36

Highland Mills, NY Homes for Sale with Pool

Section Image Section Image
  • /37

    $399,000

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft

    7 Crestwood Trail, Monroe, NY 10950

    Perfect starter home, Investment opportunity or your weekend getaway! Welcome to this 3-bedroom home in Blooming Grove in Washingtonville School District with Low Taxes, step into a welcoming living room with a cozy wood-burning fireplace that flows into a modern eat-in kitchen boasting beautiful granite countertops and plenty of cabinetry, with gleaming wood floors throughout. The full walk

    Agent Photo

    Alexandra Zinko

    Century 21 Realty Center

    (845) 606-3789

    7 Crestwood Trail, Monroe, NY 10950
  • /27

    $499,000

    • 4 Beds
    • 4 Baths
    • 2,800 Sq Ft

    4 Linden Dr, Highland Mills, NY 10930

    Welcome to this rare 4-bedroom, 4-bathroom townhome in the sought-after Timber Ridge community of Woodbury, NY—offering many updates, and a versatile location! This spacious multi-level home features a brand new roof (installed June 2025) and an open-concept main level with vaulted ceilings, skylights, and sun-drenched interiors. The oversized kitchen flows into the dining area, which opens to a

    Agent Photo

    Erin Connolly

    Artisan Realty

    (845) 393-6635

    4 Linden Dr, Highland Mills, NY 10930
  • /28

    $190,000

    • 1 Bed
    • 1 Bath
    • 813 Sq Ft

    43 Tanager Rd Unit 4305, Monroe, NY 10950

    Welcome to Rolling Hills Condominiums! This 1-bedroom, 1-bath unit offers a spacious layout with a separate living room and dining room. The dining area leads out to a private balcony through sliding glass doors, perfect for relaxing or entertaining. The kitchen is efficiently laid out and ready for your updates. Heat, hot water, and cooking gas are all included in the HOA fees. Ideal location

    Agent Photo

    John Olivero

    KELLER WILLIAMS REALTY

    (845) 393-3645

    43 Tanager Rd Unit 4305, Monroe, NY 10950
  • /42

    $500,000 Open Fri 5PM - 7PM

    • 2 Beds
    • 4 Baths
    • 2,176 Sq Ft

    2 Peter Turner Rd, Monroe, NY 10950

    Are you ready to move? Come see this luxury townhouse before it's too late! 2-bedrooms, plus a loft/office area, 2 full bathrooms, 2 half bathrooms, and a two-car garage with a long private driveway. The entryway, dining room, and living room have hardwood floors, 9’ ceilings, and plenty of sunshine with extra windows in this spacious end unit. A nature lovers deck connects from the eat-in

    Lynda Hoss Weichert Realtors

    2 Peter Turner Rd, Monroe, NY 10950
  • /49

    $979,000

    • 4 Beds
    • 3.5 Baths
    • 4,290 Sq Ft

    9 Roselawn Rd, Highland Mills, NY 10930

    Luxury Awaits! Slide open all of your back doors to...Your own private "Country Club"!!! Exquisite heated pool with fiberglass coating and "Sunshelf", surrounded by an oversized deck of beautiful pavers, AND a POOL HOUSE with kitchenette, 1/2 bath, and sitting room! Tall trees line the back of the property, and the greenery continues to the right side of yard, with a beautiful black gate with

    Joanne Cooper Hudson Heritage Realty

    9 Roselawn Rd, Highland Mills, NY 10930
  • /32

    $650,000

    • 3 Beds
    • 2 Baths
    • 1,644 Sq Ft

    1500 New York 32, Highland Mills, NY 10930

    Welcome to this charming ranch-style home featuring a wrap-around rocking chair porch, an in-ground pool, and a 1,500+ sq ft pole barn, all set on a picturesque 3.6-acre lot with a sprawling, field-like yard and plenty of driveway parking. Inside, enjoy the ease of single-level living with three bedrooms, two full bathrooms (one in the primary bedroom), a cozy fireplace in the living area, and a

    Nicholas Cuomo Keller Williams Realty

    1500 New York 32, Highland Mills, NY 10930
  • /50

    $899,000

    • 6 Beds
    • 3.5 Baths
    • 4,517 Sq Ft

    3 Caledonia Cir, Highland Mills, NY 10930

    Welcome to 3 Caledonia Circle: A Luxurious Haven in the Brigadoon CommunityImagine stepping into a stunning home that exudes elegance and sophistication. The beautiful big house boasts a majestic double-ceiling entryway with big chandeliers that sparkle and shine, setting the tone for a luxurious living experience. The expansive living room is a bright and airy space with double ceilings

