Refine Search
Sort by
70 Benedict Ave, Fairfield
$599,000
2 Beds ⋅ 2 Baths ⋅ 24209651 MLS
There's so much to love about this charming two-bedroom, two-bath Ranch in Fairfield's desirable Stratfield neighborhood! Perfect for those just starting out or looking to downsize. This inviting home offers comfortable living with the added finished lower level and full bath. Beautiful hardwood floors flow throughout the main level, including the recently refinished kitchen and sunroom floors. The spacious living room, featuring a cozy gas fireplace, opens seamlessly to a sun-filled dining room, creating a wonderful space for everyday living and entertaining. The neutral kitchen leads to a delightful sunroom overlooking the backyard-an ideal spot to relax and unwind. Both bedrooms offer generous storage and built-ins, adding to the home's charm and functionality. Additional highlights include gas heat, central air, new carpeting in the lower level, freshly painted throughout, and a one-car detached garage. Tucked away on a quiet street within walking distance to Lincoln Park, this lovely home offers a wonderful opportunity to enjoy all that Fairfield has to offer!

70 Benedict Ave, Fairfield

220 Melville Dr, Fairfield
$390,000
2 Beds ⋅ 1 Baths ⋅ 24209353 MLS
Welcome to 220 Melville Drive in Fairfield a charming brick half duplex with no association fees and your own private land. Hardwood floors run throughout the home, beginning on the main level where a comfortable living room flows into the eat in kitchen perfect for everyday living and entertaining. Upstairs, the bedrooms offer a quiet retreat with natural light and updated bathroom with skylight. Outside, enjoy the convenience of a private two car driveway and a fully fenced backyard, ideal for relaxing, gardening, or hosting gatherings. The property also features exceptional storage and utility with three sheds all equipped with electricity including a custom shed built specifically for the included snowblower and a larger shed that could be converted into finished space! So many possibilities. Upgrades include a new roof, new furnace, and a recently installed sewer liner, providing peace of mind for years to come. This home is walking distance to a park and ideally located close to shopping, dining, park square and with easy access to NYC, this home offers convenience, and value in a desirable Fairfield neighborhood.

220 Melville Dr, Fairfield

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

60 Bridle Trl, Fairfield

475 Eleven Oclock Rd, Fairfield
$1,299,000
5 Beds ⋅ 3 Baths ⋅ 24207544 MLS
**Please submit offers by 9/29 at 7pm** A rare opportunity to create your vision in coveted Greenfield Hill. Set on more than 2 acres in one of Fairfield's most desirable neighborhoods, this classic 5-bedroom Colonial offers exceptional space, a flexible floor plan, and tremendous potential. With nearly 4,000 square feet of living space, this is an ideal property for a buyer ready to update and personalize a home in an outstanding location. A versatile first-floor wing includes a bedroom, bath, and family room, creating an excellent option for a main-level primary suite, guest quarters, home office, or in-law/au pair suite. The welcoming foyer opens to a generous living room with fireplace and built-ins, a formal dining room, and a spacious kitchen with center island, bar area, and dining space. The spacious kitchen offers a large center island, bar area, and casual dining space, with access to a covered porch and deck overlooking the expansive property. Upstairs, the spacious primary bedroom features an en-suite bath and walk-in closet, while 3 additional bedrooms provide plenty of room for family and guests. The lower level adds nearly 1,000 sf of flexible bonus space, ideal for a rec room, home gym, office, playroom, or media space. A special opportunity to bring new life to a spacious home in a premier setting. Fairfield CT offers coastal charm, historic character, exceptional dining & shopping, vibrant arts and cultural amenities, 2 Universities and easy access to NYC.

