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Olive, NY Homes for Sale

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  • /41

    $799,900

    Open House 7/25 $129K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,736 Sq Ft

    85 Kelder Hwy, Olivebridge, NY 12461

    A European sensibility runs through the home, a respect for what was built well more than a century ago, paired with quiet updates that make the space work for how people live now. While town records place the home's construction around 1900, there are intriguing signs that portions of the structure may be considerably older. Original doors, wide-plank floors with real patina, and a gourmet

    Agent Photo

    Stefan Bolz

    Hudson Dwellings Realty

    85 Kelder Hwy, Olivebridge, NY 12461
  • /45

    $732,000

    $47K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    11 Oak Mountain Farm Rd, Boiceville, NY 12412

    Storybook Charm, Artistic Soul, and Mountain Views in the Heart of the Ashokan Reservoir and Catskill Mountains Corridor Originally built in 1930 from a mail-order catalog kit, this enchanting home has evolved into a truly distinctive country retreat where creativity, craftsmanship, and comfort come together. Set in a peaceful setting with mountain views, yet just five minutes from both the

    Agent Photo

    Amy Lonas

    Coldwell Banker Village Green

    11 Oak Mountain Farm Rd, Boiceville, NY 12412
  • /42

    $1,150,000

    $200K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    23 Traver Hollow Rd, Boiceville, NY 12412

    Custom-Built Modern Home with Dramatic Mountain Views There are homes with views - and then there are homes built for the view. Affectionately known as Mountain Thyme, the mountain is not simply a backdrop but the defining presence of the property. From the moment you arrive, it rises dramatically into view, close enough to feel immersive, yet expansive enough to inspire. Designed to showcase the

    Agent Photo

    Leigh Bokser

    Compass Greater NY, LLC

    23 Traver Hollow Rd, Boiceville, NY 12412
  • /42

    $574,999

    • 6 Beds
    • 2 Baths
    • 1,842 Sq Ft

    2 Mountain Valley Rd, Boiceville, NY 12412

    A rare and remarkable multi-family opportunity nestled in the heart of the Catskills — 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is virtually unheard of in the multi-family market. Set against the stunning natural backdrop of Ulster County's Catskill Mountains, this 1,842 total square foot

    Agent Photo

    Richard Baxter

    Keller Williams Realty

    2 Mountain Valley Rd, Boiceville, NY 12412
  • /47

    $575,000

    • 6 Beds
    • 2 Baths
    • 1,842 Sq Ft

    2 Mountain Valley Rd, Boiceville, NY 12412

    A rare and remarkable multi-family opportunity nestled in the heart of the Catskills - 2 Mountain Valley Road, Boiceville, New York presents two fully self-contained units, each delivering a level of space, privacy, and independence that is virtually unheard of in the multi-family market. Set against the stunning natural backdrop of Ulster County's Catskill Mountains, this 1,842 total square foot

    Agent Photo

    Richard Baxter

    KELLER WILLIAMS REALTY

    2 Mountain Valley Rd, Boiceville, NY 12412
  • /11

    $749,900

    • Land
    • 27.9 Acres
    • $26,878 per Acre

    Tbd New York 28, Boiceville, NY 12412

    Incredible 27.9-acre development opportunity with mixed-use zoning and dual access from Route 28 and Upper Boiceville road. The front portion is zoned Highway Business with a 0.5-acre minimum, ideal for commercial use along this high-traffic corridor. The rear is zoned residential with a 1-acre minimum and could be subdivided for housing, a strip along the middle can go either way to be added to

    Agent Photo

    Teresa Falkowski

    Keller Williams Realty HV Nort

    Tbd New York 28, Boiceville, NY 12412
  • /48

    $1,349,000

    New Construction $150K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,850 Sq Ft

    99 W Shokan Heights Rd, West Shokan, NY 12494

    Tucked into the rolling landscape of West Shokan, where seasonal Catskill Mountain views emerge through the trees, this new construction contemporary home offers a rare blend of modern craftsmanship, warmth, and quiet luxury across 4.25 private acres. Surrounded by forest and designed to embrace its natural setting, the home captures the essence of elevated country living--where refined interiors

    Richard Vizzini Corcoran Country Living

    99 W Shokan Heights Rd, West Shokan, NY 12494
  • /51

    $899,000

    • 3 Beds
    • 4 Baths
    • 2,575 Sq Ft

    67 Private Road 24, Olivebridge, NY 12461

    Set at the end of a quiet private road, this custom-built cedar contemporary home is surrounded by nearly five acres of rolling lawn, mature woods, and sweeping mountain views. Thoughtfully positioned to embrace its natural setting, the property offers the kind of privacy that's increasingly difficult to find, while still being just minutes from the Ashokan Reservoir, hiking trails, local farm

    Richard Vizzini Corcoran Country Living

    67 Private Road 24, Olivebridge, NY 12461
  • /31

    $824,999

    • 2 Beds
    • 2 Baths
    • 1,910 Sq Ft

    18 Haberland Ln, Olivebridge, NY 12461

    There is something instantly comforting about this home. Warm, welcoming, and lovingly maintained, it offers the kind of easy living that never goes out of style. Whether gathering around the fireplace with friends, enjoying a quiet morning coffee, or unwinding after a long day, every space feels inviting, functional, and meant to be lived in. Set amidst peaceful natural surroundings with views

    Richard Vizzini Corcoran Country Living

    18 Haberland Ln, Olivebridge, NY 12461
  • /50

    $950,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    52 Brodhead Rd, West Shokan, NY 12494

    Where eagles fly and mountains kiss the sky, this beautifully maintained homestead showcases quality craftsmanship and thoughtful upgrades throughout. Whether you are an artisan, woodworker or equestrian, the well-equipped barn with Wi-Fi, telephone/paging system and electricity can easily meet your needs. The property features a thriving, fenced vegetable garden with separate well and shed

    Mary McKinney Coldwell Banker Village Green

    52 Brodhead Rd, West Shokan, NY 12494
  • /70

    $899,990

    $280K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,670 Sq Ft

    10 Kolb Rd, Boiceville, NY 12412

    Dear buyer, I want you to know the story of this house. My family bought it three years ago and we did a total renovation to all the bathrooms and kitchen with new appliances and tile and all new fixtures. We also changed the back of the house and opened it up with a huge dormer facing the mountain since before the main view was to the expansive side meadow. We thought this was going to be our

    Jasmine Jordaan Halter Associates Realty

    10 Kolb Rd, Boiceville, NY 12412
  • /50

    $2,000,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,671 Sq Ft

    53 Freeman Avery Rd, Olivebridge, NY 12461

    An architectural gem tucked away on 40 acres of pristine forest, this striking 3,671-square-foot residence is a stunning fusion of modern architecture and natural beauty. Crafted by the acclaimed Resolution: 4 Architecture, incorporating all of their most coveted features that converge in this divine mid century modern design. Travel down the tree lined driveway past a cascading waterfall to a

    Richard Vizzini Corcoran Country Living

    53 Freeman Avery Rd, Olivebridge, NY 12461
  • /53

    $1,995,000

    $105K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 5,199 Sq Ft

    250 Brodhead Rd, West Shokan, NY 12494

    A rare sanctuary where wellness, nature, and inspired country living converge across 17 idyllic acres. Framed by meadows, woodland, and a serene pond, the property offers a rare sense of escape--an immersive landscape designed as much for gathering and inspiration as for quiet retreat. At the heart of the grounds, the pond becomes a focal point for a lifestyle centered around wellness and

    Richard Vizzini Corcoran Country Living

    250 Brodhead Rd, West Shokan, NY 12494
  • /63

    $8,500,000

    $1M PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 6,284 Sq Ft

    197-199 Chestnut Hill Rd, Stone Ridge, NY 12484

    Discover one of the Hudson Valley's most remarkable properties—an 80-acre private estate in coveted Stone Ridge where curated landscapes, architectural charm, and world-class amenities converge to create an unparalleled retreat. Designed for both refined living and unforgettable entertaining, this extraordinary compound feels more like a private resort than a residence. Approach the front gate

    Richard Vizzini Corcoran Country Living

    197-199 Chestnut Hill Rd, Stone Ridge, NY 12484
  • /50

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 2,443 Sq Ft

    77 Lower Sahler Mill Rd, Olivebridge, NY 12461

    Tucked away on a sleepy country road, this gut-renovated and completely re-imagined 1930s retreat offers the perfect blend of privacy, natural beauty, and modern comfort. The main house is defined by a copious amount of windows and skylights which drenches the home in natural light and creates a perpetual connection to the outdoors. The kitchen boasts new appliances, soapstone counters and a

    Joseph Satto Compass Greater NY, LLC

    77 Lower Sahler Mill Rd, Olivebridge, NY 12461
  • /32

    $799,000

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

    4248 State Route 28, Boiceville, NY 12412

    Welcome to the most charming 1920s Arts & Crafts masterpiece. Whether you're plotting a full-time escape from the city or a weekend sanctuary, this light-soaked gem in the historic hamlet of Boiceville is the ultimate choice.Step through the center entry hall and prepare to swoon: beamed ceilings, historic charm, and a living room anchored by a fireplace with a cozy wood-burning stove.

    Carol Graham Corcoran Country Living

    4248 State Route 28, Boiceville, NY 12412
  • /5

    $67,500

    $8K PRICE DROP
    • Land
    • 14,374 Sq Ft
    • $204,545 per Acre

    1470 County Road 2, Olivebridge, NY 12461

    Looking to build a quaint, country escape on a low maintenance buildable lot? 1470 County Road 2 is the perfect location to do so! Equipped with a survey, BOH approval for a 2 bedroom home and zoning board of appeals approval from the local municipality, authorizes this lot as buildable for a 24x40 home. Bring your minimalistic 960 square foot country home to vision on this 0.44 acre lot in

    Zachary Jarvis BHHS Nutshell Realty

    1470 County Road 2, Olivebridge, NY 12461
  • /19

    $425,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    1906 County Road 3, Olivebridge, NY 12461

    This charming cottage in Olivebridge NY proves that great things really do come in small packages. Thoughtfully designed for easy living, it's the kind of home that lets you spend less time maintaining and more time enjoying everything the Hudson Valley has to offer.Inside, warm and inviting spaces feel instantly welcoming, while an airy loft provides the perfect spot for a home office,

    Jason Nadeau Compass Greater NY, LLC

    1906 County Road 3, Olivebridge, NY 12461
  • /17

    $99,900

    $50K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 800 Sq Ft

    244 Upper Samsonville Rd, Olivebridge, NY 12461

    Perfect 1 acre Catskill Mountain property with old mobile home in need of total rehabilitation. No well or septic on site. No existing heat source.

    Timothy Ayers Berardi Realty

    244 Upper Samsonville Rd, Olivebridge, NY 12461
  • /35

    $599,900

    • 3 Beds
    • 3 Baths
    • 1,568 Sq Ft

    90 Jomar Ln, Olivebridge, NY 12461

    Welcome to 90 Jomar Lane, a beautifully maintained, move-in-ready ranch offering the perfect blend of comfort, space, and privacy. The main level features 1,568 square feet of thoughtfully designed living space, complemented by an additional 920 square feet in the fully finished basement, providing plenty of room for entertaining, recreation, a home office, or guest accommodations. This inviting

    Chris Weber BHHS HUDSON VALLEY PROP-NP

    90 Jomar Ln, Olivebridge, NY 12461
  • /43

    $599,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    93 Sundown Rd, Kerhonkson, NY 12446

    Welcome to 93 Sundown Road. From the moment you enter this charming Catskills home, you will be transported to a time when life felt simpler and more peaceful. Built in 1820, this three-bedroom, one-and-a-half-bath retreat has been lovingly restored to reflect its historical origins without sacrificing modern conveniences. Inviting outdoor spaces provide numerous places to slow down, unwind, and

    Andrew Condon Halter Associates Realty

    93 Sundown Rd, Kerhonkson, NY 12446
  • /27

    $2,390,000

    • Land
    • 182.2 Acres
    • $13,117 per Acre

    Tbd Ryan Rd, Kerhonkson, NY 12446

    182 acres in Kerhonkson. Privacy, scale, beauty, and possibility in one rare piece of land. Tucked into the quiet landscape of Kerhonkson, this extraordinary 181-acre property offers the kind of space, privacy, and natural character that is almost impossible to find at this scale. Whether imagined as a secluded family compound, a private mountain retreat, or a thoughtful three-home development

    Kristian Unvericht Compass Greater NY, LLC

    Tbd Ryan Rd, Kerhonkson, NY 12446
  • /33

    $779,000

    $46K PRICE DROP
    • Land
    • 8.18 Acres
    • $95,232 per Acre

    281 Dewitt Rd, Olivebridge, NY 12461

    ONE OF THE MOST SPECTACULAR WATERFALLS IN ULSTER COUNTY is front and center on this extremely rare and unusual land offering. The visual beauty of the waterfall, stream, cliffs and land is unparalleled. Calming audio of the waterfall and rushing Mettacahonts stream is 24/7 and year-round. Pulling into the circular driveway you are greeted by a master stone worker's hand-built raised garden bed,

    Anne Hilton Purvis Coldwell Banker Village GreenN

    281 Dewitt Rd, Olivebridge, NY 12461
  • /28

    $995,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,827 Sq Ft

    264 Wynkoop Rd, Olivebridge, NY 12461

    On a storybook wooded lot in one of the Hudson Valley's most sought-after neighborhoods, this brand new Scandinavian-inspired farmhouse checks all the boxes for the perfect Catskill weekend getaway or a forever family home. Built by one of the area's most respected builders, this luxury home features a gourmet kitchen, floor-to-ceiling living room windows, a custom two-story fireplace, and an

    Dylan Taft Taft Street Realty, Inc.

    264 Wynkoop Rd, Olivebridge, NY 12461
  • /2

    $80,000

    $100K PRICE DROP
    • Land
    • 5.61 Acres
    • $14,260 per Acre

    00 Fischer Ln, Olive, NY 12461

    Location location location! This beautifully wooded lot is located on aprivate road with close proximity to Woodstock. Build your dream home or use it for your privacy buffer. and combine it with Kelder and 55 G Fischer for a total of 20 acres.

    Adrienne Volpe KW Mid-Hudson

    00 Fischer Ln, Olive, NY 12461
  • /6

    $725,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    720 Upper Cherrytown Rd, Kerhonkson, NY 12446

    To be built new construction by Cedar Development Group (@CedarDGHomes on IG). CDG uses fine finishes throughout and significant customization is possible with this home, or you can proceed with it as contemplated. Pictures are representative of another similarly completed house by CDG however exact finishes may vary and are subject to change or withdrawal. Home size can be augmented or reduced

    Ryan Scully Cedar Properties

    720 Upper Cherrytown Rd, Kerhonkson, NY 12446
  • /43

    $699,999

    Open Sat 12PM - 2PM Coming Soon
    • 5 Beds
    • 2.5 Baths
    • 2,938 Sq Ft

    252 Vly Atwood Rd, Stone Ridge, NY 12484

    Come home to The Vly Woods, a spacious and serene colonial in Stone Ridge, NY. Set back on a country road, this well-maintained 5-bedroom, 3-bathroom home sits on nearly 4 acres of private wooded property with established gardens, offering a sought-after combination of seclusion and convenience. Step through double doors into a welcoming foyer, and on to a spacious living room, bright eat-in

    Karen Dietrich Ally Realty

    252 Vly Atwood Rd, Stone Ridge, NY 12484
  • /12

    $224,999

    • 2 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    106 Sheldon Hill Rd, Olivebridge, NY 12461

    Investor opportunity in Olivebridge! Situated on 1.12 acres, 106 Sheldon Hill Road offers a 2-bedroom, 1.5-bath home with approximately 1,456 square feet of living space and a full unfinished basement, providing additional potential for storage or future expansion. Ideal for investors, contractors, or buyers looking for a renovation project in the Hudson Valley, this home presents a chance to

    Vincent Reda Keller Williams Realty

    106 Sheldon Hill Rd, Olivebridge, NY 12461
  • /7

    $149,000

    29 Reservoir Rd, Shokan, NY 12481

    Property has a 3BR, 1bath house which needs complete Renovation or Demolition. BEING SOLD AS-IS This is an ideal quiet location just a few lots off route 28 and walkable to The Asokan Reservoir. Minutes from all services and shopping. Kingston and Woodstock are near-by. Onteora school system right down the road. Rail Trail around the corner. Live in a country location and work in Kingston with

    Faye Storms Ruth Gale Realty

    29 Reservoir Rd, Shokan, NY 12481
  • /20

    $420,000

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,372 Sq Ft

    127 Du Bois Rd, Shokan, NY 12481

    OPEN HOUSE SATURDAY 7/11 from 11 am - 1:00 If you're looking for peaceful country living, this inviting ranch-style home on 1.42 acres may be just what you've been waiting for. Set on a quiet road, it offers 3 bedrooms, 1 1/2 bathrooms, and a spacious living room with a cozy fireplace. Hardwood floors lie beneath the carpets, adding even more potential. The full finished basement provides plenty

    Tracy Galvin Mid Hudson Valley Realty Corp.

    127 Du Bois Rd, Shokan, NY 12481
  • /40

    $859,000

    • 3 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    640 Acorn Hill Rd, Olivebridge, NY 12461

    Private newly renovated retreat on 2.57 Acres! Welcome to 640 Acorn Hill Road, where peace, privacy, and modern living come together in a beautiful natural setting. Tucked away from the road on this move-in ready home offers an open-concept layout designed for both everyday living and entertaining. The home features timeless board and batten siding, a standing-seam metal roof, and thoughtfully

    Megan Rios Berardi Realty

    640 Acorn Hill Rd, Olivebridge, NY 12461
  • /34

    $2,199,000

    $50K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    209 Beaverkill Rd, Kingston, NY 12401

    Nine and a half acres. A private island. A river at your edge. And a home built entirely around you. Deep in the Hudson Valley, where the Esopus River carves through one of the region's last truly private waterfront parcels, sits a rare 9.56 acre property that offers something the market almost never produces, total seclusion, direct river frontage, and access via a primitive trail to your own

    Zak Gumpel HRH Development Brokers LLC

    209 Beaverkill Rd, Kingston, NY 12401
  • /33

    $795,000

    Open Sat 11AM - 12:30PM
    • 3 Beds
    • 1.5 Baths
    • 2,037 Sq Ft

    137 Stillwater Rd, Stone Ridge, NY 12484

    Your storybook ending begins now.... Tucked away on 2.3 private acres in Stone Ridge, this spirited 1980s passive home, three bedrooms, two baths, 2,037 square feet, strikes a balance that's increasingly hard to find: genuinely charming without trying too hard, and quietly stylish in every detail. Fully enclosed by fencing, the grounds are yours to claim completely, a haven for gardens cultivated

    Quinn Hagstrand BHHS HUDSON VALLEY PROP-WDST

    137 Stillwater Rd, Stone Ridge, NY 12484
  • /30

    $515,000

    • 2 Beds
    • 1 Bath
    • 1,251 Sq Ft

    183 Mill Rd, Olivebridge, NY 12461

    The perfect getaway from the hustle and bustle of the world. Nestled quietly in the Catskill Mountain Range, just minutes from the Ashokan Reservoir and a short drive away from Woodstock, Rosendale, Kingston, and New Paltz sits this lovely, renovated 2 bed, 1 bath home. On the property you'll find 2.2 acres of tranquility as you can look out the back windows at nearly all hours and see the

    Michael Bussa K. Fortuna Realty, Inc.

    183 Mill Rd, Olivebridge, NY 12461
  • /50

    $1,975,000

    • 3 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    430 Buck Rd, Stone Ridge, NY 12484

    Set on coveted Buck Road in Marbletown, this property offers a rare combination of privacy, beauty, and convenience on nearly 29 acres across two contiguous parcels. It's easy to see why this stretch of road is so admired--peaceful and scenic, yet just minutes from the heart of Stone Ridge. Beyond a long, wooded drive, the trees open to reveal a property that has taken shape over more than two

    Emily Daniels BHHS Nutshell Realty

    430 Buck Rd, Stone Ridge, NY 12484
  • /23

    $399,000

    • Land
    • 9.56 Acres
    • $41,736 per Acre

    Tbd-Lot 1 Beaverkill Rd, Kingston, NY 12401

    An exceptionally rare opportunity to build with HRH Development on one of the most breathtaking parcels in the Catskills. Set on 9.56 private acres, this shovel-ready property offers the perfect blend of seclusion, natural beauty, and proximity to the region's most sought-after destinations. Positioned on a dramatic and secluded plateau bordered by the Esopus Creek, the property is BOH approved

    Zak Gumpel HRH Development Brokers LLC

    Tbd-Lot 1 Beaverkill Rd, Kingston, NY 12401
  • /32

    $729,000

    • 3 Beds
    • 3 Baths
    • 2,116 Sq Ft

    14 Mountain Valley Rd, Olive, NY 12461

    Welcome to your private mountain retreat in the heart of the Catskills. Set on 2.1 wooded acres, this beautifully maintained home offers an ideal blend of modern comfort, outdoor living, and year-round recreation.Significantly upgraded by its current owners, this property is perfect for those seeking tranquility without sacrificing convenience. Inside, the remodeled kitchen features modern

    Ronnie McPeek Amodio Real Estate & Prop

    14 Mountain Valley Rd, Olive, NY 12461
  • /12

    $299,000

    • Land
    • 3.34 Acres
    • $89,521 per Acre

    414 Buck Rd, Stone Ridge, NY 12484

    Set along beloved Buck Road, this 3.34-acre parcel offers a rare opportunity to create something new in one of Marbletown's most sought-after locations. The property combines open lawn, mature trees, historic stone walls, and a private woodland backdrop to create a setting that feels established and peaceful from the moment you arrive. Once home to a residence, the existing clearing provides an

    Emily Daniels BHHS Nutshell Realty

    414 Buck Rd, Stone Ridge, NY 12484
  • /47

    $1,525,000

    • 3 Beds
    • 2.5 Baths
    • 3,030 Sq Ft

    457 Krumville Rd, Olivebridge, NY 12461

    Tucked into a dramatic rock ridge with sweeping views of the Catskill Mountains, this renovated farmhouse invites you to slow down and savor country living at its finest. Spanning just over 3,000 square feet, the home balances rustic character with thoughtful modern updates throughout. The renovated kitchen, anchored by warm butcher block counters, flows gracefully into a generous dining room.

    Anna Barcone BHHS Nutshell Realty

    457 Krumville Rd, Olivebridge, NY 12461
  • /50

    $849,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,485 Sq Ft

    18 Jomar Ln, Olivebridge, NY 12461

    You'll understand just how special this 41 Acre property is once you arrive. Just driving down the country road to get here is already a treat. Situated at the base of the majestic High Point Mountain you'll find a private driveway that takes you through a beautiful forest and then it opens up to acres of your own open farmlands.....the open fields are perfectly suited to horses and with an

    Edwin Maldonado Howard Hanna Rand Realty

    18 Jomar Ln, Olivebridge, NY 12461

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