    Yakov Winkler Preferred Properties Real Esta

    3 Caledonia Cir, Highland Mills, NY 10930
  • /36

    $839,000

    • 5 Beds
    • 4.5 Baths
    • 3,182 Sq Ft

    1 Cindy Ln, Highland Mills, NY 10930

    NEW!! Discover the epitome of luxury living in this magnificent, one-of-a-kind home!! Nestled in a highly sought-after neighborhood. This stunning property boasts an expansive layout, offering ample space for both relaxation and entertainment. The heart of the home is the magnificent kitchen, featuring elegant granite countertops that blend style and functionality, perfect for culinary

    Joseph Rosenfeld Flag Realty Group

    1 Cindy Ln, Highland Mills, NY 10930
  • /4

    $887,000

    • 5 Beds
    • 2 Baths
    • 2,000 Sq Ft

    5 Tappan Dr, Monroe, NY 10950

    Don't miss out on this opportunity to own your lakefront dream home situated on a quiet, half acre, cul-de-sac in the village of South Blooming Grove.You will be minutes away from major highways, close to supermarkets and everything this neighborhood has to offer. Whether you're lookingto move in, build you own dream home or invest, this is the home for you!

    Shalom Landau eRealty Advisors, Inc

    5 Tappan Dr, Monroe, NY 10950
  • /27

    $364,000

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft

    71 Frank Ct, Monroe, NY 10950

    You can truly have it all in this exceptional nearly 1160 sq. ft. condo. This upper unit offers 2 Bedroom and 2 full bathrooms, a large living room with light colored carpeting, a formal dining room, with real wood parquet flooring that flows into a spacious kitchen with receded lighting, new stone back-splash, granite counter-top, custom hanging light, 5 burner stove and a side-by-side

    Dennis Chiulli Dennis L Chiulli Realty Corp

    71 Frank Ct, Monroe, NY 10950
  • /21

    $735,000

    • 4 Beds
    • 2.5 Baths
    • 2,566 Sq Ft

    3 Moorefield Cir, Highland Mills, NY 10930

    Welcome to the highly desirable Brigadoon community, ideally situated on a quiet cul-de-sac! This elegant colonial home offers 4 spacious bedrooms and 2.5 bathrooms, along with a 2-car garage. The sunlit eat-in kitchen is a chef’s dream, featuring granite countertops, a center island, ceramic tile flooring, and a convenient butler’s pantry—perfect for entertaining. The expansive primary suite

    Jacob Fried Keller Williams Realty

    3 Moorefield Cir, Highland Mills, NY 10930
  • /45

    $649,999

    • 4 Beds
    • 2.5 Baths
    • 3,342 Sq Ft

    41 Woodcock Mtn Rd, Washingtonville, NY 10992

    PRICE IMPROVED!! READY FOR A QUICK CLOSING!!! Welcome to a home that has been lovingly maintained and beautifully updated—a true testament to pride in ownership! Perfectly situated on a picturesque 1-acre lot in the highly sought-after Washingtonville School District, this quality-built Colonial offers comfort, space, and timeless charm. From the moment you arrive, you'll sense that this property

    Frank Muccari Cronin & Company Real Estate

    41 Woodcock Mtn Rd, Washingtonville, NY 10992
  • /48

    $694,900

    • 4 Beds
    • 1.5 Baths
    • 2,220 Sq Ft

    33 Winchester Dr, Monroe, NY 10950

    Located in the desirable Monroe-Woodbury School District, this classic 2,220 sq ft colonial offers a rare combination of space, comfort, and future potential. Set on a gentle hill in a picturesque, sidewalk-lined neighborhood, the property features four spacious bedrooms, two bathrooms, and a well-balanced layout that includes a formal dining room, a living room, and a separate family room.

