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Homes for Sale with a Pool in Chester, NJ

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Welcome to your dedicated resource for homes for sale with a pool in Chester, NJ. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chester, NJ agent, The Courtney Orlando Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Chester, NJ

$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.
$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.
$1,999,000
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.
$999,000
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.
$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.
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