Homes for Sale in Chester-Upland School District, PA: Chester, Chester Township & Upland

The Chester-Upland School District covers three communities along the Delaware River in southeastern Delaware County: the City of Chester, Chester Township, and Upland Borough. This is the county's most historically significant industrial corridor, once home to major shipbuilding and manufacturing operations, and it's currently in the middle of a genuine revitalization push tied to the Chester waterfront, Subaru Park, and Widener University's continued growth.

For buyers, this is the most affordable entry point into Delaware County real estate, full stop. As a Delaware County specialist with a finance and mortgage background, I work with a lot of investors and first-time buyers in this market, and I can walk you through exactly what that affordability trade-off looks like street by street.

Why Buy a Home in Chester-Upland School District, PA?

  • Communities: Chester City, Chester Township, and Upland Borough
  • Commute: I-95 and I-476 both run through the district, and the Chester Transportation Center puts SEPTA Regional Rail within reach for a Center City commute
  • Price range: The most affordable housing stock in Delaware County, generally well under the county median, with genuine opportunity for buyers and investors willing to do some homework on specific blocks
  • Home styles: Rowhomes and twins close to the waterfront and downtown Chester, older single-family homes in Chester Township, and a mix of modest single-family and multi-family housing in Upland
  • Local draw: The Chester waterfront, Subaru Park (home of the Philadelphia Union), Widener University, and easy river and highway access
  • Schools: Chester-Upland runs pre-K through 12, and the district also has a growing charter presence in Chester, including Chester Charter Scholars Academy, which some families choose as an alternative within the district's boundaries

Homes for Sale by Town in Chester-Upland School District

Chester City: the district's population center and the historic heart of Delaware County's industrial waterfront. The most affordable homes in the district, and where most of the active revitalization is concentrated.

Chester Township: a smaller, separate municipality that shares ZIP code 19013 with the City of Chester. Quieter than the city itself, with a similar price point.

Upland Borough: the smallest of the three communities, a tight-knit borough tucked along the river between Chester and the surrounding townships. Page coming soon, use the link above once it's live.

Chester-Upland School District Real Estate Market

I'm going to be straight with you here: this is the slowest-moving, least expensive market in Delaware County, and I'd rather tell you that directly than dress it up. Days on market run longer than the county average, and a lot of the activity is investor-driven rather than owner-occupant driven. That's not a knock on the community, it's just the reality of the numbers right now.

What that means for buyers is real opportunity if you're comfortable with some rehab work or you're building a rental portfolio. What it means for sellers is that pricing and presentation matter even more than usual, since you're competing for a smaller pool of qualified buyers. I do a lot of work with investors and creative financing in exactly this kind of market, so if that's your angle, I can talk through numbers with you.

For the countywide picture (mortgage rates, how fast homes are selling, and where prices are heading), see my Delaware County housing market update. I refresh it every quarter.

Frequently Asked Questions About Chester-Upland School District, PA

Is Chester-Upland a good school district?

Chester-Upland has faced well-documented financial and academic challenges over the years, and I think buyers deserve an honest answer rather than a sales pitch on this one. Some families in the district choose charter options like Chester Charter Scholars Academy. If schools are your top priority, it's worth a direct conversation about what matters most to your family before you commit to this district.

What towns are in Chester-Upland School District?

Three: the City of Chester, Chester Township, and Upland Borough. All three sit along or near the Delaware River in southeastern Delaware County.

How far is Chester-Upland School District from Philadelphia?

About 15 to 20 miles from Center City, with direct access via I-95. Regional Rail service is available from the Chester Transportation Center, with typical trips into the city running 30 to 40 minutes.

What are home prices like in Chester-Upland School District?

This is consistently the most affordable market in Delaware County. Chester City and Chester Township share ZIP code 19013, so most third-party market data blends the two rather than tracking them separately, worth keeping in mind if you're comparing numbers from different sites.

Work With a Delaware County Realtor Who Knows Chester-Upland School District

Whether you're a first-time buyer looking for affordability or an investor looking for the right numbers, I can help you understand exactly what you're getting into in this market. My background in mortgage and finance means I can also help you think through creative financing if that's part of your strategy.

