Fairfield County, Connecticut Land For Sale (59 results)

Welcome to Park Hill, a legacy property--reimagined for the way you live today. This 1923 English Manor tucked within a prestigious private association, offering the perfect escape just moments from NYC. Thoughtfully updated for today's lifestyle while preserving its timeless architectural pedigree, this is a rare opportunity to own a true Greenwich estate with the ease and sophistication sought by buyers. Set on 1.81 acres of private, park-like grounds, the property delivers the kind of space, quiet and natural beauty that feels worlds away--yet remains effortlessly connected. Grand-scale entertaining rooms, multiple living spaces and refined interiors create an ideal setting for both elegant gatherings and everyday living. Amenities include an indoor pool and private gym. Originally built in 1923 in the English Tudor Revival style and enhanced with 2025 updates, Park Hill seamlessly blends historic character with modern luxury. The indoor pool and private gym--bringing a full-wellness experience home--along with a three-car garage and circular driveway that lend both convenience and presence. With a a fully approved and engineered accessory structure/cottage, new gas line, new water line, new septic and more, the estate also offers future flexibility to expand or customize. Located just minutes from town, schools and Metro-North, 21 Calhoun Drive provides the rare combination of privacy, prestige, and proximity that discerning buyers demand.

Nestled in a private wooded setting and set well back from the road, this large custom Colonial offers the perfect blend of space, comfort, and convenience. Featuring five bedrooms, including a spacious primary suite with its own full bath, the home is designed for both everyday living and entertaining. Hardwood floors flow throughout, adding warmth and timeless appeal. The spacious eat-in kitchen serves as the heart of the home and opens directly to a large, very private deck, creating an ideal space for outdoor dining, relaxing, or enjoying the peaceful surroundings. A formal dining room provides an elegant setting for gatherings, while the main-level laundry area adds everyday convenience. With two full baths and one half bath, there is plenty of room to accommodate family and guests. The finished lower-level recreation room offers additional living space perfect for a family room, game room, home gym, or office. Located in a desirable neighborhood with a convenient commute, this home combines the tranquility of a secluded retreat with easy access to work, shopping, and local amenities.

Commandingly sited above the Aspetuck River, this exceptional 9,600+ sq ft cut stone manor offers sweeping views of a 40 acre horse farm and an estate setting rarely available. A long, stately driveway sets a grand first impression, opening to a large courtyard framed by manicured boxwoods. As you enter the home, a grand hall and great room with a dramatic view of the outdoor waterfall establishes the scale and craftsmanship found throughout. The custom kitchen blends beauty and function with a SubZero armoire style refrigerator and freezer, double Viking gas range, and dual Fisher & Paykel dishwashers. A separate full caterer's kitchen-with additional refrigeration, dishwasher, and oven-supports effortless entertaining. Sun filled formal rooms, a richly detailed library, and a stunning river view sunroom showcase the home's craftsmanship. Wide plank cherry floors, solid cherry doors, and a custom wet bar with soapstone counters, built-in entertainment center, and tin ceiling add warmth and character. An elevator services all three levels. Six fireplaces, a walk-in wine room, and a media room with stadium seating elevate the lifestyle experience. A private caretaker/au pair apartment with its own entrance provides flexibility. With 6 garages, expansive lawns, and complete privacy-yet only 65 miles from NYC-this residence delivers an extraordinary blend of beauty and serenity.

