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2108 Providence Ave, Chester
$319,000
7 Beds ⋅ 3 Baths
Welcome to 2108 Providence Avenue, a grand stone residence filled with timeless character, impressive space, and architectural charm. From the expansive wraparound covered porch to the beautiful original woodwork, hardwood floors, decorative glass details, tall windows, and striking staircase, this home showcases craftsmanship that is difficult to find. The main level offers generous living and dining spaces along with a large eat-in kitchen featuring stainless steel appliances and plenty of room for everyday dining and gathering. Adding to the home's functionality is the convenience of main-floor laundry, eliminating the need to carry laundry between levels. With 7 bedrooms, 2 full baths, 1 half bath, plus a second-floor office, there is exceptional flexibility for bedrooms, work-from-home space, hobbies, or additional living areas. The finished third floor provides even more usable space and possibilities. Outside, enjoy the home's beautiful stone façade, spacious wraparound porch, fenced backyard, and detached garage. A full unfinished basement provides substantial additional storage. The home features oil radiator heat, public water and public sewer. Rich in character and generous in size, 2108 Providence Avenue offers the space, craftsmanship, and flexibility rarely found in today's homes. Bring your vision and make this distinctive property your own. Schedule a showing today!

2108 Providence Ave, Chester

Listing courtesy of Realty ONE Group Focus. Contact:

34 Queen Anne Way Unit A, Chester
$570,000
2 Beds ⋅ 2 Baths
The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

34 Queen Anne Way Unit A, Chester

Listing courtesy of RE/MAX Executive. Contact:

117 Harrier Way, Chester
$790,000
3 Beds ⋅ 2 Baths
Open House 10/17 11-1pm. Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering the convenience of **true one-level living with no steps**, three spacious bedrooms, and one of the largest garage configurations available in the community. Unlike many Killarney models designed with two bedrooms and a loft, this home features three true bedrooms, a dedicated laundry room, and an additional bump-out ideal for a home office or den. The open-concept interior features an Ultra Gourmet Kitchen with quartz countertops, upgraded cabinetry and appliances, double wall ovens, a French-door refrigerator, and a large center island perfect for gathering and entertaining. The spacious primary suite includes an Ultra Luxury Spa Bath with a walk-in shower and dual vanities. Tray ceilings, a fireplace, and custom window treatments add comfort and character throughout the home. The exceptionally spacious garage offers plenty of room for additional storage, a golf cart, or recreational equipment. Situated on a **$55,000 premium homesite**, the property enjoys a spacious backyard with generous separation from the neighboring homes behind it, creating a welcome sense of privacy and openness. An extensive hardscaped patio extends the living space outdoors, providing an inviting setting for dining, entertaining, or simply relaxing. Four Seasons at Kent Island offers resort-style 55+ living along the Chester River, highlighted by a 24,000-square-foot waterfront clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a dog park, fishing pier, transient boat slips, waterfront Tiki Bar, and an active calendar of social events. **With three true bedrooms, no-step living, an exceptionally large garage, a premium homesite, and expansive outdoor living space, this Killarney offers a desirable combination of comfort, functionality, and privacy in one of Kent Island's most sought-after communities.** I removed all references to the fairway and golf course, emphasized the spacious backyard and separation from neighboring homes, and reduced repetitive superlatives while keeping the description compelling for MLS buyers.

117 Harrier Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

117 Wright Rd, Chester
$412,000
3 Beds ⋅ 2 Baths
Nestled up to vast farm land, this exquisite ranch-style home offers a perfect blend of comfort and sophistication.This residence boasts a well-maintained exterior with charming vinyl siding, inviting you into a space that feels both warm and welcoming. Step inside to discover an open floor plan that seamlessly integrates the kitchen and living areas, creating an ideal setting for both relaxation and entertaining. The luxury vinyl plank flooring flows gracefully throughout, providing a stylish yet durable foundation for your daily life. Natural light pours in, accentuating the spaciousness and warmth of the home. The heart of this residence is undoubtedly the modern kitchen, equipped with SS Appliances that cater to your culinary aspirations. Featuring an electric oven/range, a sleek microwave, and a dishwasher, this kitchen is designed for both functionality and elegance. The refrigerator offers ample storage for all your gourmet ingredients, making meal preparation a delight. With 3 bedrooms and 2 full bathrooms, this home provides plenty of space for comfort and privacy. Updated Ceiling Fans and Lights throughout the home ensure a refreshing atmosphere year-round. Brand New Roof and Water Heater Installed 2024. Step outside to enjoy the inviting patio, new fence, perfect for morning coffee or evening gatherings under the stars. The expansive 0.26-acre lot offers plenty of room for outdoor activities, gardening, or simply enjoying the tranquility of your surroundings. Parking is a breeze with an attached garage and additional driveway space for guests. The gravel driveway adds a rustic charm while ensuring easy access. This property is not just a house; it's a lifestyle. Experience the joy of living in a well-appointed home that combines modern conveniences with a cozy atmosphere. Whether you're hosting friends or enjoying a quiet evening, this residence is designed to meet your every need. Embrace the opportunity to make this beautiful home your own and enjoy the exclusive lifestyle it offers. Sale of this Home is Contingent upon Sellers finding their home of choice.