475 Eleven Oclock Rd, Fairfield

97 Gorham Rd, Fairfield
$1,049,000
4 Beds ⋅ 2 Baths ⋅ 24205924 MLS
Step into this charming expanded Cape, ideally located on a quiet cul-de-sac in the heart of the coveted South Pine Creek beach area. Filled with warmth and character, this inviting four-bedroom, two-bath home is move-in ready while offering wonderful potential to expand in the future. Set on a flat .22-acre parcel, the property provides a fantastic opportunity in one of Fairfield's most desirable coastal neighborhoods. Inside, an open living and dining space creates an easy, comfortable flow, with sliders offering views and direct access to the backyard. The bright white kitchen features an eat-in area and convenient mudroom space. A first-floor bedroom and full bath provide flexibility for guests, a home office, or main-level living. Upstairs, the spacious primary bedroom offers generous closet space and is joined by two additional bedrooms and a beautifully renovated full bath. The finished lower level provides additional flexible living space, ideal for a playroom, home office, gym, media room, or bonus room. Enjoy the best of the Fairfield beach lifestyle with the beach, town, restaurants, shops, and train all within easy reach. A charming, happy home in a truly fantastic location!

97 Gorham Rd, Fairfield

181 Miro St, Fairfield
$765,000
3 Beds ⋅ 3 Baths ⋅ 24208476 MLS
***HIGHEST & BEST DUE WEDNESDAY 9/20 AT NOON *** Fully updated and move-in ready, this home sits on a quiet, low-traffic street just minutes from both I-95 and the Merritt Parkway, an ideal setup for commuters who still want a peaceful neighborhood setting. You're right down the street from local schools and just minutes from area shopping. Freshly painted throughout, the home features refinished hardwood floors across the main level, a bright living area, and an eat-in kitchen with a newer sliding door leading out to the deck. Three bedrooms sit on the upper level, including a primary suite with its own private full bath. Downstairs, the finished lower level offers brand-new flooring and a versatile extra room that works perfectly as a home office, home gym, extra storage space, or even a 4th bedroom. Major mechanical updates include a new air handler, condenser, and a backup generator. The absolute highlight of the property is the incredible backyard. Completely flat, fully fenced, and wide open, it offers an exceptionally rare amount of usable space for play, pets, and outdoor entertaining right off the deck.

181 Miro St, Fairfield

738 Rowland Rd, Fairfield
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 24200231 MLS
Barely a block from Fairfield Beach this stylish beach house offers bright, designer-chic living with year-round marsh views. The open main level features hardwood floors, a light-filled living area, and a Nantucket-style kitchen with a quartz island and stainless steel appliances. The adjacent dining room leads through French doors to an expanded Trex deck overlooking the marsh. Upstairs, the primary suite boasts a walk-in closet, serene views, and a renovated ensuite bath, alongside two additional bedrooms, a updated full bath, and dedicated laundry. A lower-level mudroom connects to the attached two-car garage and a carved out office space. Highlights include a firepit, outdoor shower, and key upgrades like a new roof, windows, and deck-all just minutes from downtown Fairfield's dining, shops, and train. Gated Beach access awaits you just steps from the house.

738 Rowland Rd, Fairfield

20 Glen Arden Dr S, Fairfield
$899,000
3 Beds ⋅ 3 Baths ⋅ 24208763 MLS
Slow mornings, lively gatherings and room to unwind-welcome to life at 20 Glen Arden Drive South. Set on nearly half an acre in Fairfield's University neighborhood, this 3-bedroom, 3-bath Colonial offers inviting spaces for every pace of the day. Gather around the kitchen island for coffee and conversation, host dinner in the dining room, then mix a favorite drink at the wet bar and settle in beside the fire. Two fireplaces bring warmth to evenings at home, while hardwood floors lend classic character throughout. Outside, the professionally landscaped grounds set the stage for everything from backyard games to leisurely afternoons. Serve dinner on the patio, linger with friends by the cabana or slip away to the balcony for a quiet moment. There's space here to entertain a crowd and enjoy a little solitude. Main-level laundry and a two-car garage keep daily routines easy, while nearby shopping, dining, beaches and parks put the best of Fairfield within easy reach. Thoughtful improvements include a new roof, exterior painting and carpentry completed in 2025, plus kitchen updates featuring an induction cooktop, center island with microwave, counters and pantry. Attic spray foam insulation, a newer water heater and refinished hardwoods further enhance this inviting home.

20 Glen Arden Dr S, Fairfield

50 Southport Pl Unit 50, Fairfield
$1,299,000
3 Beds ⋅ 4 Baths ⋅ 24208534 MLS ⋅ Pequot Landing BLDG.
Step into a lifestyle of effortless elegance at 50 Southport Pl, a stunning 3-story end-unit townhouse nestled w/i the coveted Pequot Landing enclave. Blt in 2004, beautifully refreshed 2021/23, this residence perfectly captures the timeless coastal charm of Southport while offering sophisticated, modern amenities today's discerning buyer craves. From the moment you enter, the quality of the recent upgrades is evident. The interior shines w/freshly painted walls, stylish light fixtures, custom wndw trtmnts & gleaming refinished hardwood floors that lead you through an open, airy layout. The refreshed EIK features a center island, granite countertops, premium SS appliances & w/in pantry. Entertainment flows naturally between the DR & LRs, anchored by a sophisticated double-sided gas fireplace that adds warmth & ambiance to both spaces. For those who work from home, the main-level office/library provides a quiet, refined retreat. Upstairs, the PBR suite serves as a true sanctuary, boasting dramatic vaulted ceilings, a generous walk-in closet, & a new in 2023, spa-like ensuite bath. 2 add'l well-appointed BRs ensure plenty of space for guests or creative uses. The versatility continues on the fin walkout LL, w/its own FBA & French doors leading to a private patio, this space is ready to become a high-end fitness studio, a second offic, or an add'l BR suite. The home also features direct garage access & a thoughtful design that is elevator-ready for future proofing lifestyle.

50 Southport Pl Unit 50, Fairfield

42 Puritan Rd, Fairfield
$4,100,000
5 Beds ⋅ 5 Baths ⋅ 24206950 MLS
Welcome to this next-level Fairfield Beach residence where bespoke luxury meets a fun coastal lifestyle. Just 2 blocks from the sand, this sun-drenched 5 bedroom, 4.5 bath beach haven is masterfully designed space. Every room tells a story through oversized windows, gorgeous textiles, designer wall coverings and unique lighting. The main living spaces are open, airy and filled with coastal light, featuring multiple entertaining areas for unforgettable gatherings and relaxation. From the culinary lover's dream Kitchen with Wolf, Bosch, SubZero appliances and walk-in pantry, to the Living Room anchored by a magnificent fireplace to a one-of-a-kind Bar with brass and smoked mirror accents, to the refined Study with incredible space and cabinetry. The Upper Two Levels delight with all 5 bedrooms being generously-sized and en-suite, offering ultimate privacy and luxury. The Primary Suite is so inviting with a private deck, luxurious bath with steam shower, radiant heat flooring and 2 walk-in closets. The Third Floor is a special and versatile private retreat featuring the 5th Bedroom, a lounge/exercise area, deck and dedicated workspace with built-in desks and wet bar. The interior flows effortlessly to a private resort-style backyard with mature evergreens and walls of hydrangea, Pool, Spa and Shower. Dedicated elevator space on 4 floors, EV charger, Sonos, Generator all ensure easy living AND Sherman Elementary, Beach, Restaurants are a leisurely walk or bike ride away.

42 Puritan Rd, Fairfield

360 Pansy Rd, Fairfield
$675,000
3 Beds ⋅ 3 Baths ⋅ 24187893 MLS
Set on nearly half an acre of level, dry land, 360 Pansy Road offers a rare combination of timeless charm and future potential. The existing ranch features one-level living with a sun-filled living room, kitchen, primary suite with full bath, two additional bedrooms, and a second full bath. Throughout the home, architectural details like ornate plaster medallions, intricate crown molding, and stunning black-and-white tilework creates a sophisticated and highly distinctive design aesthetic. The lower level adds exceptional flexibility with a beautifully done office, walk-in closet, spacious laundry room, den with wet bar, full bathroom, and separate entrance. A walk-up attic provides abundant storage. Mature privacy trees perfectly frame this expansive .40 acre property, partially fenced, providing excellent potential for a pool, expansion, or exploration of a new residence up to approx. 7,000 square feet, two and a half stories tall. 360 Pansy sits in a prime Fairfield location; a short walk around the corner from shops and restaurants. Minutes from the Merritt Pkwy, 95, train station(s). Don't miss this unique property with endless possibilities. Schools for 360 Pansy Rd: Osborne Hill, Fairfield Woods, Fairfield Warde. Private well; public water connected to nearby homes on Pansy Road.

360 Pansy Rd, Fairfield

96 Benedict Ave, Fairfield
$979,000
4 Beds ⋅ 3 Baths ⋅ 24207603 MLS
Charming 4-5 bedroom English colonial circa 1932, sited on an over-sized, professionally landscaped property with stone walls, patio and circular driveway. Period details abound with arched doorways, bay windows, French doors, hardwood floors and wide staircase. Chef's eat-in-kitchen with stainless appliances, granite topped island and banquette seating in bay window is the heart of the home. The front-to-back living room features a fireplace and storage cabinets with French doors, providing a special place to display your finest collectibles. Located off the formal living room is a small den which is also perfect for an office or library and provides access to the patio, overlooking the verdant rear grounds. There is also a family room on the main level, located near a full bath, which can be used as a fifth bedroom. Upstairs you will find an enlarged primary suite featuring a walk-in closet, dressing room with French doors, double mirrored closets, marble bath with jetted tub, large shower with frameless glass enclosure and abundant storage. 3 more bedrooms and bath complete this level. A LL features a play room/laundry room and access to 2 car garage. Many updates include refinished hardwood floors, paint, new central air (9/26),tankless hot water heater ('24), furnace ('24), roof ('04), electrical, cedar closet in attic and security system. Desirable Stratfield Village location near Jackman park, shops, universities, houses of worship, farmer's markets and transportation.

96 Benedict Ave, Fairfield

102 Glen Ridge Rd, Fairfield
$650,000
3 Beds ⋅ 1 Baths ⋅ 24207656 MLS
Opportunity awaits at 102 Glen Ridge Road! Set on .46 acre on a corner property in an established Fairfield neighborhood, this home offers possibilities for a variety of buyers. Move in and make it your own, renovate and reimagine the existing home, or explore the potential for new construction. Features include stainless steel appliances, an outdoor patio with porcelain tile, and a finished lower level offering three additional rooms currently used as a family room, office and craft room, plus three additional closets for storage. Enjoy a truly walkable location! Walk to nearby elementary and middle schools, Fairfield Woods Branch Library, Highwood Park with ball field, basketball court and playground, and Lake Mohegan with hiking trails, seasonal beach, splash pad, lifeguards and snack bar. Commuters will appreciate easy access to the Merritt Parkway, I-95 and Fairfield's three Metro-North train stations. Fairfield also offers five town beaches, great shopping and restaurants, parks and recreation. Whether you're looking to downsize, purchase a home you can update over time, renovate, invest or build new, 102 Glen Ridge Road offers an opportunity to make this property your own.

102 Glen Ridge Rd, Fairfield

58 Meadow Ct, Fairfield
$1,295,000
3 Beds ⋅ 3 Baths ⋅ 24204742 MLS ⋅ Meadow Court Condominium BLDG.
A lifestyle you can truly enjoy - the perfect blend of luxury, privacy, convenience and low-maintenance living. Set on a quiet 10-home cul-de-sac near Fairfield's town and beach areas, this renovated home is filled with natural light and offers an ideal open floor plan, 9' ceilings, two office spaces and a private, fenced rear yard with patio. From the moment you enter, the thoughtful design is apparent. French doors open to a private office off the front entry, while the home unfolds into an expansive open living space where the living room, dining room and kitchen flow seamlessly together. The living room features a gas fireplace flanked by windows and sliders to the backyard, while a wall of windows along the rear of the home fills the space with natural light and creates an easy connection to the outdoors. The kitchen features a natural wood island, Quartz countertops, Viking Professional stainless-steel appliance suite, Bosch dishwasher and adjoining bistro area. A 2-car garage provides direct access to a sizable pantry, mudroom and powder room. Upstairs, a primary suite features vaulted ceilings, nearly floor-to-ceiling windows, a WIC and an expansive full bath with a wall of White Dove cabinetry, Jacuzzi and tiled shower. Two additional BRs, a laundry room, full bath and open-air office complete this level. A walk-up attic offers storage and potential living space. Turn-key, light filled and ideally located close to train to NYC, beaches, parks, dining, shopping!

