Explore Homes for Sale in Chester, NJ
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Chester NJ Homes For Sale | The Courtney Orlando Group

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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.

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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

$649,000
3 Beds ⋅ 2 Baths ⋅ 4052046 MLS
Tucked away on a tranquil, private street across two sprawling acres, this home offers privacy and curb appeal. Every exterior detail has been thoughtfully updated for absolute peace of mind, showcasing a brand-new roof, siding, windows, a newly paved driveway with ample parking, and a spacious two-car garage. Step through the front door into an airy, bright interior anchored by durable luxury laminate flooring that flows seamlessly throughout. The open-concept floor plan connects your spaces with ease, highlighted by an oversized living room drenched in natural light that serves as a welcoming centerpiece for relaxing and entertaining. The showpiece chef?s kitchen is designed to impress, featuring gleaming quartz countertops, brand-new stainless appliances, and generous prep space that makes entertaining a breeze.This home offers three generously sized bedrooms and two fully renovated, designer-inspired full bathrooms. Downstairs, the full, partially finished basement expands your living footprint significantly, providing versatile space for a home theater, gym, playroom, or dedicated office while still leaving plenty of room for all your storage needs. Just a short drive from downtown Chester with its boutique shopping, seasonal markets, and renowned local dining, as well as major highways providing an easy route straight into NYC. For convenience, the home is situated just one mile from the local elementary school and close distance to the nationally ranked high school.

26 Cooper Ln, Chester Twp.
$1,995,000
4 Beds ⋅ 5.1 Baths ⋅ 4051010 MLS
Nestled on a hillside in one of Chester Twp's loveliest east side cul-de-sac neighborhoods, this sprawling 5700sq/ft estate represents a rare convergence of scale, privacy & craftsmanship on 3.5+ acres of professionally landscaped grounds. A bluestone walkway w/ fountain leads to the front porch w/ balustrades overlooking the Roxiticus Valley. Enter through the double doors into the 2 story foyer. This 4 bed/5.1 bath home allows entertaining in generous open spaces. The chef's kitchen is appointed w/ Plato custom cabinetry, 2 dishwashers, Thermador prof. appliances, a wine fridge, built-in buffet & walk-in pantry. The large sunlit breakfast rm overlooks the expansive 1800sq/ft deck w/ 2 gazebos & a hot tub. The main level offers a dbl-sided FP between the dining & great rms, a flexible office/guest suite w/ full bath & a living rm w/ French doors opening to the front porch. Upstairs, the primary suite incl a sitting rm, a soaring custom FP, 2 walk-in closets, a grand bathrm w/ jetted tub, water closet w/ bidet & a walk-in shower. Two additional en suites & a 4th bedrm complete this level. The finished LL features a full kitchen, theater, exercise rm, spirits rm, full bath, rec. rm & stairs to the oversized 3 car garage w/ EV charger. Outside, there is a commercial whole house generator & a large custom built shed w/ rollup garage door. Whether hosting large gatherings or enjoying quiet country mornings, this property delivers a lifestyle defined by comfort & elegance.

6 Hickory Dr, Chester Twp.
$1,669,000
4 Beds ⋅ 3.2 Baths ⋅ 4050893 MLS
Flawless custom Colonial featuring a natural stone fireplace, dramatic volume ceilings, rich custom millworker, & hardwood flooring throughout. Set back majestically on a 2.47 acre cul-de-sac parcel in the coveted Hedgerows section of east Chester Township, this remarkable one-of-a-kind residence is part of a welcoming enclave of 39 custom-built homes inspired by late 18th century New England design. Each home is admired for its distinctive architecture, impeccable craftsmanship, & exceptional attention to detail. This wonderful home offers 13 rooms, including 4 airy bedrooms each with generous closets, hardwood flooring, & bright windows, plus 3 renovated full baths, and 2 powder rooms. Elegant living spaces include a gracious living room with gas fireplace flanked by beautiful built-ins, a magnificent open concept family room with soaring vaulted ceiling, commanding fieldstone gas fireplace, & convenient back staircase, plus a spacious formal dining room. The updated designer kitchen showcases leathered granite countertops, a center island, and premium appliances, while the handsome home office features abundant custom built ins. The secluded primary suite is a serene retreat with a distinctive cupola skylight, comfortable sitting room, and walk-in dressing room. With more than 4,100 sq ft of inviting living space across the 2 main levels, this captivating home also features a sprawling finished lower level. 3 car attached garage, whole house generator plus fenced yard.

7 Red Oak Row, Chester Twp.
$45,000
2 Beds ⋅ 1 Baths ⋅ 4050305 MLS
Welcome to Windy Acres, a charming 55+ manufactured home community located in the heart of beautiful Chester Boro, NJ! This well-maintained 50-pad community offers convenience, comfort, and a wonderful lifestyle close to everything Chester has to offer. Unit J is being offered AS-IS as part of an estate and is priced for a quick sale, providing an opportunity for the new owner to add their personal touch and make the home their own. The unit has been emptied and professionally cleaned, making it ready for its next chapter. Enjoy a prime location just a half mile from historic downtown Chester and directly across from the Chester Library and Chubb Park. The front of the home offers views of Alstede Farms' picturesque peach orchard. Conveniently located near shopping, local farms, trails and major commuting routes. Windy Acres ground lease required. The ground lease includes water, sewer, trash removal, and snow removal. Buyer to verify all fees and monthly ground lease rate with Property Manager. No property taxes.

195 W Main St, Unit J, Chester Boro
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 4050166 MLS
Completely renovated from top to bottom, this exceptional Expanded Ranch offers approximately 4,700 SF of living space on 1.5 acres, featuring 4 bedrooms and 4 full bathrooms. The main residence welcomes you with an expansive, open, naturally light-filled layout, new flooring, cathedral ceilings, and a stunning oversized kitchen with abundant cabinetry, granite countertops, and new stainless-steel appliances. The first floor features a spacious primary suite with walk-in closet and full bath, formal dining room, living room, huge family room, and updated full bath. The second floor includes a bedroom, full bath, and bright flex room with skylights. A breezeway connects to additional living space featuring a kitchenette, dining and living rooms, 2 bedrooms, full bath, and office. The main home includes a partially finished basement, while the additional living area offers an unfinished basement for extra storage. Enjoy patios, beautiful landscaping, and a fully fenced yard backing to the Black River Game Preserve. Town-approved permits for two garages are in place and ready for the new owner to begin construction. Chester Schools and West Morris Mendham High School; Randolph mailing address 07869. An exceptional property offering space, flexibility, privacy, and a beautiful setting.

46 Ironia Rd, Chester Twp.
$1,099,900
5 Beds ⋅ 5.2 Baths ⋅ 4048684 MLS
A rare opportunity on 2 usable acres! This custom colonial was fully renovated in 2023 quartz kitchen, stainless appliances, and a flexible layout throughout. 5 bedrooms, 5 full baths, 2 half baths, plus bonus living space and a 2-car attached garage. Chester Schools / West Morris Mendham HS (IB Program). Sold As Is.

2 Twin Brooks Trl, Chester Twp.
$1,350
4046032 MLS
OFFICE SPACES AVAILABLE - GROSS LEASE- LANDLORD PAYS UTILITIES. CONVENIENT LOCATION TO HIGHWAYS, SHOPS, AND RESTAURANTS. 2nd FLOOR 2A 730 SF @ $1,350mo, and 2B 730 SF @$1,350/mo. Units 2A & 2B can be combined (1,460 SF) @ $2,700/mo.

154 ROUTE 206, Chester Twp.
$1,299,000
4 Beds ⋅ 4 Baths ⋅ 4045369 MLS
Tucked at the end of a quiet cul-de-sac on 4.73 private acres, this fully renovated Chester Township home offers the combination buyers are always looking for: privacy, usable space, a great location, and absolutely nothing to do but move in.With 4,437 square feet of living space, the home has been completely updated within the last two years. The heart of the home is the renovated chef?s kitchen, featuring quartz countertops, Café appliances, generous storage, and an open layout that makes everyday living and entertaining easy.Throughout the home, you?ll find custom millwork and shadow-box molding, recessed lighting, newer interior doors, fresh paint inside and out, and beautifully renovated bathrooms, including the primary bath. A flexible first-floor room works perfectly as a home office, playroom, guest space, or additional living area. Outside, nearly five private acres are surrounded by mature trees, creating a peaceful setting that feels tucked away while still being just minutes from downtown Chester?s restaurants, shops, parks, and everyday conveniences. Located in Chester Township with highly rated Chester schools and convenient access to Routes 206, 24, and 287, this is an ideal option for buyers looking for a move-in-ready home with acreage, privacy, and an easy commute in Morris County, NJ. With relocation prompting the sale, this is a rare opportunity to own a truly turnkey home in one of Chester Township?s most private cul-de-sac settings.

31 Warren Cutting, Chester Twp.
$1,295,000
4 Beds ⋅ 3.1 Baths ⋅ 4045232 MLS
Exceptional custom Colonial featuring a spectacular chef's kitchen with premium GE Monogram appliances, including a built-in refrigerator and freezer, range, dishwasher, an oversized center island with built-in microwave and wine storage, and door in the kitchen that leads to a private backyard perfect for entertaining. This beautifully designed home offers 4 bedrooms, 3.1 baths, an open floor plan with 10-foot ceilings on the main level, elegant marble flooring flowing into hardwood floors, and extensive custom moldings throughout. Enjoy multiple living spaces including a family room, formal living room, sunroom, private office, wet bar, and convenient first-floor laundry. The luxurious primary suite features a sitting room with a fireplace, spacious walk-in closets, and a spa-inspired bath with granite finishes. Two secondary bedrooms share a Jack-and-Jill bath. Additional highlights include 3 fireplaces (2 gas, 1 wood-burning), granite countertops in all bathrooms, an unfinished walk-out basement ready for future expansion, an attached 3-car garage, blacktop driveway, and a beautifully private setting. A rare opportunity to own a thoughtfully designed luxury home in one of Chester's most desirable locations.

49 Parker Rd, Chester Twp.
$850,000
4 Beds ⋅ 3 Baths ⋅ 4045090 MLS
Straight from a movie set - Storybook setting in the quaint Township of Chester, 1823 colonial farmhouse with rocking chair porch, large enough for entertaining, overlooks perennial beds, picket fences and rolling hills! Authentic architectural Details combined with modern conveniences make this charming period home one that can't be missed! Guest suite with kitchenette, full bath and separate entrance. Two working fireplaces includes fireplace tools, pokers, ash shovel, tongs, brush and hanging hooks. In ground pool, outbuildings, mini-barns, pumpkin pine flooring throughout the home, beamed ceilings, 2 fireplaces, 2018 septic, 4 acres of privacy and brick pathways all contribute to the character of this gorgeous gem! Chicken coop and outdoor run is relatively new and can house 25 hens. Fenced-in field with small barn can hold a pony, goats and sheep (Owner had sheep and goats). The Herb Barn is storage for gardening tools and opens into an Award Winning colonial brick garden with fruit trees (apple, pear and quince) and currants and blueberries. Plenty of space to grow vegetables. Minutes to downtown Chester, a short drive to Routes 80 and 78, NJ Transit and Chester Schools along with Mendham High School make this home highly desirable. Lot to the right of the house is part of the property, possible location for a garage. Fireplace and Chimney are as is with no known issues.

32 Tanners Brook Rd, Chester Twp.
$799,000
4 Beds ⋅ 3.1 Baths ⋅ 4042566 MLS
Welcome to this thoughtfully designed home offering timeless character and exceptional spaces for everyday living and entertaining. Lovingly maintained, this 4-bedroom, 3.5-bath Colonial is situated on a private 2-acre lot on one of Chester Township's most sought-after streets.The main level features an eat-in kitchen with direct access to the deck, creating seamless indoor-outdoor living, along with a spacious family room, formal dining room, and inviting living room filled with natural light. Upstairs, the expansive primary suite offers a sitting area overlooking the woodlands, an en-suite bath, and dual closets. Three additional bedrooms, each with a walk-in closet, share a full hall bath. The walk-out lower level provides outstanding flexibility with a secondary suite complete with a kitchenette, full bath, and two additional rooms?ideal for guests, extended living, or a home office.Enjoy the peaceful setting from the upper and lower decks overlooking the wooded Mt. Paul green space. Additional features include a natural gas automatic generator.Conveniently located on the east side of Chester Township, just minutes from the charming downtowns of Chester and Mendham, parks, farms, athletic fields, preserved open space, the train station, and major highways. Chester is renowned for its strong sense of community, top-rated schools, and seasonal festivals.Experience the space, setting, and lifestyle this exceptional home has to offer.

9 E Fox Chase Rd, Chester Twp.
$175,000
4041881 MLS
1,000 SF OFFICE IN CHESTER WOODS PROF. PARK OFFICE COMPLEX FRONTS ON RT. 24, COUNTRY SETTING. REC. AREA, 5 OFFICES, PRIVATE BATHROOM. CAN BE SUBDIVIDED.

385 State Route 24, Chester Twp.
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