    Dennis Clark Howard Hanna Rand Realty

    33 Winchester Dr, Monroe, NY 10950
  • /14

    $354,995

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft

    37 Aldo Ct, Monroe, NY 10950

    This is a one of a kind very commuter friendly location. Come visit this ground floor end unit walk into this very spacious living room and formal dining area. The kitchen also is very spacious with sliding glass door overlooking a walk out patio backing into the privacy of the woods. There are two nice size bedrooms with a walk-in closet. the unit also has two full bathrooms .and a utility room

    Rhoda Ciancio Real Estate Connection Corp

    37 Aldo Ct, Monroe, NY 10950
  • /29

    $475,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft

    20 Grove St, Harriman, NY 10926

    Charming Single-Family Home in Harriman, NY – Monroe-Woodbury Schools. Welcome to this beautifully maintained 3-bedroom, 1.5-bath home located in the heart of Harriman, NY. Situated within the highly desirable Monroe-Woodbury School District, this home combines style, comfort, and convenience. The main level features gleaming hardwood floors throughout and a modern kitchen with granite

    Courtney Tablante Keller Williams Realty

    20 Grove St, Harriman, NY 10926
  • /35

    $329,999 Open Sun 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,266 Sq Ft

    207 Arlin Rd, Monroe, NY 10950

    Welcome to easy living at Cromwell Hills! This charming first-floor condo offers 2 spacious bedrooms and 2 full bathrooms with a traditional layout that provides separation and privacy between living spaces—perfect for those who prefer clearly defined rooms over open concept.The primary suite is a standout, featuring a full bathroom plus a bonus vanity area with a separate sink and mirror

    Vincent Reda Keller Williams Realty

    207 Arlin Rd, Monroe, NY 10950
  • /26

    $239,000

    • 2 Beds
    • 1.5 Baths
    • 1,025 Sq Ft

    40 Tanager Rd Unit 4002, Monroe, NY 10950

    Welcome to Rolling Hills Condominiums in Monroe! This spacious 2-bedroom, 1.5-bath unit offers a thoughtfully designed layout with separate living and dining rooms. Enjoy the ease of low-maintenance living with heat, hot water, and cooking gas all included in the HOA fees. Ideally located for commuters, you're just minutes from the NYC bus and train, and only an hour from the city. Conveniently

    Dvora E. Price eXp Realty

    40 Tanager Rd Unit 4002, Monroe, NY 10950
  • /33

    $349,000

    • 3 Beds
    • 1.5 Baths
    • 1,361 Sq Ft

    9 Heritage Dr Unit B, Harriman, NY 10926

    COMING SOON!!! Welcome to the Harriman Hill Community! This move-in ready 3-bedroom, 1 full and half bathroom townhome offers comfortable living in a highly convenient location. The main level features a spacious living and dining area with wood flooring, sliding glass doors open to a cozy porch area, powder room, and an updated kitchen with stainless steel appliances. Freshly painted throughout!

    Nicole Isaacs Century 21 Full Service Realty

    9 Heritage Dr Unit B, Harriman, NY 10926
  • /28

    $305,000

    • 2 Beds
    • 2 Baths
    • 1,266 Sq Ft

    305 Arlin Rd, Monroe, NY 10950

    If you're looking for one level living with handicapped friendly features you have found your perfect new home. The Cromwell Hills community is within walking distance to the village. The community is quiet and well maintained with well manicured lawns and common areas, a pool and clubhouse and playground area. There is reserved parking and guest parking nearby. The layout is perfect for

    Theresa Budich Howard Hanna Rand Realty

    305 Arlin Rd, Monroe, NY 10950
  • /40

    $1,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,570 Sq Ft

    10 Greenwich Ave, Central Valley, NY 10917

    "LE CHÂTEAU des VERTS": Unparalleled, Unprecedented and Poised...Inspired by castles on the rolling hills of the French countryside and perfectly perched here in the Hudson Valley, there's no wonder why this custom-built one-of-a-kind French Château is known to its neighborhood residents as 'The Castle on the Hill'. Incredibly designed inside and out with no detail spared, this 4,500+

    Micaela Stanaland Howard Hanna Rand Realty

    10 Greenwich Ave, Central Valley, NY 10917
  • /10

    $1,095,000

    • 4 Beds
    • 2.5 Baths
    • 2,311 Sq Ft

    11 Cliff Ct, Monroe, NY 10950

    Welcome to your private retreat in the heart of Monroe! Tucked into a serene neighborhood, this charming 4 bedroom, 2.5 bath offers the perfect blend of indoor comfort and outdoor enjoyment. Set on a beautifully landscaped lot, the home greets you with a long driveway leading to the attached 2 car garage. Enter to find a bright and inviting home with hardwood floors, recessed lighting and a cozy