This exceptional home offers a two-story entryway and over $300K in recent upgrades and a rare opportunity to enjoy resort-style living. Located in a neighborhood of spacious, high-end homes, this property offers a peaceful, low-traffic setting with multiple cul-de-sacs. The outdoor setting is a standout, featuring a stunning pool, year-round spa, built-in grill, stone walls, expansive patio, and multiple entertaining areas, all designed for effortless indoor-outdoor living. Car enthusiasts will appreciate the 3-car garage, fully remodeled and enhanced with a premium epoxy flooring, along with all-new garage doors. The spacious kitchen features abundant cabinetry, granite counters, Sub-Zero, gas cooktop, double wall ovens, and a pantry-all overlooking the private backyard oasis. A casual dining area opens directly to the deck with a retractable awning. Elegant formal living with gas fireplace and dining room provide refined gathering places while the family room offers a wet bar and second gas fireplace for relaxed evenings. The impressive two-story foyer leads to a fully remodeled office, updated powder room, and generous closet space. Upstairs, a gorgeous balcony overlooks the foyer and leads to the primary suite with cathedral ceilings, dual walk-in closets, and a beautifully updated bath. Three additional bedrooms include one with a new, luxurious en-suite bath plus a newer full bath with double sinks and quartz counters. There's too many wonderful features to mention! Please reach out for full list of upgrades. There are also floor plans, a Matterport virtual tour, and a full walkthrough video. The finished walk-out lower level adds flexible living space with new luxury vinyl flooring, ideal for a gym, recreation, or media room, and includes a convenient 1/2 bath with direct access from the pool and patio. Extensive upgrades include 2 electric vehicle outlets in garage, fully updated bathrooms, owned solar panels, updated heating and cooling systems, newer pool equipment and liner, whole-house generator, security system, irrigation, refinished hardwood floors, and extensive landscaping. Ideally located near Tashua's premier amenities, this home is just moments from Tashua Recreation Center with lighted pickleball, tennis, basketball, and a championship golf course, along with a selection of highly regarded local restaurants. Enjoy convenient access to major highways and Metro-North train service, and highly regarded Trumbull schools, including Tashua Elementary School, Madison Middle School, and Trumbull High School, recently rated 10/10 on GreatSchools. A rare opportunity to enjoy resort-style living with your own private pool and year-round hot tub, just moments from championship golf and premier recreation-this is a dream home. Be sure to check out the Virtual Tours - we have both a Matterport Virtual Tour with measuring tool and a full walkthrough video showcasing this home's wonderful features. (Back on the market due to buyer's failure to secure financing!) Hurry to see this beautiful and sophisticated colonial with pool in sought-after Tashua.

Tucked away at the end of a long private driveway in Wilton's desirable Thunder Lake neighborhood, this charming center hall Colonial offers exceptional privacy and tranquility. Set on 2.45 acres and surrounded by protected state land, the property enjoys a secluded setting while remaining just minutes from shopping, dining, schools, and everyday conveniences. Beautiful hardwood floors run throughout the home. The main level features a spacious living room, formal dining room, and an inviting family room with a wood-burning fireplace and sliders leading to an expansive deck overlooking the private backyard and gazebo. The centrally located kitchen offers views of the private setting and convenient access to the home's gathering spaces and outdoor living areas. Upstairs are four generously sized bedrooms, including a primary suite, along with an oversized great room offering flexibility as a potential fifth bedroom, home office, media room, or guest space. The finished lower level includes a dry bar and additional living space, while a large workshop and storage area with exterior access provides endless possibilities. Recent improvements include a freshly painted exterior, new main roof, new HVAC system, and new flooring. Enjoy easy access to nearby Weir Farm National Historical Park and Wilton Town Forest with miles of scenic trails. A rare opportunity to enjoy space, privacy, and convenience in one of Wilton's most sought-after locations.

Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a two-car detached garage, a sauna and spa room, Tabacco Barn & an expansive horse barn with fully operational paddocks complete with water and electricity. The artist's extraordinary vision brings the estate to life, creating a museum-quality residence that embodies elegance and sophistication. Rare materials and uncompromising attention to detail are evident throughout, including white oak hardwood floors sourced from MOMA, custom handmade mahogany windows fitted with imported wavy German glass, and advanced argon gas insulation. The chef's kitchen is thoughtfully designed with gnarled brass pulls, leathered limestone marble countertops, and a handmade, hand-painted tile backsplash. The retreat was constructed using Pennsylvania Lichen Stone, with stone walls and pillars carefully built to replicate the craftsmanship of centuries past. Bronze metal seamed-heated roofs, snow guards, and cupolas crown each structure, providing both durability and architectural distinction. The grounds are beautifully landscaped with rows of English dwarf boxwoods.

