Refine Search
Sort by
40 Pond Rd, Old Lyme
$3,975,000
6 Beds ⋅ 9 Baths ⋅ 24176656 MLS
Rare beachfront opportunity at 40 Pond Road in Old Lyme, featuring two homes on one lot with spectacular views of Long Island Sound. This exceptional coastal property includes one beautifully remodeled home and one newly constructed home, offering flexibility as a primary residence, second-home retreat, or investment property with rental income potential. The two-home layout is ideal for hosting guests, multigenerational living, or exploring rental opportunities. Designed for modern coastal living, the new construction features sleek concrete floors, an open floor plan, abundant natural light, and stylish bathrooms. Seamless indoor-outdoor living extends to an expansive beachside deck-the perfect setting for entertaining, relaxing, and enjoying breathtaking water views. A private, exclusive mooring enhances the appeal for boating enthusiasts. A unique opportunity to enjoy a beachfront compound that combines contemporary design, coastal comfort, and the potential for personal enjoyment and investment income.

40 Pond Rd, Old Lyme

217 Wilton Rd, Westport
$3,950,000
6 Beds ⋅ 7 Baths ⋅ 24186096 MLS
Some homes are simply unforgettable. Set high above the street on 1.19 lush acres in coveted Old Hill, this extraordinary new residence blends striking architecture and sophisticated design. A gracious front porch overlooks a courtyard-like driveway. Created by Sam Development LLC.,CMS Architects, and Interior Designer Mary Beth Woods, this distinctive home offers approximately 6,000 SF across four levels, with 5 bedrooms, 5 baths, 2 half baths, 9' ceilings on the first and second floors, 6" white oak flooring, and exceptional details. The spectacular kitchen features high-end appliances, oversized island and walk-in pantry, opening to the family room with gas fireplace and breakfast area. Glass sliders lead to a granite patio and landscaped grounds. An elegant dining room with built-in buffet and bar and a glass doored living room/study complete the main level. The vaulted, beamed primary suite features a spa-like bath and two walk-in closets. Three additional bedrooms, spacious laundry, finished third- floor space with half bath, and a lower level with family room, bedroom,full bath, gym, and storage offer versatility. The detached 1,050 SF ADU is ideal for in-laws, guests, office/studio, or future pool house. Three-car garage with bonus room, spray-foam insulation, approximately 100 recessed lights. 22-KW Generac generator, 400-amp electrical services, and EV outlet. Come experience this exceptional Old Hill property and discover a home that stands apart.

217 Wilton Rd, Westport

7 Bailiwick Rd, Greenwich
$3,950,000
5 Beds ⋅ 6 Baths ⋅ 24205146 MLS
The best of brand-new living! Set on 1.4+ beautifully level acres in Greenwich's coveted Bailiwick Association, this 5,400+ SF custom transitional Colonial offers exceptional craftsmanship, extraordinary natural light and the ease of move-in-ready living. A welcoming front porch opens to a dramatic double-height foyer, while elegant living and dining rooms feature custom millwork, soaring ceilings and walls of sliding glass doors leading to expansive decks and patios. At the heart of the home, a stunning chef's kitchen with double islands, Sub-Zero and Wolf appliances, and a butler's pantry opens to a sun-filled vaulted breakfast area and family room. A first-floor ensuite bedroom with deck access, mudroom and two powder rooms complete the main level. Upstairs, the luxurious primary suite features vaulted ceilings, a gas fireplace, two walk-in closets and a marble bath with double vanities and an oversized rainfall shower. Four additional bedrooms, three full baths, an office, sitting area and laundry complete the second floor and the oversized three-car garage with room for lifts and additional parking. Minutes from Glenville and approximately 10 minutes to Greenwich Avenue and the train, this is a rare opportunity to enjoy brand-new living in a sought-after community!

7 Bailiwick Rd, Greenwich

297 Painter Hill Rd, Roxbury
$3,950,000
4 Beds ⋅ 7 Baths ⋅ 24192621 MLS
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury

95 Old Saugatuck Rd, Norwalk
$3,950,000
5 Beds ⋅ 7 Baths ⋅ 24187690 MLS
Stunning European-style mini-estate where rolling golf course greens meet breathtaking views of the Long Island Sound. Crafted with a timeless stone exterior, cedar roof, hardwood floors, and exquisite granite surfaces, this home offers an unparalleled lifestyle of privacy and sophistication. The heart of the home is an open-concept layout featuring a soaring 2-story family room with dramatic French doors that open to a backyard oasis. The chef's kitchen is equipped with high-end appliances, custom cabinetry, and a massive center island. The main floor boasts a formal dining room, a dedicated office with built-in bookshelves, and a luxurious primary suite featuring vaulted ceilings, a private screened porch overlooking the golf course, and a spa-like bath with a soaking tub and custom walk-in closet. Upstairs, a stunning balcony looks out to the Sound, leading to 4 generous bedrooms: 2 en-suites and 2 sharing a Jack-and-Jill bath. The lower level is the ultimate entertainment hub, offering 3,000 sq ft of finished space designed as a private club with a state-of-the-art gym, connoisseur's wine room, spacious billiards room, and full bath. Step outside to a private paradise with manicured gardens, a sparkling gunite pool, and a pool house with a full bath. A fully equipped outdoor kitchen makes summer hosting an absolute breeze. Do not miss this rare opportunity to own a resort-style masterpiece.

95 Old Saugatuck Rd, Norwalk

42 Hy Vue Ter, Millerton
$3,950,000
4 Beds ⋅ 6 Baths ⋅ 24165995 MLS
Welcome to the Hudson Valley Dream Home - Introduced by Hudson Valley Magazine Presented in collaboration with Hudson Valley Magazine as their inaugural "Dream Home", this custom-built modern farmhouse is near completion and offers an extraordinary opportunity to own a Hudson Valley compound where collaborative vision meets architectural excellence. Located only 2 minutes from village of Millerton and set on 14 pristine acres with private ponds and surrounded by protected land, this single-level contemporary farmhouse spans nearly 6,000 square feet of thoughtfully conceived living space. A dramatic vaulted entry foyer leads into a grand Great Room, where living, dining and kitchen converge beneath a soaring ceiling and features a fireplace and walls of glass that frame the bluestone terraces and serene landscape beyond. The four, massive bedroom suites include two equal luxurious primary suites on opposite corners of the home. A large, dedicated media room, private office, 2 half baths and a bonus 2nd-floor wellness studio complete an exceptional floor plan designed for both grand entertaining and quiet, inspired living. With the exterior complete, the buyer has the rare opportunity to collaborate with the builder and the magazine's creative team to finish the interior to their own aesthetic vision. Luxurious fixtures like custom cabinetry, high-end Fisher Paykel appliances and designer details throughout ensure the finished product will be nothing short of remark

42 Hy Vue Ter, Millerton

184 Fern Ave, Litchfield
$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

80-90 Comstock Hill Rd, Norwalk
$3,900,000
6 Beds ⋅ 6 Baths ⋅ 24163781 MLS
YOUR HORSE. YOUR BARN. YOUR VISION. Set on more than 7 level acres in the heart of Fairfield County, 80 to 90 Comstock Hill Avenue presents a rare opportunity to own an established equestrian estate with exceptional scale, flexibility, and a unique combination of land, location, and infrastructure. Whether your vision is a training facility, elite boarding operation, equestrian wellness retreat, family farm, or private compound, this property provides the ideal foundation. The existing equestrian amenities offer immediate functionality while creating opportunities to thoughtfully tailor the estate to your own lifestyle and long-term goals. Ideally situated just one hour from Manhattan and minutes from Westport, New Canaan, Wilton, Darien, and Rowayton, the property offers the serenity of country living with exceptional access to Fairfield County's most desirable communities. Whether you preserve its equestrian legacy or shape its next chapter, 80 to 90 Comstock Hill Avenue represents one of Fairfield County's most compelling opportunities to create a truly exceptional estate.

80-90 Comstock Hill Rd, Norwalk

213 Beaver Brook Rd, Lyme
$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

8 Norfield Woods Rd, Weston
$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

00 Potato Is, Branford
$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

484 Joshuatown Rd, Lyme
$3,850,000
5 Beds ⋅ 8 Baths ⋅ 24211823 MLS
Re-imagined in partnership with Old Lyme's Nautilus Architects, this exceptional Whalebone Cove property offers commanding views, dock access and a rare connection to nature. A stone and pebble drive winds through mature woodlands and an orchard to park-like grounds dotted with native and specimen plantings, descending to the Cove. Thoughtfully designed for beauty, sustainability and long-term ease of living, this quietly stunning home boasts custom millwork, cedar-lined cabinetry and exceptional materials throughout. A barrel-vaulted entry beneath an 18th-century German stained-glass window leads to wonderfully versatile spaces. First, the main level vaulted kitchen, great room and dining area with a professional copper hood, soapstone sink, onyx accents and wood-burning fireplace, all illuminated by western sunsets. Ipe decks and bluestone patios with pergolas create inviting spaces to entertain. Accessibility is seamlessly integrated with level thresholds, widened doorways and an elevator. The main level continues in the library and adjoining four season sun porch. A vaulted primary suite features a steam shower, air-jet tub, cherry built-ins, a writing room/office and Cove views. An additional bedroom is found on this level with ensuite bath and private laundry. Two additional bedrooms are located on the upper level. The media and exercise rooms, office/bedroom, large Scandinavian-style sauna and a handicap-accessible bedroom suite with shower, soaking tub, generous book-

