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$450,000
2 Beds ⋅ 3 Baths ⋅ 1008921 MLS
Welcome to this beautifully sun-filled townhouse located on a cul-de-sac in the desirable Town of Woodbury, Highland Mills, NY. Nestled in a highly sought-after neighborhood, this spacious home offers two primary suites, each featuring walk-in closets and private primary baths. The open floor plan features a bright living room, formal dining area, and convenient half bath. The kitchen offers an open-concept design with a breakfast nook, hardwood floors, 42-inch cabinets, and balcony molding. Step out onto the sun-filled balcony and enjoy your morning coffee, family barbecues, or simply relax while taking in the peaceful scenery, mature trees, and birds chirping. The living and dining areas offer beautiful mountain views throughout all seasons. Brand-new flooring was installed throughout the main and second levels in 2025, along with a new storm door. Upstairs, you will find a versatile office nook that can also be used as a library, reading area, or flex space. Abundant closet space is found throughout the home. Additional features include attic floorboards for extra storage, a freshly painted garage with private storage space (2026), basement utility sink next to the laundry area, central air, natural gas, HVAC system installed in 2023, hot water heater installed in 2023, and front steps completed in 2022. Enjoy low HOA fees of just $170 per month and maintenance-free living. Residents of Highland Mills have access to Earl Reservoir and John Burke Pool, offering swimming, boating, fishing, dog parks, ball fields, summer camps, and pavilions, all within the highly rated Woodbury School District. Ideal commuter location with express bus service to NYC located at the entrance of Timber Trail and easy access to I-87, Route 17, Route 32, and Route 6. Conveniently located near Stewart International Airport, Woodbury Common Premium Outlets, West Point, Bear Mountain, and more. Nearby shopping includes Walmart, Target, Home Depot, BJ’s, TJ Maxx, and a variety of dining options featuring Italian, Spanish, and many other cuisines. New 2025 formal dining and living room set negotiable with sale. Select items may also be available for sale.

10 Rockridge Drive, Highland Mills
$375,000
1007206 MLS
Discover the perfect opportunity to build your dream home on this spacious 1.2-acre parcel of land located at 188 Roselawn Rd in the desirable community of Highland Mills. Tucked away in a peaceful setting, this property offers the ideal blend of privacy and convenience. Situated between County Route 105 & Woodbury Junction, you’ll have easy access to main roads while still enjoying the tranquility of a residential neighborhood. The generous lot size provides ample space for a variety of home designs, outdoor amenities, and lush landscaping. Surrounded by natural beauty, this land is perfect for those who appreciate a serene environment with the potential for gardens, play areas, or entertaining spaces. Whether you’re looking to build a custom residence or invest in land in a sought-after area, 188 Roselawn Rd is a rare find. Don’t miss out on this exceptional opportunity to create your own haven in Highland Mills!

188 Roselawn Road, Highland Mills
$824,000
5 Beds ⋅ 3 Baths ⋅ 1004118 MLS
On Zillow the virtual 3D tour you can find it by facts and features, 8 Allaway Crescent - 4,231 SQ FT + Full Unfinished Basement 4,231 SQ FT + Full Unfinished Basement | 5 Bedrooms Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath | Mountain Views, Welcome to 8 Alloway Crescent. This 4,231 square foot home offers functional layout and impressive scale, plus a full unfinished basement ready for your vision. Main Level You enter through a big, wide foyer with hardwood flooring extending throughout the main level. Dining Room: To the right of the foyer is a big dining room with ample space for entertaining. Living Room: To the left of the foyer is a nice, big living room, well suited for formal seating or quiet conversation. Family Room: The beautiful big family room is open to the kitchen and open to the dinette area, accommodating large furniture arrangements and everyday living. Dinette: Adjacent to the kitchen, there is beautiful space for a dinette with room to put a table. This area has a walkout to the deck and access to the beautiful views. Kitchen: The big kitchen features a large center island, marble countertops, two sinks, abundant cabinetry, and stainless steel appliances. The layout flows directly into the family room and dinette for ease of daily use and hosting. Main Floor Bedroom & Full Bath: The main level includes a den or bedroom plus a full bathroom. This provides flexibility for guests, a home office, or multi-generational living. Garage & Views: A two-car garage is accessed from the main level. Beautiful scenery and views are visible from multiple rooms. Second Level Primary Suite: The master bedroom features a cathedral ceiling and beautiful mountain views. The en-suite bathroom includes a combined soaking tub with jetted jacuzzi, dual vanities, and a stall shower. A walk-in closet is included. The second bedroom is connected to the master with open doors. This layout works well as a baby room, office, or additional bedroom. The third bedroom is a nice size bedroom with closet space. The fourth bedroom is a nice size bedroom with closet space. Fifth Bedroom / Bonus Room: functions as a bonus room and provides additional flexibility for use as a bedroom, playroom, or media room. Laundry is located upstairs for convenience, near the bedrooms. Hall Bathroom: A full hall bathroom serves the additional bedrooms. Additional Levels Walk-Up Attic: A finished walk-up attic is accessed from the second floor and includes a window. The space is suitable for storage, studio, or playroom use. The home includes a full unfinished basement ready for future build-out. Key Specifications: 4,231 Sq Ft Above Grade | Full Unfinished Basement | 6 Total Bedrooms, 5 Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath |2-Car Garage | Cathedral Ceiling in Primary | Walk-Up Attic with Window | Mountain Views

8 Alloway Crescent, Highland Mills
$649,000
3 Beds ⋅ 3 Baths ⋅ 995300 MLS
Nestled on beautifully maintained grounds in a peaceful countryside setting, this charming home offers warmth, comfort, and timeless character. Situated on .59 of an acre, the property features inviting outdoor space perfect for relaxing or entertaining while enjoying the fresh country air. Inside a cozy fireplace creates the perfect ambiance, complemented by a warm and welcoming kitchen and thoughtfully designed living spaces. The home also features an updated well water system. A truly special home blending charm, comfort, and serene surroundings.

289 Seven Springs Mountain Road, Monroe
$675,000
4 Beds ⋅ 3 Baths ⋅ 1004321 MLS
Experience the perfect blend of modern elegance and suburban tranquility in this beautiful Colonial, perfectly positioned on 1.2 acres of manicured grounds. Inside, rich hardwood floors and walls of windows create an airy, light-filled atmosphere. The heart of the home is the efficiently designed kitchen, boasting a breakfast bar, pantry and stainless-steel appliances. It flows seamlessly into both a large family room and a spacious composite deck overlooking your private backyard—ideal for summer BBQs. For formal gatherings, the sophisticated living and dining rooms with crown molding and wainscotting provide a serene backdrop for entertaining. Upstairs, the primary suite serves as a peaceful retreat, complete with a walk-in closet and a double-sink vanity. The additional bedrooms are generously scaled for sleep, study, or play. These bedrooms share a hall bathroom with marble countertops. As an exclusive bonus, residents enjoy premium access to the Woodbury Pool and The Earl Reservoir. Minutes from shopping, schools, and commuter transit.

33 Sutherland Drive, Highland Mills
$865,000
4 Beds ⋅ 4 Baths ⋅ 997814 MLS
Welcome to this beautifully maintained Colonial located in the highly desirable Brigadoon neighborhood, perfectly situated on a quiet cul-de-sac and set on 1.9 private acres. This spacious and move-in-ready home offers 4 bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. The main level features a stunning great room, formal living room, cozy family room, private office, and an expansive eat-in kitchen complete with granite countertops, cherry wood cabinets and flooring, stainless steel appliances, center island, and a convenient butler’s service area. Step outside to your own backyard retreat featuring two decks and a beautiful paver patio — perfect for entertaining or enjoying peaceful outdoor living. Additional highlights include crown molding throughout, a newly renovated finished basement ideal for gatherings or recreation, security system, sprinkler system, two-car garage, and ample street parking. Combining space, comfort, and an unbeatable location, this exceptional home is truly a must-see.

