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$199,000
4 Beds ⋅ 1 Baths ⋅ PADE2123340 MLS
Step into this beautifully refreshed 4-bedroom bungalow in Chester Township, where modern updates meet a thoughtful, easy-living layout. From the moment you arrive, the three-car driveway and fully fenced yard set the stage for a home that is as functional as it is inviting. Inside, the living room welcomes you with durable, stylish LVP flooring that flows seamlessly toward the heart of the home. The kitchen is a true standout, boasting sleek granite countertops, a classic tile backsplash, and a brand-new stainless steel appliance package that’s ready for your first meal. Just off the kitchen, the sunroom serves as a bright, versatile space—perfect for a sunny dining area or a cozy spot to relax with a morning coffee. Convenience is key here, with two bedrooms and a dedicated laundry closet located right on the first floor. Upstairs, you’ll find additional bedrooms featuring brand-new carpeting and ample closet space throughout to keep everything organized. With ceramic tile in the high-traffic areas, central air and fresh finishes top to bottom, this home is truly move-in ready.

3006 Carter Ave, Chester
$339,900
2 Beds ⋅ 1 Baths ⋅ 1046033 MLS
Discover the charm of 18 Schueler Road, an inviting 2-bedroom, 1-bath home in the Monroe-Woodbury School District. Tucked along a private road with a road maintenance agreement in place, this cozy home offers a peaceful Hudson Valley setting. Step inside to a comfortable living space and an adorable, colorful kitchen that brings warmth, personality and character to the home. Two bedrooms and a full bath complete the easy-to-manage layout. The recently re-stained exterior adds to the home’s fresh, well-cared-for appeal. Conveniently located near shopping, dining, recreation and major commuter routes, 18 Schueler Road is a charming opportunity for first-time buyers, those looking to simplify, or anyone searching for a home with personality and room to make it their own.

18 Schueler Road, Chester
$779,900
4 Beds ⋅ 3 Baths ⋅ 1050193 MLS
PRIVATE WOODED COLONIAL!! 4 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Pantry! Master Bedroom Suite with Walk In Closet! Living Room with Wood Burning Fireplace & Built-Ins! Large Formal Dining Room with French Doors! Crown Molding! Gleaming Hard Wood Floors! Recessive Lighting! Walk Up Attic & Full Basement for Endless Possibilities! Two Story Entry/Foyer! Deck with Beautiful Awning! Over Sized Driveway for Plenty of Parking! Perfect Commuter Location! Close to Major Highways, Buses & Shopping!

1168 Craigville Road, Chester
$525,000
2 Beds ⋅ 2 Baths ⋅ 1050131 MLS
Welcome to Chester, NY!! Come see this spacious home featuring 2 bedrooms and 2 full baths, with a bonus room. This home has plenty of possibilities and includes a finished basement and finished attic for all your storage needs. Large 2-car garage for all the gadgets. This home has a large open concept for entertaining family and friends. Additional energy saving feature of solar panels and an oversized deck with an above-ground pool for outdoor enjoyment for all. The home boasts charm and beautiful hardwood flooring throughout many areas of the home. This home is conveniently located near shopping, fine dining, and many leisure activities for all age groups. Easy commute to the city and major transportation hubs for commuters. Local highway and interstate access within minutes. This is a property you want to see; come see what Meadow Av has to offer. Welcome Home!!!

