a private, beautifully landscaped setting with a breathtaking pool and cabana...a sanctuary that feels worlds away, yet is moments from everything. 8800 Sqft of unsurpassed quality offering an exceptional floor plan that must be experienced to be appreciated. Chef's will appreciate the exceptional Kitchen, the primary suite is an indulgent retreat, while exceptional entertaining spaces make the home equally suited to intimate evenings and unforgettable gatherings. A completely separate, perfectly renovated guest house with its own address, utilities & garage offers a rare luxury in itself...privacy & possibilities for guests, extended family, office, caretaker or rental income. And the location may be the ultimate luxury: the beauty and charm of Southport, award-winning Fairfield schools, beaches and amenities, and coveted Westport resident privileges including Compo Beach and Longshore. One extraordinary property. Two exceptional lifestyles. In a word...Perfection.

590 Sturges Hwy, Fairfield

1321 Brookside Dr, Fairfield
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 24210726 MLS
Welcome to The Enchantment, a magical 2.90-acre oasis in the heart of lower Greenfield Hill. Built in 1894, this charming antique farmhouse has been meticulously renovated and expanded to 2,064 square feet, blending historic character with modern comforts. Originally configured with four bedrooms, the home has been reimagined with an open, inviting floor plan and the flexibility to reintroduce a first-floor bedroom with en-suite bath. Gorgeous wood floors, exposed beams and natural wood trim lend warmth and rustic elegance throughout, while the beautifully renovated kitchen serves as the heart of the home. No detail was overlooked, with a new roof, Marvin windows, boiler, electrical, plumbing, kitchen and baths. Outside, meandering pathways weave through enchanting gardens designed by renowned botanist and floral designer Peter Stephens. Discover bubbling fountains, hidden garden vignettes and unexpected places to gather and retreat. An exceptional collection of outbuildings includes the original barn with vaulted ceilings and loft; an adjoining heated gathering studio with wood floors and new skylights; a picturesque three-stall barn with loft, cupola and attached poultry shed; a dedicated workshop barn; and a large storage shed. Each building has been thoughtfully improved, with new roofs throughout and additional updates as needed. The Enchantment is truly a world of its own-a rare combination of historic charm, modern comfort, extraordinary gardens and versatile spa

1321 Brookside Dr, Fairfield

241 Hemlock Hills Rd S, Fairfield
$1,459,000
4 Beds ⋅ 3 Baths ⋅ 24211408 MLS
Welcome home to 241 Hemlock Hills Road South, a New England charmer nestled on a quiet cul-de-sac and set on a peaceful, private 2+ acre lot. Move-in-ready and filled with warmth, this spacious home offers 10 generously sized rooms across three levels of living. Natural light fills each room through numerous windows, framing beautiful views of the surrounding mature landscaping and surroundings. Standout features include four wood-burning fireplaces, hardwood flooring throughout, custom built-ins, and a thoughtfully designed floor plan that provides a great flow for entertaining as well as everyday living. The second level features four bedrooms, including the spacious primary suite, creating a convenient and comfortable bedroom layout. Step outside to the oversized deck and enjoy the tranquility of this expansive property, where beautiful wild life, mature plantings, and visiting birds create a truly peaceful setting. And while the property feels wonderfully private and tucked away, it is remarkably convenient-just moments from the elementary school, parks, Audubon Society, town center, and shopping. Life feels a little easier here. Enjoy the space, privacy, features, and natural beauty of this special home while creating lasting memories for years to come.