484 Joshuatown Rd, Lyme

406 Harbor Rd, Fairfield
$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

624 Penfield Rd, Fairfield
$3,800,000
5 Beds ⋅ 6 Baths ⋅ 24217477 MLS
PRIME Beach Area Colonial, just 6 years young! Welcome to 624 Penfield Road, a home that brings people together; gorgeous water views, a private deck for watching 4th of July fireworks, steps to miles of sandy beaches & a new in-ground pool & spa await. Spend summer afternoons poolside, entertain family & friends beneath the covered loggia or unwind in the spa as the winter snow falls. This home is designed to create lasting memories. Offering 11 spacious rooms spanning 4 levels designed for comfort & flexibility. 9 ft ceilings, white oak hardwood floors, custom built-ins & detailed millwork create an atmosphere where every room is streaming w/ natural light even on the cloudiest of days. The well-designed eat-in kitchen features an oversized island, butler's pantry w/ wine fridge & cooling drawers & high-end appliances. The inviting family room offers a gas fireplace & opens to the deck, while a beautifully appointed office w/ custom built-ins provides access to the front deck. The formal dining room w/ custom millwork, also opens to the front deck, extending entertaining outdoors. Elevator provides access to all 3 levels. The upper levels feature 5 spacious en-suite bedrooms, a bonus room complete w/ a wet bar & 2 decks w/ water views. The new in-ground pool & hot tub w/ built-in grill area & loggia are surrounded by gorgeous coastal plantings. A generator, irrigations system, multiple decks, 3 car garage + great storage. The best of everything all in one in the beach area!

624 Penfield Rd, Fairfield

24 Graenest Ridge Rd, Wilton
$3,800,000
3 Beds ⋅ 4 Baths ⋅ 24201990 MLS
Mid-Century Modern, Reimagined. This singular residence is a compelling conversation between two architectural eras, where a gracious 1950s post-and-beam home designed by Robert Peterson, who studied under Mies van der Rohe, meets a striking contemporary addition by architect Zehra Kuz Mackin. The original structure, defined by its low-slung roofline and classic Mid-Century proportions, has been thoughtfully opened and refined, allowing light to move freely through beautifully composed interiors. Created to accommodate an art collection, guests and vintage automobiles, the zinc-and-glass addition introduces a distinctly modern vocabulary while remaining remarkably harmonious with the original architecture. A sculptural glass-and-steel staircase, gallery-like spaces, private guest suite and collector's garage blur the distinction between residence and exhibition space, yet the home remains inviting and eminently livable. The interior of the original house has been substantially renovated including a recent kitchen makeover. Beyond the glass, architecture gives way to landscape. A serene, spa-like pool creates an extraordinary sense of privacy and retreat. Rare, sophisticated and impossible to replicate, this is modernism not preserved in amber, but beautifully evolved.

24 Graenest Ridge Rd, Wilton

39 Keelers Ridge Rd, Wilton
$3,795,000
5 Beds ⋅ 7 Baths ⋅ 24215990 MLS
FOR SALE OR LEASE. ALSO AVAILABLE FOR RENT AT $15,000/MONTH.Tucked away on a private cul-de-sac in Wilton's sought-after Keelers Ridge neighborhood, this exceptionally maintained estate spans 2.28 acres of professionally landscaped grounds. Offering over 9,100+ sq. ft. of total finished space across the main residence and heated/cooled pool house, the property enjoys complete privacy and ideal positioning for both morning sunrises and evening sunsets. 9,100+ Sq Ft...Main House 6,115 sq. ft. Lower Level is finished with 1,995 sq. ft. and Pool House 1031 sq. ft. The main residence features 5 bedrooms, 4 full and 3 half baths, including a convenient main-level bedroom suite. The finished lower level adds dedicated space for a wine cellar, gym, rec room, plus 1,040 sq. ft. of unfinished basement for storage and utilities. A whole-house Crestron sound system (Sonos compatible) runs throughout. Designed for effortless indoor-outdoor entertaining, two expansive stone patios-each equipped with its own outdoor kitchen-overlook the gardens, newly built cedar pergolas, and heated pool with spa. Topped with a classic cupola, the pool house includes central HVAC, a full bath, kitchenette, and a 740 sq. ft. unfinished basement-ideal for poolside hosting and relaxation. Major mechanicals and upgrades: new roof, gutters and downspout (2026), new HVAC system (2024), whole-house generator (2021/22).

39 Keelers Ridge Rd, Wilton

224 Kuhne Rd, Southbury
$3,795,000
5 Beds ⋅ 7 Baths ⋅ 24208495 MLS
LAKEFRONT LUXURY. NEARLY COMPLETE. Your Lake Lillinonah dream is almost here. Set directly on the water, this extraordinary new residence offers a rare opportunity to own a brand-new architectural showpiece in one of the lake's most coveted settings. Designed for elevated entertaining and effortless everyday living, the dramatic two-story living room flows seamlessly into the kitchen and formal dining room, all framed by beautiful lake views. Five en suite bedrooms-with room for a sixth-are complemented by two private offices, a play/hang-out space, and a family room. The lower level takes lake living to another level, featuring a game room and impressive great room with gas fireplace and fabulous bar, plus a dedicated changing room and shower room for effortless transitions from water to home. A separate, thoughtfully planned space is plumbed for a plunge pool, sauna, hot tub, or private wellness retreat. Every detail has been designed around gathering, relaxing, working, and enjoying the lake. A designated elevator shaft is already in place, adding convenience and future flexibility. Construction is nearing completion. Come experience the setting, envision the possibilities, and make this extraordinary Lake Lillinonah retreat your own.

224 Kuhne Rd, Southbury

23 Lake Dr N, New Fairfield
$3,750,000
5 Beds ⋅ 4 Baths ⋅ 24205382 MLS
Rare opportunity to own your family compound in Candlewood Isle. There are 2 separate residential waterfront homes on one parcel of land. It is set on a premium gently sloping lot with western exposure & 100' of private waterfront on Candlewood Lake. The western exposure will allow sun on your compound all year long with wonderful sunsets. The primary residence is a 3 bedroom 3 bathroom home with 2940 square feet, including the finished walkout lower level. It is a contemporary style with hardwood floors, cathedral ceiling, floor to ceiling stone fireplace flanked with stained glass windows on either side of the fireplace, a custom bar and built ins. French doors lead to wrap around deck with great lake views. Formal dining room has hardwood floors, dentil molding & raised panel wainscotting and a French door leading to the deck. The guest cottage shows 3 bedrooms and 2 full baths. The cottage's upper level has full kitchen, wrap around fireplace, hardwood floors, 2 bedrooms and wood paneling. The lower level of the cottage has laundry, a full bath, 1 bedroom and a family game room. Both the primary residence & cottage are direct waterfront with easy access to your boat dock. The outside space is enhanced a patio, koi pond and mature landscaping. Year round comfort with modern mechanical systems. Candlewood Isle is a sought after gated community with numerous social & recreational opportunities including children's summer programs & pickleball & tennis.

23 Lake Dr N, New Fairfield

323 River Rd, Deep River
$3,750,000
5 Beds ⋅ 6 Baths ⋅ 24192020 MLS
Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a dock and lift! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled with natural light and captures river views, seamlessly blending the ever-changing beauty of the water with miles of pristine, undeveloped landscape. Whether watching boats glide along the river, bald eagles and ospreys soar overhead, or vibrant sunsets reflect across the water, the connection to nature is simply unrivaled. The luxurious primary suite is a private sanctuary, perfectly positioned to showcase the breathtaking riverfront setting and spectacular sunset views. Inside, three fireplaces create warmth and ambiance, offering intimate gathering spaces for cozy evenings and seasonal get-togethers. This unique Deep River property is conveniently located to Essex Village, which is recognized as one of America's "Best Small Towns" where one can enjoy boutique shopping, restaurants, marinas and quintessential New England charm, all while returning to the peace and privacy of your own waterfront retreat. This stunning property is situated two hours from Boston and New York City, and offers convenient access to airports in New haven, Hartford and Providence.

323 River Rd, Deep River

1 Oak Dr, New Fairfield
$3,750,000
3 Beds ⋅ 4 Baths ⋅ 24184415 MLS
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 2006, 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.

1 Oak Dr, New Fairfield

700 Hollow Tree Ridge Rd, Darien
$3,699,500
5 Beds ⋅ 6 Baths ⋅ 24198712 MLS
A private country estate with exceptional proximity to New York City, this Georgian Revival Colonial on nearly two acres combines timeless architecture with extensive renovation and expansion. Surrounded by mature specimen trees, expansive lawns and gardens, the property overlooks a tranquil pond and fountain, bordering Land Trust woods, creating a feeling of a serenity and nature. The beautifully proportioned interiors of more than 5000 square feet, feature herringbone and hardwood floors, 9 foot first floor ceilings and floor to ceiling windows that open to the huge back terraces overlooking pond. Formal living and dining rooms flow naturally to comfortable family spaces with a custom kitchen opening to sun filled family room with terrace and leads up to a huge playroom and 4 bedroom wing, with a separate entrance gym on main floor. A gracious primary wing with fabulous views houses his and her bathrooms, a huge his/her walk-in closet and office. A rare opportunity to own a residence where architectural distinction, privacy and extraordinary grounds come together in an exceptional setting in this coastal community roughly 40 miles to Manhattan, with great schools, two beautiful public beaches, new waterfront park, and all within 5-7 mins from the train and newly re-imagined downtown.

700 Hollow Tree Ridge Rd, Darien

9 Berkeley Rd, Westport
$3,695,000
5 Beds ⋅ 5 Baths ⋅ 24209539 MLS
Exceptional new construction, 9 Berkeley Road presents a sophisticated interpretation of modern Westport living, blending timeless architecture with beautifully considered spaces and an exceptional floor plan. Gracious proportions, abundant natural light and 9-foot ceilings create an immediate sense of understated luxury throughout the main level. At the heart of the home, an expansive chef's kitchen with separate scullery and breakfast area opens seamlessly to a stunning family room accented by oak ceiling beams. Formal living and dining rooms provide elegant settings for entertaining, while a private home office offers a quiet retreat. A beautifully designed first-floor guest suite with full bath and walk-in closet provides privacy and flexibility for family and guests. Expansive doors extend the living spaces outdoors to a generous rear deck, complemented by a bluestone-covered porch for effortless indoor-outdoor entertaining. Upstairs, the luxurious primary suite is a private sanctuary featuring a spacious bedroom, dressing area, walk-in closet and beautifully proportioned bath. Three additional bedrooms, multiple baths, generous closets, a dedicated laundry room and loft complete the second level. Sophisticated yet inviting, and an exceptional opportunity to own a thoughtfully designed new residence where elevated style, modern luxury and effortless livability come together in one of Westport's most desirable settings. *REPRESENTAIVE IMAGES* Agent/owner

9 Berkeley Rd, Westport

34 Sherwood Ln, New Canaan
$3,695,000
6 Beds ⋅ 8 Baths ⋅ 24203727 MLS
Gracious colonial set on 3.74 private acres along a quiet west-side cul-de-sac. This cherished estate setting offers an exceptional blend of privacy, recreation, and convenience, just two miles from town and the train. The private grounds feature a Glengate Gunite pool, cabana with bath, and a barn with stables where the owners once kept horses for riding on nearby Land Trust trails. Offered for the first time in more than 50 years, this center-hall Colonial features six bedrooms, five full and three half baths, with 6,300 square feet of living space, and an additional 800 square feet of finished lower-level space. Thoughtfully renovated and expanded by Judith Larsen designs in 2005, the residence includes a beautifully appointed kitchen, an open family room with vaulted ceilings, lovely breakfast room overlooking grounds and a private in-law suite with its own entrance . Other features are 4 car garage, full house generator, pond views and driveway alert. Beautifully proportioned interiors and multiple gathering spaces make the home equally suited to comfortable everyday living and gracious entertaining. French doors spanning the rear of the residence open directly to the grounds, creating a seamless connection among the home, pool, cabana, and expansive property. A truly rare and treasured offering in one of New Canaan's most desirable west-side settings.

34 Sherwood Ln, New Canaan

110 Judson Rd, Fairfield
$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

274 Joshuatown Rd, Lyme
$3,695,000
4 Beds ⋅ 6 Baths ⋅ 24186404 MLS
High above the Connecticut River, architecture & landscape come together in a home unlike any other - The Sanctuary. Privately sited on 18 acres chosen for their light, elevation, and extraordinary sense of place, 274 Joshuatown Road was designed by acclaimed architect Stephen Jacobs as his own home and is now offered by only its second owner. It is the expression of a singular idea: that exceptional architecture should not simply be admired, but lived in. Jacobs considered every element of the home in relationship to its surroundings, from its precise orientation on the land to the changing path of the sun throughout the seasons. Walls of glass frame the landscape as an ever-changing work of art, while distinctive brise-soleil fins temper direct sunlight according to the season. The result is a home deeply connected to nature, filled with light when welcomed, sheltered when needed, and constantly in conversation with the landscape beyond. For all of its architectural significance, perhaps the home's greatest surprise is how remarkably approachable it feels. Grand in vision yet quietly livable, its spaces are beautifully scaled for everyday life. The living room is anchored by an 18' natural stone fireplace opposite a soaring wall of glass, equally suited to a quiet evening or a room full of guests. The kitchen with high end appliances and oversized island allows for an informal gathering space adjacent to the dining area with seating for 12.

274 Joshuatown Rd, Lyme

15 Wildcat Rd, Darien
$3,695,000
4 Beds ⋅ 4 Baths ⋅ 24186583 MLS
Originally the sole residence on Wildcat Road, this distinguished 1925 stone manor blends timeless architectural elegance with a commanding setting. Located within Darien's coveted Delafield Island private association, the property is approached by a sweeping circular drive and surrounded by mature landscaping offering a rare sense of privacy, grandeur, and permanence, just minutes from downtown Darien, the Metro-North train, beaches, and Great Island. Rich in character and craftsmanship, the residence showcases architectural details rarely found today, including soaring 12-foot ceilings, a dramatic circular staircase, five fireplaces, Juliet balconies, vintage servant bells, graceful arches, skylights, and a sun-filled glass solarium. Thoughtfully designed for both grand entertaining and comfortable everyday living, the spacious country kitchen opens to an expansive deck overlooking the surrounding natural landscape. Adding to the property's exceptional appeal, several acres of protected land trust border the rear of the home, preserving a tranquil backdrop and enhancing the estate-like setting. Whether hosting family gatherings, entertaining guests, or simply enjoying the peace and beauty of its surroundings, 15 Wildcat Road offers a unique opportunity to own one of Delafield Island's most distinctive and historic homes.

15 Wildcat Rd, Darien

248 Turtle Back Rd, New Canaan
$3,625,000
5 Beds ⋅ 6 Baths ⋅ 24178727 MLS
Classic New England architecture, beautifully proportioned interiors and exceptional privacy come together at 248 Turtle Back Road, a distinguished five-bedroom Colonial offering 5,291 square feet of living space in one of New Canaan's most desirable settings. Inside, the home is filled with warmth, character and natural light. The impressive great room features a vaulted beamed ceiling, creating a dramatic yet inviting space for everyday living and entertaining. An eat-in kitchen with center island, generous cabinetry and French doors is complemented by a dining room overlooking the gorgeous backyard, family room and den, providing both open gathering spaces and quieter places to retreat. Upstairs, the primary suite offers a private dressing room and en-suite bath, joined by three additional bedrooms, including an en-suite guest room. The fully finished walk-out lower level significantly expands the home's versatility with an additional bedroom and full bath, sunroom with wet bar, recreation room, office and exercise space. Outside, the home is set on 3.41 beautifully landscaped acres, where specimen plantings, mature trees, stone walls and terraces create a remarkable sense of privacy and established beauty. A circular drive, greenhouse and garage parking for 5 complete the property. Set just minutes from the heart of New Canaan, 248 Turtle Back Road pairs substantial, character-filled interiors with the privacy and scale that are rare to find this close to town.

248 Turtle Back Rd, New Canaan

140 Briar Patch Rd, Stonington
$3,600,000
4 Beds ⋅ 4 Baths ⋅ 24218198 MLS
Tucked away on a truly magical piece of land, this 1800 4-bedroom house not only offers you the charming main house, this home also includes a 2-bedroom guest cottage and a 2-story separate office/studio all situated on this 3.7 acre private property. Walk the open fields, listen to the stream winding through the property coming from the ponds above. Beautifully landscaped grounds, including vegetable garden, charming herb garden, pool and lots of spaces surrounded incredible rock formations. Whether you are after a peaceful retreat, room for lots of family and friends all surrounded by nature making this a truly special Stonington property. A rare opportunity to own a truly beautiful idyllic country spot to call your own.

140 Briar Patch Rd, Stonington

61 Clapboard Hill Rd, Westport
$3,600,000
4 Beds ⋅ 4 Baths ⋅ 24205877 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 altering 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

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!