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$697,900
2 Beds ⋅ 2 Baths ⋅ MDQA2017900 MLS
Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

121 Merlin Dr, Chester
$545,000
3 Beds ⋅ 3 Baths ⋅ 1018371 MLS
This Chester raised ranch checks every box: bright, spacious living areas, a stainless steel kitchen, and a finished basement ready for a home office, gym, or guest space. Smart-home upgrades — Nest thermostat, Ring security with window sensors, reverse osmosis filtration — add everyday ease, while the primary boiler plus central HVAC keeps you comfortable in every season. Out back: a deck, above-ground pool, and new white vinyl privacy fence for total backyard privacy. Just 12 minutes to Woodbury Common Outlets with easy highway access. This home offers the perfect blend of peaceful suburban living and everyday convenience. Don't miss the opportunity to make it yours!

11 Chandler Drive, Chester
$515,000
5 Beds ⋅ 3 Baths ⋅ MDQA2017856 MLS
SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the potential to create a private in-law suite. The main level features easy-care LVP flooring, while the lower level has been refreshed with brand-new carpet, giving the home a fresh, move-in-ready feel. Multiple living and gathering spaces mean there is room to spread out without sacrificing connection. Outside, the possibilities continue! Enjoy morning coffee on the screened porch, entertain on the spacious deck, or take advantage of the large backyard for play, pets, gardening and gatherings. Car enthusiasts, hobbyists and anyone needing serious storage will LOVE the impressive detached 4-car garage—an increasingly hard-to-find feature on Kent Island. And the best part? NO HOA! Enjoy the freedom to make the property your own without the added monthly community expense. With 5 bedrooms, two levels of flexible living space, updated baths, multiple outdoor living areas, a huge backyard and an exceptional 4-car detached garage, 205 Anchor Lane delivers an incredible amount of home and versatility for the money. If you've been searching for true VALUE on Kent Island, this one deserves a look! With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester
$599,900
3 Beds ⋅ 2 Baths ⋅ MDQA2017854 MLS
REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester
$850,000
5 Beds ⋅ 3 Baths ⋅ 1020076 MLS
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

5 Hilltop Lane, Chester
$724,999
4 Beds ⋅ 3 Baths ⋅ MDQA2017836 MLS
Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel appliances, a large center island, and plenty of space to gather with family and friends. The cozy gas fireplace adds warmth and charm to the main living area, while the screened patio is the perfect spot to relax with your morning coffee or unwind at the end of the day.The large primary suite offers a peaceful retreat with a spacious walk-in closet, double vanities, and a walk-in shower. Additional bedrooms AND an office provide plenty of room for guests, hobbies, or just about anything you can think of and the convenient mud room adds extra functionality.Living in Four Seasons at Kent Island means enjoying an incredible lifestyle. Residents have access to a stunning 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and a full-time lifestyle director who keeps the social calendar full of activities including walking clubs, yoga, mahjong, kayaking, pickleball, and more.Kent Island living is all about making new friends, staying active, and enjoying the lifestyle you've worked hard to achieve. Come see why so many people are proud to call Four Seasons home.

233 Peregrine Dr, Chester
$2,840,000
5 Beds ⋅ 4 Baths ⋅ MDQA2017820 MLS
Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms) recently updated in spring 2026. The former detached garage converted into the guest cottage (2BR, 1.5 BA) has a fabulous screened porch you'll spend endless hours on. A separate building provides versatile storage for equipment or hobbies. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors in most rooms. Upgraded countertops and new appliances elevate the kitchen, convenient to the screened porch perfect for gatherings. The living room, complete with a brick fireplace, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom, or home office, in this traditional floor plan that flows seamlessly throughout. The exterior amenities are equally impressive, featuring a private shoreline and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. . The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or gardens.. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester
$750,000
4 Beds ⋅ 4 Baths ⋅ 1020165 MLS
Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home. Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday living and entertaining. Sunlight pours into the beautiful sunroom, offering the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the tranquil views of the property throughout every season. Step outside and discover the true highlight of this remarkable property. Designed with entertaining in mind, the backyard is a private oasis featuring a sparkling inground pool, beautifully integrated outdoor living spaces, a custom built fire pit, and built in seating that invites family and friends to gather long after the sun goes down. Whether you're hosting summer pool parties, enjoying crisp fall evenings by the fire, or simply relaxing in your own backyard retreat, this outdoor space delivers an exceptional lifestyle year round. Set on over three private acres, the property offers the perfect balance of open space and privacy. There is plenty of room to explore, play, garden, or simply enjoy the serenity of nature, all while being just minutes from the conveniences of the Hudson Valley. Offering 4 bedrooms, inviting living spaces, and an outdoor setting that feels like your own private resort, this is more than just a home. It is a place where memories are made, weekends are enjoyed, and every season brings something special.

985 Craigville Road, Chester
$634,999
4 Beds ⋅ 3 Baths ⋅ 1013375 MLS
Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment. Inside, the home offers 2,316 sq ft of comfortable living space with a practical raised-ranch layout, full basement, and room to expand or personalize. The private 2.5-acre setting provides privacy, outdoor space, and room to enjoy the Hudson Valley lifestyle while remaining convenient to major routes and amenities. Whether you’re looking for extra vehicle capacity, a home-based business space, or simply room to breathe, the 6-car garage combined with the acreage makes this a standout property in the area. Monroe-Woodbury schools. Schedule your showing today. Located in Orange County with easy access to major routes, this property delivers the space and privacy so many buyers are searching for — without sacrificing convenience. Whether you’re looking for a primary residence with room to grow or a peaceful retreat, 424 Laroe Road offers a strong foundation and exceptional land value. Key Features: 4 bedrooms | 3 bathrooms 2,316 sq ft 2.5 private acres Expansive deck for outdoor living Built 1974 – solid bones with modern potential Convenient Chester location Schedule your private showing today and experience the space, privacy, and potential for yourself.

424 Laroe Road, Chester
$699,000
3 Beds ⋅ 2 Baths ⋅ MDQA2017690 MLS
Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

205 Riverside Dr, Chester
$789,900
5 Beds ⋅ 4 Baths ⋅ 1012919 MLS
Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living areas, well-proportioned bedrooms, central air conditioning, and a versatile floor plan designed to accommodate a variety of lifestyle needs. At the heart of the home is a chef’s kitchen equipped with professional-grade appliances, offering an exceptional setting for preparing meals, entertaining guests, and gathering with family and friends. The finished lower level provides additional flexible space for a recreation room, media area, home gym, private office, or guest accommodations. An attached garage adds convenient parking and storage. Step outside and enjoy an inviting outdoor setting highlighted by an outdoor fireplace, creating the perfect atmosphere for relaxing evenings, seasonal gatherings, and memorable moments under the Hudson Valley sky. Located within the Chester School District, the property offers convenient access to local shopping, dining, recreation, commuter routes, and the many attractions of Orange County and the Hudson Valley. Buyers searching for a spacious five-bedroom home in Chester, NY, with a chef’s kitchen, professional-grade appliances, flexible living space, a finished lower level, and exceptional indoor-outdoor entertaining features will appreciate everything this property has to offer. 19 Grand View Terrace combines generous living space, elevated amenities, and a desirable Chester location—an exceptional opportunity to create the home and lifestyle you have been searching for.

19 Grand View Terrace, Chester
$1,195,000
4 Beds ⋅ 4 Baths ⋅ 1010585 MLS
Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

22 Goshen Road, Chester
$875,000
4 Beds ⋅ 3 Baths ⋅ 1011165 MLS
Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by nature. The soaring great room creates a dramatic first impression, while the beautifully updated kitchen serves as the heart of the home with its oversized island and bright, modern finishes. Outside, the expansive grounds provide endless possibilities—from entertaining and recreation to simply enjoying the peaceful surroundings. With 4 bedrooms, 2.5 baths, and over 3,600 square feet of living space, this property offers room to spread out while enjoying the privacy and beauty of its remarkable setting.

