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$459,000
4 Beds 3 Baths 1039933 MLS
Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3 Bathrooms and sits on just under an acre of land. With a spacious kitchen, and both a designated living room and dining room, this home offers an easy-flowing layout, making you feel right at home the moment you walk through the door. Off the kitchen you will find a bonus room that can be transformed into a gym, playroom for the kids, entertainment room for guests or whatever your needs may be. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with its own full bathroom. Last but certainly not least, is the tranquility and calmness this property has to offer. As you venture outside, you will find yourself tucked away on a quiet road with an inviting backyard that has access to Cromline Creek! This offers the perfect setting for those early morning coffees or long days of entertainment . Add easy highway access, an easy commute to NYC, and proximity to shopping destinations like Woodbury Commons, and you've found a location that truly checks all the boxes. Schedule your showing today and make this beautiful home yours before the new school year begins!

63 Hubshop Road, Chester

$749,990
2 Beds 3 Baths MDQA2018316 MLS
Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. 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.

536 Warbler Way, Chester

$449,900
4 Beds 3 Baths VACF2001620 MLS
Beautifully Colonial freshly painted two-car garage home in the heart of Chester! The main level showcases refinished hardwood floors throughout. Elegant columns connect the crown-molded living room to the formal dining room, featuring a tray ceiling and additional crown molding. The eat-in kitchen offers granite countertops, a subway tile backsplash, pantry, new fixtures, gas cooking, stainless-steel appliances, and sliding doors leading to an expansive 24-by-10-foot, two-tier deck. The adjoining family room features a gas fireplace and crown molding, creating a comfortable, open-concept gathering space. A convenient half bath completes the first floor. Upstairs, carpeting extends throughout the hallway and bedrooms. The spacious primary suite features a tray ceiling, walk-in closet, and spa-inspired bathroom with tile flooring, a double vanity with granite countertops, a Jacuzzi tub, and a walk-in shower with tile surround. Bedroom two includes three windows, a sitting area, and a ceiling fan. Bedroom three also offers a ceiling fan, while the generously sized fourth bedroom features two closets, a ceiling fan, and its own sitting area. The hall bathroom includes a double vanity with granite countertops, tile flooring, and a tiled tub surround. A large laundry room with tile flooring and abundant shelving adds convenience. SCHEDULE SHOWINGS THROUGH SHOWINGTIME APP ON YOUR PHONE

3455 Ivyridge Dr, Chester

$440,000
3 Beds 2 Baths 1036770 MLS
Historic Colonial Era Home in the Heart of Sugar Loaf, NY. Located just 60 minutes from NYC. Zoned Residential/Commercial. Step into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Built in 1770, this unique property features:• One of a kind Colonial era home, featuring original exposed hand-hewn beams, barn siding walls, and a fireplace• Two spacious workshops/studios – ideal for artists, entrepreneurs, or makers – currently a woodcarvers workshop. • A must-see, living piece of history full of soul and story• Stunning view of Sugar Loaf Mountain right out your front door. Zoned commercial/residential, this home offers the perfect blend of live-work potential — ideal for a workshop, gallery, studio, or cozy retreat. Just steps away:• 2 popular restaurants• A vibrant performing arts center• Local breweries with live music• Coffee shop/ Roaster & Brunch House• Year-round craft markets & community events. Sugar Loaf is a renowned creative hub, and this home is at the very center of it all. Nestled in the heart of Sugar Loaf’s artisan community, this unique home and shop was long owned by a cultural mainstay — a woodcarver, painter, entertainer, and local luminary whose influence helped shape Sugar Loaf’s identity as an artists’ village back in the mid 1960’s.  This property offers more than walls and beams. Full of character and creative potential, this property is perfect for artists, craftsmen, woodworkers or anyone drawn to a vibrant, storied community. It offers a living canvas for makers and dreamers to carry forward a tradition of creativity. Don't miss your chance to own a timeless treasure in one of the Hudson Valley’s most beloved villages.

1367 Kings Highway, Chester

$749,900
4 Beds 4 Baths 1037562 MLS
20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange County within the Chester School District, this home offers space, privacy, and convenient access to shopping, dining, parks, recreation, commuter routes, and Hudson Valley attractions. Some listing photographs have been virtually decluttered and/or virtually staged for visualization purposes. Virtual furnishings shown are not included with the property. Come make it your own.

20 Mountainside Drive, Chester

$409,900
3 Beds 3 Baths VACF2001616 MLS
Welcome to this beautiful Higgins-built home, ideally situated on one of the largest and most picturesque lots in the Thornhill subdivision of Southbend. Set on an impressive 1.18-acre landscaped lot, this one-owner home offers a spacious party deck and a double-width paved driveway. Inside, the home’s pride of ownership is immediately apparent. The inviting living room features hardwood flooring, a vaulted ceiling, and a striking arched window. The formal dining room is enhanced by hardwood floors, crown molding, and a beautiful bay window. The spacious kitchen offers abundant cabinetry, ceramic tile flooring, and a coordinating tile backsplash. The family room includes hardwood floors, a built-in television niche, and a cozy gas fireplace. The generously sized primary suite features a recently renovated private bathroom, while the two additional bedrooms offer comfortable proportions, carpeting, and ceiling fans. Upstairs, a large hardwood-floored loft overlooks the living room and provides flexible space for a home office, media room, or sitting area. Lovingly maintained by its original owner, this exceptional home is conveniently located just minutes from Fort Lee, Richmond International Airport, shopping, and neighborhood schools around the corner SCHEDULE SHOWINGS THROUGH SHOWINGTIME APP ON YOUR PHONE.

304 Thornhill Dr, Chester

$799,000
4 Beds 3 Baths 1034771 MLS
This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the kitchen and family room, with a separate living room and formal dining room, plus laundry and a half bath. Upstairs, four bedrooms and two full baths provide ample space. The basement offers generous storage, and the 2-car garage completes the layout with a spacious driveway for multiple vehicles. The property is move-in ready with significant recent upgrades: oil furnace replaced October 2020, central air replaced June 2022, and a whole-house filter and water softener system installed April 2024. Propane gas serves the kitchen and dryer, while the fireplace has been converted to propane for convenience but retains the option to revert to wood burning. The home features a sub-panel electric system with manual transfer switch for seamless generator backup in the event of power outages. Located in a quiet Chester cul-de-sac with mountain and woodland views, the home is perfectly positioned for both primary residence and weekend getaway living. Just steps from the Heritage Trail system for outdoor recreation, and only minutes from Legoland, shopping, dining, and all area conveniences.

3 Garnett Hill Road, Chester

$924,000
3 Beds 3 Baths MDQA2018216 MLS
Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

214 Bayberry Dr, Chester

$289,000
2 Beds 1 Baths 1030923 MLS
Looking for the perfect weekend stay, peaceful getaway, or a one-of-a-kind place to call home? Step into the timeless charm of this historic 1800s farmhouse, where character, history, and a warm, inviting setting come together. Whether you envision weekends away from the hustle and bustle, a charming country retreat, or year-round living, this unique property offers an opportunity to own a true piece of history. Original details, classic craftsmanship, and the distinctive character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that reflects the home’s remarkable past. As is typical of homes built during this period, some ceilings, doorways, and stairwells are lower than modern standards, adding to the home’s authentic historic character and charm. If you’ve been searching for a weekend escape, a peaceful retreat, or a home filled with personality and a story to tell, this special farmhouse is ready for its next chapter.

166 Bull Mill Road, Chester

$605,000
3 Beds 2 Baths 1035387 MLS
Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The spacious dining area flows seamlessly into the heart of the home, a beautifully renovated kitchen designed to impress. Showcasing crisp white cabinetry, quartz countertops, a large farmhouse sink, stainless steel appliances, behind barn doors a large pantry and a stunning center island, this kitchen is perfect for both everyday living and entertaining. Enjoy casual meals in the bright breakfast area, which opens to a generously sized deck overlooking the peaceful backyard an ideal setting for morning coffee, outdoor dining, or simply relaxing in nature. Gleaming hardwood floors and recessed lighting add warmth and elegance throughout the main level. The spacious primary suite offers cathedral ceilings, two large closets, and plenty of room for a king-sized bed. Two additional generously sized bedrooms and a full bathroom complete the main level. Downstairs, you'll find a welcoming tiled family room with direct access to the porch and backyard, making indoor-outdoor living effortless. A versatile bonus room provides endless possibilities as a home office, gym, playroom, or guest space. The lower level also features a newly renovated full bathroom and a private laundry room. Outside, the expansive property is a true sanctuary, complete with an above-ground pool, playground, and plenty of open space to enjoy recreation, gardening, or peaceful evenings under the stars. Conveniently located for commuters and just minutes from the Hudson Valley's renowned wineries, breweries, restaurants, shopping, and outdoor recreation, this exceptional home offers the lifestyle you've been searching for. Come experience all the beauty and charm the Hudson Valley has to offer you'll be ready to call this one home.

412 Laroe Road, Chester

$475,000
3 Beds 2 Baths 1030740 MLS
Welcome to this impeccably maintained raised ranch in the highly sought-after Surrey Meadows Community. Upon entering the foyer, you'll find a practical area beneath the stairs, providing convenient storage for coats and shoes. The lower level features a spacious bedroom with access to a full bathroom, complemented by a versatile bonus room perfect for a cozy den or guest accommodation. Ascend the hardwood stairs to the living room, which boasts hardwood flooring and abundant natural light. This level also includes two generously sized bedrooms and an additional bonus room, ideal for a home office. Newly installed pocket doors maximize space. The fully renovated kitchen is a culinary enthusiast's dream, featuring hidden spice cabinets, a copper farmhouse sink, and a glass-door pantry. From the kitchen, step out onto the deck that overlooks a substantial yard. The home includes a convenient garage and a shed, ideal for storage or lawn equipment. Enjoy year-round activities such as Legoland Resort, artisanal eateries and wineries, orchards, and Orange County's recreational lakes. Within walking distance to both the Middle School and High School and approximately an hour's drive from New York City, with public transportation to NYC nearby. This residence is truly a must-see.

21 Trotting Drive, Chester

$862,750
3 Beds 2 Baths MDQA2018158 MLS
THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fastest growing 55+ community on Maryland's Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is the rear buffer and beautifully landscaped. If they have a dog, the common area next to the home is almost the size of a building lot offering exceptional privacy. FSKI club house offers resort quality from the indoor pool and gym or the outside pool in summer months. FSKI also allows you golf carts! Don’t miss this opportunity to experience resort style living at Four Seasons Kent Island.

320 Bayberry Dr, Chester

$1,100,000
3 Beds 4 Baths MDQA2018162 MLS
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. 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.

117 Flycatcher Way, Chester

$799,900
4 Beds 3 Baths MDQA2018144 MLS
Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester

$435,000
3 Beds 2 Baths 1033721 MLS
Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

66 Whitetail Run, Chester

$747,900
4 Beds 3 Baths MDQA2018154 MLS
Welcome Home!!! Open DAILY by Appointment - Or stop by one of our OPEN HOUSES***If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds.*** Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs of new construction (i.e. transfer tax split, etc). Designed for easy everyday living, the Simone model offers the convenience of having the majority of the home's daily living spaces on the main level. The gourmet kitchen, dining and living areas, screened porch, primary suite, second bedroom, office, full bath, and laundry are all thoughtfully located on the main floor. The stunning gourmet kitchen features crisp white cabinetry, a large center island, stainless steel appliances, wall oven/microwave combination, and propane gas range, flowing seamlessly into the light-filled dining and living areas. The living room is anchored by a cozy stone fireplace, while the screened porch provides a relaxing place to enjoy your morning coffee or unwind. The main-level primary suite features tray ceilings and a spa-inspired bath with dual vanities, a large walk-in shower, and an expansive walk-in closet. Upstairs, you'll find flexible bonus space including a spacious loft, two additional bedrooms, and a full bath, perfect for visiting family, hobbies, entertaining, or simply having extra space when you want it. **It's additional space when you need it, without requiring stairs for your everyday living.** The attached garage adds convenience and storage. Beyond the home, enjoy a resort-style lifestyle with incredible amenities including a 23,000-square-foot clubhouse, fitness center, indoor and outdoor pools, billiards, tennis and pickleball courts, community pier, outdoor bar, fire pit, and a full calendar of social activities. The nearby Cross Island Trail is perfect for walking, running, or biking, and you're just minutes from shopping, dining, and everything Kent Island has to offer.

209 Harrier Way, Chester

$868,000
4 Beds 3 Baths MDQA2018142 MLS
OPEN SUNDAY SEPT 20, 11;30;AM-1:30 PM--A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

$439,999
5 Beds 3 Baths VACF2001584 MLS
Charming cottage-style home on a private cul-de-sac with a spacious ½-acre lot! This beautifully maintained home blends timeless character with thoughtful modern updates. Featuring a detached garage with workshop space, concrete driveway, vinyl siding, thermal windows, and a large fenced backyard with a deck off the sunroom make this property truly special. Inside, you'll find original hardwood floors, solid wood doors, crown molding, custom built-in bookcases, and a cozy family room featuring a raised brick hearth and gas fireplace. The updated kitchen showcases new cabinetry, butcher block countertops, tile backsplash (2020), and Samsung Bespoke smart appliances (2024). The main-level primary bedroom offers convenient one-level living, while the large sunroom provides year-round enjoyment with its own HVAC, propane heater, and new carpet. Upstairs are four additional generously sized bedrooms and two baths. Recent improvements include HVAC (2021), Ecobee smart thermostat (2021), GE washer and dryer (2024), ceiling fans (2024), privacy fence (2025), new carpet in the primary bedroom and sunroom (2025), attic insulation (2026), front and storm doors (2026), and 10-year smoke/CO detectors (2026). The roof was replaced in 2009 with a 35-year warranty. With abundant storage, classic craftsmanship, and an exceptional list of updates, this move-in-ready home is one you won't want to miss!

5400 Karma Rd, Chester

$799,000
4 Beds 3 Baths 1012284 MLS
Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm and inviting family room with a fireplace, creating an ideal space for entertaining. The spacious kitchen is appointed with granite countertops, a center island, abundant cabinetry, and sliders leading to an expansive deck overlooking the peaceful backyard. A formal dining room, powder room, and first-floor laundry complete the main level. Upstairs, the generous primary suite features a private ensuite bath, while three additional bedrooms share a full hall bath. A walk-up staircase leads to a full-house unfinished attic, offering outstanding potential for future living space. The finished walk-out basement provides even more room to relax or entertain, with sliders opening to a covered patio. An oversized two-car garage and a huge storage shed provide exceptional storage and convenience. Ideally located in the highly sought-after Monroe-Woodbury School District, this exceptional home combines timeless Colonial charm, abundant living space, beautiful outdoor amenities, and endless possibilities in a peaceful Chester setting.

197 Oxford Road, Chester

$749,000
4 Beds 4 Baths MDQA2017930 MLS
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

$899,990
3 Beds 3 Baths MDQA2017958 MLS
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. 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.

532 Warbler Way, Chester

$929,990
3 Beds 3 Baths MDQA2017926 MLS
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. 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.

540 Warbler Way, Chester

$349,999
4 Beds 2 Baths 1024779 MLS
Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship. Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming atmosphere that highlights the home's authentic farmhouse appeal. Rich with historic charm and original details, this property is ready for its next owner to restore and make it their own. Enjoy peaceful, scenic views of the surrounding greenery while benefiting from a highly convenient commuter friendly location. Just minutes from the highway, downtown Chester, Goshen, Monroe, and Warwick, you'll have easy access to local shops, restaurants, parks, wineries, farmers markets, and everything the Hudson Valley has to offer. Priced with the home's restoration needs in mind, this is a rare opportunity to invest in a property with incredible potential, generous outdoor space, and an unbeatable location. Whether you're searching for a primary residence, weekend retreat, or renovation project, this farmhouse is ready to be brought back to life. Schedule your private tour today and imagine the possibilities!

241 Meadow Avenue, Chester

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