Refine Search
Sort by
210 Doolittle Dr, Norfolk
$4,200,000
6 Beds ⋅ 8 Baths ⋅ 24192442 MLS
Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensuite bedrooms with fireplaces, and a playroom. A private ensuite studio bedroom sits above the heated three-car garage, offering perfect accommodations for staff or guests.

210 Doolittle Dr, Norfolk

760 Valley Rd, New Canaan
$4,200,000
6 Beds ⋅ 8 Baths ⋅ 24116481 MLS
A Historic Masterpiece, Reimagined for Modern Living Originally crafted in 1931 by renowned architect Frazier Forman Peters, this iconic stone residence has been completely reinvented-expanded, redesigned, and redefined for today's luxury lifestyle. The newly completed home now offers over 9,000 square feet of exquisite living space with 6 bedrooms, 7.5 baths, and every modern comfort imaginable, all while preserving the timeless character of its hand-cut fieldstone construction. Inside, soaring ceilings, a dramatic double staircase, and elegant living and dining spaces create a perfect blend of grandeur and warmth. Five fireplaces anchor inviting gathering areas, while French doors lead to light-filled suites and sweeping terraces overlooking the serene landscape. From its architectural heritage to its meticulous, top-to-bottom reinvention, this residence stands as a true work of art-a rare fusion of history, craftsmanship, and modern sophistication-just minutes from downtown New Canaan. SQ FT REFLECTS TO BE BUILT RENDERINGS 9000 SQ FT+-

760 Valley Rd, New Canaan

15 Courageous Circle, Bristol
$4,199,000
5 Beds ⋅ 5 Baths ⋅ 1406202 MLS
15 Courageous Circle Poppasquash Point 5 BR | 4 BA | Deeded Water Access THE SETTING Tucked within the private coastal enclave of Poppasquash Point, this five-bedroom residence comes with deeded access to Narragansett Bay a genuine rarity on the peninsula. Westerly exposures mean the water views are at their most spectacular late in the day, when the bay turns gold. THE INTERIOR Inside, the home is bright and generously scaled a gourmet kitchen, formal dining room, and multiple living areas flow naturally for both quiet family evenings and larger gatherings. Rich architectural details give the rooms character without feeling heavy. The wraparound porches extend the living space outdoors and frame serene water vistas on multiple sides. THE PRIMARY SUITE Upstairs, the primary suite is the clear standout: a newly renovated spa-like bath, walk-in closet, and a private balcony positioned to catch the bay breezes and those westerly sunsets. Four additional bedrooms including one en-suite accommodate family and guests comfortably. ALSO WORTH NOTING A detached three-car garage provides ample storage for boats and beach gear practical at a waterfront property. The grounds are beautifully landscaped and maintain the home's sense of privacy. A rare opportunity to enjoy privacy, elegance, and a coastal lifestyle. Watch the sun set over Narragansett Bay from your own wraparound porch every evening. Please view the video of this amazing property.

15 Courageous Circle, Bristol

20 Marianne Rd, Darien
$4,199,000
5 Beds ⋅ 8 Baths ⋅ 24082353 MLS
New construction from foundation up and ready for 2026! On a coveted Darien cul-de-sac, this modern colonial boasts 6500sf of elegance and comfort. Step through the welcoming foyer, complete with a coat room and powder room, and into a spacious, light-flooded living room, perfect for gatherings that stretch into the evening. The custom kitchen is a true centerpiece, with a grand stone island, Thermador appliances, an oversized range, and abundant cabinetry. Surrounded by windows, the sunlit breakfast room flows effortlessly to the kitchen/great room, where a gas fireplace and beamed ceiling create warmth and character and flow out to an huge deck overlooking 1.2 private acres. A first-floor office with full bath offers flexibility for work, guests, or a quiet retreat. Everyday ease continues with a mudroom, half bath with stunning, floating quartz vanity, and an attached two-car garage. Upstairs, the primary suite is a serene escape with vaulted ceilings, a walk-in closet, and a private balcony overlooking the lush and private yard. Three additional en-suite bedrooms each feature custom walk-in closets, blending function with elegance. The partially finished third floor and lower level invite endless possibilities - a home gym, playroom, creative spaces, etc. This home has privacy and space for all and is only minutes from town, shops, the beach, golf, the train and all amenities. A new home for the new year!