49 Stone Mountain Trail, Chester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 1010784 MLS
This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

63 Whitetail Run, Chester
$990,000
4 Beds ⋅ 3 Baths ⋅ 1006113 MLS
Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of something that has absolutely nothing to prove. Brook Farm has been here since 1851. It will be here long after you. This is the kind of home that changes the way you think about time. Originally the crown jewel of financier Richard Delafield's 128-acre Brook Farm estate — named after his Tuxedo Park retreat — the manor was designed from the very beginning for a life lived generously. For gathering people. For long dinners that drift into evening. For the kind of entertaining that doesn't need a theme, because the house is the occasion. Step through the front door and the ceilings rise to greet you — twelve feet of plaster and molding, the proportions of a home that was never meant to feel small. The formal rooms flow one into the next: parlor, drawing room, dining room, each anchored by original fireplaces, each telling you without a word that whoever built this place understood how a house should feel. The hardwood oak floors, the walnut trim, the two grand staircases with their original woodwork — these aren't period details. They're the bones of the place, still standing, still beautiful, still doing exactly what they were put here to do. Upstairs, four bedrooms carry the same unhurried character — rooms with depth and soul, served by two full baths and a dressing room. A walk-up third floor adds two finished bonus rooms: a studio, a library, a playroom, a quiet office above the treetops. The house keeps offering more. And then there's the basement. Name it what you want — a tavern, a speakeasy, a rumpus room — but nothing quite prepares you for it. A massive brick fireplace. A built-in bar. Full-size windows flooding the space with light. And a door that opens directly onto a sunken pebbled courtyard, walled and private, where summer evenings could easily become a habit. Beyond the main house, the estate unfolds across 6.8 acres of lawn, mature trees, and open land. A charming 882-square-foot guest cottage — two bedrooms, one bath, fully independent utilities — sits privately apart from the manor. It's the kind of setup that solves problems you haven't had to solve yet: visiting loved ones, aging parents, a long-term guest, a rental income stream, a caretaker's quarters. The dairy barn and outbuildings hint at the property's agricultural past and offer a footprint ready for whatever comes next — a workshop, a studio, a small farm, a vision that hasn't quite taken shape yet but will the moment you walk the land. There's even a tennis court. Fifty-five minutes from Midtown Manhattan, charming village setting, close to the Rail Trail, highways, the Goshen Historic Track, Legoland, the Shawangunk Wine Trail, and some of the best farm-to-table dining in the Hudson Valley — Brook Farm is private without being remote, historic without being frozen in time. Properties like this — with this much land, this much character, this much history — don't come back on the market. This one hasn't been available in over seventy years. The people who have lived here understood what they had. Now it's your turn. A special property steeped in character, with a story already written… and a bold new one waiting to begin. Full of soul and raw possibility, it’s ready for reinvention, for reimagination, for a whole new energy. Awaken its potential, elevate its spirit, and make it entirely your own. The next chapter is yours to craft. Your vision. Your legacy. Schedule your private showing today.

1 Oakland Avenue, Chester
$949,000
4 Beds ⋅ 3 Baths ⋅ 1007687 MLS
Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and flexible spaces suited for a variety of needs. Outside, the property offers exceptional utility and open space with garage/workshop space, fenced areas, and room for equipment, hobbies, recreation, or agricultural use (buyer to verify permitted uses). Enjoy peaceful views, outdoor living areas, and the privacy of a substantial parcel while remaining within convenient reach of local shops, commuter routes, and area amenities. A rare opportunity to own a property with space, functionality, and endless potential

19 Bull Mine Road, Chester
$549,900
3 Beds ⋅ 2 Baths ⋅ 1008703 MLS
This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the living room ams the Primary have soaring cathedral ceilings and the dining room has a 10-ft. tray ceiling. Light pours into this homemaking the oversized living area bright and cherry. The inviting eat in kitchen features stainless appliances, and for extra storage a basement pantry features floor to ceiling shelves. There is also a basement laundry with included, oversized washer and dryer. An Additional laundry hook up is also available right outside the Primary suite. The living room has a fireplace clad in beautiful cultured stone with a wood burning insert for extra heat. Outside, mature landscaping frames this beautiful house. Enjoy relaxing on a two-tiered ,massive, low maintenance Trex deck surrounded by colorful perennial flowers that bloom every spring and summer. A stone fire pit sits center stage on the lower deck, and a large shed will hold all your gardening tool. In front a quaint porch provides more outside seating. There ia a garage and plenty of additional outdoor parking. The house has upgraded Hardie plank siding and stone. Enjoy country living and pace while still only being minutes from shopping, dining and the highway.

3318 State Route 94, Chester
$525,000
4 Beds ⋅ 3 Baths ⋅ 1004369 MLS
Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange Heritage Trail, local dining, and easy commuter access, this property is as practical as it is inviting. The main residence spans three spacious bedrooms and 1.5 baths, offering comfortable everyday living with room for the whole family. The private secondary suite features a bright one-bedroom, one-bath layout, ideal for in-laws, extended family, an au pair, or a long-term rental opportunity. Whether you're seeking to offset your mortgage or keep loved ones close while preserving everyone's privacy, this thoughtful configuration checks every box. With a 2,698 sq ft footprint, a full basement, attached garage, hardwood floors, central air, and a sweeping 0.56-acre lot with park views, this home combines classic charm with everyday function. Located in the Chester Union Free School District and just a short drive to Legoland, the Capelli Sports Complex, and Coach USA transit to NYC — 24 Walnut Street isn't just a home. It's a lifestyle. Opportunity like this doesn't last. Schedule your private showing today.

24 Walnut Street, Chester
$825,000
4 Beds ⋅ 4 Baths ⋅ MDQA2017378 MLS
Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

232 Evelyne St, Chester
$900,000
4 Beds ⋅ 3 Baths ⋅ 1002536 MLS
Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and excellent flow into the warm and welcoming family room with fireplace — ideal for both entertaining and everyday living. Formal living and dining areas provide additional space for gatherings and special occasions. The second level offers a large primary suite with vaulted ceilings, walk-in closet, and spa-style bath, along with spacious additional bedrooms and ample storage throughout the home. Step outside and enjoy the beauty and privacy of the expansive property surrounded by mature trees and peaceful natural scenery. Whether relaxing on the front porch, entertaining on the deck, or simply enjoying the open outdoor space, this property offers a true retreat-like setting. A rare opportunity to own a move-in-ready Colonial offering privacy, charm, and exceptional living space.

60 Whitetail Run, Chester
$894,000
3 Beds ⋅ 4 Baths ⋅ 000137 MLS
220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern touch. Full basement provides excellent storage space. Additional features include Central AC, original Andersen custom windows, and an attached 2-car garage. Step outside to a massive deck, spacious shed, and gorgeous landscaping set on a nice-sized lot. Conveniently located close to all amenities, this property offers privacy, space, and everything you could want in a home and more!

220 Oxford Road, Chester
$999,999
5 Beds ⋅ 3 Baths ⋅ 999261 MLS
A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5 bedrooms and 3.5 full baths. Luxury begins at the illuminated pillars lining the paver driveway, leading to a stone-accented front entry. Inside, sun-filled interiors highlight quality craftsmanship throughout. The two-story foyer features tray ceilings and expansive windows, while recessed lighting, built-in surround sound, and pre-wiring for a security system add comfort and functionality. The chef’s kitchen is a true centerpiece, featuring floor-to-ceiling custom cabinetry, granite countertops, a large center island with seating, and a premium Sub-Zero stainless-steel refrigerator. Adjacent casual dinette provides effortless flow for hosting, with sliding doors opening to the outdoor living areas which provide direct access to a deck & patio area. The oversized family room becomes the center of the home surrounded by windows and comforted by the fireplace. Upstairs, the primary suite offers a private retreat with two custom walk-in closets, a sitting area, and alcove. The en-suite bath features dual vanities, a walk-in shower with multiple shower heads, and a jetted soaking tub overlooking serene sunset views. Three additional bedrooms and one full bathroom are generously sized and thoughtfully arranged on the same level. Outdoors, the property delivers a resort-style experience, expansive open grounds framed by mature landscaping and stunning sunset views. The setting offers exceptional privacy and room to relax, entertain, or expand. Additional highlights include a three-car garage and a setting that perfectly balances tranquility with accessibility. This is a rare opportunity to enjoy luxury suburban living—where space, serenity, and elegance meet effortless access to New York City.

2 Garnett Hill Road, Chester
$785,000
5 Beds ⋅ 6 Baths ⋅ 995223 MLS
Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the expansive setting, inviting curb appeal, and peaceful surroundings that make this property truly special. Inside, the home features bright sun-filled living spaces, spacious entertaining areas, hardwood flooring, and a beautifully designed kitchen with abundant cabinetry, generous counter space, and an ideal layout for both everyday living and hosting guests. The warm and inviting family room with fireplace creates the perfect gathering space, while multiple spacious bedrooms and well-appointed baths provide comfort and flexibility for today’s lifestyle. Unique rustic-inspired bonus spaces add warmth, charm, and character throughout the home. Step outside to your own private outdoor oasis featuring expansive lawn space, pool area, multiple entertaining spaces, and scenic wooded surroundings offering year-round enjoyment and tranquility. A rare opportunity to own a property that offers privacy, character, and endless possibilities in one of the area’s most desirable locations. See it today and experience everything this exceptional home has to offer.