117 Wright Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact:

168 Redstart Dr, Chester
$769,900
2 Beds ⋅ 3 Baths
NEW LISTING in the Premiere 55+ Community of Four Seasons @ Kent Island * Offering This Lovely Taylor Model w 2/3 Bedrooms + 2.5 Baths and 3rd Car Tandem Garage * Gorgeous Light Colored Laminated Wood Flooring * Impressive Island w Bar Overhang/Counter Seating + Added Optional Bank of Cabinets w Bonus Counter Space * Pantry * Gas Cooking * Tile Backsplash * Under Cabinet Lighting. This Turn-Key Taylor Model Offers a Comfortable 2014 sf of Living Space with Large Volume Ceilings and Flowing Ever Popular Kitchen-to-Dining-to-Family Room Floor Plan at the Center of the Home. The Bedrooms are Flanked with the 2nd Bedroom with En Suite Full Bath + Walk-In Closet at the Front of the Home and a Rear Facing Primary Bedroom with Tray Ceiling, Triple Windows + Walk-In Closet and En Suite Full Bath with Substantial His 'n Her Vanities and Easy Walk-In Shower. Off the Foyer there is a Versatile Flex Room Accented with Sliding Barn Doors Which Serves Nicely as a Den/Office/Additional Sleeping Area for the Grandkids and Serviced by the Foyer Powder Room Across the Hall. Around the Corner is a Built-In Coat Drop Station and Separate Laundry Room with New Full-Sized Front-Loading Washer and Dryer. The Garage is Spectacular Offering Coveted Additional Parking for a 3rd Car/Golf Cart OR Use it as Additional Storage/Workshop Area. This Home is Propane Gas Heat, Central A/C, Rinnai Tankless Gas Water Heater and Public Water, Public Sewer. At a Mere 1 Year Old, This Home Feels Brand New and Has Been Lightly Lived In and Lovingly Maintained. It Offers an Immediate Move-In Scenario for the Lucky Buyer. Don't Wait for the Builder and Be in by the Holidays! AGENTS: We Are Agent Friendly and We Split Transfer Taxes and Recordation Fees with the Buyer and Offer a Re-Issue Rate on the Title Insurance + Survey to Pass On. The Community of Four Seasons Offers Unparalleled Amenities to Include a 24,000 sf Club House Situated on the Chester River and is Home to a Community Space Where Vibrant Activities are Available to its Vibrant Neighbors and Provides Resort Style Gym, Yoga, Billard's Room, Library, Ballroom and Indoor Pool w Hot Tub + Infinity Outdoor Pool, Cabana, Lounge Areas, Amphitheatre, Fishing Pier, Dog Park, Pickle Ball, Tennis, Bocce Ball + Tot Lot. Homeowners Get Included Grass Cutting, Fertilization + Pesticide Spraying and Lawn Irrigation as a Part of the $315 Monthly HOA Fee Allowing You to Spend More Time Enjoying and Less Time Maintaining! Located 20 Minutes to Historic Downtown Annapolis and to the Regional Anne Arundel Medical Center with an Outpatient Pavilion in Kent Island. It is 30 minutes to Baltimore/Washington International Airport and there are numerous local airport shuttle services offering door to door service making travel easy and stress free for you and your visiting guests. Kent Island Offers a Variety of Wonderful Restaurants Featuring Local Seafood Cuisine + Numerous Marinas and a Freedom Boat Club Location. Four Seasons @ Kent Island is a Wonderful Year-Round or 2nd Home Location for Those Envisioning a Nautically Inspired Lifestyle Combined with a Beautiful, Maintenance Free Home. 168 Redstart Dr is Waiting For You! Call Helpful Lister for More Info.

