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$2,599,888
7 Beds ⋅ 5 Baths ⋅ 1023664 MLS
Experience pristine living in this exquisite diamond Brookville home, offering unsurpassed value in a highly coveted location. The prestigious approach features a long circular driveway, welcoming you to a serene retreat. The exterior boasts mature specimen plantings and estate fencing encircling a country club style yard with a 20x40 Gunite gas heated pool. The flat 2 acres of entertaining backyard and brick patio, provides ample space to add tennis, pickleball or sport court. This serene oasis is perfect for relaxation and entertainment. Inside the kitchen features hardwood cabinets, complimented by gleaming hardwood flooring throughout the home. 4,717 of finished living space and an additional 1,148 of unfinished basement to create a media room, play room or entertainment cave. The architectural roof adds to the home's timeless elegance. First floor bedroom with en-suite bath and dual walk in closets, and a versatile bedroom/office with a walkout to the fabulous yard. There is so much more to this exceptional property that must be seen to be fully appreciated. Don't miss this rare opportunity to own a true retreat in a serene oasis.

15 Tappentown Lane, Brookville
$5,295,000
6 Beds ⋅ 9 Baths ⋅ 1021182 MLS
Imagine an exclusive lifestyle redefined within a private HOA gated community, where absolute security meets unparalleled luxury on a flat, beautifully landscaped 2.53-acre parcel. This masterfully constructed 7,000-square-foot estate—boasting an impressive six bedrooms and seven bathrooms, each with their own private balcony—is defined by ultra-high-quality finishes throughout, including radiant heated floors, a central vacuum system, and a private elevator servicing all levels. The crown jewel of the residence is a first floor year-round indoor wellness spa complete with a pristine indoor pool, relaxing sauna, and steam room facilities. Designed for flexible multi-generational living, the home features dual (2) primary suites with private balconies and jacuzzi baths, a media room for grand entertainment, a designer eat-in chef’s kitchen anchored by a massive island, and a beautifully finished walk-out lower level. Entertain brilliantly on the expansive rear patio with outdoor kitchen and covered pavilion. Conveniently located just 11 minutes to the Long Island Expressway, this luxury home seamlessly blends elite architecture with a truly exceptional compound experience.

5 Farmwoods Lane, Upper Brookville
$4,249,999
5 Beds ⋅ 6 Baths ⋅ 1022418 MLS
Exceptional brick estate offering 9,023 sq ft of refined living with 6bedrooms and 5.5baths on nearly two private acres in Locust Valley. Built in 2009, the home showcases custom mahogany millwork throughout, a dramatic two-story foyer with a sweeping butterfly staircase, and a great room framed by a soaring wall of arched windows. A first-floor library and dedicated meditation room offer quiet retreats. The chef's kitchen features rich custom cabinetry, coffered ceilings, an oversized center island, and a full suite of Viking appliances including a professional gas range, complemented by a butler's pantry with built-in wine storage and dual Viking wine refrigerators. The grand-scale primary suite is a wing unto itself, with a fireplace, sitting area, boutique-style dressing room, and an oversized spa bath with soaking tub and separate shower. A full-width entertainer's terrace spans the rear of the home, overlooking the manicured grounds. Below, the expansive walk-out garden level opens to the lawn through a graceful arched loggia — ideal for recreation, gym, or guest space. A rare blend of scale, craftsmanship, and privacy moments from Locust Valley village.

250 Oyster Bay Road, Locust Valley
$899,000
4 Beds ⋅ 5 Baths ⋅ 1013410 MLS
Set in the heart of Bayville, 330 Bayville Avenue offers a unique combination of coastal lifestyle, generous living space, and exceptional versatility. With access to a private beach path just moments from the property, morning walks along the shore, summer days by the water, and the relaxed feel of seaside living can become part of everyday life. Offering 4 bedrooms and 5 full bathrooms, the home features a flexible layout that includes a permitted accessory apartment, ideal for extended family, guests, or potential rental income. Two full kitchens provide added functionality and independence between living spaces while allowing the home to adapt easily to a variety of needs. Mother Daughter Opportunity A brand-new roof and gutters were completed in 2026. The home also offers multiple spaces for gathering and entertaining, including an enclosed patio for additional year-round living space. A private driveway provides parking for up to five vehicles. Conveniently located near Bayville’s waterfront, local dining, shops, and amenities, 330 Bayville Avenue presents an opportunity to enjoy space, flexibility, and the coastal lifestyle that makes this community so special.

330 Bayville Avenue, Bayville
$2,895,000
6 Beds ⋅ 5 Baths ⋅ 1019700 MLS
- Low Taxes - $36,000 total - Locust Valley Schools - Village of Muttontown, located on the north side of Northern Boulevard/25A, bordering Upper Brookville -4,850 Sq Ft Colonial - 2 Acres - All Upstairs Bathrooms Fully Renovated with high end finishes - Kitchen features Carrara Marble with new Wolf and Sub-Zero Appliances - Bluestone Patio with fully equipped outdoor kitchen featuring DCS Gas Grill, Lynx Pizza Oven, Lynx Refrigerator, Lynx Ice Maker, Lynx Warming Drawer, Gas Fireplace & Outdoor TV - Heated Saltwater Gunite Pool -Approximately 4.5 miles to LIRR Syosset Set on two beautifully landscaped private acres bordering Upper Brookville, 855 Orchard Lane offers a rare combination of refined interiors, exceptional outdoor living and true move-in-ready luxury. This beautifully renovated five/six-bedroom, four-and-a-half-bath Colonial has been thoughtfully updated for sophisticated everyday living and effortless entertaining. The kitchen pairs Carrara marble with Wolf and Sub-Zero appliances, while gracious living spaces feature custom millwork, rich natural materials and a gas fireplace accented in Imperial Danby marble. The primary suite provides a serene retreat with a spa-inspired Calacatta Gold marble bath and Waterworks fixtures. Each additional bath has been individually renovated with designer stone, fixtures and finishes, creating a consistent level of quality throughout the home. Outside is where 855 Orchard Lane truly distinguishes itself. A sprawling Bluestone terrace extends the living space into a private resort-like setting, with retractable awnings, a fully equipped outdoor kitchen featuring a DCS grill, Lynx pizza oven, refrigerator, ice maker and warming drawer, plus a separate outdoor living area centered around a gas fireplace and television. Beyond the terrace, a heated saltwater Gunite pool with waterfall is surrounded by beautiful lawns and mature landscaping, creating an exceptional backdrop for summer afternoons, intimate dinners and large-scale entertaining. With five/six bedrooms, approximately 4,850 square feet (including finished lower level), two-car attached garage and full-house generator, the property delivers substantial amenities without the scale or maintenance demands of an oversized estate. Located in the Village of Muttontown on the north side of Northern Boulevard/25A and bordering Upper Brookville, 855 Orchard Lane offers privacy, acreage and a beautifully finished North Shore lifestyle—all ready to enjoy.

855 Orchard Lane, Muttontown
$3,195,000
5 Beds ⋅ 5 Baths ⋅ 1020514 MLS
Down a long, private driveway canopied by mature trees, 17 Danton Lane is a modern 5-bedroom, 4.5-bath home that spans approximately 7,000 square feet on over 4 acres, in one of Locust Valley's most coveted beach enclaves, just a stroll from a private beach. A striking 2 story atrium foyer welcomes you in, with glass doors beckoning straight out to the backyard. The kitchen, redesigned in 2019, features large countertops, custom cabinetry, and Viking appliances, while a newly finished basement offers a full bathroom, gym and recreational space. On the main floor, the impressively large great room is designed for entertaining with oversized windows and elegant fireplace. On the other side of the house, the two-story primary suite includes a soaking tub, walk-in closets, and an upstairs office/den. The grounds, designed by Dubner, offer layered points of interest throughout, from a sparkling gunite pool with jacuzzi to a serene koi pond, creating a series of destinations to discover rather than a single view. Clean, contemporary design meets total privacy, lush surroundings, and private beach access on over 4 acres at 17 Danton Lane.

17 Danton Lane N, Locust Valley
$799,000
3 Beds ⋅ 2 Baths ⋅ 1019915 MLS
Welcome to 15 Pershing Avenue, a charming Locust Valley residence where classic character meets modern comfort in one of the North Shore’s most beloved communities. This inviting 3-bedroom, 2-bath home offers a warm and functional layout filled with natural light, timeless appeal, and flexible living space for today’s lifestyle. A thoughtfully designed bonus room provides the perfect option for a home office, guest space, playroom, or creative studio, while the newly finished basement adds valuable additional space ideal for recreation, entertaining, fitness, storage, or extended everyday use. Set on a spacious property with a detached 2-car garage, this home offers room to gather, garden, and entertain. Perfectly located near Locust Valley’s shops, dining, parks, schools, and on Matinecock Border. 15 Pershing Avenue delivers comfort, charm, flexibility, and location in one beautiful package.

15 Pershing Avenue, Locust Valley
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 1019252 MLS
Coastal Living ! Discover the perfect blend of charm, comfort, and modern updates in this beautifully renovated and expanded Cape(primary bedroom and bath on first floor) , ideally situated in a quaint beach community with shopping, dining, and Marina. Thoughtfully redesigned with today's lifestyle in mind, this move-in-ready home offers spacious living areas, stylish finishes, and exceptional indoor-outdoor living. Step outside to your private backyard oasis featuring a built-in vinyl saltwater pool—perfect for relaxing summer days, entertaining or simply enjoying your own resort-style retreat. Just minutes from sandy beaches, a local marina offering boating, kayaking, paddleboarding, fishing, and other water sports, this home is perfectly positioned for those who love an active coastal lifestyle. Conveniently located near shopping, dining, and everyday conveniences, you'll also enjoy easy access to nearby towns and villages filled with boutique shops, restaurants, farmers markets, and seasonal festivals. Whether you're searching for a year-round residence or the perfect weekend getaway, this exceptional Cape offers the ideal combination of coastal charm, modern amenities, and an unbeatable location. Come experience the relaxed beach lifestyle you've been dreaming of!

