Fairfield Homes with Fairfield Woods Middle school

Welcome to Fairfield, Connecticut—a charming coastal town that perfectly blends suburban tranquility with vibrant community life. Nestled in Fairfield County, this picturesque town boasts stunning beaches, lush parks, and a rich tapestry of history. With a population that cherishes its close-knit community, Fairfield offers a welcoming atmosphere for families, young professionals, and retirees alike.

One of the standout features of Fairfield is its commitment to education, highlighted by the esteemed Fairfield Woods Middle School. Homes in proximity to this well-regarded institution are highly sought after, making them ideal for families prioritizing quality education. The school’s dedicated staff and diverse curriculum foster a nurturing environment where students can thrive academically and socially.

Living in Fairfield means enjoying a plethora of recreational activities. The town features beautiful beaches along the Long Island Sound, perfect for sunbathing, swimming, and picnicking. For outdoor enthusiasts, the numerous parks and nature trails provide ample opportunities for hiking, biking, and enjoying the serene natural beauty of the area. Additionally, the vibrant downtown area is home to a variety of shops, restaurants, and cultural attractions, ensuring there’s always something to explore.

Whether you’re drawn to the allure of the coastline, the top-notch schools, or the strong sense of community, Fairfield offers a unique lifestyle that’s hard to resist. Discover your dream home near Fairfield Woods Middle School and become part of this enchanting town, where every day feels like a getaway. Embrace the perfect blend of comfort, convenience, and community in beautiful Fairfield, CT!

Newest Fairfield Homes with Fairfield Woods Middle school

$1,049,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 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 that feels tucked away yet close to everything. Wrapped in cedar shake shingles, the home welcomes you w/ a newer roof, energy-efficient windows, bluestone steps & a two-bay garage. Inside, natural light pours across red oak floors. The living room centers around a wood-burning fireplace & flows into a window-lined sunroom/office w/ a vaulted ceiling, backyard views & patio access. The eat-in kitchen features granite counters, stainless appliances & ample cabinetry, while the formal dining room & centrally positioned family room with built-in shelving create an easy flow for everyday living & entertaining. A laundry/mudroom & powder room complete the main level. Upstairs are 3 sizeable bedrooms w/ hardwood floors & outfitted California walk-in closets, including a primary suite w/ a private bath, plus a second full bath for the other bedrooms. The walk-up attic offers exciting potential for additional bedrooms, a guest suite, home gym or media room, while the unfinished basement provides even more possibilities. Outside, the level .45-acre fenced yard, mature landscaping & generous patio create a private retreat w/ plenty of room to play, entertain, dine outside or explore a future pool.

136 Chatham Rd, Fairfield

$629,000

4 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24196770 MLS

Traditional on the outside and surprisingly spacious on the inside, this University cape is freshly updated and is ready for its next owners. A sun-filled living room welcomes guests a it features a bay window and gleaming hardwood floors which extend throughout bedrooms on the main and upper levels. A total of four bedrooms ( two on the main level and two upper) feature potential dining and home office use. Refreshed kitchen with stainless steel appliances, subway backsplash, two full bathrooms are in move-in ready condition. A breezeway, mud room links the attached garage for all weather coverage. A full walk-out basement leads to a private patio and peaceful back yard. The generous sized lower level also includes a washer/dryer, extra refrigerator, workshop and space for a possible home gym and additional storage. Ideally located minutes from town, medical facilities, two train stations, schools, shopping, Merritt and I-95.

438 High St, Fairfield

$899,900

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205504 MLS

Welcome to this beautifully cared-for, move-in ready 5-bedroom, 2.5-bathroom home nestled within Fairfield's distinctive Dover Park neighborhood. The main level offers a comfortable and inviting layout with a spacious living room, dining room, kitchen, and welcoming family room. The family room features a beautiful brick wall and wood-burning fireplace, creating a warm setting for relaxing, entertaining, and spending time with family and friends. Two additional bedrooms are conveniently located on the main level near a full bathroom. Upstairs you will find three spacious bedrooms, including a generously sized primary bedroom with a walk-in closet, plus two additional bedrooms.Storage will never be an issue, thanks to a pull-down attic and a full, unfinished basement. These spaces provide ample room for storage, hobbies, a workshop, or future possibilities.Outside, the property truly shines.The spacious, flat backyard is surrounded by mature trees and beautifully established landscaping, creating a private and tranquil outdoor retreat.A distinctive natural rock outcropping adds character and a unique sense of place, while the generous deck provides an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings.Recent improvements add to the home's appeal and peace of mind: a new roof (2026), new driveway (2025), and radon remediation (2025). Solar panels on the rear of the home provide excellent energy efficiency. Make your appointment today!

37 Stevenson Rd, Fairfield

$869,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205513 MLS

One of the best side street locations in Fairfield's University neighborhood! This updated single family home is so close to all town amenities: the train, center of town, highways and Black Rock Turnpike! Beyond location, this home has newly refinished hardwood flooring and fresh paint throughout offering bright living spaces, lots of storage and a gorgeous fully-fenced in backyard! Just off Mill Plain Rd, this home is on a dead-end side street with open space across the street, a perfect combo offering privacy within a neighborhood setting! Featuring 3 bedrooms, 1.5 bathrooms and many newer features for high efficiency living like new central air in 2025, updated furnace, 200 amp electric, windows, and an updated kitchen with pantry! The main floor has an open floor plan with a large living room, dining room, kitchen and family room. All 3 bedrooms are upstairs along with a full bathroom and large linen closet. The spacious bonus room is a walk-out featuring a half bathroom with laundry and full-size windows for lots of light. Other features include an attached 1 car garage and large deck and pea-stone patio overlooking the flat yard. This home is stunning with a great property, close to everything. What a charming place to call home!

65 Cynthia Dr, Fairfield

$1,399,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$1,894,500

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24205547 MLS

Westport-inspired 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

$765,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24205398 MLS

The neighborhood you've been waiting for and an opportunity that is increasingly hard to find in Fairfield. Set on an oversized lot backing to Fairchild Wheeler Golf Course, this mid-century ranch offers a remarkable blend of location, privacy, character, and possibility. Mature trees and plantings surround the property, creating a park-like setting that feels unexpectedly secluded while still being close to Fairfield beaches, live music, dining and shopping. Inside, more than 1,700 square feet of inviting living space is waiting to welcome you. Beautiful hardwood floors extend through most of the home and built-ins in the living room add to its charm. The kitchen offers ample space to dine while enjoying peaceful backyard views. Just off the foyer and kitchen is the family room which may become your favorite place in the house. A wood-burning fireplace with stone surround anchors the space, while more oversized windows frame the beautiful backyard. The home offers three bedrooms and two full baths. The primary br includes its own newly refreshed bath. The second full bath is a wonderful nod to the home's original character, with beautifully preserved pink tile paired with updated wallpaper and lighting for a look that feels playful and completely at home here. The unfinished basement offers untapped potential to those who may want more space. For buyers who have been waiting for the right combination of location, land, livability and value 111 Casmir is a must see.

111 Casmir Dr, Fairfield

$695,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24203912 MLS ⋅ Woodfield Village BLDG.

Fairfield's sought-after Woodfield Village community, 170 Glengarry Road is an exceptional corner end-unit offering space, natural light, and effortless living. At 1,858 square feet-the largest unit in the complex-this beautifully maintained home features two bedrooms, two full and one half baths, a versatile den which is unique to the units, and the rare convenience of a two-car attached garage. Its coveted corner location overlooks the beautifully maintained grounds, while oversized windows bathe the interior in natural light. Freshly painted and enhanced by hardwood floors, the impressive living room features a soaring vaulted ceiling and wood-burning fireplace, creating a warm and inviting centerpiece for everyday living and entertaining. The generously sized dining room flows seamlessly into the kitchen, appointed with stainless steel appliances and abundant storage. Primary bedroom suite offers two large walk-in closets. The expansive unfinished lower level offers wonderful potential for a family room, home office, gym, or media space, while still providing ample storage and workshop possibilities. Woodfield Village residents enjoy an array of amenities, including a pool, pool house, and tennis/pickleball court. Ideally located near shopping, dining, Fairchild Wheeler Golf Course, Metro-North, Fairfield's beaches, Lake Mohegan, and the Merritt Parkway, this distinctive home delivers an enviable combination of space, privacy, convenience, and effortless Fairfield living

170 Glengarry Rd Unit 170, Fairfield

$1,499,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204891 MLS

Welcome to 50 University Dr, where character, craftsmanship, and comfort come together effortlessly. Tucked into one of the most coveted enclaves near Fairfield University, this colonial-style home was custom built from the foundation up in 2021 with refined finishes and carefully selected upgrades. Outside: cedar shake siding, Azek pergola and trim, Trex decking, oversized Nicolock patio, horseshoe driveway, Marvin windows and doors, and a full-house generator. The landscaped grounds include a "dog proof" fully fenced backyard. Inside, 8" white oak floors run throughout, with high ceilings, modern trim, neutral paint, and brass and aged brass hardware. The kitchen connects to the garage and sits between the family and dining rooms for effortless entertaining. A walk-in pantry doubles as "kitchen overflow" to hide clutter. It's finished with custom cabinetry, Bosch SS appliances, quartz counters, and a large island with hidden storage and seating for 3. The 1st floor also offers a formal living room with custom marble-surround gas fireplace, a full bath, and a bedroom that works as an office or guest room. Upstairs, the primary suite features a tray ceiling, large walk-in closet, and spa-like bath with heated tile floor, double vanity, and glass-door tiled shower with heated seat. 2 more bdrms have vaulted ceilings, ceiling fans, and closet systems, served by a 3rd full bath. Timeless character and lasting quality, ready from day one.

50 University Dr, Fairfield

$895,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204948 MLS

Just like New Construction. Whole house from top to bottom have been fully renovated with new luxury Kitchens & Bathrooms, New Sheet Rocks, new plumbing, new Electric, Gas Heating and New Central Air condition units. Sparkling new hardwood floors throughout the house. Spacious Living rooms with Fireplaces in both units. Kitchens with central Island are fully equipped with custom built cabinets, Quartz countertops and top of the line appliances. Semi-finished basement for extra storage space or Gym/Playroom, Driveways on both sides of the building just paved, one car garage and nice back yard. Close to I 95, Bus line, Shopping and restaurants. Agent Partner.

27 Longview Ave, Fairfield

$750,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204373 MLS

Tucked into Fairfield's sought-after University neighborhood, this inviting 3-bedroom, 2-bath home offers the perfect blend of character, comfort, and convenience. A circular driveway, classic cedar exterior, and beautiful mahogany front door create a memorable first impression. Inside, hardwood floors and oversized windows fill the main level with natural light. The eat-in kitchen features granite countertops, stainless steel appliances, and an adjoining mudroom for everyday functionality. A first-floor bedroom offers wonderful flexibility for guests, a home office, or single-level living. Upstairs, two additional bedrooms and a full bath provide a comfortable retreat. The partially finished lower level adds even more usable space for a playroom, gym, or media room. Out back, an oversized composite deck overlooks the expansive, private yard-perfect for summer dinners, entertaining, or simply unwinding outdoors. With central air and easy access to shopping, Metro-North, and major highways, this is a home that makes Fairfield living easy.

271 Jeniford Rd, Fairfield

$998,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24203078 MLS

HANDYMAN SPECIAL WITH GREAT POTENTIAL! Opportunity awaits at 70 Crest Terrace! This property is ready for a new owner with vision to bring it back to life. The home needs updating and repairs but offers plenty of potential for investors, contractors, or buyers looking to renovate and create value. Located in a desirable and convenient area close to shopping, transportation, schools, and local amenities. Property is being sold strictly AS-IS. Short sale and subject to third-party/lender approval. Property condition may limit financing options and may not qualify for FHA financing. Buyer to perform their own due diligence. Bring your ideas, tools, and imagination-great opportunity to renovate, customize, and make this property shine!

70 Crest Ter, Fairfield

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