168 Redstart Dr, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

231 Dominion Rd, Chester
$599,000
Unique opportunity to own a versatile three-unit property situated on approximately one-half acre in Chester. The property features a main residence with 2 bedrooms, 1 full bathroom, and a full basement, offering comfortable living space for an owner-occupant or tenant. A separate building on the property includes two additional rental units: a ground-level 1-bedroom efficiency apartment and an upper-level unit with 2 bedrooms and 1 full bathroom. This setup provides excellent income-producing potential while maintaining privacy between residences. Conveniently located near shopping, dining, and everyday amenities, this property is ideal for investors or buyers seeking a live-in rental opportunity with multiple income streams.

231 Dominion Rd, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

231 Dominion Rd, Chester
$599,000
5 Beds ⋅ 3 Baths
A rare opportunity to own a property that combines comfortable living with income-producing potential. The primary residence features 2 bedrooms, 1 full bathroom, and a full basement, offering ample storage and living space. Behind the main home is a separate building with two additional rental units. The lower-level unit is a cozy 1-bedroom efficiency apartment, while the upper-level unit offers 2 bedrooms and 1 full bathroom, providing excellent options for rental income or multi-generational living. Situated on approximately one-half acre in Chester, this property offers a convenient location close to shopping, dining, and everyday amenities. Whether you're looking to offset your mortgage with rental income or invest in a versatile property, this unique opportunity is not to be missed.

231 Dominion Rd, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

610 Rivers Bend Cir, Chester
$569,000
5 Beds ⋅ 4 Baths
Beautifully maintained Colonial-style home in River’s Bend on the James, offering quality craftsmanship, generous living spaces, and a beautiful 0.8-acre lot. Custom-built by Emerson with a low-maintenance brick and vinyl exterior, this home welcomes you with a spacious foyer featuring detailed molding and chair rail. The formal dining room is highlighted by crown molding, chair rail, and an elegant chandelier. The spacious kitchen offers solid wood cabinetry, a wall oven, center island, built-in desk, and large eat-in area, opening naturally to the family room with built-in bookcases and a gas fireplace. Enjoy the bright Florida room featuring vaulted ceilings, skylights, ceiling fans, and tile flooring, an ideal space for relaxing or entertaining. The home offers 5 bedrooms, 2 full baths, and 2 half baths, with the versatile fifth bedroom perfect for a home office, game room, exercise room, or guest space. Hardwood flooring, detailed trim work, and both front and rear interior staircases add character throughout. An attached rear-entry 2-car garage provides additional storage, while the level 0.8-acre lot offers a spacious and private backyard with plenty of room to enjoy the outdoors. River’s Bend community amenities include swimming, tennis, and nature trails. Conveniently located near dining, shopping, major employment centers, I-95, I-295, Route 288, and Route 150. Some images in this listing have been virtually staged.

610 Rivers Bend Cir, Chester

Listing courtesy of Move4Free Realty, LLC. Contact:

129 Wheelhouse Way Unit 11, Chester
$585,000
2 Beds ⋅ 3 Baths
Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away from the community clubhouse and only steps from the outdoor and indoor pools. One of the most unique advantages of this first-floor residence is its size. Unlike the second, third, and fourth-floor Magothy models, first-floor units offer approximately 100 additional square feet of living space, creating a more spacious and comfortable layout. Combined with more than $30,000 in post-purchase upgrades, this condo stands apart from the moment you walk through the door. By far the most impressive feature, however, is the extraordinary access to the waterfront. Step through your sliding glass doors and find yourself just moments from the Chester River. The peaceful setting allows you to enjoy water views, wildlife, and gentle river breezes from your private patio while offering one of the most coveted locations within the community. Whether you're taking a morning stroll along the shoreline or relaxing outdoors with a cup of coffee, the river feels like an extension of your backyard. Inside, luxury vinyl plank flooring flows throughout the home, complementing the bright, open floor plan filled with natural light from oversized windows and soaring ceilings. The gourmet kitchen is designed for both everyday living and entertaining, featuring a large center island, under-cabinet lighting, abundant cabinetry, and a custom dry bar area. The adjoining dining and living spaces create a seamless gathering area, highlighted by recessed lighting and a cozy electric fireplace. The spacious primary suite serves as a private retreat with dual closets and a beautifully upgraded bath featuring double vanities, custom tile work, a walk-in shower, and dual shower heads. A generous guest bedroom and adjacent full bath provide comfortable accommodations for family and visitors alike. Additional features include a private locked storage room, garage, custom finishes throughout, and a covered patio accented with stacked stone columns—an ideal place to unwind and enjoy the tranquil surroundings. With the clubhouse and pool just steps away, you'll enjoy unmatched convenience while still maintaining a peaceful and private setting. Residents of Four Seasons enjoy an exceptional resort-style lifestyle with a stunning clubhouse, indoor and outdoor pools, tennis and pickleball courts, fitness facilities, walking and biking trails, a community pier, and a full calendar of social activities coordinated by the community lifestyle director. Conveniently located near waterfront dining, marinas, golf courses, Annapolis, Baltimore, Washington, D.C., and BWI Airport, this is Eastern Shore living at its finest. Opportunities to own a first-floor waterfront-proximity unit in this location are exceptionally rare. With extra square footage, extensive upgrades, steps-to-the-pool convenience, and one of the closest locations in the community to the Chester River, this home offers a lifestyle that simply cannot be replicated.

129 Wheelhouse Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

7 Queen Victoria Way Unit B, Chester
$499,000
2 Beds ⋅ 3 Baths
Welcome to 7B Queen Victoria Way at Queen’s Landing, a beautifully renovated waterfront residence w/ spectacular views of the marina basin, marina fairway, and Chester River. The largest residence in Building 7, this spacious 2-bedroom, 2½-bath home with loft offers three levels of living and combines the ease of condominium ownership with the space and feel of a townhome. The extensive renovation creates a fresh, modern, move-in-ready interior featuring an open main level, wide-plank luxury vinyl flooring, refreshed baths, and an updated kitchen with white cabinetry, quartz countertops, stainless-steel appliances, pantry storage, and an eating bar. The waterfront primary bedroom enjoys beautiful views, while the versatile loft is ideal for a home office, guest area, reading retreat, or second sitting room. Step directly from the kitchen onto the gated walk-out waterfront patio and enjoy exceptional water and marina views, outdoor dining, entertaining, or simply watching the boats come and go. Multiple outdoor living areas provide even more opportunities to enjoy the waterfront setting. Queen’s Landing amenities include a waterfront pool and clubhouse, tennis and pickleball courts, fitness and racquetball facilities, scenic walking paths, kayak storage and launch areas, and a full-service marina with slips for sail and power boats. Major renovation, generous living space, outstanding views, and the Queen’s Landing waterfront lifestyle come together at 7B Queen Victoria Way. Offering the best of both worlds---condominium ownership with space, privacy, and multi-level layout of a townhome.

7 Queen Victoria Way Unit B, Chester

Listing courtesy of RE/MAX Allegiance. Contact:

630 Warbler Way Unit 12, Chester
$549,950
2 Beds ⋅ 3 Baths
Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of the most desirable locations in the community, with exceptional water views, ground-level living, and an easy walk to the clubhouse and resort-style amenities. Plus, the home is still under warranty with the builder. Inside, you'll find an open-concept floor plan filled with natural light and beautiful water views. The gourmet kitchen features quartz countertops, upgraded cabinetry, GE Café appliances including double wall ovens, stainless steel appliances, tile backsplash, and plenty of space for entertaining. Luxury vinyl plank flooring flows through the main living areas, and an electric fireplace adds a cozy touch to the living room. The primary suite offers water views, private patio access, a large walk-in closet, and a spacious ensuite bath. A second bedroom suite provides a comfortable space for guests, while the private office offers flexibility for working from home or additional living space. Other upgrades include approximately $8,000 in remote-controlled window treatments, a private walk-out patio, climate-controlled storage, and an attached one-car garage. Step outside and enjoy the convenience of ground-level access and the waterfront lifestyle that makes Four Seasons so special. The 24,000-square-foot Chester House clubhouse is just a short walk away and features indoor and outdoor pools, a fitness center, yoga studio, game rooms, library, gathering spaces, and more. Residents also enjoy pickleball, tennis, bocce, walking and biking trails, a kayak and paddleboard launch, fishing and boat pier, dog park, waterfront beach area, fire pits, tiki bar, and a full calendar of clubs, fitness classes, and social events. Located on Kent Island just minutes from the Bay Bridge, Four Seasons offers easy access to Annapolis, Baltimore, DC, and Maryland's Eastern Shore. Waterfront dining, boating, golf, shopping, and the Chesapeake Bay lifestyle are all close by. Why wait for new construction when you can move right into a nearly new home with upgrades already completed?

630 Warbler Way Unit 12, Chester

Listing courtesy of RE/MAX Executive. Contact:

330 W 15th St, Chester
$190,000
3 Beds ⋅ 1 Baths
Welcome to 330 W 15th St, a beautifully updated home where modern style meets effortless comfort. From the moment you step onto the enclosed front porch—now featuring brand-new windows—you’ll notice the care and attention to detail that defines this property. The main level boasts a seamless open-concept layout, tied together by durable LVP flooring and a warm, neutral color palette that makes the entire space feel bright and inviting. At the heart of the home is the stunning updated kitchen, anchored by a large island and gorgeous quartz countertops. Outfitted with stainless steel appliances and plenty of workspace, it’s a dream for anyone who loves to cook or entertain. Just off the kitchen, a sliding glass door leads directly to the rear deck, perfect for morning coffee or dining under the stars. Upstairs, the soft, neutral tones continue into three well-sized bedrooms, all finished with cozy new carpeting. The primary bedroom is a true retreat, featuring two closets and updated windows that let in plenty of natural light. The hallway bathroom has been refreshed with a newer tub and surround, complemented by modern fixtures, and sits conveniently near a linen closet for extra storage. The lower level adds even more versatility with a partially finished bonus room featuring LVP flooring—ideal for a home office, gym, or hobby space. A separate storage room houses the laundry hookups and provides easy outdoor access. With its fresh updates and stylish finishes, this home is ready for you to move right in and start making memories.

330 W 15th St, Chester

Listing courtesy of Compass Pennsylvania, LLC. Contact:

510 Auckland Way, Chester
$410,000
3 Beds ⋅ 3 Baths
Welcome home to this beautifully updated end-unit townhome in the desirable Bayside community, facing a peaceful row of trees. This spacious three-level home offers an open, inviting layout, beautiful hardwood floors, and numerous recent updates. Enter from the main-level foyer into a spacious bonus room—perfect for a family room, home office, gym, or additional entertaining space. Step directly outside to the back deck, where you can enjoy grilling and entertaining while overlooking the large grassy common area. Upstairs, the open-concept main living level features a spacious living room with a gas fireplace and access to a second deck, a dining area, and an updated kitchen, all complemented by beautiful hardwood flooring. A convenient updated half bath completes this level. The top floor offers three generously sized bedrooms. The primary suite features a beautiful custom accent wall and an updated primary bath, creating a comfortable and stylish retreat. The updated hall bathroom serves the additional bedrooms. Recent major updates include a new HVAC system (2025) and a new hot water heater (2026). Condo replaced roof and skylight (2025) & power-washed exterior (9/2026). All providing added peace of mind for the next owner. Enjoy all that the Bayside community has to offer, including an outdoor pool, hot tub, tennis/pickleball courts, clubhouse with meeting/party room, and exercise room. The location is ideal for an active lifestyle, with a short walk to the Chester River, a local pub, the Cross Island Trail, and a marina. You'll also enjoy easy access to the Bay Bridge, restaurants, shopping, and all that Kent Island and Maryland's Eastern Shore have to offer. Move-in ready, beautifully updated, and perfectly situated—this Bayside townhome is ready to welcome you home!

510 Auckland Way, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

247 Redstart Dr, Chester
$899,990
3 Beds ⋅ 3 Baths
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.

247 Redstart Dr, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

830 Warbler Way Unit 2833, Chester
$689,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. 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.

830 Warbler Way Unit 2833, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

1616 Postal Rd, Chester
$635,000
5 Beds ⋅ 3 Baths
This charming traditional home, offers a perfect blend of comfort and functionality. With 2,818 square feet of thoughtfully designed living space, this residence features five spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover a cozy family room with wood burning fireplace that seamlessly connects to the kitchen, creating an inviting space for gatherings and everyday living. The kitchen boasts a gorgeous quartz island, perfect for casual meals or entertaining guests as well as a tastefully designed formal dining room. As you move upstairs, you'll find four spacious bedrooms and 2 full bathrooms including a primary suite. Enjoy the luxury of a soaking tub in the primary bathroom, providing a serene escape after a long day. The 3rd floor features an oversized bedroom or recreation room. The possibilities are endless, create a home gym, theatre or gaming room or office space. Outside, the property features a side-entry garage with additional storage space, ensuring convenience and organization. The 0.27-acre lot provides a lovely fenced in outdoor area for gardening or simply enjoying the fresh air. This home is not just a place to live; it's a place to create lasting memories. Experience the perfect blend of style, comfort, and functionality in this delightful residence. Multi-use zoning allows your home business dreams to come true. Zoned residential and commercial.

1616 Postal Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

1351 Calvert Rd, Chester
$645,000
6 Beds ⋅ 3 Baths
A rare financing opportunity: qualified buyers may be able to assume the seller’s existing loan at an interest rate of approximately 3%, and VA eligibility is not required. From the welcoming front porch overlooking the bay to the spacious backyard with two storage sheds, this home offers room to live, work and unwind. The kitchen features stainless steel appliances and granite countertops with abundant workspace, making it ideal for everyday living and entertaining. Upstairs, the primary suite feels like a true retreat with a separate sitting area, walk-in closets, dual vanities and an impressive oversized shower. A flexible water-view room on the main level provides the perfect setting for a home office or sixth bedroom. The paved driveway leads to an expansive garage with exceptional storage and workshop space, along with a 30-amp hookup for RV or boat shore power that can also accommodate EV charging. Located on beautiful Kent Island, Marling Farms is an amenity-rich waterfront community offering four beaches, a pavilion, community docks, playground and swing areas, a baseball field and a basketball court.

1351 Calvert Rd, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

512 Auckland Way, Chester
$375,000
3 Beds ⋅ 4 Baths
Nestled in the prestigious Bayside community, this exquisite townhouse that was just updated and renovated in 2026 offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. With renovations completed in 2026, this home boasts modern elegance and thoughtful design throughout its 1,899 square feet. Newer roof, HVAC and hot water heater. Step inside to discover a warm and inviting interior with all new luxury vinyl plank and ceramic tile flooring, featuring a floor plan that seamlessly connects the kitchen and living areas. The family room, conveniently located off the kitchen, is adorned with an electric fireplace, creating a cozy focal point for relaxation. The gourmet kitchen is a chef's dream that includes new quartz countertops, backsplash, new stainless steel appliances, built-in microwave, and a cooktop that promises culinary excellence. Ample storage and a spacious layout make meal preparation a delight. The home features three generously sized bedrooms, each designed with comfort in mind, including an updated primary suite with an luxurious walk-in shower, quartz countertops and new tile flooring. Enjoy the convenience of a fully finished basement with a walkout level, providing additional living space and easy access to the outdoors. The basement also includes garage access, ensuring practicality and ease of living. Step outside to your private deck, where the Chester River is just a short stroll away. The community offers an array of amenities, including a sparkling outdoor pool, tennis courts, and a clubhouse, fostering a vibrant social atmosphere. For those who enjoy an active lifestyle, bike trails and exercise rooms are readily available. Parking is a breeze with an attached garage and additional off-street spaces, ensuring ample room for guests. The meticulously maintained grounds, with included lawn care and snow removal, allow you to enjoy your surroundings without the hassle of upkeep. This property is not just a home; it's a lifestyle. Experience the tranquility of riverfront living while being part of a community that values both leisure and luxury. Embrace the opportunity to make this stunning townhouse your own and indulge in the exclusive lifestyle it offers.

512 Auckland Way, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

228 Bayberry Dr, Chester
$665,000
2 Beds ⋅ 3 Baths
Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENSUITE BATHROOMS plus additional HOME OFFICE/DEN or spare bedroom & POWDER ROOM off foyer. There is a 22X10 BONUS storage space in the upgraded GARAGE LOFT/ “Sky-Basement” The stunning CHEF'S KITCHEN is the heart of this home & opens up to DINING AREA & GREAT ROOM. KITCHEN features upgraded CAFE by GE STAINLESS APPLIANCES, granite countertops, a plethora of custom 42" cabinets, huge CENTER ISLAND & PROFESSIONALLY appointed WALK-IN PANTRY. Dining area off kitchen flows seamlessly into the FAMILY/GREAT ROOM complete w/GAS FIREPLACE for cool fall evenings & SUNDAY-FUN-DAY Football gatherings! Enjoy the ease & luxury of a primary bath w/large CUSTOM WALK-IN SHOWER featuring built-in bench, & double vanities . Spacious walk-in closet (also custom-finished) includes a built-in safe for keeping valuables & important documents. And the crowning touch? PLANTATION SHUTTERS throughout--ABSOLUTELY STUNNING---and UNDENIABLY ELEVATED! An OVERSIZED 2-CAR GARAGE complete w/OPTIONAL 22x10 LOFT STORAGE offers a smart, tucked-away solution for everything you want close at hand-but out of sight. The meticulous exterior features a screened porch, & paver patio w/retractable awning providing additional space for entertaining or simply relaxing & enjoying the outdoors. The beautifully landscaped lot backs to trees and popular CROSS-ISLAND TRAIL as well as views of the scenic community water-features, & even has an invisible fence for your four-legged friend. The "Icing On The Cake" is definitely the ABUNDENT AMENITIES (including lawn-care!) covered by your reasonable monthly HOA dues....Stunning (WATERFRONT!) INDOOR & OUTDOOR SWIMMING POOLS, fitness center, DOG PARK, walking paths, fishing/crabbing pier, PICKLE & BOCCE BALL COURTS & SO MUCH MORE- there's always something to see & enjoy. The community also features a beautiful clubhouse with BALLROOM and various multi-purpose spaces for learning opportunities & social events. Located on the Chester River & Chesapeake Bay, you will be DAZZLED by the natural beauty of the area- -Of YOUR Community.... Literally a vacation without ever leaving town. Local medical facilities, shopping, restaurants & access to the DELMARVA beaches enhance the neighborhood's appeal, making it a wonderful place to call home. Experience the vibrant lifestyle and FRIENSHIPS & MEMORIES to be made in this exceptional community!

228 Bayberry Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

417 E 20th St, Chester
$75,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION - Bankruptcy Ordered Auction. 3 bedrooms and 1 full bathroom rowhome in Chester, PA This property is being sold with 2 other properties in Chester as one auction - including 1116 Parker St, Chester and 339 Taylor Ter, Chester. Properties sell via online auction, and list price reflects opening bid amount. Final sale price will be determined through competitive bidding, and this sale is subject to court approval. Sale is being conducted pursuant to Chapter 11 bankruptcy proceedings pending in the U.S. Bankruptcy Court, Middle District of Florida, Case No. 8:26-bk-01636-CPM, In re: RAD Diversified REIT, Inc., et al. Please contact listing agent for more information regarding the auction terms and conditions.

417 E 20th St, Chester

Listing courtesy of Sanford Alderfer Real Estate. Contact:

15 Qun Ann Way Unit E, Chester
$539,000
2 Beds ⋅ 3 Baths
Located in the beautiful Queens Landing community, this Spanish-style waterfront townhouse offers a luxurious lifestyle with stunning river views. The interior boasts an open floor plan, featuring a combination dining and living area with recessed lighting and a corner gas fireplace. The kitchen is equipped with upgraded countertops and high-end appliances, including a built-in microwave and new additional cabinet and countertop space. Upstairs you will find 2 spacious bedrooms both with private balconies, 2 full bathrooms, and a large loft space above the primary bedroom. Outside you can enjoy your private balcony or relax on the patio, surrounded by beautifully landscaped grounds. The community amenities include an in-ground pool, tennis courts, walking trails, and access to the Chester River. Come tour this waterfront property today!

15 Qun Ann Way Unit E, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

105 E 22nd St, Chester
$120,000
3 Beds ⋅ 1 Baths
Long term tenant! Over 20yrs! Currently rented for $1,150.00. Lease ending 8/31/2026 A solid investment property in the heart of Chester! This classic single-family home boasts durable brick construction, a manageable lot. Making it ideal for low-maintenance ownership. Inside, you’ll find a functional layout with a mix of hardwood and carpeted flooring, ample natural light, and generous ceiling heights that appeal to tenants seeking comfort and space. With public water and sewer, central heating, and wall-unit cooling, the home is equipped with reliable utilities to keep operating costs predictable. The property is situated within the Chester-Upland School District and is located in a convenient area with strong rental demand, making it an excellent candidate for steady cash flow. Whether you’re expanding your rental portfolio or looking for an affordable entry-point investment, 105 E 22nd Street offers the perfect blend of value, durability, and income potential.

105 E 22nd St, Chester

Listing courtesy of Springer Realty Group. Contact:

339 Taylor Ter, Chester
$75,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION - Bankruptcy Ordered Auction. Welcome to 339 Taylor Terrace in Chester! This end-unit rowhome features 3 bedrooms and 1 full bathroom. This property is being sold with 2 other properties in Chester as one auction - including 1116 Parker St, Chester and 417 E 20th St, Chester. Properties sell via online auction, and list price reflects opening bid amount. Final sale price will be determined through competitive bidding, and this sale is subject to court approval. Sale is being conducted pursuant to Chapter 11 bankruptcy proceedings pending in the U.S. Bankruptcy Court, Middle District of Florida, Case No. 8:26-bk-01636-CPM, In re: RAD Diversified REIT, Inc., et al. Please contact listing agent for more information regarding the auction terms and conditions.

339 Taylor Ter, Chester

Listing courtesy of Sanford Alderfer Real Estate. Contact:

1116 Parker St, Chester
$75,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION - Bankruptcy Ordered Auction. Package Sale! Welcome to 1116 Parker St in Chester! This two-story rowhome features 3 bedrooms and 1 full bathroom with approximately 1,316 square feet of living space. This property is being sold with 2 other properties in Chester as one auction - including 339 Taylor Terrace, Chester and 417 E 20th St, Chester. Properties sell via online auction, and list price reflects opening bid amount. Final sale price will be determined through competitive bidding, and this sale is subject to court approval. Sale is being conducted pursuant to Chapter 11 bankruptcy proceedings pending in the U.S. Bankruptcy Court, Middle District of Florida, Case No. 8:26-bk-01636-CPM, In re: RAD Diversified REIT, Inc., et al. Please contact listing agent for more information regarding the auction terms and conditions.

1116 Parker St, Chester

Listing courtesy of Sanford Alderfer Real Estate. Contact:

1012 Auckland Way, Chester
$599,900
3 Beds ⋅ 4 Baths
KENT ISLAND WATERFRONT • GOURMET KITCHEN • TWO PRIVATE DECKS • LUXURIOUS PRIMARY SUITE • CLUBHOUSE + FITNESS CENTER • MARINA ACCESS Experience Kent Island waterfront living in this beautifully appointed townhome in sought-after Bayside of Chester. The open-concept interior offers abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring generous cabinetry, ample counter space, and a large center island with seating that flows seamlessly into the dining and living areas. The spacious primary suite offers a walk-in closet and luxurious ensuite bath, while additional bedrooms and flexible spaces provide room for guests, a home office, or recreation. Enjoy TWO PRIVATE DECKS for outdoor dining, morning coffee, or relaxing in the peaceful surroundings. An attached garage, additional storage, and parking spaces across the street add convenience. Bayside amenities include a clubhouse, fitness center, pool, tennis courts, walking trails, and marina access. Castle Marina slips are available for short-term or annual rental, with select slips near Queens Landing potentially available for purchase. Close to waterfront dining, shopping, golf, and major commuter routes.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact:

231 Evelyne St, Chester
$815,000
4 Beds ⋅ 3 Baths
This beautiful coastal Colonial home in Gibsons Grant offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, the open floor plan invites warmth and connection. Enjoy cooking up your favorite feast in the upgraded kitchen featuring an island, built-in appliances, and endless countertops. The family room, complete with a propane fireplace, is perfect for gatherings and gamed. Step outside to discover beautifully maintained common grounds, a community center, and a inground swimming pool. The neighborhood boasts walking paths, tennis courts, and picnic areas, ideal for outdoor enthusiasts. Located near the Chester River, residents can enjoy serene views and water access. With excellent schools and parks nearby, this community is perfect for those seeking an active lifestyle. Additional conveniences include lawn maintenance, snow removal, and trash services, ensuring a low-maintenance lifestyle. Experience the charm and vibrancy of this welcoming community-your new home awaits!

231 Evelyne St, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

53 Queen Caroline Ct, Chester
$329,000
2 Beds ⋅ 3 Baths
Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boats when available through marina along with Kayaking and storage. With 1,440 square feet of thoughtfully designed living space, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, creating an ideal space for entertaining or quiet evenings at home. The family room, conveniently located off the kitchen, features an electric fireplace, providing a cozy ambiance for gatherings. On the second level, are two bedrooms both with their private full bath. The most recent upgrades include; New HVAC, new electric fireplace, new kitchen appliances (GE Profile), updated bathroom, new shower, new carpeting and painted throughout. The community amenities include access to an outdoor swimming pool, tennis courts, and pickleball courts, all designed for an active and social lifestyle. The clubhouse and fitness center provide additional opportunities for relaxation and recreation. This home is conveniently located off of 301/50 and minutes from the Bay Bridge for an easy commute. to Annapolis/DC or Baltimore. NOTE; Community upgrade for Fios internet in process and a line of new trees is going behind the home this fall for added privacy as per HOA

53 Queen Caroline Ct, Chester

Listing courtesy of EXP Realty, LLC. Contact: