179

New York Homes for Sale with a Guest House

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  • /36

    $579,000

    • 3 Beds
    • 1.5 Baths
    • 1,498 Sq Ft

    861 Snydertown Rd, Craryville, NY 12521

    Country cottage sitting on a 6 acre property with 3 ponds and a large yard surrounded by lilacs. This 3 bedroom, 2 bathroom home offers a country retreat on a quiet road. There are pine floors throughout the home with the washer and dryer hookup in the pantry, light filled sun room and built in pine bookcase. The kitchen is equipped with stainless steel refrigerator, dishwasher, gas range stove

    Joyce Vale Coldwell Banker Advisor Realty

    861 Snydertown Rd, Craryville, NY 12521
  • /33

    $1,495,000

    • 6 Beds
    • 7 Baths
    • 4,592 Sq Ft

    2080 Upper Meeker Hollow Rd, Roxbury, NY 12474

    Founded in 1803 in Roxbury, NY, this remarkable property carries a rich heritage of hospitality — the stone house once served as an Inn for travelers crossing the mountain from Bovina in the 1800s. Today, the estate spans over 200 acres and blends history with breathtaking natural beauty, offering a rare opportunity to own a piece of the Catskills' past.Beautiful views of the mountains,

    Anne Rajs Corcoran Country Living

    2080 Upper Meeker Hollow Rd, Roxbury, NY 12474
  • /33

    $4,995,000

    • 6 Beds
    • 8.5 Baths
    • 4,900 Sq Ft

    161 South Rd, Westhampton, NY 11977

    Stunning New Construction in Westhampton with Rare 2 Story 4 Seasons Guest house on 1.5 Waterfront Acres with Bay Access. A newly constructed masterpiece by esteemed CMT Builders, this nearly 1.5-acre waterfront estate,positioned on the Westhampton Beach Village fringe, sets a new benchmark for modern Hamptons living. Positioned along the peaceful waters of Tanners Neck Creek with distant views

    Robert Canberg Nest Seekers International LLC

    161 South Rd, Westhampton, NY 11977
  • /55

    $539,900

    • 3 Beds
    • 4 Baths
    • 1,872 Sq Ft

    161 Meade Rd, Charlotteville, NY 12036

    Escape to 161 Meade Road—where 15 acres of adventure meet total luxury. This isn't just a home; it's a gateway to the great outdoors. Bordering the serene Charlotte Creek and located just minutes from the 818-acre Clapper Hollow State Forest, your days can be filled with hiking, fishing, and exploring right from your doorstep. The stunning log architecture features a seamless open-concept layout,

    Matthew Loder Country Boy Realty

    161 Meade Rd, Charlotteville, NY 12036
  • /50

    $1,500,000

    • 3 Beds
    • 5.5 Baths
    • 2,331 Sq Ft

    1091 Albany Post Rd, Gardiner, NY 12525

    1091 Albany Post Road is the kind of property people imagine when they dream about the Hudson Valley — expansive skies, river frontage, mountain views, and a home that feels both refined and deeply connected to the land.This offering represents a newly created private estate parcel. The seller will subdivide the original 78.68-acre property to convey the primary residence, a fully finished

    Brandon Mosher

    1091 Albany Post Rd, Gardiner, NY 12525
  • /32

    $3,650,000

    • 4 Beds
    • 3 Baths
    • 2,118 Sq Ft

    15 Finney Farm Rd, Croton On Hudson, NY 10520

    The Volner House is a mid-century modern residence with Hudson River views, locatedapproximately 45 minutes from New York City and indirectly adjacent to the Hudson NationalGolf Course. The property overlooks multiple river bays and offers southern and westernexposures with sunset views.Designed in 1951 by modernist architect H. Seymour Howard Jr., a graduate of

    Dalia Valdes Julia B Fee Sothebys Int. Rlty

    15 Finney Farm Rd, Croton On Hudson, NY 10520
  • /52

    $3,950,000

    • 9 Beds
    • 12 Baths
    • 10,500 Sq Ft

    9 Chambers Rd, West Park, NY 12493

    A great legacy meets true luxury: Hudson Shore Estate, formerly home to one of Eleanor Roosevelt's early passion projects, a pioneering vocational school for women, has now been masterfully restored to its former glory and offers the perfect setting for a multi-generational family compound. A unique example of Arts & Craft design amongst its peer group of renowned Hudson River mansions, the

    Hayes Clement Compass Greater New York, LLC

    9 Chambers Rd, West Park, NY 12493
  • /28

    $984,900

    • 5 Beds
    • 4 Baths
    • 3,001 Sq Ft

    138-140 Church St, Saratoga Springs, Inside, NY 12866

    Just a few blocks from the heart of Broadway, zoned UR3 (see attachments for description of allowed uses) 138-140 Church Street offers a combination of location, space, and flexibility in downtown Saratoga Springs. Behind its unassuming façade is a remarkably spacious property with multiple living areas, private quarters, and extensive parking—ideal for multigenerational living or for an

    Maria Barr Four Seasons Sotheby's International Realty

    138-140 Church St, Saratoga Springs, Inside, NY 12866
  • /37

    $7,488,000 Open Sun 2PM - 3:30PM

    • 9 Beds
    • 12 Baths
    • 17,587 Sq Ft

    60 Piping Rock Rd, Glen Head, NY 11545

    Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless

    Aileen Murstein Compass Greater NY LLC

    60 Piping Rock Rd, Glen Head, NY 11545
  • /46

    $39,000,000

    • 9 Beds
    • 15 Baths
    • 55,000 Sq Ft

    104 N Garden Dr, Pawling, NY 12564

    Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

    Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

    104 N Garden Dr, Pawling, NY 12564
  • /31

    $2,500,000

    • 5 Beds
    • 4.5 Baths
    • 2,978 Sq Ft

    177 Tinker St, Woodstock, NY 12498

    Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

    Joan Capria Four Seasons Sotheby's Int'l R

    177 Tinker St, Woodstock, NY 12498
  • /46

    $9,600,000

    • 6 Beds
    • 5.5 Baths
    • 9,290 Sq Ft

    512 E Shore Rd, Great Neck, NY 11024

    Welcome to an extraordinary opportunity to own a magnificent waterfront estate located in the heart of Kings Point, one of Long Island’s most coveted communities. Set on 1.5 lush, private acres with sweeping views of the Manhasset Bay/Long Island Sound, this contemporary residence offers the ultimate in luxury, comfort, and resort-style living. This expansive home features 6 bedrooms and 5.5

    Soheila Sharf S Sharf Realty Inc

    512 E Shore Rd, Great Neck, NY 11024
  • /26

    $349,999

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft

    166 Old Loudon Rd, Latham, NY 12110

    Currently used as a rental property and leased until Sept 30, 2026. Strong rental history, near bus line, highly visible location for home, or business with ample newly paved parking. A perfect investment property, centrally located near shopping, businesses, banks, conveniences restaurants. This solid home features gorgeous redone hardwood floors, a full bath on each floor, spacious rooms, a

    Joan Wennstrom KW Platform

    166 Old Loudon Rd, Latham, NY 12110
  • /50

    $2,300,000

    • Land
    • 72.06 Acres
    • $31,918 per Acre

    1458 Trumansburg Rd, Ithaca, NY 14850

    Hidden from view, yet just minutes from Cornell University, this gated equestrian estate offers a setting and opportunity unlike any other. Nestled on 72 terraced acres, a tree-lined lane bordered by classic white fencing leads to a premier horse facility that combines lifestyle, business, and beauty in one extraordinary package. Currently home to a thriving boarding operation, this elite center

    Karen Eldredge Howard Hanna S Tier Inc

    1458 Trumansburg Rd, Ithaca, NY 14850
  • /30

    $6,999,000

    • 8 Beds
    • 10 Baths
    • 5,500 Sq Ft

    69 Halsey St, Southampton, NY 11968

    New construction please verify taxes

    Paul Luciano Utopia Real Estate

    69 Halsey St, Southampton, NY 11968
  • /49

    $2,000,000

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

    1202 Jackson Corners Rd, Red Hook, NY 12571

    Welcome to an exceptional waterfront retreat in the heart of Red Hook, where refined design meets effortless lifestyle. Nestled along the serene Roe Jan Kill as it winds through your backyard, this remarkable residence offers picturesque water views and a setting that feels both private and inspiring. Living like a three-bedroom home, the layout is thoughtfully designed with generous proportions,

    Christopher Ferraro RE/MAX Town & Country

    1202 Jackson Corners Rd, Red Hook, NY 12571
  • /44

    $975,000

    • 3 Beds
    • 2.5 Baths
    • 2,965 Sq Ft

    819 Van Wagner Rd, Poughkeepsie, NY 12601

    Fox Ridge Farm. A lovely country home on 9+ bucolic acres, privately situated in beautiful Dutchess County, NY. This listing includes two separate parcels; the house on 7.11 acres on one side of the road and a 2.61 acre parcel with a picturesque pond on the other side. The main house dates back to 1830 and this property has been beautifully maintained and carefully preserved over the years. The

    Susan Whalen George T Whalen Real Estate

    819 Van Wagner Rd, Poughkeepsie, NY 12601
  • /80

    $10,900,000

    • 7 Beds
    • 9 Baths
    • 6,218 Sq Ft

    40 Geyser Rd, Saratoga Springs, NY 12866

    Owned by the iconic Queen of Saratoga, the late Marylou Whitney, & her husband the late John Hendrickson, this 120+ acre property embodies the beauty & history of Saratoga Springs. The mansion has 6218 SF, built in 1851, 7 bedrooms, 7 full baths, 2 1/2 baths, 3 covered porches, pool house w/ heated pool & gym, chapel, tennis courts, rose gardens, 2 bay heated detached garage, 9 bay heated

    Andrea Collins Four Seasons Sotheby's International Realty

    40 Geyser Rd, Saratoga Springs, NY 12866
  • /49

    $1,849,000

    • 7 Beds
    • 3.5 Baths
    • 5,700 Sq Ft

    230 W Islip Rd, West Islip, NY 11795

    Welcome to a piece of Paradise! this beautiful 1928 5,700 sq. ft. Georgian Colonial, features 7 large bedrooms, 3.5 baths, 16 rooms total, located on beautiful Sampums deep water creek, a few hundred yards from the Great South Bay. this lavish estate offers, poly/glass siding with a 50yr warranty, new central air, decks and terrace built with azek decking. All new exterior lighting, completely

    Alice Yurkerwich Howard Hanna Coach

    230 W Islip Rd, West Islip, NY 11795
  • /45

    $3,495,000 Open Sat 1PM - 3PM

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

    43 Hilltop Ln, Thornwood, NY 10594

    Stunning new construction nestled in the highly sought-after Rolling Hills section of Thornwood, this exceptional residence offers refined modern living in one of the area’s most desirable settings. Bathed in natural light, the home showcases designer finishes, custom statement lighting, and thoughtfully curated details throughout. Designed for both everyday comfort and effortless entertaining,

    SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

    43 Hilltop Ln, Thornwood, NY 10594
  • /79

    $570,000

    • 4 Beds
    • 1.5 Baths
    • 2,340 Sq Ft

    176 High Rock Rd, West Coxsackie, NY 12192

    Tucked deep in the woods yet only minutes from major routes, this timeless colonial retreat offers both privacy and possibility. Designed in the style of early American homesteads but built with enduring modern materials, the residence blends history and function with grace. Inside, you'll find craftsmanship rooted in the land itself. The creek stone fireplace was built from stone gathered on the

    Marisa Multari Miranda Real Estate Group Inc

    176 High Rock Rd, West Coxsackie, NY 12192
  • /79

    $3,995,000

    • 6 Beds
    • 4.5 Baths
    • 3,868 Sq Ft

    2988 Lake Shore Dr, Lake George, NY 12845

    Excellent value at this lakefront 5,668 SF, 6 BR, 4.5 bath residence built in 2004 and lightly lived in. The main level features a vaulted great room, lake-facing kitchen/dining wing, and private primary suite with walk-in closets and luxury bath. Upstairs offers 5 BR's (2 w/lakeviews) and 2 baths. Walk-out lower level has open layout w/kitchen and bath - ideal for entertaining. Quality finishes

    Nic Ketter Realize Brokers

    2988 Lake Shore Dr, Lake George, NY 12845
  • /49

    $1,695,000

    • 4 Beds
    • 3.5 Baths
    • 1,702 Sq Ft

    26 S Menantic Rd, Shelter Island, NY 11964

    Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the

    Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

    26 S Menantic Rd, Shelter Island, NY 11964
  • /51

    $5,900,000

    • Land
    • 100.51 Acres
    • $58,701 per Acre

    4317 New York 23, Hudson, NY 12534

    A RARE offering of 100+ acres just minutes from the center of Hudson, NY with Catskill Mountain views and plenty of road frontage for subdividing. The clear upside is that property is in the Town of Greenport which currently does not have a zoning plan in place which allows you to dream big. The property includes a stunning 7 bedroom boutique hotel with magnificent Catskill views which is

    Jennifer Capala William Pitt Sothebys Intn'l

    4317 New York 23, Hudson, NY 12534
  • /49

    $324,900

    • 6 Beds
    • 3 Baths
    • 2,672 Sq Ft

    401 State Route 7, Richmondville, NY 12149

    Excellent income-producing opportunity featuring two separate homes on 3 private acres in Richmondville. With a total of 6 bedrooms and 3 full baths, this versatile property is ideal for owner-occupants, multi-generational living, or rental income. The main residence is a charming 1800s Colonial offering 4 bedrooms and 2 full baths. Bright and spacious, it features beautiful flooring, exposed

    Lynnette Butler Country Boy Realty

    401 State Route 7, Richmondville, NY 12149
  • /38

    $6,295,000

    • 10 Beds
    • 11 Baths
    • 12,800 Sq Ft

    365 Split Rock Rd, Syosset, NY 11791

    Welcome to 365 Split Rock Road...Set within one of the North Shore of Long Island’s most desirable enclaves, this gated estate in Syosset offers an exceptional balance of privacy, scale, and modern design. Recently constructed and thoughtfully sited on five private acres, the residence encompasses over 12,000 square feet of well-proportioned living space, creating a quiet retreat defined by

    Theodosis Neocli Astoria Realty Brokerage Svcs

    365 Split Rock Rd, Syosset, NY 11791
  • /46

    $1,795,000

    • 7 Beds
    • 4.5 Baths
    • 4,802 Sq Ft

    1739 New York 214, Lanesville, NY 12450

    Modern Victorian estate with pool, yoga studio, cottage and mountain access. Escape to the heart of the Catskills with this extraordinary modern Victorian estate, where timeless architectural charm meets contemporary comfort. Nestled on just under 20 acres of meadows and forest, this spacious 7-bedroom, 5.5-bath residence offers the ultimate mountain lifestyle; ideal as a full-time residence,

    Michelle Bergkamp William Pitt Sothebys Int Rlty

    1739 New York 214, Lanesville, NY 12450
  • /40

    $1,395,000

    • 5 Beds
    • 4 Baths
    • 4,512 Sq Ft

    226 County Route 17, Valatie, NY 12184

    Welcome to historic Surdeval Farm, a spacious 4,500 square-foot, five-bedroom, four-bath homestead on 24.5 acres located between the charming villages of Chatham, Kinderhook, and Valatie. Over the decades the original early 1800’s core home was expanded and rearranged and it is now ready for its next chapter. The formal entrance to the home is from the grand tree-lined circular driveway to the

    Peggy Lampman Peggy Lampman

    226 County Route 17, Valatie, NY 12184
  • /45

    $3,250,000

    • 8 Beds
    • 4.5 Baths
    • 3,010 Sq Ft

    2039 Salt Point Turnpike, Salt Point, NY 12578

    Welcome to This Hudson Farm – a distinctive 157+ acre estate spanning 2039–2105 Salt Point Turnpike, where the beauty of the Hudson Valley meets the ultimate opportunity to enjoy as much—or as little—of the farming lifestyle as you desire. Positioned between Rhinebeck and Millbrook, and just minutes from the Taconic State Parkway, this remarkable offering blends historic charm with modern

    Lindsay Rothman Compass Greater NY LLC

    2039 Salt Point Turnpike, Salt Point, NY 12578
  • /22

    $2,100,000

    • Land
    • 70.5 Acres
    • $29,787 per Acre

    243 Vineyard Ave Unit 251, Highland, NY 12528

    Spectacular 70 acre parcel located right outside the village of Highland. May be used as a farm or subdivided. Parcel has 3 rentals located on it in addition to 1 vacant house. Also on this property is a very large steel building with high ceilings and oversized garage doors as well as a barn! Close commuter location - Metro North, NYS Thruway, Mohonk Mountains and Hudson Valley Rail Trail.

    John Quinn Quinn Realty Group Inc.

    243 Vineyard Ave Unit 251, Highland, NY 12528
  • /30

    $680,000

    • 3 Beds
    • 2 Baths
    • 1,619 Sq Ft

    517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516

    Discover 515-517 East Mountain Road North—a turnkey ranch perched atop the mountain, where timeless charm meets contemporary living on over 2 acres. This exceptional home artfully blends old-world details with modern additions, creating a perfect harmony of character and comfort.The main house has been beautifully renovated and expanded, featuring a brand-new 264 sq. ft. addition that

    Natalia Rathbauer Julia B Fee Sothebys Int. Rlty

    517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516
  • /37

    $12,000,000

    • 5 Beds
    • 5.5 Baths
    • 7,538 Sq Ft

    48 Raafenberg Rd, Tarrytown, NY 10591

    Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central

    David Turner Compass Greater NY, LLC

    48 Raafenberg Rd, Tarrytown, NY 10591
  • /49

    $409,000

    • 4 Beds
    • 2 Baths
    • 3,157 Sq Ft

    312 2nd St, Ithaca, NY 14850

    Sun-filled 2,018 SF home has hardwood floors, 3-4 bedrooms, 2 full baths, and 2 kitchens – one on each level. Bright and open first floor kitchen has new granite counters, oak cabinets & new appliances+ laundry/breakfast nook, 1 bedroom, bath and big front porch. Second floor offers a 2nd kitchen/living/dining, 2nd full bath, 2 more bedrooms, upper front porch, and sweet back sunroom (4th BR?),

    Kristin Ahlness Howard Hanna S Tier Inc

    312 2nd St, Ithaca, NY 14850
  • /43

    $12,800,000

    • 10 Beds
    • 15 Baths
    • 20,000 Sq Ft

    53 Simonson Rd, Glen Head, NY 11545

    Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary.A

    Jason Friedman Daniel Gale Sothebys Intl Rlty

    53 Simonson Rd, Glen Head, NY 11545
  • /41

    $550,000

    • 5 Beds
    • 3 Baths
    • 3,200 Sq Ft

    53 W Corbett Rd, Montgomery, NY 12549

    Nestled on a serene hillside, this lovely four story contemporary home offers a perfect balance of modern luxury and natural beauty. Move in worry free as there has just been a full renovation. New roof, new mechanicals, new windows & doors, new fixtures. This unique home is bathed in natural light from large windows that frame views of the nearby mountains & wilderness. Both the walls and the

    Heather Macauley eXp Realty

    53 W Corbett Rd, Montgomery, NY 12549
  • /50

    $1,795,000

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

    53 Old Neck Rd S, Center Moriches, NY 11934

    Experience the ultimate in coastal living with this extraordinary waterfront compound, privately nestled in the sought-after Holiday Beach community. This rare offering features a spacious main residence & a fully renovated guest cottage, perfectly designed for luxurious living and effortless entertaining.The main house welcomes you with a flowing layout that includes a dramatic great room,

    Rachel Hujber Signature Homes of New York

    53 Old Neck Rd S, Center Moriches, NY 11934
  • /41

    $2,049,000

    • 3 Beds
    • 3 Baths
    • 1,923 Sq Ft

    12910 Main Rd, East Marion, NY 11939

    NOW IS THE TIME TO VISIT THIS AMAZING BAYFRONT PROPERTY AND FALL IN LOVE!! Paradise Found on Gardiner’s Bay! This is a rare 2 for 1 opportunity, consisting of a beautiful 2 Bedroom, 2 Bath Bayfront Main House, PLUS a 1 Bedroom, 1 Bath Guest Cottage! The property is fully bulk-headed with approximately 70 feet of serene and captivating beachfront along Gardiner’s Bay, and has undergone recent,

    Richard Connelly Douglas Elliman Real Estate

    12910 Main Rd, East Marion, NY 11939
  • /37

    $1,225,000

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft

    174 County Route 11, Pine Plains, NY 12567

    Expansive 55+ Acre Multi-Home Compound. A rare opportunity to own a one-of-a-kind compound set on 57.44 private, picturesque acres—ideal for multi-generational living or a unique investment. The main residence offers 1,888 square feet of rustic charm and comfort, featuring 4 bedrooms and 2 full baths. Enjoy cozy evenings in the living room with pegged oak floors, pine paneling, and a classic

    Paula Redmond Corcoran Country Living - Mill

    174 County Route 11, Pine Plains, NY 12567
  • /51

    $19,995,000

    • 7 Beds
    • 9 Baths
    • 12,659 Sq Ft

    309 Woodstock Rd, Millbrook, NY 12545

    Presenting Canoe Hill, a remarkable 63-acre estate and vineyard in the heart of Millbrook, New York. This extraordinary property stands as a testament to architectural evolution, where a storied mid-1700s colonial core has been thoughtfully expanded to create a remarkable 12,650 SF main residence that seamlessly marries Colonial, Georgian and Greek Revival influences. Two significant expansions,

    Jason Karadus Corcoran Country Living

    309 Woodstock Rd, Millbrook, NY 12545
  • /41

    $18,995,000

    • 8 Beds
    • 13 Baths
    • 13,481 Sq Ft

    104 Premium Point Rd, New Rochelle, NY 10801

    The Bluffs at Premium Point introduces ultra-luxury living at the absolute pinnacle of the Premium Point market, setting a new standard within Mamaroneck’s most exclusive, guard-gated peninsula. One of only the coveted “Big Four” landmark estates in this 24/7 secured enclave, this brand-new architectural masterpiece occupies a rare 1.3-acre waterfront sanctuary with horizon-level views found

    Wendy Alper Julia B Fee Sothebys Int. Rlty

    104 Premium Point Rd, New Rochelle, NY 10801

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