Welcome Home to 7 Jet Brook Road! This stunning, light-filled with an open layout 4-BR, 3.5-BA home built in 2017 is beautifully situated on a private 2.12 acre lot in desirable Newtown. This meticulously maintained residence boasts gleaming hardwood floors and offers a thoughtful floor plan featuring a formal dining room with coffered ceilings, a separate living room, first floor home office or guest room and a large bright and inviting family room with recessed lighting and a beautiful gas fireplace. The chef's kitchen is perfect for entertaining as it has an expansive granite island, stainless steel appliances, tons of storage, includes a pantry and walks out to the back deck with a gas-grill hookup for effortless entertaining. First floor laundry room adds to the many conveniences in this home. Upstairs highlights include a primary suite with a tray ceiling adding to it's architectural drama, a walk-in closet, large en suite bathroom with tile shower, granite counters and a soaking tub with private views. Two more full baths add convenience to the remaining three bedrooms and second office or playroom option. The beautifully finished walk-out basement with extensive wood trim hosts a playroom and gym option and a large 3-car garage. Modern essentials like a whole-house generator, radon system, storage shed (added in 2021) make this home move-in ready and worry-free. Entertain in the evening outside on your maintenance free deck or around the fire pit!

Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate seamlessly pairs vintage authenticity with ultra-luxury modern updates. Inside, original architectural integrity shines. The spectacular great room features a double-height wood-beamed ceiling, a stunning original paned picture window, and custom staircase balusters subtly crafted to resemble musical staff notes. A country-chic chef's kitchen boasts elite appliances (La Cornue, Miele, Bosch), a cozy built-in banquette, and a fireplace inset with original vintage tile. The second-level primary suite offers panoramic views of the lush, pastoral grounds, a luxurious marble bath, and an expansive walk-in closet. Retain your own inspiration in the original music studio/office where Ives composed, complete with untouched original hardwood floors. The extraordinary 18-acre grounds double as a private resort, featuring a charming 1BR guest cottage (ca. 1900), a heated Gunite infinity-edge pool and spa, a tennis court, and a classic century-old timber frame barn with a new foundation and roof. Effortlessly sophisticated, enchantingly rustic, a rare opportunity and an absolute masterpiece of living history. A masterclass in historic preservation and modern luxury, this estate underwent an extensive, top-tier restoration from 2012-2022. The main residence seamlessly blends original architectural details-including meticulously matched windows and original flooring-with world-class comforts. At the heart of the home is a bespoke custom kitchen featuring a cozy fireplace, a built-in dining banquette, and elite appliances (La Cornue, Miele, Bosch). The sumptuous primary suite serves as a private sanctuary, complete with a luxe spa-bath and an expansive walk-in closet. No detail was overlooked in the mechanical and structural renewal, which includes completely upgraded systems (gas/propane heat, central AC), a 30KW generator, and all-new cedar and metal roofing. The exterior preservation extends to a restored barn with a new foundation, a screened side sun porch with stone flooring, and a charming second-level sleeping porch. Outside, the beautifully landscaped grounds feature a spectacular 2015 Signature Pools gunite infinity-edge pool and spa. Completing this rare compound is a fully renovated, circa-1900 one-bedroom guest cottage boasting vaulted beamed ceilings, a galley kitchen, laundry, and dedicated central air/heat. An unparalleled offering of turnkey sophistication.

Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate seamlessly pairs vintage authenticity with ultra-luxury modern updates. Inside, original architectural integrity shines. The spectacular great room features a double-height wood-beamed ceiling, a stunning original paned picture window, and custom staircase balusters subtly crafted to resemble musical staff notes. A country-chic chef's kitchen boasts elite appliances (La Cornue, Miele, Bosch), a cozy built-in banquette, and a fireplace inset with original vintage tile. The second-level primary suite offers panoramic views of the lush, pastoral grounds, a luxurious marble bath, and an expansive walk-in closet. Retain your own inspiration in the original music studio/office where Ives composed, complete with untouched original hardwood floors. The extraordinary 18-acre grounds double as a private resort, featuring a charming 1BR guest cottage (ca. 1900), a heated Gunite infinity-edge pool and spa, a tennis court, and a classic century-old timber frame barn with a new foundation and roof. Effortlessly sophisticated, enchantingly rustic, a rare opportunity and an absolute masterpiece of living history. A masterclass in historic preservation and modern luxury, this estate underwent an extensive, top-tier restoration from 2012-2022. The main residence seamlessly blends original architectural details-including meticulously matched windows and original flooring-with world-class comforts. At the heart of the home is a bespoke custom kitchen featuring a cozy fireplace, a built-in dining banquette, and elite appliances (La Cornue, Miele, Bosch). The sumptuous primary suite serves as a private sanctuary, complete with a luxe spa-bath and an expansive walk-in closet. No detail was overlooked in the mechanical and structural renewal, which includes completely upgraded systems (gas/propane heat, central AC), a 30KW generator, and all-new cedar and metal roofing. The exterior preservation extends to a restored barn with a new foundation, a screened side sun porch with stone flooring, and a charming second-level sleeping porch. Outside, the beautifully landscaped grounds feature a spectacular 2015 Signature Pools gunite infinity-edge pool and spa. Completing this rare compound is a fully renovated, circa-1900 one-bedroom guest cottage boasting vaulted beamed ceilings, a galley kitchen, laundry, and dedicated central air/heat. An unparalleled offering of turnkey sophistication.

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

Welcome to lakefront living at its finest on Candlewood Lake. Set on a private, level waterfront lot with over 450' of shoreline, this exceptional 3-bedroom home, rebuilt in 2005, offers breathtaking panoramic views and more than 6,000 SF of living space in one of the lake's most coveted settings. Designed for comfortable living and entertaining, the spacious main level flows seamlessly from inviting living and family rooms into an open kitchen and dining area. Generously sized rooms throughout provide comfort and flexibility, while every room enjoys stunning water views, creating an extraordinary connection to the lake. The lower level offers additional living space ideal for guests, fitness, hobbies, or entertaining, with direct access to the outdoor living areas and waterfront. Outside, professionally landscaped gardens frame the property and create a beautiful backdrop for lakeside living. Relax on the patios, enjoy the private dock, or simply take in the ever-changing scenery. The level shoreline provides effortless access to the water, a rare and highly sought-after feature on Candlewood Lake. Just 75 miles from Manhattan, this remarkable property offers the perfect balance of peaceful waterfront living and convenient access to New York City. A detached garage with bonus space above provides added flexibility. Located in the sought-after Hollywyle community, this is more than a home-it's a rare opportunity to experience the very best of Candlewood Lake.

Set privately on one of Newtown, Connecticut's most sought-after streets, 29 Greenleaf Farms Road delivers a refined luxury lifestyle with exceptional indoor and outdoor living. Thoughtfully updated throughout, this impressive residence combines timeless craftsmanship with modern amenities designed for comfort, entertaining, and everyday elegance. The heart of the home features a stunning chef's kitchen appointed with premium Miele appliances, including a 36-inch refrigerator and matching 36-inch freezer positioned side-by-side for a seamless custom look. Natural light pours into the dramatic cathedral ceiling great room highlighted by skylights and an open, airy feel. A dedicated home office, wine cellar, and prep area for a future movie theater add flexibility and sophistication. The luxurious primary suite showcases a completely redesigned spa-inspired bath with whirlpool tub and oversized shower. Additional upgrades include all new Andersen windows, all new interior and exterior doors, and a brand new 30KW+ whole-house automatic generator system for peace of mind year-round. Outside, the property transforms into a private resort. Enjoy a newly built heated gunite pool with spa, expansive paver pool deck, outdoor kitchen, gazebo, basketball court, and playset. The walk-out finished basement opens directly to a beautiful paver patio, creating effortless indoor-outdoor flow ideal for entertaining. A 3-car garage and included pool table complete this extraordinary estate.

