New York Homes for Sale with a Guest House

/77
$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
/64
$399,999
- 4 Beds
- 2 Baths
- 2,400 Sq Ft
252 Main St, Schoharie, NY 12157

Meticulously restored and beautifully upgraded, this exceptional 4 bedroom / 2 bathroom home offers 2400 SF of refined living on a private 1-acre lot in Schoharie. Every feature has been thoughtfully modernized--from a custom kitchen with radiant floors, new insulation, and zoned heating to newer windows, roof, boilers, and refinished hardwoods (and so much more) - all done in the last 13 years!

Alex Cooley Compass Greater NY, LLC

252 Main St, Schoharie, NY 12157
/50
$950,000
- 4 Beds
- 2.5 Baths
- 1,588 Sq Ft
20 Old Mount Kisco Rd, Armonk, NY 10504

Lovely home on over 5 acres on 3 tax lots in the Armonk School District. Great for family or rebuilding into your dream home. Additional 1 bedroom cottage, garage building, and storage building. 3D tour can be viewed at:

Dee Rabady Woodfront Realty, Inc.

20 Old Mount Kisco Rd, Armonk, NY 10504
/47
$4,250,000
- 4 Beds
- 7 Baths
- 5,500 Sq Ft
141A N Ferry Rd, Sag Harbor, NY 11963

Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to

Annmarie Seddio Atlas Sales Realty

141A N Ferry Rd, Sag Harbor, NY 11963
/52
$415,000
- 4 Beds
- 3 Baths
- 1,510 Sq Ft
12295 State Highway 23, Ashland, NY 12407

Welcome to your cozy retreat in the heart of Ashland, NY. Nestled on 1.8 scenic acres between Windham and Hunter Mountains, this inviting property offers two charming homes, stunning mountain views, a tranquil setting surrounded by nature and neighboring horse pastures. The property, known as ''Walnut Grove'', is graced with mature black walnut trees, a prized and increasingly rare hardwood. This

Zachary Palombo Berkshire Hathaway Home Services Blake

12295 State Highway 23, Ashland, NY 12407
/94
$1,695,000
- 8 Beds
- 8 Baths
- 5,118 Sq Ft
1017 Bruyn Turnpike, Wallkill, NY 12589

Welcome to Bruyn Estate, an exceptional Hudson Valley compound that brings together historic character and modern comfort across two remarkable homes: a restored 1835 Greek Revival farmhouse on the National Register of Historic Places, and a reimagined Dog-Trot-style log home built from 1850s barn beams. Set on 8.5 acres, the property is steeped in history: in the 1800s, it was a sheep farm that

Anthony D'Argenzio Houlihan Lawrence

1017 Bruyn Turnpike, Wallkill, NY 12589
/94
$1,695,000
- 8 Beds
- 8 Baths
- 5,118 Sq Ft
1017 Bruyn Turnpike, Pine Bush, NY 12566

Welcome to Bruyn Estate, an exceptional Hudson Valley compound that brings together historic character and modern comfort across two remarkable homes: a lovingly restored 1835 Greek Revival farmhouse on the National Register of Historic Places, and a reimagined log home reconstructed from 1850s barn beams. The property is steeped in history: in the 1800s, it was a sheep farm that supplied wool

Shaina Marron Houlihan Lawrence Inc.

1017 Bruyn Turnpike, Pine Bush, NY 12566
/42
$1,199,000
- 4 Beds
- 2 Baths
- 3,378 Sq Ft
3207-3209 New York 212, Bearsville, NY 12409

Enchanting Woodstock Compound with a Craftsman Home, Cottage, and Historic Barn. Welcome to a truly rare offering in the heart of the Catskills, just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring a

Michelle Bergkamp William Pitt Sothebys Int Rlty

3207-3209 New York 212, Bearsville, NY 12409
/50
$1,500,000
- 3 Beds
- 1.5 Baths
- 2,392 Sq Ft
325 Waterburg Rd, Trumansburg, NY 14886

In the idyllic countryside of upstate New York, just 15 minutes from Cornell University and its world class equine and veterinary centers and 7 miles from Finger Lakes National Forest and 17,000 acres of riding trails, lies a property of rare distinction and opportunity. This 39.3-acre estate combines professional-grade equestrian infrastructure with refined rural living—crafted for those who

Brendan Coughlin Howard Hanna S Tier Inc

325 Waterburg Rd, Trumansburg, NY 14886
/50
$2,450,000
- 5 Beds
- 4.5 Baths
- 4,100 Sq Ft
353 Haas Hill Rd, West Coxsackie, NY 12192

Haas Hill is a rare opportunity to own an expertly envisioned, sprawling country compound on 148 pristine acres amidst the verdant foothills of the Catskill Mountains. The Setting The lush acreage is home to three structures originally built in the late 1940s and all recently renovated: a 2,700 sq ft main house, a two-story cottage with a full bath and kitchenette, and the large pool

Raj Kumar Four Seasons Sotheby's Int.

