Real Estate Guidance in Ridgefield and Northern Fairfield County

Set back behind gates in the highly desirable Umpawaug area of West Redding, this private retreat began as a one-room cabin, grew into a farmhouse in the mid-20th century, and was later expanded and reimagined by the current owner. Soaring ceilings, oversized windows, and open living spaces are balanced by intimate rooms, and the European-inspired design pairs historic character with modern comforts. At the heart of the home, the open kitchen, dining, and sitting area is centered on a wood-burning fireplace, creating a natural gathering place for everyday meals and entertaining. Luxury appliances bring modern function to the kitchen. Four bedrooms (first floor primary suite), three and a half baths, an office, living room, entertainment/rec room and laundry room complete the interior. Outdoors, the in-ground pool sits in its own private setting with a separate structure once used as a studio offering potential as a pool house or guest space. The property spans 2.41 acres, with deer fencing around the grounds.

Set on 6.18 picturesque, lightly wooded acres in Redding's equestrian country, this timeless Colonial Cape spans 3,525 sq ft of refined living space, cherished and meticulously maintained by the same family for 37 years. Hardwood floors anchor the main level, leading from a stately living room with brick fireplace and formal dining room to a quiet, dedicated home office. The expansive eat-in kitchen flows effortlessly into an impressive family room showcasing dramatic wood-clad cathedral ceilings with exposed beams. Sliding doors open to a vast wraparound deck overlooking manicured grounds and peaceful woodland, offering an exceptional setting for outdoor gatherings. The upper levels provide exceptional privacy and versatility. The main 2nd floor features three bedrooms and two full baths, including a primary suite with a walk-in closet and dressing vanity. A private staircase leads to a separate fourth bedroom en-suite above the 2-car garage-perfect for an au-pair, guest sanctuary, or in-law suite. The walk-out lower level features a finished recreation room with a billiards table, plus expansive space ready for future expansion. Featuring newer roof and a freshly painted exterior, this private sanctuary is just 5 minutes to schools and town center, and 20 minutes to Metro-North.

Welcome to 75 Carriage, a classic oversized 4- to 5-bedroom Colonial on a sought-after street, just three miles from town and a short walk or bike ride to famous Kent Pond. Enjoy summer days fishing, winter skating, and the swans' annual return, a cherished neighborhood tradition. Set atop one of Wilton's highest peaks, this home offers exceptional privacy on two mature, professionally landscaped acres. Beautiful stonework and a custom oversized outdoor fireplace with a built-in grill create an ideal setting for al fresco dining. Inside, a generously sized gourmet open-concept kitchen features stone countertops, a Wolf range, and a Sub-Zero refrigerator/freezer. Floor-to-ceiling windows fill a light, airy sunroom, while a fireplace keeps the family room just off the kitchen cozy. Steps from the heated garage, a spacious mudroom features radiant-heated floors to keep your toes warm. Above, an expansive private great room features a cathedral ceiling, exposed wooden beams, a fourth fireplace with beautiful stonework, and a wet bar. Upstairs, five bedrooms include three with en suite baths for added privacy; two have oversized soaking tubs for comfort. The primary suite also boasts a radiant-heated bathroom floor, a steam shower, and a walk-in closet. A finished basement with a built-in bar, full bathroom, and sauna completes this home. Room to host. Room to play. A quiet, low-traffic neighborhood to call home.

A SPECIAL OPPORTUNITY TO LIVE IN RIDGEFIELD'S SOUGHT-AFTER TWIXT HILLS COMMUNITY! This charming, 3-story Cape Cod style home offers 3 bedrooms, 2 full bathrooms and a partially finished lower level that provides room for an office, gym or recreation room. Large rooms and comfortable living spaces are ready to accommodate everyday living, entertaining, and quiet moments at home. Recent improvements include: NEW KITCHEN APPLIANCES 2026, REFRESHED BATHROOMS 2026, NEW UPPER LEVEL FLOORING 2026, FRESHLY PAINTED UPPER LEVEL 2026, NEW OIL TANK 2026, NEW WELL HOLDING TANK 2026, NEW GARAGE DOORS 2026, NEW FRONT DOOR,NEW ROOF 2025, & MORE! Privately set on an elevated, low-maintenance 3.3 acre property, this home offers a wonderful sense of privacy and is surrounded by the natural beauty of its setting. And, the Twixt Hills lifestyle adds to the desirability of this home. Twixt Hills residents enjoy access to Pierrepont Lake, where summer days can be spent swimming, kayaking, fishing, or simply relaxing at the neighborhood beach. It's a community where neighbors connect, outdoor recreation is part of everyday life, and seasonal gatherings create a wonderful sense of belonging. Enjoy nearby hiking and nature trails, while the shops, restaurants, cultural attractions, and the charm of downtown Ridgefield are just a short drive away. A wonderful opportunity to enjoy the best of neighborhood living, natural surroundings, and the welcoming character of Ridgefield!