Contact me for a Chester-Upland home search consultation »

Get a free home valuation in Chester-Upland School District »

Licensed Real Estate Agent in Pennsylvania and Delaware | Serving Chester-Upland School District and all of Delaware County

Current Listings in Chester-Upland School District

327 E 20th St, Chester
$220,000
3 Beds ⋅ 2 Baths
Proudly presenting 327 E. 20th Street for sale in Chester, PA! This generously sized Twin house measures in at just under 1,400 square feet with 3 Bedrooms 1.5 bathrooms, 1st Floor laundry, mudroom with closet and more. You enter the home through the front porch to the living room with open floor-plan and updated hardwood flooring throughout the first floor. The updated kitchen features electric cooking, granite countertop and soft close drawers and cabinets! Past the kitchen is a modest sized mudroom that has a tall closet, powder room/laundry room and access to the rear yard. The second floor features 3 bedrooms and 1 full bathroom. The rear and middle bedrooms have modest sized closets and the front bedroom has a large closet that is the width of the bedroom. The full unfinished basement has been waterproofed, walls have been dry-locked and the floor has been Epoxied. The basement is a great place for storage or personal use, it can be converted into usable space easily. Located close to I-95, Delaware State, Philly International Airport and NJ makes it easy for you to get wherever you need to go quickly. First time home buyers can take advantage of a variety of first time home-buyer programs to access closing cost assistance; we can work with them all! Schedule a showing today and come and see the convenience that this home has to offer!

327 E 20th St, Chester

Listing courtesy of United Real Estate. Contact:

6 Church St, Brookhaven
$145,000
4 Beds ⋅ 1 Baths
Welcome to 6 Church St, a fantastic opportunity for investors, contractors, and experienced flippers looking to transform a property and build equity. This 4-bedroom, 3-story brick home has been completely gutted and cleaned out to the framing, providing a blank canvas for a full renovation and the opportunity to customize the layout to fit today's market .The property offers a solid brick exterior, a spacious footprint, a full basement with ample storage potential, a private backyard, and a driveway with parking for two vehicles. With its generous space and flexible layout, this property presents exciting possibilities for a profitable flip, long-term rental, or future residence. Conveniently located in Brookhaven, the home offers easy access to local shopping, restaurants, parks, and major roadways. Renovated homes on the same street reportedly sell in the $272,000–$289,000 range, making this an opportunity worth exploring for buyers ready to take on a full renovation. Property is being sold strictly AS-IS. Buyer is responsible for the Borough Use & Occupancy (U&O) inspection. Bring your vision, creativity, and contractor expertise to unlock this property's potential!

6 Church St, Brookhaven

Listing courtesy of BHHS Fox & Roach-Haverford. Contact:

2100 W 6th St, Chester
$225,000
A unique Chester property offering flexibility, outdoor space, and seller financing options! Offered at $225,000, this two-story corner property features approximately 2,276 sq. ft. of building space on a 1,360 sq. ft. lot. SELLER FINANCING AVAILABLE Seller will consider financing with 20% down ($45,000) and financing of the remaining $180,000 for a qualified buyer. Interest rate below current bank financing may be available. Strong proof of income required. Terms negotiable, subject to seller approval. PROPERTY HIGHLIGHTS Two-story corner property Approximately 2,276 sq. ft. of building space Existing 2-bedroom, 1-bath apartment on the second floor Flexible first-floor layout Fenced backyard Private side deck Well-maintained interior SECOND FLOOR — 2-BEDROOM APARTMENT 2 bedrooms and 1 full bathroom Kitchen and living space In-unit washer and dryer Like-new appliances Private side deck FIRST FLOOR — FLEXIBLE SPACE Brand-new flooring Kitchen and bathroom Large open layout with potential for a variety of uses, subject to zoning verification and required approvals OUTDOOR SPACE Large fenced-in backyard Additional outdoor space offered by the corner-lot layout ZONING & USE — BUYER DUE DILIGENCE REQUIRED Buyer is responsible for independently verifying zoning and permitted uses with the City of Chester, including residential and commercial use, occupancy requirements, permits, rental requirements, business licensing, code compliance, and any required variances or approvals. Seller makes no representation or guarantee regarding any specific use, unit count, mixed-use configuration, or redevelopment potential. Property is offered AS-IS. Buyer should complete all due diligence before purchase.

2100 W 6th St, Chester

Listing courtesy of Real of Pennsylvania. Contact:

2100 W 6th St, Chester
$225,000
2 Beds ⋅ 1 Baths
A unique Chester property offering flexibility, outdoor space, and seller financing options! Offered at $225,000, this two-story corner property features approximately 2,276 sq. ft. of building space on a 1,360 sq. ft. lot. SELLER FINANCING AVAILABLE Seller will consider financing with 20% down ($45,000) and financing of the remaining $180,000 for a qualified buyer. Interest rate below current bank financing may be available. Strong proof of income required. Terms negotiable, subject to seller approval. PROPERTY HIGHLIGHTS Two-story corner property Approximately 2,276 sq. ft. of building space Existing 2-bedroom, 1-bath apartment on the second floor Flexible first-floor layout Fenced backyard Private side deck Well-maintained interior SECOND FLOOR — 2-BEDROOM APARTMENT 2 bedrooms and 1 full bathroom Kitchen and living space In-unit washer and dryer Like-new appliances Private side deck FIRST FLOOR — FLEXIBLE SPACE Brand-new flooring Kitchen and bathroom Large open layout with potential for a variety of uses, subject to zoning verification and required approvals OUTDOOR SPACE Large fenced-in backyard Additional outdoor space offered by the corner-lot layout ZONING & USE — BUYER DUE DILIGENCE REQUIRED Buyer is responsible for independently verifying zoning and permitted uses with the City of Chester, including residential and commercial use, occupancy requirements, permits, rental requirements, business licensing, code compliance, and any required variances or approvals. Seller makes no representation or guarantee regarding any specific use, unit count, mixed-use configuration, or redevelopment potential. Property is offered AS-IS. Buyer should complete all due diligence before purchase.

2100 W 6th St, Chester

Listing courtesy of Real of Pennsylvania. Contact:

619 W 5th St, Chester
$165,000
4 Beds ⋅ 2 Baths
Welcome to this 4-bedroom, 1.5-bath Chester, PA home offering an excellent opportunity for a new owner or investor looking to expand their real estate portfolio. With four bedrooms, functional living space, and plenty of potential, this property is ready for its next chapter. VA LOAN OPPORTUNITY: The seller has an assumable VA loan, offering a potential opportunity for a qualified buyer to assume the existing loan and payments, subject to lender/servicer approval and applicable VA requirements. Whether you're looking for a place to call home or your next investment property, this Chester opportunity is worth a closer look. Schedule your private showing today and see the possibilities for yourself!

619 W 5th St, Chester

Listing courtesy of EXP Realty, LLC. Contact:

1016 Remington St, Chester
$154,900
3 Beds ⋅ 1 Baths
Welcome home to this charming 3-bedroom, 1-bath interior row home in the City of Chester! A welcoming front porch sets the tone, giving you the perfect spot for morning coffee or relaxing evenings outside. Inside, the home offers a comfortable, functional layout with a living area, dining space, and kitchen on the main level. Upstairs, you'll find three bedrooms and a full bath. Out back, a private backyard gives you room to garden, entertain, or simply unwind. Best of all, the property taxes are incredibly low, keeping your monthly costs affordable. Conveniently located with easy access to I-95, local shopping, and public transportation, this home is a great opportunity for first-time buyers and investors alike. Schedule your showing today! If you send me details like updates (kitchen, flooring, HVAC, roof), basement, or price, I can work them in so it reads less generic.

1016 Remington St, Chester

Listing courtesy of Realty ONE Group Focus. Contact:

425 Highland Ave, Chester
$175,000
**INVESTMENT OPPORTUNITY – CASH-FLOWING DUPLEX!** Huge 3-story, two-unit duplex offering an excellent opportunity for an investor or owner-occupant. The first-floor unit is currently vacant, while the second-floor unit is tenant-occupied and currently generating $1,200 per month in rental income. **Unit #1:** 2 Bedrooms, 1 Bathroom – Vacant **Unit #2:** 2 Bedrooms, 1 Bathroom – Tenant Occupied – $1,200/month The property is being sold **AS-IS**. Buyer is responsible for conducting their own due diligence, including verifying property condition, zoning, rental information, square footage, taxes, and any other property-related information deemed important. Seller and listing agent make no representations or warranties regarding the accuracy of information provided. Buyers should perform all inspections and investigations prior to settlement. A great opportunity to add a cash-flowing duplex to your investment portfolio!

425 Highland Ave, Chester

Listing courtesy of Keller Williams Main Line. Contact:

1435 Edgmont Ave, Chester
$160,000
3 Beds ⋅ 1 Baths
INVESTOR ALERT!! Build your rental portfolio or enjoy simple living!! This 3 bedroom 1 bath end of the row home is move in ready!! Tasteful updates throughout. Enter from your covered front porch into the totally open, straight thru floor plan. Large living room & dining room with laminate flooring. Kitchen also offers laminate flooring, lots of grey cabinets, stainless steel gas stove, over the stove stainless microwave, double sink & pretty backsplash. Off of the kitchen is your laundry room/mud room with back door that leads to the cute back yard & off street parking. Upstairs you will find 3 generously sized bedrooms with overhead lighting & a hall linen closet. Bathroom boasts updated grey vanity, medicine cabinet, pretty faucet, updated vanity lighting & laminate flooring. Heater & water heater & electric panel have been updated.