353 Haas Hill Rd, West Coxsackie, NY 12192
/81
$899,000
- 4 Beds
- 3 Baths
- 2,847 Sq Ft
1187 County Route 31, Granville, NY 12832

The Black Creek Headwaters Farm is 216 acres of picturesque farm and forestland in the Town of Hebron in Washington County. Located on County Route 31, a quiet year-round road, the 1860's farmhouse welcomes you, with views of a beaver pond, hayfields, and rolling hills with ever-changing colors. With its history of outstanding stewardship, natural aesthetic features, and widespread access across

John O'Donnell Timberland Realty

1187 County Route 31, Granville, NY 12832
/47
$3,949,000
- 6 Beds
- 6.5 Baths
- 5,303 Sq Ft
1054 Plandome Rd, Manhasset, NY 11030

Historic Charm Meets Modern Comfort in a Gated Plandome Retreat - Step through the gates of this exceptional property and discover two beautifully restored stone homes. 1054 & 1058 Plandome Rd, originally the carriage and guest houses of the Shore Gables estate on West Drive, now reimagined for modern living with timeless character. The main house welcomes you with a gracious first floor

Kevin Concannon Daniel Gale Sothebys Intl Rlty

1054 Plandome Rd, Manhasset, NY 11030
/35
$79,900
- 3 Beds
- 1 Bath
- 900 Sq Ft
112 Nestle Rd, Fort Plain, NY 13339

Fantastic location at the corner of Rt 163 and Nestle Rd. Just 2 miles from the Village of Fort Plain. Offering 2 acres and artesian well with plenty of water. Property includes well maintain single wide trailer on full foundation with large covered deck and paved driveway. Property owned by the same family for over 70 years. Another old home with some original woodwork with former dance hall in

Rebecca Zarski Howard Hanna Capital Inc

112 Nestle Rd, Fort Plain, NY 13339
/65
$549,000
- 4 Beds
- 3 Baths
- 1,800 Sq Ft
40 Paddock Rd, East Durham, NY 12423

Welcome to The Paddock—a serene East Durham estate where nature, heritage, and creativity converge. This turnkey property, currently a successful Airbnb, offers a peaceful retreat and income opportunity. Set beyond a private gate, it features two renovated homes, a versatile two-story barn, and scenic trails. The main house includes two bedrooms, two baths, a spa-like suite, open kitchen, cozy

John Iconomou Coldwell Banker Village Green

40 Paddock Rd, East Durham, NY 12423
/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
/49
$3,500,000
- 4 Beds
- 4 Baths
- 4,201 Sq Ft
289 Upper Byrdcliffe Rd, Woodstock, NY 12498

Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

289 Upper Byrdcliffe Rd, Woodstock, NY 12498
/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
/50
$1,885,000
- 7 Beds
- 4.5 Baths
- 2,346 Sq Ft
1 Canal Rd, Hampton Bays, NY 11946

This property is a perfect opportunity as a Family Compound or Investment property. Situated on a beautiful lot with water views from every angle is a two story home with a large living room with fireplace, dining area, half bath and kitchen. Two bedrooms on the second floor share a full bath, plus a primary bedroom with full bath and walk-in closet. Off the living room is a large deck perfect

Denise Rosko Hamptons Realty Associates LLC

1 Canal Rd, Hampton Bays, NY 11946
/40
$850,000
- 3 Beds
- 3 Baths
- 1,852 Sq Ft
315 Pine Bush Rd, Stone Ridge, NY 12484

Exceptional 11-acre estate on one of Stone Ridge's most sought-after country roads. This bucolic property features a tranquil pond, lush meadows, and mature trees, offering privacy and scenic views on a picturesque, tree-lined street. Just 5 minutes from Stone Ridge's shops, restaurants, and services, it combines peaceful countryside living with convenient access to amenities. The property

Hayes Clement Compass Greater NY, LLC

315 Pine Bush Rd, Stone Ridge, NY 12484
/47
$3,749,500
- 3 Beds
- 3 Baths
- 2,800 Sq Ft
2 Strongs Ln, Water Mill, NY 11976

Stylish and Secluded Water Mill SanctuaryDiscover this elegant Water Mill summer retreat, perfectly situated in the heart of the Hamptons. Surrounded by meticulously landscaped grounds, the residence offers sunlit interiors, refined yet comfortable living spaces, and a thoughtfully designed layout that seamlessly accommodates both everyday living and entertaining. Outdoors, a private pool is

Jake Kelly Serhant East End LLC

2 Strongs Ln, Water Mill, NY 11976
/33
$629,000
- 4 Beds
- 3 Baths
- 2,455 Sq Ft
446 Shandelee Rd, Livingston Manor, NY 12758

Own a sustainable 13.2-acre compound in Livingston Manor with a fully owned solar system and an estimated annual electric bill of just $200. Experience the rare freedom of a move-in ready home with minimal monthly overhead. This 4-bedroom, 3-bath farmhouse sits on over 13 private acres, offering a diverse mix of flat, usable land near the home and wooded hillsides perfect for trekking and

April DeMaio Keller Williams Hudson Valley

446 Shandelee Rd, Livingston Manor, NY 12758
/49
$3,150,000
- 4 Beds
- 3.5 Baths
- 5,000 Sq Ft
12 Bishop Park Rd, Pound Ridge, NY 10576

Generational Compound with all the luxuries & amenities one desires. Cascading pool with waterfall spa, guest house, pond, gardens and private property. Set down a quiet lane this resort-style estate is prime living-just one hour from NYC. A tranquil place to call home for the discerning buyer who can spot special custom home. A thoughtful and tasteful full renovation was completed in 2013. The

Michael Kaplan Michael J. Kaplan

12 Bishop Park Rd, Pound Ridge, NY 10576
/12
$1,600,000
- Land
- 73 Acres
- $21,918 per Acre
10252 Short Cut Rd, Cato, NY 13033

73 acres of partially developed farmland and 3 large buildings for your generational farming or development opportunity. First time on market in over 60 years. 5 minute drive to NYS Thruway Weedsport Exit. Well established 19 acre turnkey blueberry farm with significant farm equipment and 19,000 blueberry plants. One 8,000sf main building and 2 10,000sf pole barns with 3 phase electric. One pole

Mike Barry Pyramid Brokerage Company - Co

10252 Short Cut Rd, Cato, NY 13033
/35
$2,995,000
- 3 Beds
- 2.5 Baths
- 3,525 Sq Ft
21 Saddle Ln, East Hampton, NY 11937

A rare convergence of art, architecture, and setting, 21 Saddle Lane offers a one-of-a-kind opportunity to own a home deeply rooted in creative history. Once the residence and working studios of noted artists Connie Fox and William King, this property carries forward a legacy of inspiration, thoughtfully reimagined for modern living. Privately set on an acre in the Northwest Woods of East

Bryan Midlam Compass

21 Saddle Ln, East Hampton, NY 11937
/36
$795,000
- 4 Beds
- 2 Baths
- 2,056 Sq Ft
421-423 Hillside Rd, Cragsmoor, NY 12420

This 4-bedroom 2 bath main house, and 3-bedroom 1 bath cottage are located on 4.5 wooded acres with scenic views in the historic artists’ hamlet of Cragsmoor, located on a ridge in the Shawangunk Mountains. The community is encircled by 24,000 acres of lands protected by the Minnewaska State Park Preserve with Sam's Point Preserve minutes from the property. The main house was built in 1907 by the

Carolyn Peters-Baker Keller Williams Hudson Valley

421-423 Hillside Rd, Cragsmoor, NY 12420
/48
$2,999,500
- 4 Beds
- 4 Baths
22 W Gate Rd, Wainscott, NY 11975

Step into this fully renovated 4-bedroom, 4-bathroom home offering over 3,300± sq. ft. of living space on 0.52± acres in the heart of Wainscott. Designed for versatility, the layout includes two primary bedroom suites with walk-in closets-one on the main level and one upstairs-plus additional rooms ideal for a home office, studio, or guest accommodations. An accessory apartment with private

Jake Kelly SERHANT.

22 W Gate Rd, Wainscott, NY 11975
/30
$6,795,000
- 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
/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
/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
/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
/49
$5,499,000
- 6 Beds
- 7.5 Baths
- 4,140 Sq Ft
22 Messenger Ln, Port Washington, NY 11050

Sunset Beach - A Private Coastal Retreat on Long Island Sound. Step from your backyard into the pristine waters of the Sound — where coastal luxury meets everyday living. Welcome to Sunset Beach, an enchanting 10-room brick estate nestled on five private, fully fenced acres along one of Long Island’s most coveted waterfronts. From jet skiing and paddle boarding to horseback riding along the shore

Regina Rogers Douglas Elliman Real Estate

22 Messenger Ln, Port Washington, NY 11050
/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
/42
$825,000
- 3 Beds
- 3 Baths
- 1,236 Sq Ft
166 Todd Hill Rd, West Kill, NY 12492

WHERE ARCHITECTURE MEETS NATURE! A rare underground retreat with walls of glass doors framing breathtaking mountain & valley vistas. Hidden in plain sight, this one-of-a-kind property offers unmatched privacy, modern style, and year-round comfort thanks to its earth-protected design. This is the Trifecta of properties - a stunning private setting, unique architecture, and endless possibilities.

Marcia Weiss Halter Associates Realty

166 Todd Hill Rd, West Kill, NY 12492
/37
$10,900,000
- 13 Beds
- 12.5 Baths
- 8,500 Sq Ft
74 Cedar Ln W, Remsenburg-Speonk, NY 11751

This majestic, one-of-a-kind estate is set on 4+ private, resort-like acres in the Town of Southampton. Its unique location on the southwest-facing waterfront provides incredible sunset views over Seatuck Cove and Moriches Bay from large windows throughout the bright, airy main residence. Perfect for entertaining, the meticulously updated 9-bedroom, 9.5-bath main home features a chef's kitchen

Lauren Spiegel Douglas Elliman Real Estate

74 Cedar Ln W, Remsenburg-Speonk, NY 11751
/64
$12,500,000
- 4 Beds
- 6 Baths
- 6,829 Sq Ft
241 Cunningham Hill Rd, Canaan, NY 12029

A Home like no other. You will simply not find a Property like PIERCE PEAK, anywhere. AIA Award Winning Architectural Design by Burr & Mc Callum, crested upon the summit of Cunningham Hill (site cleared for HELIPAD). Open plan living with Indoor and Outdoor Living Rooms. Gourmet Kitchen, 2 Primary and 2 connnected Loft spaces. 2 Bedroom Guest Quarters (that can sleep 8), and Infinity Pool with

Steven Weisz William Pitt Sothebys Intn'l

241 Cunningham Hill Rd, Canaan, NY 12029
/39
$14,000,000
- 9 Beds
- 9.5 Baths
- 7,000 Sq Ft
401 Lake Delaware Dr, Andes, NY 13731

Built on the edge of a glorious 68 acre lake set in a high mountain valley in the scenic Catskill Mountains, the historic Lake Delaware Farm offers a rare opportunity to acquire a piece of a true American legacy that has been in continuous use by the same notable family since the 18th century. The Lake House, among the oldest buildings standing in Delaware County, offers a glimpse into the

Norah Burden Brown Harris Stevens

401 Lake Delaware Dr, Andes, NY 13731
/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
/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
/36
$949,000
- 4 Beds
- 4 Baths
- 3,900 Sq Ft
3880 County Route 30, Salem, NY 12865

The Ultimate Getaway. The perfect country retreat! Long drive to total privacy. A historical home from the 1700’s, once originally part of a hay farm. Over 50 glorious acres with beautiful open meadows, spring-fed pond, fruit trees and flowering gardens. Unique Post “& Beam Converted Barn, dating to 1763. Remarkable interior spaces with vaulted ceilings, hardwood floors, exposed beams and open

Cristina Civetta Ginnel Real Estate

3880 County Route 30, Salem, NY 12865
/65
$2,599,000
- 6 Beds
- 6 Baths
- 2,832 Sq Ft
844 Hickory Hill Rd, Fort Plain, NY 13339

Legacy meets lifestyle-The Brower Estate spans 136 serene acres at the end of a maple-lined drive offering endless potential as an idyllic residence or coveted event destination. Steeped in history, the English cottage houses traditional wide plank floors, Dutch doors, soapstone sinks, Delft tiles, several fireplaces, and an Aga stove. Additional accommodations extend to the bright 1 bed/1 bath

Ashley Schorpp NY ICON Group LLC

844 Hickory Hill Rd, Fort Plain, NY 13339

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New York Homes for Sale with a Guest House

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