    Derek Eisenberg Continental Real Estate Group

    11 Cliff Ct, Monroe, NY 10950
  • /43

    $435,000

    • 3 Beds
    • 2.5 Baths
    • 1,704 Sq Ft

    13 Butternut Ct, Highland Mills, NY 10930

    Don't wait!JUST REDUCED! FANTASTIC PRICE !!! A great place to call "home"...Spacious 3BD, 2.5 BTH home with so many outstanding features...Beautiful decorator designed living room built-in wall unit with lighting and stunning dark wood floors, garage, lovely patio, skylight, beautiful kitchen with tons of granite (even a custom granite breakfast bar AND EXTRA CABINETS and shelving), stainless

    Joanne Cooper Hudson Heritage Realty

    13 Butternut Ct, Highland Mills, NY 10930
  • /46

    $324,900

    • 2 Beds
    • 1.5 Baths
    • 1,260 Sq Ft

    1 Heritage Dr Unit C, Harriman, NY 10926

    Beautiful and Unique END UNIT townhome with professionally designed gardens, Model to the complex, features 2 spacious bedrooms, office, 1 remodeled full bathroom, (Newly re glazed 10 yr warranty tub!) 1/2 bath and charming touches throughout. Including: Gleaming hardwood floors up/down! Freshly painted! Large Fireplace! New Stainless Steel Appliances! New A/C units! New Water Softener! Ceramic

    Claire Ryan ARC Realty 1 in Sales

    1 Heritage Dr Unit C, Harriman, NY 10926
  • /47

    $649,000

    • 4 Beds
    • 3 Baths
    • 2,352 Sq Ft

    229 Orchard Dr, Monroe, NY 10950

    Step into luxury with this fully renovated 4-bedroom, 3-bathroom home, transformed in 2023 with the finest finishes and attention to detail. The expansive living room invites you to relax by the natural gas fireplace, creating a cozy yet elegant atmosphere. The chef's kitchen is a dream, featuring sleek stainless steel appliances, stunning granite countertops, and custom cabinetry, seamlessly

    Moche Halpern Blooming Realty

    229 Orchard Dr, Monroe, NY 10950
  • /50

    $620,000

    • 4 Beds
    • 2 Baths
    • 3,330 Sq Ft

    114 Old Mansion Rd, Chester, NY 10918

    Charming Colonial with 4 Bedrooms on Nearly an Acre – Prime Location!Welcome to this beautifully maintained Colonial-style home nestled on a generous 0.92-acre lot, offering space, comfort, and convenience. This freshly painted home features 4 spacious bedrooms, 2 full bathrooms, and a versatile layout perfect for modern living.The first floor boasts gleaming hardwood floors, a

    Hershel Lowy Master Realty Group Inc.

    114 Old Mansion Rd, Chester, NY 10918
  • /44

    $579,900

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    22 Ford Ct, Monroe, NY 10950

    Welcome to 22 Ford Court, Monroe – A Turn-Key Gem in Meadow Glen!Move right into this beautifully maintained 3-bedroom, 2.5-bathroom home, nestled on a quiet cul-de-sac within the desirable gated community of Meadow Glen. This property offers the perfect blend of style, modern upgrades, and peace of mind living.Step inside to find gleaming hardwood floors and a bright, open

    Amanda Rivera Sepulveda Keller Williams Realty

    22 Ford Ct, Monroe, NY 10950
  • /50

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,538 Sq Ft

    1 Billy Ave, Washingtonville, NY 10992

    Welcome home to 1 Billy Avenue! The best property for your money right now in Charming Washingtonville! Lots of improvements! You'll be amazed at this wonderful home. This property spans nearly one acre and features a flat corner lot with a long, paved driveway capable of accommodating numerous vehicles. Upon entering through the front door, you will be greeted by exquisite, lightly stained,

    Robert Pape Keller Williams NY Realty

    1 Billy Ave, Washingtonville, NY 10992
  • /10

    $220,000

    • 1 Bed
    • 1 Bath
    • 813 Sq Ft

    49 Tanager Rd Unit 4905, Monroe, NY 10950

    One bedroom top unit in mint condition. Large living room, oversized bedroom, kitchen and dining area full bath

    Joseph Morello Keller Williams Hudson Valley

    49 Tanager Rd Unit 4905, Monroe, NY 10950
  • /35

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,484 Sq Ft

    576 Bull Mill Rd, Chester, NY 10918

    A fantastic opportunity for investors or future homeowners! This well-maintained 3-bedroom, 2-bath home is set on a large, flat lot in a quiet, nature-filled neighborhood and offers strong rental potential with long-term flexibility. Inside, you’ll find a spacious living room, formal dining area, kitchen, and comfortable layout ideal for everyday living. Recent updates include fresh interior

    Lazar Schvimmer Blooming Realty

    576 Bull Mill Rd, Chester, NY 10918
  • /49

    $1,495,000

    • 4 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    421 Spring St, Monroe, NY 10950

    Introducing The Spring Hill House, a rare gem in the heart of Monroe, a short stroll to Kiryas Joel Gate shopping & conveniences. Set on 2.6 serene, park-like acres, this Queen Ann estate, offers both a grand main house & a potential accessory home. The elegant interior boasts a custom kitchen w/ luxurious marble & onyx backsplashes & countertops hardwood floors, formal dining room, living room,

    Harry Donofrio Town and Village Real Estate

    421 Spring St, Monroe, NY 10950
  • /37

    $510,000

    • 3 Beds
    • 2.5 Baths
    • 1,671 Sq Ft

    87 Barr Ln, Monroe, NY 10950

    Beautiful Townhouse Style Condo located in the sought after Meadow Glen of Monroe. This 3 bedroom condo offers 3 levels of living. Entry foyer leads to stairs to formal living room and gorgeous eat in kitchen with new stainless steel appliances , Master bedroom suite with private bath, 2 additional bedrooms , 1 car Garage, all town services and close to all major highways for commuting

    Kathleen Milich RE/MAX Benchmark Realty Group

    87 Barr Ln, Monroe, NY 10950
  • /50

    $629,000

    • 4 Beds
    • 2.5 Baths
    • 2,892 Sq Ft

    7 Briarwood Ave, Monroe, NY 10950

    Welcome to this beautiful home located at 7 Briarwood! This oversized residence has recently been renovated and sits on a flat property of over half an acre, bordered by woods that will never be developed, ensuring your privacy. The first floor features a spacious granite kitchen, a generously sized dining room, and a lovely sunroom that can be enjoyed year-round. You'll also find an

    Joel Basch eRealty Advisors, Inc

    7 Briarwood Ave, Monroe, NY 10950
  • /36

    $540,000

    • 3 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    76 Pine Hill Rd, Highland Mills, NY 10930

    This move-in ready home is beautifully maintained and nestled in a prime peaceful area of Woodbury. Three bedrooms and two and a half baths, with full bathroom off primary bedroom. Granite counter tops. Hardwood floors. Pellet Stove for winter days. Enclosed deck for seasonal dining overlooks beautiful yard. 2 car attached garage with spacious driveway. Roof 6 years young. Whole house generator

    Edward Scully ARC Realty 1 in Sales

    76 Pine Hill Rd, Highland Mills, NY 10930
  • /26

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    241 Smith Clove Rd, Highland Mills, NY 10930

    What a view! Charming cottage style home located on 1.5 private acres is adjacent to open land and has splendid views of the surrounding mountains! Just an hour or so from New York City, this is a perfect spot for your weekend getaway. Or make it your new home! The house is in the Monroe Woodbury school district and includes the coveted Woodbury Recreation – the John Burke Memorial Pool, also the

    Karin Poggio HomeSmart Homes & Estates

    241 Smith Clove Rd, Highland Mills, NY 10930
  • /26

    $2,999,999

    • 4 Beds
    • 4.5 Baths
    • 4,461 Sq Ft

    101 Mountain Lodge Rd, Washingtonville, NY 10992

    "Sunset Lodge," carefully curated and impeccibly maintained, is available for only the third time. This once in a lifetime estate comprises 38 acres, yet is only 7 minutes from Metro North NJ Transit. Exquisite main home, two ponds, 20 acres fenced (+10 wooded acres), a six stall horse barn with apartment, spectacular warm weather entertaining area with stunning 18 x 65 foot infinity pool, 8

    Susan Rost Tux Park Towne & Country

    101 Mountain Lodge Rd, Washingtonville, NY 10992
  • /25

    $559,000

    • 3 Beds
    • 2.5 Baths
    • 1,865 Sq Ft

    3 Webster Ct, Monroe, NY 10950

    Enjoy this spacious 3-bedroom townhouse in gated community. well maintained complex- Great open floor plan that will be perfect for gatherings. Gas fireplace adds to the beauty of the living room. Sliding doors lead to a rear yard deck. New bathroom - Plenty of closet space- Unfinished basement with sliding door and windows. Can possibly be finished. Monroe-Woodbury Schools - Close to

    Kevin Abrams Hudson Heritage Realty

    3 Webster Ct, Monroe, NY 10950
How to Buy a Home How to Finance a Home How to Sell a Home