20 Marianne Rd, Darien

5 Hunter St, Greenwich
$4,195,000
6 Beds ⋅ 7 Baths ⋅ 24207811 MLS
Introducing a newly constructed Contemporary Colonial, by Alfieri Enterprises, that captures the essence of Old Greenwich living offering a seamless blend of classic architecture and modern design on a quiet cul-de-sac near schools, shops and the train. Defined by extraordinary craftsmanship, custom details and curated finishes in a stunning 6,000 sq. ft. home. Great for entertaining in open plan chef's kitchen, breakfast room with doors to expansive deck, family room and main level en-suite bedroom/office. Upstairs boasts an enviable primary suite retreat with spa bath, custom walk-in closets, an additional en-suite bedroom and two bedrooms connected by Jack/Jill bath. Top floor media/rec room and a guest en-suite bedroom, and the lower level offers a flex space for gym/gaming, half bath and storage complete this offering. With possible pool site.

5 Hunter St, Greenwich

22 Fillow St, Westport
$4,050,000
5 Beds ⋅ 8 Baths ⋅ 24215100 MLS
NEW CONSTRUCTION BY RENOWNED WESTPORT LUXURY BUILDER WALTER MATTERA IN THE CHERISHED FLOWER ESTATES NEIGHBORHOOD! An exceptional opportunity to own a brand-new 5-bedroom, 6-full and 2-half-bath luxury residence by Mattera Construction, one of Westport's premier luxury homebuilders, celebrated for timeless architecture, exceptional craftsmanship, and meticulous attention to detail. Set on a beautiful .40-acre property in Westport's desirable Downtown North neighborhood, 22 Fillow Street offers the rare combination of luxury new construction and the warmth and character of an established in-town community. Flower Estates is one of Westport's most cherished neighborhoods, where tree-lined streets, a welcoming atmosphere, and a genuine sense of community create an increasingly sought-after lifestyle. Just minutes from downtown Westport's shops and restaurants, approximately 10 minutes from the Westport train station and Compo Beach, and close to Coleytown Elementary School, the location offers convenience without sacrificing neighborhood charm. Walter Mattera brings his signature commitment to quality, architectural integrity, and thoughtful design to this exciting new residence. With construction just underway, this is a rare opportunity to own a beautifully crafted luxury home by one of Westport's most respected builders in a neighborhood where new construction opportunities are increasingly limited. Timeless craftsmanship. Exceptional location. The best of Westport living.

22 Fillow St, Westport

14 Shoreham Club Rd, Greenwich
$4,000,000
4 Beds ⋅ 3 Baths ⋅ 24205297 MLS
A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The .28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large communal waterfront lawn. The current home features a large living room with direct Sound views, a formal dining room, a kitchen and family room opening to a stone patio facing Long Island Sound, and a primary bedroom suite with private bath. Three additional bedrooms and full bath occupy the upper level, sharing the same water views. Gas heating, central air conditioning and an attached 2-car garage are in place. A beautiful and serene location in a private waterfront association, Long Island Sound views and steps to Tod's Point - all within minutes of the Old Greenwich train station, Old Greenwich shops and dining and schools.

14 Shoreham Club Rd, Greenwich

46 Statue Way, Portsmouth
$4,000,000
1419880 MLS
Rare 11-unit condominium rental portfolio in Portsmouth's Lehigh Hill area, minutes from Newport. Current rents of $325,920/year sit ~28% below market ($417,600) about $91,680 in upside as leases turn, moving the cap rate from 6.05% to 8.34% and GRM from 12.27x to 9.58x at $4,000,000. Bonus upside: Unit #46's detached garage is ADU-conversion ready under RI's statewide ADU law, and the oversized R-20 parcel may support further density. Condo structure lets a buyer hold as a rental or sell buildings/units individually at retail pricing rare flexibility for this asset size. Built 1986, condo-converted 2004; 8 townhouse buildings, most with decks, in-unit laundry, garage parking. Solar covers electric for 7 of 8 buildings; tenants pay own water; no flood insurance required. NOI: $242,035 in-place to $333,715 at market on $83,885 expenses. Cash flow, upside, development potential, and disposition flexibility in one of RI's most desirable coastal submarkets.

46 Statue Way, Portsmouth

464 Black Point Lane, Portsmouth
$4,000,000
3 Beds ⋅ 6 Baths ⋅ 1420461 MLS
Privately set within Black Point, one of Portsmouth's most desirable coastal neighborhoods off Indian Avenue, this distinctive custom home offers water views, exceptional privacy and resort-style outdoor living. With almost 5,000 sf across three levels, the residence combines substantial scale with a warm, relaxed character. The dramatic great room features a cathedral ceiling, exposed beams, skylights, reclaimed barn wood floors and handsome stone fireplace, flowing naturally to the dining area and spacious kitchen with oversized island. An expansive deck captures water views, while a three-season sunroom offers another inviting place to gather. The generous first-floor primary suite features a fireplace, skylights, ample closets and private bath. Upstairs are two bedrooms, an en-suite flexible bonus space and balconies with water views. The walkout lower level, with kitchen, living area, bonus room and baths, offers excellent flexibility for guests or extended family and convenient pool access. Outside, extensive landscaping surrounds a 40' x 21' saltwater pool, hot tub, cabana and outdoor shower, creating a private setting for summer entertaining. A two-bay garage, metal roof, generator, custom-fitted closets and abundant storage underscore the home's thoughtful design. Minutes from Newport and Middletown beaches, this meticulously maintained residence offers a compelling blend of privacy, water views and relaxed coastal living.

464 Black Point Lane, Portsmouth

31a June Rd, Washington
$4,000,000
4 Beds ⋅ 4 Baths ⋅ 24182872 MLS
This exquisite Frank Lloyd Wright Usonian-inspired lakefront home offers a rare opportunity on the serene shores of Lake Waramaug. Known for its pristine waters, natural beauty, and timeless appeal, Lake Waramaug is one of Connecticut's most beautiful and well-preserved natural lakes. Set in the charming village of New Preston, the to-be-built residence is presented by Viridian Custom Homes and Lindal Cedar Homes, with a masterful design by Aris Georges, a leading authority on Frank Lloyd Wright's design principles. Finishes by Kathleen Goodwin Interiors reflect a sophisticated blend of Connecticut and New York City design sensibilities. This 4-bedroom, 3.5-bath, 3,285 SF home features airy rooms, dramatic ceiling heights, organic materials, broad roof overhangs, abundant natural light, and a seamless connection to the land. Set on 1.85 acres with 500 ft of private waterfront and dock rights, the property offers spectacular westerly views. A rare opportunity to create a modern lakefront retreat that blends architectural elegance, natural beauty, and timeless Wright-inspired design.

31a June Rd, Washington

21 School Rd, Wilton
$3,999,999
6 Beds ⋅ 7 Baths ⋅ 24212467 MLS
Welcome to an unparalleled masterpiece of living, nestled within a completely fenced, four-plus-acre private paradise in the very heart of Wilton, Connecticut. This extraordinary estate perfectly balances absolute serene privacy with the effortless convenience of town life. Approached via double-gated entries, the winding driveway unveils a residence meticulously crafted for the epicurean, the entertainer, and the modern visionary. The heart of the home centers around a true chef's kitchen, anchored by a roaring fireplace that radiates warmth and timeless character. Designed for both casual mornings and grand-scale catering, it features premium commercial appliances, a designated coffee bar room for your morning rituals, and endless custom storage to keep the aesthetic flawless. Just off the kitchen, a walk-in wine room awaits your private collection. For seamless entertaining, the formal sitting room features a fully equipped walk-in bar, transitioning beautifully into a stunning screened-in porch and a massive outside deck overlooking the grounds. Offering a total of six luxurious bedrooms, the home's layout is brilliantly engineered for ultimate privacy. The Owner's Suite and Family Quarters are situated in the main expanse of the home, offering opulent retreats with peaceful views of the estate.

21 School Rd, Wilton

62 Codfish Hill Rd, Bethel
$3,999,999
6 Beds ⋅ 4 Baths ⋅ 24128777 MLS
Subdivision Potential! One of the Largest Land Parcels in Bethel - Over 61 Acres! A rare opportunity for investors, developers, and visionaries to own more than 61 acres in the highly sought-after Codfish Hill area. This former farmland, once a thriving homestead, offers a unique combination of development potential and the charm of an existing colonial farmhouse with multiple outbuildings. The property includes an oversized 3-bay garage/barn with a full second level, and a nearly 4,500 sq. ft. farmhouse filled with character and possibility. Inside, you'll find a grand great room with a soaring floor-to-ceiling stone fireplace featuring French doors leading to an expansive deck-perfect for entertaining. The home features 5 bedrooms (potentially 6), 3.5 baths, and 3 stone fireplaces, including a first-floor primary suite with separate office/nursery, its own fireplace and spa-like bath, plus a walk-out lower-level in-law suite with private entrance, stone fireplace, and separate laundry hookups. This is truly a diamond in the rough-whether you're looking to restore the farmhouse to its former glory or envisioning a subdivision project on one of the largest parcels left in Bethel. Opportunities like this are few and far between-don't miss it! Buyer use due diligence in possible subdivision and zoning requirements per town of Bethel. Property is part of an estate and sold as-is and subject to probate approval.

62 Codfish Hill Rd, Bethel

1 Great Elm Dr, Sharon
$3,999,000
6 Beds ⋅ 9 Baths ⋅ 24206049 MLS ⋅ Great Elm BLDG.
This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

1 Great Elm Dr, Sharon

4 Jones Circle, Barrington
$3,999,000
4 Beds ⋅ 8 Baths ⋅ 1415622 MLS
Set within Barrington's prestigious Rumstick/Nayatt enclave, this exceptional estate occupies the former Karl Jones Rose Gardens surrounded by mature specimen plantings & meticulously designed grounds offering sweeping sunset views & remarkable privacy in one of Rhode Island's most coveted coastal neighborhoods. Featured in Rhode Island Monthly, the residence was custom designed by a renowned architect, builder & design team showcasing exceptional craftsmanship, bespoke millwork, custom cabinetry, artisan lighting & refined finishes throughout. A grand foyer with sweeping staircase and domed ceiling sets the tone for elegant yet comfortable living. The custom Justras Woodworking kitchen features premium appliances, white and mahogany cabinetry, an expansive center island and fully appointed butler's pantry flowing seamlessly into light filled living and entertaining spaces. The primary suite serves as a private sanctuary with a fireplace, sitting room, library/office, custom dressing room & spa inspired bath! Additional ensuite bedrooms provide comfort and privacy for family/guests. The lower level includes a fitness center, theater/multipurpose room, salon, full bath & extensive storage. Stone terraces and garden pathways lead to a resort style heated pool and spa completed by a fully equipped pool house with kitchen and bath. Combining architectural distinction, timeless materials and impeccable execution, this is one of Barrington's most exceptional private estates!

4 Jones Circle, Barrington

1 Great Elm Dr, Sharon
$3,999,000
6 Beds ⋅ 9 Baths ⋅ 24173869 MLS
This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

1 Great Elm Dr, Sharon

206 Oakland St, Manchester
$3,998,000
24194713 MLS
Manchester market currently running over 65% of inventory UNDER DEPOSIT. This PROJECT is ready to BUILD! 100% site plan approved. PROJECT COULD BE SPLIT INTO SMALLER PHASES - 3 of 50U or 5 of 30U PER PHASE. With very little housing options, high buyer demand for home ownership, and potential rates dropping this could be a very lucrative opportunity. This property is approved for a 148 unit townhome/condo project. 45-2 Bed units, 90-3 Bed units, and 13 4 Bed units. The location could not be better! This to be built complex is situated on Union pond with walking trails along the water and connecting to the park. Situated set back off the road, but still within quick access to highway, Buckland hills mall, Evergreen Walk, and all major amenities. A project of this size does not come up very often especially with this little inventory! Agent- owner

206 Oakland St, Manchester

74 Long Neck Point Rd, Darien
$3,995,000
6 Beds ⋅ 8 Baths ⋅ 24209556 MLS
Opportunities to build fresh on Long Neck Point are vanishingly rare, making this lush, one-acre parcel a true crown jewel in Darien's most prestigious enclave. This isn't just a piece of land; it's a seamless path to an extraordinary lifestyle. If you've been dreaming of a bespoke estate but dread the years of red tape, your solution has arrived. The property comes with preapproved architectural plans for a stunning Center Hall Colonial. The design features 7,500 square feet of sophisticated living space across the first and second floors alone, with additional square footage thoughtfully planned for both the third floor and the expansive basement level. Imagine sweeping interiors and a layout that flows effortlessly from one sun-drenched room to the next. With all permits in place and a premier builder ready to break ground, you can bypass the typical delays and start construction immediately. The lot itself is absolutely gorgeous, offering a level, expansive canvas that invites creative landscape design. Elevating this opportunity even further is the exclusive inclusion of waterfront access. A shared dock is currently being built for the four properties in this enclave, reachable via a dedicated pathway that leads directly to the water at Pear Tree Point Road. It is the ultimate amenity for those who wish to embrace the coastal lifestyle. This is a rare invitation to secure a foothold in a legendary location without the wait.

74 Long Neck Point Rd, Darien

290 Off Spring Street, Block Island
$3,995,000
5 Beds ⋅ 5 Baths ⋅ 1424926 MLS
Coastal Beauty, thoughtful design and the ease of island living come together in this exciting offering. Set on 0.87 acres in a quiet neighborhood 1 mile from Old Harbor, this property offers stunning water views East to the Atlantic Ocean and North along the coast. Completed less than 10 years ago, the 3 Bedroom, 3.5 bath main home features a coastal elegant design with light hardwood floors, shiplap walls, stainless steel appliances and a dramatic vaulted ceiling created by South County Post & Beam. The thoughtful layout places the bedrooms on the first floor and living spaces above, maximizing an elevated vantage point to take in the surrounding water views. Step out to the recently expanded second floor deck where morning coffee, summer dinners and evenings under the stars become part of everyday life. A separate 2 BR, 1 bath guest cottage with loft adds versatility for visiting family and friends. The open, useful and level lawn provides space to enjoy the outdoors and includes a deeded pathway leading you down a charming path to the top of the bluff, where you can sit and enjoy the natural beauty of the island or continue down to Pebbly Beach and the ocean. Whether envisioned as a summer escape, a gathering place for generations or a fantastic rental property, this is an opportunity to create lasting memories and enjoy all that Block Island has to offer. This home is offered beautifully furnished and turnkey. Simply gather your favorite people begin creating memories!

290 Off Spring Street, Block Island

74 Long Neck Point Rd, Darien
$3,995,000
24209317 MLS
Opportunities to build fresh on Long Neck Point are vanishingly rare, making this lush, one-acre parcel a true crown jewel in Darien's most prestigious enclave. This isn't just a piece of land; it's a seamless path to an extraordinary lifestyle. If you've been dreaming of a bespoke estate but dread the years of red tape, your solution has arrived. The property comes with preapproved architectural plans for a stunning Center Hall Colonial. The design features 7,500 square feet of sophisticated living space across the first and second floors alone, with additional square footage thoughtfully planned for both the third floor and the expansive basement level. Imagine sweeping interiors and a layout that flows effortlessly from one sun-drenched room to the next. With all permits in place and a premier builder ready to break ground, you can bypass the typical delays and start construction immediately. The lot itself is absolutely gorgeous, offering a level, expansive canvas that invites creative landscape design. Elevating this opportunity even further is the exclusive inclusion of waterfront access. A shared dock is currently being built for the four properties in this enclave, reachable via a dedicated pathway that leads directly to the water at Pear Tree Point Road. It is the ultimate amenity for those who wish to embrace the coastal lifestyle. This is a rare invitation to secure a foothold in a legendary location without the wait.

74 Long Neck Point Rd, Darien

51 Briscoe Rd, New Canaan
$3,995,000
5 Beds ⋅ 7 Baths ⋅ 24207397 MLS
Set high 4.5 + private acres, this impressive six-bedroom home offers space, privacy and resort-style amenities, with beautiful views from its elevated setting. Designed for both everyday living and entertaining, the home features four finished levels with flexible spaces for family, guests, work and recreation. Generously proportioned living areas flow throughout the main level, with an expansive property and outdoor entertaining spaces. The bedroom accommodations are exceptionally versatile. In addition to the main bedroom level, a private bedroom and full bath above the three-car garage creates an ideal guest, au pair or extended-family suite. A fully finished walk-up third floor provides additional space for a home office, playroom, studio or recreation area. The finished walk-out lower level adds yet another dimension to the home, with a bedroom, full bath, wine cellar and direct access to a screened porch and the grounds beyond. Outside, the property becomes a private retreat. A free-form swimming pool, expansive garden and tennis court are surrounded by 4.5+ acres of beautiful grounds, while the home's hilltop position captures views and light from morning through evening. With six bedrooms, four finished levels, a three-car garage, pool, tennis court and an extraordinary elevated setting, this is a home that offers exceptional space and the opportunity to enjoy a true country lifestyle.

51 Briscoe Rd, New Canaan

14 Kay Boulevard, Middletown
$3,995,000
7 Beds ⋅ 8 Baths ⋅ 1422195 MLS
A rare multigenerational estate minutes from beautiful beaches and Downtown Newport, designed to bring generations together in style. The main residence offers 6 bedrooms, 6.5 bathrooms, two expansive living rooms, a private office and a first floor suite, while a legal one-bedroom, 1 bathroom apartment above the heated two-car garage is ideal for extended family or guests. The chef's kitchen flows effortlessly out to the spacious mahogany deck, patio, outdoor kitchen, pool, hot tub and yard, making everyday living and grand scale entertaining feel easy. Custom millwork, coffered ceilings, gas fireplaces and refined finishes create warmth and timeless sophistication throughout. Upstairs, the primary suite is a private retreat with dual vanities, an oversized shower, soaking tub and dressing room. Integrated Sonos audio and a custom outdoor display keep the energy flowing from room to room and into the outdoor living spaces, while Lutron lighting and custom window treatments create the perfect ambiance at a touch. Professional landscaping, cobblestone edging and new fencing frame a private resort setting, where app controlled pool and spa systems make relaxation effortless. A whole home generator, hardwired security and basement waterproofing systems provide year round comfort and confidence. With Middletown resident beach privileges and Newport moments away, this is more than a home, it is a private family compound created for effortless living and unforgettable gatherings.

14 Kay Boulevard, Middletown

39 Chippechaug Trl, Stonington
$3,995,000
4 Beds ⋅ 5 Baths ⋅ 24172306 MLS
A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area's most coveted waterfront settings. Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape. Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline. A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic's acclaimed restaurants, boutiques, marinas and waterfront attractions.

39 Chippechaug Trl, Stonington

405 Whitfield St Unit 2, Guilford
$3,995,000
6 Beds ⋅ 6 Baths ⋅ 24138935 MLS ⋅ Eagleview Condominiums BLDG.
Eagleview at Guilford - Where Luxury Meets Lifestyle. Discover Guilford's newest luxury coastal condominium community, where superior craftsmanship, modern design, and breathtaking views of Long Island Sound redefine Connecticut shoreline living. Whether you're enjoying a sunset from your private balcony, entertaining in your chef's kitchen, or exploring Guilford's vibrant coastal village, Eagleview is more than a home, it's a lifestyle. Experience 6,200 SF of refined living space (expandable to over 8,000 SF) perfectly positioned to capture the tranquil salt marshes and shimmering expanse of Long Island Sound. Each residence includes multiple private balconies that invite you to relax and savor the natural beauty that surrounds you. Unmatched craftsmanship & comfort, this community of only 11 luxury units blends architectural excellence with everyday ease. Every residence features 10-foot ceilings, custom crown moldings, and a Chef's Dream Kitchen equipped with professional-grade appliances and elegant finishes designed for both function and style. Modern conveniences include private elevators, heated 4-car garages with EV charging stations, central air, central vacuum systems, and backup generators. Flexible open floor plans allow you to create spaces that reflect your personal lifestyle and vision. Ideally situated just a 1/2 mile stroll to Jacob's Beach and the Guilford Green, Eagleview offers easy access to an array of restaurants, boutique shopping, and cafes.

405 Whitfield St Unit 2, Guilford

1097 Eddie Dowling Highway, North Smithfield
$3,990,000
1416332 MLS
RARE AUTO COMPOUND | ROUTE 146 | 5.25 ACRES | 4 LOTS | CURRENT OWNER RELOCATING 4115 MENDON RD, CUMBERLAND An exceptional and rarely available commercial opportunity located directly on Route 146. This one-of-a-kind 5.25-acre auto compound consisting of four individual lots is perfectly suited for a car dealership, auto body, or auto repair operation. The primary 7,350 sq. ft. building features an 8-bay service garage, showroom, office space, and 3 bathrooms. The compound also includes a 5-bay service garage with a 2-bedroom apartment, an updated 3-bedroom single-family home, and included within the 5.25 acres sits a 1.22-acre lot for expansion or parking. Infrastructure, space, and location all in one properties like this don't come twice.

1097 Eddie Dowling Highway, North Smithfield

423 Main St, Middletown
$3,990,000
4 Baths ⋅ 24182009 MLS
Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.

423 Main St, Middletown

415 Old Post Rd, Fairfield
$3,975,000
5 Beds ⋅ 5 Baths ⋅ 24206348 MLS
Over an acre to yourself. The best of Fairfield within reach. In the heart of downtown Fairfield and the beach area, 415 Old Post Road offers something almost impossible to find: land and privacy to create a generational estate, with the life of a coastal town just beyond your gate. Only a handful of properties in the Sherman School district offer this. Fewer still could tell this story. The family who built this Italianate Victorian stayed for more than a century. Stand beneath its soaring ceilings, admire the craftsmanship, then step onto the screened-in porch. You begin to understand. Trees surround you. Church bells carry through the air. It feels like your own park. Yet the beach, schools, restaurants, shops and train are all within walking distance. For the current owners, that has meant children walking home from school with friends. Thanksgiving dinners for twenty. Additional bedroom options for overnight guests. Winter evenings around the parlor fire. A front porch filled with friends as the Memorial Day parade passes by. There is room here for the life you have imagined. Explore the possibilities for a pool, tennis court and gardens. Create a place where everyone gathers now-and where the next generation will want to return. Historic architecture. Meticulously maintained, thoughtfully updated and in pristine condition. A once-in-a-lifetime opportunity. Come discover what makes this place so hard to leave-and imagine what the next 50 years could look like.

415 Old Post Rd, Fairfield

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

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!