7 Vine Street, Bayville
$4,998,000
5 Beds ⋅ 7 Baths ⋅ 1018743 MLS
The most discerning will appreciate the unparalleled architectural details and sublime luxury that abounds in this hilltop Classic Contemporary Estate. Renovated top to bottom in 2018 by a professional builder for his personal residence, only the finest European structural and design elements were utilized. "Hilltop" offers a beautiful setting for comfortable living and gracious entertaining. The Open Concept interior floor plan, with floor to ceiling windows and breath-taking sweeping views of the landscape, flows seamlessly to the exterior Ipe deck and patio. Nestled in the Lattingtown Harbor Community, residents enjoy the private beach and clubhouse with mooring rights. All this awaits, a mere 30 Miles from Manhattan and less than 2 miles from downtown Locust Valley with charming shops, fine dining and public transportation. LHPOA Fees approx. $2500/yrly Private Carting., Additional information: Appearance:MINT+++,Interior Features:Marble Bath

8 Frost Creek Drive, Locust Valley
$2,675,000
4 Beds ⋅ 4 Baths ⋅ 1015612 MLS
A rare opportunity to own brand-new direct waterfront construction with private beach access and sweeping views of the Long Island Sound in the heart of Bayville. Perched atop a bluff overlooking the water, this exceptional residence offers the perfect blend of coastal living and modern luxury. Featuring 4 bedrooms and 3.5 bathrooms, the home is thoughtfully designed with an open-concept layout and abundant natural light throughout. The expansive family room is anchored by a gas fireplace and opens through sliding glass doors to the backyard, where breathtaking water views create a stunning backdrop for everyday living and entertaining. The beautifully appointed eat-in kitchen flows seamlessly into the main living spaces, while the private bedroom suites offer their own tranquil retreats. Private balconies off the bedrooms capture panoramic, crystal-clear views of the Long Island Sound, stretching to the Connecticut shoreline and all the way to the New York City skyline. From spectacular sunrises over the water to the twinkling lights of the city in the distance, the views are nothing short of extraordinary. Additional highlights include a 2-car garage, a full basement with high ceilings offering endless possibilities, and direct access to a private beach just steps away. Set within the highly regarded Locust Valley School District, this is a truly unique opportunity to own brand-new waterfront construction and experience coastal living at its finest.

33A Bayville Avenue, Bayville
$2,490,000
4 Beds ⋅ 4 Baths ⋅ 1016868 MLS
Amazingly LOW Taxes & TWO (2) meticulously landscaped acres with salt water POOL, this exceptional Brookville residence showcases refined design, expansive living spaces, and resort-style outdoor amenities. Elegant stone patio with gazebo and outdoor kitchen equipped with a barbecue, refrigerator, and sink. A dramatic entry opens to soaring ceilings with skylights and impressive window walls that flood the home with natural light. The spacious floor plan includes a sprawling living room/dining room, two inviting dens, and a recently renovated eat-in kitchen designed for both daily living and entertaining. Four beautifully updated bedrooms (1 separate bedroom suite with backyard access for second generation) and three-and-a-half baths provide comfortable accommodations throughout. The finished ground level offers versatile additional living space, while the seamless connection between indoor and outdoor areas enhances the home's exceptional functionality and appeal. Move-in ready and thoughtfully updated. Ideally situated near transportation, shopping, dining, parks, universities, golf and tennis facilities, this is a remarkable offering in Brookville.

19 Tappentown Lane, Brookville
$12,250,000
7 Beds ⋅ 10 Baths ⋅ 1017340 MLS
This is an exclusive opportunity to own a turn-key Modern Mansion, perfectly positioned on 5 manicured acres on the Gold Coast of Long Island. Constructed in 2022, this designer residence showcases oversized windows, 12ft ceilings, multiple marble gas fireplaces, pocket doors, glass railings and more. Both captivating and secluded, this residence offers the warmth of a traditional home with a contemporary flair. The first floor has a two story foyer, spacious formal living and dining rooms, an office and a lounge with a built-in bar and billiards area. The state-of-the-art modern kitchen is outfitted with top-of-the-line Viking appliances, Neo Marble countertops, numerous pantries and a sweeping center island with bar seating. Off of the kitchen is a beautiful light-filled eating area, with doors leading out to the backyard, an inviting family room and a bespoke homework area/ work space. The main house boasts 6 vast bedrooms, all with en-suite bathrooms and large closets. The Primary Wing is on the first floor and is outfitted with a private sitting room, 2 patios, a laundry area, 'His and Her' spa-like bathroom with a stand-alone tub and two glass enclosed showers, as well as 2 custom walk-in closets, one totaling over 3,000 Sq.Ft. of storage space. Upstairs also features a playroom with a media center, a crafts room, a matted fitness area and a massive flex room over the 8 car attached garage. Additional interior details include 4 stylish powder rooms, an elevator, 2 full service laundry rooms, a whole-house Smart Camera and Alarm System, a central vacuum system, surround sound speakers and an unfinished basement, with an indoor sports court, spanning the entire length of the home. The exterior is fashioned with a gated entry, a long blue stone and pebble driveway, a solid stucco facade, steel windows and decorative metal gutters. The property is elegantly landscaped and has a 60ft x 25ft Saltwater Heated Pool and Hot Tub, a Cabana with a Kitchenette, a fenced-in Dog Run and a covered patio with an outdoor lounge area, great for entertaining. In proximity to The Village of Locust Valley, the LIRR, charming local beaches and some of Long Island's most prominent Country/Golf Clubs. Zoned for the acclaimed Locust Valley Central School District.

