Back to Search
Est. $2,257/mo
4 Beds3 Baths2,646 Sqft

4 Reputation Drive, Chester Town, NY, 10918

Listed by Agnes Burch
2646 SqFt House In Chester Town

Colonial home at Bilevel price! This home gives you 2654sf of living space plus an additional 800sf finished basement that sits on a private 2-acre lot. Once you enter the private road you will feel the stress of the day just wash away and a calming effect take over. Home offers large entryway, living room, dining room, eat-in-kitchen, office, family room, enclosed porch that opens to a 14x36 deck overlooking private backyard. Master bedroom with walk-in-closet and recently renovated master bath and three more bedrooms. Walk-out finished basement. There is also plenty of storage in the home. This home is tucked away yet conveniently located for commuting to NYC, Westchester and New Jersey. In addition to garage parking there is room in front that will fit another 4-5 cars. Roof, above-ground oil tank, water filtration system, furnace all replaced in last 10 years.

See Less
Interested in this home?
Request a Video Tour
Local Experts
Samantha Wilson
Buying a home is a big decision
You don't have to do it alone.
Schedule a Tour
4 Reputation Drive
Request a Tour
Compare Similar Homes
Currently Viewing This Home
4 Bedrooms
3 Bathrooms
2646 Sqft
2 Acre(s)
Built 1986
4 Bedrooms
4 Bathrooms
2853 Sqft
0.84 Acre(s)
Built 1997
4 Bedrooms
3 Bathrooms
2602 Sqft
0.92 Acre(s)
Built 1946
4 Bedrooms
3 Bathrooms
2656 Sqft
4.5 Acre(s)
Built 2001
Contact one of our agents for a more detailed home comparison!
Contact Agent
Listing provided by
Agnes BurchListing Agent
Continue Your Search
$474,000Est. Payment
3 Beds | 2 Baths | 2,488 Sqft

20 High Street, Chester Town, NY 10918

House For Sale

This house, cottage and 3 car garage were built in 1825 but you will see that meticulous care has been taken of all of them. 1 bedroom/1 bathroom on-site cottage will pay your yearly taxes for you. Have a cup of coffee on your deck or plant some flowers in your attached greenhouse. Located in the heart of Chester this lot provides plenty of privacy. Long driveway leads to 3 car garage or park up to 5 cars next to the house for easy grocery drop off. List of upgrades MAIN HOUSE: heating system 2000, roof & electric 2002, upstairs windows, siding & upstairs bathroom 2005, porch windows & front rock face 2007, chimney/basement floor/repoint foundation wall & front entrance 2009, front storm door 2010, stove & refrigerator 2015, water heater 2018. COTTAGE: Roof 2004, Siding 2005, water heater 2018. If qualified you will receive $781 back for the STAR Rebate yearly. Breakdown of taxes: County/Town $2,653 Village $2,449 School $6,841. Don't miss this beautiful home

$460,000Est. Payment
4 Beds | 4 Baths | 2,853 Sqft

16 Chester Acres Boulevard, Chester Town, NY 10918

House For Sale

Expanded Colonial on cul-de-sac with 4 to 6 bedrooms. The best of both worlds: convenient commuter location with the potential for a quiet, home office set up! First floor offers a formal dining room, living room, and open-concept area with a kitchen, flexible seating areas and stone gas fireplace. A door off the open-concept living area leads to a private hallway separating the first-floor guest wing from the main house. Guest wing includes a spacious bedroom with walk-in closet and en-suite bath, a den/office with closet and French-door entrance to the back deck. Second floor holds the Master Suite, two additional bedrooms, another full bath and a 160-sq. ft. bonus room! The light-filled bonus room with dormer windows and two closets has the potential to make a fabulous home-school/study room, studio, playroom, exercise room, bedroom or home office. Full, unfinished basement houses laundry area and tons of storage. Paved driveway with plenty of parking and two-car garage. Generous, fully-fenced back yard is set-up and pool-ready - the choice is yours!

Open 8/16
$399,000Est. Payment
3 Beds | 3 Baths | 2,056 Sqft

101 Sunfish Lane, Chester Town, NY 10950

House For Sale

Looking to make that move, look no further. Award Winning MONROE WOODBURY SCHOOL DISTRICT. This home features 3-4 generously sized bedrooms, 3 Full Bath, Central Air. Upgrades to include New Roof (2020), Deck (2020) , Kid Play set/flooring (2020) New Concrete Septic Tank (2020), New Well pump (2020), New water softener (2020) Great Commuter location close to Buses, Trains, NYS Thruway. Motivated Seller

$415,000Est. Payment
3 Beds | 3 Baths | 1,888 Sqft

15 Grant Drive, Chester Town, NY 10950

House For Sale

This home has it all for the one that enjoys entertaining. Come be impressed when you enter the front door with large open feeling with cathedral ceilings in the living room and dining rooms. Short walk down the hall to 3 bedrooms all are nice size and the master with its own bath. Go downstairs and find the nicely finished family room with another full bath and laundry room. From the kitchn door you step on to a deck that has an amazing view of the large in ground pool completely surrounded by an enormous patio. At the end is a large shed with awning that covers a large bar with a granite slab for the top! It's all here for you and your friends to enjoy, schedule a showing today!

$465,000Est. Payment
3 Beds | 3 Baths | 2,500 Sqft

25 Lori Lane, Chester Town, NY 10918

House For Sale

This home is located at 25 Lori Lane Chester Town, NY 10918 US and has been listed on Homes.com since 10 August 2020 and is currently priced at $465,000, approximately $186 per square foot. This property was built in 2020. 25 Lori Lane is within the school district(s) Monroe-woodbury Central School District and Chester Union Free School District with nearby schools including North Main Street School, Chester Middle-high School, and Monroe Woodbury High School. Similar properties nearby are <a href="/property/1745-kings-hwy-chester-ny-10918/id-400020897334/">1745 Kings Hwy</a>, <a href="/property/425-stage-rd-monroe-ny-10950/id-400020914722/">425 Stage Rd</a>, <a href="/property/385-lake-shore-dr-monroe-ny-10950/id-400020890063/">385 Lake Shore Dr</a>, <a href="/property/monroe-ny-10950/id-400020918065/">52 Catskill Ave</a>, <a href="/property/92-edward-pl-monroe-ny-10950/id-400020919067/">92 Edward Pl</a>, <a href="/property/30-hawthorne-dr-monroe-ny-10950/id-400020890247/">30 Hawthorne Dr</a>, <a href="/property/16-old-town-rd-monroe-ny-10950/id-400020890241/">16 Old Town Rd</a>, <a href="/property/25-lori-ln-chester-ny-10918/id-1000038213520/">25 Lori Ln</a>, <a href="/property/chester-ny-10918/id-400032535154/">3561 State Route 94</a>, and <a href="/property/2-fields-ln-chester-ny-10918/id-400020896087/">2 Fields Ln</a>.

$339,000Est. Payment
4 Beds | 2 Baths | 1,846 Sqft

3 Chester Acres Boulevard, Chester Town, NY 10918

House For Sale

A home OF LUXURY, renovated with the latest amenities. Improved & constructed to fit your taste & budget. Enjoy a spacious living room, 4 bedrooms, new upgraded kitchen, quartz countertops, including an island, high-end appliances, new hardwood floors as seen, new central ac system, installed designed lighting all around for your comfort, modernized bathrooms with magnificent tiles. SO now come & browse...around IN your dream house... Created SO fashionable!!

$299,900Est. Payment
4 Beds | 2 Baths | 1,734 Sqft

1490 St Hwy 17m, Chester Town, NY 10918

House For Sale

Beautiful capecod located in Chester on a nicely landscaped lot with a huge wrap around deck! Features for this gorgeous home include 4 bedrooms, hardwood floors through out, formal dining room with sliders leading out to deck, cozy living room and family room with wood burning fireplace. The nicely appointed kitchen offers a cook top, wall oven and lots of cabinets for storage! Entertain in the fenced in back yard or just relax on the deck. This well kept home is a must see and is close to shops, parks and major highways making for a great commuter location. 2 car garage and full, unfinished walk out basement also included.

$325,000Est. Payment
3 Beds | 2 Baths | 1,860 Sqft

5 Tyler Place, Chester Town, NY 10950

House For Sale

Well Maintained Raised Ranch in Lakehill Farms Neighborhood!! First Level Features Open Concept Living Room and Formal Dining Room! Updated Kitchen and Floors (2017)! All Three Bedrooms are Spacious! Two Closets in Master Bedroom! Updated Full Bathroom with Skylight (2018)! Full Finished Lower Level with Updated Half Bathroom (2018)! Private Laundry with new Hot Water Tank (2019)! Two Car Garage! Enjoy Overlooking the Huge Backyard From the Deck! Home Sits On Over Half An Acre and Backs Into A Pond That Is Used For Kayaking and Ice-Skating! Ready to Move In! Make This Your Dream Home! Perfect Commuter Location! Low Taxes! Award Winning Monroe School District!

$389,999Est. Payment
4 Beds | 2 Baths | 1,950 Sqft

189 Greycourt Road, Chester Town, NY 10918

House For Sale

Country living at it's finest. Lushly treelined - ACRE 3 LOTS- adjoining farm land. Beautiful private picturesque mountain view setting. Situated is a 1920 s well-built 1,950 sf original Colonial farmhouse. This lovely home consists of 4 BRs / 2 baths, presenting an inviting warm & cozy feel, loaded with charm & character. Amazing wood work with hardwood floors and magnificent millwork throughout. Convenient location, minutes to highway, park/ride to NYC, shopping, restaurants and part of Monroe/Woodbury Schools. Spacious & level grounds for recreation & entertaining. Walk to the Heritage Trail. Another bonus feature, oversized lot possesses a separate Outbuilding, 600 sf., perfect for a multi vehicle garage or workshop. Home features: Kitchen w/ stainless appliances, Formal DR, LR w/ stone fireplace, Laundry and Family Rm leading out to nice deck overlooking a spectacular view and rolling acres. Plenty of storage. Lower level opens at ground level, includes attached garage.

$443,000Est. Payment
4 Beds | 3 Baths | 2,108 Sqft

18 June Road, Chester Town, NY 10918

House For Sale

Beautiful Chester Colonial in Highly Desired Neighborhood that is only 60 minutes from NYC! Tri-Level Home! 2908 Square Feet Total which includes 800 Square Feet in Full Walk Out Basement with High Ceilings! First level consists of gleaming hardwood floors, powder room, living room, formal dining room, two car garage, mud room, living room with vaulted ceilings and wood-burning fireplace, gorgeous kitchen with granite counter-tops, tiled back splash, stainless steel appliances, two tone cabinetry and island seating! Second level consists of four large bedrooms and two full bathrooms! There is a spacious master bedroom with bathroom and Jacuzzi tub, vaulted ceilings, palladium window, ceiling fan and walk in closet! Lower level has a huge full walk out basement! Use this space for a movie room, gym, office, playroom, in-law suite, wine cellar! Another feature that makes this home so unique is the hiking trail located right in your backyard! Enjoy the private backyard oasis that includes a deck and hot tub! Energy efficient home with new solar panels! Low energy bill and low taxes! Blacktop driveway sealed 2020! Deck freshly painted 2020! Virtual Tour https://youtu.be/Ze5DONh7XXA

$459,900Est. Payment
4 Beds | 3 Baths | 2,656 Sqft

95 Hambletonian Avenue, Chester Town, NY 10918

House For Sale

Look No Further! If space and privacy is what you are looking for this beautiful property is for you! Situated on a large easily maintained 4.5 acre lot, this colonial has it all. The grand entrance to this home boasts beautiful hardwoods and vaulted ceilings. This is just the beginning! A very large formal dining room and expansive tiled kitchen provides room for everyone and makes entertaining easy. The family room has a fireplace for those cold winter nights and plenty of room for relaxing. Four large bedrooms, including and tremendous master suite and master bath with Jacuzzi tub, means there is plenty of room for all. A partially finished basement has finished office space and room for a potential 5th bedroom. This house sits hidden and private but is close to school, all amenities and transportation. It surely is a peaceful and serene location with both yard and wooded areas making up the property. Come see your new home and have the best of everything, close to everything!

$329,900Est. Payment
3 Beds | 3 Baths | 2,210 Sqft

68 Pewter Circle, Chester Town, NY 10918

House For Sale

* MINT * Upscale End Unit attached single family home w/2 Car Gar Townhouse in Sugarloaf(Chester) w/WARWICK Schools is like a model home that Backs to the Woods for Privacy * Granite Kitchen: stainless steel appliances, custom pendant lighting, hardwood floors the whole house- no carpets at all * Convenient laundry upstairs * HUGE Master Suite w/sitting area & lots of windows for natural light overlooking the park-like property * Master spa bath has jacuzzi tub, separate shower & double sinks * WIC's * Spacious family room has beautiful gas fireplace * Lightly lived in - this home is like new * C/Air & recessed lighting * Formal dining room w/sliding doors to your large trex deck w/No-one behind you, just the woods & mountain views as you Barbeque on your large trex deck * Extremely easy commuter location 2 miles to highway & 6 miles to Village of Warwick * This home has been Well-Loved by its Owners & it shows throughout * HOA covers snow & lawn maintenance *

$409,900Est. Payment
4 Beds | 3 Baths | 3,081 Sqft

11 Kennedy Lane, Chester Town, NY 10950

House For Sale

* Gorgeous Renovated Farm House with Rich History - Once a Winery * This Spacious 4 Bedroom is right out of Architectural Digest - With Over 3081 Sq. Ft. All the Rooms are Oversized * The Open Living Room has Space for Adult Entertaining as well as Space for the Kiddos * Open Dining Room can fit the Whole Family at Holiday Time w/Stunning Views * Chef's Kitchen is Totally Updated w/Glass Cabinets, Open Shelving, Breakfast Bar, Gas Stove, St St Appliances, Farm House Sink & Faucet, Pine Floors, Granite Counters & 3 Panel French Doors leading to the Large Deck * Family Room offers Stone Fireplace w/Custom Shelving & Windows, a Great Place to Gather for Movie Night * 1st Floor-Laundry Room has Charming Stained Glass Windows * Master Bedroom features: Vaulted Ceilings, Tons of Light Streaming in from All the Unique Windows, Master Crafted Woodwork, Views for Miles of the Appalachian Mountains and Master Spa Bath w/Double Sinks * Guest Rooms are all Perfectly Sized, with 4th Bedroom W/ Wall to Ceiling Windows overlooking a Huge Magnolia Tree * Walk Up Attic has Tons of Storage Space * This is a Very Special Property you wont want to miss * MW Schools - Sapphire & Pine Tree Elementary * Easy Commuter Location, near Train & Bus to NYC *

$499,900Est. Payment
4 Beds | 3 Baths | 3,122 Sqft

138 Conklingtown Road, Chester Town, NY 10918

House For Sale

Beautiful colonial with private setting and views of Sugar Loaf Mountain. The inviting front porch will lead you into a large foyer with formal dining room, family room with fireplace, eat in kitchen, and playroom/formal living room. The back deck overlooks the inground salt water pool. A freshly painted upstairs you will find a large master suite with balcony and master bath, three more bedrooms and a full bathroom. This home is minutes from the highway making an easy commute.

$499,000Est. Payment
4 Beds | 3 Baths | 3,640 Sqft

2 Hillview Terrace, Chester Town, NY 10918

House For Sale

Seldom will a single owner home of such stature set beautifully on a parcel of nearly 2 acres with sweeping mountain views providing privacy without isolation become available. This spacious, sun filled colonial has been meticulously maintained with 4 bedrooms, 2.5 baths, finished basement, 2 car garage, extended driveway, backyard with a newly refinished built in concrete heated pool, an entertainment sized surround and deck allows the owners a lifestyle more in line with a pristine resort then the family home. Hardwood floors, Anderson Windows, central air, granite kitchen, stainless appliances, ample storage and only minutes to all major roadways, NYC bus and rail transportation, shopping, and the Warwick schools. 2 Hill View Terrace, Chester, NY, truly a home for a most discerning buyer providing an opportunity for a lifestyle where memories will be treasured.

How To Finance

As a homebuyer, there are quite a few financing options to consider. Our interactive guide can help find which is right for you, and guide you through the paperwork.

Get Started

Ask about this home

Request Info
Call to ask about this home today!(844) 505-4874
By pressing “Request Info” to submit my info, I agree Homes.com (HDC) and real estate professionals may call/text me about my inquiry, which may involve automated means. Message & data rates may apply. I agree HDC may share any info I submit and info of my activity on their site with this properties listing agent, and other 3rd parties, such as HDC’s lead customers. I understand I don’t need to consent as a condition of any purchase and can revoke my consent at any time. I agree to theTerms of Use and Privacy Policy.
version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >