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$755,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24176561 MLS
!!!ASSUMABLE 3% VA LOAN - APPROX. $468,000 BALANCE!!! A rare opportunity to secure a substantial portion of your financing at just 3% on this fully renovated Fairfield two-family! Current rents total $4,650/month and are believed to be below market, creating a compelling opportunity for owner-occupants and investors alike. Live in one unit and let the other help offset your housing costs or add a turnkey income-producing property to your portfolio. Completely renovated and thoughtfully updated from top to bottom, the home features a 1 bedroom, 1 bath first-floor apartment & a 3 bedroom, 1 bath apartment spanning the 2nd & 3rd floors. Both units offer updated kitchens with quartz countertops, custom white cabinetry, stainless steel appliances and designer tile backsplashes, along with renovated baths, crown molding, recessed lighting, updated flooring and neutral contemporary finishes. The upper unit includes flexible living space, a dedicated office/flex room and walk-in closet. Instant hot water heaters & extensive renovation work offer added efficiency & peace of mind for years to come. Outside, enjoy a covered front porch, multi-level rear decks, & a fully fenced backyard with fire pit area w/cafe lighting. Convenient to schools, shopping, restaurants, parks, Metro-North &major commuting routes. Current rents: $1,925 for the 1BR & $2,725 for the 3BR. Loan assumption subject to servicer approval & buyer qualification. !!!ASSUMABLE 3% VA LOAN - APPROX. $468,000 BALANCE!!!

241 Old Stratfield Rd, Fairfield
$719,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24170490 MLS
A unique opportunity to own this side-by-side two-family home in a sought-after neighborhood. Offering exceptional value and versatility, this property is ideal for investors, owner-occupants, or multigenerational living. Unit One features a bright and inviting living room, Bedroom, an eat-in kitchen, and a full bath. Filled with natural light, the space offers a warm, comfortable atmosphere with direct access to a private patio and shared fenced yard-perfect for relaxing or entertaining. Unit Two offers two generously sized bedrooms, a spacious eat-in kitchen with in-unit laundry, and two full baths. The large living room with a cozy fireplace creates a welcoming centerpiece, while the three-season room-with private access-provides an ideal space for a home office, den, or quiet retreat. Enjoy outdoor living in the well-maintained yard, complete with a private patio-perfect for morning coffee, gatherings with friends, or summer barbecues. Additional highlights include a two-car attached garage and private driveway for ample parking. Conveniently located near beaches, golf courses, parks, shopping, top-rated schools, major highways, and the train, this home offers the perfect balance of suburban tranquility and urban accessibility. Whether you're looking for a place to call home or a smart investment opportunity, this property delivers strong rental potential in a highly desirable location.

282 Marlborough Ter, Fairfield
$765,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24177411 MLS
A home well loved. Step inside this 1920's Stratfield charmer that has been cared for by the same family for 45 years. You will love greeting your guests in the spacious entry that has 2 closets, a built in bench and marble travertine tile floor. The open feel of the first level allows for effortless entertaining flow and an abundance of natural light. Don't miss the custom fireplace mantle and surround, beautiful crown moldings, raised panel and floor to ceiling built-ins. Tucked away off the kitchen is the comfortable family room offering a vaulted ceiling, beams and custom built -ins. Updates include a remodeled kitchen ~ 2 newer full baths ~ central air conditioning ~ electricity upgraded to 200amp and portable generator ready ~ 3 zone cozy hot water heat ~ some newer windows ~ 20x20 Trex deck ~ custom 1 car garage complete as a workshop with wood burning stove. Don't miss the 10x14 finished home office with closet in the lower level. The backyard is just perfect with the beautiful flowering plants and an herb garden that has already been started for the new owner. Convenience of living in Stratfield is found by walking to Stratfield Elementary, The Goddard School and shopping conveniences at the Four Corners. Become a part of the exciting Stratfield Village known for its cherished sense of community and Apple Pie charm as quoted by the NYTimes.

189 Church Hill Rd, Fairfield
$925,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24176507 MLS
This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With trails leading directly from the back door to a secluded pond and hiking paths, it serves as an ideal weekend retreat and a convenient alternative to the Vermont or Connecticut River Valley. Located only 70 minutes from Grand Central via the Westport train station, this home offers easy access to both the Connecticut coastline and deep woods.

11 Judges Hollow Rd, Fairfield
$4,500
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24176822 MLS
Luxury rental! Brand new apartment building. All inclusive living walking distance to Fairfield Metro Train station. Spacious three bedroom, two bathrooms, Partially furnished open floor plan with modern clean lines. Eat In kitchen, Quartz counters and stainless steel appliances. Large bathrooms. Handicap accessible complex, underground parking and elevator. Washer and dryer in unit. Walk to Train, shops, restaurants and all public transportation. Must have no evictions, good references and income. Use rent spree to apply.

528 Black Rock Tpke Unit 307, Fairfield
$1,650,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24173535 MLS
Welcome to this exceptional fully reimagined home at 101 Applegate Road, perfectly set on a quiet, walkable horseshoe street just off Fairfield Woods Road in one of Fairfield's most desirable neighborhoods. This thoughtfully designed 4-bedroom, 3 full and 1 half bath home blends timeless style with modern functionality, offering the ideal layout for today's lifestyle. Step inside to a bright, open floor plan featuring gleaming hardwood floors and high-end finishes throughout. The heart of the home is a stunning, designer kitchen with premium appliances, custom cabinetry, and a spacious island-perfect for everyday living and effortless entertaining. The kitchen flows seamlessly into the main living and dining areas, creating a warm and inviting atmosphere. Upstairs, the primary suite offers a private retreat with a beautifully appointed bath and generous closet space, while three additional bedrooms provide flexibility for family, guests, or a home office. Every detail has been carefully curated, delivering all the bells and whistles buyers expect in new construction. Set in a peaceful yet convenient location, you'll enjoy easy access to schools, shopping, dining, and everything Fairfield has to offer-while still feeling tucked away in a quiet neighborhood setting. A rare opportunity to own an architecturally redesigned and rebuilt home of in an established, sought-after Fairfield location.

101 Applegate Rd, Fairfield
$12,000,000
7 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24161896 MLS
This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was expertly restored, and all systems upgraded and integrated. The expanded footprint incorporates 7 bedrooms and 7 full baths, all with views over the open landscaped property. Lofty ceilings and walls of glass create magical interior spaces, a perfect setting for an art collector. Separate wings radiate off the main rooms. Each space has impeccable thoughtful detail. A hidden screening room , a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, and pool, make this a perfect athlete's compound. An office pavilion is set privately in a quiet garden area. The landscape offers open vistas, meadows and an orchard. Live in ultimate style and easy elegance at this private retreat a quick commute to NYC and airports.. A private haven surrounded by a 155 acre nature preserve just minutes to Westport, Greenwich, and convenient to NYC and airports.

4800 Congress St, Fairfield
$2,650,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24173048 MLS
A gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport town await. Natural beauty, brilliant architecture, craftmanship & updates combine to make this home a standout. Featuring 12 rooms flooded w/ light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to peaceful snow-covered landscapes. The living room fireplace provides a cozy focal point w/ oversize French doors that open to the patio creating an ideal setting for outdoor dining & hosting. The eat-in kitchen offers so much w/ dining area, island, pantry & state of the art appliances & guides you to the dining room, office, living room & study. Upstairs the beauty continues w/ 4 large bedrooms including the primary. The lower level expands the living space w/ a new mudroom, rec room, gym & half bath. Numerous updates throughout include a new lower level, flagstone patio, custom pantry w/ wine storage, upgraded laundry room w/ new washer, new window in en-suite & new Rubbermaid track system. Step outside to your patio featuring a built-in Weber BBQ & XL Big Green Egg, perfect for cooking enthusiasts. The exterior has been meticulously maintained w/ repainting, stone-accented walls, Belgium block-lined driveways & ongoing landscaping. A NE bridge adds character. The Patterson Club is a bike ride away. 3007 Redding Road is filled w/ light, space & lasting memories for its next chapter.

3007 Redding Rd, Fairfield
$5,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24171990 MLS
Brand New Contemporary Townhouse never occupied! All new kitchen and appliances! Large pantry and wine chiller in kitchen. Open floor plan. Office space on main floor. Half bath on main floor. Light bearing room living room. Slider to private patio on main floor. 3 Bedrooms upstairs with large closets. Main Bedroom with ensuite. Finished lower level with 1 car garage under the house. Spacious, new, inviting, home and will allow 2 cats or 2 dogs. Good credit and references needed. 1st, last and one month security. Private patio and yard. Come and see! Close to I95 and Merritt Parkway. Close to schools. Do not miss!!

62 Soundview Ave, Fairfield
$2,275,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24171406 MLS
3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose.

3808 Redding Rd, Fairfield
$565,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24166691 MLS ⋅ Stone Ridge At Fairfield BLDG.
Luxury living in a gated community across from the Fairfield-Blackrock Train Station, close to the Whole Foods Shopping Center and restaurants. This sophisticated 1 Bedroom 1.5 Bathroom unit includes a sunny deck overlooking the community. Extraordinary appointments and impeccable design elements such as 9'+ ceilings throughout, hardwood floors, and a gourmet kitchen with stainless steel Viking appliances. The primary bedroom suite includes a marble bathroom with a spa tub and a spacious shower stall, hallmarks of a Stone Ridge home. Residents have access to various amenities, including the stunning Ridge Club, which offers a continental breakfast daily in the Community Room, a Fitness Center, a Concierge/Manager, and a Porter/Handyman, which elevates condominium living to new heights. Enjoy Fairfield's beaches, lakes, two public and two private golf courses, public tennis course, downtown shopping, restaurants, and much, much more. Reserved Parking Space No. 5. This property is also for rent. MLS- 24167315

50 Stone Ridge Way Unit 2A, Fairfield
$995,000
ACTIVE Status ⋅ 24166279 MLS
CHESTNUT GROVE - Wonderful opportunity to enhance an extraordinary, sweeping 2.39 acre parcel in a beautiful and bucolic Greenfield Hill location. This expansive property nestled within a Chestnut Grove, features a stately Barn providing Garage storage suitable for farming equipment and motor vehicles, and a recently constructed second story Studio Apartment enjoying a haven of privacy and seclusion. The sun-lit Great Room presents a fully equipped Kitchen with cabinetry and Breakfast Bar, Laundry with stack washer and dryer, and a beautifully tiled full bath with shower. Currently taxed under Farm Status. NEW ASSESSMENT FOR TAX YEAR 2026 -2027 IS $611,450.

Fairfield
$995,000
1 Baths ⋅ ACTIVE Status ⋅ 24166262 MLS
CHESTNUT GROVE - Wonderful opportunity to enhance an extraordinary, sweeping 2.39 acre parcel in a beautiful and bucolic Greenfield Hill location. This expansive property nestled within a Chestnut Grove, features a stately Barn providing Garage storage suitable for farming equipment and motor vehicles, and a recently constructed second story Studio Apartment enjoying a haven of privacy and seclusion. The sun-lit Great Room presents a fully equipped Kitchen with cabinetry and Breakfast Bar, Laundry with stack washer and dryer, and a beautifully tiled full bath with shower. Currently taxed under Farm Status. NEW ASSESSMENT FOR TAX YEAR 2026 - 2027 IS $611,450

3509 Redding Rd, Fairfield
$1,100,000
ACTIVE Status ⋅ 24166265 MLS
An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Com. for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill. With its driveway access on Brett Road, a designated "Scenic Road," the lot faces the beauty and character of historic Congress Street. The location is unmatched: moments from the 186-acre Brett Woods Conservation Area and the 155-acre Roy and Margot Larsen Wildlife Sanctuary, both featuring miles of walking trails, and equally convenient to the town centers of Fairfield, Westport, and Southport. There are currently no other similarly sized lots available in Greenfield Hill, making this a rare and valuable opportunity. All of this is just one hour from Manhattan, offering an ideal blend of tranquility, convenience, and prestige.

22 Brett Rd, Fairfield
$8,500
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24164022 MLS
Brand-new 2026 construction offering over 3,200 square feet of thoughtfully designed living space-an exceptionally rare opportunity to rent a new construction home in Fairfield. This five-bedroom, four-and-a-half-bath residence features a highly functional modern layout with high-end finishes throughout, including hardwood floors, quartz countertops in the kitchen and bathrooms, custom cabinetry, and a gas fireplace. Option for main-level primary bedroom. This alternate primary suite includes an en-suite bath and offers an excellent setup for guests, in-laws, or anyone seeking stair-free living. The main level also features an open-concept kitchen, dining area, and family room with sliding doors to the rear patio, along with a welcoming foyer, mudroom, and half bath. Upstairs are four bedrooms, including a spacious primary suite with a double vanity, oversized shower, and a large walk-in closet with custom shelving. Three additional bedrooms share a hall bath, and a dedicated second-floor laundry room adds everyday convenience. The lower level adds approximately 725 square feet of bright, flexible living space with windows, natural light, sliding doors to the rear yard, and a full bath-creating another opportunity for an in-law or guest setup. Available June 1st, 2027 for a year: $8,500 per month ($9,500 per month furnished) Summer 2027 furnished: $8,500 per month. 2027-2028 academic year furnished: $12,500 2027-2028 academic year unfurnished: $11,750

108 New England Ave, Fairfield
$2,300
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24152091 MLS
Bright, exceptionally spacious second floor two bedroom apartment with formal diningroom/office/flex space, updated eat in kitchen and bath, freshly painted with shining hardwood floors throughout. Conveniently located on the quiet end of Knapps Highway with easy access to shopping, Metro Center RR Station, schools and public transportation. Tenant has use of an extensive yard as well as their own separate patio. Basement Storage w/d new stackable unit. Landlord responsible for lawn and snow removal, trash and water.

720 Knapps Hwy, Fairfield
$15,000,000
7 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24104335 MLS
The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

4800 Congress St, Fairfield
$7,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24131226 MLS
Available for Winter/AY Rental August of 2027-June 2028. Rent could increase for future summer months depending on terms and contract length. Kayaks and Stand Up Paddle Boards available for lakeside fun! Conveniently located just minutes from the train station, shops, and restaurants and just 3 miles from Fairfield and Sacred Heart Universities. This newly updated waterfront home is located directly on Samp Mortar Reservoir which is the charming centerpiece of the Lake Hills Community. Beautiful homes surround the 47-acre body of water and community members enjoy the waters for boating, fishing, and swimming. With five different beaches on the lake, there is always a sandy shore to relax on. The finished lower level with a fireplace is great for game nights and the brand new terraced patio allows for full use of the yard, while enjoying the sights and sounds of the lake. Sleeps up to 5 adults.

151 Sasapequan Rd, Fairfield

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