Orange County NY Homes for Sale with Private Pool

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  $689,000

  • 3 Beds
  • 3 Baths
  • 3,020 Sq Ft

  45 Seminole Dr, Warwick, NY 10990

  Welcome to your private Warwick retreat nestled on 5.5 scenic acres — a rare offering combining refined comfort with unmatched outdoor living and entertaining amenities. This expansive 3-bedroom, 3-bath ranch boasts over 3,000 square feet of open-concept living, designed with both relaxation and celebration in mind. Step inside to an open, flowing floor plan that effortlessly connects the living,

  Arya Rabinovits eRealty Advisors, Inc

  45 Seminole Dr, Warwick, NY 10990
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  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,567 Sq Ft

  11 Pennsylvania Ave, Monroe, NY 10950

  Bright and spacious home located in the Village of South Blooming Grove. Features a light-filled living room, an oversized kitchen with dual sinks and a peninsula, and a dining room with sliders leading to a multi-tier deck and above-ground pool. The primary bedroom includes two closets and a private bath, accompanied by two additional bedrooms and a hall bath. The lower level offers multiple

  Lazar Schvimmer Blooming Realty

  11 Pennsylvania Ave, Monroe, NY 10950
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  $225,900

  • 2 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  15 Redwood Dr, Highland Mills, NY 10930

  Step into this inviting home, where the open-concept main level creates the perfect setting for both everyday living and entertaining. The living room with fireplace, dining area, and kitchen flow seamlessly together, with sliding doors opening to your balcony—ideal for morning coffee or evening relaxation. A convenient half bath and storage complete the first floor. Upstairs, you’ll find two

  Desiree Beecham River Realty Services, Inc.

  15 Redwood Dr, Highland Mills, NY 10930
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  $905,000

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

  9 Roselawn Rd, Highland Mills, NY 10930

  EXQUISITE home has a feature list that is three pages long!The decorator touches, the elegance and sophistication, evident in every room. The foyer welcomes guests with its soaring, vaulted ceiling, large Palladium window, dramatic chandelier, inlaid wood floor with medallion, upgraded staircase, and custom picture moldings! You’ll look forward to retreating to your private sanctuary. The

  Joanne Cooper Hudson Heritage Realty

  9 Roselawn Rd, Highland Mills, NY 10930
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  $1,980,000

  • 5 Beds
  • 4.5 Baths
  • 7,200 Sq Ft

  560 Grand Ave, Newburgh, NY 12550

  Overlooking the Hudson River in the esteemed hamlet of Balmville, The Rest is a rare and remarkable offering—a Gothic Revival masterpiece and enduring symbol of 19th-century architecture, masterfully adapted for modern living.The Rest was designed as both a living work of art and an inviting home and celebrates the ethos of High Victorian Gothic Revival showcasing soaring tracery ceilings,

  Zebee Amy Voss Julia B Fee Sothebys Int. Rlty

  560 Grand Ave, Newburgh, NY 12550
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  $874,400

  • 4 Beds
  • 2 Baths
  • 2,466 Sq Ft

  651 Lakes Rd, Monroe, NY 10950

  Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
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  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,467 Sq Ft

  53 Odyssey Dr, Chester, NY 10918

  Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

  Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
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  $698,000

  • 4 Beds
  • 2 Baths
  • 4,020 Sq Ft

  23 Peach Terrace, Newburgh, NY 12550

  Step inside and feel the sense of space and possibility in this extraordinary 4,000+ sq. ft. contemporary designed for gathering, celebrating, and creating lasting memories. From the moment you enter through the dramatic double doors, you’re welcomed by a sweeping foyer that sets the tone for the grand scale and thoughtful design found throughout. At the heart of the home is a stunning oversized

  Susan Todd BHHS Hudson Valley Properties

  23 Peach Terrace, Newburgh, NY 12550
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  $425,000

  • 3 Beds
  • 2.5 Baths
  • 1,184 Sq Ft

  1065 Dolsontown Rd, Middletown, NY 10940

  Welcome to this private and spacious raised ranch located in the Town of Wawayanda within Middletown School District. Set on 1.5 acres with exceptional privacy, this three-bedroom, 2.5-bath home offers a versatile layout and a convenient location close to everything. The main level features a bright, open floor plan with a combined kitchen, living, and dining area, ideal for everyday living and

  Susan Giordano John J Lease REALTORS Inc

  1065 Dolsontown Rd, Middletown, NY 10940
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  $479,999

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  1210 Hawthorn Way, New Windsor, NY 12553

  Just turn the key and move right into this meticulously maintained 3 bedroom 2.5 bath home at The Grove. 1 Year home warranty included! This elegant & bright home offers sophisticated living with features such as hardwood floors and central A/C. Featuring an enormous eat-in kitchen which is a chef's dream. It's equipped with stainless steel appliances, which include a new LG fridge 1/2026,

  Elsie Nunez Keller Williams Realty

  1210 Hawthorn Way, New Windsor, NY 12553
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  $625,000

  • 2 Beds
  • 3 Baths
  • 2,975 Sq Ft

  24 Juniper Cir, Middletown, NY 10940

  WELCOME TO WILDFLOWER AT WALLKILL — Orange County's premier 55+ Community! This elegant Tarrington model offers nearly 3,000 square feet of beautifully designed living space, combining comfort, sophistication, and convenience. Inside, you’ll find an open dining and living room combination creates the perfect flow for gatherings, while the expansive kitchen and family room with cathedral ceilings

  Patricia Sassi RE/MAX Benchmark Realty Group

  24 Juniper Cir, Middletown, NY 10940
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  $875,000

  • 5 Beds
  • 4 Baths
  • 3,103 Sq Ft

  4 Makan Rd, Monroe, NY 10950

  Ridgetop Estates, Monroe NY, Features 5 Bedrooms • 4 Full Bathrooms • Mountain Views and Room for Expansion. Set on a gently elevated homesite gives way for sweeping views of the neighboring countryside. Your new sun-filled home delivers the space, flexibility, and comfort today’s buyers want. The main level blends comfortable gathering spaces with an easy flow: a gracious living room, a formal

  Chris Carbone HomeSmart Homes & Estates

  4 Makan Rd, Monroe, NY 10950
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  $489,900

  • 3 Beds
  • 2.5 Baths
  • 1,827 Sq Ft

  15 Lindentree Ln, Middletown, NY 10940

  Almost new Townhome in Maples Field is waiting for you! Welcome to our Spacious 3 bedroom, 2.5 bathroom home with 3 levels of space! Enter the open floor plan with hardwood flooring, sun filled living room and dining area. The kitchen features oversized cabinetry with granite countertops, stainless steel appliances and a center island that is perfect for entertaining! Step onto the lovely patio

  Regina Clark Real Estate Circuit Inc

  15 Lindentree Ln, Middletown, NY 10940
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  $169,000 Open Fri 11AM - 4PM

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  197 Wheeler Rd Unit 91, Florida, NY 10921

  Serenity Ridge Mountain Club is Your Home Away from Home...Where Life Slows Down Enough for Joy to Catch Up. Embrace the best of the outdoors without giving up the comforts you love. Serenity Ridge blends nature, recreation, and relaxation into one unforgettable escape. At Serenity Ridge, your Mountain Cottage is designed for seasonal enjoyment—including The Appalachian model, which features 1

  Vanessa Wight BHG Real Estate Green Team

  197 Wheeler Rd Unit 91, Florida, NY 10921
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  $174,777 Open Fri 11AM - 4PM

  • 1 Bed
  • 1.5 Baths
  • 400 Sq Ft

  197 Wheeler Rd Unit 90, Florida, NY 10921

  Serenity Ridge Mountain Club is Your Home Away from Home...Where Life Slows Down Enough for Joy to Catch Up. Embrace the best of the outdoors without giving up the comforts you love. Serenity Ridge blends nature, recreation, and relaxation into one unforgettable escape. At Serenity Ridge, your Mountain Cottage is designed for seasonal enjoyment—including The Appalachian model, which features 1

  Vanessa Wight BHG Real Estate Green Team

  197 Wheeler Rd Unit 90, Florida, NY 10921
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  $675,000

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

  160 Monahan Rd, Port Jervis, NY 12771

  Welcome to 160 Monahan Road, located in the highly sought after town of Greenville. This beautifully maintained young construction home built in 2018 offers 4 bedrooms, 2.5 bathrooms, generous closet space, and a spacious two car garage. As you step inside, you are greeted by an impressive entry foyer that instantly makes you feel at home. The first floor features a versatile entertainment room

  Alexander Fayn Prominent Properties Sotheby's

  160 Monahan Rd, Port Jervis, NY 12771
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  $799,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,525 Sq Ft

  1 Fox Rd, Florida, NY 10921

  A rare and distinguished offering in a coveted neighborhood—available for the first time from its original owners.Meticulously maintained and thoughtfully enhanced, this one-owner Contemporary Colonial reflects enduring quality, architectural grace, and an unmistakable pride of ownership. Homes of this caliber and provenance are seldom offered, making this an exceptional opportunity for the

  Jackie Siracuse Absolute Real Estate of NY Inc

  1 Fox Rd, Florida, NY 10921
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  $2,800,000

  • 4 Beds
  • 5.5 Baths
  • 3,564 Sq Ft

  211 Little York Rd, Warwick, NY 10990

  A Modern Sanctuary of Glass, Light & Landscape – Minutes from Warwick Village Completed in 2025 and sculpted into a landscape of dramatic natural rock formations, this architecturally significant modern residence offers the rare experience of total privacy paired with refined, design-forward living. Every element of this 3,564 sq ft home has been curated to deliver serenity, sophistication, and

  John Ruggieri BHHS Hudson Valley Properties

  211 Little York Rd, Warwick, NY 10990
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  $499,999

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

  130 Spring St, Goshen, NY 10924

  Welcome home to this spacious and inviting 4-bedroom, 2-bath high ranch, perfectly set on a level lot in the heart of the scenic Hudson Valley. From the moment you arrive, the home’s bright and airy atmosphere draws you in, offering a seamless blend of comfort, functionality, and timeless appeal. The upper level showcases an open-concept design where the sun-filled living room flows effortlessly

  Zachary Lisella Coldwell Banker Realty

  130 Spring St, Goshen, NY 10924
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  $750,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,053 Sq Ft

  28 Madison Ct, Wallkill, NY 12589

  Welcome to 28 Madison Court! This stunning, turn-key Colonial is perfectly situated on a quiet cul-de-sac in the desirable Town of Newburgh, with Wallkill Schools. Offering 4 spacious bedrooms and 2.5 baths, this beautifully maintained home combines timeless charm with modern comfort. From the moment you arrive, you’ll be captivated by the exceptional curb appeal, manicured lawn, mature

  Suzanne Hallisey RE/MAX Benchmark Realty Group

  28 Madison Ct, Wallkill, NY 12589
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  $375,000

  • 4 Beds
  • 3.5 Baths
  • 3,658 Sq Ft

  102 W Wiley St, Maybrook, NY 12543

  We are proud to offer an amazing opportunity to restore the historic 1912 Colonial located at 102 W Wiley Street in Maybrook. This remarkable home, built entirely from redwood shipped from the West Coast, boasts incredible structural integrity and timeless architectural details. The house features 4 bedrooms, 4 bathrooms, and a total of 12 rooms. One section of the house was formerly used as a

  Aron Ungar eRealty Advisors, Inc

  102 W Wiley St, Maybrook, NY 12543
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  $639,900

  • 4 Beds
  • 2.5 Baths
  • 3,715 Sq Ft

  216 Maple Ave, Monroe, NY 10950

  Welcome to Your Private Oasis in Monroe!Prepare to be captivated by this stunning 4+bedroom, 2.5-bath residence, perfectly situated on a quiet cul-de-sac in the highly desirable Round Lake community. This 3,700+ sq ft "masterpiece" is an entertainer's paradise.From the sun-drenched formal rooms to the chef-ready eat-in kitchen with its stylish granite island, every space flows seamlessly.

  Chris Scibelli Keller Williams Realty

  216 Maple Ave, Monroe, NY 10950
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  $1,395,000

  • 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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  $799,999

  • 4 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  5 Deangelis Dr, Monroe, NY 10950

  Welcome to this beautifully maintained four-bedroom, two-and-a-half-bath home in the highly coveted Briar Cliff Estates. Offering approximately 2,162 square feet of thoughtfully designed living space, this property combines comfort, style, and functionality in one inviting package. Step into an open layout ideal for gatherings and cozy evenings alike. The spacious primary bedroom provides a quiet

  Joel Ayala HomeSmart Homes & Estates

  5 Deangelis Dr, Monroe, NY 10950
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  $675,000

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

  9 Chestnut St, Greenwood Lake, NY 10925

  TREMENDOUS OPPORTUNITY to own 2 beautiful homes in a lovely lake community for the price of one! That’s 2 houses, 2 separate tax ID’s, and 1 deed. Live in one, rent the other and enjoy tax-free living, or enjoy two separate income streams by renting out both homes! Perfect as Mother/Daughter living situation with two separate houses on same property, or cottage could serve as private guest

  Vincent McAteer Terrie OConnor

  9 Chestnut St, Greenwood Lake, NY 10925
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  $519,000

  • 3 Beds
  • 2 Baths
  • 1,790 Sq Ft

  3 Garden Dr, New Windsor, NY 12553

  Welcome to this beautifully renovated, move-in-ready 3 bedroom, 2-bath home in New Windsor, offering modern comfort, stylish finishes, and exceptional indoor-outdoor living. Completely gutted and rebuilt in 2021 by a professional contractor, all major systems and aesthetics have been fully updated for peace of mind. The open, bright layout features a brand-new kitchen (2021), renovated bathrooms,

  Chand Kakar Howard Hanna Rand Realty

  3 Garden Dr, New Windsor, NY 12553
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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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  $799,000

  • 4 Beds
  • 3.5 Baths
  • 4,299 Sq Ft

  115 Moffat Rd, Washingtonville, NY 10992

  Welcome to this elegant contemporary colonial home, perfectly blending a relaxed atmosphere with luxurious details across 3.1 professionally landscaped acres. Step inside and make a grand entrance through the dramatic foyer, featuring stunning in-lay hardwood floors and stately columns. The expansive living room offers a sophisticated formal space for traditional furnishings and elegant

  Donna Gennaro Howard Hanna Rand Realty

  115 Moffat Rd, Washingtonville, NY 10992
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  $1,350,000

  • 5 Beds
  • 4.5 Baths
  • 5,799 Sq Ft

  60 Cronomer Hts Dr, Newburgh, NY 12550

  Introducing a striking architectural masterpiece nestled on nearly two acres of serene landscape, this exceptional home is defined by luxury, generous scale, and thoughtful design. Offering 5,800 square feet of refined living space, the five-bedroom, four-and-a-half-bath residence presents a rare combination of architectural presence, modern comfort, and an elevated Hudson Valley setting with

  Emily Zambetti Weichert Realtors

  60 Cronomer Hts Dr, Newburgh, NY 12550
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  $539,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  2 Split Tree Dr, New Windsor, NY 12553

  Stunning Corner-Lot with Inground Pool & Prime Commuter Access! Welcome to this beautiful 4 bedroom, 2 and a half bath split level home perfectly situated on a picturesque corner lot with magnificent landscaping and exceptional outdoor living. Designed for both comfort and entertaining, the property features a sparkling inground pool, expansive patio, and lush, professionally maintained grounds

  Jodi Visconti Howard Hanna Rand Realty

  2 Split Tree Dr, New Windsor, NY 12553
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  $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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  $549,900

  • 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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  $625,000

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft

  46 Moulton Cir, Monroe, NY 10950

  Don’t miss out on this opportunity to own your dream home in the desired Monroe-Woodbury school district. Nesting on .26 acres, spanning an impressive 2,270 square feet, and locating only 5 minutes away from downtown Monroe, this home features a thoughtfully designed layout with 9 spacious rooms, making it a private sanctuary like no other. As you step inside, you’ll be greeted by a bright and an

  Louis Octobre Weichert Realtors

  46 Moulton Cir, Monroe, NY 10950
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  $1,875,000

  • 4 Beds
  • 4.5 Baths
  • 5,574 Sq Ft

  14 Stonewall Ct, Warwick, NY 10990

  Bellefontaine — A Lakefront Estate of Exceptional Privacy and Luxury. Privately set behind wrought-iron gates on 12.3 acres in Warwick, this custom Arts & Crafts Colonial offers refined living in a rare lakefront setting. A long paver driveway and triple-waterfall fountain create an impressive arrival. Built in 2005 and thoughtfully updated, the home features ten-foot ceilings, oversized windows,

  Elizabeth Broderick Tuxedo Hudson Realty Corp

  14 Stonewall Ct, Warwick, NY 10990
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  $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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  $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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  $625,000

  • 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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  $605,000 Open Sat 12PM - 2PM

  • 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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  $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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  /11

  $999,999

  • 6 Beds
  • 3 Baths
  • 2,350 Sq Ft

  15 Duelk Ave, Monroe, NY 10950

  15 Duelk Ave, Monroe, NY — Enjoy a refreshing lifestyle with your own swimming pool at this charming single-family home. Offering 6 bedrooms and 3 bathrooms, this property features a finished basement, an attached garage, and a spacious yard perfect for gatherings and relaxation. Nestled in a quiet residential neighborhood and conveniently close to schools, shopping, and local amenities—this is a

  Chaim Reich eRealty Advisors, Inc

  15 Duelk Ave, Monroe, NY 10950

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