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$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

$250,000
PADE2117006 MLS
*Pics coming soon* INVESTMENT OPPORTUNITY: Prime Chester Property - Former Church Ready for Redevelopment! Unlock the potential of this substantial property at 3001 W 10th St, Chester, PA. This former church, encompassing 3,900 sq ft across two stories plus a basement, sits on a generous 8,496 sq ft lot, offering a unique opportunity for investors and developers. Imagine the possibilities! Currently configured with a large 50-foot sanctuary, kitchen, and half bath on the first floor, and three offices, a full bath, and storage on the second, the adaptable layout can be reimagined to suit a variety of purposes. The spacious lot provides ample potential for expansion or redevelopment. Key Features & Investment Highlights: Prime Location: Situated in Chester, this property benefits from [mention local amenities, transport links, or community features – research this and add specific details. E.g., "easy access to I-95," or "close proximity to public transportation"]. Substantial Size: 3,900 sq ft building with a full basement, providing significant usable space. Large Lot: 8,496 sq ft lot, offering room for expansion or redevelopment. Flexible Layout: Adaptable floor plan easily reconfigured for various uses (subject to zoning regulations). Development Potential: Explore options for converting to [suggest potential uses – e.g., "multi-family residential," "community center," "office space," or "recreational facility"]. It is the buyer's responsibility to verify zoning and permitted uses. Don't miss this chance to acquire a valuable property in a promising location. Schedule a showing and discuss the exciting potential of 3001 W 10th St!

3001 W 10th St, Chester

$675,000
4 Beds 3 Baths 1009848 MLS
Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal dining room, and family room anchored by a floor-to-ceiling stone fireplace. Large windows throughout the main level bring in an abundance of natural light, creating a bright and open feel throughout the home. The eat-in kitchen is designed for both everyday use and entertaining, offering generous cabinet and counter space, a center island, and an open layout that connects well with the rest of the home. French doors lead directly from the kitchen to the rear deck, which was updated within the last two years and provides plenty of room to enjoy the outdoor setting. The first floor also features a large pantry and laundry area with an impressive amount of cabinetry and storage, along with a full bathroom for added convenience. Upstairs, you'll find four bedrooms and two full bathrooms, including a spacious primary suite. The basement offers an incredible amount of additional space and storage that truly needs to be seen in person to be appreciated. Throughout the home, there is no shortage of storage or usable living space. Outside, the property provides a mix of open yard and mature trees across 3.2 acres, offering plenty of room to enjoy the outdoors. An existing in-ground pool is also located on the property and is being sold as-is. Located right next door, the Orange County Recreation Area at Laroe Road features walking and hiking trails, picnic areas, fishing ponds, and additional green space for all to enjoy. Call today to schedule your private showing. **Home is being sold AS-IS**

335 Laroe Road, Chester

$565,900
2 Beds 3 Baths MDQA2017526 MLS
Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both style and functionality. Step inside to discover a thoughtfully designed interior that boasts hardwood and pine flooring, creating a warm and inviting atmosphere throughout. The combination kitchen and dining area is perfect for entertaining, featuring ample space for gatherings and culinary creations. Natural light floods the home, enhancing the inviting ambiance and highlighting the quality craftsmanship that defines this property. One year old HVAC and four year old hot water heater. The outdoor spaces are equally impressive, with a charming deck and porch that invite you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while taking in the gentle sounds of nature or hosting evening gatherings under the stars. The community pool and recreational facilities provide additional opportunities for leisure and relaxation, ensuring that every day feels like a vacation. Located just blocks from the Chester River, this property offers water-oriented living at its finest. Enjoy easy access to the river, perfect for kayaking or leisurely strolls along the waterfront. The community amenities, including a clubhouse, exercise room, and jogging paths, cater to an active lifestyle, while the meticulously maintained common grounds provide a picturesque backdrop for your daily activities. Parking is a breeze with a detached garage that offers additional storage space, ensuring that your home remains clutter-free. The association fee includes lawn care, snow removal, and trash services, allowing you to spend more time enjoying the luxurious lifestyle this community has to offer. Gibsons Grant is not just a place to live; it's a lifestyle choice that embraces the beauty of nature while providing modern conveniences. With its prime location, high-end features, and a strong sense of community, this townhouse is a rare gem that promises to be a cherished home for years to come. Experience the perfect blend of luxury and comfort in this stunning property, where every detail has been designed with your enjoyment in mind.