4 Debbie Court, Chester
$744,999
4 Beds ⋅ 3 Baths ⋅ 995624 MLS
Looking for a spacious home that has everything? Look no more! Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial offers over 3,300sqft of living space! The property offers four spacious sleeping areas and 2.5 baths. Endless possibilities for additional use continue on the 3rd floor with a 15 x 42 climate-controlled walk-up attic, offering approximately 630 additional square feet of space. Whether envisioned as a media lounge, home gym, creative studio, guest suite, game room, or finished living area, this expansive attic provides an incredible opportunity to customize the home to fit your lifestyle and needs. On the main level sun-filled living spaces showcase hardwood floors, recessed lighting, a striking stone fireplace, and an expansive family room with a pellet stove capable of heating the entire home. The spacious kitchen serves as the heart of the home, complete with granite countertops, abundant cabinetry, stainless steel appliances, double ovens, and direct access to the backyard for seamless indoor-outdoor living. Spectacular views, a fenced backyard, brand-new Trex deck, above-ground pool, and potential home office, make this property truly stand out. Abundant living space, flexible rooms, exceptional storage, newer major systems, outstanding outdoor amenities and exceptional curb appeal make this property the rare combination of comfort, functionality, and room to grow.

58 Nancy Lane, Chester
$1,145,000
9 Beds ⋅ 7 Baths ⋅ 995148 MLS
Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of one of the most significant equestrian properties in history. Gracefully set atop a scenic knoll on nearly three private acres in the heart of Chester, New York, the estate offers exceptional privacy while remaining just 40 miles from Manhattan. From the moment you arrive, the home's commanding presence, timeless architecture, and beautifully maintained grounds create an unforgettable first impression. The stately main residence features seven bedrooms and four-and-a-half bathrooms, where authentic Victorian craftsmanship has been meticulously preserved. Soaring ceilings, original hardwood floors, intricate millwork, marble fireplaces, elegant pocket doors, and exquisite architectural details reflect the grandeur of a bygone era, while thoughtful modern updates provide today's expected comforts. Designed for both elegant entertainment and everyday living, the home's expansive gathering spaces flow effortlessly to the surrounding grounds, creating an ideal setting for celebrations, family gatherings, or quiet evenings enjoying the beauty of the property. Adding to the estate's resort-style appeal is a separate pool house, complete with a full bathroom and private sauna, offering the perfect retreat for relaxation, wellness, or entertaining guests throughout the seasons. One of the property's most compelling features is its detached second residence, offering a beautifully appointed two-bedroom apartment with exceptional flexibility. Beyond providing luxurious accommodation for guests or extended family, this separate living space creates an outstanding opportunity for additional income. Whether utilized as a premium long-term rental, short-term vacation rental, executive housing, caretaker's residence, or owner's quarters while operating the main home as a hospitality property, it provides the versatility today's buyers are seeking. Beyond its architectural beauty, the property presents an exceptional opportunity to offset ownership costs through multiple revenue streams. This rare combination of a landmark residence and an income-producing secondary dwelling makes the estate equally attractive to homeowners, investors, and entrepreneurs. With its iconic history, breathtaking setting, and expansive layout, The Hambletonian House is ideally suited as a luxury bed and breakfast, boutique inn, private event venue, executive retreat, or premier destination rental—offering limitless possibilities for both lifestyle and investment. The current owner has invested extensively in preserving the estate's historic integrity while making significant improvements to major mechanical systems and the roof, ensuring modern reliability without compromising its timeless character. This careful stewardship allows the next owner to enjoy the confidence of updated infrastructure while preserving a truly irreplaceable piece of history. Ideally located near the shops, restaurants, and conveniences of the Village of Chester, with easy access to major highways and the best of the Hudson Valley, the property offers the perfect balance of peaceful country living and metropolitan accessibility. Properties of this significance rarely become available. Combining rich history, exceptional architecture, income-producing potential, and an irreplaceable legacy, The Hambletonian House represents a once-in-a-generation opportunity to own one of the most celebrated equestrian landmarks. Some homes are purchased. Others become part of history. This is one of them.

19 High Street, Chester
$527,900
4 Beds ⋅ 4 Baths ⋅ VACF2001486 MLS
Beautiful Single-Family Home in Much Desired Location. New Carpet, Fresh Paint, Re Finished Hardwood Floors, Upgraded Counter Tops, Primary Bath, Walk in Closet(s). Fully Finished Walkout Basement. Must See!

13100 Rockridge Rd, Chester
$849,900
4 Beds ⋅ 3 Baths ⋅ 991517 MLS
Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining. Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and elegant feel. The thoughtfully designed kitchen is perfect for cooking, gathering, and hosting. Outdoors, enjoy your own private retreat with an above-ground pool, play area, and a beautiful, wooded setting. With over 18 acres, the land offers exceptional privacy, natural beauty, and a peaceful buffer around the home. A rare opportunity to own a spacious Colonial with room to live, relax, and entertain—inside and out. Schedule your private showing today!

2 Primrose Lane, Chester
$3,400,000
4 Beds ⋅ 4 Baths ⋅ 988789 MLS
Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise. Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional. What truly sets this property apart is the lifestyle it delivers. A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence. Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home. Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley’s most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that is both active and refined. This is more than a residence. It is a fully realized compound, private, efficient, and architecturally significant, built for someone who values time, discretion, and a level of living that cannot be replicated.

19 Greentree Lane, Chester
$559,000
3 Beds ⋅ 3 Baths ⋅ MDQA2016908 MLS
Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built by Lundberg Builders, perfect for relaxing or entertaining. The home sits adjacent to community open space, offering added privacy with no direct neighbor next door. Inside, you’ll find hardwood flooring and an open-concept layout designed for modern living. The living room flows seamlessly into the dining area and kitchen, which features granite countertops, stainless steel appliances, and a beautiful tile backsplash. Sliding doors off the dining area lead to the composite deck and a lush, partially fenced yard, creating an ideal space for indoor-outdoor living. The kitchen also provides convenient interior access to the attached one-car garage. Upstairs, the primary suite offers a well-appointed bath, two additional bedrooms, a second full bath, and a laundry room for added convenience. Located just one mile from Route 50 on Cox Neck Road, this home offers quick access to shopping, dining, commuter routes to Washington DC and Baltimore, and the Chesapeake Bay Bridge. The intimate Waterman’s Cove community consists of just nine homes, with HOA services that include lawn care and trash removal - making for easy, low-maintenance living. Enjoy the peaceful lifestyle of Maryland’s Eastern Shore, with water views and privacy in a highly convenient location.

126 Watermans Cove Ln, Chester
$1,100,000
5 Beds ⋅ 4 Baths ⋅ 986225 MLS
Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene landscape, creating a truly one-of-a-kind backdrop. A dramatic entry introduces the home with soaring ceilings and heated marble floors, setting the tone for the refined interiors throughout. The layout flows effortlessly into expansive formal living and dining spaces, ideal for both everyday living and entertaining. At the heart of the home is a thoughtfully designed chef’s kitchen featuring premium appliances, custom stone and tile finishes, a gas range with griddle, double ovens, and an oversized two-tier island with prep sink. A walk-in pantry and elegant butler’s area provide both function and style. The family room is a standout space, offering scale, natural light, and architectural character, making it the perfect gathering area. Designed with entertaining in mind, the outdoor living experience is just as impressive, complete with a full stone kitchen and bar, a spacious stamped concrete patio, and a private hot tub retreat, all surrounded by custom masonry. Upstairs, the primary suite serves as a private sanctuary with its own balcony and spa-inspired bath featuring a soaking tub, custom shower setup with steam capability, and refined finishes throughout. Additional bedrooms are generously sized, offering comfort and flexibility for guests or extended living. The fully finished lower level expands the living space with a recreational area, full gym, and wet bar, perfect for hosting or unwinding. Throughout the home, hardwood flooring, an integrated sound system, and high-efficiency construction with spray foam insulation and multiple heating zones enhance both comfort and performance. Completing the property is a spacious three-car garage, a beautifully maintained yard with room to enjoy, and infrastructure already in place for a future gated entrance. A truly exceptional offering where design, privacy, and lifestyle come together seamlessly.

53 Gibson Hill Road, Chester
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