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.

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

$50,000
3 Beds ⋅ 1 Baths
Investment opportunity in Chester’s Sun Village neighborhood! Located at 719 E 7th Street, this property requires a full rehab and offers a blank canvas for investors, contractors, or buyers ready to take on their next renovation project. Explore the potential to renovate for resale or add to a rental portfolio. Bring your vision and renovation plans to transform this property from the ground up. Buyers should conduct their own due diligence regarding the property’s condition, renovation requirements, and intended use.

719 E 7th St, Chester

Listing courtesy of HomeSmart Realty Advisors. Contact: 2156041191
$125,000
3 Beds ⋅ 1 Baths
Welcome to 1331 Parker St, an end-of-row home offering an exciting opportunity for a buyer ready to add their personal touch. With its desirable end-of-row position and generous potential, this property is an excellent option for a first-time homebuyer looking to build equity, a savvy investor, or a buyer searching for a renovation project with upside. While the home will require some TLC and updating, it offers a solid foundation for creating something truly special. Bring your vision, creativity, and finishing touches to transform this property into a comfortable home that reflects your style. The possibilities are here for those willing to roll up their sleeves. Whether you're looking to enter the market, create a long-term rental, or take on a project with the potential to add value, 1331 Parker St deserves a closer look. Property is being sold AS-IS.

1331 Parker St, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 6105661100
$459,900
3 Beds ⋅ 2 Baths
Welcome to 733 Main Street, where the charm and character of a unique circa-1850 period home blend beautifully with thoughtful modern updates, incredible outdoor space, and features rarely found today. Situated on a fully fenced corner lot spanning over a quarter acre, this property offers 3 bedrooms, additional finished third-floor bonus space, a huge 2+ car garage, established gardens, mature fruit and shade trees, and endless possibilities inside and out. The home's historic charm begins with a newly redone covered front porch featuring Trex decking and a striking leaded-glass front door. Extensive improvements include newer matching Pergo laminate vinyl flooring throughout the main living areas and bedrooms, fresh paint, period-style replacement windows that emulate the home's original 1850s look, newer central air and forced-air heating, a recently installed 200-amp electrical panel, updated appliances, and more. Step through the foyer and appreciate the free-flowing, flow-around floor plan connecting the kitchen, dining, and living spaces for easy entertaining. The spacious formal dining room comfortably accommodates a 6+ person table and features beautifully detailed crown molding, large double-hung windows, and a deep coat closet with built-in shelving. Continue into the bright living room, where a brick gas fireplace creates a cozy focal point alongside built-in shelving and storage, an overhead ceiling fan, and large windows bringing in plenty of natural light. The updated chef's-quality kitchen is both playful and functional, offering abundant cabinets and drawers, simulated poured-concrete laminate counters, tiled backsplash, under-cabinet lighting, and a unique built-in 6-inch antique butcher block. Thoughtful features include a pull-out Lazy Susan, pull-out cabinet drawers, movable island, LG ThinQ 5-burner gas range with air fryer, Whirlpool built-in microwave, LG dishwasher, French-door fridge with freezer drawer, and dual sink with garbage disposal overlooking the side yard. An updated and conveniently located powder room with pocket door completes the main level. Upstairs are 3 bright bedrooms with generous closet space, large windows, and ceiling fans. The primary features 3 windows and a deep closet, while a unique connecting door between two bedrooms adds to the home's original old-world charm. The updated full hall bath features a large window, newer vanity and toilet, and walk-in shower. Continue to the third floor for even more versatility. Two additional finished bonus rooms, both featuring natural hardwood flooring and ample natural light, offer endless possibilities for home offices, playrooms, hobby spaces, or additional flex space. One showcases a distinctive world-map ceiling feature, while the other includes an adjoining area ideal for a sitting room, nursery, dressing room, or walk-in closet. The clean, dry and freshly painted basement houses the Samsung front-loading washer and dryer, utility sink, high-efficiency gas furnace, 2022 Bradford White 40-gallon water heater with expansion tank, and newer 200-amp electrical panel with room for expansion. Outside is where this property truly sets itself apart. Over a quarter acre of tree-rich land is filled with manicured flower and vegetable gardens and an impressive variety of trees, including apple, Japanese Kousa dogwood, maple, oak, black walnut, plum, apricot, and Romeo cherry. The expansive level rear yard offers plenty of open space, complemented by a charming greenhouse, newer utility shed, and private newer hot tub. The large 2+ car garage features a new double-wide automatic door and opener, reinforced front floor, and built-in shelving. The fully fenced corner lot offers entrances from both Main and 8th Streets and may offer potential for subdivision or future development, subject to zoning and municipal approvals. Conveniently located in the Brookhaven/Upland area near I-95, PHL Airport, DE, shopping, dining, and everyday conveniences!

733 Main St, Brookhaven

Listing courtesy of Keller Williams Realty Wilmington. Contact: 3022991100
$49,900
3 Beds ⋅ 1 Baths
CALLING ALL INVESTORS! This property is the one you have been waiting for! This one will not last! This Property is being sold As-Is condition. 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.

1312 Terrill St, Chester

Listing courtesy of RE/MAX Select Group. Contact: 2153356900
$299,900
4 Beds ⋅ 2 Baths
Be in your new home before the holidays begin! Welcome to 3406 Oak Ln, a fully remodeled 4-bedroom, 2-bath townhome that’s move-in ready! The entire home has been freshly painted and features beautifully refinished hardwood floors throughout. The updated kitchen offers granite countertops, a breakfast bar, and stainless steel appliances. Upstairs you’ll find 3 spacious bedrooms, while the fully finished basement offers a 4th bedroom or flexible bonus space—perfect for a guest room, home office, or additional living area. Enjoy beautifully updated bathrooms, including a luxury tiled walk-in shower with an LED niche and modern LED mirror. Major improvements include NEW HVAC, NEW water heater, new carpet, and NEW windows All that's left to do is unpack, decorate, and make it home!

3406 Oak Ln, Brookhaven

Listing courtesy of Empower Real Estate, LLC. Contact: 3027382300
$279,900
3 Beds ⋅ 2 Baths
(video tour coming soon) Completely refreshed from top to bottom, this Toby Farms townhouse pairs thoughtful renovations with stylish finishes and plenty of space to make your own. The kitchen makes a statement with two-toned cabinetry, gold fixtures and hardware, upgraded countertops, and stainless steel appliances, including a built-in microwave and range. The main level features beautifully refinished hardwood floors, fresh paint, and all-new recessed lighting, giving the space a bright, clean feel while keeping the warmth and character of the home. Upstairs, LVP flooring continues into the bedrooms, including a spacious primary suite with a walk-in closet and private full bath with a stand-up shower. A second full bathroom features a tub and shower, and both bathrooms are finished with tile flooring. The finished basement adds even more usable living space with LVP flooring—perfect for a family room, home office, gym, playroom, or whatever fits your lifestyle. The entire home has been freshly painted, making it truly move-in ready. Outside, enjoy your private deck for morning coffee, entertaining, or unwinding at the end of the day. A rear-entry garage and additional driveway parking complete the package. With its fresh renovations, modern details, and flexible living space, this Toby Farms home is ready for its next owner.

4006 Gideon Rd, Brookhaven

Listing courtesy of Prime Realty Partners. Contact: 8569065885
$199,900
3 Beds ⋅ 2 Baths
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

Listing courtesy of Realty Mark Associates - KOP. Contact: 2153764444
$180,000
3 Beds ⋅ 1 Baths
Welcome to 2314 Upland, a beautifully renovated brick twin that perfectly balances modern updates with its original character. From the moment you step onto the spacious covered front porch, you’ll feel the inviting charm this home has to offer. Inside, the open living and dining area shines with gorgeous hardwood floors and a warm, neutral color palette. Fresh paint and an abundance of natural light create a bright, airy atmosphere that’s ready for your personal touch. The kitchen is a standout, featuring sleek quartz countertops, a classic tile backsplash, and clever cabinetry storage along with a dedicated pantry. It’s an efficient, stylish space that leads directly to the back porch—perfect for seamless indoor-outdoor living. The fenced rear yard, complete with a paver patio, offers a private spot for dining al fresco or enjoying a morning coffee. Upstairs, you’ll find three well-sized bedrooms, all finished with the same cozy color palette and brand-new carpeting underfoot. The full bathroom has been thoughtfully updated, boasting a modern vanity and a stall shower with a crisp, new glass door. Every inch of this home has been refreshed to provide a move-in-ready experience without losing the soulful details that make a brick twin so special. Come see for yourself how 2314 Upland blends classic style with contemporary comfort.

2314 Upland St, Chester

Listing courtesy of Compass Pennsylvania, LLC. Contact: 2673805813
$79,000
3 Beds ⋅ 1 Baths
Come check out this Diamond in the Rough, Great investment Opportunity! This 3-bedroom, 1-bathroom end-of-row town house has so much potential!! New roof installed in 2025!! With 1,114 sq. ft. of space, this property is ready for a major rehab, allowing you to customize it to your vision and maximize returns. The enclosed patio will offer a cozy outdoor retreat, perfect for relaxation or entertaining. The unfinished basement provides additional storage or the opportunity to create a functional living space. With on-street parking and a solid brick structure, the foundation is set for a lucrative investment. It's Priced right and ready to go! Don't miss your chance to transform this property and capitalize on your investment!! *All Measurements are Approximate and Not Guaranteed.

1228 Clover Ln, Chester

Listing courtesy of United Real Estate. Contact: (484) 367-7727
$115,000
3 Beds ⋅ 1 Baths
Newly Updated for your approval! 1220 W 9th st Is ready for its new owner, come see what Chester has to offer, Move In Ready!

1220 W 9th St, Chester

Listing courtesy of JMG Pennsylvania. Contact: 8334263567
$185,000
3 Beds ⋅ 1 Baths
Recently updated twin close to everything. Bus, train, shopping I95 access. Currently occupied by tenants that are leaving. Enter the front screened in porch great for sitting and enjoying then into the large living room with lots of light and ceiling fan. Behind the living room is a large dining room perfect for larger gatherings. In the rear is the kitchen with Stainless Steele appliances, newer cabinets, and gas cooking. Upstairs you'll find 3 ample sized bedrooms and an updated hall bath with beautiful tile. There is newer LVP flooring throughout the home and there is a fenced in rear yard. Heating is also gas. Time to call this one home. Seller is selling this one as-is.

745 Engle St, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (610) 892-8300
$169,000
3 Beds ⋅ 2 Baths
Come and get it! Fixer-upper opportunity in Chester featuring 3 bedrooms and 1 full bathroom. Great opportunity for an investor looking for their next project. Property needs extensive renovations and is being sold 100% as-is. Buyer is responsible for all inspections, due diligence, and any required township and/or state inspections, certifications, or repairs. Seller will make no repairs or concessions. Schedule your showing today!

316 E 24th St, Chester

Listing courtesy of Prime Realty Partners. Contact: 8569065885
Start Your Search