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3050 Bronson Rd, Fairfield
$2,495,000
4 Beds ⋅ 4 Baths ⋅ 24186223 MLS
A Connecticut Classic - this center hall Colonial is located on the most charming stretch in Greenfield Hill. Beautifully set on 2 acres, this 4 bedroom Jack Franzen designed home lives large in all aspects. Guests are welcomed into the double height foyer flanked by formal living and dining rooms. The great room spans the back of the house combining a gorgeous light, bright & well appointed kitchen, with a cozy family room w/ traditional fireplace & plenty of room for gathering & lounging, a dining area and a cozy window seat - and easy access to the huge recreation room set over the garage! The first floor also holds a lovely library room with another fireplace, beautiful, oversized windows facing both front and back views and custom built-ins. Upstairs, the primary bedroom is spacious and light-filled, with a recently renovated bath and walk in closet. There is an ensuite bedroom plus two additional bedrooms sharing a hall bath. Outdoor living is maximized with two deck spaces and a pretty patio, perfect for entertaining, grilling and enjoying the privacy of the gorgeous, fenced in grounds! True New England character is felt throughout, from the rich hardwoods, charming wainscotting & coastal chic kitchen to the historical neighborhood setting - imagine spring days on the green celebrating the Dogwood Festival, sounds of baseball being played at the nearby diamond all while also being centrally located to all Fairfield amenities like beach, town and train to NYC!

3050 Bronson Rd, Fairfield
109 Smith St, Fairfield
$2,495,000
4 Beds ⋅ 5 Baths ⋅ 24133085 MLS
The beach house that truly has it all - light, luxury & location. Set on a nearly 1/4 acre lot on one of Fairfield Beach's most coveted, low-traffic streets where neighbors still host block parties & bike to the shore, this 4-5 BR, 4 1/2 BA home captures the spirit of coastal living w/timeless Nantucket style & effortless sophistication. Inside 9-ft ceilings & natural light define the main level. Living room w/wood beamed ceiling & gas fireplace faces dining room w/coffered ceiling that glows in afternoon light. A deep, moody designer powder room makes a bold statement while the show-stopping navy wet-bar w/warm wood counters, glass cabinetry & beverage fridge connects the dining room & kitchen - an entertainers dream. Chefs kitchen w/custom cabinetry & marble island opens to family room w/stone fireplace & built-ins overlooking the backyard retreat: heated pool w/automatic cover, expansive patio & lush landscaping. 2nd level offers a stunning guest suite, home office & large laundry room. Above, the primary suite is a sanctuary w/large walk-in closet & sublime bath redesigned by celebrated Fairfield County designer w/dual vanities, window seat, soaking tub, oversized marble shower & water closet. Two add'l BRs share a chic Jack-and-Jill bath. Top floor delivers huge finished flex room w/full bath perfect for home gym, playroom or guest suite. Oversized attached 2 car garage, mudroom w/custom built-ins, irrigation, tons of storage, gas, sewer, FEMA compliant. A coastal dream!

109 Smith St, Fairfield
400 Bronson Rd, Fairfield
$2,450,000
5 Beds ⋅ 5 Baths ⋅ 24124894 MLS
Discover refined waterfront living at 400 Bronson Road. A beautifully crafted custom colonial set along the peaceful Mill River in Southport. This elegant waterfront home offers five generously sized bedrooms, four and a half bathrooms, and over 4,000 square feet of thoughtfully designed space across four levels. High-end finishes and timeless design details shine throughout, from the white oak accents and grand glass-railed foyer to the chef's kitchen featuring quartz countertops and premium appliances. The open layout is ideal for both everyday living and entertaining, featuring the floor to ceiling glass enclosed wine room and multiple balconies, inviting you to relax and take in the scenic river views. The luxurious primary suite offers a private retreat complete with a spa-like bathroom and its own balcony overlooking the water. Perfectly positioned just minutes from Southport's beaches, golf courses, vibrant shops and restaurants, this home blends sophistication and comfort, and natural beauty in one of Fairfield's most sought-after locations.

400 Bronson Rd, Fairfield
57 Beaumont Pl, Fairfield
$2,425,000
5 Beds ⋅ 6 Baths ⋅ 24171536 MLS
Nestled at the end of a peaceful cul-de-sac on a level lot, this exceptional 5,000 Square foot, 5-bedroom, 5.5 bath residence offers 4 levels of thoughtfully curated luxury living. Designed with both elegance and functionality in mind, the home seamlessly blends high-end finishes with everyday comfort. Upon entry, the main level features a bedroom or private office with a full bath-ideal for guests or multigenerational living. The chef's kitchen is a true showpiece, complete with custom cabinetry, professional-grade appliances, quartz countertops, and an oversized center island. The adjoining living area is perfect for entertaining, highlighted by a sleek gas fireplace and a stunning glass-enclosed wine display. The second level hosts four generously sized bedrooms, including two connected by a Jack-and-Jill bath, a third with its own en-suite. The primary suite offers an expansive walk-in closet and a spa-inspired bathroom with a soaking tub and refined designer finishes. The third floor provides versatility with a bonus space along with an additional full bath. Completing the home is an expansive lower level with 9 foot ceilings featuring two additional rooms and a half bath, ideal for a home theater, fitness area, or recreation space. Enjoy the best of Fairfield living in a vibrant walkable neighborhood just moments from the town center, upscale dining and lively nightlife. Conveniently located within walking distance to the train and offering easy access to major highways