Welcome to 20 Acre Lane, a lovingly maintained three-bedroom, two-full-bath raised ranch set on a level 1.01-acre property on a quiet cul-de-sac in desirable southern Ridgefield. Cherished by the same owners since 1988, this inviting home offers comfortable living spaces and abundant natural light. Highlights include a vaulted living room ceiling, a primary suite with full bath, a fireplace in the finished lower level, a separate laundry room, a two-car garage and an oversized screened-in porch overlooking the flat, usable yard and established perennial gardens. NUMEROUS SIGNIFICANT improvements provide peace of mind, including 2025 Hardie Board siding with extensive exterior upgrades, newer living and dining room picture windows, a 2014 roof with transferable lifetime warranty, foundation drainage, a new exterior Roth oil tank, chimney pointing and a 2026 whole-house generator with automatic transfer switch. Additional updates include interior painting and refinished hardwood floors. Town water, a practical raised-ranch layout and a convenient location with easy access to Ridgefield's picturesque downtown, lower Fairfield County and New York add to the appeal. A special opportunity to make a well-cared-for home your own and enjoy top-rated schools! Schedule your private showing and experience all that 20 Acre Lane has to offer.

Exceptional opportunity to purchase 2 approved building lots in Ridgefield on 2.76 picturesque acres with driveway access off of Mountain Road in Redding. This offering includes 3 parcels: Lot 1 West Branchville Road, Ridgefield (Parcel # 2697551, 1 Acre, RA zone, taxes $5,360); Lot 2 West Branchville Road, Ridgefield (Parcel # 2697552, 1 Acre, RA zone, taxes $5,360); plus 13 Mountain Road, Redding (Parcel # 271574, R-2, taxes $2,748). Driveway access through Mountain Road was previously approved in Redding for both lots, but would have to be resubmitted since it was over one year ago. Septic testing was done in 2025, and the engineer stated that up to 30-35 bedrooms could be available based on the soil testing if someone wanted to get creative and consider doing multiple homes instead of traditional single family homes, but it would require special permits. Documents are attached showing some proposed concepts, but nothing has been permitted or approved and it would be up to the buyer to do all due diligence in terms of feasibility and zoning.

Add'l photos coming soon. Some homes offer more than a place to live. They offer a lifestyle rich in character, beauty, and privacy. Set behind gates on 3.3 beautifully landscaped acres, this remarkable 1912 Ridgefield retreat, listed on the National Register of Historic Homes, blends vintage charm with thoughtful modern living. Five fireplaces create inviting gathering spaces, while abundant windows bring the beauty of the outdoors inside. The spacious eat-in kitchen, added in 1987 and updated in 2023, is perfect for everyday living and memorable gatherings. A sun-filled main-level primary suite, added in 2022, offers exceptional comfort and convenience. Upstairs, the rear bedroom features a balcony with hot tub: enjoy sunsets from the tub year round! Outdoors, extraordinary landscaping, peaceful privacy, and breathtaking sunsets provide a beautiful backdrop for entertaining or simply enjoying nature. A truly distinctive feature is the approximately 2,200 SF garage, originally the carriage house for neighboring Sunset Hall. A car enthusiast's dream, it features a mechanic's pit, vehicle lift, heated area, and unfinished space with exciting possibilities for recreation, studio, or potential ADU, subject to approvals. Incredible location for convenience and easy commutes! Rich in history yet wonderfully livable, this is a place to savor life's everyday pleasures in extraordinary surroundings.

Extraordinary, beautifully updated six-bedroom Colonial, where timeless architecture meets modern luxury. Set on an impressive 2.42-acre estate, this property offers a rare blend of privacy, scale, and refined presence creating a true retreat just moments from everyday conveniences. A sweeping wraparound driveway delivers a grand and memorable arrival, complementing the home's stately facade while providing ample parking in addition to the attached two-car garage perfectly suited for hosting guests and effortless daily living. Step inside to a gracious foyer adorned with refinished hardwood flooring that flows seamlessly throughout the main level, setting a warm yet sophisticated tone. The foyer opens into an elegant living room, where a classic fireplace anchors the space, offering both ambiance and timeless character. The home's thoughtfully designed open-concept layout effortlessly balances traditional charm with contemporary living, creating an inviting setting for both intimate moments and large-scale entertaining. At the heart of the home lies a stunning, fully updated kitchen designed to impress. Featuring sleek quartz countertops, stainless steel appliances, and beautifully refreshed cabinetry, this space delivers both style and functionality. The expansive eat-in area provides ample room for casual dining and transitions seamlessly to a large rear deck an ideal extension of the living space. Here, you can take in the beautiful scenic views.

