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

$1,300,000
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.
$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
$599,000
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.
$899,000
4 Beds ⋅ 2.1 Baths ⋅ 4038875 MLS
Beautiful updated Colonial on a level 3.3 wooded acre lot at the end of cul-de-sac in Chester Twp. Located on the East side of town with Morristown and Mendham just minutes away. Newly renovated kitchen with open floor plan, granite and ss appliances. Interior features include family room with fieldstone hearth and Jotul wood burning stove, Living room has custom cabinets and built in bar, decorative moldings and built in's, raised panel doors, hard wood flooring throughout, marble foyer, Anderson windows, sliders off eat in kitchen to deck, the property features a professionally landscaped wooded lot with mature trees and sunny southern exposure w raised-bed gardens, Trex deck, pavers, gazebo, and playhouse. Finished basement features an office, exercise room and rec room. This home has an efficient furnace and water heater and Thermador roof mounted stove vent.New Price reflects roof replacement

9 Francis Ln, Chester Twp.
$749,900
4 Beds ⋅ 2 Baths ⋅ 4034718 MLS
Beautifully Renovated Custom Home on 2 Level Acres in Chester Twp! Move right into this beautifully updated 4-bedroom, 2-bathroom custom home located in a highly desirable neighborhood. Enjoy peace of mind with a brand-new roof, septic system, well, and electrical box. Main Level Features: Updated Kitchen: Stunning quartz countertops, stainless steel appliances, and a matching stainless steel sink. Living Spaces: Bright living room offering peaceful views overlooking the spacious backyard. Bedrooms: Two comfortably sized bedrooms and a pristine full bathroom. Upper Level Features: Primary Suite: Main bedroom complete with convenient his-and-hers sinks. A second generously sized bedroom. Lower Level & Exterior: Walkout Basement: Full, unfinished walkout basement hosting the laundry area. Perfect for storage, a workshop, or future finishing. The Lot: Situated on a rare, level 2-acre lot providing endless outdoor possibilities, privacy, and more.

20 Cooper Ln, Chester Twp.
$4,250,000
8 Beds ⋅ 6.3 Baths ⋅ 4030234 MLS
Set on 6 breathtaking acres backing directly to Black River Park w/ private park access, The Herb Farm is a once-in-a-generation country estate where history, romance & luxury exist in perfect harmony. Originally a stone barn dating back to circa 1750, this extraordinary compound has been masterfully transformed into a cinematic retreat evoking the timeless elegance of the European countryside. Beyond the gates, a long winding drive leads through storybook scenery before revealing the stone-clad main residence, privately enveloped by preserved parkland. Main residence features rich architectural character including groin, barrel & vaulted ceilings,mahogany windows, stone walls, & 5 wood-burning fireplaces. A stunning kitchen anchors the home w/ La Cornue stove/oven, Sub-Zero refrigerator, 2 dishwashers & seamless entry to a sunlit stone great-room.The primary suite is a true sanctuary w/ its own foyer, balcony, custom closet & imported marble bath. Magical outdoor living w/ expansive terraces, an indoor-outdoor kitchen w/ an imported pizza oven & Argentine grill & a bocce court overlooking sweeping views. Property is also home to a fully renovated guest cottage & a charming carriage-house suite above the 3 car garage. Updated mechanicals & a full-property generator provide effortless modern comfort. Just 1 hour from NYC, yet feeling worlds away, The Herb Farm is more than a home, it is an extraordinary estate where every season feels cinematic & every detail tells a story.

55 State Park Rd, Chester Twp.
$1,599,900
4 Beds ⋅ 4.1 Baths ⋅ 4029335 MLS
ABSOLUTELY MAGNIFICENT CRAFTSMAN-STYLE CUSTOM HOME INSPIRED BY THE GRAND ESTATES OF THE LATE 19TH CENTURY AND THE DESIGN TRADITION OF ARCHITECT ROBERT A.M. STERN. DRAMATIC GABLES, OVERSIZED WINDOWS, CEDAR SHINGLE SIDING AND NEW CEDAR FRONT PORCH CREATE THIS STUNNING EXTERIOR. A FULL ROOM-TO-ROOM RENOVATION IN 2015 PRESENTS THE HOME IN LIKE-NEW CONDITION. OFFERING 12 ROOMS, THE LAYOUT INCLUDES 4 BEDROOMS, 4 FULL BATHS AND 1 POWDER ROOM. ENJOY A SPACIOUS FAMILY ROOM PLUS A LIVING ROOM THAT CAN ALSO SERVE AS A DEN. A FLEXIBLE ADDITIONAL ROOM NEAR A FULL BATH IS IDEAL FOR A HOME OFFICE, GUEST SUITE. THE HAND BUILT DESIGNER KITCHEN FEATURES A FIREPLACE AND OVER 250 SQ FT OF GRANITE COUNTERTOPS, CUSTOM BUILT CABINETRY A BUTLER'S PANTRY, AND SEAMLESS FLOW TO A STUNNING DINING ROOM. HARDWOOD FLOORS THROUGHOUT; RADIANT HEAT ON THE SECOND FLOOR. THE PRIMARY SUITE IS A SHOWSTOPPER WITH A PRIVATE FRONT BALCONY AND SITTING AREA. CUSTOM BUILT-INS AND EXQUISITE TRIM AND MOLDINGS ARE FOUND THROUGHOUT. NEARLY 5,000 SQ FT SPANS TWO LEVELS, PLUS A 1,400 SQ FT LOFT AREA READY TO BE FINISHED. ADDITIONAL HIGHLIGHTS INCLUDE CUSTOM BUILT CEDAR FRONT UPPER LEVEL DECK AND LOWER PATIO AREA, A BRAND NEW DRIVEWAY LEADS TO OVERSIZED 4-CAR GARAGE, EXPANSIVE REAR PATIO AND OUTDOOR KITCHEN SET ON A PRIVATE 3.25-ACRE PROPERTY WITH PLENTY OF ROOM FOR A POOL.

3 Laurel Ln, Chester Twp.
$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.
$1,399,000
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. Fireplaces being conveyed "as is" with no known defects.

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.
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