57 Beaumont Pl, Fairfield
260 Range Rd, Fairfield
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 24161505 MLS
260 Range Road is a home that feels instantly timeless. An elegant Connecticut Colonial w/stately, time-softened brick exterior, set back at the end of a quiet cul-de-sac in one of Southport's most coveted neighborhoods. Peaceful & private yet minutes to downtown Fairfield, Westport, Metro North & everyday conveniences this home offers both serenity & connection. In a neighborhood where neighbors still ride bikes in the street, the home offers a rare sense of calm & community. Inside, soaring ceilings, oversized windows & abundant natural light define the interiors. Each room is generously proportioned w/9-foot ceilings & classic craftsmanship throughout. The main level balances elegance & comfort w/formal living & dining rooms, a handsome office & dramatic great room w/soaring double-height ceilings & wood-burning fireplace. The kitchen is both refined & inviting, featuring rich stone countertops, premium appliances, center island, sunny breakfast area w/door to expansive bluestone patio. Upstairs the primary suite offers a true retreat w/sitting area, office/nursery, 3 walk-in closets & en-suite bath. 3 additional bedrooms are generously sized, offering comfort & flexibility for family & guests. The finished walk-out lower level adds exceptional versatility w/space for a playroom, gym, media room or guest room all leading to a gorgeous flat lawn and backyard oasis. Laundry room, attached 3-car garage, abundant storage, gas, sewer. A rare Southport offering.

260 Range Rd, Fairfield
96 Clinton St, Fairfield
$2,355,000
4 Beds ⋅ 4 Baths ⋅ 24175731 MLS
Stunning new construction just steps to the beach, offering the perfect blend of luxury, comfort, and coastal living. This beautifully designed 4-bedroom, 3.5 bath home features approx. 2550 sq feet plus an additional 400 Square feet of finished loggia space, ideal for 3 seasons entertaining. The open concept main level showcases a custom chef's kitchen with quartzite countertops, large island with 2 inch countertops, gorgeous high-end finishes and seamless flow into the spacious dining area and family room featuring oak beamed ceilings, gas fireplace and an inviting entertainment and bar area, plus shelving and built-in cabinetry abutting the gorgeous stone fireplace. Perfect setting for gatherings with family and friends. The third floor bedroom/office has a full bath with walk in shower, and opens to a spectacular deck with wire railings and beautiful views- the perfect retreat for relaxing or working from home. The lower level loggia offers exceptional additional living space complete with custom built-ins, large-screen tv hookup, and direct access to the patio and backyard with room for a pool. Additional highlights include hardwood floors throughout, custom moldings and millwork, designer baths, a large mudroom, and a 2 car garage underneath. Incredible storage. Coastal elegance and thoughtful craftsmanship shine throughout this exceptional beachside home. Walk to town, shops, school, restaurants, park, marina and beaches are steps away

96 Clinton St, Fairfield
2775 North St, Fairfield
$2,350,000
5 Beds ⋅ 8 Baths ⋅ 24128629 MLS
Crafted by noted custom builder Garrett Wilson and meticulously enhanced with recent upgrades, this Greenfield Hill home is as impressive as it is inviting. Finished to the highest standard, the residence is set on just over two private acres with a tennis court and expansive open space offering room for a pool and pool house. At the heart of the home, the chef's kitchen is filled with natural light and outfitted with Wolf and Sub-Zero appliances, two farmhouse sinks, two dishwashers, two wine refrigerators and a beautifully refinished wood island. Upstairs, you will find 5 bedrooms, all en-suite with walk-in closets and a spacious laundry room. The primary suite provides a serene retreat with his and hers walk-in closets and a spa bath with steam shower. The finished top level is ideal for an in-law or au pair suite with full bath and sweeping property views. The lower level offers a warm entertaining space with fireplace, a home gym, an additional flex room to be used as a playroom, bedroom or office, and an additional laundry room and full bathroom. Deer fencing encircles the entire property, with a gated entrance for enhanced security and privacy. Enjoy the ease of town water and natural gas utilities. Other recent updates include a new roof, new HVAC system and boiler with expansion tank. The property is convenient to Fairfield and Westport town centers and is commuter friendly to Manhattan. Truly a remarkable offering in sought-after Greenfield Hill.

2775 North St, Fairfield
165 Hemlock Hills Rd S, Fairfield
$2,335,000
5 Beds ⋅ 4 Baths ⋅ 24159832 MLS
Enchanting countrystyle retreat offering the warmth of a welcoming neighborhood with the luxury of natural privacy, nestled amid professionally landscaped gardens and mature trees. Designed for gracious living and effortless entertaining, 165 Hemlock Hills S blends refined upgrades with modern comfort throughout. Featuring two primary suites, five bedrooms, and four beautifully renovated baths, the home centers around a stunning NuKitchens renovation with custom Plain & Fancy cabinetry, SubZero column refrigerator and freezer, quartz countertops, island and banquette seating, plus new laundry room. Enlarged doorways invite sunlight and frame serene pool and garden views, creating a seamless indoor/outdoor connection. Multiple living spaces support every lifestyle moment: a fireside living room, dramatic dining room, family room with stone fireplace, sunroom wrapped in windows, and a media room with beverage bar. New trim, lighting, and elevated decor add quiet sophistication throughout. Basement playroom offers flexible space. Outside, the resort-inspired backyard is a private escape, with newer Trex deck and fences, poolside patio, fire pit for evenings into late fall, winding gravel paths, and lush seasonal landscaping. Well water available for pool; home has city water. Newer driveway, roof, furnace, water purification system. Peaceful, private, and beautifully connected-just five minutes to Trader Joe's and highway access. A home for how you live today.

165 Hemlock Hills Rd S, Fairfield
298 S Benson Rd, Fairfield
$2,320,000
4 Beds ⋅ 5 Baths ⋅ 24180716 MLS
Savor the coastal lifestyle in this beautifully designed, light-filled home in Fairfield's sought-after Beach neighborhood. Ideally located just a half-mile stroll from Jennings Beach, Jennings Pavilion, the Fairfield Marina, and Sand Castle park, this home offers the perfect blend of comfort & convenience. The open-concept main level features a spacious living room that flows seamlessly into the dining area, kitchen, and family room. French doors open to a private patio with custom pergola and beautifully landscaped property. The well-appointed kitchen is the heart of the home, featuring marble countertops, a 48" Viking double-oven range & a generous walk-in pantry. A wet bar with dual beverage coolers adds convenience for entertaining. The sun-filled office offers custom built-ins & worktable, while a mudroom completes the main level. Upstairs, the primary bedroom includes two walk-in closets & a lux en-suite bath highlighted by a double shower. 3 additional bedrooms each feature walk-in closets & private en-suite baths. A full laundry room completes the second floor. The airy third level provides flexibility, offering a bonus room ideal as a family room, office or 5th bedroom, along with full bath & balcony. Amenities include solar panels, EV charger, central vac & irrigation system. Enjoy a prime location less than a half-mile from shops & restaurants, just minutes from Fairfield's vibrant town center, train, golf, tennis. Waterfront community just 50 miles from NYC.

298 S Benson Rd, Fairfield
1054 Mill Plain Rd, Fairfield
$2,300,000
5 Beds ⋅ 5 Baths ⋅ 24190793 MLS
Welcome to 1054 Mill Plain Road! Exceptional craftsmanship and timeless design define this impressive center hall NEW CONSTRUCTION colonial! This open-concept floor plan is designed for seamless everyday living and effortless entertainment boasting 5,518 sq ft of living space and privately set on a rear lot in the sought-after Fairfield University neighborhood. This home presents 5 bedrooms, 4.5 baths, 9' ceilings, and hwd flrs throughout. Impeccable details include a gourmet designer kitchen with a sprawling quartz island, thermidor appliances, floating shelves, butler's pantry, with an abundance of recessed and natural lighting. An elegant archway flows into a family room with a fieldstone gas fpl with floor to ceiling sliders lending itself to a fenced in backyard, decking and patio for all your outdoor entertainment gatherings. Elegant formal dining room showcases exquisite millwork, intricate trim details, and a distinctive architectural ceiling. The MBR suite features a gas fireplace, lighted tray ceiling, with a beautifully designed spa bath. Two of the bedrooms are jack and jill with an appointed shared full bath. There is a 3rd floor finished area that provides recreational space for versatile usages such as an au pair, gym, studio, office, and/or guest retreat. This home offers a peaceful escape while remaining just minutes from Fairfield's beaches, train stations, vibrant downtown, shopping, dining, and top rated schools. Experience luxury living at its finest

1054 Mill Plain Rd, Fairfield
360 Duck Farm Rd, Fairfield
$2,299,000
5 Beds ⋅ 7 Baths ⋅ 24165339 MLS
Cast one's eyes upon this special setting and you're instantly reminded of Mark Twain's quote... "Buy land, they're not making it anymore!" Picture perfect, sanctuary view, expansive level lawn, located in the heart of Fairfield. Magnificent new home built by one of the towns most prominent tradesman. Architecturally stunning turreted and stone enhanced Colonial design. Gracious open floor plan incorporating the finest in craftsmanship, integrity, modern amenity and high grade building components. Special features include a Family Rm w/ FP, adjoining Den and dedicated Home Office, Chef's Kitchen w/ all the trimmings, and a luxurious Primary Bedroom Suite w/ Sitting Rm. A finished attic or Third Floor provides a large Bonus Rm, Full Bath, and optional 5th & 6th Bedrooms. The full unfinished basement offers convenient exterior access, ample storage, and potential for more living space. Fairfield is a thriving community enjoying top ranked schools, miles of sandy beaches, and an array of shopping, dining, cultural and recreational resources. The town is proximate to all major employment centers and enjoys easy access to commuter services & major transportation routes. Come discover your perfect lifestyle match!