199 Lattingtown Road, Locust Valley
$4,998,000
6 Beds ⋅ 7 Baths ⋅ 1010689 MLS
A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a two-story entryway, a luxurious primary suite on the main level, a free-form inground heated gunite pool with a waterfall, a covered outdoor kitchen, and a 3-car garage. Luxurious living with hidden privacy and easy access.

7 Fairway Court, Upper Brookville
$1,550,000
5 Beds ⋅ 4 Baths ⋅ 1012983 MLS
Drive down a beautiful, tree-lined street and arrive at your private 2-acre sanctuary. Situated on a sweeping circular driveway, this expansive ranch offers incredible versatility and endless possibilities to suit your lifestyle. Grand Open-Concept Living Room features dramatic cathedral ceilings and a versatile layout. It easily accommodates a formal living setup while seamlessly incorporating a cozy, firelit sitting area. The oversized formal dining room sits privately adjacent to the living room and kitchen, offering serene views of the wooded acreage. This flexible space can easily transform into a grand family room, where the warmth of the fireplace creates an inviting winter retreat. The Chef’s Kitchen was redesigned to include premium amenities, featuring granite countertops, a large cooktop, stainless steel appliances, and direct access to the expansive rear yard. It is complete with a breakfast bar and dining area. A Primary Suite serves as a peaceful retreat complete with generous closet space and a private en-suite bath. A Spa-Like Main Bath which has been beautifully updated to serve as your personal oasis, featuring a double vanity, a whirlpool tub, and a separate shower. This home features a total of 5 bedrooms, including 2 tucked privately on the second floor. A convenient powder room is also located just off the entrance foyer for guests. The full Basement spans the entire footprint of the house. This massive, unfinished lower level is a blank canvas ready to be customized into a home theater, gym, or recreation room. Step outside into the rear yard and experience pure paradise. Peace, tranquility, and breathtaking natural beauty await your finishing touches.

3 Fox Lane, Locust Valley
$1,329,000
4 Beds ⋅ 3 Baths ⋅ 1011626 MLS
Experience coastal luxury in this fully renovated 4 bedroom, 3 bath waterfront Contemporary Colonial in Bayville. Designed to maximize breathtaking water views, this exceptional home features an open-concept floor plan with walls of glass that fill the interior with natural light and showcase this stunning shoreline. Great room has new sliders overlooking water and a striking stone fireplace serves as the focal point of the main living space creating the perfect setting for entertaining or relaxing year round. The gourmet kitchen is beautifully appointed with center island, quartz countertops, custom shaker cabinetry and a full suite of high-end appliances. First floor also includes lovely French doors seamlessly flowing into the spacious living and dining areas and a half bath. Second level has 4 large bedrooms, 2 full baths and laundry area. Retreat to the spectacular primary suite featuring vaulted ceilings, a dramatic wall of windows overlooking the waterfront, and direct access to a private waterfront deck - your own personal sanctuary to enjoy morning coffee or evening sunsets. Primary bath features vaulted ceilings, huge separate shower, soaking tub, double sinks, space age toilet and recessed lighting. Additional features include high-tech ceiling fans and radiant heat in several rooms. Outdoor living is unparalleled with new stone front, all new siding, a new roof, circular driveway and expansive new Trex decking on both the first and second levels, offering multiple spaces to take in the panoramic water views. Launch your kayak right from your backyard and embrace the waterfront lifestyle. As an added bonus, enjoy access to a private beach on the Long Island Sound side, where picturesque sunsets paint the sky each evening. This rare Bayville waterfront gem combines modern luxury, thoughtful design, and an unbeatable location delivering the ultimate year round vacation lifestyle. A truly extraordinary opportunity not to be missed.

35 Adams Avenue, Bayville
$1,075,000
4 Beds ⋅ 3 Baths ⋅ 978767 MLS
Welcome to 12 Deans Lane, Bayville, a fully renovated 4-bedroom, 3-bath residence offering beautiful water views of Mill Neck Creek and a sought-after coastal lifestyle near the beaches of Bayville and Oyster Bay. Thoughtfully updated throughout, this home features a bright, open layout filled with natural light and a seamless flow designed for both comfortable everyday living and easy entertaining. The main living area is centered around a fireplace, creating a warm and inviting gathering space. The renovated kitchen combines style and function with quartz countertops, modern cabinetry, and energy-efficient appliances, while the adjoining dining area opens directly to the deck and patio for effortless indoor-outdoor living. The home offers well-proportioned and versatile bedrooms, along with three beautifully renovated bathrooms finished with contemporary fixtures and tasteful design. Hardwood flooring enhances the upper level, while the finished lower level features tile flooring and crown molding, adding both character and flexibility to the living space. Additional conveniences include a washer/dryer hookup and an attached 2-car garage with added storage. Recent exterior updates, including a new roof, vinyl siding, and updated windows, contribute to the home’s curb appeal, efficiency, and low-maintenance appeal. Ideally located near Bayville and Oyster Bay beaches, waterfront recreation, parks, restaurants, shops, and everyday conveniences, this property offers a wonderful opportunity to enjoy renovated living with scenic water views and the best of North Shore coastal charm.

