Chesterfield Homes under $500,000

Chesterfield Homes under $500,000

Welcome to Chesterfield, a charming subdivision nestled in the heart of the United States, where community spirit and modern living blend seamlessly. Known for its picturesque streets and friendly atmosphere, Chesterfield offers a warm welcome to families, professionals, and retirees alike.

One of the standout features of this delightful neighborhood is its impressive array of homes priced under $500,000. Whether you’re a first-time homebuyer or looking to downsize, Chesterfield has something for everyone. From cozy single-family homes to spacious townhouses, each property boasts unique character and charm. Many residences feature modern amenities, open floor plans, and beautiful outdoor spaces perfect for entertaining or simply enjoying a quiet evening under the stars.

Chesterfield is not just about beautiful homes; it’s also about lifestyle. The subdivision is surrounded by lush parks, scenic walking trails, and vibrant community centers, making it an ideal place for outdoor enthusiasts and families. With schools, shopping, and dining options just a stone's throw away, residents enjoy the convenience of urban living while relishing the tranquility of suburban life.

As you explore Chesterfield, you’ll discover a community that values connection and camaraderie. Neighborhood events and gatherings foster friendships and create a sense of belonging, making it easy to feel at home.

If you’re interested in finding your dream home in Chesterfield, now is the perfect time to explore the options available under $500,000. Experience the charm and warmth of this wonderful subdivision—your new home awaits!

Newest Chesterfield Homes under $500,000

2007 Eton Ct, West Chester
$480,000
3 Beds ⋅ 3 Baths
Tucked into a secluded corner of the sought-after Chesterfield community, this 3-bedroom, 2.5-bath townhome backs up to the edge of the neighborhood & green space, offering extra privacy that's hard to find in a townhome setting. Enter through a welcoming foyer with a convenient powder room, then continue into the newly updated kitchen, a highlight of the main floor with fresh finishes ready for everyday cooking and entertaining. The adjacent living area centers around a cozy fireplace and opens through sliders to a private deck, perfect for morning coffee or evening unwinding. Upstairs, the primary suite offers a peaceful retreat with double closets and a full en-suite bathroom with walk-in shower. Two additional bedrooms share a second full bathroom in the hallway, complete with a tub shower, giving everyone their own space. The walkout lower level adds even more versatility, with a finished area ideal for a home gym, media room, or hangout space, plus a dedicated laundry area. Step outside to your own patio, a great spot for enjoying the outdoors. This home also comes with a carport and an assigned parking space, so parking is never a worry. The location is a true standout, nestled within the award-winning West Chester Area School District. Neighborhood walking trails make it easy to get outside right from home, and everyday errands are a breeze with a conveniences like a shopping, dining, pharmacy, and more along West Chester Pike. With quick access to Route 352 and Route 3, trips in and around Philadelphia are a breeze. Located in the well-managed Chesterfield community, known for its quiet, no-through-traffic streets, this home is ready for its next owner. Homes in this community don't last long, so schedule your showing today.

2007 Eton Ct, West Chester

Listing courtesy of Compass Pennsylvania, LLC. Contact:

7920 Sutherland Ct, Pasadena
$305,000
2 Beds ⋅ 2 Baths
$10,000 price deduction!!! This charming Colonial townhouse in the desirable Chesterfield community offers a perfect blend of comfort and convenience. Built in 1982, this home features an inviting interior boasting with new carpeting upstairs and a spacious living room creating a cozy atmosphere throughout. The kitchen is equipped with modern stainless steel appliances, including a built-in microwave, new dishwasher, and electric oven/range, refrigerator and back splash making meal preparation a delight. A convenient laundry area is located on the lower floor, ensuring ease of use along with a new hot water heater. You will also appreciate the basement level walkout. Outside, the home has been freshly power washed and gutters cleaned out. Step outside to enjoy the community amenities, including a refreshing pool perfect for summer days, basketball and tennis courts, play ground and tot lot. Chesterfield is known for its friendly neighborhood vibe, with nearby parks offering green spaces for outdoor activities and leisurely strolls. With assigned parking for two vehicles and a low-maintenance lot size, this townhouse is perfect for those seeking a comfortable lifestyle in a welcoming environment. Experience the warmth and charm of this delightful home in Chesterfield, where community and comfort come together beautifully. Professional photos will be downloaded prior to going active.

7920 Sutherland Ct, Pasadena

Listing courtesy of Engel & Volkers Annapolis. Contact:

7907 Leeds Dr, Pasadena
$459,000
3 Beds ⋅ 3 Baths
Terrific curb appeal situated on a corner lot in the sought after Chesterfield community. This Charming Colonial-style residence offers a perfect blend of comfort and convenience. With 1,664 + square feet of thoughtfully designed living space, this home is inviting you to unwind and enjoy comfortable living. Step inside to discover a warm and inviting interior, where traditional functional warm the meets modern convenience. The spacious living area features gleaming hardwood floors, creating a cozy atmosphere for gatherings or quiet evenings at home. The gourmet kitchen is a culinary enthusiast's dream, equipped with stainless steel appliances, plantation shutters, upgraded countertops, pass thru to dining area and a generous pantry, ensuring that every meal is a delight to prepare. Retreat to the luxurious master suite, complete with a walk-in shower, walk in closet that transforms your daily routine into a spa-like experience. Two additional well-appointed bedrooms all featuring brand new carpeting provide ample space for guests or a home office, while the finished basement offers endless possibilities with a built in beverage bar, walk out stairs and half bath. Main level and upper living levels are freshly painted along with brand new roof and gutters. Outside, the property boasts a charming corner lot with sidewalks, enhancing the curb appeal with an attractive front porch with trex decking and a handsome fiberglass front door. Enjoy the serenity of your screened porch, perfect for sipping morning coffee or evening beverage of choice while soaking in the tranquil surroundings. The community amenities elevate your lifestyle, featuring a sparkling in-ground pool, tennis courts, basketball courts, and walking paths, all designed to foster a sense of community and well-being. Parking is a breeze with an attached garage, room for a second bay and additional driveway space, ensuring convenience for you and your guests. The Chesterfield community also offers a new dog park and playgrounds, making it a vibrant place to call home. This residence is not just a house; it's a lifestyle choice that embodies comfort, convenience and community. Experience the perfect blend of comfort and convenience, located in the sought after Chesapeake HS school district.

7907 Leeds Dr, Pasadena

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

3413 Halifax Ct, Pasadena
$449,000
3 Beds ⋅ 3 Baths
Welcome HOME to 3413 Halifax Ct!! Discover the charm of this beautifully maintained home nestled in the desirable Chesterfield community. This Colonial-style floor plan offers three levels of thoughtfully designed living space and numerous recent updates. Multiple living and gathering areas throughout the main level provide flexibility for entertaining, working from home, or everyday living.The heart of the home is the country-style kitchen, equipped with a dishwasher, refrigerator, microwave, and electric range. A spacious pantry provides ample storage, making meal prep a breeze. You can also step outside your kitchen door to your outside deck-overlooking your backyard, to entertain or grill!! Upstairs, you will find a generous sized primary bedroom w/private bath featuring a shower, along with two well sized bedrooms, a hall bathroom, and carpet throughout the upper level. The NEWLY REMODELED lower level adds valuable flexibility with a family room, half bath, storage area, laundry, and walkout access to YOUR covered patio, and spacious backyard! Another Benefit-Residents of Chesterfield enjoy access to community amenities including a swimming pool, tennis courts, basketball courts, volleyball courts, playgrounds, and walking trails!! Conveniently located near shopping, dining, parks, golf courses, schools, and major commuter routes including Routes 100, 2, and I-97. Don't miss your opportunity to call Halifax Ct your Own-schedule a tour today!!

3413 Halifax Ct, Pasadena

Listing courtesy of Corner House Realty. Contact:

17 Natures Way Cir, New Oxford
$370,000
4 Beds ⋅ 3 Baths
Discover the epitome of luxury living in this stunning Colonial home nestled in the desirable Chesterfield community. Built in 2024, this exquisite residence boasts 2,348 sq. ft. of meticulously designed space, featuring four spacious bedrooms and 2.5 elegantly appointed bathrooms. The heart of the home is a gourmet kitchen with a generous island, perfect for culinary enthusiasts and entertaining guests. Step outside to enjoy beautifully landscaped grounds, fenced rear yard, complete with inviting patios and porches that beckon for relaxation and outdoor gatherings. The exterior is enhanced by tasteful lighting and well-maintained sidewalks, creating a warm and welcoming ambiance. With an attached two-car garage and ample off-street parking, convenience is at your fingertips. This home offers a perfect blend of modern luxury and comfort, making it an ideal sanctuary for those seeking an exclusive lifestyle. Experience the charm and sophistication that this exceptional property has to offer. Money Back Guarantee is being offered!!

17 Natures Way Cir, New Oxford

Listing courtesy of Howard Hanna Real Estate Services-York. Contact:

7930 Sutherland Ct, Pasadena
$360,000
3 Beds ⋅ 2 Baths
Welcome Home! This end-of-row townhome offers a flexible 3-bedroom, 2-full-bath layout with plenty of space to make your own. The main level features an open-concept floor plan that flows easily between the living, dining, and kitchen areas, creating a bright and comfortable space for everyday living and entertaining. Upstairs you'll find two bedrooms along with a full bathroom. The finished lower level has been thoughtfully utilized for years as a spacious third bedroom and offers a more private setup away from the other bedrooms. With its generous size and a full bathroom on the same level, it has traditionally served as the home's primary bedroom—creating a suite-like feel and giving the home a unique separation of space. Outside, being an end unit means you'll enjoy the added benefit of a fully fenced yard with room to relax, entertain, garden, or create your own outdoor retreat. If you're looking for a townhome with an open main level, three separate sleeping spaces, two full bathrooms, a private lower-level setup, and a fenced yard, 7930 Sutherland Ct is one you'll want to see! Brand New Carpet 9/2026 & Duct work professional cleaned 9/2026. This home is also available for Rent, Listing MDAA2158556

7930 Sutherland Ct, Pasadena

Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:

1700 Newmarket Ct, West Chester
$500,000
4 Beds ⋅ 3 Baths
Welcome to 1700 Newmarket Court, a beautifully renovated four-bedroom, 2.5-bath end-unit home in the highly desirable Chesterfield community of West Chester. Thoughtfully updated throughout, this spacious home combines a fresh, modern interior with a distinctive multilevel design and exceptional flexibility. The centerpiece of the main level is the brand-new eat-in kitchen, featuring beautiful finishes, abundant cabinetry, generous counter space, and newer appliances. Hardwood flooring flows throughout the main living areas. A slightly elevated dining area creates a defined space for meals and entertaining while remaining visually connected to the step-down living room. Filled with natural light, the living room features a fireplace flanked by two sets of patio doors opening to the newly constructed deck. The second floor includes the spacious owner’s bedroom, complete with multiple windows, a skylight, ceiling fan, and a comfortable sitting nook. The owner’s bath features a separate water closet with its own sink, along with a separate makeup vanity. Two additional bedrooms, a full hall bath, and conveniently located hallway laundry complete this level. The expansive third-floor fourth bedroom features two flanking closets and offers excellent flexibility as a bedroom, home office, studio, or private retreat. The finished lower level provides valuable additional living space that is ideal for a family room, recreation area, exercise room, or home theater. This level also includes three separate utility and storage areas, a small auxiliary room offering additional workspace or storage, and a second refrigerator. All appliances are included. The end-unit setting provides additional natural light, mature landscaping, and attractive surrounding lawn. Parking includes an assigned covered carport space, an additional assigned parking space, and ample guest parking. With lawn care included, there is very little exterior upkeep to worry about—simply lock up, head out, and enjoy your beautifully renovated home and neighborhood. This is a wonderful opportunity to enjoy spacious, low-maintenance living in one of West Chester’s most desirable communities.

1700 Newmarket Ct, West Chester

Listing courtesy of RE/MAX Associates-Hockessin. Contact:

1110 Bradley Rd, Pasadena
$439,900
4 Beds ⋅ 4 Baths
Beautifully renovated 4 bedroom, 4 full bath rancher situated on a spacious half acre lot. This move in ready home features a bright, modern open layout with a stunning kitchen showcasing a large quartz waterfall island, quartz countertops, stainless steel appliances, and stylish finishes throughout. Enjoy peace of mind with a brand new HVAC system and brand new water heater. The generous half acre lot offers plenty of outdoor space for entertaining or relaxing, highlighted by a gorgeous deck overlooking the backyard. This beautifully updated home combines modern style, quality upgrades, and exceptional value don't miss this incredible opportunity.

1110 Bradley Rd, Pasadena

Listing courtesy of RE/MAX Excellence Realty. Contact:

7854 Tick Neck Rd, Pasadena
$420,000
3 Beds ⋅ 3 Baths
Welcome to this spacious and beautifully maintained home located in one of Pasadena's most sought-after communities! Enjoy an exceptional lifestyle with outstanding neighborhood amenities, including tennis courts, baseball fields, playgrounds, and a community pool complete with an active swim team. Designed for both everyday living and entertaining, this home offers generous living spaces, and a backyard retreat you'll love. Step outside to your private oasis featuring an in-ground pool, expansive patio, and a beautifully sized yard perfect for summer gatherings, relaxing weekends, and creating lasting memories with family and friends. The property is equipped with solar panels, helping to enhance energy efficiency while providing long-term savings. Combining comfort, functionality, and incredible outdoor living space, this home offers the perfect blend of convenience, recreation, and charm in the heart of Pasadena.

7854 Tick Neck Rd, Pasadena

Listing courtesy of Keller Williams Flagship. Contact:

10 Cheltenham Ln, Carlisle
$399,900
3 Beds ⋅ 2 Baths
Chesterfield is located 1.5 miles from Downtown Carlisle and Dickinson College with convenient access to Route 11, I-81, and the PA Turnpike, and close to shopping and dining. The Norwood C plan features a traditional exterior with upgraded siding, partial stone front, and shake accents. The kitchen includes upgraded cabinetry, quartz countertops, a large island with overhang, and stainless steel appliances, including an electric range, microwave hood, and dishwasher. LVT flooring is included in the great room, hall, dining room, and kitchen. The owner’s suite includes a private en suite bath, with two additional bedrooms and a full bathroom on the main floor. The home also includes a finished basement with an egress window well and a 2-car front-entry garage. Contact us for more details on this home.

10 Cheltenham Ln, Carlisle

Listing courtesy of S&A Realty, LLC. Contact:

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