Explore Homes for Sale in Chester, NJ
Map Search for Chester, NJ Homes for Sale

Chester NJ Homes For Sale | The Courtney Orlando Group

  Advanced Search   Market Reports   Home Value   Connect

Discover an exquisite selection of homes for sale in Chester, NJ, presented by The Courtney Orlando Group. Chester, New Jersey, offers a unique blend of historic charm, upscale amenities, and a sought-after suburban lifestyle. From elegant Colonials in established neighborhoods to custom-built estates on expansive lots, our listings cater to diverse preferences. Explore properties near top-rated West Morris Central High School and the scenic attractions like Hacklebarney State Park. Whether you seek a family-friendly community or a serene retreat, finding your dream home in Chester begins here, with comprehensive market insights and local expertise.

Search Chester, NJ by Lifestyle
Search Chester, NJ by Price
Search Chester, NJ by Bedrooms
Search Chester, NJ by Bathrooms

Exploring Homes For Sale in Chester, NJ

Chester, New Jersey, is a coveted destination for homebuyers seeking a perfect blend of rural tranquility and sophisticated suburban living. The journey to finding your ideal residence among the numerous homes for sale in this charming Morris County town is made seamless with the expertise of The Courtney Orlando Group. This community is celebrated for its historic downtown, top-tier schools, and an abundance of recreational opportunities, making it a prime choice for families and professionals alike.

Diverse Home Styles and Neighborhoods in Chester

The real estate landscape in Chester, NJ, is incredibly varied, offering something for every taste and budget. Prospective buyers will find an impressive array of homes for sale, from classic Colonial and spacious Cape Cod residences that exude traditional charm to modern custom builds featuring contemporary design and amenities. Furthermore, one can also find luxurious sprawling ranches that often include significant acreage, perfect for those seeking privacy or even equestrian pursuits. Esteemed neighborhoods such as Spring Lake and Pleasant Hill offer distinct living experiences, each with unique architectural styles and community atmospheres. For those interested in new constructions, pockets of newer developments periodically offer state-of-the-art homes designed for modern living.

Chester's Lifestyle and Community Appeal

Beyond the brick and mortar, the appeal of homes for sale in Chester, NJ, is deeply rooted in the town's vibrant lifestyle and strong community spirit. Residents enjoy access to a highly-regarded public school system, including the excellent West Morris Central High School, making it a draw for families. The charming historic downtown area boasts unique boutiques, antique shops, and diverse dining options, fostering a lively local economy and a strong sense of community. Outdoor enthusiasts will appreciate the proximity to natural beauty, with places like Hacklebarney State Park and the Patriots’ Path offering endless opportunities for hiking, biking, and exploring. The town also hosts various seasonal events and farmer's markets, enhancing its small-town charm while providing ample local activities.

The Chester Real Estate Market: What Buyers Need to Know

Navigating the real estate market for homes for sale in Chester, NJ, requires up-to-date knowledge and local insight. The market here is often characterized by steady demand due to the town's desirable attributes. Properties range from entry-level single-family homes to magnificent luxury estates, with price points reflecting the quality of construction, acreage, and location within Chester. Understanding current market trends, average days on market, and property values is crucial for making informed decisions. The Courtney Orlando Group provides invaluable market analysis, helping buyers discern opportunities and achieve their real estate goals in this competitive yet rewarding market. We monitor new listings diligently, ensuring our clients have access to the latest properties entering the market.

Finding Your Dream Home with The Courtney Orlando Group

When you embark on the search for homes for sale in Chester, NJ, partnering with a knowledgeable and dedicated team is paramount. The Courtney Orlando Group possesses an unparalleled understanding of the Chester real estate landscape, from its hidden gems to its most sought-after addresses. We pride ourselves on providing personalized service, leveraging our local expertise to match you with properties that align perfectly with your lifestyle needs and investment objectives. From initial property searches to navigating the closing process, our team is committed to making your home-buying experience seamless and successful. Discover why so many choose Chester as their forever home, and let us guide you every step of the way.

