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

$1,150,000
4 Beds ⋅ 2.1 Baths ⋅ 4043321 MLS
A quintessential Chester Township country estate where privacy, acreage, and lifestyle come together. Set on 6.7 picturesque acres adjacent to preserved land, this custom Colonial offers an exceptional setting with expansive lawns, white fencing, and classic pastoral views.Inside, grandly proportioned rooms feature hardwood floors, multiple fireplaces, custom built-ins, and abundant natural light. A welcoming foyer with custom tile leads to a formal living room with a brick fireplace and French doors. The formal dining room boasts crown and chair-rail molding, while a dedicated home office features custom built-ins and an oversized picture window. The spacious kitchen includes white cabinetry, granite counters, stainless appliances, and a charming breakfast bay window. Anchored by a stone fireplace, the family room opens directly to an expansive deck.The primary suite offers a cozy fireplace, walk-in closet, and a spa-inspired bath with a custom waterfall shower. Three additional bedrooms and an updated full bath complete the second level. Below, the finished lower level provides versatile space for recreation, a gym, or media room.Outdoors, enjoy a private heated pool and patio, huge deck, two-stall horse barn with partitioned pasture, paddock, an adjacent round pen, greenhouse, chicken pen, plus a hoop shed and garden shed for extra storage. 200 Lamerson Road presents a rare opportunity for luxury country living in prestigious Morris County.

200 Lamerson 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.
$699,000
3 Beds ⋅ 2.1 Baths ⋅ 4042373 MLS
Rare opportunity to own a one-of-a-kind ranch set on a picturesque property in Chester, offering the perfect blend of comfortable living and exceptional space for hobbies, animals, etc. The main home features 3 bedrooms, 2.5 baths, an eat-in kitchen, spacious living room with a fireplace, primary ensuite, convenient first-floor laundry, and an oversized attached garage. The basement offers both finished and unfinished areas with multiple rooms, abundant storage, and a wood-burning stove. Step outside to a beautiful 2-tier deck overlooking the peaceful property. What truly sets this home apart is the incredible detached outbuilding. Previously used as a 6-dog kennel, this expansive structure also includes a large insulated addition offering garage/storage space for up to 6 vehicles, a half bath, separate septic system, cooling for the addition, and endless possibilities for car enthusiasts, contractors, hobbyists, or business use. Two oversized RV awnings provide even more covered storage. The grounds are equally impressive, featuring a fenced pasture that's perfect for horses or other animals, two driveways connected by a semicircle drive for easy access, and ample parking for guests and equipment. Additional highlights include a 2-stage water treatment system, whole-house generator, and both septic systems (home verified for 3 bedrooms) to be tested prior to closing. A truly unique property offering space, privacy, and flexibility that's hard to find.

20 Cora Ln, Chester Twp.
$1,399,000
4 Beds ⋅ 3.1 Baths ⋅ 4042094 MLS
First time ever offered for sale, this immaculate brick-front Center Hall Colonial is nestled on a breathtaking 2-acre property in one of Chester's most sought-after locations. A picturesque tree-lined driveway welcomes you to this private retreat surrounded by mature landscaping, lush greenery, and exceptional curb appeal. The inviting floor plan features an elegant formal dining room, a sun-filled sitting room, and an updated white eat-in kitchen with premium Wolf stainless steel appliances, a large center island, abundant cabinetry, and generous storage. The kitchen flows seamlessly into the spectacular family room featuring soaring vaulted ceilings, a striking fireplace, and custom windows overlooking the scenic grounds. A 1st-floor flex room, full bath, PR, laundry room, secondary entrance & 3 car garage complete the main level. Upstairs, the luxurious primary suite offers dual walk-in closets and a spa-inspired bath with a soaking tub and separate stall shower. Three additional spacious bedrooms, a full bath, and an oversized bonus room provide flexibility for today's lifestyle. The newly finished walkout lower level expands the living space with a recreation room, full bath, exercise room, additional bedroom, and more storage. Relax or entertain on the expansive deck overlooking the private backyard. Combining timeless elegance, modern updates & a serene Chester setting, this meticulously maintained home presents a rare opportunity to own a truly exceptional property.

13 Hunters Trl, 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.
$1,300,000
4 Beds ⋅ 5.1 Baths ⋅ 4041680 MLS
A rare opportunity to own a custom-built estate offering exceptional craftsmanship, unmatched versatility & incredible privacy on nearly 2 acres in Chester adjacent to Patriots' Path. Whether you're seeking a private retreat, space for your hobbies or the ultimate workshop, this one-of-a-kind property delivers. The home features 4 spacious bedrooms, multiple bonus rooms & 4 full baths, providing a flexible floor plan to accommodate today's lifestyle. Thoughtfully designed & impeccably maintained, every detail reflects pride of ownership and quality construction. The impressive detached building is a true standout. The possibilities are endless. Ideal for car enthusiasts, contractors, landscapers, woodworkers, artists, hobbyists, or anyone in need of exceptional workspace. Built with efficiency and year-round comfort in mind, the detached structure features R-19 insulated walls, R-38 ceiling insulation, perimeter wall insulation extending 4 feet below grade with 2-inch insulation, NEW HVAC & never dropping below 40 degrees. Outside, enjoy your own private oasis featuring a covered deck, outdoor kitchen, tranquil water feature, beautifully sitting areas. Horses are permitted. LOW taxes. Conveniently located near major highways, shopping, dining, and miles of hiking and biking trails. Highly regarded school district with top-rated schools and programs. Properties offering this level of quality, flexibility, privacy, and functionality are exceptionally rare. Inlaw suite potential

1 Evergreen Dr, Chester Twp.
$649,000
4 Beds ⋅ 3.1 Baths ⋅ 4033564 MLS
Set on an approximately 38,002 square foot lot (approximately 0.87 acres), this 1950s split-level home offers 4 bedrooms and 3 1/2 baths with a flexible multi-level layout ideal for everyday living and entertaining. The main level features a foyer, living room with fireplace, dining room, and an eat-in kitchen with direct access to the deck for easy indoor-outdoor flow, while the upper level includes a primary bedroom with en-suite bath, three additional bedrooms, and a full hall bath. The ground level provides convenient daily-use spaces including an attached two-car garage, recreation room, laundry area, and additional bath accommodations, and a fully finished basement adds versatile space for media, fitness, hobbies, or storage. Outdoors, the expansive backyard is anchored by a heated in-ground pool, creating a private retreat for summer enjoyment. Additional highlights include central air conditioning, hot water baseboard heat (oil), hardwood flooring (as-is), a sprinkler system, solar system, well water, septic, and flexible possession.

Chester Boro
$1,800,000
4 Beds ⋅ 4.2 Baths ⋅ 4041593 MLS
One-of-a-Kind Hilltop Masterpiece Riverbend Timberframe Post-and-Beam Construction on a 3+ acre hilltop homesite. A remarkable residence that showcases the timeless beauty of timber frame construction, combining architectural character w/modern comfort. The property offers privacy, breathtaking views & an unparalleled setting. A rare opportunity to own a truly distinctive custom home. Vermont casting wood stove in the foyer. The Great Room w/soaring ceiling & stunning granite fireplace. Family room has a Jotul gas stove & adjoins a versatile Den ideal for gym/playroom. The granite kitchen is designed for entertaining w/viking appliances & dual dishwashers. Exquisite dining room for special occasions. A sun-drenched breakfast room that welcomes the morning sunlight. 4 spacious en-suite bedrooms w/guest room 1st flr. Vermont casting gas stove in primary & 2nd flr rooms. His-and-her offices for work from home. A 2nd floor billiard loft overlooks the great room. Resort-style natural pool complete w/cascading waterfalls, hidden grotto & Spa. Finished lower level. Marvin casement windows & glass doors that flood the interior w/natural light & picturesque views. Relax on the front porch & enjoy breathtaking winter sunsets. Hardwood floors & radiant heat thru out, 5 skylights, new roof (2023) w/2 cupola's crowned w/weathervane, whole-house generator & 2 fireplaces. High performance structural insulated panels (SIP) to ensure maximum energy efficiency. Professional landscaped grounds

9 Beacon Hill Dr, Chester Twp.
$499,999
2 Beds ⋅ 1.1 Baths ⋅ 4040693 MLS
Beautiful location in the Heart of Chester Borough, across from the Chester Theatre Group, this location allows a short walk to shopping and dining, and a good locationto major highways. Large property, over half an acre with most of the property open for your recreational use. This has two Large Bedrooms, one Full Bath and one Half Bath, a spacious Dining room and Large Living Room. Some updates may be desired when you make this house your home.

57 Grove St, Chester Boro
$699,000
4 Beds ⋅ 3 Baths ⋅ 4040187 MLS
From the moment you arrive, this beautifully updated home welcomes you with classic charm, comfortable living spaces, and thoughtful modern improvements. A spacious foyer opens to an inviting floor plan featuring a bright living room with a wood-burning fireplace and an adjoining dining room, ideal for everyday living and effortless entertaining. The renovated kitchen is equipped with stainless steel appliances, ample cabinetry, generous prep space, and convenient access to the mudroom. The main level also includes a cozy den, a bedroom, and a full bath, offering flexible space for guests, or home office. Upstairs, you'll find two additional bedrooms, two full baths, and an expansive primary suite complete with an en suite bath, a walk-in cedar closet, and oversized windows that bring in an abundance of natural light. A secondary bedroom also features a spacious walk-in closet for additional storage. Step outside to enjoy the large two-tier deck overlooking a level backyard surrounded by mature trees, creating a private setting for entertaining, outdoor activities, gardening, or quiet evenings at home. Ideally situated close to shopping, dining, parks, grocery stores, and major highways, this exceptional Chester Township home combines character, functionality, and convenience in a highly desirable location.

361 North Rd, Chester Twp.
$799,810
3 Beds ⋅ 3.1 Baths ⋅ 4039867 MLS
Desired Neighborhood of Dogwood Acres in Chester Twp....Cathedral Ceiling Great Room Addition in 2006 with Floor to Roof Stone Wall and Wood Burning Stove...Remodeled Kitchen and Bath in 2006...Private 1.4 acres with Large Trees...

30 Dogwood Dr, Chester Twp.
$699,000
3 Beds ⋅ 2 Baths ⋅ 4039850 MLS
Beautifully updated home situated on over one acre in a desirable cul-de-sac setting which offers privacy and is surrounded by homes of substantially higher value offering not only a wonderful place to live but will prove to be a sound investment. Recent improvements include a newer roof, siding, tilt-in windows for easy cleaning, newer kitchen with granite counter tops, and two full baths featuring radiant heated floors. The oversized detached two garage includes a loft suitable for a studio, workshop, recreation room, home office or additional storage. A newer "four bedroom" septic system provides future expansion potential. The beautifully appointed walk out stone basement also offers tremendous potential for additional living space. Located within the highly rated Chester Township School District and just minutes from shopping, dining, recreation and major arteries for easy commuting. Move in ready and in a sought after location!

16 Chester Place, Chester Twp.
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