19 Meadow Avenue, Chester
$499,000
3 Beds ⋅ 3 Baths ⋅ 1049026 MLS
This beautifully updated Chester home in the Monroe-Woodbury School District sits on 1.5 acres with a level open yard, a creek, and a wooded backdrop. From the moment you arrive, the paver walkway, landscaping, and inviting curb appeal set the tone. Inside, the main level boasts hardwood floors and an open layout with a brand-new kitchen featuring white cabinets, granite counters, and stainless steel appliances, plus a living and dining area with sliding glass doors to the deck and backyard. The first floor also has a full hallway bath and three bedrooms, including a bright primary suite with custom windows, crown molding, and an updated ensuite bath with custom tile and glass shower doors. The lower level offers a large den with a stone fireplace and wood-burning stove insert, a half bath, laundry room, and access to the attached two-car garage. Outdoor spaces include a deck off the kitchen and a covered deck from the den, perfect for relaxing or entertaining. The expansive yard is ideal for recreation, gardening, or gatherings, with the creek and woods adding privacy. Just 57 miles to NYC, this home offers both tranquility and easy access to amenities, including nearby parks with 1,500 acres of trails, playgrounds, and more. Additional perks include central air, newer siding, roof, oversized energy-efficient windows, shed, oil burner, hot water heater, and several updated appliances. Conveniently located near shopping, major highways and public transportation.

264 Bull Mill Road, Chester
$789,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018418 MLS
Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

402 Macum Creek Dr, Chester
$879,000
4 Beds ⋅ 4 Baths ⋅ 1048079 MLS
Welcome to 101 Beverly Road, a beautifully renovated 4-bedroom, 2 full and 2 half bath home offering approximately 3,764 square feet of total finished living space on 1.9 private acres in the Warwick Valley School District. Backing to woods for added privacy and a peaceful setting, this move-in-ready home combines generous living space, thoughtful updates and wonderful indoor-outdoor living. The heart of the home is the renovated kitchen, featuring quartz countertops, under-cabinet lighting and a built-in mini wine refrigerator. Wood flooring creates a warm, cohesive feel throughout the living spaces, while built-in speakers in the kitchen and living room are perfect for everyday enjoyment and entertaining. French doors further enhance the home’s inviting atmosphere and connection to the outdoors. The spacious primary suite includes a walk-in closet and beautifully renovated bath with a soaking tub and separate walk-in shower, creating a comfortable private retreat. Three additional bedrooms provide plenty of flexibility for guests or home-office space. A dedicated laundry room adds everyday convenience. Approximately 900 square feet of finished lower-level space expands the home’s possibilities even further. Complete with an added half bath and walk-out access to a stamped-concrete patio, this level is ideal for a recreation room, media space, home gym, playroom, office or additional entertaining area. Outside, enjoy 1.9 acres backing to woods, providing privacy and a beautiful natural backdrop. An aboveground pool and deck create the perfect setting for summer days and gatherings, while stamped-concrete walkways and patio areas extend the outdoor living space. An asphalt driveway leads to the attached two car garage. The home has also been extensively improved with many of the major updates already completed, including a new roof, vinyl siding, vinyl windows, garage doors and a new 200-amp electrical panel. A new ducted high-efficiency heat-pump system provides heating and central air conditioning for year-round comfort. Additional improvements include a Marathon non-metallic electric water heater and a whole-house water filtration and softening system with UV treatment. With its renovated interior, spacious layout, finished walk-out lower level, private wooded setting, pool and extensive major-system improvements, 101 Beverly Road offers the space and amenities to enjoy from day one—all within the Warwick Valley School District.

101 Beverly Road, Chester
$459,000
4 Beds ⋅ 2 Baths ⋅ 1047996 MLS
Welcome to this charming 4-bedroom, 2-bath bilevel, ideally situated on a quiet dead-end street. The inviting open floor plan offers a seamless flow for everyday living and entertaining, with beautiful hardwood floors throughout the main level and a spacious kitchen featuring stainless steel appliances. Enjoy year-round comfort with central air and take advantage of the large deck overlooking a flat, fully fenced backyard, providing the perfect space for outdoor entertaining, relaxing and play. With Monroe-Woodbury Schools, low taxes, and an excellent commuter location, this home offers the ideal combination of comfort, convenience, and value. Don’t miss the opportunity to make this wonderful home your own!