Newest Homes for Sale in Chester, NJ

$825,000
4 Beds ⋅ 2.1 Baths ⋅ 4028202 MLS
Rare opportunity to build your ultimate custom dream home on 12.5 private, rolling acres in prestigious Chester Township! Nestled in the desirable R2 zone, this unique flag lot offers the ultimate in privacy and seclusion. The property is beautifully wooded and currently farm-assessed under a woodland management plan, offering significant tax benefits. The land opens up to a spectacular hilltop crest where the current home sits, boasting breathtaking, panoramic views that truly go on forever. Imagine waking up to endless horizons and designing a custom estate that perfectly frames these unmatched vistas. The acreage directly adjoins the pristine Black River Wildlife Management Area, providing a permanent natural buffer, tranquil surroundings, and effortless access to outdoor recreation right in your backyard. Please note: The existing home on the property is currently occupied but is considered a tear-down and is being sold strictly in "as-is" condition. Value is entirely in this incredible land. All visitors must have a confirmed appointment prior to entering the property absolutely no trespassing. Buyers are responsible for conducting their own due diligence regarding building requirements, variances, and utilities. Bring your architect, bring your vision, and claim one of Chester's finest view lots today! Capacity and condition of septic is unknown. Well on site.

250 Pleasant Hill Rd, Chester Twp.
$825,000
4028197 MLS
Rare opportunity to build your ultimate custom dream home on 12.5 private, rolling acres in prestigious Chester Township! Nestled in the desirable R2 zone, this unique flag lot offers the ultimate in privacy and seclusion. The property is beautifully wooded and currently farm-assessed under a woodland management plan, offering significant tax benefits. The land opens up to a spectacular hilltop crest where the current home sits, boasting breathtaking, panoramic views that truly go on forever. Imagine waking up to endless horizons and designing a custom estate that perfectly frames these unmatched vistas. The acreage directly adjoins the pristine Black River Wildlife Management Area, providing a permanent natural buffer, tranquil surroundings, and effortless access to outdoor recreation right in your backyard. Please note: The existing home on the property is currently occupied but is considered a tear-down and is being sold strictly in "as-is" condition. Value is entirely in this incredible land. All visitors must have a confirmed appointment prior to entering the property?absolutely no trespassing. Buyers are responsible for conducting their own due diligence regarding building requirements, variances, and utilities. Bring your architect, bring your vision, and claim one of Chester?s finest view lots today!

250 Pleasant Hill Rd, Chester Twp.
$1,499,000
4 Beds ⋅ 4.2 Baths ⋅ 4026921 MLS
Beautifully maintained stone front center hall colonial in much desired Highland Farm section of Chester Township. Private end of cul-de-sac location complete with patio, built in grill, professional landscaping and paver driveway. Two story great room with wood burning fireplace opens to kitchen which comes equipped with stainless steel appliances including oversized sub zero refrigerator and double oven as well as five burner gas stove. Large formal living room continues to a stunning conservatory with oversized windows for natural light any time of day. Library/Office has recently renovated full bath. Large primary suite with fireplace, two walk in closets, sitting area which includes private deck overlooking rear of yard. Additional ensuite bedroom with updated shower complete with Pulse Makena shower spa panel system. Two additional bedrooms enjoy a jack and jill bathroom also complete with Pulse Makena shower spa. Finished lower level has home theatre, wet bar, recreation area as well as separate space for home gym. This home comes complete with a whole house generator.

8 Peach Tree Ln, Chester Twp.
$275,000
4024127 MLS
Nestled in the affluent Mendham-Chester area, this 1400 sq ft Classical Pilates Studio offers a truly bespoke wellness experience. Built from the ground up with elegant design $100K+ investment featuring maple floors, custom dimmable lighting, and mirrored walls. $50K+ in mostly new Pilates Gratz equipment and an additional $20K in wool area rugs and high-end furnishings. Since 2018, this well appointed studio has cultivated an established brand and local presence recognized for its commitment to Classical Pilates along with a lucrative devoted base of 400 clients. With a primary focus on private sessions, the business reflects high-touch service and rare expertise. This turnkey operation with "no debt" is poised for growth, waiting for its next steward to build on a legacy of wellness, precision, and luxury. Seller would be agreeable to a compensated transitional period.