115 Gibson Cir, Chester

$700,000
3 Beds 3 Baths MDQA2017542 MLS
Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

$186,900
4 Beds 1 Baths PADE2116642 MLS
Welcome to 37 E. Mowry Street, a spacious 4-bedroom, 1-bath home offering comfort, functionality, and value. Inside, you'll find generous living spaces filled with natural light, providing plenty of room for everyday living, entertaining, or working from home. Step outside to enjoy the backyard—perfect for pets, play, gardening, or simply relaxing outdoors. The property offers a great combination of indoor and outdoor living space, making it an excellent opportunity for both homeowners and investors. Conveniently located near schools, parks, shopping, public transportation, and major commuter routes, this home provides easy access to everything you need. Whether you're looking for your first home or your next investment property, 37 E. Mowry Street is a must-see. Schedule your showing today and discover all the potential this home has to offer!

37 E Mowry St, Chester

$39,999
PADE2116598 MLS
Opportunity awaits at 314 Pennell Street in Chester, PA! This vacant lot offers a prime chance for investors, builders, and developers looking to capitalize on the area's ongoing revitalization. Conveniently located near major roadways, public transportation, schools, parks, and local amenities, this parcel provides easy access to Philadelphia, Wilmington, and surrounding Delaware County communities. Whether you're looking to build a single-family home, add to your investment portfolio, or explore future development possibilities, this lot offers plenty of potential. Public utilities are available in the area, and the property is surrounded by established residential development. Bring your vision and take advantage of this affordable growing market.

314 Pennell St, Chester

$599,900
3 Beds 4 Baths MDQA2017452 MLS
Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home, offering generous counter space, quality cabinetry, and a seamless flow into the dining and living areas. The expansive primary suite provides a private retreat with a walk-in closet and luxurious ensuite bath. Additional bedrooms and flexible living spaces offer plenty of room for guests, a home office, or recreation. Enjoy outdoor living from the private deck, perfect for relaxing and taking in the peaceful surroundings. An attached garage and ample storage add convenience to everyday life. Residents of Bayside enjoy exceptional community amenities, including a clubhouse, fitness center, swimming pool, tennis courts, walking trails, and marina access. The boat slips at Castle Marina are rented. It can be on a short term up to a yearly basis. There are some slips over on the side where Queens landing condos are that can be for sale. Ideally located near waterfront dining, shopping, golf courses, and major commuter routes, this home offers the perfect blend of Eastern Shore charm and modern convenience. Don't miss this opportunity to enjoy a resort-style lifestyle in one of Chester's premier waterfront communities. Additional parking spaces are located across the street for your convenience.

1012 Auckland Way, Chester

$999,900
1003998 MLS
INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.

206 Greycourt Road, Chester

$999,900
1004000 MLS
INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.

206 Greycourt Road, Chester

$425,500
3 Beds 4 Baths MDQA2017442 MLS
Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades. Welcome to Bayside living at its finest. This meticulously maintained home sits in one of Chester's most desirable waterfront communities, offering nearby water access for morning walks along the Chester River, resort-style outdoor pool for summer enjoyment, and professionally maintained grounds. Minutes from Route 50/301 for easy commuting, yet peacefully situated in a serene riverside setting close to shopping, dining, and recreational activities. The owners have transformed this residence with quality upgrades throughout. Real hardwood flooring spans the entire main and upper levels with no carpet anywhere in the home. The entry welcomes you with elegant slate tile while abundant natural light floods every room, creating bright and inviting spaces perfect for both daily living and entertaining. The completely renovated chef-inspired kitchen features top-tier stainless steel appliances including Thermador induction cooktop, GE Monogram wall oven, and Bosch dishwasher. Granite countertops, updated cabinetry, and recessed lighting complete this stunning space. The open-concept design connects seamlessly to the spacious living area, making entertaining effortless and family gatherings comfortable. Your main level living room centers around a cozy gas fireplace surrounded by built-in bookshelves, creating the perfect gathering spot year-round. Step outside to your private deck with retractable awning where you can enjoy winter water views of the Chester River. This outdoor space provides an ideal extension of your living area for morning coffee, evening relaxation, or weekend entertaining. The upper level primary suite serves as your personal retreat with a spacious walk-in closet and luxurious ensuite bathroom featuring a jetted soaking tub and separate shower. Your own private outdoor deck off the primary suite provides a serene escape for morning coffee or quiet evening moments. The second bedroom on this level includes its own attached full bathroom, offering privacy and comfort for family or guests. The versatile top-floor loft space features abundant natural light, two generous walk-in closets, and another full bathroom. Use this flexible area as a guest suite, home office, creative studio, or third bedroom based on your lifestyle needs. The possibilities are endless with this unique third-level retreat. Modern systems ensure comfort and efficiency throughout. The recently updated HVAC system provides year-round climate control while reducing energy costs. High-efficiency washer and dryer convey with the home for added value. The attached one-car garage offers protected parking and additional storage space, while the end-unit positioning provides enhanced privacy with no neighbors on one side. This home is completely turnkey and move-in ready. The combination of hardwood floors, premium Thermador and GE Monogram appliances, modern HVAC system, and updated finishes throughout means you can move in immediately and start enjoying your new lifestyle without any projects or renovations required. Low-maintenance living at its best. Your monthly Condo fee includes lawn maintenance, snow removal, community pool access, and recreation facilities, allowing you to spend your time enjoying the waterfront lifestyle rather than maintaining property. This is the perfect balance of Chester River community living with modern convenience and resort-style amenities. The value proposition is compelling. This home's aggressive positioning combined with over $50,000 in premium upgrades creates an exceptional opportunity for discerning buyers. The motivated seller situation, extensive recent improvements, prime end-unit location

807 Auckland Way, Chester

$330,000
6 Beds 4 Baths PADE2116356 MLS
Welcome to 419 E. 12th Street, a fully renovated home offering the feel of new construction without the new construction price tag. This spacious residence features 6 bedrooms, 3 full bathrooms, and 1 half bathroom, including a private primary suite with its own luxurious en-suite bath. The open-concept floor plan is designed for modern living and showcases hardwood flooring, recessed lighting, and luxury finishes throughout. The beautifully updated kitchen flows seamlessly into the living and dining areas, creating the perfect space for entertaining. With 6 bedrooms, 3 full bathrooms, and 1 half bathroom, this home offers exceptional space and flexibility. The fully finished basement includes additional bedroom accommodations and versatile living space, making it ideal for a large household, guests, a home office, gym, media room, or game room. Every detail has been thoughtfully updated, making this truly a move-in-ready home. Conveniently located just minutes from Widener University, shopping, dining, public transportation, and major commuter routes. Whether you're looking for a spacious primary residence or a potential investment opportunity, this property delivers exceptional space, style, and value. Schedule your private showing today!

419 E 12th St, Chester

$435,000
3 Beds 3 Baths MDQA2017432 MLS
Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout designed for comfortable living, complete with a cozy gas fireplace, generous living spaces, and the convenience of a 1-car garage. Recent improvements include a new roof in 2023 and the front foot fee paid off in 2024, as well as a one-year home warranty for the buyer — adding additional value and peace of mind for the next owner. Life in Bayside is all about lifestyle. Residents enjoy access to resort-style amenities including a clubhouse, outdoor pool, fitness center, tennis courts, volleyball courts, and scenic walking and jogging trails — all just steps from the marina and moments from the Chesapeake Bay. Perfectly located near waterfront restaurants, local shops, and major commuter routes to Annapolis, Baltimore, and Washington D.C., this home offers the ideal blend of relaxation and accessibility. Whether you’re searching for a full-time residence or the perfect weekend waterfront escape, this Bayside condo captures the very best of Eastern Shore living.

106 Bodys Neck Rd, Chester

$559,000
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

$840,000
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

$529,000
3 Beds 3 Baths 898870 MLS
Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.

94 Booth Road, Chester

$700,000
2 Beds 3 Baths MDQA2017364 MLS
Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way offers one of the most desirable locations in the community, with exceptional water views, ground-level access, and an easy walk to the resort-style amenities. Inside, you'll find a gourmet kitchen with quartz countertops, GE Café double wall ovens, upgraded stainless steel appliances, luxury vinyl plank flooring, and an open-concept living space with an electric fireplace and beautiful water views. The primary suite features patio access, a walk-in closet, and a luxurious bath, while the second bedroom suite and private office provide comfort and flexibility. Residents enjoy the Chester House Clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a kayak launch, fishing pier, dog park, tiki bar, and more. Perfectly located on Kent Island, this home offers an exceptional blend of luxury, convenience, and the Chesapeake Bay lifestyle.

132 Wheelhouse Way Unit #11, Chester

$399,000
1002697 MLS
Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching, photography, and enjoying the outdoors. A perfect escape for those seeking privacy, tranquility, and a connection to nature while still being conveniently located within approximately 60 miles of New York City. Located in the heart of Orange County and the Hudson Valley, Chester is one of the region’s most sought-after destinations known for its beautiful countryside, rolling hills, farms, orchards, wineries, breweries, and year-round outdoor recreation. Enjoy close proximity to Goosepond Mountain State Park, Harriman State Park, Sterling Forest, the Heritage Trail, and countless hiking and biking opportunities throughout the area. Orange County offers a unique balance of rural beauty and everyday convenience with nearby shopping, restaurants, golf courses, farmers markets, ski areas, and entertainment. Just minutes from Woodbury Common Premium Outlets, Legoland New York, local equestrian facilities, and major commuter routes including Route 17/I-86, Route 6, and I-87. Convenient access to NJ Transit, Metro-North connections, and park-and-ride locations makes travel to New York City and surrounding areas easily accessible. Whether you are looking for a private nature retreat, recreational land, or a long-term investment opportunity, this property offers a rare chance to own a large parcel in one of the Hudson Valley’s most desirable locations.

492 Black Meadow Road, 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

$90,000
3 Beds 1 Baths PADE2115708 MLS
Welcome to 113 E 13th St, a recently updated 3-bedroom, 1.5-bath home nestled in the heart of Chester, PA. Whether you're an investor seeking a reliable income property or a first-time homebuyer looking for convenience and comfort, this property offers incredible potential. Currently tenant-occupied, the home generates $1,000/month in rental income on a month-to-month lease, providing immediate cash flow or flexibility for your future plans. The home boasts recent updates, blending modern touches with its classic charm. Its prime location offers easy access to major highways, shopping centers, and local amenities, making daily errands and commutes a breeze. Don't miss this opportunity to own a versatile property in a thriving location.

113 E 13th St, Chester

$364,900
3 Beds 3 Baths MDQA2017274 MLS
Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today!

5011 Bridgepointe Dr, Chester

$216,000
3 Beds 2 Baths MDQA2017080 MLS
You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying opportunity. Property is owned by the US Dept. of HUD. All HUD Homes are sold “AS-IS”. This property is HUD Case # 244-032645. Information and Disclosures available at hudhomestore website. property Insurability code is: IE. Bids may only be submitted by HUD Registered Agents/Agencies. Buyers are responsible for Dewints/Rewints coordination/expenses. LBP (Lead-Based Paint) may be present. Seller makes no representations or warranties as to property condition.

108 Price Rd, Chester

$349,900
PADE2115570 MLS
Exceptional redevelopment opportunity in Chester — this 12‑unit apartment building at 1113–1115 Upland St. is currently in shell condition and ready for a full transformation. The structure features solid construction with a stucco‑finished exterior, offering a strong foundation for a complete repositioning. Developers and seasoned investors will appreciate the generous building footprint, flexible layout potential, and blank‑canvas interior that allows for modern systems, finishes, and unit configurations. With consistent rental demand driven by proximity to Widener University, public transportation, major commuter routes, and regional employment centers, this property is well‑positioned for long‑term upside. Ideal for investors seeking a high‑yield value‑add project with significant cash‑flow potential once stabilized.

1113 Upland St, Chester

$620,000
3 Beds 3 Baths MDQA2017258 MLS
Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you’ll find engineered hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of space for gathering and entertaining. The flexible floor plan includes a spacious family room above the two-car garage — perfect for a media room, playroom, home office, or guest retreat. The primary suite offers a relaxing escape with a double vanity, soaking tub, and walk-in shower. Additional highlights include a Rinnai tankless hot water heater, welcoming front porch, and thoughtful upgrades throughout. Enjoy all that Gibsons Grant has to offer, including a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, waterfront access, and scenic open spaces — all conveniently located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer. Coastal living at its best!

265 Evelyne St, 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

$825,000
4 Beds 3 Baths 999741 MLS
Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely find. From the moment you enter, soaring ceilings, natural woodwork, and an open-concept layout create a warm yet sophisticated atmosphere. The heart of the home is the stunning chef’s kitchen featuring granite countertops, a leathered granite kitchen island with storage, breakfast bar, 2 pantry's, and seamless flow into the dining and living spaces; perfect for entertaining or everyday living. A dramatic wood-burning fireplace anchors the living room, while oversized UV tinted windows frame peaceful mountain and wooded views in every direction. The flexible floor plan includes a highly sought-after first-floor bedroom with tray ceilings, spa-like finishes in the bath, whirlpool tub, double vanity, oversized walk-in closets, laundry and balcony. That kind of retreat style feel that makes home hard to leave. Outside, the property truly shines. Enjoy morning coffee on the covered porch, host summer gatherings on the expansive deck and patio, or unwind beneath the pergola surrounded by nature and professionally maintained grounds and gardens. The 10.9-acre setting provides exceptional privacy while still keeping you close to shopping, dining, schools, and commuter access. Additional highlights include central air, smart thermostat, walk-out basement with endless potential, oversized two-car garage, new windows, security system, drilled well, septic, propane heat, and multiple outdoor structures for storage or hobby use. A property like this doesn’t just offer a home, it offers space, serenity, and a lifestyle upgrade. Welcome home to 45 Whitetail Run.

45 Whitetail Run, 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

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