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550 Rolling Hills Dr, Fairfield
$1,600,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24126270 MLS
Welcome to this beautifully updated 4+ bedroom Colonial in a sought-after Greenfield Hill neighborhood, surrounded by rolling lawns and tree-lined streets. Offering over 3,000 sq. ft. of elegant living space plus 1,000+ sq. ft. in the spacious finished walk-out lower level, this home provides exceptional versatility and comfort. The grand entryway opens to a formal living and dining room with custom built-ins. The inviting family room, with vaulted ceilings and a natural stone fireplace, flows seamlessly into the impeccably updated eat-in kitchen. From here, sliding doors lead to an expansive Trex deck with a built-in gas grill, perfect for indoor/outdoor entertaining against the backdrop of a serene, private wooded yard. A mudroom, laundry area, and powder room complete the first floor. Upstairs, the tranquil primary suite features a walk-in closet and a spa-like bath with soaking tub, stall shower, and double vanity. Three additional bedrooms and a full bath complete the second level. The finished lower level includes a bedroom/office/potential au pair suite with full bath, ample storage, and walk-out access. Notable upgrades include fresh interior and exterior paint (2025), new roof (2024), remodeled kitchen and primary bath (2023), refinished hardwood floors (2023), and driveway sealing (2023). Meticulously maintained mechanicals and thoughtful updates make this home truly move-in ready.

550 Rolling Hills Dr, Fairfield
125 Mayweed Rd, Fairfield
$1,600,000
4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24111965 MLS
Welcome to this exceptional 2015-built Colonial, tucked away on a quiet cul-de-sac in Fairfield's sought-after University area. Offering the perfect blend of style, comfort, and convenience, this home is just minutes from beaches, shopping, dining, and entertainment, with easy access to I-95, Metro North, and Amtrak. Inside, a bright and open layout sets the stage for both everyday living and effortless entertaining. The gourmet kitchen with granite countertops and stainless-steel appliances flows seamlessly into the sun-filled family room with a fireplace. A spacious living room is ideal for game nights or evening relaxation, while the formal dining room creates the perfect backdrop for holidays and celebrations. A mudroom with a half bath adds thoughtful functionality. Upstairs, retreat to the luxurious primary suite featuring a sitting area, two walk-in closets, and a spa-like bath with a soaking tub, walk-in shower, and dual vanities. Three additional bedrooms, two full baths, and a convenient laundry room complete this level. The versatile lower level offers endless options-playroom, gym, home theater, or game room-plus a full bath and generous storage. Outside, a slate patio and landscaped yard invite you to enjoy barbecues, morning coffee, or quiet evening downtime. Move-in ready and beautifully maintained, this home offers the perfect balance of space, style, and location. Don't miss the opportunity to make it yours!

125 Mayweed Rd, Fairfield
692 Stillson Rd, Fairfield
$1,599,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24173246 MLS
Welcome to 692 Stillson Road, Fairfield -where luxury and serenity converge. A stunning Modern Colonial, 4-bedroom + home office designed for those who seek both elegance and harmony. This home is more than a residence; it is a perfectly balanced space, meticulously maintained with exquisite crown moldings, custom millwork, 9-foot ceilings, and gleaming hardwood floors. Ideal location, close to top schools, shopping, beaches and an easy NYC commute, offering both convenience and a sense of alignment. Over $60,000 in recent upgrades ensure effortless living: a fully waterproofed basement with transferable warranty, a newly added office, and a new HVAC system (2025). Step into a dramatic 20-foot foyer filled with natural light and fresh, neutral tones. The formal dining room impresses with elegant custom trim and a coffered ceiling, perfect for entertaining. At the heart of the home is the chef's kitchen featuring high-end stainless steel appliances and an extraordinary 8-foot solid Carrara marble island. The open-concept layout flows seamlessly into the expansive family room, anchored by a warm gas fireplace. The luxurious primary suite offers a private retreat with a tray ceiling, spacious walk-in closet, and spa-like bath with marble floors, glass-enclosed shower, and oversized soaking tub. Three additional generously sized bedrooms provide comfort and flexibility, while the private office with four closets offers exceptional storage and an ideal work-from-home setup.

692 Stillson Rd, Fairfield
200 Joan Dr, Fairfield
$1,595,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24167642 MLS
Nestled in the heart of the most desirable neighborhood in Fairfield with elegant flow, and outstanding indoor-outdoor living. This beautifully renovated home features 4 bedrooms, 2.2 bathrooms and a thoughtfully designed layout with meticulous craftsmanship for modern living. Highlights include an open concept family room with a cozy fireplace, formal dining room, and a gourmet kitchen with stainless steel appliances, a gas stove, and walk-in pantry. The coffee station flows effortlessly into the inviting living room with a fireplace-perfect for both entertaining and everyday relaxation. Thoughtfully reimagined with meticulous craftsmanship This sun-filled home features an abundance of windows and natural light, hardwood floors throughout, expansive living and entertaining spaces Upstairs, the primary suite includes three closets and a custom primary bathroom with floating tub and arched walking shower. Three more additional generous size bedrooms and full bath complete the second level. The finished lower level provides excellent recreation and fitness space, half bath, and a luxury office. Additional features include abundance of windows and natural light, hardwood floors throughout, central heating and cooling, two-car garage, fresh paint throughout, a massive patio with firepit and retaining wall, generator, New asphalt driveway, New vinyl siding, New architecture metal roofing, ...

200 Joan Dr, Fairfield
179 Lawrence Rd, Fairfield
$1,590,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24169263 MLS
Location, Location!! Welcome to 179 Lawrence Road - this home is a beautifully maintained and thoughtfully updated 4 bedroom, 2.5 bath Colonial on a level 0.26-acre lot in one of Fairfield's most desirable neighborhoods. Located on a quiet, welcoming street whose entire length is lined with mature oak trees, the neighborhood is just moments from downtown shops, restaurants, top-rated schools, Metro-North and Fairfield U. This home offers the perfect blend of classic New England character and modern living. Step inside to find a main level that flows effortlessly for both everyday living and entertaining, hardwood floors throughout, a formal living room with fireplace, dining room with sliders out to the quaint backyard terrace, gourmet eat-in kitchen with a generous island and eating area with a wrap around bench seating surrounded by over-sized windows and a family room w/vaulted ceiling and stone fireplace.The upstairs includes 3 bedrooms with hall bath, walk up unfin attic and a large primary suite with generous walk in closet, laundry room and spacious bath. A custom-finished lower level modeled after a 17th-century ship captain's cabin will wow you with shiplap walls and beams and a built-in entertainment system. Whether you're looking for a forever home or a distinctive property that stands out, this residence delivers character, comfort, and convenience in a highly sought-after location. Don't miss the opportunity to own this unique gem in Fairfield's University area!

179 Lawrence Rd, Fairfield
11 Tuckahoe Ln, Fairfield
$1,590,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24157074 MLS
WELCOME HOME to 11 Tuckahoe Lane. A Fabulous like new 4/5 bedroom colonial in the popular Osborn Hill/FFLD Woods/FFld Ludlowe district! Stately double entry doors - perfect first impression for this beautifully appointed University area colonial, inside & out. One Owner & good as new! Open floor plan for the modern homeowner has a sought after open concept! Kitchen w/center island, WetBar & Family Rm are at the HUB of this Fabulous home. Dedicated home office with adjacent & flexible large front to back LR, perfect for playing & parents working at home. Fast-forward to make it a more formal living space and separation from main family room just steps away on other side of the pretty entry foyer. Deeply placed split center staircase allows for large foyer & open in airy bright entry way. Dine in the dining room, at the island or in EIK. Large pantry, mudroom & pretty powder room, conveniently located via addn'l door, just outside of the Large two car garage with awesome overhead door in the rear! perfect for bringing in lawnmowers bikes, toys, sports equipment without disturbing garaged cars. Pretty yard nicely fenced surrounded w/ green giants, make for beautiful private yard in a natural setting. Walk to Osborne Hill School then Walk a couple feet more on sidewalks & you are in the center of one of Ffld's popular shopping districts on Black Rock:Trader Joe's, Starbucks, The Gap, Delicious Restaurants +Close to I-95/Merritt Pkwy, Beaches & both Fairfield Trains

11 Tuckahoe Ln, Fairfield
107 Buckboard Ln, Fairfield
$1,587,500
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24187463 MLS
Tucked away at the end of a tranquil cul-de-sac in one of Greenfield Hill's most convenient and desirable neighborhoods, this turn-key New England Colonial offers the perfect blend of timeless style, classic design and an exceptional lifestyle at any stage of life. Designed for everyday living and entertaining. Features include an inviting foyer with custom molding, powder room, refinished hardwood floors, Marvin windows, sun-filled formal living and dining rooms. The beautiful granite eat-in kitchen has custom cabinetry, newer appliances, an oversized walk-in pantry and 1st floor laundry. A welcoming family room showcases new custom built-ins and wood burning fireplace with seamless access for indoor-outdoor flow. Upstairs, a spacious primary suite offers a walk-in closet and updated private bath while three additional generously sized bedrooms with ample closet space share the hall bath. Finished lower level expands the living space with a rec room, office area and plenty of storage. Professionally landscaped, flat, one acre fenced rear property with raised garden beds, shed, expanded trex deck with pergola and retractable awning creates an oasis for outdoor living and entertaining. The 'circle' is where bike rides and Easter egg hunts begin and neighbors gather creating a real sense of community. Minutes to town, beach, award winning schools and commuter options.

107 Buckboard Ln, Fairfield
155 Labbance Ln, Fairfield
$1,580,000
5 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24167159 MLS
A once-in-a-generation Japanese-inspired 3 acre sanctuary on the coveted Westport side of Greenfield Hill, this extraordinary property offers a rare fusion of architecture, artistry, and landscape. Designed by the owner, a master gardener, the grounds unfold as a private retreat where the Sasco River winds through natural boulders, hand-laid stone walls, flowering specimen trees, terraced gardens, and peaceful woodland paths. The striking contemporary residence is equally compelling, with an open floor plan anchored by a dramatic cathedral-ceilinged living room. A centrally positioned mission-style kitchen serves as the heart of the home, while the dining room, sunroom, and family room enjoy sun-filled southern exposure and tranquil garden views. A dedicated art gallery and exceptional custom library further distinguish the main level. The main floor also includes the primary suite and two additional bedrooms, while a private third-floor bedroom with full bath offers ideal guest or office space. The walk-out lower level adds a family room plus a separate apartment with kitchenette, sitting area, bedroom, and full bath. Ready for thoughtful updates, this is a rare opportunity to reimagine and elevate a truly special home in one of Greenfield Hill's most peaceful and breathtaking settings. Minutes to Southport/Fairfield and Westport centers. House is not in a flood zone! Sits up high with a view!

155 Labbance Ln, Fairfield
109 Jeniford Rd, Fairfield
$1,575,000
4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24135961 MLS
This light and bright University area home is located on a picturesque, tree-lined street w/sidewalks, just minutes away from the bustling downtown & Metro North train station & walking distance to a sought after local elementary school. This better-than-new residence, completed in 2016 & spanning 4,000+ sq ft over 3 beautifully finished floors, features high-end custom moldings, designer finishes, elegant living spaces & pristine hardwood floors. The heart of the home is the stunning eat-in kitchen, equipped w/honed Carrera marble countertops, a large center island, professional-grade appliances & abundant storage. Adjacent to the kitchen is a spacious custom mudroom and a half bathroom. The family room, central to the home's design, boasts hardwood flooring, a coffered ceiling, gas fireplace, and offers picturesque views w/direct access to the large, private & fully fenced backyard w/beautiful patio & vegetable garden. There is also an expansive dining room w/ coffered ceiling & moldings, and a private home office or living room w/French doors on the main level. The upper level is home to a luxurious primary suite complete w/ a spa-like bathroom, his and hers walk-in closets, hardwood flooring, and a tray ceiling. Additionally, there are 3 more bedrooms, each featuring custom closets and hardwood floors, along with two addit'l full baths & a laundry rm. The lower level features a gym, large entertaining area, full bath & custom built ins and Murphy bed. Gas, city, water.

109 Jeniford Rd, Fairfield
85 Patrick Dr, Fairfield
$1,560,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24139153 MLS
Location, location! This sleek, modern Colonial-ideally situated in the highly desired Sasco neighborhood on a quiet cul-de-sac-awaits its next owner. Gorgeous & rare architectural features make this home a true stand out, including multi-level soaring ceilings, dramatic oversized windows that flood the home w/ natural light & 3 fireplaces for added warmth & charm. Built-ins, 4 bedrooms (including one on the 1st floor) & 3 levels of spacious living combine comfort & versatility. Step inside & your eye is drawn to the impressive scale of the open rooms & inviting warmth that fills the space. The open layout extends easily to the outdoors w/ an oversized deck & a large, private yard. The 1st level features a welcoming living room w/ a fireplace that opens into the dining area. The eat-in kitchen is a chef's dream w/ 2 large ovens, great counter space & an oversized island that flows effortlessly into the cozy family room w/ built-ins & a 2nd fireplace. Bedroom (currently used as an office) & full bath offer flexibility & convenience. Upstairs, the luxurious primary suite serves as a retreat, w/ the 3rd fireplace, dramatically high ceilings, large windows overlooking the tranquil landscaping, 2 walk-in closets & a spa-like bath. 2 additional spacious bedrooms, 1 w/ a loft & full bath complete the 2nd level. The lower level adds living space w/ a recreation room, den & storage. All of this PLUS a short walk to town & the beach makes 85 Patrick Dr. the perfect place to call home.

85 Patrick Dr, Fairfield
355 Surrey Ln, Fairfield
$1,550,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24179417 MLS
Priced below market value for quick sale! Welcome to 355 Surrey Lane - an extensively renovated home where timeless design meets California contemporary and modern organic luxury finishes. Taken down to the studs and rebuilt with exceptional attention to detail and quality, this turnkey home offers the peace of mind of new construction on a level, private 1 acre lot with an enormous backyard and circular driveway in the highly sought after Greenfield Hill neighborhood. Just about every component of this home is brand new to include: AC, Gas Furnace, ductwork, hot water heater, electrical panel and systems, Anderson windows throughout, kitchen cabinets, premium Kitchenaid appliances and 48 inch double gas oven all under manufacturer warranty, 10 foot quartz waterfall island and laundry. Brand new wide plank engineered hardwood floors throughout the home and 3 fully renovated bathrooms. The living areas feature a wide open floorplan, perfect for entertaining and are highlighted by two striking floor to ceiling fireplaces. The home features expansive windows and doors, filling the home with natural light. Low utility bills from all new energy efficient insulation throughout. Huge additional living room/play room. In-law suite with private entrance and bath. Located minutes from major commuting routes and Fairfield's award winning schools, beaches, parks, restaurants, shopping and train. Hurry - this one will not last long

355 Surrey Ln, Fairfield
280 Mill Hill Rd, Fairfield
$1,550,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24170660 MLS
THANK YOU FOR YOUR INTEREST IN 280 MILL HILL ROAD. SELLER IS REQUESTING HIGHEST AND BEST OFFERS TO BE SUBMITTED BY TODAY, MONDAY MAY 11TH AT 5PM. Picture perfect 1920s Colonial in the location we all covet. Welcome to 280 Mill Hill Road, a beautiful center hall colonial that blends timeless character with modern updates-all in an exceptional in-town location. Just a short stroll to Southport Village, this home offers the perfect balance of charm, convenience, and lifestyle. Inside, sun-filled living spaces showcase classic architectural details and a warm, inviting flow ideal. The newly renovated kitchen features stylish finishes and modern functionality, seamlessly complementing the home's historic appeal. The flexible layout includes a finished third floor, perfect as a fourth bedroom, home office, gym or flexible space to suit your needs. Step outside to enjoy an expansive patio overlooking the expansive fenced backyard, surrounded by mature landscaping-an ideal setting for outdoor dining, entertaining, or simply relaxing in a private, picturesque setting. Located within walking distance to Mill Hill School, the train, Southport Village, dining, and the harbor, this is a rare opportunity to own a quintessential Fairfield home.

280 Mill Hill Rd, Fairfield
357 Oldfield Rd, Fairfield
$1,550,000
5 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24134149 MLS
**Seller has accepted an offer. Property is Under Deposit. Open House cancelled for both Saturday and Sunday 10/25-10/26. Coastal Chic Meets Modern Living! Discover the idyllic Fairfield lifestyle in this fully renovated 5BR, 2.5BA home, perfectly located between sandy beaches and vibrant town center. Welcome to 357 Oldfield Road - thoughtfully remodeled and designed for style, comfort and ease, this charming home blends relaxed coastal vibes with privacy, space, and an unbeatable location. Step inside to sun-drenched rooms and sparkling hardwood floors throughout. The open floor plan is designed for casual, everyday living and effortless entertaining flow. A bright Eat-in Kitchen, spacious Family Room w/fireplace, and flexible main floor Office or Playroom offers both comfort and function. The rare MAIN LEVEL Primary Bedroom is a compelling feature for downsizers, and with FOUR more spacious Bedrooms upstairs, there's potential to add a second ensuite Primary BR. Step through French doors to enjoy sunset cocktails on the stunning fieldstone terrace, surrounded by mature, privacy trees, OR relax with your morning coffee on the shady covered porch. The oversized 2-car attached garage provides convenience and extra storage. Located adjacent to friendly, quiet Pratt Street for daily exercise, evening strolls and play. Whether you seek a year-round residence, weekend getaway home, or smart investment, this happy home checks off all the boxes.

357 Oldfield Rd, Fairfield
226 Ruane St, Fairfield
$1,550,000
5 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24122573 MLS
Welcome to your dream come true lifestyle in the heart of Fairfield's coveted beach/town community-where coastal charm meets everyday convenience. This brand-new modern Colonial is more than a home, it's an upgraded living experience. Imagine morning walks to South Pine Creek Beach, afternoons on the tennis courts or golf course & evenings dining at vibrant restaurants, live music & theatres downtown-all just a short stroll from your front door. With the train only minutes away, your commute becomes effortless, leaving more time to enjoy friends, family...and life! This 5-bedroom, 4.5 bath home blends timeless design with a modern edge. The open-concept layout features a bright eat-in kitchen w/ oversized island & custom cabinetry, flowing seamlessly into sunlit gathering spaces designed for both connection & relaxation. A highly desirable first-floor bedroom w/ full bath creates flexibility for guests, in-laws, or a private office. A mudroom area with cubbies offers convenience & style. Upstairs, retreat to a serene primary suite with soaring cathedral ceilings, a spa-inspired bath, walk-in closet, & private balcony boasting beautiful views of the sunset. Bedrooms are thoughtfully appointed w/ custom closets & appreciate a 2nd floor office, while a top-floor suite with full bath provides the ultimate private hideaway. Set on a private quarter-acre lot, this home redefines coastal elegance-where every detail supports a lifestyle of comfort, convenience, and connectivity.

226 Ruane St, Fairfield
1207 Stillson Rd, Fairfield
$1,545,000
5 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24146261 MLS
Start your new year and come home to your Peytonwood retreat tucked away in the coveted University area situated on just under an acre of privacy. With over 4,000 square feet of versatile living area, your main level features a grand two-story foyer, expansive family area with fireplace, custom designed kitchen including quartz counters, Z-line appliances, butler's pantry and dining area with its own cozy fireplace. A spacious first floor bedroom suite with full bath provides comfort and convenience for guests or multi-generational living. Your upper level provides a luxurious primary suite boasting a designer bath and walk in closet room while two additional generous sized bedrooms share a Jack and Jill en-suite bath. A separate bedroom with a full bath offers ideal space for an au pair or in-law suite plus your 3rd level 38'x 16' great room provides recreation area, home office and media space. Private fenced yard for outdoor activities and room for a pool all minutes to beaches, dining/restaurants, retail/shopping, town center and Metro North Train Stations with easy access to I-95 and Rt 15 Merritt Parkway. Immediate occupancy.

1207 Stillson Rd, Fairfield
1180 Merwins Ln, Fairfield
$1,530,000
3 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24179278 MLS
Private Greenfield Hill Retreat on 2+ Acres with Guest Suite, Modern Updates & Equestrian Potential.Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill, this rare property offers privacy, flexibility, and modern comfort. From the moment you enter, the craftsmanship is unmistakable featuring a handcrafted staircase, custom millwork, built-ins, and a dramatic barrel ceiling living room anchored by a stone fireplace. The refreshed chef's kitchen includes a center island, double ovens, pantry, and granite countertops, opening to a sun filled sitting area with views of mature plantings. The floor plan offers exceptional versatility. A first floor wing, currently configured as an in-law suite with full kitchen, bedroom, full bath, walk-in closet, and laundry, can easily function as a primary suite, guest retreat, or additional bedroom adapting seamlessly to changing needs. Upstairs, you'll find two addt'l ensuite bedrooms, a cedar closet, and generous walk in storage, providing privacy and comfort throughout. Addt'l highlights include new main level flooring, upgraded lighting, a whole house generator, and reverse osmosis water filtration system, offering both convenience and peace of mind. Outside, a stone terrace overlooks the expansive backyard, while a separate outbuilding provides space for addt'l vehicles, a workshop, or equestrian use. Ideally located near both Fairfield and Westport, the property feels completely private while remaining close to everything.

1180 Merwins Ln, Fairfield
307 Old Post Rd, Fairfield
$1,525,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24196786 MLS
It's a rare find to discover a classic Beach area Colonial that balances timeless character w/ this price point. Built in 1916, this home captures that sought-after vintage soul from the moment you step onto the covered front porch-complete w/ a swing that's practically begging for a book & a glass of lemonade. Inside, a wide foyer welcomes you into a traditional center-hall layout where original charm meets modern living. You'll find hdwd flrs throughout & a LR centered around a cozy wood-burning FP flanked by custom b/ins. The DR feels elevated w/ its classic corner cabinetry, while the heart of the home-a beautifully remodeled kitchen w/center island-flows effortlessly into an inviting sun-filled FR. Upstairs, 3 comfortable BRs share a stunningly renovated bathrm featuring heated floors for those chilly mornings. The 2-car garage offers a fantastic surprise w/ a finished loft level that makes for an ideal home office or creative studio. The LL adds even more versatility w/ additional finished space and a full bathroom, bringing the home's total to 3 full baths. The outdoor space is a private retreat. After a long day, there is nothing better than heading to the secluded outdoor shower or hot tub in the backyard to unwind. Situated just blocks from the shoreline/ marina, this location offers the quintessential coastal lifestyle. Whether you are heading toward the water or strolling into town for dinner, everything that makes this community special is right at your fingertip

307 Old Post Rd, Fairfield
12 Sconset Dr, Fairfield
$1,525,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24177139 MLS
"The Yellow home on the corner", perfectly set on a prime University cul-de-sac, has hit the market. Welcome to 12 Sconset Drive, a home overflowing w/ character that is move-in ready, w/ thoughtful improvements & shows like a dream. Featuring 10 spacious rooms across 3 levels of living creating a special space for everyone, all filled w/abundant natural light. So many details to love about this home including built-ins, hardwood flooring, 3 updated full bathrooms, freshly painted & the list goes on. The main level offers an exceptional flow w/ the eat-in kitchen perfectly designed for both entertaining & cooking while the cozy living room w/ fireplace opens to the idyllic 3 season porch, the perfect spot for sipping morning coffee or relaxing to the sound of birds chirping. The dining room easily connects to the sunroom, a warm spot to unwind. A laundry area & half bath complete the main level. Upstairs, you will find 3 generously sized bedrooms, including the primary suite, along w/ a finished 3rd level featuring the 4th bedroom, family room & full bath, perfect for guests, a home office, or flexible living. Step outside to one of the home's most special features: a peaceful, private & expansive back yard bursting w/ blooming flowers, privacy trees, patio, fencing & professional landscaping. Enjoy the amazing block parties this neighborhood offers, walk to school, stroll to town & take advantage of dining, entertainment & shopping. Enjoy life in this exceptional home.

12 Sconset Dr, Fairfield
1495 Westport Tpke, Fairfield
$1,500,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24047873 MLS
Rich in character and designed for today's lifestyle, this distinctive Fairfield home is privately set on two picturesque acres, framed by classic New England stone walls, white fencing, mature trees, open lawns, a quintessential red barn, and a detached two-car garage. The setting offers exceptional privacy while beautifully balancing Fairfield's country landscape with the convenience of its location. Thoughtfully renovated and expanded in 2012, the home offers an elevated, modern living experience while preserving the architectural details that make the property unique. The beautifully appointed chef's kitchen, with top-of-the-line appliances, opens seamlessly to a great room with soaring vaulted ceilings, a handsome fireplace, walls of windows overlooking the property, and sliders to the private deck. Designed for both entertaining and everyday living, the open layout creates a natural gathering place and an effortless connection to the outdoors. Adding to the home's timeless character are its circa-1749 origins, beautifully preserved through select period details, including the King's Board flooring-an architectural feature traditionally found in some of New England's earliest homes. An adjoining room offers exceptional flexibility as a library, study, or intimate sitting room.

1495 Westport Tpke, Fairfield
236 Main St Unit 236, Fairfield
$1,500,000
1 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24196135 MLS ⋅ Southport Harbor BLDG.
A rare opportunity to own in the heart of historic Southport Village for under $1.5 million. Beautifully redesigned by the renowned Michael Greenberg & Associates of Westport, this sophisticated two-level residence is located within a landmark building overlooking Southport Harbor. Offering one of the few opportunities to own in Southport Village at this price point, it is ideally suited as a full-time residence or elegant weekend retreat, just a short stroll to the train, Pequot Yacht Club, village shops and restaurants, Southport Beach, the harbor, and everything that makes the Village one of Fairfield County's most sought-after coastal communities. The first floor features a spacious bedroom with a beautifully renovated full bath. Upstairs, an expansive living room, well-appointed kitchen, and powder room create an inviting space for both everyday living and entertaining. Large bay windows fill the home with natural light while capturing picturesque views of Main Street, Southport Harbor, and the Country Club of Fairfield golf course. Combining historic character, designer finishes, harbor views, and an exceptional walk-to-everything location, this is a truly rare opportunity to own a beautifully renovated residence in one of Connecticut's most coveted coastal villages.

236 Main St Unit 236, Fairfield
148 Szost Dr, Fairfield
$1,500,000
5 Beds ⋅ 7 Baths ⋅ CLOSED Status ⋅ 24191205 MLS
Completely reimagined from top to bottom, 148 Szost Drive offers the rare opportunity to own a move-in ready home on one of Fairfield's most sought-after neighborhoods. Thoughtfully renovated with today's lifestyle in mind, this 5-bedroom, 5.5-bath residence spans over 3,800 square feet on nearly a quarter-acre, blending timeless design with exceptional functionality. Designed for the way people live today, the home features an effortless flow between multiple living spaces and a beautifully renovated open kitchen that naturally becomes the heart of the home. Upstairs, spacious bedrooms include multiple en-suite baths, while the finished third floor offers exceptional flexibility with a bonus room, home office option, full bath, and comfortable space for guests. The extensive renovation extends well beyond the cosmetic updates, with significant investments including a new HVAC system, new radiant heat throughout the first floor, thoughtfully designed custom storage, and a beautifully reimagined second-floor laundry room. Every improvement was made with comfort, efficiency, and everyday living in mind, creating a home that feels as functional as it is beautiful. Outside, the private backyard offers plenty of room to relax, entertain, and play, while the attached garage includes an EV charger for added convenience. Ideally located just moments from Fairfield's beaches, downtown, train station, parks, & everything that makes the University neighborhood so desirable.

148 Szost Dr, Fairfield
485 Mountain Laurel Rd, Fairfield
$1,500,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24189763 MLS
Picture coming home to your own Custom Colonial sitting on over half a private acre on a quiet, tree-lined street in lower Greenfield Hill, where you're minutes from everything but feel worlds away. An expansive front porch invites you to slow down the second you pull in. Inside, sunlight pours through every room and hardwood floors gleam underfoot. The high-end, spacious kitchen is made for gathering - an oversized island, quartz counters, marble backsplash, and Thermador & Bosch stainless appliances bring everyone into one open, functional space. A separate office with custom built-ins and a fireplace offers a quiet retreat for work or reading. The vaulted family room opens straight onto a 3-season screened-in porch offering a continuous indoor/outdoor living space. Upstairs, retreat to your spacious and newly renovated primary suite built for rest. It features a spa bath, soaking tub, radiant heated floors, and a walk-in closet that actually fits everything. Three more bedrooms, each with custom closets, share an updated bath with granite countertops and double sinks. Custom interior wooden shutters, a premium-flooring 2-car garage, whole-house Generac generator, new A/C, new washer/dryer bolster this as a home where there is nothing left for you to do. Move-in ready, in one of the area's most sought-after neighborhoods served by award-winning schools. Come see it before someone else calls it home.

485 Mountain Laurel Rd, Fairfield
1091 Round Hill Rd, Fairfield
$1,500,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24155855 MLS
A University adjacent property that perfectly blends charm, character and opportunity in a premiere Fairfield location on Round Hill Road. Presented in this highly sought-after neighborhood, this home lives like a four bedroom with spaces and places for gathering in groups or peeling away to find a private reprieve. With a flexible layout this gem is for both savvy investors and those looking to make their walk to town dream home a reality. Recently refreshed with thoughtful updates, including a stunning chef's kitchen open to the dining room, the property offers a modernized and sophisticated appeal while retaining the vintage charm of the era. The upgrades provide a polished canvas, making it move-in ready while still leaving room for personalization and expansion. Whether you're envisioning a larger footprint or simply enhancing the existing layout or craving a custom spa like bath, the versatility here beckons the imagination. Situated minutes from Fairfield's vibrant downtown, beautiful beaches, and top-rated schools, this property delivers the best of suburban living with easy access to every convenience. Whether you're an investor seeking a fabulous opportunity in a prime area or a homeowner ready to move right in to their forever home, 1091 Round Hill Road offers the ability to love life now and create forever memories.

1091 Round Hill Rd, Fairfield
101 Brambley Hedge Cir, Fairfield
$1,500,000
5 Beds ⋅ 6 Baths ⋅ CLOSED Status ⋅ 24128652 MLS
Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury homes on manicured grounds. This sun-drenched five-bedroom, six-bathroom home has been freshly painted inside and out and features extensive millwork, gleaming hardwood floors, and floor-to-ceiling windows that flood the home with natural light. The open-concept layout is ideal for entertaining, centered around a fully renovated gourmet kitchen with high-end appliances, custom cabinetry, and a large island, flowing seamlessly into the great room and out to a spacious patio. Upstairs, generous bedrooms include a luxurious primary suite, while flexible living spaces throughout the home cater to modern lifestyles-perfect for hosting or working from home. The flat, private yard offers multiple outdoor entertaining areas and is complemented by a three-car garage. Enjoy privacy and elegance while being just minutes from the vibrant downtowns of Fairfield and Westport, as well as local beaches and train stations. This is luxury living with everyday convenience-completely turnkey and ready for it's new homeowners.

101 Brambley Hedge Cir, Fairfield
28 Michaela Cir, Fairfield
$1,499,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24155487 MLS
Amazing Beach location set on a sought-after cul-de-sac, seconds to park and ballfield, a quick stroll to both the beach and town PLUS a 4-bedroom, 8 room immaculate Colonial - Welcome to 28 Michaela Circle. This beautifully maintained classic Colonial's layout is ideal for everyday living and entertaining. Desired features include bright, sun-drenched & spacious rooms, pristine hardwood floors and high ceilings. The spacious eat-in kitchen seamlessly connects to a large family room and dining room and is ideally designed for hosting holidays and special occasions. The family room with wood burning fireplace connects to an equally sized living room, providing a room for everyone on the main level. Upstairs, four well-appointed bedrooms offer space and privacy, including an oversized primary suite complete with walk-in closets and a spa-inspired bathroom with a jacuzzi tub, double vanity and stall shower - the perfect place to wind down after a long day. A large two-car garage offers added convenience along with valuable storage space. Enjoy the wonderful lifestyle that this exceptional location provides; long walks on miles of sandy beaches, strolls into town for dinner or shopping, walk to the Fourth of July fireworks, the half marathon and fabulous block parties. Move right into this well cared for and ideally situated home in time for the Summer coastal festivities. 28 Michaela Circle presents an exceptional opportunity to enjoy the very best of Fairfield Beach.

28 Michaela Cir, Fairfield
164 Wakeman Rd, Fairfield
$1,499,000
5 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24152868 MLS
Nestled in Fairfield's highly sought-after University neighborhood, this exceptional home beautifully blends timeless vintage charm with a warm, modern aesthetic. Set on a private, arborvitae-lined property, the outdoor space features a stone patio and gas fire rock seating area. Inside, the inviting layout offers effortless flow and abundant natural light. The living room, anchored by a wood-burning fireplace and French doors to the patio, opens seamlessly to the dining room and sunny kitchen. The custom kitchen connects to a family room with soaring 10-foot ceilings & roaring stone fireplace. Spacious primary bedroom with vaulted ceilings, beams, bath with glass shower, soaking tub & walk-in closet is a lovely oasis. Guest room with ensuite bath & walk-in closet plus 2 additional bedrooms complete the 2nd level. 3rd level bonus area offers flexible space with 5th bedroom. The finished lower level provides versatility and extra living space. Additional amenities include, study, mudroom, 2 laundry rooms, irrigation system, 2 car garage and much more. Ideally located just minutes from vibrant Fairfield town center and train (1 mi), Beach (1.3 mi), Marina (1.1 mi), Tennis & golf. Waterfront community offering historic charm, dining, shopping, arts & 2 universities, just 50 miles from NYC.

164 Wakeman Rd, Fairfield
251 Winnepoge Dr, Fairfield
$1,485,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24123493 MLS
Nestled in the highly sought-after enclave of Lake Hills in Fairfield, this extraordinary Colonial has been completely reimagined, torn down and masterfully rebuilt to blend timeless architectural charm with modern sophistication. From the moment you arrive, the home's undeniable curb appeal captivates, featuring a welcoming wraparound porch, professional landscaping, flower boxes and a full irrigation system that frame the picture-perfect setting. Inside, an airy open floor plan combines effortless flow with thoughtful design. At the heart of the home is a chef's kitchen, showcasing custom cabinetry, an oversized island, and top-of-the-line Thermador panel-front appliances equally suited for casual family dinners or elegant entertaining. With four spacious bedrooms, including a desirable first-floor bedroom, and three full baths, the home offers flexibility to suit a variety of lifestyles. A generous family room above the garage provides a comfortable retreat, while the finished walk-up attic and fully finished basement with ample storage create versatile spaces perfect for a gym, media room, or playroom. The primary suite is a serene sanctuary, complete with a spa-inspired bath, with radiant heated floor and designer finishes that elevate everyday living into an experience of pure comfort and luxury. Beyond the home itself, residents enjoy access to the Lake Hills Association, one of Fairfield's most beloved private communities...

251 Winnepoge Dr, Fairfield
20 Whetstone Hill Ct, Fairfield
$1,460,000
4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24194833 MLS
Some homes simply grow with you - and this is one of them. Nestled on a quiet cul-de-sac in a sought-after beach neighborhood, this inviting home has been the backdrop for years of cherished memories. Designed with both comfort and flexibility in mind, its thoughtful layout easily adapts to changing lifestyles. A legal studio - with a private entrance, full bathroom and kitchenette - offers exceptional versatility, ideal for extended family, guests, a home office, an au pair, or potential rental income. Step outside to the private backyard and inviting patio, the perfect setting for morning coffee, outdoor entertaining, or unwinding after a day at the beach.Ideally located just minutes from the beach, vibrant downtown Fairfield, the Metro-North train station, shopping, restaurants, parks and top-rated schools, this home combines timeless charm with everyday convenience. Whether you're looking for a place to put down roots, accommodate a changing lifestyle, or enjoy Connecticut's coastal living at its best, this exceptional home is ready to welcome its next owners.

20 Whetstone Hill Ct, Fairfield
478 Hulls Hwy, Fairfield
$1,455,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24132888 MLS
A picturesque, expanded and impeccably renovated Cape Cod home located in highly desirable Southport (set off far from road) awaits. Welcome home to 478 Hulls Highway where the character of this Cape blends with today's must have updates. This sun-drenched home features two levels of living, 8 spacious rooms including 3 bedrooms and 2.5 beautifully renovated baths. A rare main level primary suite adds to the convenience and appeal of this special property. Set on an expansive 1.0 acre lot this home has been meticulously updated throughout. Recent home improvements include: all new bathrooms with high-end finishes, renovated eat-in kitchen with new Quartz countertops, new appliances, new backsplash and painted cabinetry, entire interior has been freshly painted, new lighting and hardware throughout, striking new granite hearth fireplace, new central air system, updated plumbing fixtures and a newly paved driveway. The open and flexible floor plan allows for comfortable everyday living & effortless entertaining. Unfinished lower level is ideal for great storage or future home expansion with 864 sf. Attached two car garage provides easy entry into home. Flooded with natural light and filled with charm this home truly has it all. Step outside to a private and peaceful backyard with patio and great space to unwind or host guests. Ideally located and just minutes to Southport Village, beaches, the harbor, top-rated schools and train access - everything you need is at your doorstep!

478 Hulls Hwy, Fairfield
1835 Cross Hwy, Fairfield
$1,450,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24205655 MLS
Set on 2.46 picturesque acres in coveted Greenfield Hill, this modernized farmhouse Colonial combines classic character, thoughtful updates and an exceptional piece of property. Beautiful stone walls frame expansive open lawns, while a newer front porch with copper roofing adds to the home's timeless farmhouse appeal. Just under 3,000 SF of above-grade living space features hardwood floors, detailed millwork, multiple fireplaces and a wonderfully flexible floor plan. The remodeled kitchen is the heart of the home w/ quartz counters, large center island, custom cabinetry and a high-end appliance package including Sub-Zero & Wolf. An adjacent wet bar with wine refrigeration is ideal for entertaining. The kitchen opens to a spacious living area anchored by a dramatic fieldstone fireplace. A formal dining room w/ fireplace and separate family room with vaulted ceiling and exposed beams. A standout feature is the main-level in-law potential: private entrance, bedroom, bonus room / access to a full bath-ideal for guests or an au pair. Upstairs are the spacious primary bedroom, 2 additional bedrooms and full bath. Outside, a stone patio & covered porch overlook the home's incredible grounds. Broad, field-like lawns, mature trees and extensive stonework create a true estate setting-a remarkable property to enjoy for decades to come. New roof / gutters in '26. A special Greenfield Hill home combining modern updates, versatile living space and a property that is truly unforgettable!

1835 Cross Hwy, Fairfield

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