8 Townsend Place, Chester
$679,000
4 Beds ⋅ 4 Baths ⋅ 1046418 MLS
Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester
$550,000
5 Beds ⋅ 4 Baths ⋅ MDQA2018594 MLS
Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors throughout. The entry-level bedroom offers convenience, while the walk-in closets provide ample storage. Step outside to your personal oasis with an in-ground pool (new pool pump), ideal for summer relaxation and entertaining. With a generous 0.39-acre lot and side-entry garage, this home combines space and style.

326 Castle Marina Rd, Chester
$639,990
2 Beds ⋅ 2 Baths ⋅ MDQA2018602 MLS
Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area offers a spacious and functional space for lounging. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

641 Warbler Way, Chester
$350,000
2 Beds ⋅ 2 Baths ⋅ MDQA2018584 MLS
Your Island Getaway Is Waiting! Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for! Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the laid-back Island lifestyle. Inside the spacious living room features a wood stove, creating the perfect spot for cozy winter nights. The bright, well-appointed kitchen offers a center island, granite countertops, stainless steel appliances, abundant cabinetry, and a pantry—plenty of room for preparing family meals or entertaining friends. Just off the kitchen, the screened porch is ready for three-season enjoyment. Imagine crab feasts with family and friends, relaxing evenings, or cheering on your favorite team while enjoying the crisp fall air! Outside, the huge, privately fenced rear yard offers plenty of space for the kids to play, pets to roam, or everyone to gather. Multiple sheds provide convenient storage for all your crabbing, fishing, boating, and outdoor gear. Upstairs, you’ll find two spacious bedrooms plus a walk-up attic with endless possibilities. Use it for additional storage, a home office, hobby space—or transform it into an additional bedroom to suit your needs. Whether you’re looking for a year-round home, a weekend retreat, or your own slice of Island living, this one offers comfort, space, charm, and plenty of potential at a great price. PLUS...the boat ramp is just 2 mins away which means fresh seafood is what's for dinner! Come see it for yourself—this Island gem won’t last long!

200 Church St, Chester
$930,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018566 MLS
Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, custom window shades and a beautiful stone propane fireplace. The kitchen showcases K. Hovnanian's upgraded Looks package with crisp white cabinetry and upgraded Thermador appliances, complemented by reverse osmosis at the kitchen sink and a whole-house water filtration system. Additional features include a Rinnai tankless water heater, two-zone HVAC with propane backup and a whole-home surge protector. Outdoor living is ready to enjoy with a paver patio, propane grill hookup, irrigation system and upgraded landscaping—no waiting for a new yard to grow in or projects to be completed. Best of all, the location puts the Four Seasons lifestyle right outside your door. Enjoy easy access to the community's pickleball courts, clubhouse, indoor and outdoor pools, fitness center, walking trails, pier, kayak launch and more. Why wait to build when you can move right into a nearly new Kerr with the premium lot, upgrades, landscaping and finishing touches already done? 275 Warbler Way delivers exceptional value and an easy, move-in-ready Eastern Shore lifestyle.

275 Warbler Way, Chester
$400,000
5 Beds ⋅ 4 Baths ⋅ MDQA2018570 MLS
List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the Chesapeake Bay Bridge, this property combines generous proportions with a layout designed for comfortable everyday living and entertaining. The main level makes an immediate impression with 12-foot ceilings and oversized 6-foot windows, creating bright, open living spaces throughout. The floor plan includes a spacious family room, vaulted morning room, sunroom, and an eat-in kitchen that serves as the heart of the home. The kitchen is equipped with granite countertops, a large center island, pantry, and ample cabinet and workspace. The home’s 5-bedroom, 3.5-bath configuration provides plenty of flexibility. The primary suite features a tray ceiling and private bath with a custom-tiled shower and double vanity. Four additional bedrooms are complemented by two Jack-and-Jill-style bathrooms, offering a functional arrangement for family, guests, home offices, or additional flex space. Outdoor living is another highlight, with an impressive 800± square-foot wraparound deck providing plenty of room for grilling, dining, entertaining, and relaxing. Additional features include: • Hardwood and tile flooring • Roman blinds and wood shutters • New HVAC system • Finished garage • Dedicated laundry room with New washer and dryer • Approximately 4-foot crawl-space ceiling height • Numerous custom builder upgrades • No HOA With its impressive bedroom count, expansive living areas, oversized deck, substantial storage, and convenient Chester location, 1868 Roberta Drive offers bidders a unique opportunity to purchase a custom Eastern Shore home and make it their own. Don’t miss your opportunity to bid!

1868 Roberta Dr, Chester
$1,250,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018534 MLS
Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality. Inside, you'll find a dedicated home office and stylish engineered hardwood and tile flooring throughout, creating a seamless and low-maintenance living space. Large windows invite natural light and showcase the home's tranquil waterfront setting. Outdoor living is just as impressive, featuring two maintenance-free decks, a patio ideal for grilling and entertaining, and a fenced backyard perfect for pets, play, or simply enjoying the beautiful surroundings. Whether hosting friends or relaxing with a morning coffee, this home offers multiple spaces to take in the peaceful water views. Boating enthusiasts will appreciate the private pier equipped with both water and electric service, while the pier decking was replaced last year, providing added value and peace of mind. Enjoy easy access to boating, fishing, crabbing, kayaking, and all the activities that make waterfront living so special. Conveniently located on Kent Island near shopping, dining, marinas, and commuter routes, this exceptional waterfront property offers the perfect blend of luxury, comfort, and Chesapeake Bay lifestyle. 3 Bedrooms | 2.5 Baths | Main-Level Primary Suite | Separate Office | Waterfront on Cox Creek | Private Pier with Water & Electric | New Pier Decking (2025) | Two Maintenance-Free Decks | Grilling Patio | Fenced Backyard | Renovated Approximately 4 Years Ago

1717 Harbor Dr, Chester
$279,900
3 Beds ⋅ 1 Baths ⋅ PADE2122184 MLS

920 E 20th St, Chester
$365,000
3 Beds ⋅ 2 Baths ⋅ VACF2001632 MLS
Nestled in the quiet Mistwood Forest neighborhood, this charming home offers comfort, space, and convenience. The main level features a large primary bedroom with a private bathroom, beautiful hardwood floors, a spacious laundry room, and an open-concept kitchen and dining area—perfect for everyday living and entertaining. The home also offers generously sized bedrooms, two-zone heating and cooling, multiple attics, and abundant storage throughout. Enjoy your morning coffee surrounded by natural light in the inviting Florida room or relax on the large rear deck overlooking the expansive, fully fenced backyard. Conveniently located just minutes from shopping, dining, and everything Chester has to offer, this wonderful home is ready for its next owner. Don’t miss your opportunity to make it yours!

14519 Sonnenburg Dr, Chester
$374,900
3 Beds ⋅ 2 Baths ⋅ 1044316 MLS
UNLOCK UNLIMITED POTENTIAL IN WARWICK VALLEY SCHOOLS! Are you ready to stop renting, build instant equity, and design your dream home from the ground up? This hidden gem off Gibson Hill Road is your golden ticket into one of Orange County’s most desirable school districts at a rare and unbeatable entry-level price! Whether you are a savvy investor looking for your next high-margin flip, a contractor seeking a prime project, or a first-time homebuyer eager to earn serious sweat equity, the upside potential here is off the charts! Nestled in a peaceful setting with a shared private access setup off well-maintained Speranza Ct, you get the perfect balance of serene rural living with easy access to regional commuter routes, local dining, shopping, and wineries. Set on an acre of private, flat land, this 3 bedroom bi-level is a handyman special. Bring your contractor, bring your measuring tape, and bring your inspiration—roll up your sleeves and transform this structure into a showstopping countryside retreat! Property is being sold AS-IS. Bring your offers and turn your homeownership vision into reality today! No gov't loans due to condition.

260 Gibson Hill Road, Chester
$1,685,000
6 Beds ⋅ 8 Baths ⋅ 1043860 MLS
Welcome to 69 Cedar Pond Lane. Perched to capture panoramic mountain views, this expansive Chester estate offers an extraordinary combination of multi generational living, proven Airbnb and rental income potential, and top tier infrastructural upgrades across three fully finished levels. The first floor and its bright living & seamless entertaining sun drenched interiors greet you with soaring skylights and massive picture windows framing panoramic mountain views. The open living and dining layout centers on a wood-burning fireplace, flowing into a chef’s kitchen featuring new countertops, custom tile backsplash, breakfast bar, dining nook, built in wine rack, new refrigerator, dedicated beverage fridge and so much more. This floor features two bedrooms and 2.5 bathrooms, with direct walkout access to an expansive outdoor patio outfitted with an outdoor bar, fireplace, and lounge seating. On the second floor you're greeted to a luxury primary suite & a private in law apartment. The upper level hosts three bedrooms, highlighted by a primary suite with mountain vistas, a walk in closet, and a spa bath with dual vanities, a deep soaking tub, stand up shower, and private water closet. This floor also features a dedicated second kitchen, living room, and private patio access. Thoughtfully updated with new countertops, a built in electric fireplace, and an integrated media center, this wing easily functions as an independent, fully equipped apartment. Downstairs is a guest suite & hidden speakeasy. Designed for recreation and flexible guest accommodations, the walkout lower level features a large open playroom created by opening the main space, complemented by a kitchenette, new carpeting, and updated tile. This level includes an Airbnb ready bedroom, finished laundry room, a newly added half bath, and an additional versatile flex room ideal for a home gym, private office, extra bedroom, or mudroom. Concealed discreetly behind a custom bookshelf lies a finished secret room with an adjacent full bathroom, perfect for a private lounge, speakeasy, or creative studio. Unwind in the private hot tub positioned to the right of the home, gather around the backyard fire pit, or enjoy the upper driveway area landscaped with a dedicated children's playset and seating area. The backyard has already been scoped for a custom in ground pool, with renderings available by seller. Additionally, the lower lot can be subdivided and built on, with electrical infrastructure already set up. The property includes a high efficiency HVAC system, commercial grade well pump, and dual water heaters installed in 2025. The roof was replaced around 2022. Ceiling fans and skylights are installed throughout, and all interior wallpaper is high quality peel and stick for effortless design customization. Whether you are looking for a spacious family home, a turn key rental retreat, or a property with room to build and expand, 69 Cedar Pond Lane has it all. Schedule your private tour today and see everything this one of a kind home has to offer.

69 Cedar Pond Lane, Chester
$569,900
4 Beds ⋅ 3 Baths ⋅ MDQA2018296 MLS
OPEN SUNDAY 11AM-1PM. Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details throughout including crown molding, chair rail, and wainscoting. The gourmet kitchen is the heart of the home, showcasing silestone countertops, stainless steel appliances, under-cabinet lighting, ceramic tile backsplash, a spacious island, and additional cabinetry and countertop space adjacent to the pantry. The separate breakfast area features a new sliding glass door (2025) leading to the private fenced backyard, complete with a Trex/Vinyl deck (2015), shed, extensive hardscape, and beautifully landscaped grounds. The inviting family room features a floor-to-ceiling stone gas/propane fireplace (2018) and adjacent office/storage area. Renovated main-level powder room with updated vanity and lighting (2020), laundry room with Closet America cabinetry and access to attached two-car garage with epoxy flooring (2024) and insulated, finished walls (2025). OWNER IS WILLING TO REMOVE STAIR LIFT TO UPPER LEVEL AND REPLACE WITH CARPET ON STAIRCASE. On the upper level, you'll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bathroom featuring dual granite vanities and a large walk-in shower. The renovated hall bathroom offers updated ceramic tile, a quartz vanity, and tub/shower combination. The second floor and stairway have also been freshly painted. Additional highlights include updated hallway, foyer, and kitchen lighting, brushed nickel door hardware and hinges throughout. The home also features 6" gutters and downspouts with gutter guards (2023), asphalt roof replaced in (2018), and driveway torn out and replaced/sealed (2024/2026). Clayborne Woods is a private neighborhood that offers a jog/walk path, community management, and trash service. Enjoy the best of Kent Island living with a location just minutes from the Chesapeake Bay Bridge, beaches, parks, boat ramps, marinas, waterfront dining, shopping, restaurants, and schools. This exceptional home combines comfort, convenience, thoughtful updates, and coastal charm. Come see for yourself what Kent Island living is all about!

233 Cross Creek Ct, Chester
$749,000
4 Beds ⋅ 3 Baths ⋅ 1042913 MLS
Imagine coming home to a beautifully maintained and upgraded property designed for comfort, entertaining, and enjoying the outdoors. This home features a high-ceiling foyer flooded with natural sunlight, a granite kitchen with a tiled backsplash, a gas fireplace, extra living and dining room space, 9-foot ceilings, hardwood flooring, and central AC throughout. Step outside to an oversized double deck offering a breathtaking view from the 1.4-acre property, complete with an above-ground pool and cozy hot tub. Recent updates include new flooring in 3 bedrooms. A two-car garage and driveway provide ample parking. The home CURRENTLY OPERATING AS AN AIRBNB with approximately $70,000 in annual revenue after Airbnb fees. The sale includes all furniture, appliances, kitchen housewares, and all TVs, offering a truly move-in-ready opportunity with the option to seamlessly continue the existing rental use. Conveniently located near Lowe’s, ShopRite, The Castle Fun Center, and major highways, and very close to Legoland. Don’t miss this unique opportunity!

121 Conklingtown Road, Chester
$550,000
3 Beds ⋅ 2 Baths ⋅ 1042882 MLS
Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an effortless connection to the serene backyard perfect for relaxing, entertaining, or enjoying the surrounding nature. The spacious primary suite features a huge closet and a private master bath. Two additional bedrooms offer generous closet space, providing plenty of room for family, guests, or a home office. Step outside and cross the charming bridge over the stream to access the enlarged backyard, offering even more space to enjoy the outdoors. A spacious 24' x 28' detached garage with a 10' x 10' garage door provides ample room for large vehicles, ATVs, a workshop, equipment, and storage. Conveniently located just minutes from Route 17, shopping, restaurants, and everyday amenities, this property offers the perfect blend of country tranquility and convenient access to town.

50 Hambletonian Avenue, Chester
$635,999
3 Beds ⋅ 3 Baths ⋅ 1041906 MLS
If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of finished living space, offering room for everyone and every lifestyle. Set on approximately 2 acres and conveniently located near schools, shopping, and transportation, this home delivers the perfect combination of space, flexibility, privacy, and convenience! Step inside to a bright, open-concept main level with soaring vaulted ceilings, a welcoming living room with fireplace, and a dining area featuring custom lighting. The beautifully appointed kitchen offers granite countertops, breakfast island, stainless steel appliances, and direct access to the spacious back deck—perfect for effortless indoor/outdoor entertaining. Three bedrooms are located on the main level, including a spacious primary suite with vaulted ceiling, wall-to-ceiling closets, hardwood floors, and abundant natural light. Two additional bedrooms and convenient main-level laundry complete the first floor. The fully finished lower level is a true bonus, offering endless possibilities with LVP flooring, custom built-in shelving, walk-out access, entertainment space, family room/den, and a bonus room currently used as an office that could easily serve as a guest room or additional sleeping space. A full bath with custom vanity and tiled shower makes this level ideal for guests, extended living, hobbies, or working from home. Outside, enjoy a sprawling yard, mature landscaping, circular driveway, and plenty of room to play, relax, and entertain. The spacious back deck and hot tub create the perfect private retreat. Space, style, flexibility, and location—all in one exceptional property. This is the one you’ve been waiting for!

3561 Rte 94, Chester
$699,000
5 Beds ⋅ 4 Baths ⋅ 1041722 MLS
Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful, wooded setting. From the inviting covered front porch, step inside to spacious, light-filled rooms that blend comfort and elegance. Rich hardwood floors, soaring ceilings, abundant windows, and a beautiful stone fireplace create a warm and welcoming atmosphere. The heart of the home is the expansive open kitchen, featuring modern appliances, generous cabinetry, and plenty of counter space, making it ideal for everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, offering both open gathering spaces and cozy nooks. Five generously sized bedrooms provide flexibility and room for everyone. Enjoy the outdoors from the extensive decks overlooking the mature, wooded surroundings, complete with a charming koi pond that adds to the property's peaceful, natural setting. Whether enjoying morning coffee, entertaining guests, or simply unwinding, this outdoor space offers a tranquil retreat. Adding exceptional versatility, a separate approximately 800-square-foot building offers endless possibilities as an art studio, workshop, private office, creative space, or whatever best suits your needs. With its combination of generous living space, distinctive character, privacy, and flex outbuilding space, this property offers a truly special place to call home.

65 Oxford Springs Road, Chester
$669,000
3 Beds ⋅ 3 Baths ⋅ 1040801 MLS
Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities. Conveniently located near shopping, restaurants, and all that the Hudson Valley has to offer, and located in the Warwick School District. A wonderful opportunity to make this colonial your new home!

173 Creamery Pond Road, Chester
$750,000
4 Beds ⋅ 3 Baths ⋅ 1041533 MLS
Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal. Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious kitchen features custom cabinetry, granite countertops, and a custom wine rack with wine fridge, creating a stylish and functional space for everyday living and entertaining. The main level includes a bedroom and full bath for added flexibility, while the spacious primary bedroom offers a private ensuite full bath. The lower level provides additional finished living space with plenty of flexibility for a recreation room, home office, gym, media area, or other needs. Additional interior features include surround sound and smart thermostats. The attached 2-car garage includes an EV charger, while the property also features solar panels leased through Sunrun and a backup generator. Additional highlights include spray foam insulation, central air, on-demand hot water, and forced-air propane heating. Located in a desirable Chester setting, this home offers convenient access to shopping, dining, parks, major roadways, and commuter routes, providing a comfortable setting with everyday convenience.

1 Sanford Avenue, Chester
$899,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018244 MLS
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add modern convenience throughout. The kitchen has been refreshed with new KitchenAid appliances, backsplash, under-cabinet lighting, updated fixtures and hardware, a new exhaust fan and disposal, instant hot water, and an enhanced pantry with pull-out storage. Just beyond, the mudroom adds both charm and function with brick flooring and Pottery Barn built-ins. The primary suite feels like a private retreat, featuring a completely renovated bath with a custom vanity, Kohler fixtures, and a luxurious BainUltra spa tub with chromatherapy lighting, along with added built-in closet storage. The guest bath and powder room have also been beautifully updated, while the laundry room features new cabinetry, luxury vinyl flooring, and a new GE washer and dryer. Outside, enjoy a private setting backing to trees and a quiet rear alley. Extensive professional landscaping, a drip irrigation system, landscape lighting, new pergola, and added deck railing create an inviting outdoor space for relaxing or entertaining. Even the garage has been thoughtfully upgraded with an EV charger, Elfa shelving, motion-detected lighting, fresh paint, and a GE refrigerator. Located in Gibson’s Grant, one of Kent Island’s most desirable waterfront communities, residents enjoy picturesque streets, walking trails, a community pool and clubhouse, waterfront pavilion, fishing pier, kayak launch, and beautiful views of Macum Creek and the Chester River. With its extensive 2025 renovation, private setting, and coveted Gibson’s Grant location, 148 Elinor Street offers the rare opportunity to enjoy an established coastal community with the feel and finish of a newly designed home.

