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$4,999,000
5 Beds ⋅ 9 Baths ⋅ 24146882 MLS
A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

294 Maple Rd, Easton
$4,995,700
4 Beds ⋅ 5 Baths ⋅ 24176377 MLS
Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage and specs can vary, but the standard of excellence does not. Coastal Luxury Homes is the premier Fairfield County bespoke builder.

22 Dawn Dr, Westport
$4,995,000
5 Beds ⋅ 5 Baths ⋅ 24195094 MLS
1716 Shippan Avenue represents a rare opportunity to own a legacy estate on 1.01 acres in Stamford's sought-after Shippan neighborhood. This distinguished Tudor home is comprised of approximately 6,000 square feet of timeless architectural character, sophisticated modern updates, and a thoughtfully designed 2016 renovation by Granoff Architects. With 5 bedrooms, 3 full and 2 half baths, the home is rich in detail, including original stained glass, oak paneling, unique solid oak arched interior doors, and three wood-burning fireplaces. Custom millwork, a Vermont slate roof, and new Marvin windows throughout further showcase the home's exceptional craftsmanship. The beautifully updated second-floor bathrooms feature custom cabinetry, bookmatched marble showers and countertops, and heated floors. In addition to generous living and entertaining spaces, the home also includes a finished lower level, a third-floor loft with water views (currently used as a home gym), and a charming attached greenhouse. Outside, a 40' x 20' gunite pool and spa, expansive patio, and mature gardenscape create a picturesque private oasis. Exceptionally private, the expansive grounds made up of 2 parcels provide an idyllic backdrop for sun-filled summer days, evenings spent poolside, and memorable gatherings with family and friends. Enjoy Shippan's waterfront community minutes away from the Stamford Yacht Club, local dining, and the express train to Manhattan.

1716 Shippan Ave, Stamford
$4,995,000
3 Beds ⋅ 4 Baths ⋅ 24194201 MLS
The dream of waterfront living is officially taking shape-construction is underway by renowned builder The O'Dell Group. This is your chance to secure a front-row seat to the Long Island Sound on one of Westport's most prestigious stretches of coastline. This exceptional property offers direct water frontage + sweeping, uninterrupted views of the Sound + the iconic Old Mill Beach. Imagine waking up to the soft glow of a sunrise over the water, spending your afternoons enjoying the refreshing salt air, or relaxing to the rhythm of the tide. Every detail of this build is designed to maximize the connection to the sea, offering a lifestyle defined by beauty + tranquility. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools + Westport's vibrant downtown, known for its exceptional dining, shopping, and cultural experiences. Plus, the location is ideal for commuters, with close proximity to Metro-North for a seamless trip to Grand Central Station in NYC. As the last available parcel of its kind for development in this coveted location, this project represents a rare opportunity to own a brand-new architectural masterpiece in an idyllic setting. With The O'Dell Group's signature craftsmanship now in motion, the vision for this ultimate beach house is becoming a reality. Seize the opportunity to claim this piece of paradise and personalize your finishing touches while there is still time. Reach out today to make this coastal sanctuary your own.

238 Hillspoint Rd, Westport
$4,995,000
4 Beds ⋅ 5 Baths ⋅ 24172306 MLS
A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area's most coveted waterfront settings. Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape. Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline. A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic's acclaimed restaurants, boutiques, marinas and waterfront attractions.

39 Chippechaug Trl, Stonington
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 24126503 MLS
Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous garages, balconies, patios and covered porches, will be designed in collaboration with the homeowner - ensuring every detail reflects your vision. Expansive layouts, pool sites, and inviting outdoor living spaces create the perfect setting for today's lifestyle, balancing sophistication with everyday comforts. Working with Coastal Luxury Homes is a dynamic, collaborative and easeful process with every detail curated to suit the homeowners' vision of the perfect home. Whether you dream of having your own golf simulator, outdoor chef's kitchen, sauna or elevator...everything is possible. Ideally located just moments from Westport's award-winning schools, vibrant downtown, the train, and Compo Beach, this unique neighborhood offers a rare combination of privacy and convenience. Mature landscaping and thoughtful design create a serene retreat, while the best of dining, shopping, and recreation are just minutes away. This is more than a new home - it's the chance to create your dream residence with an award-winning builder in a community unlike any other in Westport.

1 Coastal Ct, Westport
$4,950,000
6 Beds ⋅ 7 Baths ⋅ 24173339 MLS
Hidden behind Shorehaven Country Club in a gated waterfront enclave, 3 Canfield Crossing offers the rare opportunity to enjoy WATERFRONT LIVING in a NATURALLY PROTECTED WATERFRONT SETTING. Thoughtfully reimagined and extensively updated, the property combines timeless coastal design with the peace of mind of significant recent improvements, including a BRAND NEW CEDAR ROOF, new windows, several new mechanical systems, a new pool heater, and an entirely new chef's kitchen with custom cabinetry and premium appliances. Designed to embrace its waterfront setting, nearly every room captures views of the ever-changing tides. A NanaWall opens the newly renovated kitchen and living areas directly to the expansive waterfront terrace and infinity-edge pool, creating an effortless connection between indoors and out. With four finished levels connected by elevator, six ensuite bedrooms, including two separate guest or au pair opportunities, the home offers exceptional flexibility for everyday living and entertaining. Kayak or paddle board directly from your backyard, spend an afternoon at nearby Shorehaven Country Club, or enjoy the restaurants and amenities of Westport, Rowayton, and South Norwalk just minutes away. Private, protected, extensively updated, and directly on the water, 3 Canfield Crossing delivers a distinctive Fairfield County waterfront lifestyle without sacrificing the comfort, space, and convenience of a substantial year-round residence.

3 Canfield Xing, Norwalk
$4,850,000
4 Beds ⋅ 5 Baths ⋅ 24176398 MLS
"Hollow Farm" - An Expansive Historic Estate Reimagined for Modern Country Living Nestled in its own private valley, this 72-acre estate includes a Main House, thoughtfully updated and expanded in 2005; a charming Guest Bungalow; screened Gazebo perched over a pond; Pool Pavilion; Stables with caretaker's apartment; and a restored Barn. Comprised of multiple parcels, offering maximum privacy. The circa-1755 Main House features a dramatic great room with stone fireplace, adjoining chef's kitchen, and formal dining room. Additional main-level spaces include both a sitting room and a library with back-to-back fireplaces, plus a guest suite with full bath and sitting room. Upstairs, the primary suite offers a lofted sitting area with fireplace, as well as private deck, while two guest bedrooms share a hall bath. The lower level includes a wine cellar with cobbled floor and a gym. Outside, multi-level terraces showcase exceptional stonework, a fire pit, grilling area, pool, and spa. Two ponds and the sparkling Merryall Brook enhance the 18 acres of open land. Extensive landscaping compliments the natural beauty of the forested hills. As with the Main House, every outbuilding and outdoor space has been meticulously maintained. Although it feels a world away, this remarkable property is only 15 minutes from Kent, New Preston, and Washington. With its historic character, modern updates and expansive private setting Hollow Farm offers a rare opportunity for refined country living

57 Indian Trail Rd, New Milford
$4,850,000
5 Beds ⋅ 5 Baths ⋅ 24172211 MLS
Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport
$4,750,000
5 Beds ⋅ 7 Baths ⋅ 24204438 MLS
A fresh take on Modern Luxury awaits at this new construction home set on stunning property in the Old Hill area of Westport. Now complete and ready for immediate enjoyment, this dynamic residence is perfectly located for convenience to commuting, the train station, schools, shopping and more. Exhilarating architecture will awaken your senses as you approach this customquality home. Walls of glass blend the natural setting with stunning interiors, and bring sunlight deep into the spectacular rooms. The chef's kitchen is a showpiece, featuring bespoke oak cabinetry, premium finishes, and a substantial walkin pantry. Dual mainlevel offices support today's lifestyle. 5 spacious bedrooms and 7 refined baths create a harmonious balance of comfort and sophistication. The primary suite is a serene retreat with three fitted closets and a spalevel ambiance. Additional bedrooms offer generous scale and thoughtful design. A sunlit upstairs lounge and a finished thirdfloor space provide flexible areas for work, play, or creativity. The finished lower level offers exceptional spaces for fitness, media, or entertaining. Outside, an expansive patio overlooks 1.68 acres of private grounds, ideal for gatherings or quiet reflection. A 3car garage (with a separate bay for a trophy vehicle or storage) and sleek modern detailing complete this remarkable offering. An inspired blend of architecture, setting, and convenience await in a prime location. Pool permit in place.