1435 Edgmont Ave, Chester

Listing courtesy of Keller Williams Real Estate - Media. Contact:

2732 W 2nd St, Chester
$625,000
A long time staple in Chester, PA just hit the market. Welcome to Rico's Tavern located at the intersection of 2nd and Highland Ave. The property has a main bar/lounge area that seats 20 patrons as well as a second seating area past the main bar for additional seating and 3 half bathrooms on the first level. There is a functioning commercial kitchen in the rear of the property equipped with fire suppression system with pull alarm. The kitchen comes with a commercial smoker, commercial refrigerator, deep fryer, gas range with oven, 4 station food warmer, range hood with fire suppression system, fire alarm pull system and more. The bar will be sold with all kitchen equipment, POS system used in the bar, commercial ice maker, large double door commercial refrigerator, single door commercial refrigerator, 4 wall mounted flat screen televisions in the lounge area, 2 Beer Fridges behind the bar and wired security camera system. There is also a 2 bedroom apartment that encompasses the 2nd and 3rd floor. This apartment has a living room, kitchen, dining area and full bathroom on the 2nd story and the 3rd level has 2 bedrooms. The apartment has its own entrance on Higland Ave. Bar and Liquor license will be sold together. Liquor license is Type R.

2732 W 2nd St, Chester

Listing courtesy of United Real Estate. Contact:

721 Mcilvain St, Chester
$220,000
INCOME-PRODUCING DUPLEX IN CHESTER, PA! Great opportunity to add a turnkey investment property to your portfolio or live in one unit while renting out the other to help offset your monthly housing expenses. This duplex features two one-bedroom units, each offering a private entrance, eat-in kitchen, full bathroom, and comfortable living space. The first-floor unit also provides access to the basement, offering additional storage space. Both units share access to a spacious backyard, providing valuable outdoor space to enjoy. Additional features include stainless steel appliances and a washer and dryer. Whether you're an investor looking to expand your rental portfolio or an owner-occupant looking to take advantage of the benefits of multifamily living, 721 McIlvain St offers flexibility and income-producing potential. Schedule your showing today!

721 Mcilvain St, Chester

Listing courtesy of Foraker Realty Co.. Contact:

1927 Edgmont Ave, Chester
$33,000
Exceptional opportunity! Two (2) adjoining Lots offered together. Prominently situated at Edgmont Avenue and 20th Street in Chester City. This offering includes 1927 Edgmont Avenue (49-01-01750-90) and 0 Edgmont Avenue (49-01-01751-00). Both parcels must be purchased together. Together, the Lots provide approximately 70 feet frontage on Edgmont Avenue and 100 feet depth along 20th Street.These cleared and excavated parcels offer a strong head start for residential development - without the time & expense of initial site clearing. Both Lots have been approved for construction of a new home. At this price, Buyers can secure a highly visible corner site with added frontage and greater development potential. Before redevelopment begins, Buyers must complete a reverse subdivision (lot consolidation) to combine the two (2) parcels. Buyers considering mixed-use or another development concept may also pursue any required variance or rezoning. Deeds, site information & utility-location maps are available to help support due diligence. Bring your plans and take advantage of this well-positioned opportunity!

1927 Edgmont Ave, Chester

Listing courtesy of Sam Pace & Associates. Contact:

2611 Lindsay St, Chester
$149,000
2 Beds ⋅ 2 Baths
Welcome to 2611 Lindsay St, a charming 2-bedroom, 2-bath brick twin ideally situated directly across from Chester Park. Enjoy beautiful park views and convenient access to open green space right outside your front door—perfect for relaxing, walking, or enjoying the outdoors. Inside, the home offers approximately 948 square feet of living space, hardwood floors, an eat-in kitchen, and a full unfinished basement providing additional storage and potential. The property also features a spacious rear yard on a 3,049-square-foot lot. Whether you’re a first-time homebuyer, looking for a home with a great outdoor setting, or an investor seeking a value-add opportunity, this property offers plenty of potential. Conveniently located near shopping, dining, major roadways, and everyday amenities.

2611 Lindsay St, Chester

Listing courtesy of Canaan Realty Services INC. Contact:

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