Spacious 3 BR, 2 Full Bath 1 partial single-family home sitting on a gorgeous 1.08-acre lot in Monroe! Relax at home in the light & bright sunroom or on the expansive back deck with cabanas and an above ground pool. Enjoy your hobbies in the heated out building space currently used as a workshop or turn it into a pool house. Offering 2,379 sq. ft. of versatile living space, this 1971 classic features a large light-filled living room with a feature fireplace. Great layout with generous bedroom sizes, a 2 car attached garage, and plenty of storage space. Extra outdoor storage is available in the two sheds. The 806 sq. ft finished lower level boasts a playroom with a bar & a second fire place, office and laundry room. Enjoy the peace and quiet of a sprawling, tree-lined lot while remaining just moments from local shopping, dining, and Blue Ribbon award-winning schools. A fantastic value with endless potential-move right in or bring your custom design updates to make it your own!

Every day feels like a vacation at this waterfront contemporary on Canoe Brook Lake. Tucked into one of Trumbull's most unique lake communities, this exceptional property offers the rare opportunity to enjoy peaceful, motor-free lake living with your own private dock, where mornings begin with coffee overlooking the water and afternoons are spent kayaking, canoeing, fishing, or simply relaxing in nature. Inside, soaring ceilings, a dramatic floor-to-ceiling stone fireplace, and an impressive wall of windows showcase breathtaking lake views while filling the home with natural light. Currently offering 3 bedrooms, 2 full baths, 2 half baths, and approximately 3,300 square feet, the flexible floor plan includes a desirable first-floor primary suite. The home's expansion potential makes it equally exciting for large gatherings or multi-generational living. Over 600 square feet of unfinished heated and air-conditioned second-floor space offers the opportunity for additional bedrooms and bath(s), while more than 1,200 square feet of unfinished walkout lower-level space provides endless possibilities for recreation, fitness, guest accommodations, or additional living area. Combined, the home has the potential to exceed 5,000 square feet. Additional features include a whole-house generator for added peace of mind. Whether you're searching for a year-round residence or the perfect weekend escape, this is a rare opportunity to own a truly one-of-a-kind waterfront home with incredible l

Welcome to 95 Pinto Lane in Monroe-a turnkey, custom-built luxury home set on 2 private acres in a quiet cul-de-sac within Hammertown Estates. Designed for those who work from home, commute to work, or enjoy a hybrid lifestyle, this residence offers both privacy and convenience with access to nearby train stations, I-95, and I-84, as well as highly regarded Blue Ribbon Schools, golf, and upscale dining. A dramatic 2-story foyer and sunlit breakfast area introduce an open, elegant layout ideal for everyday living and entertaining. The gourmet kitchen features a two-tier island, abundant cabinetry, and a butler's pantry/coffee bar, flowing into a two-story family room with fireplace. A private main-level office enhances work-from-home flexibility. Upstairs, 4 en-suite bedrooms include a luxurious primary suite with sitting area, spa-like bath, and dual vanities. The walk-out lower level offers a gym, recreation and billiards areas, and seamless access to a heated saltwater pool and outdoor entertaining spaces. Energy-efficient features include Hardie Board siding, propane heating, tankless water heater, and a whole-house generator. Additional highlights include 2 gas fireplaces, a built-in audio system extending outdoors, a 3-car garage, and a workshop-equipped shed. 95 Pinto Lane offers a rare combination of privacy, functionality, and lifestyle designed for modern living. Situated on a quiet cul-de-sac within Hammertown Estates, the property provides a peaceful setting while remaining accessible to major commuter routes and train lines serving New York City. The home features approximately 3,480 square feet of above-grade living space, complemented by an additional 900 square feet in a fully finished walk-out basement, offering ample room for entertainment, recreation, fitness, and storage. The layout is thoughtfully designed for both daily living and entertaining. Open-concept main living areas are complemented by defined spaces, including a private office and formal dining room. A built-in audio system extends throughout the interior and outdoor areas, enhancing everyday living and gatherings. Upstairs, the home offers 4 spacious bedrooms, each with its own en-suite bathroom, providing privacy and comfort. The primary suite serves as a luxurious retreat, featuring a gas fireplace shared between the sitting area and spa-like bathroom. Outdoor living is a central feature. The walk-out lower level opens to a covered seating area and a heated saltwater pool, creating a seamless extension of the home. The composite deck offers durability and low maintenance, while the two-acre lot provides usable space and natural privacy. The lower level includes dedicated areas for fitness, recreation, and leisure. Gym equipment, the billiards table, and the ping pong tabletop will remain, reinforcing the home's turnkey appeal. The property is designed with efficiency and reliability in mind, featuring propane heating, Hardie Board siding, a tankless water heater, water softener, whole-house generator, and sprinkler system. A security system with 6 cameras allows for remote monitoring. A large shed with electricity and a poured concrete floor offers extensive storage along with a fully functional workshop. The property offers access to highly regarded Blue Ribbon Schools, nearby golf courses, and upscale dining. This move-in-ready home combines comfort, efficiency, and lifestyle in a private yet connected setting.

Set back on a tranquil cul-de-sac enclave of prestigious Hubbell Mountain Farm North this 4 bedroom, 2.5 bath Custom Colonial offers the ultimate carefree lifestyle, blending modern elegance with vintage character. Situated on 9.24 level acres, the property boasts mature, colorful trees, sprawling stone walls, and an expansive composite deck with serene country views. Inside, an open floor plan features gleaming hardwood floors and an artistic flair throughout, French doors, and reproduction antique finishes. The heart of the home is the gourmet kitchen, complete with a center cherry top island, sun-drenched window seat, Viking stove, Sub Zero, and stainless appliances. It flows seamlessly into the elegant dining and family room area, highlighted by a custom, dual-sided smooth stone wood burning fireplace. A spacious living room, private home office, and powder room complete the main level. A spindle staircase leads upstairs to the primary sanctuary, featuring a walk-in closet and a luxurious marble bath with Edwardian-style console sinks and a soaking tub. Additional guest bedrooms offer generous closet space and ceiling fans, sharing a full bath that blends vintage architectural character with an airy aesthetic. A laundry room completes the upper level. Full walk-out lower level offers finishing potential and storage with 3 car garage. Equipped with a Generac generator. Just minutes to schools and Sherman Town Beach which is a town resident-only beach with pavilion.

Tucked at the end of one of Westport's most coveted cul-de-sacs, this 5-bedroom contemporary offers 6,310 sq ft of finished living space on just over a private acre, with a backyard path leading directly to Bedford Middle and Staples High School. From the foyer, a dramatic vaulted living room with skylights, built-ins and a floor-to-ceiling stone fireplace sets the tone. The glass-wrapped sunroom windows (newly replaced) frames stunning views of the lush grounds and heated gunite pool, while the updated eat-in kitchen with granite counters, center island, breakfast bar and pantry flows into a generous family room anchored by a second fireplace. A formal dining room and four main-level bedrooms offer flexibility, including possible first-floor in-law. Upstairs, the primary suite is a true retreat: vaulted ceilings, dressing room, walk-in closet and a private treehouse-like balcony overlooking the backyard. The expansive finished lower level delivers a playroom, game area and built-in wet bar, plus a large laundry room, mudroom and abundant storage. Recent updates include new natural gas heating and tankless hot water systems and new pool filtration. With a 2-car attached garage, walk-up floored attic and Westport beach rights, this is the rare home combining resort-style privacy with a walk-to-schools location - minutes to downtown, the train and Compo Beach.