427 Route 24, Chester Twp.
$2,199,000
4 Beds ⋅ 3.3 Baths ⋅ 4023996 MLS
This is not a typical custom home. It is a private entertainment experience paired with luxury everyday living. Located approximately one hour from Manhattan with the train located 2 miles away, this extraordinary residence offers privacy, sweeping views from every level, and a lifestyle rarely found in a single property. At the heart of the home is a meticulously designed entertainment level, created as a village with cobblestone streets lined with shops for guests to enjoy. This level features a poker & billiards room, a lounge with a 29' bar, a soda shop, a wine shop, a bakery, an arcade, a pretzel stand, a coffee kiosk, a hot dog stand and a 20 seat movie theater with ticket booth and full concession area.On the main living level the home offers a richly appointed mahogany and leather cigar/smoking room. The home extends seamlessly to the outdoors offering a 4 year old inground pool. The huge primary suite has a soaring 20' ceiling and includes a sauna and a steam shower. There is also a large office/studio with soaring ceilings, spectacular views, and includes a powder room and full kitchen. The office has an outside entrance, but is also accessible from the primary suite. For those seeking something truly different, this home offers not just space, but a luxury lifestyle.

2 Chilton Rd, Chester Twp.
$1,049,000
4 Beds ⋅ 3 Baths ⋅ 4018818 MLS
Welcome to this fully renovated, move-in ready ranch-style home w/ 4 bedrooms & 3 full bathrooms, set on over 3 private, scenic acres in the heart of Chester Township. Thoughtfully updated, this home blends classic charm w/ modern finishes, offering single-level living with bright, open-concept spaces designed for comfort & style. The custom kitchen features high-end appliances, and a layout perfect for cooking and entertaining. Throughout the home, enjoy refinished hardwood floors, updated bathrooms, and new windows that fill the space with natural light. Major upgrades include new siding, roof, plumbing, electrical, and an HVAC system with a high-efficiency boiler. Both the main house & detached building benefit from updated septic systems. The finished lower level, with a private entrance, is currently used as an au pair suite ideal for , guests, or a in law suite setup. Step outside to your private backyard oasis w/ a renovated in-ground pool featuring new plaster, plumbing, & equipment ideal for entertaining. The expansive lot offers plenty of space for recreation, gardening, or quiet enjoyment. A detached second building adds flexibility as a possible guest house, office, studio, or workshop. Located minutes from top-rated schools, downtown Chester, parks, shopping, & commuter routes, this property offers a rare mix of modern systems, flexible living space, & peaceful surroundings a truly turn-key home in one of Morris County's most desirable areas.

1625 Route206, Chester Twp.
$649,999
4 Beds ⋅ 2 Baths ⋅ 4017356 MLS
Welcome to one of Chester Township's best values a beautifully renovated 4-bedroom, 2-bath ranch offering the perfect blend of modern updates, timeless charm, and peaceful country living. Set on a picturesque lot backing to preserved Green Acres, this move-in-ready home offers privacy, space, and convenience just minutes from downtown Chester. From the moment you arrive, you'll appreciate the extensive improvements, including a brand-new roof, new blacktop driveway, new masonry front steps, new central air conditioning, 200-amp electrical service, new water softener, and newer water heater. Inside, you'll find a bright, open floor plan with beautiful hardwood floors, oversized windows, and abundant natural light. The spacious living and family rooms, highlighted by a fireplace, provide the perfect space for entertaining. The updated kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and a generous dining area. Step outside to the expansive deck overlooking a private backyard backing to preserved Green Acres. Additional features include an unfinished basement with excellent storage or future expansion potential, natural gas, well water, and septic. Located near award-winning schools, shops, restaurants, parks, golf courses, equestrian facilities, and major commuting routes. Some listing photographs have been virtually staged. Furniture shown are for illustration only and are not included in the sale.

356 North Rd, Chester Twp.
$229,000
4016502 MLS
1128 SQ. FT. PROFESSIONAL OR MEDICAL OFFICE CONDO IN PRIME CHESTER LOCATION 2ND FLOOR, 4 OFFICES, REC, WAITING ROOM & STORAGE. Two private work areas near the entrance flow into a spacious lab area featuring quartz countertops, existing vacuum (suction) line connections, and an included furnace. This newly renovated 1,128 sq. ft. office space offers a half bath at the entry and a full bathroom with a stall shower within the unit. Upgrades include new flooring, cabinetry, fixtures, and high-end tile finishes throughout. Zoned for office/professional use per the township and previously utilized as a medical manufacturing facility. Ample parking and excellent visibility at a prime corner location on Main Street and Route 24 in the heart of Chester Borough.

