Fairfield Real Estate

5 Bedroom Homes for Sale in Fairfield, CT

Welcome to your dedicated resource for 5 bedroom homes for sale in Fairfield, CT. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Fairfield, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 5 Bedroom Homes for Sale in Fairfield, CT

$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
$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
$2,850,000
5 Beds ⋅ 6 Baths ⋅ 24188324 MLS
Spectacular custom estate built by Andy Frank in prestigious Greenfield Hill featuring a rare first-floor primary suite w/fireplace, spacious WIC, luxurious spa bath & vaulted ceiling -- a true standout for convenient main-level living. Set on over 2 magnificent landscaped acres on a double cul-de-sac, this home delivers resort-style living w/exceptional privacy. Outside, an oversized free-form gunite pool w/waterfall anchors spectacular entertaining & relaxing areas, complemented by stone walls, a large stone patio, and lovely deck - and enhanced by beautiful mature plantings & deer fencing. Inside, a dramatic double-height foyer w/marble floor leads into a custom EIK with quartz countertops, an oversized island & pantry that opens seamlessly to the lovely family/living room & idyllic backyard. Another larger family room features a custom bar, pool table, built-ins, and a half bath. Three fireplaces, a first-floor library/office, custom laundry room & two staircases complete the first floor. Upstairs, the second floor offers four large bedrooms & two beautifully full baths. The finished walk-out LLevel is an entertainer's dream, complete w/custom wine cellar, full bath, wet bar, multiple entertaining zones, storage rooms & gym space. Exquisite millwork & detail throughout. This private, spacious setting is a short drive to the train for NY commuters, & to vibrant shops, restaurants & the energy of downtown Fairfield & Westport. Natural gas completes this special property.

73 Foggwood Cir, Fairfield
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