Orange County NY Homes for Sale with Private Pool

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  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,866 Sq Ft

  2948 State Route 94, Chester, NY 10918

  Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

  Elizabeth Broderick Tuxedo Hudson Realty Corp

  2948 State Route 94, Chester, NY 10918
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  $850,000

  • 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
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  /34

  $999,000

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
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  /33

  $539,900

  • 3 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  310 Highland Ave, Maybrook, NY 12543

  Come and see this warm and cozy 3-bedroom, 1.5 bath home located in the heart of Orange County. The home is set in a residential neighborhood with comfortable spacing between homes, this property offers both privacy and charm. Step into a welcoming foyer that opens to an eat-in kitchen with a breakfast bar and doors that lead out to a deck. The foyer also opens to a bight living room with a wood

  Maria Siciliano Coldwell Banker Prime

  310 Highland Ave, Maybrook, NY 12543
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  /43

  $335,000

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft

  51 Deer Ct Dr, Middletown, NY 10940

  Welcome to this townhouse-style condo in Middletown, offering 2 bedrooms and 2.5 bathrooms. The first floor features a functional layout with a kitchen that opens to a dining area, a spacious living room, and a half bath. The kitchen offers a practical galley-style layout with ample cabinetry and counter space for everyday living. The open-concept living area provides a flexible layout for

  Jie Liu Keller Williams Hudson Valley

  51 Deer Ct Dr, Middletown, NY 10940
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  /26

  $1,125,000

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft

  22 Weyant Rd, Fort Montgomery, NY 10922

  Step into this stunning contemporary home, where soaring ceilings and intentional design create a truly elevated experience, set on an acre of land, on the private picturesque hills of Fort Montgomery. Flooded with natural light, the open concept floor plan seamlessly connects the kitchen, dining, and living areas, including two fireplaces. Perfect for entertaining or relaxing. This meticulously

  Tierney Dodge HomeSmart Homes & Estates

  22 Weyant Rd, Fort Montgomery, NY 10922
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  /25

  $599,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 1,906 Sq Ft

  3 Shoddy Hollow Rd, Mount Hope, NY 10963

  Welcome to 3 Shoddy Hollow Road! Built in 2021, this beautifully maintained bi-level home is perfectly situated in the quiet and charming Village of Otisville, offering an exceptional blend of modern comfort, functionality, and convenience. Featuring three spacious bedrooms and three full bathrooms, this home is thoughtfully designed to accommodate both everyday living and effortless

  Travis Thompson Keller Williams Hudson Valley

  3 Shoddy Hollow Rd, Mount Hope, NY 10963
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  /50

  $610,000

  • 4 Beds
  • 3.5 Baths
  • 2,384 Sq Ft

  55 Bailey Rd, New Hampton, NY 10958

  Set in a beautiful country setting, this gorgeous Colonial offers the perfect blend of classic charm and modern comfort. Step inside to discover hardwood floors throughout and a stunning kitchen featuring granite countertops, ideal for everyday living and entertaining alike. The home boasts a huge family room anchored by a striking stone fireplace, creating a warm and welcoming gathering space.

  Robin Cohen Keller Williams Realty

  55 Bailey Rd, New Hampton, NY 10958
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  /31

  $445,000

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  4 James St, Harriman, NY 10926

  This home is a must see in commuter friendly Harriman! Completely renovated in 2021/2022, this home features a gorgeous upgraded kitchen with stainless refrigerator and dishwasher, quartz countertops, an island and marble tile flooring. On the first floor, you enter through the enclosed front porch, into the foyer and are greeted by beautiful hardwood floors and recessed lighting throughout the

  Michelle Renteria HomeSmart Homes & Estates

  4 James St, Harriman, NY 10926
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  $605,000

  • 4 Beds
  • 3 Baths
  • 2,132 Sq Ft

  125 White Bridge Rd, Middletown, NY 10940

  This home offers so much more than a new build. Enjoy 2,132 square feet of well maintained, comfortable living space, topped with a brand new roof. Set on 2.6 beautiful acres in a serene country setting, the property’s signature feature is its fully owned solar array. No roof penetrations, no lease agreements — just clean energy and real savings. Electric bills as low as $28 per month speak for

  Anthony Spadaro RE/MAX Benchmark Realty Group

  125 White Bridge Rd, Middletown, NY 10940
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  /37

  $2,000,000

  • 6 Beds
  • 5.5 Baths
  • 6,254 Sq Ft

  63 Colonial Ave, Warwick, NY 10990

  Set on nearly three acres in the heart of Warwick’s historic village, Breckenridge is a commanding example of Greek Revival architecture—its stately brick facade, soaring columns, and symmetrical proportions echoing the grandeur of a bygone era. Built in 1911, the residence spans over 6,200 square feet across three levels, offering six bedrooms, five-and-a-half baths, and a wealth of original

  Christine Vande Vrede Chapin Sotheby's Intl Rlty

  63 Colonial Ave, Warwick, NY 10990
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  $499,000

  • 2 Beds
  • 4 Baths
  • 1,777 Sq Ft

  32 Peter Turner Rd, Monroe, NY 10950

  Rare Hidden Creek end-unit luxury! This sun-drenched 2-bedroom condo features 2 full and 2 half baths, an open-concept layout, and gleaming hardwood floors throughout. The stylish kitchen is a chef’s delight with stainless appliances, granite countertops, and a breakfast bar. Step through the sliders to your private back deck, perfect for alfresco dining. Upstairs, the spacious primary suite

  Beth Palma Keller Williams Realty

  32 Peter Turner Rd, Monroe, NY 10950
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  /41

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  51 Lakeside Rd, Newburgh, NY 12550

  This meticulously maintained 3-bedroom, 2-bath Cape Cod is situated on a private 1.2 acre lot, set back from the road in the sought after Valley Central school district. The main level offers a bright, open living and dining area, an eat-in kitchen, two comfortable bedrooms, and a recently updated full bath. Upstairs, the private primary suite features a spacious walk-in closet (so large it was

  Lyra Blumenthal RE/MAX Benchmark Realty Group

  51 Lakeside Rd, Newburgh, NY 12550
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  /58

  $575,000

  • 12 Beds
  • 10 Baths
  • 5,004 Sq Ft

  5 Wawayanda Place, Middletown, NY 10940

  CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

  Jamie Sittner Find Advisors

  5 Wawayanda Place, Middletown, NY 10940
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  /23

  $344,900

  • 4 Beds
  • 1.5 Baths
  • 1,598 Sq Ft

  16 Mountain Ave, Middletown, NY 10940

  Welcome to 16 Mountain Ave — a well-loved home with tons of potential in the heart of town! This spacious 4-bedroom, 1.5-bath Colonial offers the perfect blend of solid maintenance and room to make it your own. An estate property that’s been cared for throughout the years, it features original hardwood floors waiting to shine beneath the carpet, central air, and a layout that truly works for

  Valerie Jewis Keller Williams Realty

  16 Mountain Ave, Middletown, NY 10940
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  /37

  $450,000

  • 6 Beds
  • 2 Baths
  • 2,100 Sq Ft

  10 Congress Dr, Washingtonville, NY 10992

  6-bedroom, 2-bathroom home nestled in the desirable community of Washingtonville. With generous square footage, a brand-new renovated kitchen, and a large backyard, this property offers incredible potential for investors, or those looking to create their dream home. The heart of the home is the stunning new kitchen, featuring a large center island, modern cabinetry, and updated appliances –

  Danielle Russodivito New and Modern Group, LLC

  10 Congress Dr, Washingtonville, NY 10992
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  /50

  $1,395,000

  • 6 Beds
  • 7 Baths
  • 8,180 Sq Ft

  5 Trinity Place, Cornwall, NY 12518

  Set at the end of a private road and backing directly to the Storm King Golf Club, this mansion-style residence offers rare privacy, scale, and presence on 1.6 acres in Cornwall. The home spans approximately 8,180 square feet and showcases timeless architecture with classic, old-world character. Grand formal spaces balance nicely with more relaxed living areas, all highlighted by four fireplaces

  STEVEN WROBEL JR. Serhant LLC

  5 Trinity Place, Cornwall, NY 12518
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  /50

  $699,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  360 Prospect Rd, Chester, NY 10918

  B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

  Joseph Mendlowitz eRealty Advisors, Inc

  360 Prospect Rd, Chester, NY 10918
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  /27

  $700,000

  • 6 Beds
  • 2 Baths
  • 2,216 Sq Ft

  121 Renwick St, Newburgh, NY 12550

  3-PROPERTY PACKAGE SALE...Next to each other on a corner location with all municipal services. Affordable two family brick 3-bedrooms each unit attached home on two levels in City of Newburgh with small rear yard/parking, sidewalks and all municipal services. Walking distance to George Washington Headquarters, Newburgh Brewing Company, a variety of restaurants & shops, the Newburgh waterfront &

  George Koudounas RE/MAX Benchmark Realty Group

  121 Renwick St, Newburgh, NY 12550
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  /36

  $550,000

  • 3 Beds
  • 3.5 Baths
  • 2,078 Sq Ft

  6 Turnberry Ct, Monroe, NY 10950

  Welcome to Mansion Ridge! A beautiful gated community of townhomes. This spacious unit features a great layout with an open kitchen with cherry wood cabinetry and granite counters, a 2 story living room with a fireplace, a dining room, and loads of natural light. The upper level has 3 large bedrooms with lots of closets and the master bedroom has cathedral ceilings, a master bath and a walk in

  Naomi Streicher Q Home Sales

  6 Turnberry Ct, Monroe, NY 10950
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  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,174 Sq Ft

  62 Salierno Rd, Tuxedo Park, NY 10987

  Welcome to 62 Salierno Road in the sought-after Table Rock Estates - an inviting and beautifully situated home offering 4 large bedrooms, generous storage throughout, and a lifestyle defined by privacy, comfort, and connection to nature. Set on 1.5 acres backing to protected state land, this property offers a sense of seclusion rarely found in a neighborhood setting. Inside, the main level is

  Windy Rosengart

  62 Salierno Rd, Tuxedo Park, NY 10987
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  $499,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,312 Sq Ft

  23 Snow St, Bloomingburg, NY 12721

  Welcome to your private oasis in the heart of the Pine Bush School District! This impeccably maintained 1993 bi-level sits on 2 sprawling acres at the end of a quiet, peaceful street, offering the perfect blend of modern updates and country serenity. The heart of the home is the updated kitchen, featuring sleek granite countertops, a functional center island, and stainless steel appliances. The

  William Cronin Cronin & Company Real Estate

  23 Snow St, Bloomingburg, NY 12721
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  /37

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  2066 Route 6, Middletown, NY 10940

  This home is set on over 5 acres and is beautifully landscaped. This inviting home delivers space, comfort, and resort-style living at home. A true backyard oasis designed for relaxation and entertaining. Step outside to your private retreat featuring an above-ground heated pool with surrounding deck, an extended patio with a pergola swim-up bar, and multiple spaces to gather, unwind, and enjoy

  Juliska Martino Compass Greater NY, LLC

  2066 Route 6, Middletown, NY 10940
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  /50

  $829,500

  • 4 Beds
  • 2.5 Baths
  • 3,413 Sq Ft

  83 High Hope Dr, Otisville, NY 10963

  This spectacular home which can be used as a weekend retreat or an ideal home nestled on top of a mountain, on over 25 private acres with a serene pond, offering unmatched peace, beauty, and breathtaking eastern views of the sunrise from its expansive wrap-around porch. The property invites you to take walks or hikes through the woods and enjoy the sights and sounds of nature in complete privacy.

  Gail Rachlin Keller Williams Hudson Valley

  83 High Hope Dr, Otisville, NY 10963
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  /39

  $948,888

  • 6 Beds
  • 4 Baths
  • 2,600 Sq Ft

  14 Robalene Dr, Goshen, NY 10924

  Better-than-new 6BR/4BA Colonial just over 5yrs young with over $400K in upgrades and resort-style amenities. Gourmet kitchen with granite countertops, stainless steel appliances, hardwood floors, and fireplace. First floor also includes dining room, flex room/den/playroom or possible 6th BR and full bath. Second floor boasts primary suite with custom walk-in closet and spa bath featuring steam

  David White Owner Entry.com

  14 Robalene Dr, Goshen, NY 10924
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  /50

  $1,750,000

  • 5 Beds
  • 5.5 Baths
  • 6,348 Sq Ft

  7 Paiges Way, Warwick, NY 10990

  Discover this stunningly appointed 5-bedroom, 5.5-bath home nestled on 4.1 acres in beautiful Warwick, New York. This elegant and turnkey residence is perfect for both comfortable living and entertaining guests. Enjoy the luxurious in-ground pool, expansive living areas, and a beautifully serene yard. The lower level features gaming area, a custom bar, and a luxurious bathroom, creating an ideal

  Steve Vinti Weichert Realtors

  7 Paiges Way, Warwick, NY 10990
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  /48

  $620,000

  • 5 Beds
  • 2 Baths
  • 2,220 Sq Ft

  33 Winchester Dr, Monroe, NY 10950

  HUGE PRICE REDUCTION- 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

  Dennis Clark Howard Hanna Rand Realty

  33 Winchester Dr, Monroe, NY 10950
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  /24

  $362,900

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  2203 Whispering Hills, Chester, NY 10918

  Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

  Marie Altieri Howard Hanna Rand Realty

  2203 Whispering Hills, Chester, NY 10918
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  /50

  $699,999

  • 5 Beds
  • 4 Baths
  • 3,858 Sq Ft

  254 Orrs Mills Rd, New Windsor, NY 12553

  This custom-built Contemporary Colonial captures breathtaking mountain views from every direction and features cathedral-style ceilings, a gas fireplace in the great room, and gorgeous daily sunset views. Set on a private 2-acre property, the home offers over 4,000 sq ft of sunlit living space with vaulted ceilings, skylights, Andersen windows, three fireplaces, two dens with Brazilian hardwood

  Bryan Dale eXp Realty

  254 Orrs Mills Rd, New Windsor, NY 12553
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  /31

  $649,999

  • 5 Beds
  • 6 Baths
  • 3,568 Sq Ft

  7 Cherrywood Dr, Goshen, NY 10924

  This beautiful, spacious contemporary split-level home is perfect for the in-laws, featuring a separate apartment. The main house boasts 5 bedrooms and 4 bathrooms, with an entrance foyer leading to a large entertaining room with Fireplace. From there, you can move into the media room and then onto separate entrance to pool areaOn the main level, features hardwood floors threw out home. Large

  Joseph Brown RE/MAX Real Property Group

  7 Cherrywood Dr, Goshen, NY 10924
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  /17

  $439,000

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  9 Carpenter Rd, Port Jervis, NY 12771

  This spacious 3-bedroom, 2.5-bath ranch offers 1,976 sq. ft. of one-level living on a beautiful corner lot in Deer Park, just minutes from Port Jervis. Enjoy the charm of a mid-century layout with modern updates including a new roof (2021), mini-split A/C units (2023), updated 200-amp electrical service, new well pump, and a pellet stove serviced yearly for efficient heating. The property

  Rachel Hunt Realty Promotions Inc

  9 Carpenter Rd, Port Jervis, NY 12771
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  /48

  $995,000

  • 3 Beds
  • 4 Baths
  • 3,188 Sq Ft

  736 State Route 94 N, Warwick, NY 10990

  Welcome to your ultimate private oasis in the Town of Warwick! Set on a sprawling 15.5-acre estate complete with a tranquil pond and stream, this stunning, expansive Ranch offers nearly 3,200 square feet and more of luxurious living space. Boasting 3 spacious bedrooms, 4 full bathrooms, this home is thoughtfully designed for both grand entertaining and everyday comfort. Step inside to a

  Jason McGovern Keller Williams Hudson Valley

  736 State Route 94 N, Warwick, NY 10990
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  /24

  $479,000

  • 4 Beds
  • 2 Baths
  • 1,322 Sq Ft

  5 Berkley Terrace, Monroe, NY 10950

  Lake Rights! Low Taxes! Welcome home to this lovely cape, beautifully situated on a double lot allowing for plenty of yard space for peace and privacy. This home features 4 bedrooms and 2 full bathrooms with a large eat-in kitchen, wood floors and a spacious unfinished, walk-out basement. Walk-out from the kitchen onto a lovely deck for grilling, dining and relaxing as you take in the tree-top

  Layla Rose Boyles Century 21 Realty Center

  5 Berkley Terrace, Monroe, NY 10950
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  /48

  $869,000

  • 5 Beds
  • 2 Baths
  • 1,900 Sq Ft

  11 Merriewold Ln N, Monroe, NY 10950

  Discover this beautiful colonial in the sought-after Merriewold section of the Village of South Blooming Grove. With 5 bedrooms and 2 bathrooms, this home offers plenty of space for a growing family. The spacious interior features a kitchen breakfast bar, a formal dining room, and an inviting living area. The level, private lot offers plenty of room for outdoor activities. The backyard is

  Shalom Landau eRealty Advisors, Inc

  11 Merriewold Ln N, Monroe, NY 10950
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  /47

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft

  5 Loch Invar Ln, Middletown, NY 10941

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  Kristine Many Keller Williams Realty

  5 Loch Invar Ln, Middletown, NY 10941
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  /36

  $975,000

  • 4 Beds
  • 3.5 Baths
  • 3,870 Sq Ft

  30 Somerset Ln, Warwick, NY 10990

  Welcome to an extraordinary estate in the prestigious Southwycke Farms, an exclusive, tree-lined enclave of just 36 homes located minutes from the charm and vibrancy of downtown Warwick. Offered for the first time by its original owners, this distinguished residence is a masterclass in timeless elegance, thoughtful design, and meticulous craftsmanship. A grand two-story foyer with a chandelier

  Lisa Holmes Keller Williams Village Sq Rlt

  30 Somerset Ln, Warwick, NY 10990
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  /47

  $169,548 Open Thu 11AM - 4PM

  • 2 Beds
  • 1 Bath
  • 400 Sq Ft

  197 Wheeler Rd Unit 101, Florida, NY 10921

  Mountain Cottages at Serenity Ridge Mountain Club may not be used as a primary residence and are intended only as second homes within a seasonal resort community. Serenity Ridge Mountain Club is Your Home Away from Home. Where Life Slows Down Enough for Joy to Catch Up. Mountain Cottages start at $169,548, and with a monthly $595 membership fee, you can stay for nearly 7 months per year, giving

  Vanessa Wight BHG Real Estate Green Team

  197 Wheeler Rd Unit 101, Florida, NY 10921
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  /27

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,817 Sq Ft

  3105 Betsy Ross Ridge, New Windsor, NY 12553

  THE RESERVES! Cornwall School District! Welcome to this Mount Aire Estates colonial nestled within the highly desirable and prestigious Reserves community. New construction build in 2017 with almost 2,000 sq ft of living space plus full basement with potential to finish for additional living! Lush grounds and mountain views surround this .37 acre property with undeveloped land bordering providing

  Lillian Chase Christie's Int. Real Estate

  3105 Betsy Ross Ridge, New Windsor, NY 12553
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  /28

  $684,500

  • 4 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  13 Hopkins Ct, Washingtonville, NY 10992

  Property back on market due to buyer's financing falling through. Located in the desirable Highgrove community in Washingtonville, this stunning colonial sits on a premium tree-lined homesite with sun-drenched rooms throughout. Its southern exposure fills every space with beautiful natural light and the open floor plan offers a seamless flow, ideal for both everyday living and entertaining.

  TINA TOWNSEND BHHS Hudson Valley Properties

  13 Hopkins Ct, Washingtonville, NY 10992
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  /31

  $658,000

  • 4 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  7 Valley Ct, Florida, NY 10921

  Pristine colonial located on quiet cul-de-sac. There is plenty of room for guests with four spacious bedrooms, two full bathrooms, and a half bath. It features a lovely eat-in kitchen, formal dining room, inviting entrance foyer, and open kitchen with pantry. The living areas are accentuated by rich hardwood flooring throughout. Enjoy the ambiance of gas fireplace during the winter months and

  Rosy Wansor Wansor Realty

  7 Valley Ct, Florida, NY 10921

Showing Results 81 - 120, Page 3 of 4