241 Hemlock Hills Rd S, Fairfield

60 Bridle Trl, Fairfield
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 24202150 MLS
Classic Greenfield Hill Colonial located in desirable Galloping Hill neighborhood. Wonderful turn-key home has been gently lived in and boasts Formal Living Room with wood burning Fireplace & Formal Dining Room with coffered ceiling and Butler's Pantry. Light-filled Kitchen with new backsplash & Quartzite counter tops offers good space for cooking & entertaining. Laundry Room and Powder Room are located off Kitchen. Family Room with its wood burning Fieldstone Fireplace features roomy space and opens nicely out to refreshing blue slated Patio. Home Office is located on Main Level. Beautiful mill work greets you as you ascend the staircase to the Upper Level. Spacious Primary en-suite Bedroom, en-suite 2nd Bedroom, plus 2 additional well-proportioned Bedrooms and Hallway Bath complete the 2nd Level. Walk-up Attic provides excellent storage. Partially finished walk-out Basement (784 sq ft) offers work out space & space for children to play. Basement with add'l 1,134 unfinished square footage provides opportunity & abundant storage space. Insulated 600 sq ft space located above 3 car Garage could make ideal Bonus Room. Plenty of shopping & dining on either Black Rock Tpk or Downtown Fairfield. The wonderful coastal community of Fairfield boasts 5 scenic beaches. 60 Bridle Trail is an excellent & welcoming family home just minutes to the Merritt Pwy, 10 minutes to I-95, train and downtown.

60 Bridle Trl, Fairfield

2493 Redding Rd, Fairfield
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 24208162 MLS
Transport yourself back in time in this classic Greenfield Hill colonial! This renovated 1817 stunner offers over 5,000 square feet of living space - complete with private accessory apartment, a light & welcoming sunroom, bucolic barn and amazing gunite pool with waterfall! Mature plantings and trees abound on this spacious, rolling property. A dramatic, two-story front entry with sweeping staircase welcomes you home. Hardwood floors and high ceilings give even more character and elegance to the home. A more contemporary, open floor plan runs throughout the first floor - highlighted by a chef's kitchen, family room and formal dining room (both with fireplaces), living room, den with fireplace, office and more! The primary bedroom suite with elegant bath and walk-in closet punctuates the fantastic second floor, with three additional bedrooms. The home is perfect for hosting parties and overnight guests. An apartment (w/separate entrance) over the garage, an attached three-car garage and charming front porch are further features of this pastoral, private & relaxing home and property. Enjoy everyday or on the weekends! The two-story barn with three stalls and large pasture adds even more to your experience! It has three large stalls - perfect for trail rides - a stone's throw away at The Fairfield Bridle Trails and Brett Woods! Additional riding opportunities at the nearby Fairfield County Hunt Club. Close to Fairfield & Westport shopping, restaurants, entertainment & commuting

2493 Redding Rd, Fairfield

480 Riders Ln, Fairfield
$1,086,500
4 Beds ⋅ 4 Baths ⋅ 24206575 MLS
Totally refreshed with many new improvements including a stunning kitchen island, this mid-century modern classic home is tucked away at the end of a wide, welcoming cul-de-sac in the heart of Greenfield Hill. Spanning 5,000 sq ft with 4/5 bedrooms and 4 updated full baths, this beauty is set on 2 sprawling, private acres. A prime feature is the breathtaking great room w/soaring 12ft+ ceilings and a dramatic wall of glass. The formal dining room has 9ft ceilings and a bank of floor-to-ceiling windows. The island kitchen with large walk-in pantry has been expanded and is outfitted with newer 2024 top-tier appliances. The adjacent sun room is perfect as a casual eating area and is drenched with sunlight through the two walls of windows. Another main floor feature is a flex room, boasting its own full bath and walk-in closet, ideally suited as either an in-law suite or family room. Retreat to the main floor primary bedroom suite with an updated full bath & an oversized walk-in closet. 3 additional good sized secondary bedrooms round out this spacious and well designed home. Outside, the expansive deck allows you to take in the lush, private grounds. Car enthusiasts will appreciate the two double-bay attached garages, all accessed via a graceful circular driveway. This tranquil location provides easy access to local boutique shopping, vibrant dining scenes, coastal beaches, and convenient transportation links. Opportunity awaits at 480 Riders Lane!

480 Riders Ln, Fairfield

3901 Redding Rd, Fairfield
$1,495,000
5 Beds ⋅ 4 Baths ⋅ 24205061 MLS
Quintessential New England architecture, extraordinary grounds & an interior that continually surprises define this distinctive Greenfield Hill property. Privately set behind a stone wall on 2 exquisitely landscaped acres, this stately clapboard Colonial is beautifully sited w/cedar roof, cupola, rows of boxwood, bluestone walk & gracious front porch. Inside beautifully appointed rooms unfold w/remarkable versatility, warmth & exceptional flow for entertaining. Gracious living room w/gas fireplace leads to inviting dining room while the sun-filled kitchen overlooks the spectacular landscape & opens through French doors for seamless indoor/outdoor living. Family room w/custom built-ins, window seat & 2nd gas fireplace. Large laundry room & attached 2-car garage complete main level. Upstairs, 5 BR & 3 full BA include a gorgeous en-suite primary. Finished lower level is truly unforgettable: custom Irish Pub inspired by owners' travels to Ireland w/full bar, kegerator, handcrafted details & cozy wood-burning fireplace, creating a one-of-a-kind space for gathering. Outside dine beneath the cedar pergola draped in climbing hydrangea, wander through the English gardens, tend the enclosed vegetable garden, relax in the hot tub, enjoy morning coffee on the garden swing or simply watch nature unfold. Expansive bluestone patios, specimen plantings, mature trees & lush lawns create a setting that feels worlds away. A rare property where beauty, personality & inspired living converge.

3901 Redding Rd, Fairfield

1074 Sturges Hwy, Fairfield
$2,690,000
5 Beds ⋅ 5 Baths ⋅ 24205145 MLS
A rare Greenfield Hill find, 1074 Sturges Highway pairs the presence of a classic Colonial with a sleek, thoroughly modern point of view. Thoughtfully reimagined, the home retains its original craftsmanship while introducing clean-lined updates and a minimalist sensibility that feels chic, current and effortless. Inside, the balance between old and new is masterfully struck. Original millwork and architectural details are paired with elegantly edited finishes, creating spaces that feel sophisticated without ever tipping into formal. The layout flows naturally for everyday living, with room to gather, entertain and simply enjoy the house. Set on over 2 acres of impeccably manicured and extremely private grounds, the property offers a rare sense of seclusion. A gorgeous patio with fireplace extends the living space outdoors, setting the scene for summer dinners, cocktails and fireside evenings. A newly constructed garage with loft above adds flexibility for a home office, studio, gym or creative retreat. Where classic architecture meets a fully modern point of view, 1074 Sturges Highway is a masterclass in understated sophistication. FAIRFIELD SCHOOLS: Schools: DWIGHT, LUDLOW, LUDLOW.

1074 Sturges Hwy, Fairfield

3007 Redding Rd, Fairfield
$2,549,000
4 Beds ⋅ 4 Baths ⋅ 24205159 MLS
Gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport center. Timeless natural beauty, distinctive architecture, exquisite craftsmanship & sophisticated updates combine to create a home that truly stands apart. Featuring 12 rooms flooded w/ brilliant light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to peaceful snow-covered landscapes. The living room fireplace provides a cozy focal point w/ oversize French doors that open to the patio creating an ideal setting for outdoor dining & hosting. The eat-in kitchen offers the dining area, island, pantry & state of the art appliances & guides you to the dining room, office, living room & study. Upstairs the beauty continues w/ 4 large bedrooms including the primary. The lower level expands the living space w/ a new mudroom, rec room, gym & half bath. Updates include a new lower level, flagstone patio, custom pantry w/ wine storage, upgraded laundry room w/ new washer, new window in en-suite & new Rubbermaid track system. Step outside to your patio featuring a built-in Weber BBQ & XL Big Green Egg, perfect for cooking enthusiasts. Exterior has been meticulously maintained w/ repainting, stone-accented walls, Belgium block-lined driveways & ongoing landscaping. A NE bridge adds character. The Patterson Club is a bike ride away. 3007 Redding Road is filled w/ light, space & lasting memories.

3007 Redding Rd, Fairfield

2730 Burr St, Fairfield
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 24202615 MLS
GREENFIELD HILL COLONIAL - Set in a beautiful Greenfield Hill location, this classic Colonial offers an exceptional blend of privacy, space, and convenience. Nestled on a picturesque 2.09-acre property framed by mature trees, stone walls and sweeping lawns, this 2,588-square-foot home features four bedrooms, two-and-one-half baths, and a very well designed floor plan. A welcoming foyer opens to a sun-filled, front-to-back living room with fireplace and an elegant formal dining room. The inviting family room, also featuring a fireplace, connects to the attached two-car garage and flows seamlessly to a wonderful screened porch-an idyllic spot for morning coffee, al fresco dinners, or quiet relaxation. At the heart of the home, the spacious chef's kitchen provides ample room for gathering with family and friends. The expansive property provides exceptional privacy and a lovely backdrop for enjoying the best of Greenfield Hill. While the setting feels enchantingly secluded, the location is just minutes from Fairfield Center, the Arts & Cultural District, outstanding restaurants, boutique shopping, beautiful beaches, and Metro-North service to New York City. First Floor: Covered Breezeway. Foyer with slate flooring, guest closet, and Powder Room - provides access to all principal rooms. Front to back Living Room with hardwood flooring, and wood-burning fireplace. Elegant Formal Dining Room with hardwood flooring, and Bay Window. PLEASE OPEN ADDENDUM FOR FURTHER DESRIPTION.

2730 Burr St, Fairfield

128 Cobblers Hill Rd, Fairfield
$2,395,000
4 Beds ⋅ 5 Baths ⋅ 24203568 MLS
This beautifully crafted 4,600 sq. ft. Colonial, built by renowned builder Frank Dooley, combines exceptional craftsmanship with thoughtful design. Located on a welcoming cul-de-sac in lower Greenfield Hill, the home features spacious rooms with clear sightlines that create a comfortable flow. At the center of the home, a generous kitchen seamlessly connects to the dining area and one of two large stone patios, ideal for both everyday living and entertaining. The expansive family room and elegant front-to-back living room each feature a fireplace, while a charming sunporch offers a cozy retreat. A finished bonus room above the garage provides flexible space for 5th bed, media room. Upstairs, four spacious bedrooms include a well-appointed primary suite with 2 full baths, an ensuite bedroom, and two additional bedrooms sharing an updated hall bath. Abundant custom built-in storage throughout and a finished third floor office enhances the home's versatility. The level, fenced, and beautifully landscaped 2+acres, designed by Oliver's Nursery, features irrigation and outdoor lighting. A 11'-23' room accessible from the yard and garage offers extra storage with finishing potential. Enjoy the convenience of walking to local shops and the farmers market, with easy access to downtown Fairfield, Merritt Pkwy, and I-95. This home offers effortless living in a prime location where everyday life feels relaxed and refined.

128 Cobblers Hill Rd, Fairfield

220 Stonewall Ln, Fairfield
$1,700,000
5 Beds ⋅ 4 Baths ⋅ 24184245 MLS
Nestled at the end of a peaceful cul-de-sac, in the highly sought-after Greenfield Hill neighborhood, 220 Stonewall Lane offers a rare opportunity to own a beautifully situated home on 2.07 acres. The expansive outdoor setting provides an inviting space perfect for entertaining or relaxing while enjoying the tranquil surroundings. When entering the thoughtfully planned main level, you are drawn to the large open space with a renovated modern eat-in kitchen, a sitting area with a wood-burning pizza oven, a Great Room with cathedral ceilings, a wood-burning fireplace, and an additional family room with views of the in-ground pool and lush landscaped grounds. Natural light flows throughout. Additional highlights include hardwood floors throughout, large decorative tiles, a formal living room with fireplace, a dining room, walk-up bonus room, laundry and access to the two-car garage. Upstairs, five well-appointed bedrooms include a private primary suite, creating a comfortable and functional area. The unfinished basement offers ample space for utilities, storage and possible recreational activities. Ideally located near Fairfield's beaches, Metro-North, recognized restaurants, and the Fairfield Theatre Company, this private property blends lifestyle, location, and appeal in one of Fairfield's most desirable areas.

220 Stonewall Ln, Fairfield

344 Fence Row Dr, Fairfield
$3,399,900
5 Beds ⋅ 8 Baths ⋅ 24194239 MLS
Old-world craftsmanship meets modern indulgence. Set on a peaceful, tree-lined street,this home offers total privacy and timeless curb appeal. Soaring ceilings, hand-finished millwork, and custom detail are evident throughout. This grand 5BR/6.5BA light filled residence pairs classic entertaining spaces - formal LR, formal DR, & a wood-paneled library w/wet bar & full BA-with modern amenities such as a two-story FR w/ stone FP, a stunning windowed sunroom overlooking the beautiful grounds,& an impressive chef's kitchen boasting custom appliances, double sub zero, island, & dual butler's pantries.Thoughtful proportions create a seamless flow, a home as comfortable day-to-day as it is for grand-scale entertaining.The opulent primary suite is a spa retreat onto itself, w/ dual baths, dual walk-in closets,& a private sauna.The second floor offers 3 add'l en-suite BRs w/ built-ins and large closets. The third floor offers a great room w/ custom built-ins, plus an additional BR and full BA . The lower level feat a recently upgraded state-of-the-art movie theater, gym, game room, & workshop for a serious hobbyist. The expansive, landscaped grounds offer true serenity, w/ English gardens framing a resort-caliber pool and spa in a backyard built for entertaining. Timeless elegance, tucked within The Ridge - a gated enclave w/ a staffed gatehouse, clubhouse, pool & tennis courts just minutes to Fairfield and Westport amenities. Truly a special offering w/ultimate privacy& convenience.

344 Fence Row Dr, Fairfield

1760 Hillside Rd, Fairfield
$3,150,000
5 Beds ⋅ 6 Baths ⋅ 24189678 MLS
Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private office, wet bar, and chef's kitchen beneath an expansive skylight. The desirable first-floor primary suite has been transformed with a new spa bath, new gas fireplace, and atrium with a private entrance. Upstairs, a second primary suite features an en-suite bath, dressing room, fireplace, and private balcony. A renovated one-bedroom guest residence with new flooring, updated kitchen and bath, washer/dryer, and private entrance is ideal for extended family, guests, an au pair, or home office. Extensive improvements include a generator, water purification system, drainage system, irrigation, security system with cameras, restored and re-stained roof, renovated mudroom/laundry room, gardens with bluestone walkways and raised beds, and new front fencing. Expansive terraces overlook beautifully landscaped grounds with mature specimen trees and perennial gardens. Just minutes from town, beaches, train, restaurants, and Fairfield Country Day School, this exceptional Greenfield Hill property offers timeless character, privacy, and extensive improvements. Ready to enjoy from the day you arrive!

1760 Hillside Rd, Fairfield

11 Judges Hollow Rd, Fairfield
$925,000
2 Beds ⋅ 2 Baths ⋅ 24176507 MLS
This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With trails leading directly from the back door to a secluded pond and hiking paths, it serves as an ideal weekend retreat and a convenient alternative to the Vermont or Connecticut River Valley. Located only 70 minutes from Grand Central via the Westport train station, this home offers easy access to both the Connecticut coastline and deep woods.

11 Judges Hollow Rd, Fairfield

4800 Congress St, Fairfield
$9,975,000
7 Beds ⋅ 10 Baths ⋅ 24161896 MLS
The former home of Richard Rodgers, composer of The Sound of Music, this 10.92 acre estate with a stunning modern residence was recently fully renovated and expanded, and offers curated one floor living. Generous main rooms are enhanced by lofty ceilings, skylights and walls of glass. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. Separate residential wings include 7 bedrooms and 7 full baths, each with a unique design. All property systems have been upgraded and integrated to work seamlessly .The barn pool house includes a full eat-in kitchen and lounge, bath ,and full gym steps from the pool. An office pavilion is set privately in a quiet garden area. The park like property is surrounded by high stone walls, a nature preserve, open land, a heated paddle tennis court, and an orchard. Live in ultimate style and easy elegance just a quick commute to NYC and airports. This private haven surrounded by a 155 acre nature preserve is minutes to Fairfield, Westport and Greenwich dining and shopping.

4800 Congress St, Fairfield

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