148 Elinor St, Chester
$475,000
4 Beds ⋅ 2 Baths ⋅ 1040785 MLS
Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors. Conveniently located close to shopping, dining, and major highways, this home offers a great combination of space, comfort, and accessibility. Don't miss the opportunity to make it yours!

32 Surrey Road, Chester
$819,900
3 Beds ⋅ 3 Baths ⋅ MDQA2018222 MLS
Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedroom enhanced by a three-foot extension. A first-floor study offers flexible space for a home office, den, or possible fourth bedroom. Thoughtfully designed and exceptionally well-maintained, the home offers numerous updates and features, including a new roof installed in 2026 with a transferable manufacturer’s warranty and a new kitchen completed in 2022 featuring GE Café appliances, including a professional 36” six-burner range with convection oven, an additional oven in the island, and an Advantium speed-cook microwave. The kitchen appliances are under warranty through February 2028. The Primary Bathroom was renovated in 2019 and features heated floors, an oversized shower, and a customized makeup vanity. A Rinnai tankless hot water system provides efficient, on-demand hot water. The main level features beautiful hardwood floors, a convenient half bath, motorized window blinds in the Family Room, and a Ring security system. The home also offers a spacious basement crawl space with convenient interior access, providing valuable additional storage for seasonal items and household belongings, as well as a water-powered backup sump pump for added peace of mind. Outdoor spaces are equally inviting, with a welcoming front porch, spacious rear deck, rear patio, fenced yard, and a propane quick-connect hookup on the deck for a grill, making outdoor cooking and entertaining easy and convenient. A rear-entry two-car garage with a three-car parking pad provides ample parking. The garage includes a refrigerator, a freezer with a warranty through October 2027, a storage system, and electric bike lift with an HDTV antenna mounted on the garage roof. Upstairs are two additional bedrooms and a full bathroom, while the finished room above the garage offers flexible living, office, hobby, or recreation space and features a split-system HVAC for year-round comfort. Enjoy all that Gibson’s Grant has to offer, including water access to Macum Creek and the Chester River, a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, and scenic open spaces. Ideally located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer, this exceptional home provides the perfect combination of quality construction, thoughtful updates, flexible living spaces, and a wonderful waterfront community lifestyle.

207 Thomas White Blvd, Chester
$839,000
4 Beds ⋅ 4 Baths ⋅ 1040485 MLS
Welcome to 34 Boville Court, a stunning, fully updated farmhouse colonial tucked away on a peaceful cul-de-sac and set on just shy of two acres. Thoughtfully designed with timeless style and modern functionality, this completely move-in-ready home offers an exceptional blend of space, comfort, and sophistication. Step inside to beautiful hardwood floors and a bright, inviting layout made for both everyday living and effortless entertaining. The beautifully updated kitchen is complemented by a butler’s pantry, offering additional storage and prep space while making hosting a breeze. Spacious living and gathering areas flow seamlessly throughout the home, creating the perfect setting for everything from intimate nights in to large celebrations. Upstairs, retreat to the impressive primary suite, along with generously sized additional bedrooms featuring beautiful cathedral ceilings that add character and an airy, elevated feel. The fully finished walk-out basement provides an entire additional level of versatile living and entertaining space, with direct access to the expansive property beyond. Set on nearly two private acres, there is plenty of room to relax, entertain, play, and enjoy the outdoors. Situated on a cul-de-sac, with gorgeous updates, a spacious floor plan, and picture-perfect farmhouse appeal, 34 Boville court is truly turnkey and ready to welcome its next owners home.

34 Boville Court, Chester
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