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.

Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting. For the sportsman, pristine woodlands and abundant wildlife offer boundless opportunities for hunting, hiking, and connecting with nature. The residence-a nod to Antebellum architecture-presents grand columns, symmetrical facades, a 97-foot wraparound veranda, and ornate interior design. Every detail has been thoughtfully curated for comfort and quality. Your journey begins with the breathtaking grand foyer flanked by dual staircases and crowned by a soaring domed ceiling artfully decorated with colorful rosettes. Exemplary features include seven fireplaces, an elegant banquet-worthy formal dining room, a chef's kitchen with top-grade appliances, a spacious fireplaced breakfast room, a dazzling sun-filled family room, and two home offices. The exquisite primary suite is a luxurious haven featuring its own artfully adorned domed ceiling, sitting room, and wall-of-glass French doors open to a private balcony with views of the in-ground pool and woodlands. The sumptuous marble bath is a spa-like sanctuary. An invaluable addition to this amazing property is the finished studio over the six-car drive-through garage providing flexible living space. All this and so much more awaits in this extraordinary estate!

A rare opportunity to create your dream home on this .40-acre parcel ideally situated on a quiet cul-de-sac in a sought-after neighborhood. The property offers the ability to build a custom residence of just over 5,000 square feet and is being offered with full architectural plans and an approved demolition permit already in place, providing a streamlined path to construction. Residents enjoy access to the Millbrook Club grounds while benefiting from a location that offers both privacy and convenience, just moments from transportation, shopping, dining, and top-rated schools. Please note photos are conceptual renderings of what can potentially be built on the property based on the architectural plans.

This restored, 6,100 sf-expanded 18th century antique commands a view of its 1.24 ac, brook-fed lake; expansive lawn; raised beds; and 450 ft. bleached stone driveway. Your vision--Big Tented Celebrations,Fabulous Local Tomatoes--is correct. The former NYC chef's professional kitchen, wet bar, and 2 eat-in dining areas are open to the 5 rooms that circle around this heartbeat, making large gatherings feel and taste delicious. The antique's original entrance to a home office + fireplace (cozy, authentic) complete the floor. The 2nd floor offers 4 secondary beds/baths, a superior primary suite, and has a 600-sf bonus room with its own entrance and full kitchen. Generous third-level space fronted by a viewing balcony becomes the game/exercise/screening room you choose. Windows are featured everywhere, in particular note the sunroom array and the sitting room's 28ft of windowed walls. The separate 1,100 sf, 1-2 BR COTTAGE has had just 4 long-term tenants in the owners' 28 years. The COTTAGE rental income and tax/financial advantages make your net purchase price and occupancy exceedingly comfortable. The owner has prepared for final approvals a survey,building plans, and rendering package of a pool and surrounding deck connected to the home's 500sf front terrace. The buyer wishing the design can move forward with confidence in the sellers' careful efforts. A 2025, 95% efficient,state-of-the art, Navien natural gas boiler and HW installation has proven to be a gas bill slayer.

Welcome to the historic James Benedict House, one of Wilton's most notable and beautifully preserved 18th-century residences. This thoughtfully updated antique Colonial seamlessly blends timeless craftsmanship with modern convenience, offering 2,803 square feet across three full levels-including a true third floor with tall ceilings (not an attic)-plus a walk-out lower level ready to be finished. Set on an exceptional 4.81-acre property with a private pond, this rare offering provides unmatched privacy, scenic beauty, and the opportunity to create your own walking trails-all within one of South Wilton's most desirable locations. Property Highlights 4 Bedrooms | 2 Full Baths | 1 Half Bath 10 total rooms across three full levels True third floor with full ceiling height Walk-out lower level with finishing potential Central chimney with 5 fireplaces (3 gas, 2 wood-burning) Classic post-and-beam construction Refinished wide-plank hardwood floors Two staircases to the upper level Spacious eat-in kitchen Recent Upgrades & Enhancements Fully painted interior and exterior Updated bathrooms with modern finishes LED lighting throughout Brushed gold fixtures, hardware, and accents New backsplash Upgraded Decora-style switches and outlets (many with dimmers)

Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and thoughtfully updated for today's lifestyle, this inviting 4/5-bedroom, 3.5-bath residence offers nearly 3,000 square feet of living space set amidst picturesque grounds designed for year-round enjoyment. Inside, original architectural details and warm, welcoming spaces reflect the home's historic roots, while thoughtful updates provide modern convenience. Three renovated baths seamlessly combine classic style with contemporary finishes, while spacious living and entertaining areas offer flexibility for everyday living, gatherings with friends, and special occasions. Outdoor living is equally impressive. A spectacular solar-heated pool creates a private summer retreat, surrounded by mature landscaping and expansive grounds that enhance the property's peaceful setting. The barn is a standout feature, offering exceptional versatility with two-car garage parking, abundant storage, and exciting future potential for a finished second-floor loft, studio, office, gym, or guest space. Ideally located just minutes from the Cannondale train station for convenient access to New York City, as well as nearby shopping, dining, and local amenities, this special property offers the rare opportunity to enjoy the character and craftsmanship of a historic home while benefiting from updates that support modern living.

Located on Cranbury Drive in the highly sought-after Hillandale section of Trumbull. This expansive residence offers approximately 5,176 sq ft of living space on two main levels and is situated on a peaceful and private 2.38-acre lot. Blending scale, flexibility, and opportunity, this home features 4+ over sized bedrooms including two primary suites -one conveniently located on the main level and a second on the upper bedroom level, each with its own private en-suite bath, providing ideal separation for multi-generational living or guest privacy. In total, the residence includes 4+ bathrooms. A standout feature is the lower-level accessory apartment with a walk-out and private entrance, ideal for an in-law suite, au pair quarters, or extended guest accommodations. The home offers generous room sizes and a versatile layout suited to a wide range of lifestyles. The expansive, level rear yard provides a rare opportunity for outdoor enjoyment, entertaining, recreation, barbecues, and gatherings in a serene and private natural setting surrounded by mature landscaping. Many new improvements that also include a brand new septic tank (May 2026). Come experience why Trumbull is celebrated for its award-winning school system and why recently highlighted Trumbull, CT, as a top-tier housing market, ranking it on their "Hottest ZIP Codes" list due to high demand, a "family-focused" appeal, and strong commuter access. *Home is being sold as-is.

Welcome to your private oasis in prestigious North Stamford - a rare opportunity to purchase a beautifully maintained 10,000+ square foot estate nestled on a flat, landscaped 2-acre parcel. Offering 7 spacious bedrooms, 6 full bathrooms, and 2 half baths, this unique custom built in contemporary ranch impresses with soaring vaulted ceilings, high ceilings throughout, a first-floor en-suite, multiple living areas, and endless flexibility for multigenerational living or extended guests. From the moment you enter, you are greeted with space, elegance, and functionality. This home features two separate areas ideal for in-law suites or au pair quarters, making it perfect for larger families or households seeking privacy and independence under one roof. The thoughtfully designed layout includes generous formal and informal living areas. The home's size and flow make it truly exceptional for hosting - from intimate gatherings to larger events. Step outside to your expansive raised stone patio, surrounded by a beautifully manicured yard offering plenty of room for recreation, play, or relaxation in a peaceful, park-like setting. This is a rare chance to enjoy the scale and serenity of a true estate while remaining minutes from downtown Stamford, premier schools, shops, and commuter routes.