58 Meadow Ct, Fairfield

78 Greenbriar Rd, Fairfield
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 24207389 MLS
Set in the desirable University area, this expanded ranch offers inviting spaces, beautiful architectural details and a backyard that feels like a private oasis. Custom craftsman touches incl crown molding and custom paneling create a warm sense of character throughout. The chef's kitchen, with generous island,is perfect for morning coffee, and casual meals.The dining room is ideally situated for inspired entertaining. The heart of the home is the stunning family room, where a soaring cathedral ceiling and fireplace create a comfortable place to gather. French doors open to an extraordinary outdoor retreat designed for long summer days and unforgettable evenings. Swim in the heated gunite pool, relax in the spa, enjoy dinner on the patio, and gather for drinks at the tiki bar. An outdoor shower and lush grounds complete this vacation-at-home setting.Upstairs, the thoughtfully added bonus space offers room to adapt as life changes; whether used as a home office,playroom, 4th bedroom, or creative studio. A finished space in the bsmt plus plenty of storage add to the home's functionality. The ease of ranch-style living with flexible additional space and exceptional indoor-outdoor entertaining, this is a home meant to be enjoyed in every season. All situated on a culdesac road just minutes from Fairfield Center dining, shopping, MetroNorth and 5 LI Sound beaches. Walk to Osborn Hill School.Easy NYC commute by highway, Merritt Parkway or train.

78 Greenbriar Rd, Fairfield

148 Ridgeley Ave, Fairfield
$699,000
3 Beds ⋅ 2 Baths ⋅ 24207543 MLS
NEW NEW NEW!! Great opportunity to purchase this newly totally reconstructed Cape Cod at an affordable price! The main level features an open kitchen/family area, dining room which leads to the relaxing covered front porch and the primary bedroom with full bathroom. The upper level has two additional bedrooms, office area and a full bathroom. The home offers hardwood floors throughout, custom kitchen with stainless appliances, quartz countertops and island, carrier heating and central air, Rheem tankless water heater, two car garage. This home is conveniently located near all your shopping needs, schools, I-95, train stations, town center and beaches. Taxes will be assessed after the CO. Owner has a Connecticut Real Estate License.

148 Ridgeley Ave, Fairfield

210 Berwick Ave, Fairfield
$449,000
3 Beds ⋅ 2 Baths ⋅ 24207424 MLS
Discover the charm of easy, carefree living in this move-in ready bungalow tucked away on a convenient cul-de-sac. Surrounded by fruit trees and thoughtfully designed outdoor spaces, this three-bedroom, two-bath home offers a tranquil retreat while remaining close to shopping, restaurants, and everything Fairfield has to offer. The primary bedroom of this home is located on the first floor while the second and third bedrooms are tucked away on the second floor. Natural light floods into the dining and living rooms and the living room features a wood burning fireplace. Enjoy al fresco dining on the expansive deck, unwind in the garden seating areas, or begin each day with a quiet walk among the trees and the beauty of nature right outside your door.

210 Berwick Ave, Fairfield

6 Stoneleigh Sq, Fairfield
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 24206842 MLS
Pristine Cape on a beautiful Stratfield street featuring a first-floor Primary Bedroom Suite, gleaming hardwood floors, and thoughtful touches throughout, blending charm, space and modern updates. The inviting Foyer opens to a stunning Dining Room with custom built-ins and an oversized Living Room overlooking the private park-like backyard. A spacious Family Room with built-ins and a fireplace flows seamlessly to the refinished deck and screened in gazebo - perfect for indoor/outdoor living. The updated eat-in Kitchen offers stainless steel appliances, pantry storage, and an adjacent updated laundry room. The second floor includes a large main bath, added hall storage, and three bedrooms plus an office, currently used as a bedroom. The tax records convey 3 bedrooms, though sellers currently utilizing bonus room as 4th bedroom. Recent improvements include custom lighting, new hardware, updated laundry room space, and fresh interior paint in every room (including its 24 closets!). Truly an impeccably maintained home in a sought-after neighborhood of Fairfield.