1 Twin Oaks Ln, Westport
$4,750,000
4 Beds ⋅ 3 Baths ⋅ 24196499 MLS
Rare opportunity to experience waterfront living at its finest. Perfectly positioned on the picturesque Five Mile River with 240 feet of direct water frontage, this exceptional shingle-style residence offers panoramic water views, an all-tide dock, & direct access to Long Island Sound for boating, paddleboarding, kayaking, fishing, and waterfront entertaining. Designed to embrace its setting, the turnkey 4-bedroom, 3-bath home features a light-filled floor plan with vaulted ceilings, a chef's kitchen appointed with a new Sub-Zero refrigerator, Wolf oven, and gas cooktop, and seamless indoor-outdoor living extending to a private, enclosed waterfront yard, perfect for entertaining or enjoying sunrises over the harbor. Equipped with a full-house generator, underground irrigation, and abundant storage. Ideally located within walking distance of Rowayton Village, Metro-North, and the scenic roads of Tokeneke, this exceptional home offers the best of Fairfield County's coastal lifestyle. Spend your days enjoying Darien's beaches, charming cafes, boutique shops, and local restaurants, while taking advantage of a direct commute to Manhattan, less than an hour away. Combining an all-tide dock, expansive water frontage, and unparalleled access to both nature and amenities, this is a rare offering in one of Fairfield County's most coveted coastal communities. The listing agent can secure your private appointment. Available to move in immediately (before closing).

61 Five Mile River Rd, Darien
$4,750,000
4 Beds ⋅ 6 Baths ⋅ 24193947 MLS
Ultra private hilltop estate with panoramic views overlooking Lake Waramaug with steps to private waterfrontage & floating dock. Chic 4 bedroom, 4 full and 2 half bathroom shingle-style house with infinity edge swimming pool & spa with magnificent views overlooking the lake. Formal entrance foyer leads to Great Room-style chefs eat-in Kitchen / Dining / Family room, with French doors to wrap around porch overlooking the lake. Library with fireplace. Up the beautiful double-height staircase is the luxe Primary Suite with fireplace, dressing room, and full bath with double-size steam shower, dual vanities & deep soaking tub in front of a wall of windows facing the lake. Three more bedrooms with lake views are on this level -- one en-suite and the other two share a Jack-and-Jill bath. The fully finished walk-out lower-level includes a media / game room with kitchenette, laundry & full bath with shower and leads to large stone patio and pool. 3-car detached garage with potential in-law / guest apartment. Fully fenced property. Outdoor fieldstone fireplace. Must see. Rare.

90 Tinker Hill Rd, Washington
$4,750,000
4 Baths ⋅ 24194611 MLS
+/- 37,769 SF two-story building on a well-manicured 5.12-acre campus. The building is in superb condition. It is currently operated as a school. Its numerous features include classrooms and offices throughout, a 2,500-lb. capacity Otis passenger 2-stop elevator, gymnasium with full basketball court and stage area, heavy power, and sprinkler system. Exterior access to the ground level and sizable, finished lower level. Located in a quiet neighborhood near the intersection of Routes 22 and 17. The building is within easy walking distance to the center of Northford retail/business district. Only 5 miles to I-91 and Rt. 5 (Washington Avenue) in North Haven, and 6 miles to the Wilbur Cross Parkway. In addition to its use as an educational facility this property's potential purposes may include retail, office, church, and others.

26 Old Post Rd, North Branford
$4,750,000
7 Beds ⋅ 8 Baths ⋅ 24181755 MLS
Tucked away on a quiet cul-de-sac on the western shore of the Mystic River stands an exquisite 5,926 sq. ft. Georgian Colonial. As you view this 1931 estate and learn the unrepeatable details of its magnificent construction, this stately residence confirms it was built for this waterfront location, not just placed on it. Built to endure direct waterfront exposure with construction standards that have proven their value since 1931. Over the past 23 years, the owner has made many upgrades: Electrical, Heating, Lighting, Commercial Alarm system, Window Well Drainage System, Seawall, Roof w/ice shield, & more. All this to safeguard the home while bringing a lighter flair and more contemporary feel to the interior without sacrificing its elegance.* The sequence of spaces tells it all. Water-facing windows carry the shoreline through the principal rooms, so the setting follows you. Arched openings keep sightlines long; French doors dissolve the boundary between living space and covered porch, so indoor and outdoor rooms work as one floor plan. Coffered ceiling detail, Built-in cabinetry, and a centered fireplace give the interior the same permanence as the brick and stone outside. Hardwood floors run throughout. Formal dining and generous living areas hold a crowd; The bedrooms hold the quiet with soft light, water views, & the primary, with a private balcony. The spacious kitchen with water views & direct access draws you to the backyard:Terrace, Pier, Beach, the Sunrise or Sunset

30 Essex St, Groton
$4,700,000
6 Beds ⋅ 6 Baths ⋅ 24176873 MLS
IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with exceptional trim work and french doors leading to an outdoor covered porch and inviting blue stone patio. Expansive family room with welcoming fireplace and grand living room with a second fireplace for festive family celebrations. Chef's kitchen with custom cabinetry and top of the line appliances offers a separate eating area with bay windows. Bedrooms are generously sized with full marble baths and top quality vanities. Opulent master suite provides a perfect place to retreat. The finished third floor with additional living space will surely suits your family and Lifestyle. Two extra generously sized bedrooms, a full bath, room for a movie theater, a playroom or gym complete this unique oversized beach sanctuary. OPTIONS available: Sauna, Elevator, Wine parlor, Outdoor loggia and Pool. LAND OF 0.31 ACRE IS RARE and OVERSIZED. A TRUE GEM. Please note that is project is a proposed built and that the pictures depicted here are from local and renowned builder NewGenerationHealthyHomes. Inquire today to view or request builder's extensive portfolio and finishes

394 Penfield Rd, Fairfield
$4,700,000
5 Beds ⋅ 7 Baths ⋅ 24161583 MLS
Set on over four and a half acres of private, level grounds in one of New Canaan's most sought after locations, this exceptional estate offers a rare combination of scale, privacy, and close to town convenience. Originally built in 1962 and thoughtfully expanded, the property unfolds as a true compound. The main residence features five bedrooms, seven baths, and beautifully proportioned living spaces anchored by three fireplaces. A seamless connection between the chef's kitchen and family room creates the heart of the home, designed for both everyday living and effortless entertaining. The kitchen is fully equipped with a six burner Wolf gas range, second Wolf oven, Miele dishwasher, Sub Zero refrigerator and freezer, wine cooler, beverage drawers, marble island, and double sinks. Beyond the main residence, the estate continues to impress. A separate antique guest house with full kitchen, 3 bedroom and 1-1/2 bath provides ideal accommodations for extended family or guests. The heated gunite pool and pool house, added in 1991, offer a true retreat setting, complete with a party room, kitchen, bedroom, bath, and sauna for a resort like experience. A rare opportunity to own a private New Canaan estate with exceptional grounds, flexibility of living, and proximity to town.

537 Oenoke Rdg, New Canaan
$4,699,000
24188138 MLS
Opportunities like this do not come often. This well-appointed Brick/Venier building features 72,000 sq. ft. school zoned property sitting on 2.84 AC of prime real estate. Property consists of classrooms, cafeteria & kitchen, along with gym facilities. Plenty of frontage both on Maple St. for the main entrance with on street parking along with a large parking lot off Rt. 44 for the rear entrances. Many recent upgrades including sprinkler system, roof replacing, electrical update, heating updates and more. Great opportunity for investment as the owner would like to rent back at a fair/market rate with a long-term commitment.

18 Maple St, Putnam
$4,650,000
4 Beds ⋅ 5 Baths ⋅ 24176753 MLS
Welcome to 150 Joshuatown Road in Lyme, a stunning, custom built residence sited on over 30 acres of bucolic land, with specimen trees, beautiful landscaping, and over 1/4 mile of impressive rebuilt stone walls. The main level features a welcoming foyer, Chef's kitchen with breakfast room, a cherry paneled library with vaulted ceiling and warming fireplace, commodious dining room, living room with separate seating areas, and a first floor primary suite. The second level has additional bedrooms and a beautiful family room, currently used as an art studio. In addition to the Main house, there is an incredible Guest house, fully functioning with full kitchen and adequate bedroom space. This is a property that needs to be seen to be believed! Simply amazing!