530 EA Main St unit 5B, Chester Boro
$135,000
4012381 MLS
Highly respected and successful yarn boutique and gift shop in the vibrant & historic destination town of Chester. Excellent location with great visibility on Main Street. Turn key business selling high quality knitting, crochet and fiber art supplies, as well as original art and craftwork. A member of the supportive Historic Chester Business Association. Extensive customer list and full schedule of fiber art classes. Nine plus years of continuous growth. Tax returns and P&L statements available on request. Sale includes the established business name and good will, customer list (7370+), furniture and displays, custom lighting, brand new POS system, security equipment, holiday decorations/display items, store supplies. Inventory (currently approximately $115,000) handled separately.

44 Main St, Chester Boro
$3,000,000
4 Beds ⋅ 4.1 Baths ⋅ 4004191 MLS
Old Fox Farm is a true equestrian's dream. Originally part of the Luce estate, this exceptional property offers 25 +/- acres of preserved farmland with an approximately 4,100 square-foot residence featuring an updated kitchen, detached four-car garage with a hydraulic lift for an additional vehicle, a two-car garage, and a Hitchings & Company greenhouse. Two barns contain a total of 20 stalls with Dutch doors, an 65 ft x 140 ft indoor ring with GGT footing and viewing area, 196 ft x 88 ft outdoor ring with sandstone and dust footing, 14 grass paddocks, five stone dust indoor/outdoor wash stalls, three tack rooms, a kitchen, laundry, bath and a substantial hay barn. The charming residence was expanded by architect William Byrne in 2005 using the style of a traditional Federal farmhouse replete with a covered wraparound porch.

450 Old Chester Rd, Chester Twp.
$300,000
3983616 MLS
Welcome to Your Dream Canvas, nestled in the heart of Chester Township, New Jersey. This property offers a rare opportunity to transform it into the home of your dreams. Located in a highly sought-after area, this property boasts exceptional potential & a private, serene lifestyle. Zoned for a single-family home, the former foundation is in place & there is also a foundation for a 4-car garage. 1000-gal septic is in place. Imagine driving up your long driveway to your custom oasis built to your unique tastes and needs. Don't miss your chance to turn this diamond in the rough into your forever home. Property sold completely AS-IS/WHERE-IS. The value of this property lies in the land itself. With its prime location, mostly level lot, and privacy, it's a unique find in the Chester area. Cash or renovation loans are the preferred financing options for this property.

559 State Route 24, Chester Twp.
$4,500,000
6 Beds ⋅ 8.2 Baths ⋅ 3964253 MLS
Kestrel Ridge: A home of extraordinary quality and space sits privately on a hillside outside of the village of Pottersville in Chester Township, enjoying the passive recreation benefits of neighboring Hacklebarney Park. A gated entry leads to a courtyard edged by a waterfall and maturely landscaped grounds. The meticulously crafted stone exterior and hand-carved wood features inside lend a European style to the 8055 sq ft home. A 2-story entry hall with domed ceiling opens to an equally inspiring Great Rm with a massive stone fireplace. Occupying one entire end of the first floor, the primary bedroom suite includes an office; BR with fireplace; exercise room; spacious double closet rooms and double full baths. A library/office is nearby. The dining room and kitchen are designed with amenities for a master chef. A breakfast room with fireplace adjoins the stone terrace spanning the back of the home. The 2nd floor is dedicated to 3 secondary BR,2 with fireplaces and all with ensuite baths. Off the back stairs a 3-room apartment provides independent living accommodations. The 3981 sq ft lower level is dedicated to entertainment and recreation with a 22-seat home theater; bar area; media room with fireplace; game room; guest suite, and hobby/wrapping room. Completing the resort-like facilities at Kestrel Ridge: the sequestered pool complex features a Gunite pool with waterfall; stone pool house with kitchen, dining area, laundry, separate bathroom and sauna; and a barbecue area.

770 Pottersville Rd, Chester Twp.
Start Your Search

The data displayed relating to real estate for sale comes in part from the IDX Program of Garden State Multiple Listing Service, L.L.C. Real estate listings held by other brokerage firms are marked as IDX Listing.
The information being provided is for the 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.
Information deemed reliable but not guaranteed.
Copyright 2026 Garden State Multiple Listing Service, L.L.C. All rights reserved.

Updated: