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$2,260,000
4 Beds ⋅ 5 Baths ⋅ 24120730 MLS
Outstanding, updated, modern Colonial tucked into one of Wilton's most sought-after neighborhoods-just a short stroll to town. Offering 4/5 bedrooms, 3 full baths, and 2 half baths, this home seamlessly blends timeless style with thoughtful updates for today's lifestyle. Step inside to discover beautifully renovated kitchen and baths, sun-filled living spaces, and the comfort of geothermal heating and cooling. A whole-house generator provides peace of mind, while the open layout invites both everyday living and effortless entertaining. The back patio with built in grill and smoker as well as a gas fireplace is perfect for summer/fall evenings with friends and family. The beautiful gardens designed and cared for by a master gardener are a living work of art. Lush, colorful, and inviting in every season. This rare combination of walk-to-town convenience, modern updates, and stunning gardens makes 81 Graenest Ridge Road a true gem in Wilton. Please submit "Highest and Best" Offers by Tuesday 9/16 at noon.

81 Graenest Ridge Rd, Wilton
$2,258,000
4 Beds ⋅ 3 Baths ⋅ 24159158 MLS
Welcome to 3 Abby Road in Darien, a charming four-bedroom Colonial that blends timeless character with a bright, inviting layout. This beautifully maintained home features lovely moldings throughout and an abundance of natural sunlight that fills every room. The main level offers a wonderful open floor plan, creating an easy flow for living and entertaining. Spacious living areas connect seamlessly, making the home feel both comfortable and welcoming. Outside, the property truly shines with its meticulously landscaped, fenced garden and backyard-an ideal setting for relaxing and entertaining. Upstairs, the primary suite provides a private retreat complete with a walk-in closet and en-suite bathroom designed for comfort and relaxation. 3 additional bedrooms and bath complete the second floor. The fully finished lower level adds generous flexible living space-ideal for recreation, hobbies, or a home office. Also features a full laundry room. With bright interiors, modern touches, and classic charm, 3 Abbey Road offers a wonderful opportunity to enjoy easy living in one of Darien's most desirable communities.

3 Abbey Rd, Darien
$2,250,000
5 Beds ⋅ 3 Baths ⋅ 24167923 MLS
Some homes simply check boxes. This one redefines what life in Fairfield County can look like. Set on a coveted cul-de-sac in the heart of Wilton, this fully updated 5-bedroom retreat offers a rare blend of privacy, beauty, and convenience-just minutes to top-rated schools, Wilton Center, and the charming downtowns of Ridgefield and New Canaan. It's the way this home makes you feel that sets it apart. Step outside and exhale. Open skies, mature trees, and birdsong create a setting that feels worlds away, with the Wilton Riding Club, its summer camp, pool, tennis, paddle courts and miles of nature trails nearby. The expansive, usable property invites both relaxation and possibility, with room for a future pool, barn, or accessory dwelling unit (ADU). Designed for effortless living and entertaining, the outdoor spaces shine-from the expansive back deck at sunset to lawn games on the open grounds, to long dinners with friends on the screened-in porch. Unwind year-round in the barrel sauna, your own private wellness escape. A newly built fenced garden with raised beds awaits your vision-whether heirloom vegetables, fresh herbs, or cutting flowers. Inside, thoughtfully updated and carefully curated interiors deliver turnkey ease with timeless appeal. This is Wilton living at its most idyllic: natural, connected, and ready for what comes next.

25 English Dr, Wilton
$2,250,000
3 Beds ⋅ 3 Baths ⋅ 24161159 MLS
217 Mansfield Avenue presents a rare opportunity to secure a full, flat acre in one of North Darien's most desirable and rapidly evolving neighborhoods. Set on beautiful, level land, the property currently features a charming but dated Cape Cod-style home ready for its next chapter. Buyers may choose to renovate and restore the existing residence, bringing new life to its classic bones, or take advantage of the exceptional lot to build a substantial new construction home. The surrounding area supports significant value, with many newer homes commanding prices in the $4M-$6M range. A standout feature is the detached garage with a legal accessory apartment above-ideal for guest quarters, rental income, au pair space, or a private home office/studio. Whether you're an end user looking to customize, an investor, or a builder seeking a premier site, this property offers flexibility, value, and long-term upside in a highly sought-after Darien location.

217 Mansfield Ave, Darien
$2,250,000
6 Beds ⋅ 5 Baths ⋅ 24145307 MLS
This historic 1800s Colonial at 88 Drum Hill has been thoughtfully expanded and renovated, blending timeless charm with modern luxury. Original features - wide plank floors, multiple fireplaces, high ceilings, and classic moldings - honor the home's heritage, while updates create a fully livable, elegant residence. With 6 bedrooms, 4 full baths, and 1 half bath, this updated historic home offers flexible spaces for entertaining, work-from-home setups, and family gatherings. Set on a beautifully landscaped 2-acre property, the home features a stunning in-ground pool, outdoor entertaining areas, and private spaces perfect for relaxation. Unique historic touches, including a sleeping porch, library/study, and charming updated kitchen accents, blend seamlessly with modern comforts, including a chef's kitchen and light-filled living and dining areas. Ideally located minutes from Wilton Center and top schools, this luxury Wilton CT home combines historic integrity, modern updates, and a lifestyle designed for year-round enjoyment - a rare opportunity in Wilton real estate. Offer deadline: All offers must be submitted by Sunday, the 25th, at 4:00 PM.

88 Drum Hill Rd, Wilton
$2,250,000
3 Beds ⋅ 5 Baths ⋅ 24116057 MLS ⋅ Kensett BLDG.
Nestled in one of Kensett's most coveted locations, this stunning Norwood townhome backs to serene conservation land and blends refined luxury with modern comfort. Soaring 10-foot ceilings, gleaming hardwood floors, and abundant natural light create an inviting atmosphere. The gourmet kitchen features high-end appliances, a center island, and a Butler's pantry with walk-in storage. French doors open to a private bluestone terrace and backyard, ideal for outdoor dining or quiet mornings, while the space flows to the formal dining room and oversized living room with a gas fireplace. A chic powder room and a sunlit private den with its own gas fireplace complete the main level. Upstairs, the spacious primary suite offers a walk-in closet and spa-like bath with dual vanities, soaking tub, and glass shower. Two additional en-suite bedrooms with walk-in closets and a second-floor laundry room complete the level. The finished lower level adds 775 SF with a fourth bedroom, full bath, and flexible space for a playroom, home gym, or media room. A 2-car garage adds convenience. Kensett residents enjoy a stunning clubhouse, resort-style pool, fitness center, and scenic walking trails. This home combines luxury with effortless living, offering a truly maintenance-free lifestyle.

27 Kensett Ln Unit 27, Darien
$2,245,000
5 Beds ⋅ 7 Baths ⋅ 24090171 MLS
Simply stunning long western views of Lake Waramaug and the Litchfield Hills! 16 acre 5 bedroom estate located minutes from the lake with access to Warren Town Beach, hiking trails at Steep Rock or the Warren Land Trust. Village of New Preston is only minutes away for dinning and shopping. Less than 30 minutes to skiing at Mohawk Mtn. 5 large bedrooms with 3 full and 4 half baths spread over 3 floors. Fabulous screened in porch and deck to enjoy sunsets over the lake and Hopkins Winery. The perfect work from home residence with multiple work areas for privacy. Long driveway from road with mature landscaping, generator and over 300,000 in renovations since April 2023. Multiple locations for pool if desired.

293 Lake Rd, Warren
$2,237,500
4 Beds ⋅ 3 Baths ⋅ 24123260 MLS
Welcome to 8 Leeds Lane, one of just six homes on a private cul-de-sac in Darien. This meticulously maintained Colonial is move-in ready and offers the perfect blend of elegance, functionality, and comfort. Step inside to find sun-filled rooms, soaring ceilings, and generous open spaces ideal for today's lifestyle. Thoughtfully updated within the past decade and in amazing condition, the home has been cared for with the utmost pride. Set on a level, beautifully landscaped property just under 3/4 of an acre, the outdoor spaces are as inviting as the interior. From lush lawns to a charming fire pit area, this home is perfect for both relaxation and entertaining. The lower level is a standout feature-boasting a large finished media/playroom along with spotless, oversized storage space that is as impressive as it is practical. Truly turnkey, this is a rare opportunity to own a home that has been updated and maintained to a very high standard, offering light, space, and quality in every corner.

8 Leeds Ln, Darien
$2,230,000
4 Beds ⋅ 6 Baths ⋅ 24125694 MLS
Set on 12.48 picturesque acres in Sharon, this exceptional retreat includes an additional buildable lot with majestic mountain views. A stunning great room anchors the home, showcasing gleaming oak floors, expansive windows, and a magnificent brick fireplace with custom wood mantel. The open-concept kitchen includes stainless steel appliances and a skylit breakfast nook, while the adjacent keeping room charms with a stone wood-burning fireplace and original wood siding. The main level primary suite impresses with its own wood-burning fireplace adorned with Delft tile, complemented by a luxurious full bath featuring a soaking tub, double vanity, and separate shower. Above, a curved staircase leads to an open landing with built-in bookshelves, connecting to two bedrooms - one with an en-suite half bath - and a full bathroom. A bonus bedroom above the garage includes a full bath, private balcony, and direct staircase access from the keeping room. The outdoor living space centers around a refreshing gunite pool and extensive stone terrace, perfectly positioned to capture breathtaking mountain vistas. Modern conveniences include a two-bay garage, providing both comfort and security in this Litchfield County retreat. This Northwest Connecticut retreat combines countryside tranquility with sophisticated amenities, offering multiple possibilities with its additional buildable lot.

152 East St, Sharon
$2,228,000
6 Beds ⋅ 4 Baths ⋅ 24144929 MLS
Exceptional pride of ownership is evident in this rare opportunity to acquire a 14-unit multifamily asset in Woodstock, CT, with the option to combine with an additional 14 units at Pinecrest Apartments for portfolio sale. Built in 1987, the property features tenant-paid utilities with individual hot water heaters and electrical subpanels in every unit-supporting efficient operations and strong, consistent cash flow. The asset consists of 13 townhouse-style units and one garden unit with an attractive unit mix: (4) 1BR/1BA, (4) 1BR/1.5BA, (2) 2BR/1BA, and (4) 2BR/1.5BA. Ownership has invested significant capital upgrading units with premium finishes including granite countertops, shaker cabinetry, modern backsplashes, wide-plank flooring, and stainless-steel appliances. Tenant amenities include one garage per unit, ample off-street parking, private porches, built-in wall A/C sleeves, and four EV charging stations (8 plugs). Eight units offer in-unit washer/dryer hookups; remaining units are served by newly installed coin-operated laundry. Five storage units are located in the common laundry area, three of which present additional income potential. Strong occupancy, extensive capital improvements, and a low-maintenance operating profile make this a turn-key investment offering durable returns and long-term upside.

5 Brookside Ln, Woodstock
$2,225,000
3 Beds ⋅ 4 Baths ⋅ 24090280 MLS
66 Seminary The Watts Comstock House (c. 1872) is a 3 BR 3 1/2 bath home in the heart of downtown New Canaan. Fully restored and lovingly reimagined for today's living this 2,300 sq ft home with large 2 story barn/studio offers all new infrastructure while maintaining the original charm and the rare moldings and trim work. Located in the heart of town and an ideal distance to the train station, shops, and restaurants on one of New Canaan's oldest streets, the house includes a gorgeous new gourmet kitchen with pantry, all new bathrooms, new 8" plank flooring-a nod to the original hardwoods. 9' arched ceilings and sashed oversized windows allow natural light to flood this elegant home. In addition to the kitchen, living and dining rooms the main floor also includes an artfully tiled room with marble and soapstone, perfect for a breakfast nook or home office. Downstairs a mudroom leads to the cozy den with full bath and large laundry room. The top floor is complete with three airy sunlit BRs. Beautifully designed land and hardscapes offer myriad opportunity for 4 season living. Barn is easily converted to a garage and/or connected to heat and plumbing. Don't miss this unique opportunity to be a part of New Canaan history!

66 Seminary St, New Canaan
$2,220,000
5 Beds ⋅ 4 Baths ⋅ 24124533 MLS
Set high atop a ridge in one of Wilton's most desirable neighborhoods, offering STUNNING views of expansive landscape from nearly every room as well as its wraparound porch, this magnificent, 5/6 BR farmhouse Colonial is a charming yet sophisticated home for all 4 seasons. Front entrance boasts a 2-story foyer w/custom bookcases. Gorgeous living room offers a floor-to-ceiling fieldstone fireplace, wraparound bookcases, and a large bay window w/inviting window seat. French doors lead to a large, gourmet eat-in-kitchen w/new pantry & wine bar, as well as access to the lovely stone patio. Adjacent handsome den/library, w/patio & front porch access, offers custom built-ins & french doors. Host memorable dinner parties from the gracious dining room w/elegant pocket doors & swaying vista. Upstairs primary bedroom suite is complete w/vaulted ceiling, walk-in closets, & primary bath. Other upstairs highlights include 4 bedrooms, office/BR with vaulted ceiling, 2 full baths and a fabulous family room with large closets. The home's exterior is truly a private oasis, perfect for entertaining. The park-like manicured property to the rear of the home offers a renovated stone patio, magnificent gunite pool, lovely plantings, generous lawn space, & new outdoor shower. To the front, enjoy a private front-row seat to spectacular Wilton town fireworks, vibrant foliage & one of the best sledding hills in the area. Convenient & serene property is a rare find. See supplements for updates. A GEM!

87 Catalpa Rd, Wilton
$2,210,000
5 Beds ⋅ 4 Baths ⋅ 24168485 MLS
PLEASE PRESENT HIGHEST & BEST OFFERS BY 4:00PM MONDAY JUNE 8TH. Nestled on 1.67 beautiful park-like acres in a charming neighborhood just minutes from town, this classic 5-bedroom, 3.5-bath Colonial offers timeless appeal, comfortable living spaces, and a lovely natural setting. Thoughtfully maintained throughout, the home features generously sized rooms, a gracious living room with fireplace, family room with custom built-ins, formal dining room, and inviting spaces designed for both everyday living and entertaining. The sun-filled walkout lower level provides wonderful additional living space, featuring a large recreation room/playroom with a wall of glass sliders opening directly to the patio and expansive backyard. Overlooking sweeping lawns and mature landscaping, the property provides a beautiful backdrop for outdoor enjoyment. A spacious deck and patio offer ideal settings for relaxing, dining al fresco, or gathering with family and friends, while the level yard provides endless possibilities for recreation and play. Conveniently located close to town, schools, and parks, this special property offers the perfect blend of classic charm, comfortable living, and a picturesque setting.

21 Hickory Dr, New Canaan
$2,210,000
4 Beds ⋅ 3 Baths ⋅ 24169806 MLS
The seller is requesting highest and best offers by Tuesday at 3:00 PM. Perched gracefully atop a scenic hill, this quintessential Connecticut home offers a rare blend of privacy, charm, and opportunity. Set among grand estates and located just two miles from the New Canaan train station, the setting alone is enough to capture your heart. This is an exceptional opportunity to reimagine and elevate a truly special property into your own masterpiece. The home features generously scaled rooms, beautiful hardwood floors, and a screened-in porch you may never wish to leave. A welcoming family room with a striking brick fireplace overlooks the serene, private backyard, creating the perfect space to unwind or entertain. The residence includes a spacious living room and dining room, a private office ideal for working from home, and a lovely primary suite with en-suite bath. Three additional bedrooms and a two-car garage complete the offering. Please refer to the floor plan for full layout details. Beyond the home, enjoy all that New Canaan has to offer, from award-winning restaurants and unique boutique shopping to top-rated schools, beautiful parks, and an Olympic-sized town pool. With Metro-North access, commuting to New York City is seamless. Adding to the charm, Lee Memorial Garden is just a short stroll away, offering breathtaking displays of azaleas and rhododendrons each spring. A rare setting, a special home, and an opportunity not to be missed... welcome home.

215 Chichester Rd, New Canaan
$2,200,000
5 Beds ⋅ 4 Baths ⋅ 24178770 MLS
Renovated stone and shingle home, offering an abundance of character and modern amenities in a prime Main Street location. The residence features four finished levels with 5 bedrooms and 4 full baths, including a finished basement suitable for a playroom or gym. Perfectly sited on a large .56-acre in-town lot, the property includes a private backyard with an identified pool site. This home was renovated by SILWEL in 2022 and has been further updated by the current owner. The ideal location includes sidewalks, making it an easy walk to the train, village center, schools, and parks, providing convenient access to everything New Canaan has to offer.

304 Main St, New Canaan
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 24137275 MLS
Charming 1930's cottage has been totally updated. Loads of charm and loads of space. The kitchen alone is worth a look. Huge island, breakfast nook, top of the line appliances and it opens to a cozy den. The formal living room/dining room boasts historic details--amazing fireplace, leaded glass windows, wood beams, and cathedral ceiling. A large primary suite features 2 large walk in closets, updated spa like bath and office/loft, perfect for work from home space. There are 3 additional bedrooms and 2 more updated full baths. A large family room has a fireplace, built ins and sliding door to lovely bluestone terrace. The expansive yard is private and flat. The detached 2 car garage also has room for storage above. All of this conveniently located close to schools, parks, train and the Merritt Parkway. Must see.

32 Spring Water Ln, New Canaan
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 24173830 MLS
Highest and best by 2:00 pm on Monday, 5/18. Set on a coveted lower Nod Hill cul-de-sac, 45 Ryders Lane is the kind of home that quietly wins people over the moment they arrive. Classic in style yet thoughtfully updated for modern living, this 4-bedroom Colonial blends timeless architecture with warm, inviting spaces designed for real life. Inside, light pours through generously sized rooms, creating an easy elegance throughout the home. The renovated kitchen is both beautiful and functional, featuring a Wolf range, Sub-Zero refrigerator, and seamless flow into the home's casual gathering spaces. Nearby, the mudroom and updated laundry area make everyday living refreshingly effortless. Upstairs, the primary suite feels like a private retreat, complete with a beautifully renovated bath featuring radiant heated floors and a heated towel bar. Three additional spacious bedrooms, an updated hall bath, and a walk-up attic provide flexibility for today's lifestyle. Outside, summer practically writes its own plans. A charming screened porch overlooks the property, while the stone patio and expansive yard offer room for entertaining, gardening, or simply slowing down for the evening. Thoughtful improvements, including a new cedar roof, solar panels, upgraded electrical service, an invisible fence, and a new water heater, add comfort and peace of mind. A special home in one of Wilton's most sought-after neighborhoods.

45 Ryders Ln, Wilton
$2,200,000
5 Beds ⋅ 7 Baths ⋅ 24161810 MLS
A truly exceptional property situated high above Milne Lake. This residence offers breathtaking 180-degree water views, soaring ceilings, and abundant natural light throughout. Set on 4.13 acres, the estate is surrounded by nature and features a variety of premium amenities, including private walking paths, Zen gardens, bridges over streams, a dedicated pond and waterfall, and a tennis court. For relaxation and entertaining, the property boasts a spacious deck and patio, 2-story greenhouse atrium, as well as an impressive indoor heated pool. Additionally, the grounds include a separate guest house, caretaker cottage or in-law house. This unique and peaceful setting offers an unparalleled living experience.

160 Lantern Ridge Rd, New Canaan
$2,200,000
5 Beds ⋅ 6 Baths ⋅ 24158140 MLS
Rare opportunity to own in desirable Liberty Street area. This 1816 Federal-style residence & new detached historically designed barn, renovated and built by prominent historical design/build specialists Gulick & Co., creates a harmonious blend of formality and comfort. The main residence has 3,784 sq ft of living space, and the detached barn boasts 1,776 sq ft. The main residence is a combination of historic character and contemporary luxury. Wide-plank floors, custom millwork & formal parlors honor the past, while a chef's kitchen with SubZero & Bosch appliances, a light-filled great room with integrated home theater, and an enclosed porch with fireplace extend the living space across the seasons. Upstairs, the primary suite is a true retreat...bespoke cabinetry, coffee station, bar sink & bath with freestanding tub & oversized shower. The home has Container Store closets, Schlage smart locks, Lutron lighting, a whole house dehumidifier and generator, and a smart water monitoring system. The two story barn, built by Gulick & Co., features a spacious private office with full bath on the second floor and a stunning accessory apartment on the first floor with full kitchen, oak floors, reclaimed ceiling beams, an accessible bath, and its own septic system. The barn could be used as a studio, guest house, or income property. Great multi-generational situation. An extraordinary landmark home...where history, community & luxury converge. Total Sq Ft is House & Barn

137 Liberty St, Madison
$2,200,000
1 Baths ⋅ 24120149 MLS
SOLD! Located along scenic Connecticut State Route 156, Black Hall Marina offers slips for small powerboats & jet skis, a retail store as well as renting and providing access for kayaks & paddle boarders. 58 slips can accommodate boats up to 22 ft. as well as drive-on jet ski pads. Power & fresh water is available at the head of each dock. Structures include the 3 story main building, dockside boat house, workshop, storage container, picnic pergola and ample parking. A 768 sf. short-term rental apartment occupies the 3rd floor. Also included is a nearby, 6000 sf. warehouse for retail inventory storage and additional work space. Current revenue channels include: 1220 sf. retail paddle sports & fishing shop with huge e-commerce potential, slip rentals, boat rentals, guiding service, youth programs, fishing & boating lessons, eco tours, kayak rigging & installation as well as winter boat storage.

132 Shore Rd, Old Lyme
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 24117698 MLS
Welcome to Stones Throw Farm. A rare and magical estate tucked on over 23 rolling, pastoral acres in the heart of Colebrook, a true New England country retreat where timeless beauty and refined simplicity come together in perfect harmony. Set along a quiet country road, this idyllic sanctuary offers an extraordinary lifestyle steeped in elegance, comfort, and the gentle rhythms of nature. At the heart of the property is a 4,000+sf residence with roots dating back to 1795. Lovingly expanded and restored over the years, the home exudes both the charm of its historic origins and the ease of modern living. With 4 bedrooms, 3 1/2 baths, and 6 inviting fireplaces, every room offers warmth, personality, and a sense of place. The layout meanders gracefully, creating spaces that are both grand and intimate-perfect for gathering, entertaining, or retreating in peace. Yet it is the landscape, the gardens, the grounds, and the enchanting pool house-that truly make this property exceptional.Step outside and you are transported into a world of cultivated beauty and natural abundance. Rambling stone walls weave through vibrant perennial beds. Fruit trees and flowering borders dot the landscape. Every inch of the grounds has been lovingly considered, nurtured, and designed for those who cherish a connection to the earth. This is a haven for those who find joy in simply watching the seasons unfold.

381 Smith Hill Rd, Colebrook
$2,200,000
24113655 MLS
An exceptional opportunity to acquire a fully leased, income-generating commercial portfolio comprising 3 freestanding buildings This portfolio is anchored by well-established, long-term tenants including Webster Bank, KinderCare Daycare. Strategically positioned in high-visibility, high-traffic locations, the portfolio currently generates approximately $300,000 in gross annual income. This turnkey investment presents a rare opportunity to acquire a stable, diversified asset with immediate returns. This can also be purchased in a package with 430 Forbes Ave New Haven (24113698) which is a free standing building that is occupied by Citizens bank which is a long term tenant. It generates $68000 in gross income

70 Washington Ave, North Haven
$2,195,000
4 Beds ⋅ 5 Baths ⋅ 24156353 MLS
Private oasis in prime Washington location on dead end dirt road. Short walk to Johnson Farm Preserve - one of Steep Rock Land Trusts hidden gems. Long driveway leads to reimagined 1950's home on 13+ acres with views towards Nettleton Hollow, pool and brook. Vaulted public rooms surround fireplace with oversized plate windows to take in light and view. 3 bedrooms and 3.5 baths in main section of house including oversized primary suite. 4th ensuite bedroom has heated flooring and is full walk out on lower level providing separation for guests. 40' gunite pool with auto cover, back yard area fenced for pets. Multiple entertainment spaces off south side of house. Many mechanical upgrades, ample parking and automatic generator complete the package. Special opportunity to be in nature yet less than 5 minutes from Mayflower Inn & Spa. Fewer than 15 minutes to New Preston, Washington Depot or Woodbury for shopping, restaurants and services.

63 W Mountain Rd, Washington
$2,190,000
4 Beds ⋅ 4 Baths ⋅ 24153792 MLS
Possibly the most admired of the historic homes closeby to the storied Guilford Town Green and Jacobs Beach, the Captain Joel Stone House, c.1853 is now seeking a new owner. This remarkable grand Italianate Villa offers quite a pedigree having been built by a wealthy steamship owner, Joel Stone, son of the second lighthouse keeper of beloved Faulkner's Island. The quality of this gracious home with 6 fireplaces, a solid stone foundation and over 9' ceilings was an exception and curiosity when built and continues to impress today. 1st level: Parlor open to living room leading to formal dining room. Bedroom/den with expandable half bath, eat-in kitchen open to family/great room with fireplace. A generous open covered wrap around front porch for warm weather and private rear patio off the great room provide options for entertaining year round. 2nd level: Primary bedroom w/en-suite bath, two additional guest bedrooms, one with en-suite bath, plus third full hall- bath. Laundry area. 3rd level: a rooftop monitor (cupola or 'widow's watch') modeled after the lighthouse on Faulkner's Island. Carriage house- generous garage space on ground level (3 spaces). Private rear patio. 960 sf apartment on 2nd level includes bedroom, full bath, open concept living space with vaulted ceilings and exposed beams, full kitchen. Up a flight to a loft space. Sited on .77 acres with flowering specimen trees and gardens.

200 Whitfield St, Guilford
$2,190,000
5 Beds ⋅ 6 Baths ⋅ 24071624 MLS
Exceptional Washington Value. Wonderful Period Compound Replete with Main House, Guest House, Pool, Pond, Paddle Tennis & More! This Property Encompasses Both Sides of a Low-Traveled Town Road Merely 4 Min to the Village. 5 Bedroom, 3 Full & Two 1/2 Bath Main House + 2 Bedroom, 2 Bath Cottage + Heated Party/Sports Barn. A Terrific Floor-plan Includes: A Large Bright Eat-in Kitchen; Generous Living Room with Fireplace; A Cozy Den with Fireplace; True Primary Bedroom Suite with 1.5 Baths & Office/Sitt Room. Choice Neighborhood Dotted with Large Estates.

9 Mallory Brook Rd, Washington
$2,188,000
5 Beds ⋅ 7 Baths ⋅ 24150605 MLS
In the heart of Litchfield's coveted Historic District, along one of the town's most admired streets, stands the circa-1855 Woodruff House, an iconic Italianate Victorian Villa and enduring centerpiece of the neighborhood. Built for prominent Litchfield resident George Morris Woodruff, this beloved home blends architectural pedigree with modern livability. Signature elements include a shallow hipped roofline, distinctive columned verandah, double-tiered gallery, and dramatic two-story octagonal bays, a rare and remarkably preserved example of the period. Inside, grand yet inviting spaces unfold: formal entry hall, multiple living rooms for gathering and quiet retreat, dining room, den, office, and a spacious kitchen opening to a comfortable family room. The home offers five bedrooms including two primary suites, along with four full and three half baths, allowing guests and owners alike to live graciously. French doors lead to a sunroom and deck overlooking mature, landscaped grounds designed for entertaining with two patios, an updated heated pool, and the kind of setting that makes weekends linger longer. Modern comforts integrate seamlessly: elevator to primary bedroom, generator, four fireplaces and laundry room. A heated two-story barn provides flexible space for studio, workshop, or collector storage with room for two vehicles. Moments to the Litchfield Green. A rare opportunity to own not simply a home, but a recognized piece of Litchfield's architectural legacy.

44 South St, Litchfield
$2,185,000
4 Beds ⋅ 4 Baths ⋅ 24162180 MLS
NEW PRICE BELOW RECENT APPRAISAL. One house from L.I. Sound on a quiet Webster Point Road cul-de-sac, this 4000+ sf house delivers the ideal shoreline life: deeded beach access, multi-level panoramic water views, walkable distance to the Hammonasset Trail, and a spacious interior perfect for both large gatherings & cozy family life. A double-height foyer opens the house and leads into light-filled rooms with 10' ceilings & hardwood floors throughout the 1st level. The expansive LR is anchored by a handsome wood-burning FP and flows to a formal DR featuring intricate millwork from a historic mansion. The same heirloom millwork frames the dining area of the kitchen, which is fully-equipped to inspire the modern gourmet. The kitchen has access to a large porch perfect for summer entertaining & connects to a heated 2-car garage. Upstairs, the home offers a rare configuration: 2 primary suites - one on the 2nd floor, one on the 3rd - each with private decks to enjoy the water views that are unparalleled for area houses not directly waterfront. Two additional bedrooms on the 2nd floor share a hall bath & laundry room. The 3rd floor includes a finished den/office & storage. Deeded access to a low-tide beach and the sandy Pent Road beach offer endless opportunities to watch the sun rise or set, relax in the salty breeze, sea-fish, or take the canoe out. The bike-and-walking trail to Hammonasset State Park is at road's end.

64 Webster Point Rd, Madison
$2,176,300
4 Beds ⋅ 4 Baths ⋅ 24168973 MLS
HIGHEST and BEST DUE TUESDAY at 5 pm First time ever on market. This light-filled colonial sits high on a prime lot with views on beautiful Keelers Ridge. Custom-built by Kellogg Brothers, this home has 3 fireplaces and exceptional craftsmanship throughout. The property is open, sunny, and features a beautiful pool, outdoor living area, and expansive lawns. The expanded eat-in-kitchen has two islands, a 48" Thermadore gas range, double wall ovens,, and more cabinets than you will need. The kitchen is open to family room with fireplace and a sunroom with cathedral ceiling that opens to outdoor living area. The living room is comfortable, yet has a timeless elegance with fireplace, built-ins, beautiful windows and also opens to outdoor oasis. The dining room has floor to ceiling windows and a beautiful built-in. There is a paneled, tucked-away office with a new full bath and a rec room over the garage, in addition to a sunroom with new full bath convenient to the pool. Upstairs is a luxurious primary suite with spa bath, fireplace, and walk-in closet to relax in at the end of a long day. There are 3 more spacious bedrooms and an extra large hall bath. The lower level has 1500 sq ft that is easily finished. This elegant, comfortable home with a special backyard oasis is located close to Quarry Head Park with scenic hiking trails and a neighborhood great for walking, biking, running, and socializing. This home has it all. You will love living here!

45 Keelers Ridge Rd, Wilton
$2,175,000
4 Beds ⋅ 4 Baths ⋅ 24178830 MLS ⋅ Noroton Green BLDG.
Welcome to 333 West Avenue, a stunning residence nestled within the Noroton Green Association-a boutique enclave of just six homes. Built in 2012 by the renowned Hertz Construction, this home is a harmonious blend of timeless craftsmanship and modern luxury. From the moment you step inside, you'll be captivated by the soaring ceilings, intricate millwork, and custom built-ins that frame the inviting living spaces. A cozy fireplace anchors the main living area, while the chef's kitchen steals the show with its high-end white cabinets, Thermador appliances, gleaming finishes, and thoughtful design. The home boasts four generously sized bedrooms, including a show stopping primary suite with a spa-like marble bath, a freestanding soaking tub, and an enviable walk-in closet. Three additional bedrooms, 3.5 baths, including a third-floor retreat with an extra bedroom and living space provide ample room for family and guests, office space or additional living space. Enjoy the ease of maintenance-free living with HOA-covered perks, leaving you more time to enjoy life. A spacious two-car garage adds convenience, and the location is second to none-stroll along sidewalks to the train station, Darien Commons, and Heights Crossing. This is more than a home; it's a lifestyle.

333 W Ave Unit 6, Darien
$2,175,000
4 Beds ⋅ 4 Baths ⋅ 24169066 MLS
It's the stillness of the marsh..calm, quiet and ever-changing. This home captures nearly 270 degrees of protected landscape and water views, making the setting feel peaceful, immersive and incredibly rare. Inside, every detail feels thoughtful and intentional. Sunlight pours in and each space was designed to stay connected to the beauty beyond. The main living area rises to an 18-foot cathedral ceiling, anchored by a fireplace and surrounded by windows. Thoughtful details such as coffered ceilings and custom millwork enhance the home's architectural appeal throughout. The kitchen is both functional and striking, featuring a gas Wolf range, Sub-Zero refrigerator, additional wall oven, marble countertops and an expansive island workspace, all while maintaining a clean and refined feel. It opens naturally to the main gathering areas, making everyday living and entertaining effortless. The first-floor primary suite offers a private retreat with a fireplace, spa-like bath and a generous walk-in closet. Upstairs, three additional bedrooms are positioned to capture light and those same sweeping marsh views. Step outside and the connection deepens. An expansive deck overlooks the marsh, while a beautifully designed patio with a built-in fireplace creates the perfect setting. And when you want to get out on the water, river access is right there. A setting that feels distinctly its own, yet remains effortlessly connected to Madison's village and beaches and Shoreline lifestyle.

101 Garnet Park Rd, Madison

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