360 Duck Farm Rd, Fairfield
66 Gate Stone Ln, Fairfield
$2,256,600
4 Beds ⋅ 7 Baths ⋅ 24169966 MLS
Welcome to 66 Gate Stone Lane, a quintessential Connecticut estate in the heart of historic Greenfield Hill. A gated entrance introduces this private 3.8-acre property, ideally positioned at the end of a quiet cul-de-sac among other distinguished homes. A gracious stone path leads to a double-height foyer, setting the tone for the home's refined architectural details and thoughtfully updated interiors. The formal living room features a fireplace, custom built-ins, and French doors opening to an outdoor dining area. A wood-paneled library with parquet floors offers serene views of the garden pond, while the elegant dining room flows seamlessly into a warm and inviting family room with fireplace and direct access to the patio. The home has been extensively and thoughtfully renovated throughout, including a completely redesigned chef's kitchen featuring custom cabinetry, high-end finishes, and the addition of a striking fireplace-creating a true heart-of-the-home gathering space. New hardwood floors run throughout, complemented by updated powder rooms and a state-of-the-art water filtration system. Upstairs, the expansive primary suite has been fully reimagined, offering a luxurious bedroom retreat with built-ins and window seat, along with a spa-caliber bath finished to the highest standard. Three additional guest bedrooms and a versatile additional room with Palladian windows-ideal for office or play-complete the second level.

66 Gate Stone Ln, Fairfield
127 Paul Pl, Fairfield
$2,250,000
5 Beds ⋅ 6 Baths ⋅ 24129954 MLS
The house that dreams are made of-nestled in a walkable community near beach, quaint town center and train. Brand-new construction recently completed, offers a seamless blend of understated elegance & coastal vibe. Fabulous 1st floor open floor plan features 9' ceilings and all generous size rooms: an inviting foyer, private mudroom, gourmet kitchen with 8' Quartz Island for entertaining. Top of the line Thermador appliances: 48" Gas 6 burner dual fuel convection range, 7' French door refrigerator, French Allia farmsink, dining area. Modern day "Keeping Room" adjoins the kitchen for cozy gatherings w/ Sliders to a covered deck for BBQ, generous Family room w/gas fireplace, formal living room, formal dining room w/panel molding. A walk through butlers pantry with wet bar and wine cooler, huge pantry and powder room complete the first floor. Custom shaker style cabinetry, exquisite moldings including ship lap and panel moldings throughout. Upstairs you'll find 4 ensuite bedrooms including a stunning Primary suite, impresses with vaulted ceiling and dreamy 11' x 12' walk-in closet. Spa-like luxurious primary bath has radiant heat floors, Rohl fixtures, pedestal soaking tub, frameless glass shower. 3rd floor has a 5th bedroom, full bathroom and extra playroom. Every closet is thoughtfully outfitted. Garage level has a 2nd mudroom, parking for 3 cars with Loggia area and ample storage. Experience your private oasis-designed for comfort, entertaining and luxury.

127 Paul Pl, Fairfield
1417 Fairfield Beach Rd, Fairfield
$2,240,000
3 Beds ⋅ 3 Baths ⋅ 24154311 MLS
Set along 48 feet of direct sandy shoreline on Fairfield Beach, "Witching Waves" is a two-parcel offering that pairs classic coastal character with expansion flexibility. The primary 0.18-acre beachfront lot at 1417 Fairfield Beach Road is complemented by a separate 0.07-acre creek-side parcel at 1418, creating a distinctive ownership opportunity along Long Island Sound. Originally built in 1917, this 1,410-square-foot cottage blends historic charm with everyday comfort. The three-bedroom, two-and-a-half-bath layout features tile flooring on the main level, wood flooring upstairs, and a wood-burning fireplace that anchors the living space. A split air conditioning system provides seasonal balance. The front porch faces the water, offering uninterrupted shoreline views and direct beach access just steps away. A dedicated grill area supports outdoor entertaining in a natural beachfront setting with no seawall. Off-street parking is located directly in front of the home. Approximately 1 mile to Penfield Beach and about 2 miles to downtown Fairfield and the Fairfield Train Station with Metro-North service, the property combines coastal privacy with convenient access to town amenities. A refined opportunity to secure direct Fairfield Beach frontage with the added benefit of a second parcel at 1418 Fairfield Beach Rd.

1417 Fairfield Beach Rd, Fairfield
631 Reid St, Fairfield
$2,225,000
6 Beds ⋅ 6 Baths ⋅ 24165022 MLS
Welcome to this stunning new construction farmhouse colonial in Fairfield's coveted University area, offering modern luxury, timeless design, and a rare backyard oasis complete with a beautiful in-ground pool. Thoughtfully crafted with exceptional attention to detail, this 6-bedroom home delivers the perfect blend of style, comfort, and functionality. Step inside to bright, open concept living spaces ideal for both everyday living and entertaining. The gourmet kitchen features premium appliances, an oversized island, custom cabinetry, and a walk-in pantry, flowing seamlessly into a spacious family room with a gas fireplace and views of the pool and patio. A dedicated first-floor office provides an ideal work-from-home setup, while a large bonus room offers endless versatility-playroom, media room, fitness space, or guest suite. With six generously sized bedrooms, including a serene primary suite with a spa inspired bath, there's room for everyone to live, work, and unwind. Outside, enjoy your own private retreat: a with an in-ground pool, stone patio, and fenced yard perfect for summer gatherings, relaxation, and fun. Perfectly situated close to Fairfield's beaches, vibrant downtown, top-rated schools, and the train, this home offers exceptional convenience while maintaining the charm and community feel that define the University neighborhood.

