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$3,950,000
8 Beds ⋅ 10 Baths ⋅ 24100203 MLS
Come see this remarkably private property a stone's throw from the center of Litchfield. This stately home was built in 1992 and boasts over 10,000 s/f of finished space. The grounds are professionally landscaped and have a beautiful patio, pool and greenhouse. There are 8 bedrooms and 13 bathrooms along with a powder room . The sunny , modern, large eat-in kitchen open onto a patio, which then leads to the saltwater pool. A main floor guest bedroom suite with its own bathroom is an added convenience and can be a ground floor primary. There are lots of space for grand entertaining in the formal dining room, living room and great room. Plenty of cabinetry and shelves to display your treasures. You can warm yourself by the fireplaces. The master bedroom suite on the upper level has it all, walking closet, fireplace , sunroom and a large bathroom with steam shower and jet tub. 3 additional bedrooms round up the second floor, all with en-suite bathrooms. A separate laundry room is conveniently located on the bedroom level. The 3 floor has a loft and 2 additional bedrooms also with en-suite bathrooms.The lower level is fully finished and is a walk-out to the grounds. It also includes a wine cellar, a gym and a kitchenette. A separate apartement with a patio is located above one of the garage, which house 3 cars. Another garage for 6 cars is an additional outbuilding. Acreage is consisting of 3 separate parcels which are included w/sale.

184 Fern Ave, Litchfield
$3,900,000
5 Beds ⋅ 6 Baths ⋅ 24189523 MLS
Set on 2.19 private acres in a prime Darien location, 222 Brookside Road offers exceptional space, privacy, and opportunity just minutes from town and Cherry Lawn Park. With more than 7,000 square feet above grade, plus an additional 3,000 square feet on the lower level, this expansive 4-bedroom, 5.5-bath residence provides an incredible canvas to create a home tailored to your vision. Generously proportioned rooms and tall ceilings create a wonderful sense of scale throughout, while a flexible floor plan offers endless possibilities, including the potential for a first-floor in-law or guest suite. The exceptionally spacious lower level provides abundant room for entertaining, relaxing, and recreation. Outdoors, the expansive property is highlighted by a pool and well-appointed pool house featuring a full bath, laundry hookups, and full kitchen with a range and space for a refrigerator-creating a private setting for summer gatherings and relaxation. An attached four-car garage, plus an additional detached two-car garage, provides parking for six cars and even more flexibility. A rare opportunity to enjoy significant acreage, remarkable space, and endless potential in an incredibly convenient Darien location.

222 Brookside Rd, Darien
$3,900,000
3 Beds ⋅ 3 Baths ⋅ 24169897 MLS
Overlooking the hills of Lyme, Connecticut, Hilltop Estate combines old world elegance with modern luxury. The fully renovated stone and stucco main house, spacious guest cottage, pool and barn complex are set on nearly 50 acres. Made up of five separate parcels with potential for equestrian pursuits, farm to table living or sellable individually. The barns include a workshop fully convertible to living space, artist studio or entertainment space. Contiguous to the barns is an Alitex greenhouse manufactured in England with its own dedicated, fully equipped potting room. The property is surrounded by manicured gardens, stone walls, privet hedges and mature plantings. The three bedroom, two and one half bath main house exudes historic character with detailed moldings, refined finishes, antique chestnut floors, custom built-in cabinetry, grass cloth wallpaper, hand-hewn exposed beams, multiple fireplaces, decorative painting and light-filled interiors. The gourmet kitchen features two stoves (Wolf and Gaggeneau) and a Sub-Zero refrigerator. Enjoy the outdoor terrace for six months a year; warmed by its stone fireplace and protected by fully retractable roller screens in the summer. The two bedroom en-suite guest cottage complete with a full kitchen provides a luxurious escape for family and friends. Meandering trails throughout the property provide a peaceful hiking experience for enjoyment year-round. The property is equidistant to New York City and Boston.

213 Beaver Brook Rd, Lyme
$3,900,000
4 Beds ⋅ 3 Baths ⋅ 24163908 MLS
Welcome to 23 and 24 Echo Drive, New Milford, CT-a timeless gem first introduced to the market by the family who originally built it. Nestled on the shores of Candlewood Lake within the prestigious Birch Groves community, this exquisite residence embodies the classic Adirondack style of the 1930s with its captivating stone and wood construction. Spanning 2,073 square feet, this elegant lake home offers four spacious bedrooms, a three season porch and a storybook living room with an impressive floor to ceiling field stone fireplace, providing ample space for relaxation and entertainment. With western exposure, enjoy breathtaking sunset views from the comfort of your home that seamlessly blend indoor and outdoor living. Lakeside, this home offers a wide expanse of private waterfront over two lots that looks out onto protected land with no homes, a private dock, and a hard to replicate lake side boat garage/shed. Included in this rare offering is 24 Echo, a lot, presenting endless possibilities for expansion of the family compound or a private retreat. Experience the charm of lakeside living with the convenience of modern amenities. This unique opportunity awaits you to create lasting memories in a home that effortlessly blends vintage charm with contemporary elegance. Make this unique and distinguished property yours today. 23 Echo is located on the western (waterfront) side of Echo Drive (0.63 Acres) and 24 Echo is located on the east side of Echo Dr (0.43 Acres)

23 Echo Dr, New Milford
$3,895,000
6 Beds ⋅ 6 Baths ⋅ 24162168 MLS
Luxury new construction opportunity in Lower Weston! Currently slated for completion in less than a year, this meticulously crafted estate offers a rare opportunity to secure your forever home on a private Lower Weston cul-de-sac. Take advantage of your opportunity to live in the most convenient Weston location within minutes of their top rated schools and town center. Plus enjoy the convenience to downtown Westport's shopping, dining, and beaches- as well as easy commuting to NYC. This impeccable design by the Tomas Brothers Builders redefines luxury with their electrical and landscaping expertise. Set on a lush 2-acre oasis that includes a high-end pool, the home offers a resort-style retreat right in your backyard. A masterfully planned sanctuary.

8 Norfield Woods Rd, Weston
$3,890,000
4 Beds ⋅ 4 Baths ⋅ 24148103 MLS
Set on its very own private isle, this extraordinary 4-bedroom, 3.5-bathroom retreat redefines luxury coastal living. Enjoy unmatched privacy and serenity, all just a five-minute boat ride from the idlyllic Stony Creek mainland-a rare balance of peaceful island living with effortless convenience and peace of mind. Family and guests will appreciate the added benefit of a seasonal water taxi, operating hourly in the summertime, ensuring smooth and enjoyable arrivals and departures. Sunlit interiors showcase sweeping, unobstructed water views from nearly every room, while gentle sea breezes drift through a harmonious blend of indoor and outdoor spaces. Elegant living and entertaining rooms spill onto a series of spectacular balconies and terraces, each oriented to capture the ever-changing hues of sunrise and sunset over Long Island Sound. The kitchen, slightly staged with new countertops, offers both style and flexibility-ready for your personal touch to transform it into a culinary haven. This property is brimming with potential: imagine your own vacation escape for spring, summer, and fall, a lucrative VRBO investment, or an unforgettable wedding venue where guests are enveloped in the island's enchanting atmosphere. The primary suite is a world unto itself, boasting its own private balconies, a spa-inspired bath, and vistas that stretch to the horizon. Three additional bedrooms offer comfort and privacy for family and guests alike.

00 Potato Is, Branford
$3,875,000
4 Beds ⋅ 5 Baths ⋅ 24187684 MLS
Beautifully reimagined modern farmhouse on a quiet Greenwich cul-de-sac, offering 4 bedrooms, 4 full & 1 half baths across four finished levels. Renovated with a timeless coastal feel, featuring wide-plank white oak floors, abundant natural light, town utilities, natural gas, bluestone patios, EV-ready charge & a level backyard with possible pool site. The chef's kitchen, designed by an award-winning designer, offers Thermador appliances, custom cabinetry, center island, designer finishes & a custom banquette eat-in area, opening to the family room with fireplace and sliders to the blue-stone patio. The primary suite features two walk-in closets and a spa-like bath with radiant heated floors. Finished lower level offers flexible space. Finished walk-up attic with full bath provides ideal guest or office space. Minutes to Greenwich Ave, train & nature preserve, close to shopping, dining, parks, and nearby schools.

4 Sachem Ln, Greenwich
$3,850,000
5 Beds ⋅ 5 Baths ⋅ 24181784 MLS
This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the Village. Hidden from the road, it offers a sense of seclusion that is increasingly difficult to find. Rich with period details and timeless architectural character, the 5 bedroom, 4 full and 1 half bath home sits at one of the highest points on Harbor Road, where cooling summer breezes are a welcome feature. The property also includes a classic antique barn, pool, pool house, attached one-car garage, and detached two-car garage, creating a setting ideal for both everyday living and entertaining. While the home presents an exceptional opportunity for renovation and enhancement, its greatest assets cannot be replicated: its setting, scale, history, and location. For the next steward, it offers the chance to reimagine a treasured Southport property while preserving its authenticity and charm. Enjoy a quintessential Southport lifestyle with easy access to the Village, train station, Pequot Yacht Club, and the soon-to-open Southport General Store and Rose Hill Kitchen. Last offered for sale in 1989, opportunities like this rarely come to market. A true Southport gem ready for its next chapter

406 Harbor Rd, Fairfield
$3,800,000
5 Beds ⋅ 6 Baths ⋅ 24144031 MLS
Exceptional NEW CONSTRUCTION - Walk to Town - Experience a thoughtfully designed home by V&A Construction, a highly regarded local builder known for exceptional craftsmanship. Just a short walk to town, shops, restaurants and the train, the location is as convenient as it is desirable. The home features handcrafted cabinetry and millwork, wide-plank white oak floors and high ceilings throughout. Imported European windows and doors not only add a beautiful architectural element, but make the home feel exceptionally quiet and comfortable. A welcoming foyer opens to living and dining rooms, a private home office and a designer kitchen with breakfast nook, premium appliances and a fully equipped butler's pantry. The kitchen flows directly into a spacious family room with a wood-burning fireplace, creating an easy, open layout for everyday living and entertaining. The expansive mudroom offers generous storage, connects to a back staircase and leads to a spacious lower level that can accommodate a gym, media room and game room. The second floor includes five generously sized bedrooms, highlighted by a primary suite with dual walk-in closets and a spa-like bath with premium fixtures. A large third-floor loft provides flexible space for a playroom, additional office or a relaxed retreat. This award-winning builder is dedicated to creating homes of the highest quality. Rarely offered and not to be missed.

72 Old Kings Hwy S, Darien
$3,795,000
4 Beds ⋅ 4 Baths ⋅ 24171986 MLS
Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully renovated, offering flexibility with gracious living and dining rooms, a sun-filled sunroom, cozy family room, and a curated Chef's kitchen with Calacatta marble, bespoke cabinetry, and top-tier appliances. A serene Primary Suite and additional bedrooms upstairs, the home functions perfectly as-is-or as a future guest house or accessory residence with thoughtful modifications. The sweeping land provides ample room for a new main residence set further back on the property, while maintaining the current home for extended family, guests, staff, or as a pool house. Outdoor living is equally compelling, with an expansive covered stone terrace, fire pit, and open meadow-like grounds offering endless possibilities for a pool, tennis court, barn, or gardens. Whether you choose to embrace the home's timeless appeal or create a legacy estate tailored to your vision, this is a unique chance to live comfortably now while building for tomorrow-all in one of Westport's most coveted locations, just minutes to Westport's vibrant downtown with award winning restaurants, premium shopping, beaches, and train.

61 Clapboard Hill Rd, Westport
$3,795,000
4 Beds ⋅ 5 Baths ⋅ 24159613 MLS
At the edge of Stonington Harbor, where sailboats move slowly through the water and the village wakes each morning to the rhythm of the tide, 88 Water Street offers a rare opportunity to live directly within one of New England's most beloved coastal communities. This historic home dates to 1840, yet today it feels distinctly current following an extensive renovation completed in 2022. The result is a residence that respects its heritage while embracing the ease and openness expected of modern coastal living. Inside, more than 3,400 square feet of thoughtfully reimagined space unfold across multiple levels, with views of the harbor appearing at nearly every turn. The home's central living spaces flow naturally from one room to the next, creating an environment designed as much for relaxed daily life as it is for hosting friends and family. A spacious kitchen anchors the main level, centered around a generous island and complemented by casual gathering areas that invite conversation long after dinner ends. Nearby living and dining rooms retain the warmth and character expected in a home of this era, anchored by a traditional fireplace that brings a sense of intimacy to the space. Upstairs, the primary suite enjoys its own private outlook toward the water, with direct access to a deck that feels perfectly suited for quiet mornings overlooking the harbor. Additional bedrooms provide comfortable accommodations for family and guests.

88 Water St, Stonington
$3,750,000
5 Beds ⋅ 7 Baths ⋅ 24190774 MLS
A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

28 Walden Hill Rd, Guilford
$3,750,000
5 Beds ⋅ 7 Baths ⋅ 24178176 MLS
On Top of the World. Unparalleled Estate with complete privacy and breathtaking panoramic views overlooking Lake Lillinonah and distant hills in premier Bridgewater location. Newly constructed state-of-the-art 5-bedroom Main House, 2-bedroom Guest House, Pool & Pool Cabana. Long paved driveway winds through magnificent grounds with extraordinary mature landscaping curated with pristine specimen trees & bushes and beautifully designed gardens. Sunlit from dawn until dusk, this Georgian colonial was masterfully crafted with the highest quality materials featuring high ceilings, expansive walls of windows and exquisite architectural symmetry. A captivating Living Room with central fireplace, a formal Dining Room and a Sunroom are oriented due west with floor-to ceiling windows capturing exquisite sunset views. Chef's Kitchen with spacious Butler's Pantry. Inviting entrance gallery designed to showcase works of art. Two first-floor primary-bedroom suites with 3 exquisite full baths, custom walk-in dressing closets, and a handsome home office. Three additional bedrooms are located on the 2nd floor with adjacent upstairs Family Room. Indoor exercise pool. Gym/Wellness Spa with full bath. 3-car attached garage. Seamless indoor/outdoor living. Irrigation system. Cutting-edge mechanical systems. Gated entrance. 26+/- acres surrounded by land trust. Must See. Not replicable.

289 Northrop St, Bridgewater
$3,750,000
7 Beds ⋅ 7 Baths ⋅ 24170697 MLS
Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty-three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef's kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting family and friends. Winding paths traverse a landscape of remarkable diversity-open meadows, mature woodlands, and picturesque waterways-while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation.

151 Benson Hill Rd, Dover
$3,750,000
5 Beds ⋅ 6 Baths ⋅ 24132064 MLS
Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among notable estate properties and near Brett Woods Conservation Area (186 acres) and the Roy and Margot Larsen Wildlife Sanctuary (155 acres), with convenient access to the centers of Fairfield, Southport, and Westport and approximately 55 miles to Manhattan. Construction will begin after purchase and execution of the build contract. The site is approved for a pool, and a pool house can be added at additional cost. Also offered as land only, MLS #24114632, asking $1,300,000. Concept drawings, renderings, and photos are for design intent and aesthetic review. A rare opportunity to build in bucolic Greenfield Hill.

22 Brett Rd, Fairfield
$3,700,000
7 Beds ⋅ 7 Baths ⋅ 24173300 MLS
Nestled between the Lower Connecticut River and Long Island Sound, encircled by conservancy, this enchanting compound offers five distinct living environments blending the timeless character of early New England architecture with modern spaces for today's style of living. At the heart of the estate is a beautifully preserved 1787 Cape, with original fireplaces, rich with warmth and history. It is surrounded by formal English boxwood gardens, an intimate outdoor environment for restorative moments. The soaring post-and-beam barn with grand interiors, and a dramatic glass facade overlooking the quad creates an unforgettable setting for unique and elegant entertaining on both a small and large scale; it has hosted dinners for up to eighty. Two thoughtfully designed cottages provide private, charming and fully independent guest retreats. Reimagined in 2017, the Pool House introduces a modern contrast to the estate's historic soul. It features a full kitchen with double height ceilings, a book-lined great room, and a fully equipped gym, and seamless indoor-outdoor living besides the private Gunite pool, firepit, and alfresco dining areas. "The Greenhouse" offers a magical, foliage-filled glass ambience with softly glowing lights, a pavilion that transforms effortlessly from a refined clubroom into the most romantic of reception spaces. The expansive grounds feature gently cascading streams, a private pond, and generously landscaped gardens that create a truly one-of-a-kind.

155 Joshuatown Rd, Lyme
$3,695,000
4 Beds ⋅ 5 Baths ⋅ 24193922 MLS
Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a higher elevation, the home enjoys FEMA compliance with fewer stairs to the main living level than many neighboring properties. Sunlight pours through oversized windows, illuminating beautifully proportioned living spaces designed for both everyday comfort and effortless entertaining. The stunning chef's kitchen opens seamlessly to inviting gathering spaces and out to a private backyard featuring a spacious patio, outdoor fireplace, mature landscaping, and room for a pool. The flexible floor plan lives as four bedrooms, with a private third-floor suite and adjacent full bath offering an ideal extra bedroom, guest retreat, office or bonus space. Thoughtful features, including a full-house generator, provide an added layer of comfort and confidence, allowing the home to perform as beautifully as it lives. Adjacent to the coveted Sunnieholme neighborhood, this is a rare opportunity to own a beautifully crafted home in one of Fairfield's most desirable beachside locations, where coastal living, convenience, and enduring quality come together.

110 Judson Rd, Fairfield
$3,695,000
4 Beds ⋅ 4 Baths ⋅ 24183333 MLS
Welcome to one of Connecticut's most desirable waterfront communities. Pine Orchard blends waterfront recreation, country club access, historic coastal character and a relaxed luxury lifestyle. For generations, families have been drawn to this unique shoreline community for its natural beauty and convenient access to New York & Boston. 60 Island View with a contemporary open floor plan concept to ensure panoramic water views from just about every room. Scenic vista views of the famed Stony Creek Thimble Islands, Long Island Sound, Pine Orchard Yacht & Country Club will always be for your viewing pleasure. Nautical light house feature with sweeping staircase will greet you upon arrival as you pull into your oversized garage perfect for cars, truck or golf cart. A full workshop & storage area will ensure you are never out of space. Main floor living area provides maximum flexibility for living, working & entertaining. Each room with water views more breathtaking than the next. With the heart of the home being your custom dream kitchen with handmade cabinetry from Craft Maid, Majestic natural gas range, Sub Zero refrigerator, Miele double oven & dishwasher. Multiple wet bars & butler pantry will keep friends & family gathering at your home for years to come. Second floor consists of a primary bedroom suite with a full wall of glass that places you in one of the most beautiful settings on the Connecticut shoreline.

60 Island View Ave, Branford
$3,685,000
4 Beds ⋅ 6 Baths ⋅ 24180388 MLS
Welcome to this new construction project which is currently underway, with an expected completion date in the Summer of 2026. Discover the epitome of elegance and sophistication on a quiet street, in a coveted area in Westport! Stunning new luxury construction designed by renowned Coastal Luxury Homes. Known for their architectural brilliance & unparalleled craftsmanship, Coastal Luxury Homes are a testament to innovative design & meticulous attention to detail. The rich architecture features flowing lines, glass elements, & harmonious blend of natural materials, create a stunning visual impact. The interior showcases an open-concept layout that is as functional as it is beautiful. Every corner will showcase high-end finishes, from cabinetry to the designer fixtures. The rich hardwood floors guide you into the Living Room. Adjacent to the living area, the gourmet Kitchen awaits, boasting ample storage & a generous island that invites culinary creativity. The Kitchen is a chef's paradise, equipped with top-of-the-line appliances & designed for both entertaining & everyday living. The four Bedrooms with en-suite Bathrooms provide both privacy and comfort for family and guests. This home, offers not only luxury but also the convenience of nearby beaches, dining, and shopping. Don't miss the opportunity to own this architectural masterpiece presented by Coastal Luxury Homes

3 Laurel Ln, Westport
$3,625,000
5 Beds ⋅ 5 Baths ⋅ 24191233 MLS
Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

409 River Rd, Deep River
$3,600,000
5 Beds ⋅ 4 Baths ⋅ 24191296 MLS
Step back in time without sacrificing modern comfort at the historic Ebenezer Hawley Homestead, a remarkable circa 1785 Antique Colonial nestled on a beautifully landscaped property in Ridgefield. Lovingly maintained and thoughtfully updated, this one-of-a-kind residence seamlessly blends the charm of yesteryear with the conveniences of today. The impressive 4,136-square-foot main home offers five bedrooms, four full baths, and is rich in period details, including wide-board floors, multiple fireplaces, and timeless architectural character. A spectacular Great Room with a soaring fireplace provides the perfect gathering space for entertaining or relaxing, while modern upgrades, including a Buderus heating system, ensure year-round comfort. Outside, discover a private oasis featuring a sparkling in-ground saltwater pool, gorgeous, mature gardens, and picturesque landscaping that enhances the property's historic appeal. Adding exceptional versatility is a brand-new, detached 1,296-square-foot accessory dwelling featuring two bedrooms and one and a half bath-ideal for extended family, guests, a private home office, or potential rental income. This extraordinary property offers a rare opportunity to own a treasured piece of Ridgefield history with space, character, and endless possibilities. A truly special home that must be experienced to be appreciated.

214 Florida Hill Rd, Ridgefield
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 24183686 MLS
Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

268 South St, Roxbury
$3,600,000
8 Beds ⋅ 3 Baths ⋅ 24174202 MLS
Potential for residential conversion in the heart of downtown Greenwich. Located just two doors from Greenwich Avenue and moments from the Metro-North train station, 37 Arch Street presents an exceptionally rare opportunity to create a one-of-a-kind in-town residence, mixed-use property, or continue as boutique commercial space. Situated within the Central Greenwich Business District zone, the property offers potential for residential, mixed-use, office, retail, or medical use (buyer to conduct all due diligence with the Town of Greenwich). This charming circa-1815 Federal-style building offers approximately 3,090 SF on an oversized 8,158 SF lot with the rare convenience of 8 on-site outdoor parking spaces plus 2 garage spaces - an extraordinary amenity for downtown Greenwich. The property is currently configured as executive office space and is in excellent condition, providing flexibility for investors, developers, or owner-users seeking immediate income while planning a future conversion or redevelopment. Prime walk-to-town location near Greenwich Avenue's luxury shopping, restaurants, parks, and transportation in one of Fairfield County's most sought-after downtown locations.

37 Arch St, Greenwich
$3,600,000
5 Beds ⋅ 6 Baths ⋅ 24118657 MLS
Create your Ridgefield legacy with this proposed luxury residence. With four or five en-suite bedrooms and an open floor plan, our elevated property with sweeping views is a once in a lifetime opportunity on an impeccable homesite. Opportunities like this are nearly extinct. This spectacular 3-acre parcel, one of the last remaining premiere building sites in Ridgefield, offers a rare opportunity to create a home as remarkable as its address. In Fairfield County's crown jewel address boasting award winning schools, a vibrant downtown, the Aldrich Contemporary Art Museum, Ridgefield Playhouse, Ridgefield Golf Course, hiking trails all within an easy commute to Manhattan. This is a rare chance to build our designs or your own vision with top local builder. Must contact listing broker for information. Please only serious inquiries. Builder will discuss lot sale only if you insist on your own contractor.

399 Ridgebury Rd, Ridgefield
$3,595,000
7 Beds ⋅ 6 Baths ⋅ 24189710 MLS
Exquisite Stonington Estate. Set amidst 10.19 manicured acres of breathtaking privacy and natural beauty, the extraordinary Crossover Estate offers the very best of refined coastal living just moments from the charming Stonington Borough and Historic Downtown Mystic. The best of One-Level Living. This exceptional family compound is bordered by a tranquil pond and brook on one side, with a picturesque estuary leading to Long Island Sound on the other. Ideally positioned between Boston and New York City, and only minutes to Mystic, Watch Hill and the Mystic Amtrak station, this remarkable estate offers effortless access for both weekend escapes and year-round enjoyment. The best of one-level living with an expansive and luxurious primary suite. The stunning main residence features 4 spacious bedrooms, 3 Full 2 Half beautifully appointed baths, designed with elegant comfort and seamless entertaining in mind. Exceptional interior finishes include a gourmet chef's kitchen with premium Wolf appliances, steam oven, microwave drawer, custom cabinetry, and sophisticated designer details throughout. Complimenting the main residence is a charming 3 Bedroom 1,276 Sq Ft Guest House, along with a spectacular pool and pool house complete with full kitchen, bath, and sauna, and Sports Court. Also - Main House with 3 Br Guest House, Pool with Pool House and Sports Court situated on 10.19 manicured acres and including 11.07 acre building lot are available for $4,459,000. Continued:

455 Stonington Rd, Stonington
$3,595,000
5 Beds ⋅ 4 Baths ⋅ 24190330 MLS
Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined living. Set on a .45 private lot, this meticulously maintained antique residence spans approximately 3,769 square feet and captures serene water views from its beautifully landscaped grounds. Despite its central village location, just moments to shops, dining, and marinas, the home offers an exceptional sense of privacy and tranquility. Rich in architectural charm, the home features soaring ceilings, expansive windows, and elegant, light-filled interiors that reflect generations of thoughtful stewardship. Once known as one of the village's grand homes, its legacy continues today as a warm and inviting retreat with sophisticated style and historic integrity. Designed for both everyday living and entertaining, the property includes a spacious three-car garage and generous living areas that honor its past while accommodating modern lifestyles. The grounds unfold toward the water, offering a peaceful backdrop and a true connection to Essex's coastal beauty. This Historic Essex Village waterfront home is a rare offering where heritage, location, and lifestyle converge.

10 Scholes Ln, Essex
$3,595,000
5 Beds ⋅ 6 Baths ⋅ 24163499 MLS
Welcome home to the Gold Coast of Norwalk. Location, space and timeless design come together in this stunning turn-key colonial with waterviews of Long Island Sound. Set on one acre in Norwalk's coveted Shorehaven neighborhood, it's just a short walk to Sandy Beach and the Sprite Island Yacht Club boat launch. Custom features and 10-foot ceilings elevate the main level and make it ideal for both everyday living and entertaining. The family room flows seamlessly into the eat-in kitchen. A generous deck overlooking the backyard is perfect for relaxing or hosting friends. The first floor private office with full bath also serves as a guest bedroom. Upstairs, the primary bedroom features a fireplace and a sumptuous bath that opens to an outdoor deck. The third floor offers an entertainment center with full bath and an additional office space. New additions include a full house generator, outdoor lighting, a fire pit and patio. Nearby is the Shorehaven Country Club as well as The Shore and Country Club, a private club on Long Island Sound offering members a 25 yard pool, a separate wading pool, 10 tennis courts, beach areas on the Sound, a marina with boat slips, as well as dining and social areas for events, meals and gatherings. 3 Shorehaven is just minutes to Norwalk's famous SoNo district for great restaurants and entertainment. Room for a pool. Within one hour to NYC.

3 Shorehaven Rd, Norwalk
$3,595,000
7 Beds ⋅ 7 Baths ⋅ 24147408 MLS
Cove Lawn - Historic Italianate Estate with Water Views & Guest House. Walk to Stonington Borough. Experience the charm of village living just moments from Historic Stonington Borough at Cove Lawn, a magnificent c.1860 Italianate estate steeped in local history and timeless elegance. Ideally located just a short stroll to the Borough's deep-water marinas, boutique shopping, seaside cafes, and fine restaurants, this extraordinary property offers the rare combination of estate privacy with walkable coastal village convenience. Set on 3.19 beautifully landscaped acres, the property features a stately 7-Bedroom, 5-Full and 2-Half Bath main residence, an attached au pair apartment, a sparkling inground pool, a charming 2-Bedroom, 1 1/2-Bath guest house, and an impressive three-bay garage/barn of approximately 2,000 sq. ft. The elegant 7,060 sq. ft. main residence has been carefully restored and thoughtfully modernized while preserving its historic architectural character. Inside, graceful 10+ foot ceilings, original hardwood floors, numerous marble fireplaces and exquisite period moldings create a sense of grandeur throughout. Many rooms capture lovely water views, bringing the beauty of the nearby harbor into everyday living. The 1,098 sq. ft. 2 Bedroom guest house provides ideal accommodations for extended family, guests, or caretakers, while the expansive grounds offer privacy and serenity rarely found so close to the village center.

259 N Main St, Stonington
$3,550,000
6 Beds ⋅ 7 Baths ⋅ 24191286 MLS
In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. Located on a private cul-de-sac, this home is a true compound-balanced, gracious, and masterfully executed, offering unparalleled living inside and out. Once you have arrived, it will be hard to leave!

9 N Ridge Rd, Westport
$3,500,000
3 Beds ⋅ 3 Baths ⋅ 24196231 MLS
Where the river meets the ocean, an extraordinary waterfront legacy awaits. Discover The River Estate at Shawandassee, one of the region's most captivating riverfront estates, where 1.06 acres of meticulously manicured, park-like grounds and more than 200 feet of pristine waterfront create an unparalleled coastal sanctuary. Launch your boat from the private deep-water dock and cruise effortlessly to Long Island Sound, Fishers Island, and beyond, or spend the day enjoying the rare grandfathered waterfront boathouse complete with electricity and running water, and a private beach. Spend your days sport fishing, shellfishing, kayaking, paddleboarding, boating or simply soaking in the serenity of life on the water. Complementing this remarkable setting is a charming pony barn attached to a two-car garage and a beautifully updated 2,700-square-foot residence offering three bedrooms and three full baths. This is far more than an exceptional property-it is a once-in-a-lifetime waterfront estate where luxury, privacy, and the timeless beauty of New England's coastline come together to create a lifestyle few will ever experience. Inside, timeless craftsmanship and warmth welcome you home. The inviting living room welcomes you with hardwood floors, a classic wood-burning fireplace and a picturesque window seat perfectly, positioned to take in the patio, beautifully landscaped grounds and tranquil water views.

7 Shawandassee Rd, Waterford

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