150 Joshuatown Rd, Lyme
$4,650,000
24177556 MLS
469 East Main Street, Branford, Connecticut, is offered for sale as a stabilized multi-tenant investment property anchored by Planet Fitness, which has approximately eight years remaining on its current lease term along with multiple renewal options. The property provides stable and predictable long-term cash flow and is offered at an approximate 7.5% capitalization rate and roughly $165 per square foot, presenting an attractive investment opportunity within the Connecticut market. The 28,088-square-foot freestanding retail building features a complementary mix of synergistic tenants and is strategically positioned along a high-visibility commercial corridor between New York City and Boston. Its proximity to Yale University and Yale New Haven Hospital further supports strong regional demand and long-term market stability. This offering represents an opportunity to acquire a well-maintained, turn-key investment asset with secure income, long-term tenancy, and favorable positioning within a strong Connecticut retail market.

469 E Main St, Branford
$4,625,000
3 Beds ⋅ 3 Baths ⋅ 24180859 MLS
Welcome to Little Pond Farm in Stonington, CT. This private estate of 96 acres on the Connecticut shoreline is midway between Boston and New York and minutes from ocean beaches, sailing, and the historic village of Mystic. It offers the space and privacy of true country living within easy reach of the coast. The custom main residence pairs scale with warmth: a great room anchored by reclaimed antique beams, wide-plank floors, and a stone fireplace opens to a chef's kitchen and a custom wood island, all framing views across fields, ponds, paddocks, and the post-and-beam barn. The main-level primary suite offers dual closets, an en-suite with an oversized walk-in shower, and a private stone terrace with an oversized gunite hot tub & outdoor shower. A fireside library, screened porch, and service rooms complete the floor; two additional bedrooms with a jack and jill bathroom are located on the upper level.The barn is fitted with four oversized stalls, tack and feed rooms, and a wash stall, connected by breezeway to a two-level guest house. The ground level offers a large studio with a wet bar, half bath, and an attached one-car garage; above is a complete guest residence with a full kitchen and living area, bedroom, walk-in closet, and full bath. 70 of 96 acres are permanently protected under a Connecticut Farmland Trust easement, permitting agricultural use and structures preserving the surrounding hayfields, woodlands, and brook in perpetuity and ensuring lasting privacy.

305 Pequot Trl, Stonington
$4,600,000
6 Beds ⋅ 8 Baths ⋅ 24204809 MLS
Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

2 Windy Hill Rd, Westport
$4,595,000
6 Beds ⋅ 7 Baths ⋅ 24203624 MLS
A remarkable home where historic charm has been completely reimagined for modern living, set on over two acres in one of New Canaan's most coveted locations. Impeccably cared for and thoughtfully updated throughout, this stately residence offers over 7,000 square feet of beautifully appointed interiors with six bedrooms, six-and-a-half bathrooms, custom millwork and moldings, soaring ceilings, and exceptional attention to detail. A welcoming entry and adjoining office open to an elegant living room with double-sided gas fireplace and formal dining room with butler's pantry. Designed equally for effortless entertaining and everyday living, the heart of the home is an extraordinary custom kitchen with ample storage opening to an impressive, light-filled family room. Multiple French doors extend the living spaces outdoors to the rear porches, sweeping lawns, and pool. A powder room, two bedrooms, full bath, and mudroom provide added flexibility on the main level. Upstairs, the luxurious primary suite is a true retreat with fireplace, balcony, spa-like bath, and three walk-in closets. Three additional bedrooms, three bathrooms, a second family room, and laundry room complete the second level. The lower level offers additional living space with a bonus room, access to the three-car garage, and a fabulous cabana room with wet bar, updated full bath, and sliding doors opening directly to the pool for effortless summer entertaining.

125 West Rd, New Canaan
$4,500,000
5 Beds ⋅ 6 Baths ⋅ 24204371 MLS
Your own private oasis in a prime Midcountry location. 739 Lake Avenue blends peaceful private living with easy access to downtown and all that Greenwich has to offer. The classic colonial is set back on 2.3 acres. Inside, the layout flows effortlessly from room to room, ideal for both everyday living and entertaining. Five oversized bedrooms and five and a half baths provide comfortable, flexible space for the whole family, and every detail reflects timeless colonial charm paired with thoughtful livability. A home that has been meticulously cared for throughout the years while keeping gorgeous charm from moldings to archways. Step outside to your own private oasis: a sparkling pool and beautifully landscaped backyard made for long summer days, weekend gatherings, and quiet evenings at home. A cabana bath attached to the house makes pool days effortless, no tracking water through the home required. Just 10 minutes from downtown Greenwich, you get the best of both worlds: peaceful, private living with easy access to town, shops, restaurants, and the train. A rare find, and a true classic Greenwich home.

739 Lake Ave, Greenwich
$4,500,000
5 Beds ⋅ 6 Baths ⋅ 24202628 MLS
A Greenwich classic, this distinguished five-bedroom residence combines timeless architecture, exceptional craftsmanship, and grand-scale rooms designed for both entertaining and everyday living. Perched high above sweeping, beautifully landscaped grounds, the home enjoys a commanding setting with privacy, mature plantings, and expansive westerly views across the property. A slate roof, custom millwork, multiple fireplaces, and graciously proportioned interiors further reflect the home's enduring character. Elegant formal living and dining rooms are complemented by a Christopher Peacock kitchen with adjoining breakfast room, a comfortable family room, and a library or private office. Upstairs, the spacious primary suite is joined by three additional bedrooms, two of which are en suite. A fifth bedroom and flexible living space on the lower level provide additional accommodations. Expansive terraces extend the living spaces outdoors, overlooking the sweeping grounds and putting green, while a circular drive creates an impressive approach. A rare combination of scale, privacy, and setting, just minutes from central Greenwich.

74 Glenville Rd, Greenwich
$4,500,000
4 Beds ⋅ 4 Baths ⋅ 24199141 MLS
The Gold Coast meets the Connecticut shoreline in this extraordinary Wilson Point estate, gracefully perched to capture water views stretching to Long Island Sound. Built in 1924, this English Tudor Manor-style residence is one of the original homes in the coveted Wilson Point Association, offering timeless architecture, rich character, and an exceptional sense of history. The home features four/five bedrooms, four full baths, sun-filled living spaces where nearly every window frames picturesque views of the surrounding landscape, an office, and bonus spaces. A charming fenced kitchen garden and an enclosed vegetable garden awaits the gardener and chef alike. Just steps from the private beach, clubhouse, and tennis courts, this spectacular property offers multiple terraces for entertaining, perennial gardens, and an expansive lawn, creating an idyllic setting for relaxing, gathering with family and friends, and enjoying the best of Connecticut coastal living. A prime location for an easy commute to NYC - just 47 minutes to Grand Central from Rowayton - the closest train station and a 3-minute drive. Wilson Point provides the ultimate privacy along with dock, and boat mooring options.

1 Woodland Rd, Norwalk
$4,500,000
5 Beds ⋅ 4 Baths ⋅ 24200980 MLS
TOES IN THE SAND & SUMMER EVERY DAY. There are waterfront homes-& then there are homes where the water becomes part of everyday life. Welcome to 1149 Fairfield Beach Road, a truly special direct beachfront home appprox 60+/- min from NYC. Thoughtfully designed by a builder for his own family, with an emphasis on capturing the extraordinary waterfront setting. Walls of windows fill the open living spaces w natural light and capture spectacular water views. Directly outside main-level family room w/no steps to the patio, is your own beach. Three of 4 waterfront bedrooms open to a wraparound deck, giving each its own connection to the water while creating private spaces. Wake to sun-filled rooms & end the day to the sound of waves. An impressive Great Room @ the mezzanine level is an inspiring addn'l gathering space that features 12' ceilings w skylights. Kitchen, bathrooms & laundry room updated in 2025. Rare garaged & off street parking for 10 Cars! An unfinished 3rd floor w private balcony offers potential for future 1,000+/- additional SF. Also Includes: Private STUDIO APARTMENT updated(2022) & awesome! Perfect for guests/extended family/home office or summer overflow just a couple of steps over @1148. Mins. to Schools, TOWN & TRAIN! ENJOY DIRECT BEACHFRONT living while being minutes from Downtown Fairfield, popular farmers market, outdoor & indoor concerts, restaurants w/ great outdoor seating, shoppes, movies, town events & the best of what Fairfield has to offer