631 Reid St, Fairfield
158 Coventry Ln, Fairfield
$2,225,000
4 Beds ⋅ 4 Baths ⋅ 24151483 MLS
Step into the epitome of elegance & comfort at 158 Coventry Lane, a stunning Connecticut Colonial located in the prestigious Greenfield Hill area of Fairfield. Beautifully sited on a vibrant cul-de-sac, this turn-key home offers an unparalleled lifestyle in a serene, picturesque setting. Set on 2 acres of level grounds, this property is a true sanctuary w/impeccably landscape, stone walls, a bluestone patio & walkways, a heated saltwater pool & spa, enclosed vegetable garden & pool house. It's the perfect retreat for both relaxation & year-round entertainment. Inside, sophistication meets functionality. A dramatic triple-height foyer w/herringbone floors greets you, setting the tone for the 4,244 sq feet of updated living spaces. The layout is designed for both large gatherings & everyday comfort. The family rm, with its vaulted ceiling & floor-to-ceiling fieldstone fireplace, flows seamlessly into a private den/media room complete with a wet bar. The elegant living rm, featuring a beautiful gas fireplace, opens to a versatile office, playroom or guest suite w/an adjacent full bath. The heart of the home is a sleek modern kitchen, boasting a 9-foot quartz island, wine fridge & panoramic views of the backyard oasis. Upstairs, the primary suite is a private retreat w/a dramatic fireplace & spa-like bath. 3/4 addt'l bedrooms, and a private home office ensure space for every need. Only 8 mins to downtown Fairfield train station, shopping and dining.

158 Coventry Ln, Fairfield
677 Eleven O Clock Rd, Fairfield
$2,220,000
5 Beds ⋅ 5 Baths ⋅ 24158322 MLS
SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM MONDAY 3/16. Set on two private, park-like acres in one of Fairfield's most sought after neighborhoods, this beautifully updated home offers over 4,000 square feet of thoughtfully designed living space with 5 bedrooms and 4.5 baths, including a dedicated home office for today's flexible lifestyle and gunite pool. The heart of the home is a chef's kitchen featuring custom inset cabinetry, an oversized center island with prep sink and Sub-Zero refrigerator drawers, a Wolf range, and generous space for cooking and gathering. Just beyond, a sun-filled dining room opens through patio doors to a bluestone terrace and pool, creating a seamless indoor-outdoor setting for entertaining. A dramatic two-story foyer is flanked by both a formal living room and a spacious family room with wood-burning fireplace, offering multiple spaces for everyday living. The main level also includes a fully equipped laundry room, a bright three-season sunroom, and a mudroom off the three-car garage. Conveniently located just off the mudroom is a full bath-perfect for rinsing off after an afternoon by the pool. Upstairs, the primary suite offers a true retreat with a brand-new spa-inspired bath and dual walk-in closets. This floor features four additional bedrooms. An unfinished walk-up third floor and massive lower level provides excellent potential for additional living space.

677 Eleven O Clock Rd, Fairfield
820 Hillside Rd, Fairfield
$2,215,000
3 Beds ⋅ 3 Baths ⋅ 24168800 MLS
Comfort, style, and luxurious one-level living converge in this beautifully redesigned home, ideally located in lower Greenfield Hill. An enchanting architectural facade sets the tone for a residence defined by exceptional craftsmanship and refined finishes throughout. The open floor plan is anchored by a stunning family room with soaring cathedral ceiling, dramatic fireplace, and French doors that open to the patio--perfect for indoor/outdoor living. The chef's kitchen is stylish and functional, featuring custom cabinetry, a central island, and a sleek breakfast bar. An informal dining room or office, wrapped in windows on three sides and with heated tile floors, flows effortlessly into the formal dining room. A striking marble-topped bar adds a sophisticated touch, creating an ideal setting for entertaining. The primary suite offers a five-star retreat, highlighted by a recently renovated marble spa bath, with heated floor, custom cabinetry and closets. Additional bedrooms are generously proportioned. Enhancements include a well organized mudroom with built-in storage; skylights to add natural light; and a cozy, spacious lower level. Set on spectacular grounds with sweeping front and rear lawns, curated landscaping, and a stone patio with sitting wall and outdoor fireplace, this property offers an exceptional backdrop for relaxed living and sophisticated entertaining. Conveniently close to town amenities, 820 Hillside is an outstanding opportunity in a dream neighborhood.

820 Hillside Rd, Fairfield
320 Warner Hill Rd, Fairfield
$2,210,000
5 Beds ⋅ 3 Baths ⋅ 24160667 MLS
Location, space and timeless design come together in this beautiful 5 Bedroom Colonial set on 1.48 acres in one of Southport's most desirable neighborhoods. This home offers the ideal balance of privacy and convenience. hardwood floors, custom moldings, and a coffered ceiling highlight the inviting main level. The Family Room with 9-foot ceilings and a gas fireplace opens to the Eat-In-Kitchen featuring a large center island, granite countertops, and stainless steel appliances - ideal for everyday living and entertaining. A formal Dining Room with raised paneling and a gracious Living Room with fireplace create elegant gathering spaces. Upstairs, the Primary Bedroom Suite offers cathedral ceiling, gas fireplace, Dressing Room, Full Bath. Four additional Bedrooms, Hall Bath and convenient 2nd floor Laundry complete the upper level. The screened porch overlooks a private backyard, perfect for relaxing or entertaining. A rare Southport Gem!

320 Warner Hill Rd, Fairfield
204 Glen Ridge Rd, Fairfield
$2,210,000
5 Beds ⋅ 5 Baths ⋅ 24154752 MLS
PLEASE SUBMIT HIGHEST AND BEST BY 5PM MONDAY 3/2. Tucked within Fairfield's coveted Lake Area, this newly built home offers a peaceful retreat where nature and design meet. Surrounded by mature trees and set on a scenic stretch just moments from Lake Mohegan, neighborhood beaches, and downtown amenities, the setting feels tranquil and removed while remaining effortlessly connected. Set on .46 acres with seasonal water views from select rooms, the property captures the quiet rhythm of lake living-morning walks beneath a canopy of trees, evening sunsets through oversized windows, and cozy nights by the fire. Inside, moody, custom-caliber finishes create warmth and depth rarely found in new construction. Nine-foot ceilings, solid core doors, and detailed millwork elevate every space. The kitchen anchors the main level with a 36" gas range, walk-in pantry, and generous island seating, flowing seamlessly into a dramatic color-drenched family room with wood ceiling and beams and a Taj Mahal quartzite fireplace. The home offers five bedrooms plus a finished bonus room above the garage that qualifies as a sixth bedroom, providing flexibility for guests, office space, or recreation. The primary suite offers a spa-like escape with heated floors, soaking tub, and oversized glass shower. An expansive stone patio and private rear yard invite outdoor living, with room for a future pool. A refined, design-forward home in a setting that truly feels like an escape.

204 Glen Ridge Rd, Fairfield
99 Acorn Ln, Fairfield
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 24160414 MLS
Welcome to 99 Acorn Lane, a desirable Southport address set on a quiet cul-de-sac just minutes to Westport, Southport Village, and Downtown Fairfield. This expanded Cape sits on 1.24 beautiful acres, offering privacy within a charming neighborhood and ample opportunity for expansion or a pool, subject to approvals. Thoughtfully upgraded, the home offers more than 3,000 square feet of flexible living space with 4 bedrooms, 3.5 baths, 2 fireplaces, and hardwood floors through most of the house. The main level is the heart of the home, with an inviting open layout, soaring ceilings, and an eat-in kitchen overlooking two spacious living areas with fireplaces. A pretty dining room, with oversized windows, is currently used as a study. A first-floor primary suite features a walk-in closet and full bath, while the second floor includes two additional bedrooms and a shared bath. Above the garage, a bonus bedroom with full bath offers flexible space for guests or work. A screened porch overlooks the property for enjoying warmer months. At the cul-de-sac, Aspetuck Land Trust's Acorn Lane Upland Preserve offers wooded trails connecting to Fairfield's Mill Hill Open Space. A rare Southport opportunity with space, charm, and convenience.

99 Acorn Ln, Fairfield
115 Fern St, Fairfield
$2,175,000
5 Beds ⋅ 3 Baths ⋅ 24149832 MLS
Charming, warm, and inviting from the moment you arrive. Just four blocks from the beach and an easy walk to town and the train, 115 Fern Street offers a home that lives easily year-round. Light moves naturally throughout, most notably in the sun-filled family room, where large windows and a cozy fireplace create the place everyone gravitates toward, from bright mornings to quiet evenings. The layout is comfortable and well-proportioned, with gracious living and dining rooms, two fireplaces, and a sense of quality that's felt rather than announced. The dining room carries a calm, serene presence, well suited to both everyday living and lingering meals. Outside, the yard is unusually large for a beach-area location and notably flat and dry, even after heavy rains, offering truly usable outdoor space in every season. Sherman School sits just across Beach Road, close enough to walk, yet removed from school traffic along this peaceful stretch of Fern Street. A home defined by light, comfort, and ease, 115 Fern Street offers beachside living that genuinely feels like home.

115 Fern St, Fairfield
114 Lee Dr, Fairfield
$2,170,000
4 Beds ⋅ 3 Baths ⋅ 24191108 MLS
Rare opportunity in Fairfield's sought-after Sasco Hill/South Pine Creek neighborhood, ideally located between town and the beach. Set on a private, level 1/3-acre lot bordering the Sasco Hill estates, this beautifully expanded and renovated home offers stylish finishes and an easy, open layout designed for today's lifestyle. The custom kitchen flows seamlessly into the dining area and inviting living room, where a wood-burning fireplace and French doors open to the patio and backyard. A versatile first-floor bonus room currently serves as a home gym but is equally suited as a home office, playroom, or fifth bedroom. Upstairs, the spacious primary suite features a large walk-in closet and beautifully appointed ensuite bath. Three additional bedrooms and a convenient second-floor laundry room complete the upper level. The expansive backyard is a true retreat with a stone patio, custom pergola, and perennial gardens offering exceptional privacy. Recent improvements include newer mechanicals, a Generac generator, and fresh interior paint. Enjoy an unbeatable location less than a mile from Sasco and Pine Creek Beaches, Southport Harbor, the train, golf, tennis, Fairfield's vibrant town center, and top local amenities. A rare bonus for this beach area location: the home is outside the flood zone, so no flood insurance is required. A wonderful opportunity to enjoy coastal living in one of Fairfield's most desirable neighborhoods.

114 Lee Dr, Fairfield
161 Sherwood Dr, Fairfield
$2,150,000
4 Beds ⋅ 5 Baths ⋅ 24178764 MLS
Enjoy the summer at 161 Sherwood Drive, a beautifully expanded and extensively updated residence located in the desirable Southport neighborhood. Offering approximately 3,679 square feet of thoughtfully designed living space, this home blends comfort, functionality, and inviting indoor-outdoor living in a private setting. The home features 4 spacious bedrooms, 4 full baths, and 1 half bath, including a sought-after first-floor primary bedroom suite that provides convenience and flexibility. The impressive great room serves as a standout feature, complete with a mahogany bar, stone fireplace, mounted TV area, and ample room for billiards and table games-creating an ideal setting for relaxing or hosting guests year-round. Designed for both everyday living and entertaining, the home showcases expansive gathering spaces filled with natural light. The screened-in porch extends the living space outdoors and provides a comfortable place to enjoy the surrounding private yard in multiple seasons. Outside, the in-ground pool and landscaped grounds create a peaceful retreat with space for entertaining, recreation, and outdoor dining. **962 sqft is the finished walk out lower level and included in total sqft.**

161 Sherwood Dr, Fairfield
16 Lookout Dr N, Fairfield
$2,150,000
6 Beds ⋅ 6 Baths ⋅ 24166699 MLS
Discover the breathtaking beauty and resort-style luxury of this exquisite, fully renovated 1914 Colonial - an architectural masterpiece overlooking the 16th hole of Brooklawn Country Club. This 6-bedroom estate, boasts 5,623 square feet across three sprawling levels, seamlessly blending historical grandeur with modern, lavish living. Period details abound, including custom millwork accentuating the superior craftsmanship of a bygone era. Generously proportioned rooms flow effortlessly, perfect for both grand entertaining and versatile daily life. The Gourmet Kitchen is a chef's dream, featuring premium quartzite counters, a large center island, and spacious dining/gathering areas. Additional highlights include a dedicated Office w/custom built-ins, a spectacular Family Room w/French doors and wet bar, AND a magnificent upper-level Great Room with soaring ceilings and authentic hand-hewn wood beams. The well-appointed Primary Suite serves as a private sanctuary, complete w/a newly renovated, spa-like bath and dressing room. Outside, your private haven awaits with resort-style amenities transforming you into the ultimate host. Whether planning an epic celebration or intimate weekend chill, this space delivers - a sparkling heated pool, full outdoor kitchen, sport court, stone fire pit, and expansive bluestone terrace. Enjoy sweeping views and unforgettable sunsets over the picturesque golf course. This is more than just a home, its a timeless legacy waiting to be claimed

16 Lookout Dr N, Fairfield
218 Lower Farm Rd, Fairfield
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 24149613 MLS
Highest and Best Bid Deadline Sunday, Feb. 1, by 9:00 pm. Offers will be reviewed on Monday, Feb. 2nd. New construction, Light, bright, sunny, pristine 4/5 bedroom, 4 full bath colonial built in 2025 on a beautiful cul-de-sac enclave of 7 new homes meticulously constructed by Sanddollar Development, known for their stellar designs, quality materials and next-level craftsmanship. Luxurious finishes, designer lighting, custom millwork, solid white oak flooring, spacious open-concept layout with great flow for entertaining and everyday living. Fabulously appointed chef's kitchen with separate pantry, wine fridge and large center island. Sliders from living room to covered deck for al fresco meals or relaxing with full view of the fenced backyard. First floor bedroom/office off foyer has full bathroom. Mudroom with storage cubbies and large walk-in coat closet/pantry leads to two car garage. Massive family room over the garage. Sumptuous primary suite with walk-in closet, gorgeous bathroom with double vanity, soaking tub, shower stall, w.c. Two ample bedrooms share large Jack 'n Jill bathroom with double vanities and two linen closets. Fifth large bedroom has ensuite bathroom. Laundry room on second floor. Entire third floor can be finished for future use. Finished lower level has sliders to covered patio and backyard. Professional landscaping, generator, city water, city sewer, natural gas, located close to town and train in the popular University area.

218 Lower Farm Rd, Fairfield
2444 Bronson Rd, Fairfield
$2,125,000
4 Beds ⋅ 4 Baths ⋅ 24189160 MLS
Classic charm on beautiful Bronson Road! A customized Colonial that overflows with extras - 4/5 bedrooms, open living spaces, play rooms, office/work zones, preserved historical touches and outdoor living options for all occasions! The main floor lives large. A formal living room, dining room, and sun room are on one side. While a huge front to back great room consisting of the kitchen, family room, play room, and the mudroom connection (complete with a built-in window seat) spans the other side. The breakfast bar has seating for 6, there is a dining area with full wet bar, a big stone fireplace with tons of room for gathering and lounging, plus access to the decks and patio beyond! Upstairs the primary suite is light and bright with vaulted ceilings, an oversized bath and a balcony. There are three generously sized bedrooms and a hall bath completing the second floor. On the lower level, walls of windows keep the rec room bright and sunny with tons of room to customize and the easy access to the outdoors is a bonus! At just under an acre, the property includes rolling lawns and plenty of privacy to enjoy all the space. There is a 2 car garage, and the central proximity to town, train schools and beaches is perfection!

2444 Bronson Rd, Fairfield
59 Thornhill Rd, Fairfield
$2,112,500
6 Beds ⋅ 6 Baths ⋅ 24101468 MLS
Located on one of the most coveted cul-de-sacs in Fairfield's University area, this Newly Built Colonial offers a perfect blend of classic charm & modern luxury. A welcoming stone-trimmed front porch sets the stage for quiet mornings with coffee, while inside, 5-7 bedrooms and 5.5 bathrooms provide ample space for comfortable living and entertaining. The gorgeous open-concept Kitchen with eating area flows seamlessly to the Family Room & features Thermador appliances, walk-in pantry & large Quartz island. Glass doors open to a spacious deck overlooking private, level backyard-perfect for BBQs, soccer games, or a future pool. The formal Dining Room is ideal for special occasions, & a versatile first-floor Office or Bedroom w/ closet & full bath offers flexible lifestyle options. Upstairs, the serene Primary Suite is a true retreat w/ two custom walk-in closets & a spa-inspired bath complete with soaking tub & oversized shower. Three additional Bedrooms, two full baths & a generous Laundry Room complete the second floor. The 3rd Level features a sunny Bonus Room ideal for a playroom, office, or creative space. Two additional bedrooms & full bath offer countless options for guests or family. Additional highlights include a 2-car garage leading to an oversized Mudroom w/ built-ins & a full walk-out lower level ready to be transformed: potential media room, gym, or in-law suite. This quality built home is set on a quiet, walkable street close to town, train, beaches & schools.

59 Thornhill Rd, Fairfield
2477 Bronson Rd, Fairfield
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 24191574 MLS
Nestled in the heart of historic Greenfield Hill, this special and timeless 1907 Queen Anne farmhouse provides an opportunity to own in one of the most desirable and coveted locations in Fairfield. The Clifford S. Banks house was once a farm where the owner raised turkeys, chickens, onions and bees. Situated on 2 acres of beautifully landscaped grounds that includes gardens and a barn- perfect for the equestrian family. This historic home has been thoughtfully expanded and restored over the last 40 years by the owners to maintain the old-world craftsmanship and provide modern comforts. As you approach the front entrance, you will be surrounded by an inviting screened porch and covered porches. A welcoming entry leads you to the inviting LR w/ expansive windows and wood burning fireplace, formal DR and FR w/ walls of built ins. The kitchen has been expanded to create a dining area w/ custom banquette seating and surrounded by windows providing an abundance of natural light. The kitchen was designed for a cook w/ attention to detail, design and function. The laundry room w/ ample storage and a Powder room complete the main level. The upper level has an inviting "sun parlor" which provides a cozy sitting area and office space. The primary bedroom features a comfortable retreat w/ walk-in closet and updated bath. There are 2 additional BRS and a hall bath. The spacious 3rd floor w/ architectural details and beams provide endless possibilities and storage. Full house generator.

2477 Bronson Rd, Fairfield
693 S Benson Rd, Fairfield
$2,100,000
4 Beds ⋅ 3 Baths ⋅ 24160315 MLS
Update: The seller has requested that highest and best offers be submitted by Monday 3/23 at Noon Life by LI Sound starts here, Welcome to 693 South Benson Road. This brilliantly redesigned & fully renovated in 2012, 4 bedroom, 3 bath home is set on a rare, private quarter acre. Light, clean, bright & fabulous is your immediate feeling upon entry. The living room flows seamlessly into the kitchen & continues into your dining area, creating an ideal layout for both entertaining & everyday privacy. The 1st floor also features a flexible bedroom & office, along w/ a mudroom & full bath. Hardwood floors throughout & freshly painted rooms complement the sun filled spaces. Upstairs, you will find a generously sized primary suite w/ walk-in closet and spa like full bath, 2 bedrooms & full bath. The finished 3rd floor offers added versatility, ideal as a workout room, playroom, or office plus an abundant storage room. Step outside to a private, fully fenced backyard featuring a new spectacular deck & patio, an outdoor shower & professionally landscaped grounds. From multiple vantage points, enjoy views of South Benson Marina & glimpses of the Long Island Sound & beach where you can walk for miles. Experience the best of Fairfield's beachside community, from summer concerts to 4th of July fireworks & neighborhood parades that make this area special. Conveniently located near open space trails, Sandcastle Playground & Roger Sherman Elementary School.

693 S Benson Rd, Fairfield

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