Refine Search
Map
Sort by
$675,000
PADE2119552 MLS
Rarely available stabilized, turnkey drive-up self-storage facility Chester - just 2 minutes from I-95! It totals approximately 8,290 square feet of storage on a 0.43-acre lot (84' x 223') and offers 33 rentable storage units and 3 parking spots, originally built as roughly 50 individual bays. Many of the current units are leased in pairs/groups units that a new owner could separate to lift the unit count and income. The facility offers all drive-up access across a wide, paved center aisle. Most units are established single-story building units, complemented by 5 shipping container units fitted with roll-up storage doors. The unit mix ranges from compact 8'x10' units up to a large 51'x20' (1,020 SF) drive-in unit, giving the property broad appeal to household tenants, contractors, and small businesses. One combined unit has its own separate electric panel and can serve as an on-site office. The property is stabilized at approximately 97% occupancy and is run entirely remotely through cloud-based storage-management software, with all tenants paying online or by ACH and no on-site employees. Demand is driven primarily through online channels, and the operation is gated, fenced, and monitored by 24/7 video recording. The result is a low-overhead, automated business that a first-time storage investor can step into and operate in place. If preferred, the seller is willing to continue managing the site for the buyer. The value-add opportunity is straightforward and low-risk. Current in-place rents are roughly 18% below the facility's own standard rates, and the majority of units have not seen a rate increase in more than a year. A new owner can bring rents to market, grow the tenant-insurance program beyond its current 45% penetration, and apply standard late and admin fees to lift income with minimal capital. The predominantly drive-up construction keeps ongoing maintenance and capital costs low. The location is a core strength. The property sits in an infill Chester neighborhood immediately off I-95, minutes from Widener University, Harrah's Philadelphia Casino & Racetrack, Walmart, and the Penn Terminals port and industrial corridor, and roughly 25 minutes from Center City Philadelphia. This is a dense, established, supply-constrained submarket that supports steady storage demand. Priced at $675,000, the facility offers a going-in cap rate of approximately 8.7% on current income, with upside toward 12% as rents are brought to market - an attractive, income-producing entry point into self-storage ownership. Information contained herein is deemed reliable but is not guaranteed. Buyer to verify all figures. Financials are based on owner-provided data and select operating expenses; a buyer should conduct independent due diligence.

901 E 10th St, Chester
$399,999
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
$250,000
PADE2119544 MLS
Unlock the potential of this prime commercial property, built in 1967 and constructed with durable materials like block, asphalt, and concrete. With a compact lot size of 0.11 acres, this property offers a manageable footprint for savvy investors looking to maximize returns. The strategic location ensures easy access and visibility, making it ideal for a variety of business ventures. Benefit from multiple parking options, including a private garage, parking lot, and driveway, enhancing convenience for clients and employees alike. The property's solid construction promises longevity and minimal maintenance costs, allowing for a focus on profitability. Imagine the possibilities: whether you're looking to lease to reliable tenants or establish your own business, this property is a canvas for your investment dreams. With the right vision, this space can generate consistent cash flow and appreciate in value over time. Don't miss out on this opportunity to secure a valuable asset in a thriving market!

328 Rose St, Chester
$95,000
3 Beds ⋅ 1 Baths ⋅ PADE2119542 MLS
Calling all investors, rehabbers, and savvy buyers! This spacious 3-bedroom, 1-bath brick rowhome presents an outstanding value-add opportunity in Chester. Offering approximately 1,331 square feet of living space, a full basement, and an attached garage, this property is ready for its next transformation. With solid bones and a functional layout, this home is an ideal candidate for a complete renovation. Whether you're looking to fix and flip, renovate and rent, or add to your investment portfolio, the possibilities are endless. Once renovated, this property has the potential to generate strong rental income or attractive resale value. Conveniently located near major highways, public transportation, shopping, schools, and the Philadelphia waterfront, this home offers easy access for commuters and tenants alike. Property is being sold strictly As-Is. Buyer is responsible for any municipal inspections, certifications, and repairs required for settlement. Cash or renovation financing preferred. Bring your vision and unlock the potential this investment opportunity has to offer!

919 Keystone Rd, Chester
$719,900
2 Beds ⋅ 2 Baths ⋅ MDQA2017900 MLS
Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

121 Merlin Dr, Chester
$389,000
3 Beds ⋅ 1 Baths ⋅ 1019170 MLS
Welcome to 185 Oxford Road, Chester! •••••This charming 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral ceiling, natural woodwork, recessed lighting, and a welcoming breakfast bar in the open kitchen. The kitchen is equipped with a cooktop, oven, refrigerator, washer, and dryer (with both electric and gas dryer hookups right in the kitchen). You'll also appreciate the bow window, casement and double-pane windows that fill the home with loads of natural light. •••••The unfinished basement provides plenty of storage, conveniently accessed using Bilco doors. Outside, the level, landscaped lot offers front and backyard space and is partly wooded for privacy. •••••Highlights include: • Brand New Boiler • Brand New Gravel Driveway • Entire House Painted and Refreshed • Central Air plus Ductless Cooling in the Living Room • Propane hot water baseboard heating system • 2 Drilled Wells • Septic system (pumped every 4 years) • 100-amp electric service •••••Located in the highly rated Monroe-Woodbury School District, this home has annual taxes of $6,831 (after STAR discount for primary home-owners). •••••This affordable, single-level Ranch home combines classic appeal with modern improvements and a spacious lot — ideal for comfortable living with room to enjoy the outdoors. •••••Discover the Perfect Blend of Peaceful Country Living and Modern Convenience •••••Escape to this serene rural retreat that offers the best of both worlds: a tranquil, private country setting paired with unmatched accessibility. Nestled in a quiet, picturesque location, this home provides a true sense of peace and privacy while placing everyday essentials and major transportation routes just minutes away. •••••A Paradise for Outdoor Enthusiasts This property is an outdoor lover’s dream. Step outside and immerse yourself in abundant recreational opportunities, with excellent hiking, cycling, and rollerblading right at your doorstep. World-class natural destinations surround you, including Goosepond Mountain State Park, Harriman State Park, and Bear Mountain State Park — all offering miles of scenic trails, stunning lakes, and breathtaking vistas. •••••Just minutes away, the renowned Heritage Trail awaits — a beautifully paved 19.5-mile multi-use path along the historic Erie Railroad corridor, stretching from Middletown to Harriman. Whether you enjoy walking, running, cycling, or rollerblading, this scenic trail delivers peaceful countryside views and year-round enjoyment. •••••Effortless Commuting & Everyday Convenience Commuters will love the easy access to major routes: • Less than 3 miles to Route 17 (The Quickway) • Just 4 miles to the Monroe Park & Ride at Twin Lakes • Approximately 8 miles to the New York State Thruway (I-87) • About 10 miles to the Harriman Metro-North train station •••••Whether heading into the Hudson Valley or New York City, commuting is seamless and efficient. Shopping, dining, top-rated schools, healthcare, and all modern amenities are conveniently close, allowing you to enjoy a relaxed rural lifestyle without ever feeling isolated. •••••This rare combination of peaceful country charm, endless outdoor adventures, and superior location makes this home an exceptional opportunity for those seeking tranquility without compromise. Welcome home to your perfect sanctuary. •••••Reach out for a private showing today and discover all that 185 Oxford Road, Chester has to offer !!

185 Oxford Road, Chester
$725,000
3 Beds ⋅ 3 Baths ⋅ 1024518 MLS
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 9 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

1 Arborvitae Court, Chester
$150,000
4 Beds ⋅ 1 Baths ⋅ PADE2119368 MLS
Discover Your Dream Home on 103 Thurlow Street! *** Introducing, updated in recent years 1103 Thurlow Street in Chester, Pennsylvania. A spacious 4 BD/1.0 BA Row-Home tucked away from busy streets with backyard and modern upgrades. The home features beautiful wood floors throughout entire residence and offers an open concept first floor setting featuring spacious living/dining area, kitchen with tiled backsplash, and stainless-steel appliances. There is an exterior rear door at the end of the hallway leading to a private backyard. There is also one bedroom on main floor for convenience or office use. Upstairs you will find 3 good-sized bedrooms with plenty of closets. Full bathroom with the tub, vanity with mirror and toilet . Full basement would make a great addition for storage or a workspace. Easy access to local shopping and transportation as well as I-95 and Commodore Barry Bridge between PA & NJ. Enjoy the living with easy access to some of the region’s best outdoor areas including the Ridley Creek State Park. Just minutes away from state-of-the-art Subaru Park, an 18,500-seat Major League Soccer stadium, serving as a home to Philadelphia Union. Schedule your private showing today.

103 Thurlow St Unit #306, Chester
$349,999
3 Beds ⋅ 2 Baths ⋅ 974398 MLS
Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with granite countertops, ample cabinetry, and plenty of prep space for entertaining. The renovated bathrooms offer stylish finishes and a fresh, modern feel with all new windows to help keep the indoor temperature steady. The spacious living room is filled with natural light and features a cozy wood-burning fireplace, creating the perfect place to relax year-round. The living room also opens through a brand-new sliding glass door to a private deck—ideal for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. The primary suite offers generous closet space and easy access to an updated full bath, while two additional bedrooms provide flexibility for family, guests, or a home office.

3414 Whispering Hills, Chester
$450,000
PADE2119240 MLS
Welcome to 1023 W. 9th Street plus 1013 W 9th St (Ground)—an exceptional commercial property packed with opportunity and endless potential! Whether you're an investor, entrepreneur, or business owner ready to expand, this versatile space is ready to bring your vision to life. Inside, you'll find a spacious layout featuring a dedicated office on the main level, a second office upstairs, a large bathroom, and ample room to accommodate a variety of business operations. Outside, the fully gated lot provides valuable, secure outdoor space for equipment, vehicles, or additional storage. With its flexible layout, including additional lot space in the back (1013 W 9th St), the possibilities are endless. All building equipment and tools will be removed prior to closing. Don't miss your chance to own this incredible commercial property—Priced to sell fast. Schedule your private showing today before it's gone!

1023 W 9th St, Chester
$25,000
PADE2117950 MLS
Vacant ground

321 W 3rd St, Chester
$350,000
PADE2118336 MLS
Free standing , block building in need of some repair on busy 291.

Chester
$165,000
3 Beds ⋅ 1 Baths ⋅ PADE2119136 MLS
Step into a home that blends modern updates with incredible future potential. 2315 Madison Street welcomes you with a bright, open-concept first floor that feels airy and expansive. Natural light pours across the stylish laminate wood plank flooring, creating a warm atmosphere that flows effortlessly from the living area into the generously sized kitchen. Tucked away for maximum convenience, you’ll also find a dedicated first-floor laundry area that makes daily chores a breeze. Upstairs, the home offers three well-sized bedrooms and a centrally located bathroom, providing a comfortable and functional layout. While currently enjoyed as a spacious single-family residence, this property holds a unique secret: it was originally a duplex and retains its R-2 zoning. This flexibility offers a rare "best of both worlds" scenario for a savvy buyer looking to maintain the current setup or explore the possibilities of the dual-unit zoning down the road. The financial picture is just as bright as the interior. The property is currently generating a steady gross annual income of $17,880, with a tenant on a month-to-month lease as of 9/1/25 paying $1,490 per month. Whether you are looking for a solid performer to add to your portfolio or a versatile property with room to grow, this Madison Street gem is a strategic find in a high-demand area. **Property Summary:** * **Zoning:** Still zoned as a duplex (currently single-family layout) * **Income:** $1,490/mo ($17,880 gross/year) * **Lease:** Month-to-month since 9/1/25 * **Features:** Open concept, laminate wood plank flooring, 1st-floor laundry, 3 bedrooms

2315 Madison St, Chester
$329,000
2 Beds ⋅ 2 Baths ⋅ 1018748 MLS
Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom California-closets style design features floor-to-ceiling shelves and cabinetry. Bedroom #2 also has custom closets. The outdoor patio with privacy fence overlooks the green area. Laundry area with storage shelves and full sized washer and dryer included. Central air conditioning and forced air heating. Natural gas and municipal water and sewer services. This home is in a fantastic location within Whispering Hills - tucked in the rear side of the community alongside the green area near the tennis courts, clubhouse, pool area, playground and dog run. Included with monthly HOA fee: Water, garbage and recycling, snow removal, landscaping, pool pass to two separate pool areas, use of tennis courts, basketball court, playground and clubhouse. Low taxes!!! Excellent commuter location. Bus stop to NYC/NJ in the complex. Close to the highway, supermarket, and shopping. Minutes from Woodbury Common, LegoLand NY, Garnet Health Medical Center, Chester Mall Shopping Center.

4118 Whispering Hills Drive, Chester
$575,000
3 Beds ⋅ 3 Baths ⋅ 1018371 MLS
Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers flexible space for a family room, home office, gym, or guest retreat. Thoughtful upgrades, including a Nest thermostat, Ring security camera with window sensors, and a reverse osmosis water filtration system, enhance both comfort and convenience. In addition to the home's primary boiler heating system, the central HVAC system provides air conditioning and electric auxiliary heat, offering added comfort and flexibility throughout the seasons. Step outside to your own private backyard oasis featuring a spacious deck, above-ground pool, and newly installed white vinyl privacy fence—perfect for relaxing or entertaining. Conveniently located just 12 minutes from Woodbury Common Premium Outlets with easy access to major highways, this home offers the perfect blend of peaceful suburban living and everyday convenience. Don't miss the opportunity to make it yours!

11 Chandler Drive, Chester
$525,000
2 Beds ⋅ 3 Baths ⋅ MDQA2017860 MLS
Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

230 Switchgrass Way Unit #12, Chester
$274,900
3 Beds ⋅ 2 Baths ⋅ PADE2119040 MLS
OPEN HOUSE THURSDAY AND FRIDAY FROM 6PM TO 7PM & SATURDAY 11AM-12PM. Welcome to 725 Irvington Pl, where classic stone charm meets modern updates. This beautifully renovated home is truly move-in ready and has been thoughtfully updated from top to bottom. Step inside to discover brand-new luxury vinyl plank flooring throughout the first floor, fresh paint throughout, and a completely remodeled kitchen featuring new cabinets, countertops, and fixtures. The updated bathrooms offer a clean, modern feel, while the second floor boasts all-new carpeting for added comfort. Major improvements completed in 2026 provide peace of mind, including all new windows, a brand-New HVAC system with Central Air, new hot water heater, updated plumbing and electrical and a new garage door. The main level offers a bright, inviting living room, dedicated dining area, and an efficient layout perfect for everyday living and entertaining. Upstairs you'll find spacious bedrooms and an updated full bathroom. The unfinished basement has been freshly painted, providing a clean, dry space ideal for storage, a workshop, home gym, or future finishing. Outside, enjoy the convenience of a garage and private rear parking. Ideally located, this home offers easy access to I-95, Route 476, and Philadelphia, making commuting a breeze. You'll also be just minutes from shopping, restaurants, grocery stores, parks, schools, and public transportation, providing both convenience and a great neighborhood setting. This is an excellent opportunity to own a beautifully updated, move-in ready home where all that's left to do is unpack and enjoy.

725 Irvington Pl, Chester
$535,000
5 Beds ⋅ 3 Baths ⋅ MDQA2017856 MLS
Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester
$629,900
3 Beds ⋅ 2 Baths ⋅ MDQA2017854 MLS
This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester
$135,000
3 Beds ⋅ 1 Baths ⋅ PADE2118902 MLS
Welcome to 1125 Remington Street, a well-maintained 3-bedroom, 1-bath twin home offering an excellent opportunity for first-time buyers or investors. Priced at just $135,000, this move-in-ready home features fresh paint throughout, an updated kitchen with modern finishes, and a brand-new water heater, providing comfort and value from day one. The main level offers a bright living space, functional layout, and an updated kitchen perfect for everyday living. Upstairs, you'll find three comfortable bedrooms and a full bath. Conveniently located just minutes from Memorial Park, residents can enjoy walking trails, playgrounds, sports fields, and open green space. Commuters will appreciate easy access to Interstate 95, making travel throughout the region a breeze. The home is also approximately 15 minutes from Philadelphia International Airport and about 20 minutes from Philadelphia, offering convenient access to employment, dining, entertainment, and major transportation hubs. Whether you're looking to add to your investment portfolio or purchase an affordable place to call home, 1125 Remington Street is one you won't want to miss!

1125 Remington St, Chester
$850,000
5 Beds ⋅ 3 Baths ⋅ 1020076 MLS
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

5 Hilltop Lane, Chester
$130,000
3 Beds ⋅ 1 Baths ⋅ PADE2118890 MLS
Investors, here is an income-producing rental that checks all the boxes. This 3-bedroom, 1-bath end-of-row home is currently occupied by a long-term tenant of over six years who pays all utilities and has expressed interest in staying, offering the opportunity to acquire a stabilized investment with immediate income. Whether you're adding to your existing portfolio or purchasing your first investment property, this is an excellent opportunity you shouldn't miss. Offered at $130,000 with seller concessions available for qualified buyers. Contact the listing agent for details.

1028 Mcdowell Ave, Chester
$749,900
4 Beds ⋅ 3 Baths ⋅ MDQA2017836 MLS
Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel appliances, a large center island, and plenty of space to gather with family and friends. The cozy gas fireplace adds warmth and charm to the main living area, while the screened patio is the perfect spot to relax with your morning coffee or unwind at the end of the day.The large primary suite offers a peaceful retreat with a spacious walk-in closet, double vanities, and a walk-in shower. Additional bedrooms AND an office provide plenty of room for guests, hobbies, or just about anything you can think of and the convenient mud room adds extra functionality.Living in Four Seasons at Kent Island means enjoying an incredible lifestyle. Residents have access to a stunning 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and a full-time lifestyle director who keeps the social calendar full of activities including walking clubs, yoga, mahjong, kayaking, pickleball, and more.Kent Island living is all about making new friends, staying active, and enjoying the lifestyle you've worked hard to achieve. Come see why so many people are proud to call Four Seasons home. And if that wasn't enough of a reason to check this out.....the seller will pay the $4000 capital contribution fee with a full price offer!!

233 Peregrine Dr, Chester
$750,000
5 Beds ⋅ 3 Baths ⋅ 1020128 MLS
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

3 Hemlock Court, Chester
$147,500
2 Beds ⋅ 1 Baths ⋅ PADE2118874 MLS
acked with potential, this 2-bedroom, 1-bath home is ready for your vision! Featuring beautiful hardwood floors and a timeless brick exterior, this property offers the perfect foundation for your next renovation or investment. With solid character and plenty of charm, the canvas is ready for you to bring your ideas to life. Whether you're looking to create your dream home or add value to your portfolio, this property is full of opportunity. Don't miss your chance to transform this hidden gem into something truly special schedule your showing today! Successful buyer to use Alpert Abstract for closing.

2611 Lindsay St, Chester
$380,000
3 Beds ⋅ 2 Baths ⋅ MDQA2017824 MLS
Welcome to this beautifully situated two-story townhome overlooking the tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient location to Route 50 and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and more. Experience the perfect blend of comfort, convenience, and the relaxed Eastern Shore lifestyle. Designed for easy everyday living, the bright, open floor plan seamlessly connects the kitchen, dining area, and living room, where a cozy gas fireplace creates a warm and relaxing space. The adjoining spacious sunroom showcases tranquil pond views, providing the perfect backdrop for morning coffee, quiet evenings, or entertaining guests. The main level also features a desirable first-floor primary suite with a walk-in closet, private access to the sunroom, and an en-suite bath complete with a relaxing Jacuzzi tub and separate walk-in shower. A flexible bonus room with a laundry area and French door access offers endless possibilities as a home office, den, additional bedroom, craft room, or fitness space. Upstairs, two generously sized bedrooms and a full bath provide comfortable accommodations for family and visitors. As an added bonus, a brand-new roof is currently being installed by the HOA, offering peace of mind and added value for the new owner. Whether you're looking for a full-time residence, a weekend getaway, or a low-maintenance retreat, this exceptional pond front home offers the very best of Kent Island living. Don't miss this rare opportunity—it's more than a home, it's a lifestyle!

6010 Bridgepointe Dr, Chester
$2,840,000
3 Beds ⋅ 2 Baths ⋅ MDQA2017820 MLS
Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester
$490,000
2 Beds ⋅ 3 Baths ⋅ MDQA2017786 MLS
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit #23, Chester
$800,000
4 Beds ⋅ 4 Baths ⋅ 1020165 MLS
Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home. Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday living and entertaining. Sunlight pours into the beautiful sunroom, offering the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the tranquil views of the property throughout every season. Step outside and discover the true highlight of this remarkable property. Designed with entertaining in mind, the backyard is a private oasis featuring a sparkling inground pool, beautifully integrated outdoor living spaces, a custom built fire pit, and built in seating that invites family and friends to gather long after the sun goes down. Whether you're hosting summer pool parties, enjoying crisp fall evenings by the fire, or simply relaxing in your own backyard retreat, this outdoor space delivers an exceptional lifestyle year round. Set on over three private acres, the property offers the perfect balance of open space and privacy. There is plenty of room to explore, play, garden, or simply enjoy the serenity of nature, all while being just minutes from the conveniences of the Hudson Valley. Offering 4 bedrooms, inviting living spaces, and an outdoor setting that feels like your own private resort, this is more than just a home. It is a place where memories are made, weekends are enjoyed, and every season brings something special.

985 Craigville Road, Chester
$295,000
2 Beds ⋅ 2 Baths ⋅ 1019548 MLS
Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and start living, come and take a look today! The Condo charges $475 , HOA $250

2119 Whispering Hills, Chester
board logo

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.