1149 Fairfield Beach Rd, Fairfield
$4,500,000
5 Beds ⋅ 4 Baths ⋅ 24200828 MLS
TOES IN THE SAND & SUMMER EVERY DAY. There are waterfront homes-& then there are homes where the water becomes part of everyday life. Welcome to 1149 Fairfield Beach Road, a truly special direct beachfront home appprox 60+/- min from NYC. Thoughtfully designed by a builder for his own family, with an emphasis on capturing the extraordinary waterfront setting. Walls of windows fill the open living spaces w natural light and capture spectacular water views. Directly outside main-level family room w/no steps to the patio, is your own beach. Three of 4 waterfront bedrooms open to a wraparound deck, giving each its own connection to the water while creating private spaces. Wake to sun-filled rooms & end the day to the sound of waves. An impressive Great Room @ the mezzanine level is an inspiring addn'l gathering space that features 12' ceilings w skylights. Kitchen, bathrooms & laundry room updated in 2025. Rare garaged & off street parking for 10 Cars! An unfinished 3rd floor w private balcony offers potential for future 1,000+/- additional SF. Also Includes: Private STUDIO APARTMENT updated(2022) & awesome! Perfect for guests/extended family/home office or summer overflow just a couple of steps over @1148. Mins. to Schools, TOWN & TRAIN! ENJOY DIRECT BEACHFRONT living while being minutes from Downtown Fairfield, popular farmers market, outdoor & indoor concerts, restaurants w/ great outdoor seating, shoppes, movies, town events & the best of what Fairfield has to offer

1149 & 1148 Fairfield Beach Rd, Fairfield
$4,500,000
24184895 MLS
Located in the desirable coastal town of East Lyme, 223 North Bride Brook Road offers a rare opportunity to acquire approximately 78 contiguous acres of undeveloped land. Formerly a working dairy farm, this expansive parcel features a blend of level, open fields and lightly wooded areas, combining rural privacy with coastal convenience. Positioned just minutes from the shoreline, this substantial acreage stands as one of the premier land offerings currently available in southeastern Connecticut. The scale and versatile topography of this RU-40 zoned parcel support a variety of potential uses. For developers and builders, the property's level layout is well-suited for a thoughtfully planned residential neighborhood or a subdivision of custom homes. Since the parcel is large enough to qualify for Special Permit uses under the town's Zoning Regulations, the acreage provides an ideal canvas for a private family compound, a substantial country estate, a golf course, vineyard or equestrian and agricultural pursuits that honor the land's heritage. It also represents a significant long-term investment and land-banking opportunity in a high-demand market. While private and quiet, the property offers excellent accessibility. It is located just five minutes from Interstate 95, downtown Niantic, local beaches, schools, and shopping. This balance of rural tranquility and daily convenience makes the parcel a unique find.

223 N Bride Brook Rd, East Lyme
$4,500,000
4 Baths ⋅ 24182009 MLS
Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.

423 Main St, Middletown
$4,500,000
3 Beds ⋅ 6 Baths ⋅ 24180925 MLS
Set across 53 gated acres in Northern Fairfield County, this exceptional estate offers a rare combination of privacy, scale, and natural beauty, just minutes from Ridgefield, approximately 10 minutes from Danbury Airport, and within practical reach of New York City. Originally conceived as a country retreat, the property blends historic character with modern comfort in a setting that feels private and serene, yet fully suited to year-round living. Beyond the gates, the grounds unfold across woodland trails, a stone bridge, pond, brook, orchards, gardens, and approximately two miles of groomed paths through the estate's own natural preserve. The landscape has been carefully maintained and offers both beauty and utility, with room for recreation, agriculture, and future enhancements. The residence is rich in character and thoughtfully updated, with six fireplaces, a double-sided chef's kitchen, wine cellar, and a 1,055 SF primary suite with dual baths, dressing room, walk-in closet, private sitting room, and sunroom. Outdoor living is centered around a heated gunite pool, outdoor kitchen, pergola, and gazebo, all positioned to take in sweeping views of the surrounding landscape. A detached barn, detached garage, and expansive acreage create unusual flexibility for equestrian pursuits, agriculture, a guest house, tennis or paddle court, and other future improvements, subject to local approvals.

155 Long Ridge Rd, Danbury

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