12 Deans Lane, Bayville
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 1003640 MLS
Well maintained waterfront home directly on Long Island Sound. Private maintained beach with views to Connecticut. Home features 3 or 4 large bedrooms with 3 full baths upstairs with separate laundry room. Oversized Master with private deck, walk-in closet, and marble master bath. Kitchen & dining on first floor with sunken living room & gas fireplace, all with water views. Oversized Brazilian Hardwood deck & paver patio with steps to beach. Roll-up awning & Anderson patio doors for entertaining. Home features include 3 zones of both heat & A/C, on demand tankless hot water heater. Full home 22K Generac generator, Central Vac, Custom closets. Beautiful outdoor space with paver walkways & tranquil pond. Quiet dead-end block with only 17 homes. Association dues $700 annually maintains private road & beach.

19 Oak Shore Drive, Bayville
$8,975,000
6 Beds ⋅ 9 Baths ⋅ 1011822 MLS
A Legacy Estate of Uncommon Distinction — Buttonball Hill Conceived in 1929 for Vanderbilt heir Aldred Coster Schermerhorn, Buttonball Hill is a masterwork of Georgian architecture set amid sweeping manicured grounds. The classic red brick and clapboard exterior — crowned by a slate roof and crisp black shutters — announces itself with quiet authority. Inside, a double-height foyer with hand-carved moldings and a gracefully curved staircase sets the tone. Soaring ceilings and a natural flow make the principal rooms equally suited to intimate daily living and grand entertaining. The formal living room opens through French doors into a sun-filled solarium; the chestnut-paneled library and cozy den each offer their own fireplace and garden access. The chef’s kitchen is a true centerpiece — expansive and impeccably appointed, with top-of-the-line appliances, custom cabinetry, and generous counter space designed for serious cooking and effortless hosting. Multiple seating areas make it the natural heart of the home: a sun-drenched breakfast nook overlooking the gardens, a sprawling island ideal for casual dining, and a comfortable sitting area perfect for gathering with family and guests. The primary suite is a sanctuary: sitting room, two ensuite baths, fireplace, and a private balcony with sweeping estate views. Outside, a heated pool, Har-Tru tennis court, and beautifully landscaped gardens round out the resort-caliber grounds. A superbly maintained estate where historic soul meets modern ease — minutes from top schools, village amenities, and convenient rail access to the city.

52 Piping Rock Road, Locust Valley
$1,149,000
4 Beds ⋅ 3 Baths ⋅ 1010411 MLS
Welcome to 6 Cedar Ave, nestled in the tranquil and private locale of Locust Valley, NY, is a delightful 4-bedroom, 3-bathroom center hall colonial home. Constructed in 1988, this residence spans a generous 2,538 square feet and is situated on approximately 7000 square foot lot. The home exudes a blend of classic colonial style with modern upgrades, featuring a cozy fireplace and a combination of tile, carpet, and hardwood flooring. Recent updates include a charming deck and pergola, which provide a perfect setting for outdoor gatherings while overlooking the yard. The property also offers ample space to accommodate an inground pool, enhancing the outdoor living experience. Inside, the home is warmed by baseboard heating with oil and cooled by new 2024 Central Air Conditioning. Additional conveniences include an attached garage for parking and essential appliances like a dishwasher, dryer, freezer, microwave, range/oven, refrigerator, and washer, making it an ideal family retreat with both comfort and privacy. First Floor Windows approx. 12 Years, Most of the 2nd floor windows were replaced 2026, New Oven, Dishwasher, Refrigerator 3 years old, CAC 3 Years. New Front railing is being installed. New estate fencing in the yard.

6 Cedar Avenue, Locust Valley
$5,888,000
6 Beds ⋅ 6 Baths ⋅ 1001932 MLS
Discover unparalleled luxury in the heart of Muttontown at 2 Chelmsford Drive, a striking post-modern custom-designed new construction set on a breathtaking 2-acre country club setting. Surrounded by specimen plantings and professionally curated landscaping, this extraordinary estate offers exceptional craftsmanship, sophisticated design, and resort-style amenities throughout. A dramatic custom pivot front door opens to a grand paneled foyer with soaring ceilings ranging from 14 to 20 feet, creating an impressive first impression. Wide-plank white oak floors and custom Pella windows enhance the home's warm, contemporary elegance. The state-of-the-art chef’s kitchen is a true showpiece, featuring rich walnut cabinetry, stunning black quartzite countertops, and a full suite of premium Wolf appliances, including double ovens, a six-burner cook top with griddle, microwave, built-in coffee system, separate ice maker, beverage refrigerator drawers and subzero refrigerator. The formal dining room offers soaring ceilings and walls of glass that open to an outdoor entertaining terrace complete with a full kitchen, pizza oven, and fireplace. The spectacular living room features a double-sided gas fireplace and a custom plaster ceiling. The luxurious primary suite boasts a dramatic 20-foot ceiling, built-in designer headboard feature wall, private deck overlooking the expansive grounds, two custom walk-in closets, and a designer spa bath. Three additional bedrooms are conveniently located on the main level. A stunning illuminated floating staircase leads to the lower level, where you will find additional guest bedrooms, a private gym with adjoining sauna and bath, a large movie theater, and an oversized recreation room with wet bar and glass doors opening directly to the backyard oasis. Designed for ultimate outdoor enjoyment, the country club-inspired grounds feature an oversized heated saltwater Gunite pool with spa, an elegant cabana with outdoor kitchen, and a separate pool house for storage. Automobile enthusiasts will appreciate the extraordinary garage capacity for up to 10 vehicles, including two car lifts, along with a circular paved driveway that completes this one-of-a-kind estate. 2 Chelmsford Drive is a masterfully designed residence that seamlessly blends architectural excellence, luxury amenities, and unparalleled lifestyle living.

