New York Homes for Sale with a Guest House

/46
$799,900
- 7 Beds
- 5 Baths
- 3,226 Sq Ft
108 Main St, Livingston Manor, NY 12758

Located in one of Sullivan County Catskill's hottest downtowns in the heart of Livingston Manor, this incredible offering is a once in a lifetime opportunity. Two homes, on two lots offer great flexibility for multi-generational living, rental income, or creative restoration. One home was originally a multi-family which can be converted back (kitchens are still intact) and the other is

Carol Malek Malek Properties, Inc.

108 Main St, Livingston Manor, NY 12758
/29
$1,600,000
- 13 Beds
- 13 Baths
- 4,802 Sq Ft
669-671 Broadway Rt 9w, Esopus, NY 12429

Prime Hospitality Investment Opportunity on Mirror Lake - 10-Unit Motel & 2-Family HomeLocated on the banks of Mirror Lake, this 1.2-acre hospitality-zoned property offers a unique investment opportunity just 5 minutes from Downtown Kingston's waterfront and 90 miles from NYC. Formerly operating as the Lake Motel, the property consists of two adjacent parcels: a 10-unit motel and a

Greg Berardi Berardi Realty

669-671 Broadway Rt 9w, Esopus, NY 12429
/17
$349,000
- 2 Beds
- 2 Baths
- 2,205 Sq Ft
7257 New York 52, Greenfield Park, NY 12435

THIS 2.205 SQFT chalet-style building has a desirable Ulster County location. It was originally built as a restaurant, BUT canbe used as a creative space or office. or residential. It hosts a commercial kitchen, two 1/2 baths (Men's & Womans rooms) two large rooms, back deck and pull downstairs to stand up attice, space with flooring, part basement with walk in cooler the property also has a 1987

Jeoffrey Devor BHHS HUDSON VALLEY PROP-NP

7257 New York 52, Greenfield Park, NY 12435
/33
$8,895,000
- 5 Beds
- 10 Baths
- 19,900 Sq Ft
40 Piping Rock Rd, Locust Valley, NY 11560

A Sanctuary of Sophistication, Sustainability And Serenity 40 Piping Rock Road in Matinecock-Tucked behind a gated entry and embraced by over seven acres of lush, verdant grounds in the heart of the Village of Matinecock, 40 Piping Rock Road is more than a home—it’s a restorative retreat. Originally built in 1925 and thoughtfully renovated in 2008, this timeless Colonial estate blends historic

Lindsey Barnett Compass Greater NY LLC

40 Piping Rock Rd, Locust Valley, NY 11560
/37
$450,000 Open Sun 11AM - 1PM
- 4 Beds
- 2 Baths
- 2,150 Sq Ft
719 Hanshaw Rd, Ithaca, NY 14850

This desirable Cayuga Heights single-level home offers bright interiors, newer Anderson windows, a fireplace, utility/laundry room, and detached garages on each side. The convenient single-floor plan includes a spacious backyard with tree-lined privacy and an ample front yard with distant views. Just minutes from Triphammer Mall, shopping, dining, and Cornell University, the location is

Kelly Skeval Howard Hanna S Tier Inc

719 Hanshaw Rd, Ithaca, NY 14850
/36
$1,995,995
- 7 Beds
- 6 Baths
- 7,020 Sq Ft
589-595 Plank Rd, Phoenicia, NY 12464

This beautiful estate must be seen. Owned by the same family for over 40 years, the compound has been lovingly expanded and restored. It is anchored by an 1870 farmhouse with many amenities. You enter the house to a wonderful chef's kitchen with cathedral ceilings accompanied by a walk-in pantry. There are granite countertops and top appliances. The first floor includes a spacious entertaining

Michael Shaughnessy Halter Associates Realty

589-595 Plank Rd, Phoenicia, NY 12464
/48
$2,950,000
- 4 Beds
- 3.5 Baths
- 4,445 Sq Ft
132 Finch Rd, North Salem, NY 10560

Windward Mark Farm: Located in North Salem, NY Westchester County's Primer Equestrian town.Nestled on 9.4 acres of land on a prized dirt road in the heart of North Salem's renowned Bridle Trails. & conservation land. This property offers a captivating blend of elegant living and equestrian facilities.The main residence, a charming 4-bedroom, 3.5-bath Colonial, with an inviting front

Carol Goldberg Vincent & Whittemore R.E.

132 Finch Rd, North Salem, NY 10560
/31
$1,400,000
- 4 Beds
- 4 Baths
- 3,661 Sq Ft
5-15 Old Depot Way, Stanfordville, NY 12581

If you crave a truly unique property, love history or dream of hosting short term rentals, this property might be your ticket to ride. Built in 1889, the historic Train Station in the hamlet of Stanfordville is the only existing station remaining along the original former P&C line that ran alongside Wappinger Creek (known as one of the top 10 trout streams in NYS). Originally, the buildings

George Langa Houlihan Lawrence Inc.

5-15 Old Depot Way, Stanfordville, NY 12581
/28
$2,559,000
- 6 Beds
- 3 Baths
- 2,200 Sq Ft
572 Montauk Hwy, Westhampton Beach, NY 11978

This is just over an acre with TWO houses on it. Room for Pool, Tennis, expansion on the well built excellent condition main house completely renovated from roof down to interior studs in 2018. Small cottage, 2 bed, full bath and kitchen with all CO's would make a full service pool house. Property is also a possible subdivide. It is presently used as a licensed Airbnb with a staff of Property

Rosanna Gleixner Moriches Bay Realty

572 Montauk Hwy, Westhampton Beach, NY 11978
/100
$1,318,000
- Land
- 95 Acres
- $13,880 per Acre
528 Dyken Pond Rd, Petersburg, NY 12138

*SECLUDED/ISOLATED: Atop Rensselaer Plateau this 100 year family owned sprawling 95 acre OASIS is under 1 hour to active city life; Capital District NY, Berkshires MA & Southern VT! *HEALTHY ENVIRONS: Mountain fresh air is healthier, cleaner with less humidity & pollution. LAND: sand gravel banks, streams, fields, treed woods -low footprint. *WATER: 180 acre spring fed crystal clear lake. This is

Joseph Milanese Milanese Joe

528 Dyken Pond Rd, Petersburg, NY 12138
/25
$3,895,000
- 7 Beds
- 7 Baths
816 N Sea Rd, Southampton, NY 11968

Located on a beautifully landscaped 0.61-acre lot in Southampton, this 4,099-square-foot double-gable shingled traditional home was thoughtfully designed and custom-built by Farrell. Offering seven spacious bedrooms and seven bathrooms, the home blends timeless architecture with modern luxury across three finished levels. A stately stone front porch framed by classic columns sets the tone as you

Andrew Azoulay At The Firm

816 N Sea Rd, Southampton, NY 11968
/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

David Turner Compass Greater NY, LLC

48 Raafenberg Rd, Tarrytown, NY 10591
/43
$1,175,000
- 5 Beds
- 3 Baths
- 2,482 Sq Ft
303 Hicks Hill Rd, Stanfordville, NY 12581

Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

HOMER STALEY JR. Staley Real Estate, LLC

303 Hicks Hill Rd, Stanfordville, NY 12581
/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
/44
$9,955,000
- 9 Beds
- 6 Baths
- 3,944 Sq Ft
15A / 15 & 13 S Menantic Rd, Shelter Island Heights, NY 11964

For the first time in over a century, this extraordinary collection of generationally owned properties is being offered together as a singular and rare opportunity. Nestled along the serene and picturesque Menantic Creek, these three separate parcels combined total 4.9 acres, which have been combined into one sale, presenting an unrivaled waterfront retreat. The Menantic Creek, known as Hurricane

Paula Quesnel - Jerman Daniel Gale Sothebys Intl Rlty

15A / 15 & 13 S Menantic Rd, Shelter Island Heights, NY 11964
/105
$385,000
- 3 Beds
- 1 Bath
- 1,240 Sq Ft
12 Bluebird Dr, Lake Luzerne, NY 12846

Two homes for the price of one! This charming 3BD/1BA home comes with a separate 1BD in-law cottage on a spacious lot. Features include an open floor plan, new flooring, updated electrical, newer furnace, cozy fireplace, jacuzzi, and a partially finished basement. Enjoy the large deck overlooking beautiful gardens. Five sheds provide plenty of storage. The renovated in-law cottage is bright,

Wayne Hartard eXp Realty

12 Bluebird Dr, Lake Luzerne, NY 12846
/45
$825,000
- 6 Beds
- 2 Baths
- 2,154 Sq Ft
11-13 Eldridge Ln, Red Hook, NY 12571

Red Hook Village Compound! Once in a generation a property offering like this is available. Tucked in at the end of Eldridge lane in the village walkable to parks, shoppes, and restaurants. This is composed of a lovely four bedroom home, with 2 sunrooms, large living room with stone fireplace, massive bathroom with skylights, new roof with warranty, new skylights and carpets. The home is light

Chelsea Seiler MONDELLO UPSTATE PROPERTIES LLC

11-13 Eldridge Ln, Red Hook, NY 12571
/37
$1,595,000
- 4 Beds
- 3 Baths
- 3,980 Sq Ft
235 Knob Hill Rd, Stanfordville, NY 12581

Nestled on 56 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, sizeable barn, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air

Jeannine Simmons Corcoran Country Living

235 Knob Hill Rd, Stanfordville, NY 12581
/100
$849,999
- 4 Beds
- 3 Baths
- 2,000 Sq Ft
196 Dessecker Rd, Livingston Manor, NY 12758

Known as Birch Ridge Kennels and Hunting Preserve, this property has a multitude of available options. If your bird club is looking to buy their facility or you're a dog breeder looking for a spot to breed and train dogs, this is for you. Or perhaps you are someone looking for a large tract of land with a business opportunity such as a pheasant and upland bird hunting preserve, a pheasant or

Clint Carlson WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

196 Dessecker Rd, Livingston Manor, NY 12758
/50
$599,000
- 2 Beds
- 2 Baths
- 4,034 Sq Ft
2008 Spencer Rd, Newfield, NY 14867

Escape to a world of natural beauty and tranquility with this extraordinary 65-acre estate, a bucolic haven boasting meadows, wooded trails, a serene pond, babbling streams, and picturesque gorges. This one-of-a-kind property offers a rare opportunity to own a piece of paradise in the heart of nature. Main Residence Features: Massive Cathedral Ceiling Great Room: The heart of the main residence

Katherine Burke Howard Hanna S Tier Inc

2008 Spencer Rd, Newfield, NY 14867
/50
$9,999,000
- 14 Beds
- 14.5 Baths
- 22,000 Sq Ft
1 Swan Place, Saint James, NY 11780

LUXURY PROPERTY AUCTION: September 10 - September 17Accepting Starting Bids Through 9th of September.Starting Bids 6MM +Daily OPEN HOUSES by appointment only. Weekend open houses, Sunday 9-12 or by appointment, with proof of funds or equivalent The submission of a starting bid can earn you up to a 50% reduction in buyer's premium.An extraordinary legacy awaits at

Kyle Roskot The Agency Northshore NY

1 Swan Place, Saint James, NY 11780
/23
$714,999
- 7 Beds
- 4 Baths
- 1,600 Sq Ft
33 Hilliard Ave, Central Islip, NY 11722

HAVE YOU BEEN LOOKING FOR YOU NEXT RENTAL INVESTMENT or Next FORVER HOME?Welcome to this 7-bedroom, 4-bathroom Cape Cod-style corner home! This beautifully maintained home features a full, finished basement, with its own separate entrance and proper permits. a first-floor bedroom, and a beautiful kitchen with granite countertops and stainless steel appliances. The property also includes a

Javier Enriquez Douglas Elliman Real Estate

33 Hilliard Ave, Central Islip, NY 11722
/18
$625,000
- 7 Beds
- 3 Baths
- 2,829 Sq Ft
44-52 Park Ln, Tannersville, NY 12485

This exceptional investment property, located just a short walk from the mountain and Main Street's amenities in Hunter, offers tremendous income potential with three houses on one deed. The main 4-bedroom, 2-bath house generates $2,500 in monthly rent, while the charming 3-bedroom, 1-bath cottage brings in $1,700 per month. The third house, in need of renovation, presents a fantastic opportunity

Brandon Oot Core Real Estate Team

44-52 Park Ln, Tannersville, NY 12485
/92
$24,900,000
- 6 Beds
- 13 Baths
- 19,341 Sq Ft
637 N Broadway, Saratoga Springs, NY 12866

A one-of-a-kind opportunity to own this luxurious Saratoga Springs Estate on prestigious North Broadway! This magnificent property comes furnished (exclusions apply) & has been meticulously updated w/new state-of-the-art mechanical systems including electrical, heating, plumbing, lighting, Savant home control system & new home security system. This 19,000SF estate features an exquisite primary

Julie Bonacio Julie & Co Realty, LLC

637 N Broadway, Saratoga Springs, NY 12866
/50
$2,895,000
- 5 Beds
- 6 Baths
- 6,435 Sq Ft
16 State School Rd, Warwick, NY 10990

Longhouse Farm is a breathtakingly restored farmhouse that seamlessly blends historic elegance with luxurious modern upgrades. Nestled on over 11 acres of scenic beauty, this equestrian estate offers a perfect balance of sophistication and tranquility. The property includes a stunning main house, a charming guest house (which comes fully furnished), a 9-stall barn, and a 4-stall run-in

Jason Kerwar William Raveis-New York, LLC

16 State School Rd, Warwick, NY 10990
/36
$18,995,000
- 8 Beds
- 13 Baths
- 13,481 Sq Ft
104 Premium Point Rd, New Rochelle, NY 10801

Welcome to Four Seasons waterfront living! Introducing this brand-new Malibu-cool stunner beautifully situated atop a private peninsula overlooking Long Island Sound and backing onto the tranquil waters of Premium Mill Pond. This Architectural Digest-quality home is the creme de la creme of an exclusive guard-gated community that’s just 35 minutes from NYC in the town of Mamaroneck. Such an

Wendy Alper Julia B Fee Sothebys Int. Rlty

104 Premium Point Rd, New Rochelle, NY 10801
/40
$2,750,000
- 4 Beds
- 2.5 Baths
- 2,279 Sq Ft
581 Gayhead-Earlton Rd, Leeds, NY 12451

Magnolia Mae Farm is a quintessential Hudson Valley farmhouse with complete privacy and seclusion that offers a respite from the outside world. This 174 acre compound, 20 minutes from Hudson, NY., consists of a main house, guest house, caretaker's house and writer's cabin. Enter down a private half mile approach under a canopy of maples and lindens that open to reveal an oasis of rolling hills.

Marina Tatistcheff Compass Greater NY LLC

581 Gayhead-Earlton Rd, Leeds, NY 12451
/38
$580,000
- 3 Beds
- 2 Baths
- 1,490 Sq Ft
78 Old Liberty Rd, Livingston Manor, NY 12758

Black Bear's aesthetic sensibility is refined yet unpretentious, a siren call for Catskills enthusiasts. This basecamp is located at the entrance to the Catskill Park, and is only 100 miles to New York City. Set on a quiet road, with three private acres of meadow and forest, the renovation leans into modern interiors, plenty of light and thoughtfully designed spaces for hosting. A cheerful front

Robin Jones Anatole House LLC

78 Old Liberty Rd, Livingston Manor, NY 12758
/39
$1,900,000
- 10 Beds
- 10 Baths
- 10,034 Sq Ft
1474 High Falls Rd, Catskill, NY 12414

his property features 50 beautiful acres with a lovely pond that creates an oasis of tranquility with four sprinklers that rise out of the water. The Estate also has great hiking trails through the woods, boasts an indoor Olympic-size heated pool with new liner and dehumidifier system. There are a total of 10 bedrooms each with full bath and fireplaces. The lower area has 6 suites, around the

Siobhan Scanlan Win Morrison Realty-K

1474 High Falls Rd, Catskill, NY 12414
/60
$850,000
- 6 Beds
- 8 Baths
- 8,000 Sq Ft
16 W Main St, Cambridge, NY 12816

A remarkable property, known as the Rice Mansion Inn, is the Crown Jewel of Cambridge. The 8,000 sq ft mansion is ideally situated in the heart of this picturesque village, near Vermont's Green Mountains and the NYS Adirondacks, with convenient access to Albany and Saratoga. The Mansion features three floors, six bedrooms (five of which are en-suites), and the potential for three additional

Jayne Schermerhorn Signature One Realty Grp, LLC

16 W Main St, Cambridge, NY 12816
/114
$569,000
- 5 Beds
- 3 Baths
- 2,586 Sq Ft
49 County Route 39, Round Top, NY 12473

An Outstanding Contemporary Home with 5 Bedrooms & 3 Baths on 15 Acres with a Beautiful Stream that can be used as a Mother/Daughter in the Charming Hamlet of Round Top! There's a captivating old red barn for animals, equipment, vehicles, recreation, entertainment, an artist's studio, a workshop, a creative space, or a home business asset. There's a 2 story bungalow that needs work and repairs

Theodore Banta III RVW Select Properties

49 County Route 39, Round Top, NY 12473
/49
$1,790,000
- 5 Beds
- 4.5 Baths
- 3,850 Sq Ft
68 Glenlawn Ave, Sea Cliff, NY 11579

This rare and versatile property offers TWO homes on one parcel, ideal for an income-producing legal rental, a true mother-daughter or room for an au pair! The beautiful 1930’s bungalow and separate guest house/apartment have been meticulously restored and offer brand-new roofs, siding, windows, insulation, electrical, plumbing andmechanical systems, in addition to all-new interior finishes.

Melinda Toner Compass Greater NY LLC

68 Glenlawn Ave, Sea Cliff, NY 11579
/33
$165,000
- 6 Beds
- 6 Baths
5868 State Route 32, Westerlo, NY 12193

Attention Investors!! Great opportunity with major potential in the Town of Westerlo. The School District is Greenville and only 7 miles from the property. The Retail space is situated on 3.1 acres is currently being used to sell RC cars. Property also consists of a 3-bedroom,1-bathroom single family home currently rented out and the tenant pays all utilities. Property consists of two

Cindy Van Steenburg Win Morrison Realty

5868 State Route 32, Westerlo, NY 12193
/55
$2,500,000
- 2 Beds
- 5 Baths
- 2,331 Sq Ft
1091 Albany Post Rd, Gardiner, NY 12525

Unveiling a Hidden Gem in Gardiner: Where Luxury Meets Endless Possibilities! Nestled in the heart of Gardiner, this meticulously restored Cape Cod home is a perfect blend of timeless elegance and modern comfort. Boasting 2,200 square feet of beautifully designed living space, this home offers an unparalleled living experience from the moment you step inside. The inviting living room,

Kyla Thomas Howard Hanna Rand Realty

1091 Albany Post Rd, Gardiner, NY 12525
/63
$8,850,000 Open Sat 1PM - 4PM
- 4 Beds
- 4.5 Baths
- 6,309 Sq Ft
890 Bald Mountain Rd, Austerlitz, NY 12017

LUXURY PROPERTY AUCTION: 4-17 SEPTEMBER.Accepting Starting Bids Through 3 September.The submission of a starting bid can earn you a reduction in buyer's premium.An extraordinary architectural masterpiece awaits at The Bald Mountain Estate, commanding eighty-five pristine acres atop Columbia County's highest peaks. This four-building contemporary compound epitomizes Hudson

Rachel Haley Houlihan Lawrence Inc.

890 Bald Mountain Rd, Austerlitz, NY 12017
/45
$1,999,000
- 5 Beds
- 4 Baths
- 3,738 Sq Ft
10 Hemlock Ct, Oyster Bay, NY 11771

Nestled in the village of Laurel Hollow in Oyster Bay, this beautiful 5 bedroom, 4 bathroom home is a rare gem that exudes charm, warmth, and character. Situated on a sprawling 2-acre lot at the end of a peaceful cul-de-sac, this property offers the ultimate privacy and luxury living. As you approach, you’ll be captivated by the lush landscaping and serene setting. Step inside to find a

Marianne Conroy LAFFEY REAL ESTATE

10 Hemlock Ct, Oyster Bay, NY 11771
/32
$11,250,000
- 5 Beds
- 7.5 Baths
- 17,200 Sq Ft
46 Ledgerock Ln, Hyde Park, NY 12538

Ledgerock, the riverfront masterpiece by modern architect Lee Ledbetter is back on the market after undergoing significant infrastructure improvements. This one-of-a-kind estate offers the finest Hudson River and Catskill Mountain views on the market today and is set on 5 private acres. Constructed from the finest materials available, this gorgeous fossilized French limestone & glass compound

Jason Karadus Corcoran Country Living

46 Ledgerock Ln, Hyde Park, NY 12538
/35
$18,750,000
- 11 Beds
- 7.5 Baths
- 7,500 Sq Ft
461 Silvernails Rd, Pine Plains, NY 12567

Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley.

Byron Anderson Compass Greater NY, LLC

461 Silvernails Rd, Pine Plains, NY 12567
/35
$809,000
- 6 Beds
- 2.5 Baths
- 3,547 Sq Ft
11 W Bridge St, Saugerties, NY 12477

Step back in time while enjoying modern comforts in this meticulously maintained Federal-style brick home, built in the 1800s and located in the picturesque Village of Saugerties.This historic residence has been thoughtfully updated to meet contemporary needs while preserving its original charm. The main home features 4 bedrooms and 1.5 bathrooms, with a tastefully renovated kitchen that

Eliana Amodio Amodio Real Estate & Prop

11 W Bridge St, Saugerties, NY 12477
/25
$799,000
- 3 Beds
- 4 Baths
- 4,450 Sq Ft
66 Lake Shore Rd, Westport, NY 12993

This home, at 66 Lake Shore Road, is situated high on the hillside of the Furnace Point area of Westport's north shore. It's near the village, but situated with unobstructed, stunning, panoramic views overlooking Lake Champlain and the surrounding terrain. Its beginning was as a moderate size home. An addition was completed in 2020 that roughly tripled its living, garage, utility, and vineyard

Jack Yao Realmart Realty, LLC

66 Lake Shore Rd, Westport, NY 12993

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New York Homes for Sale with a Guest House

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