Chris Simms Lists a Restored Antique Farmhouse Estate in Greenwich for $8M

Chris Simms is trading in Greenwich for a new chapter out of state, and with that comes a freshly listed $8 million estate at 640 Round Hill Road that reads like the town’s greatest hits: historic bones, modern polish, and enough land to make the word “acreage” feel like an understatement. The fully restored antique farmhouse spans approximately 3,669 square feet on about 4.01 level acres, with sweeping meadow views and a true country setting directly across from protected conservation land—with immediate access to the Greenwich Riding Trails.

Inside, the house keeps its character front and center—wide-plank antique floors, exposed beams, preserved fireplaces, and original details—while a design-forward renovation brings the comfort up to modern luxury standards. The newly created primary suite is positioned as a standout: cathedral ceilings, a dramatic wall of floor-to-ceiling windows with electric shades, a bespoke dressing room with custom cabinetry, and a private staircase up to a light-filled office that feels like its own retreat.

The layout is built for both everyday living and entertaining, with six bedrooms and five full baths, plus a beautifully finished lower level featuring a substantial recreation room with a fireplace, an additional bedroom, a full bath, and direct exterior access. Outdoors, the property leans into its “host and unwind” potential with a historic party barn and a pool house with a kitchenette—spaces that make holiday weekends and summer nights feel automatic rather than aspirational.

For equestrian buyers (or anyone who just wants that Greenwich lifestyle without needing a second property), the setting is as functional as it is picturesque: three horse stalls with a tack room, plus three paddocks. The Simms put it simply: “Being the steward of this remarkable home and property has been a true privilege. Our family has shared so many unforgettable moments here, from leisurely trail rides with our horses throughout the neighborhood to enchanting holiday celebrations in the historic barn.” Monica Webster of Douglas Elliman holds the listing.

---

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

Brown Harris Stevens Connecticut Partners to Support Local Families in Need This Holiday Season

Courtesy of Brown Harris Stevens

This holiday season, Brown Harris Stevens Connecticut is bringing the community together to support local children and families in need. Partnering with the New Canaan Chamber of Commerce and the non-profit organization Person-To-Person, the real estate firm is participating in two heartwarming initiatives aimed at spreading joy and providing essential resources across Fairfield County.

For the New Canaan Gingerbread House Tour, now in its 20th year, Brown Harris Stevens staff and agents have purchased 150 gingerbread house kits from Walter Stewarts Market. Distributed through the New Canaan Chamber of Commerce, these kits are decorated by children during the Thanksgiving holiday and displayed in local storefronts from December 6 to December 22 as part of the Holiday Stroll. This beloved tradition, made possible by community collaboration, adds a festive charm to the season while bringing smiles to young faces.

Courtesy of Brown Harris Stevens

The partnership extends beyond seasonal festivities with a meaningful Food Drive to benefit Person-To-Person, a non-profit dedicated to supporting Fairfield County residents with essential resources like food pantries, clothing centers, and emergency financial assistance. Donation bins have been placed at all six Brown Harris Stevens Connecticut storefronts, providing an easy way for the community to contribute to families in need.

Courtesy of Brown Harris Stevens

“We are delighted to partner each year with these incredible organizations that inspire the holiday spirit,” said Christopher Halstead, Executive Sales Director for Brown Harris Stevens Connecticut. “Our real estate professionals are proud of our long-standing commitment to helping families in the communities where we live and work.”

With their focus on giving back to the community, Brown Harris Stevens invites everyone to join in spreading kindness and making a difference this holiday season.

---

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

Historic Elegance Meets Modern Luxury: Inside Huguette Clark's Reimagined New Canaan Estate

The former estate of the enigmatic copper heiress Huguette Clark has undergone a stunning transformation, blending its rich historical charm with cutting-edge modern luxury. Listed at $25.5 million, this 52-acre New Canaan property at 104 Dans Highway offers an extraordinary opportunity to own a piece of history, now reimagined for a new era of opulence.

James Gagliardi of Modern Media

A Storied Past Built in 1937, the grand French-style manor was purchased by Huguette Clark in 1951, but it remained empty for over six decades while Clark lived in seclusion in a Manhattan hospital. Upon her death at 104 in 2011, the estate continued to sit untouched, furthering its mystery and allure. Now, after being meticulously restored by renowned fashion designer Reed Krakoff and interior designer Delphine Krakoff, the property has been given a new life while paying homage to its storied past.

James Gagliardi of Modern Media

Bespoke Restoration Reed and Delphine Krakoff have infused the mansion with bespoke finishes and modern comforts while maintaining the essence of its original design. The property, known as "Le Beau Chateau," showcases a seamless blend of history and innovation, with elegant interiors that capture the timeless luxury of a bygone era. The estate includes sprawling meadows, tranquil streams, wildflower gardens, and carefully restored architecture that evokes a sense of grandeur and grace.

James Gagliardi of Modern Media

A Luxurious Oasis The estate's grounds have been masterfully enhanced to include a stunning pool, tennis court, and beautifully landscaped gardens. Additionally, two charming cottages—one for caretakers and one as an exercise pavilion—add to the property's appeal, offering a private, resort-like experience. Surrounded by lush woodlands and open space, Le Beau Chateau is an oasis of peace and luxury, tucked away in Fairfield County’s serene countryside.

James Gagliardi of Modern Media

For those looking to own a home that is as rich in history as it is in modern elegance, 104 Dans Highway is a rare gem that offers the perfect blend of past and present, ready to be enjoyed for generations to come.

---

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

A Modern Gem: Inside John Howe’s Organic Mid-Century Modern Home in New Canaan

Experience the magic of organic architecture with the recently listed masterpiece at 22 Father Peters Lane in New Canaan, CT. Priced at $3,995,000, this architectural gem, designed by John Howe, an apprentice of the legendary Frank Lloyd Wright, seamlessly integrates modern living with the natural world.

Built in 1981, this home is a prime example of organic mid-century modern architecture, embracing natural shapes and the surrounding environment to create a harmonious living space. John Howe, who worked with Wright for 27 years as his chief draftsman, infused his own design philosophy into the property, emphasizing open spaces, floor-to-ceiling windows, and a minimal footprint. The result is a stunning residence that distinguishes itself from traditional mid-century modern homes, which often focus more on lines and sharp angles.

Set on nearly 7 acres at the end of a private cul-de-sac, this sprawling 7,000 square-foot estate offers luxurious living spaces designed for both grand entertainment and everyday comfort. Upon entering, you are greeted by a grand dining room with double sliding glass doors that open to a Japanese garden and a stone patio with a fire pit, creating an inviting space for gatherings. The living room, featuring grand hemisphere glass windows, frames serene views of the surrounding trees and nature, complemented by exquisite stained glass accents that add color and warmth to the room.

The primary bedroom is a true sanctuary, complete with a private patio overlooking the picturesque backyard. The en-suite bathroom offers luxurious amenities, including a soaking tub and a spa-like shower, providing a perfect retreat after a long day. Additional highlights on the main floor include two bedrooms, two laundry rooms, and a soundproof studio, ideal for creative pursuits or working from home.

Upstairs, the loft area features an office and a sitting room, providing an ideal sanctuary for relaxation and unwinding. The second floor also offers an expansive family room perfect for gatherings and a guest suite that ensures privacy and comfort for visitors. With its convenient location to Scott's Corner and downtown New Canaan, this meticulously maintained home achieves a perfect balance of design, tranquility, and convenience.

This home is not just a place to live but a testament to the enduring legacy of Frank Lloyd Wright and the talent of John Howe. It offers a unique opportunity to own a piece of architectural history while enjoying the modern comforts and luxuries of today.

Chau Ngo of The Jennifer Leahy Team at Douglas Elliman is the listing agent.

---

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

Brown Harris Stevens Unveils MORE Network: A New Era in Real Estate Storytelling

In a bold move that redefines real estate marketing, Brown Harris Stevens (BHS), a leader in the luxury real estate sector, has launched the Mastery of Real Estate Network (MORE Network). This innovative multimedia platform, featuring dedicated channels on Apple Podcasts and YouTube, showcases the expertise and insights of BHS agents from across the country. Produced and edited by the BHS creative team, MORE Network is set to captivate audiences with its unique blend of informative and entertaining content.

Brown Harris Stevens, synonymous with luxury real estate, has taken a significant leap into the digital age with the launch of its Mastery of Real Estate Network, or MORE Network. This new multimedia platform is a testament to BHS's commitment to innovation and client engagement in an evolving media landscape.

Matthew Leone, Chief Marketing Officer at BHS, highlights the vision behind MORE Network: “As traditional media outlets continue to evolve, it became essential for us to create our own media channel. MORE Network is our answer to this challenge, offering a dynamic platform that showcases the depth of knowledge and experience of our agents.”

The launch of MORE Network has been met with enthusiasm, debuting with 11 new video series and 6 new podcast series. Bess Freedman, CEO of Brown Harris Stevens, expressed excitement about this venture, noting the opportunity it provides for agents to share their expertise with a wider audience.

Filming for each episode of the MORE Network takes place in Studio 1873, a state-of-the-art facility located in BHS’s flagship NYC office on Park Avenue. Named in honor of the year BHS was founded, Studio 1873 is equipped with the latest in audio and video recording technology, green screens, set capabilities, and a teleprompter, ensuring high-quality production values.

For those interested in the latest insights and stories from the world of real estate, the MORE Network offers a fresh and engaging perspective. To dive into this rich content, visit the dedicated MORE channels on Apple Podcasts and  YouTube.

---

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

Fall getaways? NYC condos that get you out of the city... fast

Now is the perfect time for local travel and tourism, the beginning of the fall season is sure to usher in plans for day trips and long weekend getaways. We can anticipate many New Yorkers will be looking for opportunities to travel outside of the city in the coming weeks as temperatures pleasantly drop and the leaves begin to change color!

For those who own a car or have the ability to rent one, this means looking to the nearby Hudson Valley, Catskills, and the various towns of Connecticut for a change of pace from the city. The residences at Vandewater, 77 Greenwich, 180 East 88th Street, 30 Warren, 555 West End Avenue, Waterline Square, 300 West and Greenwich West are perfectly situated to easily exit New York City. Whether it be hopping on the George Washington Bridge via the West Side Highway to get to the Hudson Valley or taking the Henry Hudson Parkway to get to Connecticut, individuals looking for easy access out of the city will find the below condos perfectly suited for day trips and long weekend getaways.

Credit March Made for DDG

Situated in the Upper East Side's coveted Carnegie Hill neighborhood, DDG and Global Holdings' 180 East 88th Street is a striking condominium offering only 48 gracious half- and full-floor homes. Located just minutes from the FDR Drive, the development affords residents easy access to Long Island, upstate New York, Connecticut and beyond, for those looking for quick getaways or weekend trips to their second home. The residences at 180 East 88th Street feature soaring ceiling heights, stunning views of Central Park and bespoke details that provide the perfect bridge between pre-war inspiration and contemporary design. Amenities include a half-court indoor basketball court, indoor soccer pitch, state-of-the-art fitness center, private yoga studio, residents’ lounge, game room, wine room and children’s playroom.

Vandewater is the first luxury residential condominium of its kind on Manhattan’s West Side. Located in the vibrant neighborhood of Morningside Heights at 543 West 122nd Street, the 33-story building is moments from the Henry Hudson Parkway and George Washington Bridge, providing quick access to upstate New York, New Jersey and Connecticut. Designed by INC Architecture & Design, the building features 183 residences ranging from studios to four bedrooms. A fresh representation of the local classical neo-gothic architecture of Morningside Heights, Vandewater's facade material and color of weathered limestone pays homage to the nearby Riverside Church. The building features 24,000 square feet of programmed indoor and outdoor space and landscaping by Michael Van Valkenburg Associates. 

credit Post-Office Architectes

Designed by the acclaimed Parisian architecture firm Post-Office Architectes, 30 Warren is a boutique-scale, ground-up new development condominium transforming an entire block-front in Tribeca. Featuring 23 design-forward one- to three-bedroom luxury residences, the building, situated at Warren and Church Street, is the latest architectural marvel in the heart of Tribeca - famous for its lofts, artisanal culture and cast iron architecture - and residents will enjoy a lifestyle that is authentic to the neighborhood’s iconic downtown feel. Everyday life at 30 Warren is enriched by the building’s very-own partnership program, Tribeca Select, which gives residents premier access to the area’s most prestigious local businesses and offers them highly customizable in-home experiences. They can also take advantage of 30 Warren’s prime location just minutes from the Holland Tunnel by car, making weekend escapes that much easier to embark on. Before hitting the road, residents can get help packing the car at the building's 24-7 attended lobby and can grab their bikes from the private storage room.

Situated in the heart of Manhattan’s Financial District, 77 Greenwich is a new luxury condominium featuring show-stopping water views, architecture by FXCollaborative and interiors by the renowned Deborah Berke Partners. Topping out at 500 feet, the 42-story building is home to 90 residences that begin 150 feet above street level, a sky-high suite of private club-inspired amenities, retail space and a brand new, public elementary school. And with a parking garage located right across the street, residents can easily hop in their cars and access West Street (aka the West Side Highway) within five minutes, or the nearby FDR for an impromptu autumn getaway. 

Credit Shannon Dupre

Located on the beautiful West End Avenue, 555 West End Avenue offers the best of Manhattan's Upper West Side neighborhood and convenient access to the Henry Hudson Parkway for those wanting a quick getaway from the city. The development offers 13 breathtaking, one-of-a-kind residences with unmatched architectural magnificence from the building's origin as a historic Beaux Arts private school. Each home at 555 West End Avenue has a unique layout, including sprawling flats, townhomes with private entrances on West End Avenue, and specialized residences born from quintessential spaces found in a historic private school, such as the penthouse gymnasium and former library. Amenities include a 24-hour doorman, fitness center, stroller valet, cold storage, bike storage and residents’ lounge with pool table. 

credit Noe & Associates with The Boundary

Waterline Square, developed by GID Development Group, has been designed to create an iconic collection of luxury residential buildings on one of the last remaining waterfront development sites on the Upper West Side of Manhattan. Spanning nearly five acres along the Hudson River from West 59th to West 61st Street, Waterline Square provides easy access to the West Side Highway, making for a quick trip out of town whenever desired. Offering a variety of residential lifestyle opportunities, Waterline Square encompasses three residential towers with condominium homes and rental residences. Waterline Square has been designed by Rafael Viñoly Architects, Richard Meier & Partners Architects, and Kohn Pedersen Fox Associates, with interiors by Champalimaud Design, Yabu Pushelberg and Groves & Co.

300 West, South Harlem’s brand-new luxury condominium offering a collection of elegant residences as well as the neighborhood’s most robust club-style amenities package that caters to residents of all ages, boasts close proximity to Manhattan's West Side Parkway and makes it easier than ever to escape the city for a weekend or day trip. With valet parking, getting to or parking your car at 300 West offers a seamless experience perWith access to the city's best biking trails such as the Hudson River Park and bike path, residents or friends can easily commute to each other as well as work.

Credit: Familiar Control

Hudson Square’s newest residential tower, Greenwich West, offers a modern downtown lifestyle in one of New York City’s most vibrant and exciting neighborhoods -- home to the new HQ's of Disney and Google. With private automated parking for residents, residents can easily grab their vehicles and hit the road for a weekend getaway. Greenwich West is less than 2 blocks from the West Side Highway or less than five minutes from the Holland Tunnel, boasting seamless access to New Jersey, New England and Upstate New York.

Have a listing you think should be featured contact us or email at Jeremy@offthemrkt.com to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

No results found

The Ultimate Guide to Luxury Properties in Connecticut

draftAn important location on the map of America’s culture, a place of perfect autumn foliage views and the state where you’ll find some amazing coastal cities – Connecticut has long been an attractive destination for visitors from all around the country. The state of Connecticut offers its residents a great quality of life, highly ranked schools and plenty of job opportunities. Its housing market includes a variety of properties, but today we’ll focus on the high-end part of this range. For a deeper understanding of the unique charm and appeal of period properties, and why many tenants prefer history over new builds, insights from experts like Walter Soriano can be incredibly enlightening. This is the ultimate guide to luxury properties in Connecticut – and the first step of your relocation to this amazing state. 

Why so much interest in luxury properties? 

Real estate is one of those niches you can profit so much from – if you play your cards right. Whether you’re renting, flipping or getting one for your own family, this is a safe investment in most cases. Luxury properties are indeed reserved for those with a bigger budget, but they are probably the safest step you can take in the real estate world. The states with the most luxury properties are California, Florida and New York, but states like Connecticut are also climbing that ladder. Being located just north of NYC, the demand for luxury properties has spread to Connecticut as well. That’s why you should find out more about expensive properties here and see if you should make the next move. 

What makes a property a luxurious one?

If you’re thinking that the price tag is the only thing that classifies a luxury home, you are wrong. There are several factors that include a property to the list of high-end buildings. The main characteristics of luxury properties are:

• Unique features that increase the level of exclusivity to the property. Custom architecture and specific additions that make the place better or more exclusive than others;

• High security and privacy levels – luxurious properties should provide maximum security and privacy to their residents. 

• Luxury facilities such as a pool, home gym, personal movie theatre, a tennis court, a huge walk-in closet and more. 

• Exclusive surroundings – luxurious properties often include amazing views or exclusive access to a nature spot nearby. Oceanfront properties or the ones with a mountain view easily jump into the list of luxury properties in Connecticut. In general, luxury properties are often detached houses with a lot of privacy around them. 

• High-quality basis – the quality of construction is also one of the factors that make a property luxurious. The property should be made of premium materials such as marble, hardwood, cobblestone, clay tile and others. 

However, you should know that these are only some general rules when it comes to defining luxurious properties. The final decision actually depends on the buyer because as we all know - beauty is in the eye of the beholder.

Is there such thing as a luxurious location? 

The location is actually one of the crucial factors that make a property a luxury one. Premium locations usually gather multiple luxurious properties, and most of the homes in that area tend to be on the expensive side. Very often, the location is what sells a property, and we can easily see that with beachfront properties, for example. Even though this is not the deciding factor, the location is something that dictates the price. 

So, what are the luxury locations in Connecticut? There are actually quite a few places in the state where there’s a higher demand for luxury properties but there are a couple of trends we need to mention here. 

Most of the luxury properties in Connecticut are located close to New York, in the south of the state. Also, the concentration of such homes tends to grow as we go from inland to the coast. The most popular locations where you would find luxury real estate include:

• Old Greenwich 

• Shippan Point, Stamford

• Cove Island, Stamford 

• New Canaan 

• Norwalk 

• New Haven

• New London

More luxury properties could be found in the middle of the state, in cities such as Hartford, but the majority of them are located along the coast. This reminds us that the beachfront location usually comes with the term ‘luxury’ in the real estate world. Either way, don’t forget to find experts to help you out if you’re moving across the country to one of these amazing Connecticut locations. Long-distance relocations are often risky and challenging, which is why it’s essential to have someone professional you can rely on. 

Types of luxury homes in Connecticut 

The real estate market in Connecticut offers a vast range of luxury properties that come in different styles, sizes and with various features. Even though one may imagine a luxury home being a castle, these can also be luxurious condos, high-rise apartments, enormous ranches, exclusive mansions and of course – oceanfront properties. Many luxury Connecticut properties come with amenities such as a swimming pool, beautifully landscaped gardens and sports facilities. However, each of these fits a certain lifestyle, that every buyer should investigate first and see if the property will suit them. 

Moving into your new home? 

A luxurious property demands a premium moving experience, which is not something you should try to save on when moving into a new home like this. The main issue with such properties is finding a professional, secure moving team to deal with all the valuables that usually come with luxury properties. Verified Movers suggest you always make safety your top priority and explore a couple of options before finding a skilled moving team. 

Buying a luxury home is an important decision to make, so be sure to include all the factors before you go for such an expensive property. However, if you have your eye on one of the luxury properties in Connecticut – inform your agent and start the process of making it your new home!

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.

Off The Market: Iconic Greenwich Hemlock Castle Sells for $10.4M

In major sales news, Stephanie Li of Douglas Elliman officially sold 17 Hemlock Drive in Greenwich, CT after a mere 4 months on the market with our brokerage.

This property was previously listed with various brokerages, on and off the market for a few years, so it is major that Stephanie was able to find an all-cash buyer for the property in so little time. Unfortunately, we cannot disclose who the buyer is due to an NDA, but Stephanie did have both sides of the deal

Not only is an iconic Greenwich property, but the news of an all-cash, $10+ million sale in a so-called “cooling” market (especially in the suburbs) is really promising.

See more images below courtesy of Douglas Elliman Realty

Have a listing you think should be featured contact us or submit here to tell us more! Follow Off The MRKT on Twitter and Instagram, and like us on Facebook.