Refine Search
Sort by
2107 Whispering Hills, Chester
$299,000
2 Beds ⋅ 2 Baths ⋅ 1050213 MLS
Welcome to 2107 Whispering Hills, a comfortable 2-bedroom, 1-bath condo offering 1,086 square feet of living space in a convenient Chester location. This home offers an easy, low-maintenance lifestyle with a practical layout and plenty of opportunity to make the space your own. Residents can enjoy community amenities including a swimming pool, providing a great place to relax and enjoy the warmer months without the maintenance of owning a private pool. The condo setting also offers the convenience of having exterior and community maintenance handled for you, allowing more time to simply enjoy your home and surroundings. Whether you're a first-time buyer, downsizing, looking for a weekend getaway, or seeking a low-maintenance home in the Hudson Valley, 2107 Whispering Hills is worth a look. Conveniently located near shopping, dining, parks, and transportation, this home offers a great combination of comfort, convenience, and community living.

2107 Whispering Hills, Chester

510 Auckland Way, Chester
$410,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018734 MLS
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

94 Booth Road, Chester
$485,000
3 Beds ⋅ 3 Baths ⋅ 1050173 MLS
If you're looking for privacy, outdoor recreation, and a home surrounded by a beautiful natural setting, welcome to 94 Booth Road! Situated on 1.8 acres on a quiet cul-de-sac, this property offers the space, peaceful surroundings, and opportunity to make a home your own. Head upstairs to the main living level, where hardwood floors flow throughout the living room and hallway. Andersen windows throughout the home bring in plenty of natural light, while the kitchen features stainless steel appliances and a functional layout that opens to the dining area. Just beyond, French doors lead to one of the home's most inviting spaces: a window-lined three-season sunroom with a propane fireplace. Whether enjoying your morning coffee, reading a book, or relaxing on a crisp fall afternoon, this is a space you'll love spending time in. The main level also features a primary bedroom with an ensuite full bath, two additional bedrooms, and a second full bathroom. Downstairs, you'll find a comfortable family room with a wood-burning fireplace, half bath, laundry room, and access to the two-car garage. A whole-house UV water filtration system and water softener add to the home's practical features. Outside is where this property becomes even more special. The property offers plenty of room to enjoy the outdoors, and with some clearing and maintenance, a trail at the back of the property provides access to a small pond. At the end of the cul-de-sac, you'll also find trail access to Goosepond Mountain State Park, offering 1,558 acres of protected land to explore. Schedule your showing today!

94 Booth Road, Chester

512 Auckland Way, Chester
$375,000
3 Beds ⋅ 4 Baths ⋅ MDQA2018750 MLS ⋅ Bayside BLDG.
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

417 E 20th St, Chester
$75,000
3 Beds ⋅ 1 Baths ⋅ PADE2124206 MLS
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

105 E 22nd St, Chester
$120,000
3 Beds ⋅ 1 Baths ⋅ PADE2124202 MLS
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

339 Taylor Ter, Chester
$75,000
3 Beds ⋅ 1 Baths ⋅ PADE2124140 MLS
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

1116 Parker St, Chester
$75,000
3 Beds ⋅ 1 Baths ⋅ PADE2124048 MLS
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

53 Queen Caroline Ct, Chester
$329,000
2 Beds ⋅ 3 Baths ⋅ MDQA2018730 MLS
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

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

18 Schueler Road, Chester

940 Highland Ave, Chester
$75,000
4 Beds ⋅ 1 Baths ⋅ PADE2123880 MLS
ONLINE AUCTION - Bankruptcy Ordered Auction. This property is being sold with 2 other separate properties in Chester, PA - 1026 Kerlin Street & 1105 Madison St Chester, PA all being sold together as one package in an online auction. This property includes 4 bedrooms and 1 bath and located in the Highland neighborhood. 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.

940 Highland Ave, Chester

1105 Madison St, Chester
$75,000
3 Beds ⋅ 1 Baths ⋅ PADE2123860 MLS
ONLINE AUCTION - Bankruptcy Ordered Auction. This property is being sold with 2 other properties in Chester, PA - 940 Highland Ave & 1026 Kerlin Street, Chester, PA. All being sold together as a package in an online auction. 1105 Madison St is a 3 bedroom, 1 bath 2 story twin home in Delaware County, Chester, PA. 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.

1105 Madison St, Chester

1026 Kerlin St, Chester
$75,000
3 Beds ⋅ 1 Baths ⋅ PADE2123822 MLS
ONLINE AUCTION - Bankruptcy Ordered Auction. Package Sale! This property is being sold with 2 other properties in Chester, PA - 940 Highland Ave & 1105 Madison St, Chester, PA. All being sold as one package deal. This property includes 3 bedroom, 1 bath 2 story rowhome in Edgemont Park neighborhood. Property sells 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.

1026 Kerlin St, Chester

19 Meadow Avenue, Chester
$499,999
2 Beds ⋅ 2 Baths ⋅ 1050131 MLS
Welcome to Chester, NY!! Come see this spacious home featuring 2 bedrooms and 2 full baths, with a bonus room. This home has plenty of possibilities and includes a finished basement and finished attic for all your storage needs. Large 2-car garage for all the gadgets. This home has a large open concept for entertaining family and friends. Additional energy saving feature of solar panels and an oversized deck with an above-ground pool for outdoor enjoyment for all. The home boasts charm and beautiful hardwood flooring throughout many areas of the home. This home is conveniently located near shopping, fine dining, and many leisure activities for all age groups. Easy commute to the city and major transportation hubs for commuters. Local highway and interstate access within minutes. This is a property you want to see; come see what Meadow Av has to offer. Welcome Home!!!

19 Meadow Avenue, Chester

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

8 Townsend Place, Chester

2024 Edgmont Ave, Chester
$79,900
PADE2123436 MLS
Investment opportunity in Chester! This triplex features two 2-bedroom units and one 1-bedroom unit, offering a versatile setup with strong income-producing potential. Whether you're looking to expand your rental portfolio or take on your next investment project, this multi-unit property presents plenty of possibilities. Conveniently located near local shopping, transportation, and major roadways. Schedule your showing today and explore the potential this triplex has to offer! Please note : Property is being sold as-is. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification, research and inspections and are relying solely on the results thereof. Buyer to pay all closing costs and transfer tax.

2024 Edgmont Ave, Chester

2024 Edgmont Ave, Chester
$79,900
5 Beds ⋅ 3 Baths ⋅ PADE2123422 MLS
Discover a prime investment opportunity with this traditional twin/semi-detached home, built in 1920 and offering 1,744 sq. ft. of potential. With 5 spacious bedrooms and 3 full bathrooms, this property is well-suited for rental income or a flip project. The full basement provides additional storage or potential for conversion into livable space, enhancing overall value. Situated on a compact 0.05-acre lot, this property requires minimal maintenance while maximizing rental yield. The brick construction ensures durability and low upkeep costs. On-street parking adds convenience for tenants, while the absence of a homeowners association means no additional fees. With the local market showing steady growth, this property presents an excellent opportunity for cash flow and appreciation. Whether you're a seasoned investor or looking to expand your portfolio, this home is a solid choice for generating returns. Don't miss out on this chance to capitalize on a promising asset! Please note : Property is being sold as-is. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification, research and inspections and are relying solely on the results thereof. Buyer to pay all closing costs and transfer tax.

2024 Edgmont Ave, Chester

412 E 20th St, Chester
$230,000
5 Beds ⋅ 2 Baths ⋅ PADE2121792 MLS
Spacious 5-bedroom, 2-bath Colonial twin offering approximately 1,895 square feet of living space in a convenient Chester location. The main level features an inviting front porch entry, a large living room, dining room, eat-in kitchen, a full bathroom, and a versatile additional room that can serve as a fifth bedroom, home office, or bonus room. Upstairs, you'll find four additional bedrooms and another full bathroom, providing plenty of space for comfortable living. The full unfinished walk-out basement offers abundant storage and excellent potential for future finishing. Additional features include a rear yard and brick fireplace. Conveniently located near schools, shopping, recreation, public transportation, and major roadways. A great opportunity for a homeowner or investor looking to add value and create a home tailored to their vision. Bring your ideas and make this spacious property your own!

412 E 20th St, Chester

14519 Sonnenburg Dr, Chester
$344,000
3 Beds ⋅ 2 Baths ⋅ VACF2001632 MLS
Nestled in the quiet Mistwood Forest neighborhood, this charming home offers comfort, space, and convenience. The main level features a large primary bedroom with a private bathroom, beautiful hardwood floors, a spacious laundry room, and an open-concept kitchen and dining area—perfect for everyday living and entertaining. The home also offers generously sized bedrooms, two-zone heating and cooling, multiple attics, and abundant storage throughout. Enjoy your morning coffee surrounded by natural light in the inviting Florida room or relax on the large rear deck overlooking the expansive, fully fenced backyard. Conveniently located just minutes from shopping, dining, and everything Chester has to offer, this wonderful home is ready for its next owner. Don’t miss your opportunity to make it yours! Some pictures have been virtually staged.

14519 Sonnenburg Dr, Chester

1005 Whispering Hills, Chester
$290,000
2 Beds ⋅ 2 Baths ⋅ 1043197 MLS
Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors. Additional updates include a newer furnace, central air conditioning and water heater! Enjoy country club-style living with fantastic community amenities including clubhouses, swimming pools, tennis courts, basketball courts, playgrounds, walking areas and a dog run. An excellent commuter location with NYC bus service right in the complex, plus convenient access to major highways, shopping, restaurants and everyday necessities. Comfort, convenience and community amenities all in one—this is one you won’t want to miss!

1005 Whispering Hills, Chester

43 Queen Neva Ct, Chester
$445,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018494 MLS
Welcome to 43-A Queen Neva Court, a pristine 3-bedroom, 2.5-bath contemporary condo in the sought-after Queens Landing community. Offering more than 2,000 square feet of living space, the largest model in the community, this spacious end unit features an open, sunlit floor plan that is perfect for everyday living and entertaining. The oversized kitchen provides abundant workspace and storage, while the inviting living area is highlighted by a cozy fireplace. The generous primary suite includes a private bath with a soaking tub and separate shower. Step outside to your patio and enjoy peaceful pond views, added privacy, and the benefits of end-unit living. Queens Landing offers an amenity-rich lifestyle with a community pool, clubhouse, fitness center, tennis courts, and much more. This one is truly a 10/10!

43 Queen Neva Ct, Chester

1819 W 6th St, Chester
$199,900
3 Beds ⋅ 2 Baths ⋅ PADE2122452 MLS
Welcome to 1819 W 6th St, where modern updates, comfortable living and a surprisingly spacious backyard come together in a home that’s ready for its next chapter.This 3-bedroom, 1.5-bath home offers a fresh, modern feel with an easy-flowing layout designed for the way you actually live. The main level features stylish flooring, updated finishes and the convenience of a half bath on the first floor—a feature you’ll appreciate when entertaining guests.Step outside and you’ll find one of the home’s biggest highlights: a large, private fenced backyard with a generous concrete patio, giving you plenty of room to create the outdoor setup you’ve been saving to your inspiration board. Think weekend cookouts, a fire pit, outdoor dining, pets at play or simply your own space to unwind after work.Upstairs, three bedrooms provide flexibility for sleeping, working from home, a creative space or a guest room, along with the full bathroom. And the location makes everyday life even easier. You’re close to the soccer stadium and conveniently positioned for a short ride into Philadelphia, giving you access to the city without giving up the extra outdoor space and quieter residential setting you’ve been looking for.Whether you’re buying your first home, ready for more space or simply tired of paying for someone else’s property, 1819 W 6th St deserves a look in person.Modern feel. Three bedrooms. 1.5 baths. A big backyard. Easy access to Philly. The only thing missing is your key.

1819 W 6th St, Chester

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.

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.