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Southfields, NY Homes for Sale with Pool

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  • /32

    $1,700,000

    $188K PRICE DROP
    • 5 Beds
    • 9 Baths
    • 7,794 Sq Ft

    3 Bristol Dr, Middletown, NY 10941

    PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING.....HURRY UP....WILL NOT LAST.............................Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 8.55-bathroom residence features

    Agent Photo

    Mohamed Elgoarany

    All American Realty Management

    (329) 215-0309

    3 Bristol Dr, Middletown, NY 10941
  • /48

    $1,680,000

    $810K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,450 Sq Ft

    395 Sarah Wells Trail, Goshen, NY 10924

    Welcome to Twin Oaks – A Masterfully Restored Hudson Valley Estate.Nestled along one of the most scenic and desirable roads in the Hudson Valley, Twin Oaks is a truly exceptional residence, offering a rare blend of historic grandeur and modern refinement. Set on a tranquil, park-like 8.2-acre estate at the edge of the charming Village of Goshen, this stately French Second Empire Late

    Agent Photo

    Joseph Paoli

    Howard Hanna Rand Realty

    (845) 400-8382

    395 Sarah Wells Trail, Goshen, NY 10924
  • /19

    $285,000

    • 2 Beds
    • 1 Bath
    • 1,020 Sq Ft

    59 Country Club Dr, Florida, NY 10921

    Welcome to this inviting home in the charming Village of Florida. Newly updated flooring and a freshly painted living room create a bright, refreshed atmosphere that’s ready to enjoy from day one.Set within a desirable community, residents have access to an impressive array of amenities designed for both relaxation and recreation, including a pool, hot tub, clubhouse, fitness center, sauna,

    Agent Photo

    Luanne McGann

    Century 21 Full Service Realty

    (845) 614-9302

    59 Country Club Dr, Florida, NY 10921
  • /2

    $425,000

    Open Sun 12PM - 2PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2722 Whispering Hills Unit 542, Chester, NY 10918

    New beginnings offered in this light and bright completely updated end unit featuring two car garage, brand new floors, freshly painted, update kitchen with new stainless steel appliances and so much more. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Low taxes! Town and County, $1,110.66, Village

    Agent Photo

    Erin Connolly-Frontino

    Artisan Realty

    (845) 932-1237

    2722 Whispering Hills Unit 542, Chester, NY 10918
  • /50

    $1,450,000

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    106 Post Rd, Slate Hill, NY 10973

    A Private Mini-Estate of Architectural Distinction in the Goshen School District. Set within the quiet preserve of over 10 acres of wooded grounds, this fully renovated architectural geodesic dome residence—known locally as The Wooden Igloo—offers a rare opportunity to own a true mini-estate that blends iconic design, modern luxury, and exceptional flexibility. Thoughtfully reimagined from top to

    Agent Photo

    Joseph Frullaney

    Real Broker NY LLC

    (845) 460-1149

    106 Post Rd, Slate Hill, NY 10973
  • /47

    $1,750,000

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    106 Post Rd, Slate Hill, NY 10973

    A Private Mini-Estate of Architectural Distinction in the Goshen School District. Set within the quiet preserve of over 17 acres of wooded grounds, this fully renovated architectural geodesic dome residence—known locally as The Wooden Igloo—offers a rare opportunity to own a true mini-estate that blends iconic design, modern luxury, and exceptional flexibility. Thoughtfully reimagined from top to

    Agent Photo

    Joseph Frullaney

    Real Broker NY LLC

    (845) 415-1709

    106 Post Rd, Slate Hill, NY 10973
  • /33

    $999,000

    • 5 Beds
    • 2 Baths
    • 3,012 Sq Ft

    324 Sarah Wells Trail, Goshen, NY 10924

    Step into history with this rare opportunity on Goshen's prestigious Sarah Wells Trail. This property blends historic charm with endless potential. Featuring multiple classic farm structures including a gorgeous old barn & chicken coop along with other outbuildings. The estate is ideal for buyers looking to restore and modernize. The property offers space for horses, smaller livestock and the

    Patricia Caplicki Keller Williams Realty

    324 Sarah Wells Trail, Goshen, NY 10924
  • /50

    $1,195,000

    • 9 Beds
    • 6.5 Baths
    • 4,965 Sq Ft

    19 High St, Chester, NY 10918

    Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

    Beth Palma Keller Williams Realty

    19 High St, Chester, NY 10918
  • /48

    $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
  • /39

    $918,888

    $176K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,600 Sq Ft

    14 Robalene Dr, Goshen, NY 10924

    “Why wait to build? This 6-years-young Colonial is loaded with $400K+ in upgrades and move-in ready with every high-end feature already done.” Better-than-new 6BR/4BA home offering true resort-style living. Stunning gourmet kitchen with granite countertops, stainless steel appliances, hardwood floors, and cozy fireplace. Main level features formal dining and a versatile flex room ideal as a den,

    David White Owner Entry.com

    14 Robalene Dr, Goshen, NY 10924
  • /49

    $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
  • /50

    $799,900

    Open Sat 10AM - 11:30PM
    • 4 Beds
    • 3 Baths
    • 2,904 Sq Ft

    6 Cara Ct, Goshen, NY 10924

    Lovingly maintained colonial sits back from the quiet executive cul de sac. Beautiful paver walk way leads you to the full front porch with gazebo of this classic center hall colonial with convenient updates and touches. Formal living and dining room both have bay windows. Large family room with gas fireplace is open to the updated kitchen with 5 burner gas stove, Bosch dishwasher, and stainless

    Kimberly Corkum Keller Williams Realty

    6 Cara Ct, Goshen, NY 10924
  • /36

    $1,300,000

    $302K PRICE INCREASE
    • 5 Beds
    • 5 Baths
    • 3,130 Sq Ft

    30 Werner Ave Unit MAIN HOUSE, Florida, NY 10921

    This is the ULTIMATE OPPORTUNITY to own an INCOME PRODUCING PROPERTY and live in a LUXURIOUS HOME with an open, flowing floor plan with plenty of private living spaces for multigenerational living, flexible entertaining or home office spaces with the added BONUS of a legal 1 bedroom cottage which currently rents for $1700.00 a month to cover your taxes on this GRAND ESTATE.The 1st floor of the

    Patricia Brady Keller Williams Realty

    30 Werner Ave Unit MAIN HOUSE, Florida, NY 10921
  • /21

    $485,000

    • 2 Beds
    • 2.5 Baths
    • 2,084 Sq Ft

    1 High Ridge Ln, Middletown, NY 10940

    Welcome to refined, low maintenance living in one of Middletown’s most sought after gated communities. This beautifully maintained end unit townhouse offers the perfect balance of space, comfort, and convenience, with over 2,000 square feet of living space designed for today’s lifestyle. Step inside to find a bright and inviting layout featuring two spacious bedrooms, each with generous closet

    Jason Madison eXp Realty

    1 High Ridge Ln, Middletown, NY 10940
  • /40

    $2,495,000

    • 10 Beds
    • 5.5 Baths
    • 6,090 Sq Ft

    157 Arcadia Rd, Goshen, NY 10924

    Welcome to a hidden Hudson Valley gem—an exceptional 9,100+ sq ft grand country estate set on 5 private acres, just 55 minutes from New York City. The charm and character of this unique property are difficult to fully capture in photographs; you must experience it in person to truly appreciate it. Homes like this, especially at this price point, rarely become available. Originally built in 1907,

    James LaTempa Compass Greater NY, LLC

    157 Arcadia Rd, Goshen, NY 10924
  • /40

    $474,999

    • 3 Beds
    • 2.5 Baths
    • 2,055 Sq Ft

    12 Weather Vane Way, Middletown, NY 10940

    Nestled in the Rolling Meadows residential community in the Middletown School District, this 3-bedroom, 2.5-bathroom raised ranch bilevel home seamlessly blends absolute convenience with comfortable community living. The location is truly key, positioned just off East Main Street for incredibly quick access to major highways like Interstate 84 and Route 17, placing you less than 10 minutes from

    Ray Reyes Keller Williams Realty

    12 Weather Vane Way, Middletown, NY 10940
  • /48

    $749,000

    • 5 Beds
    • 5 Baths
    • 3,152 Sq Ft

    42 Parkway, Goshen, NY 10924

    Welcome to 42 Parkway, a Village Beauty overlooking the beautiful Goshen Historic Track. This Classic Colonial features 5 Bedrooms, 5 Baths and a totally private backyard Oasis! As you enter this stunning home, you are greeted by a large Living/Dining Room space with custom storage cabinets, gas fireplace, large windows and gleaming hardwood floors. The updated Kitchen features white cabinets,

    Eveline White Hudson Valley Griffith

    42 Parkway, Goshen, NY 10924
  • /50

    $4,499,000

    $1K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 3,762 Sq Ft

    349 Sarah Wells Trail, Goshen, NY 10924

    The nicest Equine Boarding Facility in Orange County could be yours; located on 103+ Acres with ample privacy, multiple residential houses, 3 separate Garages, a 100' By 200' Indoor Steel Equestrian Riding Arena and 30-Stall Double-Breezeway Horse Barn. The State of the art Horse Barn features a heated riders lounge, tack room and full hayloft. Horse owners know what a flex 14' by 14' horse

    Deb Cor Exclusively Equine Prop LLC

    349 Sarah Wells Trail, Goshen, NY 10924
  • /46

    $845,000

    • 4 Beds
    • 2.5 Baths
    • 2,392 Sq Ft

    77 Houston Rd, Goshen, NY 10924

    Nestled amid the rolling landscapes of Goshen, New York, 77 Houston Road offers a graceful blend of modern elegance and serene country living. This beautifully appointed colonial home sits proudly on a pristine 4.3 acre lot of manicured lawn. Its classic front porch welcoming you with timeless charm and tranquil views. Step inside to discover an open-concept living space featuring a spacious

    Rafael Luciano Luciano Rios Property Grp, Inc

    77 Houston Rd, Goshen, NY 10924
  • /46

    $849,990

    • 4 Beds
    • 2.5 Baths
    • 2,941 Sq Ft

    18 Valley View Rd, Goshen, NY 10924

    Welcome to 18 Valley View Road in Goshen, New York — a meticulously maintained 4-bedroom home set on 1.6 private acres in the highly desirable Remington Ridge Estates and Goshen School District. From the moment you arrive, you’ll appreciate the pride of ownership and exceptional curb appeal this property offers. Step inside to a dramatic two-story foyer that creates an impressive first impression

    Joseph Gorman BHG Real Estate Green Team

    18 Valley View Rd, Goshen, NY 10924
  • /26

    $479,900

    • 2 Beds
    • 2.5 Baths
    • 1,762 Sq Ft

    15 High Ridge Ln, Middletown, NY 10940

    Welcome to this impeccably maintained center-unit townhouse in the desirable Fairways at Wallkill, a gated community known for its convenience and low-maintenance lifestyle. This two-bedroom, two-full bath and one-half bath home offers a clean, modern interior with nothing to update. The main level features an open layout with gleaming hardwood floors, neutral tones, and abundant natural light

    Patricia Sassi RE/MAX Benchmark Realty Group

    15 High Ridge Ln, Middletown, NY 10940
  • /38

    $174,777

    $5K PRICE INCREASE
    • 1 Bed
    • 1.5 Baths
    • 400 Sq Ft

    197 Wheeler Rd Unit 90, 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 $174,777, 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 90, Florida, NY 10921
  • /24

    $318,980

    • 3 Beds
    • 2.5 Baths
    • 800 Sq Ft

    197 Wheeler Rd Unit 92 and 93, 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 $318,980, and with a monthly $995 membership fee, you can stay for nearly 7 months per year, giving

    Vanessa Wight BHG Real Estate Green Team

    197 Wheeler Rd Unit 92 and 93, Florida, NY 10921
  • /47

    $465,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 2,055 Sq Ft

    122 Rolling Meadows Rd, Middletown, NY 10940

    Welcome to your dream home in the heart of Middletown, NY! This beautifully maintained 4 bedroom, 2 bathroom home with a bonus room/home office offers the perfect blend of comfort, convenience, and lifestyle. Nestled in a quiet neighborhood, this spacious property is ideal for today’s modern living with flexible space for working from home, entertaining guests, or simply relaxing in style. The

    Kristine Many Keller Williams Realty

    122 Rolling Meadows Rd, Middletown, NY 10940
  • /33

    $260,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    1401 Whispering Hills, Chester, NY 10918

    Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

    Debbie Goldstein Howard Hanna Rand Realty

    1401 Whispering Hills, Chester, NY 10918
  • /36

    $2,320,000

    • 6 Beds
    • 3 Baths
    • 4,256 Sq Ft

    32 Old Chester Rd, Goshen, NY 10924

    Rare Treasure! Incomparable, private, extraordinary, 46+ acre mini estate. 14 room, 6 bedroom, 3 bath colonial with panoramic vistas, 2 stocked ponds, 5 stall barn with water and electric, guest cottage with a professional kitchen, paddocks, run in sheds, wine cellar, in ground salt water pool & cabana with lav., basketball & pickleball, trails, fields, nature, trees, wildlife and much more. Just

    Marion Bruhns Howard Hanna Rand Realty

    32 Old Chester Rd, Goshen, NY 10924
  • /48

    $447,000

    • 4 Beds
    • 2.5 Baths
    • 2,155 Sq Ft

    126 Rolling Meadows Rd, Middletown, NY 10940

    Original owner has loved this ‘must see’ raised ranch in the Meadows for over 45 years, but it is time for someone new to start making memories! Enter into a light-filled interior where hardwood floors run throughout the main floor and the open floor plan invites entertaining. Beautifully renovated kitchen boasts center island for dining, rich wood cabinets, granite countertops, stainless steel

    Laurel Lustgarten Howard Hanna Rand Realty

    126 Rolling Meadows Rd, Middletown, NY 10940
  • /32

    $319,900

    $4K PRICE INCREASE
    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    2820 Whispering Hills, Chester, NY 10918

    Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

    Anne Marie Scouarnec R2M Realty Inc.

    2820 Whispering Hills, Chester, NY 10918
  • /4

    $470,000

    • 3 Beds
    • 2.5 Baths
    • 1,723 Sq Ft

    22 Atwood Dr, Middletown, NY 10940

    Coming Soon! Beautiful 3 BR, 2.5 baths.

    Kelly Roebuck Curasi Realty, Inc.

    22 Atwood Dr, Middletown, NY 10940
  • /37

    $490,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft

    76 Magnolia Park Rd, Middletown, NY 10940

    Now available in the sought-after Magnolia Park Community. This well-maintained 3-bedroom, 2.5-bath townhouse in the heart of Middletown offers three spacious levels, a sun-filled main floor featuring hardwood floors, an open-concept living and dining area, and a modern kitchen with granite countertops and generous cabinet space. The primary suite boasts a walk-in closet and a luxurious bath with

    Ryan Degnan Howard Hanna Rand Realty

    76 Magnolia Park Rd, Middletown, NY 10940
  • /47

    $169,548

    • 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
  • /23

    $490,000

    • 3 Beds
    • 2.5 Baths
    • 2,191 Sq Ft

    19 Magnolia Park Rd, Middletown, NY 10940

    Welcome to this beautifully maintained newer-construction home in the sought-after Magnolia Park section of the Maple Fields community in Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living with an open-concept layout designed for today’s lifestyle. The main level features a bright and airy living space, a stylish kitchen with granite

    Daniel Amodeo AMO Realty

    19 Magnolia Park Rd, Middletown, NY 10940
  • /32

    $344,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    1311 Whispering Hills Unit 96, Chester, NY 10918

    Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

    Michael Jenney Keller Williams Realty

    1311 Whispering Hills Unit 96, Chester, NY 10918
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