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

$949,000
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.

9 Francis Ln, Chester Twp.
$939,000
4 Beds ⋅ 2.1 Baths ⋅ 4038814 MLS
Welcome to 2 Chester Woods Drive. Situated on just over 3 acres, this spacious home has over 3,200 sq ft of finished living space with 4 bedrooms and 2.1 bathrooms with hardwood floors and tile throughout. The first floor features a large eat-in kitchen, living room with a fireplace, a formal dining room, and a family room. The second floor has 4 bedrooms and 2 full bathrooms. The 5th room on the second floor can be used as an office or flex room. The partially finished basement has over 1,200 sq ft of space with plenty of storage. Outside, you will find an expansive fenced-in yard, a freshly painted deck, a beautiful in-ground pool, and a hot tub. This home is conveniently located just minutes away from the Chester Township school district and historical downtown filled with quaint restaurants, shopping, and entertainment.

2 Chester Woods Dr, Chester Twp.
$649,000
4 Beds ⋅ 2 Baths ⋅ 4038657 MLS
Set within one of Chester Township's most desirable neighborhoods, this beautifully maintained 4-bedroom, 2-bath bi-level combines timeless appeal with everyday functionality. Filled with natural light, the main level is designed for both everyday living and effortless entertaining. The living room, highlighted by a large bay window, flows seamlessly into the dining area and well-appointed kitchen featuring stainless steel appliances, a skylight, and sliding doors leading to a spacious deck overlooking the backyard. Three generously sized bedrooms and a full bath complete the main level. Downstairs, you'll find a welcoming family room featuring a cozy wood-burning stove + direct access to a new covered paver patio. The lower level also offers a fourth bedroom, a full bath with oversized stall shower & a convenient mudroom/laundry room. Hardwood floors, crown & picture frame molding add warmth and classic character throughout. Outside, the tranquil backyard has been enhanced with new vinyl and wood fencing, solar lighting, a new storage shed, and fresh landscaping, creating an inviting setting for quiet evenings or weekend get-togethers. A one-car garage and ground floor crawl space provides valuable additional storage. Freshly painted kitchen and bathrooms add to the home's move-in-ready appeal. Ideally located near top-rated schools, parks, shopping, dining, and major commuter routes, this home combines a peaceful setting with exceptional everyday convenience.

19 Selma Blvd, Chester Twp.
$650,000
4 Beds ⋅ 1.1 Baths ⋅ 4035425 MLS
This charming original-owner center hall colonial is perfectly situated on a quiet cul-de-sac in desirable Chester Township, known for its scenic character, vibrant town, and highly regarded schools, including the Chester School District and the IB program at Mendham High School. The home offers four bedrooms and one-and-a-half baths, with a classic layout that presents a wonderful opportunity to make it your own. The eat-in kitchen flows directly into the family room, creating a comfortable everyday living space, while the family room is anchored by a cozy wood-burning fireplace. Formal living and dining rooms provide additional space for gatherings and entertaining. Hardwood floors lie beneath the carpeting throughout most of the home, offering the potential to restore their original warmth and character, with the exception of the family room. Additional features include gorgeous wood ceiling beams, attached garage, a pull-down attic for storage, and a full basement with laundry and ample storage, work, and recreation space. The flat, usable yard adds to the home's appeal and offers plenty of room for outdoor enjoyment. Set on a lovely street in a sought-after location, this home presents a rare opportunity to bring your vision and updates to a property with solid bones and enduring appeal. Chimneys, fireplace and flues are as-is with no known defects.

7 Catan Dr, Chester Twp.
$764,900
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
5 Beds ⋅ 4.3 Baths ⋅ 4034404 MLS
Own a piece of history ! A car enthusiasts paradise with a 7-car-garage ! 1880 built sprawling historic ranch where history meets high design ! Once the country retreat of the distinguished Hardin family this architectural masterpiece is anchored by its stunning, original stone wall construction. Today it stands as a breathtaking testament to luxury single-story living, offering an incredible 6737 square feet of entirely updated space. An addition in 2022 added a brand new grand-scale designer kitchen spanning 700+ Sq Ft, a masterclass in culinary luxury and architectural drama. Soaring, extra high ceilings adorned with exquisite custom millwork. Designed for entertaining and seamless meal preparation, featuring dual center islands, dual dishwashers, dual wall-ovens, dual sinks including an extra long prep-sink & more. An adjacent 16 X 12 mud room/laundry is a full scale, premium utility room, with a spiral staircase to the 2nd floor office. The addition also includes a private sanctuary, an ultra luxurious master bedroom focusing on the architectural warmth of the bedroom and the cutting edge, spa-level technology in the bath. The original home offers a Formal L.R. with a F.P. and french doors leading to patios, D.R. with an entire wall dedicated to custom wine storage, Fam Rm complete with F.P. & extensive Mill work open to the Kit. Surrounded by gorgeous property. Guest bedroom suite, jack & jill bedrooms, princess suite, Full Gym above the 4-car-gar, 1-car-gar & Craft Rm.

235 Old Chester Rd, Chester Twp.
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 4032248 MLS
Huge & beautiful single family house situate in 7.6 acres lot, with 5 big beds & 4 full baths, kitchen, living & dining rooms, family room, finished basement, 3 car garage, and of course private backyard oasis with an in-ground pool.

17 Cromwell Dr, 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.
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 4028352 MLS
Tucked at the end of a quiet cul-de-sac on 4.73 private acres, this 4,437 sq ft colonial offers what almost never comes together in Chester Township: land, privacy, and a home that?s completely done. Fully renovated within the last two years, no projects, no waiting on contractors, just move in. The reimagined chef?s kitchen anchors the main level with quartz counters, Café appliances, and an open flow built for entertaining. First floor flex room and full bath, ideal for guests, in-laws, or work-from-home flexibility. Renovated primary and guest baths, custom millwork and shadow-box paneling, recessed lighting, newer interior doors, and fresh paint inside and out complete the turnkey package. Outside, mature trees frame nearly five acres of picturesque land. Award-winning Chester schools, minutes to downtown shops and dining, easy access to Rts 206/24/287 for commuters. Relocation forces the sale, a rare chance at a turnkey home on one of Chester?s most private setting. Come see it before someone else does the math.

31 Warren Cutting, 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.
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