6 Stoneleigh Sq, Fairfield

366 Brookside Dr, Fairfield
$715,000
3 Beds ⋅ 2 Baths ⋅ 24207176 MLS
Welcome to this beautifully updated home in the desirable Lake Hills Association, where comfortable living comes with lake and beach access. Larger than the typical Cape, this 3 bed, 2 bath home offers a bright, open floor plan with hardwood floors, generous living spaces, and an easy flow for everyday life and entertaining. At the heart of the home is the updated kitchen, featuring white cabinetry, quartz countertops, stainless steel appliances, a tile backsplash, and an oversized island with seating. The kitchen opens to the living and dining areas, creating a spacious gathering space filled with natural light and highlighted by a charming fireplace. Just off the main living area, the screened three-season porch with removable windows offers a peaceful place to relax and enjoy the surrounding greenery. Recent updates include crown molding, hardwood flooring, walk-in showers, and a refreshed lower level. The partially finished basement offers flexible space for a family room, office, gym, or recreation area, while the unfinished portion and oversized attic provide excellent storage. Major improvements include a new furnace, new oil tank, and new blown-in insulation. With its welcoming curb appeal, updated interior, flexible living space, and lake and beach access, this home is ready to enjoy year round.

366 Brookside Dr, Fairfield

185 Nepas Rd, Fairfield
$989,000
4 Beds ⋅ 3 Baths ⋅ 24206070 MLS
Nestled in Fairfield's desirable Lake Mohegan area & convenient to everyday amenities,this warm & inviting 4-BR, 2.5-BA Colonial offers 2,028 sq.ft. of comfortable living space.Set back w/mature trees & well-maintained grounds,this property provides a peaceful connection to nature.Freshly painted interiors & refinished HW floors create a welcoming atmosphere throughout.The bright eat-in kitchen features abundant cabinetry, a large pantry, updated fixtures & a large window showcasing seasonal views.Enjoy gatherings in the dining room,relax in the front-to-back living room w/ a wood-burning fireplace, or unwind in the spacious family room featuring a gas fireplace & built-ins.French doors open to one of the home's showpiece spaces:a sun-filled sunroom (add.324 sft) w/ skylights,walls of windows, tongue-and-groove detailing,new flooring & sliders that seamlessly blend indoor/outdoor living.Upstairs are 4 generously sized BRs, including a primary suite w/ BA & 2 large closets.A full basement(1128 sft), pull-down attic & additional attic space above the garage provide great storage & future possibilities.The large slate patio overlooks the private backyard, offering the perfect setting for morning coffee,dining or entertaining. Add features include Marvin windows,central air,whole-house generator & 2-yr-old HW heater. Convenient to shopping, dining, parks, beaches, lakes, train, Merritt Pkwy & I-95. This home is ready for its next owners to make it their own & create new memories.

185 Nepas Rd, Fairfield

305 S Gate Ln, Fairfield
$2,000,000
4 Beds ⋅ 5 Baths ⋅ 24203819 MLS
Set on one of Southport's most coveted streets, this gracious 4 bedroom, 4 bath Colonial offers over 5,200 square feet of finished living space on more than a half acre. Thoughtfully designed for both everyday living and entertaining, the main level features a formal living room and dining room, custom millwork throughout, a spacious eat in kitchen with a dedicated dining area, an inviting family room with fireplace and access to the deck and private backyard, plus a dedicated home office. The upper level is highlighted by an expansive primary suite with two generous walk in closets, a beautifully appointed bath and private sitting room offering flexibility as a fifth bedroom, nursery, office or fitness space. Three additional bedrooms include one with an en suite bath, while the other two share a Jack and Jill bath. Upper level laundry completes this floor. The finished lower level adds over 1,600 square feet for a media room, recreation room, gym or guest space. Generous closet space, mature landscaping and wonderful indoor and outdoor living create a home that feels both refined and comfortable, with room to gather, entertain and grow. From quiet evenings by the fireplace to summer dinners on the deck, the home offers spaces that are meant to be enjoyed. Just minutes from Southport Village & Beach, Pequot Library, golf, shopping, dining and Metro North, this is an exceptional opportunity to enjoy the space, privacy, convenience and lifestyle that make Southport so special.

305 S Gate Ln, Fairfield

136 Chatham Rd, Fairfield
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 24206592 MLS
There's something timeless about coming home to a classic Colonial on a quiet street, especially w/ nearly half an acre of level, fenced-in yard waiting out back. Set on one of Stratfield's most desirable streets, this home offers space to gather, room to grow & a setting tucked away yet close to everything Fairfield has to offer. Wrapped in cedar shake shingles, the home welcomes you w/ a new roof, energy-efficient windows, bluestone steps & two-bay garage. Inside, abundant natural light pours across red oak floors. The living room centers around a wood-burning fireplace & opens through French doors to a window-lined sunroom/office w/ a vaulted ceiling, backyard views & patio access. The eat-in kitchen offers granite counters, stainless appliances & ample cabinetry, flowing naturally into the formal dining room. The family room w/ built-in shelving creates an inviting space for everyday living & entertaining, w/ a slider directly to the patio & yard. A mudroom & powder room complete the main level. Upstairs are 3 sizeable bedrooms w/ hardwood floors & California walk-in closets, including a primary suite w/ private bath, plus a second full hallway bath. The walk-up attic offers potential for additional bedrooms, guest suite, gym or media room, while the unfinished basement adds more possibilities. Outside, the level .45-acre fenced yard, mature landscaping & generous patio create a private retreat w/ plenty of space to play, dine outside, entertain or explore a future pool.

136 Chatham Rd, Fairfield

446 Wormwood Rd, Fairfield
$2,299,000
4 Beds ⋅ 4 Baths ⋅ 24206534 MLS
Exceptional New Construction in the University Area. Nestled on a quiet, low-traffic street in the heart of the desirable university neighborhood, this stunning new construction home perfectly blends luxury craftsmanship, modern functionality, and unmatched convenience. Currently under construction with a planned completion for May, this property offers a rare window of opportunity for buyers to step in, select custom finishes, and truly tailor the design to fit their personal vision. Built by one of the region's most well-known and respected local builders-celebrated for high-quality architectural detail and a proven portfolio of exceptional homes- this residence is thoughtfully designed inside and out. Spacious living: designed with an open, modern flow featuring 4 generous bedrooms and 3.5 baths, ideal for both everyday living and formal entertaining. Customization Potential: Early buyers can consult directly with the builder to select key interior options, fixtures, and personalized details before construction wraps. Refined Craftsmanship: Expect premium trim work, high-end surfaces, and beautiful architectural touches throughout the entire footprint. Unbeatable Location and Accessibility. Tranquil Setting: Enjoy the peace of a secluded, quiet neighborhood within a vibrant university setting. Commuters Dream: Central access puts you minutes away from local trains, downtown shopping and dining, and major highway corridors for easy travel. Opportunity awaits!

446 Wormwood Rd, Fairfield

550 Wellington Dr, Fairfield
$1,925,000
4 Beds ⋅ 4 Baths ⋅ 24206227 MLS
Tucked at the end of a quiet Greenfield Hill cul-de-sac, 550 Wellington Drive feels like a true retreat-private, peaceful and designed for the way you actually want to live. Set on 2.47 secluded acres, this 4-bed, 4,776sqft home offers an exceptional amount of space to gather, entertain and spread out, with a floor plan that gives everyone a place of their own. The 1st floor is especially expansive, with a gracious living room, dramatic vaulted family room, oversized playroom, sunroom and sophisticated wood-paneled office-spaces that easily adapt for entertaining, working from home, play or simply finding a quiet corner to unwind. The kitchen sits at the heart of the home, creating an easy connection between everyday living and the many gathering spaces. Upstairs, four bedrooms provide a comfortable separation from the main living areas, complemented by recently updated bathrooms. Outside is where 550 Wellington truly becomes an escape. Surrounded by mature landscaping and complete privacy, the backyard resembles a private resort with pool, expansive deck, screened-in porch and abundant space for outdoor dining, entertaining and long summer days at home. A three-car garage completes the offering. Spacious yet inviting, private yet close to everything Greenfield Hill has to offer, 550 Wellington Drive is a homemade for gathering, entertaining and getting away-without ever having to leave home.

550 Wellington Dr, Fairfield

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

3901 Redding Rd, Fairfield

79 Thorpe St Unit 79, Fairfield
$1,065,750
3 Beds ⋅ 4 Baths ⋅ 24205727 MLS ⋅ Thorpe Street Crossing BLDG.
The downtown opportunity you've been waiting for is here! This stunning townhouse-style condo offers three beautifully finished levels with thoughtful design and sophisticated details throughout. Custom millwork, built-in seating, and elegant paneling create a polished yet welcoming atmosphere. The sun-filled, open-concept main level features oversized windows, a spacious dining area, an inviting living room with a gas fireplace, and a beautifully crafted kitchen with a waterfall center island and pantry. Sliders open to a private deck, patio, and fully fenced backyard, perfect for entertaining and indoor-outdoor living. The luxurious primary suite boasts 9-foot ceilings, a board-and-batten accent wall, walk-in closet, and spa-inspired bath with heated floors, soaking tub, dual vanities, and oversized walk-in shower. The versatile third level provides approximately 625 square feet of additional living space with a full bath, closets, and ample storage. Ideal for a media room, home office, guest suite, game room, or potential fourth bedroom. Additional highlights include 9-foot ceilings on the first and second floors, an oversized one-car garage, and three additional parking spaces. Walk to the train, beaches, restaurants, and shopping!

79 Thorpe St Unit 79, Fairfield

394 Wakeman Rd, Fairfield
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 24205035 MLS
Step into a storybook setting of Fairfield's "CT Cotswolds." This 1931 custom-built Cape Colonial is a masterclass in timeless elegance, where old-world character seamlessly blends w/high-end modern comforts. From the moment you cross the flagstone-covered front porch & enter the foyer, the home's heritage shines through the graceful curved staircase & rich wide-board flooring. The main level is designed for both sophisticated entertaining & quiet relaxation. The impressive LR anchors the home w/its wood-burning FP & beamed ceilings, while the formal DR delights w/artisan details like classic corner cabinetry. For those seeking a quiet retreat, the sun-drenched den serves as the perfect library or bright home office. At the heart of the home, the gourmet chef's kitchen is a showstopper. Vaulted, beamed ceiling & expansive windows frame views of the lush grounds, while Viking appliances, granite countertops, & clever storage solutions cater to the most ambitious culinary pursuits. The 1st flr Primary suite is a sprawling sanctuary featuring b/i closets, bath w/dbl shower, & private sitting room for peaceful mornings. Upstairs, 3 add'l bright BRs & FBA. The fin LL is the ultimate destination for game days, complete w/wet bar, b/ins, 1/2 bath, office space. Outside, the property transforms into a private oasis. Exquisite perennial gardens wrap the home in color, providing a stunning backdrop for alfresco dining. It's more than just a house; it's a retreat that feels like HOME.

394 Wakeman Rd, Fairfield

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

1074 Sturges Hwy, Fairfield

125 Coleman Rd, Fairfield
$1,894,500
4 Beds ⋅ 4 Baths ⋅ 24205547 MLS
Sophistication meets the warmth and ease of Fairfield living in this exceptional new-construction residence. Offering approximately 4,500 square feet of beautifully finished living space, this custom 4-bedroom, 3.5-bath home pairs clean architectural lines and warm natural materials with a layout designed for both everyday comfort and effortless entertaining. At the heart of the home, the designer kitchen features custom cabinetry, a premium Thermador appliance package, an oversized island, a dedicated bar area, and a fully equipped walk-in pantry with a prep sink. Select-grade white oak flooring and ceilings of nine feet or higher create a bright, airy flow throughout the home. The spacious living room is anchored by a gas fireplace, while a dramatic 10-foot bifold door creates a seamless connection to the covered porch and private, fully fenced, level backyard-with room for a pool. Upstairs, vaulted ceilings bring striking architectural character to the expansive primary suite and Jack-and-Jill bedrooms. Each bedroom offers direct access to a full bath and its own custom walk-in closet. The finished lower level adds exceptional flexibility for recreation, fitness, a home office, or guest accommodations. Set on a quiet neighborhood street just moments from Lake Mohegan, neighborhood parks, shopping, and the Merritt Parkway, this thoughtfully designed home delivers elevated style, exceptional craftsmanship, and the very best of modern living.

125 Coleman Rd, Fairfield

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!