3 Braemar Way, Highland Mills
$900,000
4 Beds ⋅ 3 Baths ⋅ 1002536 MLS
Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and excellent flow into the warm and welcoming family room with fireplace — ideal for both entertaining and everyday living. Formal living and dining areas provide additional space for gatherings and special occasions. The second level offers a large primary suite with vaulted ceilings, walk-in closet, and spa-style bath, along with spacious additional bedrooms and ample storage throughout the home. Step outside and enjoy the beauty and privacy of the expansive property surrounded by mature trees and peaceful natural scenery. Whether relaxing on the front porch, entertaining on the deck, or simply enjoying the open outdoor space, this property offers a true retreat-like setting. A rare opportunity to own a move-in-ready Colonial offering privacy, charm, and exceptional living space.

60 Whitetail Run, Chester
$699,000
1001274 MLS
Discover the perfect canvas for your dream home with this exceptional 1-acre lot, nestled directly behind the highly sought-after and fully established community of Woodbury Junction. This rare offering provides a unique blend of privacy and accessibility, making it an ideal setting. With approved permits already in place, you can begin building your custom home without delay. Surrounded by mature trees and natural landscape, the lot offers a serene and secluded atmosphere, ensuring peace and tranquility while being just steps away from modern conveniences. Enjoy effortless access to the renowned Woodbury Commons Premium Outlets, offering world-class shopping and dining options right at your doorstep. The property is also conveniently located near major highways, local parks, and an array of everyday amenities, making daily living both comfortable and convenient. Whether you envision a spacious retreat or a contemporary residence that embraces the natural beauty of its surroundings, this property delivers endless possibilities. Experience the best of both worlds—seclusion and connection—all in one desirable location.

14 Julien Court, Monroe
$599,000
4 Beds ⋅ 3 Baths ⋅ 997183 MLS
Beyond a long 150-foot driveway, tucked quietly behind mature landscaping and surrounded by the natural beauty of Tuxedo Park, 80 Clinton Road offers the kind of privacy and tranquility that has become increasingly rare. From the moment you arrive, the property evokes a sense of calm and understated elegance, where nature, architecture, and comfort exist in perfect harmony. This impeccably maintained split-level residence features 4 bedrooms, 2 full bathrooms, and 1 half bath, with sunlit interiors, expansive windows, and thoughtfully designed living spaces that feel both refined and welcoming. The home offers a gracious living room, inviting family room, 2 wood-burning fireplaces, and a dedicated laundry room with a slop sink, adding everyday comfort and practicality. Throughout the home, soft natural light and peaceful views create an atmosphere that changes beautifully with every season. The solarium serves as the soul of the residence, a serene year-round retreat where mornings begin slowly with coffee and sunlight filtering through the glass, and evenings are spent immersed in the quiet beauty of the surrounding landscape. Every detail of the home has been curated to encourage a lifestyle centered around privacy, comfort, and effortless living, equally suited for intimate gatherings or quiet moments away from the pace of everyday life. Surrounded by winding roads, preserved landscapes, golf courses, and equestrian estates, 80 Clinton Road captures the timeless appeal of Hudson Valley living while remaining within convenient reach of Manhattan. Properties offering this level of seclusion, character, and setting in Tuxedo Park are seldom available. Schedule your private showing and experience the quiet sophistication and enduring charm of this exceptional residence firsthand.

80 Clinton Road, Tuxedo Park
$894,000
3 Beds ⋅ 4 Baths ⋅ 000137 MLS
220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern touch. Full basement provides excellent storage space. Additional features include Central AC, original Andersen custom windows, and an attached 2-car garage. Step outside to a massive deck, spacious shed, and gorgeous landscaping set on a nice-sized lot. Conveniently located close to all amenities, this property offers privacy, space, and everything you could want in a home and more!

220 Oxford Road, Chester
$999,999
5 Beds ⋅ 3 Baths ⋅ 999261 MLS
A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5 bedrooms and 3.5 full baths. Luxury begins at the illuminated pillars lining the paver driveway, leading to a stone-accented front entry. Inside, sun-filled interiors highlight quality craftsmanship throughout. The two-story foyer features tray ceilings and expansive windows, while recessed lighting, built-in surround sound, and pre-wiring for a security system add comfort and functionality. The chef’s kitchen is a true centerpiece, featuring floor-to-ceiling custom cabinetry, granite countertops, a large center island with seating, and a premium Sub-Zero stainless-steel refrigerator. Adjacent casual dinette provides effortless flow for hosting, with sliding doors opening to the outdoor living areas which provide direct access to a deck & patio area. The oversized family room becomes the center of the home surrounded by windows and comforted by the fireplace. Upstairs, the primary suite offers a private retreat with two custom walk-in closets, a sitting area, and alcove. The en-suite bath features dual vanities, a walk-in shower with multiple shower heads, and a jetted soaking tub overlooking serene sunset views. Three additional bedrooms and one full bathroom are generously sized and thoughtfully arranged on the same level. Outdoors, the property delivers a resort-style experience, expansive open grounds framed by mature landscaping and stunning sunset views. The setting offers exceptional privacy and room to relax, entertain, or expand. Additional highlights include a three-car garage and a setting that perfectly balances tranquility with accessibility. This is a rare opportunity to enjoy luxury suburban living—where space, serenity, and elegance meet effortless access to New York City.

2 Garnett Hill Road, Chester
$1,980,000
5 Beds ⋅ 7 Baths ⋅ 994262 MLS
A HUDSON VALLEY MINI ESTATE WITH 7,500+ SQFT | BACKING ONTO PROTECTED LAND AND FALKIRK GOLF COURSE | 50 MIN TO MANHATTAN === WHAT SETS THIS HOME APART — THE LARGEST HOME IN THE GREENS OF WOODBURY: 5,312 sqft above grade plus 2,200 sqft fully finished lower level. Only home in the community at this scale. — A PERMANENT VIEW: 0.76-acre lot backs onto Town of Woodbury preserve land and Falkirk golf course. No new construction possible behind the property. — 50 MIN TO MANHATTAN: 9 min to Harriman train (NJ Transit to Penn Station in ~1 hour). 50 min via I-87 to GWB. Commutable daily or hybrid. — YEARS OF RELENTLESS INVESTMENT: 2003 shell is original. Most of what defines the home today—iron-and-glass doors, chandeliers, hardwoods, the 2,200 sqft lower level, entire backyard—is the owner's work. — NO HOA: Unusual at this caliber. True ownership, no recurring fees. === WHAT THE OWNER HAS BUILT The 2003 shell was built by The Greens of Woodbury's original developer. Almost everything visible today reflects the current owner's continuous investment. Inside: hand-forged iron-and-glass entry doors with smart fingerprint access. Three new chandeliers, anchored by the signature five-tier jade-based crystal piece. New solid hardwood throughout second floor. Motorized window treatments. 2,200 sqft finished lower level with new AC—wood flooring, bar area, billiards and ping pong, sauna with en-suite bath, au pair suite with en-suite bath, multi-person whirlpool. Outside: 792 sqft heated pool with waterfall (2020). Extensive stone paver patio at entertaining scale. Three distinct outdoor entertaining zones: banquet-scale grilling station in the main yard, covered pavilion on its own balcony, propane fire pit lounge on a separate balcony. Multi-level planted terraces with retaining walls and integrated automated lighting. Ornamental iron fenced rear yard. Whole-house solar (2024). Every visible system reflects 2020s standards. The next owner inherits a finished asset, not a project. === THE HOME 5 bedrooms. Six full and one half baths. Three fireplaces. Solid hardwood throughout all three levels. Circular stone paver driveway lined with Bradford Pear trees. Hand-forged iron-and-glass double entry doors open to a two-story foyer—a prelude to a five-tier jade-based crystal chandelier in the glass-wrapped great room. Generously scaled dining room, family room, chef's kitchen flow seamlessly across the main level. Six-burner range with built-in indoor grill, granite counters, custom cabinetry, island, walk-in pantry. Main-floor in-law suite with private balcony access offers single-level living. Upstairs, expansive primary suite anchors the second floor with dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office/yoga room. Two additional en-suite bedrooms; one with a home office that converts back to a bedroom. Attached 1,482 sqft garage—one of the home's most useful features—offers true five-car capacity with substantial workspace. === SCHOOLS & LOCATION Monroe-Woodbury Central School District — strong athletic tradition with cross country state championships (2022-2024) and Class AA football finals appearances. School bus stop at the front. 5 min to Woodbury Common Premium Outlets (world's largest luxury designer outlet, 250+ stores) and I-87. 9 min to Harriman train (to Penn Station in ~1 hour). West Point 25 min, Bear Mountain 15, Legoland 20. Orange County orchards, wineries, and farm-to-table restaurants throughout the area. A commuter location with the lifestyle of a country estate.