2 Chelmsford Drive, Muttontown
$4,500,000
6 Beds ⋅ 5 Baths ⋅ 1003784 MLS
MAJOR PRICE ADJUSTMENT: Enter the wrought iron gates, crowned with classic gas lanterns that cast a warm, welcoming glow and along a private drive, Rolling Meadows reveals itself with the quiet authority of architecture built without haste -a classic brick Georgian residence with stately columns and a slate roof, set amid nine-plus acres of gracious formal gardens and mature specimen trees. Inside, wide plank oak floors create genuine character. A sweeping staircase rises from the entry foyer; the living room and imported Filipino mahogany-paneled library each offer wood-burning marble fireplaces; the formal dining room features a distinct china showcase; and the chef’s kitchen — with its substantial center island and adjoining breakfast room — is designed for both daily living and entertaining. The principal suite is positioned on the main floor, offering exceptional privacy, generous dressing, and a unique ensuite bath. A first-floor guest suite, three additional second floor bedrooms, a substantial bonus room and a three-car attached garage complete the residence. The grounds are as fully realized as the interiors. An Innocenti and Webel pool and dedicated pool house provide an effortless setting for outdoor entertaining. The equestrian facility comprises a seven-stall barn, multiple paddocks and on-site staff quarters. The serious equestrian infrastructure is complemented by a three-car attached garage. There are two additional outdoor garages on the estate. Rolling Meadows is that increasingly rare proposition: a fully equipped country estate where architectural pedigree, equestrian infrastructure, and the warmth of a well-appointed home meet without compromise. A property of this character is best understood in person.

550 Chicken Valley Road, Locust Valley
$25,000,000
13 Beds ⋅ 17 Baths ⋅ 1001064 MLS
Experience Applewood Estate — a generational North Shore compound where timeless architecture, historic provenance, and resort-caliber living unfold across more than 35 secluded acres in the esteemed Village of Upper Brookville. Once an operating apple orchard in the early 1900s and later owned by renowned American artist Montague Flagg, this extraordinary estate carries a legacy as rich as the land itself. Hidden behind a gated, tree-lined approach, the property reveals a breathtaking landscape of rolling lawns, mature specimen trees, formal gardens, peaceful water features, and open meadows designed to evoke the grandeur of Long Island’s historic Gold Coast estates. Inspired by Tudor Cotswold architecture, the compound is a masterclass in cohesive design, blending old-world craftsmanship with modern luxury across multiple residences and lifestyle amenities. The centerpiece is a magnificent custom-built Manor residence encompassing approximately 13,000 square feet of refined living space. Constructed in 2005 with slate, brick, and stone, the home showcases extraordinary craftsmanship through onyx marble accents, oversized parquet flooring, handcrafted iron fireplaces, detailed millwork, and dramatic entertaining spaces throughout. A grand foyer anchored by a sweeping staircase introduces interiors defined by warmth and scale, including a soaring ballroom with 23-foot coffered ceilings, an elegant library loft, meditation room, billiards lounge with wet bar, and a sun-filled eat-in kitchen with breakfast room overlooking the estate grounds. Designed as a true multi-structure compound, Applewood Estate includes several additional residences and guest accommodations, including a beautifully renovated barn residence with attached two-bedroom cottage, an additional two-bedroom cottage, a two-bedroom pool house, a one-bedroom studio, and a meticulously reconstructed circa-1914 stone barn now transformed into a luxurious retreat. Outdoor living is equally exceptional. The estate features a heated swimming pool and spa pavilion, built-in outdoor kitchen, resurfaced tennis court, separate sports court, expansive paddocks, and formal equestrian facilities complete with horse stables and a training ring. Additional highlights include a six-car detached garage, maintenance barn, commercial-grade 150kW generator, and secure gated entry, all thoughtfully integrated into the estate’s serene natural surroundings. Rarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shore’s most coveted enclaves. Applewood Estate is not simply a home — it is a private world crafted for legacy living, grand entertaining, and timeless retreat.

1 Applewood Estate, Upper Brookville
$924,000
4 Beds ⋅ 2 Baths ⋅ 1001116 MLS
Welcome to 28 Satinwood Road, a spacious and thoughtfully updated four-bedroom, two-bath home in the beautiful village of Bayville, offering more than 2,200 square feet of flexible living space in an established non-flood zone neighborhood that offers access to private village beaches, docks, pickleball, tennis courts and mooring rights. Locust Valley School District. Plenty of restaurants, activities with close proximity to shopping-everything that makes Bayville village living special. Move-in ready and filled with natural light, this home combines a thoughtfully updated interior with the space, storage and practical features that are hard to find—including a two-car garage, flexible lower-level living space, a generator with automatic transfer switch and a double gate at the side yard offers dedicated space for additional cars, a boat, trailer or RV. For added convenience, washer and gas dryer hookups are located on both levels, eliminating the need to carry laundry between floors and adding even greater flexibility to the home’s two- level layout. The main level welcomes you with freshly painted walls, gleaming hardwood floors and large windows with plenty of natural light. The completely remodeled kitchen features high ceilings, solid-surface countertops, a deep stainless-steel farmhouse sink, newer appliances, soft-close cabinetry, abundant storage and gas cooking. Sliding glass doors open directly to the large deck, creating an easy flow for outdoor dining and entertaining. The adjoining living and dining rooms feature hardwood floors, crown molding and oversized windows, providing a bright, comfortable gathering space. Throughout the home, thoughtful upgrades include wood-paneled doors, custom blinds, updated lighting and Elfa closet systems. Just down the gallery style hall you’ll find three of the four bedrooms. The spacious primary bedroom with deep double-door closets and windows on multiple walls for wonderful natural light. Two additional bedrooms comfortably accommodate queen-size beds and include custom closet systems. The main-level full bath offers a large vanity with storage, tub/shower combination and ceramic tile flooring. The lower level adds exceptional flexibility for today’s lifestyles. A fourth bedroom with a custom closet system sits alongside a beautifully remodeled bath that feels like a spa retreat with stone pebble floor shower and custom tilework. Combined with a spacious den/flex area, separate laundry and sliding doors leading to a large sunny backyard, this level is ideal for multigenerational living, extended-stay guests, a home office, fitness area or additional Rec space. The two-car garage provides additional storage and workshop space. The attic, accessed by newer pull-down stairs, provides even more storage. Major improvements add comfort and peace of mind, including newer central air, updated electrical, newer hot water heater and a generator with automatic transfer switch. Move in, unpack and start enjoying life in Bayville.

28 Satinwood Road, Bayville
$3,700,000
4 Beds ⋅ 4 Baths ⋅ 955669 MLS
Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Beautifully appointed with crisp white cabinetry, honed Absolute Black granite countertops, top-of-the-line appliances, and radiant heated floors, the kitchen flows effortlessly into the informal dining area and family room, complete with a raised-hearth stone fireplace. Additional highlights include pristine condition throughout, Newly painted and redone guest quarters, separate living and dining rooms, and a separate hot water heater., New generator, new gas line (2025), House newly painted and redecorated and grounds re landscaped. The Property in Spring is filled with an abundance of color with the Hellebores, Azaleas, Rhododendron. It is private and magical.

343 Chicken Valley Road, Upper Brookville
$3,600,000
7 Beds ⋅ 6 Baths ⋅ 995929 MLS
Rosegate is an enchanting mini estate that harkens back to golden age of the North Shore of Long Island. This architectural gem has been thoughtfully expanded over the years into a stately 7-bedroom Colonial, set on 2.85 acres of lush, storybook grounds. Every inch of Rosegate exudes character and charm from its Ludowici style roof to its diamond trellis ivy covered walls. Step through the front entrance, and you’re greeted by exquisite hand-painted murals that set the tone for the artistry and elegance within. The sun-drenched living room and formal dining room, with their graceful proportions and classic design, provide an exceptional setting for entertaining, while timeless details like wood-pegged and parquet floors along with elegant archways elevate every space. For those seeking quiet retreat, the library leads to a cozy bedroom (or office) with a beamed ceiling and French doors that open to the serene pool area. A touch of convenience and sophistication, the home also features an elevator for easy access to the second-floor primary suite. A separate guest wing with three bedrooms and a full bath offers privacy and comfort for visitors. The outdoors are a masterpiece in their own right. The gated front garden with whitewashed brick sitting walls and specimen plantings is highlighted by a charming center fountain. The rear garden, with its sweeping lawn, showcases a sparkling Gunite pool surrounded by a bluestone patio—perfect for summer gatherings. A charming greenhouse by the 3 car garage completes this idyllic retreat. Steeped in history yet updated with modern comforts, Rosegate is more than a home—it’s a timeless escape that captures the heart and imagination.

285 Piping Rock Road, Locust Valley
$5,250,000
6 Beds ⋅ 8 Baths ⋅ 985121 MLS
An exceptional private brick estate compound set on approximately 7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property views, 6 spacious bedrooms with en-suite baths, 7.5 baths, large eat-in kitchen with generous counter space and storage, and full finished basement. Designed for both daily living and elevated entertaining, every space offers comfort, presence, and functionality. The meticulously designed grounds create a resort style setting with a custom 22,000 gallon koi pond, custom lighting, newly resurfaced Har-Tru tennis court, heated gunite pool, 8-person hot tub, pool house with kitchenette, full bath and changing room, custom outdoor kitchen, and premium speaker system inside and out. Complete with space for 10-cars, car lifts, and carport, this rare Upper Brookville estate delivers privacy, scale, luxury, and an unmatched indoor and outdoor lifestyle. A rare opportunity to own a private Upper Brookville estate with exceptional amenities and beautifully maintained grounds.

45 Wolver Hollow Road, Upper Brookville
$799,000
4 Beds ⋅ 2 Baths ⋅ 991119 MLS
Bayville living at its finest - just moments from charming village amenities and the pristine beaches of the Long Island Sound. Tucked away in one of the North Shore’s best-kept secrets, this beautifully renovated residence seamlessly blends timeless character with modern comfort. Experience the ease of a close-knit beach community (proximity to parks, bridge and marina) while remaining conveniently connected to the LIRR and major roadways. This thoughtfully updated 1930s Cape Cod offers 4 bedrooms, including one on the first floor, and 2 revamped full bathrooms. While enhanced with contemporary finishes, the home retains its original warmth and charm including the exquisite, intricate stair banister. Gleaming hardwood floors, an open-concept layout, and abundant natural light create a bright, inviting coastal atmosphere throughout. The main level features a welcoming foyer with a cozy sitting alcove, a formal living room, a formal dining room, and an eat-in kitchen complete with beautifully painted cabinetry, quartz countertops, and a stylish stone backsplash. There is a large, unfinished basement with a laundry area, utilities and ample storage. Outside, a sizable brick and cement patio, flat lawn space and a storage shed provide both functionality and convenience. Located within the highly regarded Locust Valley School District, this home effortlessly combines beachside ease, enduring character, and modern-day upgrades.

17 June Avenue, Bayville
$7,200,000
6 Beds ⋅ 9 Baths ⋅ 987913 MLS
Dam House is a magnificent 8.66-acre waterfront estate presiding over brilliant sunsets and water views of Beaver Lake. Completed in 1926, the masterfully designed six - bedroom Colonial residence has a refined elegance and timeless charm. It is complemented by expansive bluestone and red-brick patios, a four-bedroom cottage, a one-bedroom pool house, a sparkling swimming pool and a hard surface tennis court. Shade, specimen and flowering trees proliferate the captivating gardens. Manicured shrubs and flowering perennials add to the landscaped beauty. Additional amenities include an irrigation system, an outdoor fireplace, a vegetable garden, a root cellar and two enclosed dog runs with shelter. Full house generator for the main residence and a separate generator services the cottage. Attached two-bay garage and detached four-car garage. This property offers a luxurious lifestyle, in an idyllic waterfront setting.

200 Cleft Road, Mill Neck
$1,199,999
3 Beds ⋅ 3 Baths ⋅ 986971 MLS
Exceptional Colonial in the Heart of Bayville~ Welcome to this stunning 3-bedroom, 3-bathroom colonial nestled in one of Long Island's most sought-after beach communities. Offering 2,716 square feet of thoughtfully designed living space, this home seamlessly blends timeless colonial charm with modern, contemporary finishes. The main level impresses with an open floor plan, gleaming radiant heat hardwood floors, and a warm, inviting fireplace — perfect for both entertaining and everyday living. The eat-in kitchen flows effortlessly into the main living areas, creating the connected, airy feel today's buyers love. A convenient half bath completes the first floor. Upstairs, the spacious primary suite serves as a true retreat, while two additional bedrooms and two full baths offer comfort and flexibility for guests alike. Central air conditioning keeps the home cool and comfortable year-round. And take in breathtaking views of the iconic Bayville Bridge The finished basement provides valuable bonus space ideal for a home office, playroom, or media room. Step outside to a large patio overlooking a tranquil goldfish pond , Set on a generous half-acre lot, this private backyard oasis is the perfect setting for morning coffee, sunset gatherings, and everything in between. Located within the highly acclaimed Locust Valley School District and moments from the beach, this home offers the ideal combination of community, convenience, and coastal lifestyle. This is Long Island living at its finest.

16 E Slope Road, Bayville
$765,000
3 Beds ⋅ 2 Baths ⋅ 957217 MLS
Move in ready sunny 3 bedroom , 2 full bath home in the heart of Bayville. The Living room and Dining room are spacious with beautiful hardwood floors and an enclosed porch makes a terrific playroom/office. The kitchen with Kenmore appliances, microwave and gas stove all overlooking the backyard makes a great enjoyable space to work in. Many updates including windows, new roof with new leaders and gutters, (2023), new cesspool (2021), kitchen updated in (2014) and has electric heated tile floors. Freshly painted in (2024), New 200 amp electrical service installed (from the pole) in 2024. All bedrooms are on the second floor and have hardwood floors and 2 windows making each room cheery and bright. There is one full bath on the second floor and one full bath on the main. A side door off the kitchen provides easy access to parking. Convenient to shops, dining, and the LIRR. The backyard is private, and fenced with a large paved patio making this a perfect entertaining space. Not in the Flood Zone. Beach and mooring rights available.

22 Perry Avenue, Bayville

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