Idyllic country charm meets modern luxury in this turnkey Cape Cod home, nestled on 3.24 private acres complete with your own tranquil, spring-fed pond! Step inside through a dramatic two-story entry to find gleaming, richly-hued hardwood floors flowing seamlessly throughout the entire home. Thoughtfully designed for both entertaining and everyday comfort, the layout features elegant formal living and dining rooms bathed in natural light. At the heart of the home is the chef's kitchen with chic creamy-white cabinetry, timeless soapstone countertops, premium appliances, and a generous center island. It opens directly to an inviting family room anchored by a cozy fireplace and sunny bay-window seating and to a charming screened porch. The highly desirable main-level primary suite serves as a peaceful retreat, featuring a lavish en-suite spa-inspired bath designed for pure relaxation. Upstairs, you will discover three generously proportioned bedrooms, a stylishly updated full bath, and an expansive bonus room illuminated by bright skylights-a versatile space ready to become your home office, private gym, media lounge, or playroom. Peace of mind comes built-in with extensive improvements, including fresh exterior paint (2023), a comprehensive kitchen renovation (2021), a new roof (2015), updated interior painting (2015-2021-2026), and a stylishly renovated hall bath(2022). A truly ideal blend of classic architectural charm, modern luxury, and scenic country privacy. A win-win!

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary suite offers its own stone fireplace and a luxurious bath with radiant heated floors. The kitchen is equipped with Wolf, Bosch, and Liebherr appliances. The dining room features a hidden dry bar and a glassware cabinet, with sliders to the top deck for outdoor dining if desired. Upstairs, there are three additional bedroom suites with updated baths, plus a smaller third-floor bedroom ideal for an office or flex space. The finished walk-out lower level includes radiant heat, a bedroom, a full bath, an office, a gym, laundry, and a kitchenette. Outdoors, enjoy a heated Gunite pool and spa with a bluestone patio, surrounded by serene woodland views. Additional features include the Sonos system, whole-house generator, and air purification. Minutes to town and top-rated schools, this move-in-ready retreat is ideal for weekend or year-round living.

Exceptional Lower Weston Location | Nearly 5 Acres | Endless Possibilities A rare opportunity to own nearly 5 magnificent acres on one of lower Weston's most sought-after streets! Set amid beautiful, private grounds with a swimming pool and tennis court, 43 Kettle Creek offers an extraordinary setting for your dream country estate, just minutes from Westport. Rich in character and timeless charm, this classic 1930s home showcases original hardwood floors, a gracefully curved staircase, custom built-ins and 4 fireplaces. Sun-filled living spaces include gracious formal rooms, an inviting family room and a flexible first-floor den or bedroom with full bath. Upstairs, the primary suite features a fireplace and dressing room, complemented by 3 additional bedrooms. Bring your imagination, vision and toolbox to restore this special home to its former glory, or explore the possibilities of a fresh start with a custom-built residence on this exceptional property. With nearly 5 acres, a coveted lower Weston address and convenient access to Westport, schools and nature trails, the possibilities are as compelling as the setting. A remarkable piece of Weston real estate, ready for its next chapter!

Set on a private acre in Wilton, this 2001 Colonial offers 4 bedrooms and 4,228 square feet of finished living space, with the versatility to suit every stage of life. The eat-in kitchen features granite countertops, a center island, double wall ovens, and pantry, opening to the family room and an expansive deck overlooking the backyard and seasonal hillside views. Formal living and dining rooms offer inviting spaces to entertain, with a fireplace and tray ceiling. Upstairs, the primary suite includes a walk-in closet and bath with soaking tub, dual vanities, and separate shower, plus three additional bedrooms and second-floor laundry. The finished walk-out lower level offers exceptional flexibility with a fifth bedroom or home office, recreation room, and full bath with steam shower, along with potential for in-law or au pair accommodations. Above the 3-car garage, a finished bonus room provides even more possibilities for a home gym, studio, playroom, or media room. Enjoy the privacy of North Wilton while being just 0.6 miles from Georgetown's restaurants, cafes, and shops, with convenient access to Cannondale and Branchville Metro-North stations for NYC commuting. Additional highlights include public water, a full roof replacement in 2021, and proximity to parks and hiking trails.