23 Greenwich Avenue, Woodbury
$939,888
5 Beds ⋅ 3 Baths ⋅ 990891 MLS
NEW PRICE – motivated seller! Exceptional Value in Tuxedo Park! and experience this architecturally designed home bordering Sterling Forest State Park. A truly one-of-a-kind, Frank Lloyd Wright inspired contemporary home, privately set among nature with forest and seasonal lake views, bordering protected state land with Sterling Forest State Park as your backyard. Nestled in the highly sought-after Laurel Ridge community of Tuxedo Park, this 5-bedroom, 2.5-bath residence blends timeless architectural design with modern comfort in a peaceful, retreat like setting. The open-concept layout is filled with natural light from walls of glass, highlighting new hardwood floors throughout and a striking wood-burning fieldstone fireplace. The home seamlessly connects indoor and outdoor living with expansive decking and a sunroom overlooking the woods. The fully renovated kitchen features a large island, high-end finishes, and a Tyent water purifier (installed at the kitchen sink), complemented by a whole-house water filtration/conditioning system. Updated bathrooms and thoughtful upgrades make this home completely move-in ready. The primary suite is a true standout, offering an expansive layout with: • Private sitting area/library • Walk-in closet • Spa-like en suite bathroom with soaking tub + separate standing shower • Private Juliet balcony with serene forest views Additional highlights include a fully heated office/studio/workshop with a separate entrance ideal for remote work or creative use. *** MUNICIPAL WATER and CITY SEWER*** *** LOW TAXES*** Recent upgrades include German Vecka European windows, BRAND NEW HOT WATER HEATER*** a new RUBBER ROOF, NEW GENERATOR** fiber cement insulated siding, a new asphalt driveway, surround sound, a whole-house generator hookup, and a TESLA CHARGER. Comfort is enhanced with 2-zone A/C and a first-floor laundry/mudroom. Set on a private lot with unobstructed forest views, the property also features a 2-car garage and parking for up to 6 vehicles. •NO HOA FEES Location Highlights: •Minutes to Tuxedo Station on the Metro-North Port Jervis Line, offering an easy commute to NYC • Minutes to major highways including the New York State Thruway and Route 17 • Approx. 15 minutes to local wineries including Thorne Valley Vineyard • Close to Warwick Valley Farmers Market and nearby farms • Convenient to shopping including ShopRite and Stop & Shop • Nearby dining options like Eddie’s Roadhouse and Draft House, Characters, Seven Lakes Station Craft Burgers, Valley Rock inn • Located within the highly regarded Monroe-Woodbury School District- close to playgrounds. • Minutes from the prestigious Tuxedo Club Tennis Courts, golf course, and private club amenities. • LOCATED ONLY 10 Minutes from WOODBURY COMMON OUTLETS Unique. Private. Turnkey. A rare architectural gem that feels like a getaway—yet remains close to everything.

20 Fawn Hill Road, Tuxedo Park
$650,000
5 Beds ⋅ 3 Baths ⋅ 960068 MLS
Welcome to this beautifully updated Colonial nestled in the highly sought-after community of Highland Mills, within the coveted Woodbury Recreation District. Built in 1995 and set in a picturesque, well-established development, this spacious home offers 4 generously sized bedrooms and 2.5 bathrooms—perfect for comfortable everyday living and entertaining alike. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The second floor features brand-new flooring, adding a modern touch and enhancing the home’s overall appeal. The layout offers a seamless flow with ample living space designed to suit today’s lifestyle. A full finished basement provides incredible versatility—ideal for a home theater, gym, playroom, or additional living area. Enjoy the added benefit of lake access, along with all the amenities that come with being part of the Woodbury Recreation District, making this location as desirable as the home itself. With its combination of updates, new updated retaining wall and stairs that leads to backyard. Hot water heater and much more, Home in prime location in a beautiful neighborhood. Don’t miss your opportunity to own in one of Highland Mills’ most desirable communities!

3 Emory Road, Highland Mills
$625,000
3 Beds ⋅ 3 Baths ⋅ 968339 MLS
Beautifully updated oversized high ranch in a cul-de-sac, with generously sized rooms, sitting on great flat almost 1/2 acre of property with an updated pool and fenced private backyard. Light and bright with new recessed lighting throughout the house, the renovated kitchen has all new appliances, cabinets, countertops and tile flooring and the primary bedroom has walk-in closet and ensuite bathroom. Pretty hardwood floors throughout the living areas on the first floor and all the big bedrooms have new laminate flooring. The backyard has a big screened in deck and a brand new deck around the pool with a new liner and pump/filter. Downstairs you will find three more rooms that can be used as a den/family room, office, playroom or whatever your heart desires and the laundry room. Plenty of parking and a one car garage. Great commuter location and walking distance to restaurants, deli and other local shops. Close to major highways, schools, Woodbury Common outlets and many other shopping areas and join the Woodbury parks and recreation and town pool!

41 Rutledge Avenue, Highland Mills
$775,000
5 Beds ⋅ 3 Baths ⋅ 976052 MLS
Welcome to this meticulously maintained 2,180 sq. ft. Colonial-style home, perfectly situated on over an acre of lush, private land on a quiet cul-de-sac. The main level boasts a bright and airy floor plan, highlighted by a spacious dining room with oversized windows that flood the space with natural light. The large kitchen offers ample wood cabinetry and a separate dining area, ideal for both everyday living and hosting. ?This home features a flexible layout with four total bedrooms and three full bathrooms. The primary suite serves as a true retreat, featuring an en-suite bath with a custom 4x4x3 whirlpool soaking tub. The first floor includes a dedicated guest wing with its own private entrance, closet space, and a second whirlpool tub, offering an excellent solution for multi-generational living or a quiet professional study. ?Significant high-value upgrades provide peace of mind, including new parquet flooring throughout the first floor reinforced with 3/4" plywood, a fully reconstructed fireplace and chimney, a modern propane boiler, and an updated electrical panel. Additional features include an insulated attic for energy efficiency, a large exterior awning, and a one-car attached garage. Residents benefit from the highly-rated Monroe-Woodbury School District and exclusive access to Woodbury Recreation amenities, including the Earl Reservoir and Central Valley Pool.

41 Serpi Road, Highland Mills
$899,000
5 Beds ⋅ 5 Baths ⋅ 962547 MLS
Stop searching, because you have just found your dream home. Situated on over an acre of land, this gorgeous home has over 2600 sqft. of space to call your own. Living area, kitchen with granite countertops, and finished basement. With less than 15 minutes drive to Woodbury Commons shopping center, this is a gem of a house. Whether it's for you or your family, this is a place you can make your own.

4 Lambros Drive, Monroe
$380,000
2 Beds ⋅ 2 Baths ⋅ 913681 MLS
Looking for the perfect starter or downsizer? This 2 Bedroom, 1.5 Bathroom Townhouse end unit in Village of Woodbury might be for you! Close to I-87 shopping, schools and amenities.

20 Redwood Drive, Highland Mills

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.