Holmes, NY Homes for Sale

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  $4,250,000

  • 4 Beds
  • 5 Baths
  • 4,253 Sq Ft

  296-302 Stanford Rd, Millbrook, NY 12545

  Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated four or five bedroom, three full and two half bath main residence and a separate two bedroom, two and a half bath guest house. A dramatic formal

  Paula Redmond Corcoran Country Living - Mill

  296-302 Stanford Rd, Millbrook, NY 12545
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  /30

  $340,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  1666 Main St, Pleasant Valley, NY 12569

  Welcome to 1666 Main Street, a beautifully renovated classic early-1900s home in the heart of Pleasant Valley. This move-in ready property offers 3–4 bedrooms, 2 full baths, and over 2,000 square feet of living space on a low-maintenance .20-acre lot in the Arlington School District with low taxes.Inside, you’ll find refinished 100+ year-old Maple and Douglas Fir hardwood floors, upgraded

  Kiyoshi Henson RE/MAX Town & Country

  1666 Main St, Pleasant Valley, NY 12569
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  $549,000

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  809 Traver Rd, Pleasant Valley, NY 12569

  809 Traver is a stunning Dutch Colonial, maintained with uncommon discipline and enduring craftsmanship. Built in 1764 as the Peter Flagler House, it was the town’s central tavern and meeting House.Set on just over an acre of mature landscaping, enjoy your heated swimming pool - or walk steps to the lovely town of Pleasant Valley.The home’s layout is classic in its proportions. A Dutch

  Kelli Williams The Machree Group, LLC

  809 Traver Rd, Pleasant Valley, NY 12569
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  /24

  $510,000

  • 4 Beds
  • 2 Baths
  • 1,736 Sq Ft

  38 Forest Valley Rd, Pleasant Valley, NY 12569

  Welcome to 38 Forest Valley Road a beautifully maintained and thoughtfully updated 4-bedroom, 2-bath home set on a scenic, level one-acre lot in the Arlington Central School District. The main level features an updated kitchen with granite counter tops, wood cabinetry, and stainless steel appliances. Comfortable dining area that opens to the deck overlooking the private backyard and above-ground

  Debra Tarpey RE/MAX Town & Country

  38 Forest Valley Rd, Pleasant Valley, NY 12569
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  $649,000

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  71 O Halloran Cir, Pleasant Valley, NY 12569

  Welcome to 71 O’Halloran Circle, where space, privacy, and possibility come together on 3.74 scenic acres in Pleasant Valley. This inviting raised ranch offers 4 bedrooms, 2 and a half bathrooms, and a versatile layout designed for comfortable everyday living and effortless entertaining.Inside, generous living spaces provide plenty of room to gather, unwind, work from home, or create the

  Anna Traina BERKSHIRE HATHAWAY

  71 O Halloran Cir, Pleasant Valley, NY 12569
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  /38

  $3,500,000

  • 3 Beds
  • 4 Baths
  • 3,688 Sq Ft

  3531 Route 82, Millbrook, NY 12545

  Set on 5.85 private acres just under 90 minutes from Manhattan, Three Ponds Estate is a fully remodeled 4 bedroom, 3.5 bath residence designed by the owner and designer behind the award winning Millbrook Inn. That pedigree is felt the moment you arrive and carries through every room, from the bespoke finishes to the way the home is oriented to capture its extraordinary setting.Spanning 3,688

  Jordan Vaccaro Serhant LLC

  3531 Route 82, Millbrook, NY 12545
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  $1,625,000

  • 3 Beds
  • 2 Baths
  • 3,035 Sq Ft

  46 Hoxie Rd, Millbrook, NY 12545

  Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential. The light-filled home is defined by soaring 30-foot

  E. ELIZABETH PETERS Corcoran Country Living

  46 Hoxie Rd, Millbrook, NY 12545
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  $745,000

  $40K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,614 Sq Ft

  2327 Salt Point Turnpike, Clinton Corners, NY 12514

  Rich in history and character this 1820 farmhouse offers 5 bedrooms and three and a half baths a total of 4616 finished square feet in the main residence. Zoned as a legal 2 family home and the property is located in the 'H" Hamlet District of Clinton allowing for a variety of uses of the property. Gorgeous wide plank floors, many windows, 2 staircases, tucked away rooms add to the charm and

  Linda Lindsay Upstate Down

  2327 Salt Point Turnpike, Clinton Corners, NY 12514
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  /35

  $525,000

  • 3 Beds
  • 1.5 Baths
  • 1,928 Sq Ft

  12 Talbot Dr, Pleasant Valley, NY 12569

  Welcome to this beautifully updated move-in ready home, perfectly situated at the end of a quiet cul-de-sac, offering unmatched privacy and a peaceful, wooded backyard setting. Whether you're enjoying your morning coffee in the beautiful three-season sunroom or relaxing outdoors, this property provides the tranquility you've been searching for.Inside, you'll find numerous high-quality

  VINCENT MARTIN Serhant LLC

  12 Talbot Dr, Pleasant Valley, NY 12569
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  $339,000

  • 2 Beds
  • 1.5 Baths
  • 1,766 Sq Ft

  33 North Ave, Pleasant Valley, NY 12569

  This charming 1920s home combines character with comfortable one-level living in a highly walkable location. The inviting interior features two bedrooms, a home office, an efficient kitchen, a welcoming living room, a sun-filled dining room, one-and-a-half baths, and a mudroom with laundry. While the second floor creates flexibility for additional living space, the full basement provides generous

  Susan Whalen George T Whalen Real Estate

  33 North Ave, Pleasant Valley, NY 12569
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  $539,000

  $110K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,576 Sq Ft

  6 Route 343, Millbrook, NY 12545

  Welcome to this warm and inviting 3-bedroom, 1.5-bath home nestled in the heart of Dutchess County, just minutes from the Village of Millbrook and the Taconic State Parkway. From the moment you step into the entry foyer, you'll feel the character and comfort this home has to offer.The sun-filled living room impresses with a beamed ceiling and wood-burning fireplace — the perfect gathering

  Rebecca Marino Corcoran Country Living

  6 Route 343, Millbrook, NY 12545
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  $750,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  32 Cole Rd, Pleasant Valley, NY 12569

  Welcome to this lovely Hudson Valley estate where timeless architecture and exceptional privacy come together on 13.7 breathtaking park-like acres in the heart of LaGrange, just minutes from the Village of Millbrook. A picturesque quarter-mile, partially pine-lined driveway creates a country approach, setting the stage for this remarkable property. Perfectly positioned with a coveted

  Nicole Porter Houlihan Lawrence Inc.

  32 Cole Rd, Pleasant Valley, NY 12569
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  $650,000

  • 5 Beds
  • 3 Baths
  • 2,936 Sq Ft

  133 N Smith Rd, Lagrangeville, NY 12540

  RARE FIND.......Tucked away on 1.23 private acres in desirable LaGrangeville, this beautifully maintained duplex offers the perfect blend of comfort, flexibility, and opportunity. Surrounded by mature trees and peaceful countryside, the property provides a private retreat while remaining conveniently located near the Taconic State Parkway, Routes 55 and 82, Millbrook Village, parks, dining, and

  Arleen Sepulveda KW Hudson Valley North

  133 N Smith Rd, Lagrangeville, NY 12540
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  $625,000

  • 3 Beds
  • 2 Baths
  • 2,700 Sq Ft

  26 Hoof Print Rd, Millbrook, NY 12545

  Beautiful, oversized bilevel on the Washington/Union Vale town line, located just minutes from the charming Village of Millbrook. Recently renovated and truly move-in ready, this inviting home offers an open floor plan, abundant natural light, and spacious rooms throughout. The cook’s delight eat-in kitchen features custom cabinetry, an extended center island with built-in microwave, gorgeous

  Nicole Porter Houlihan Lawrence Inc.

  26 Hoof Print Rd, Millbrook, NY 12545
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  /50

  $1,350,000

  • 4 Beds
  • 5 Baths
  • 4,552 Sq Ft

  17 Audubon Trail, Salt Point, NY 12578

  Unique, exquisite & impeccable; these are the best descriptors for 17 Audubon Trl. This meticulously maintained and tastefully renovated home offers resort style amenities conducive to relaxing or entertaining for the most discerning buyer. Fully custom home loaded with incredible upgrades includes chef's kitchen complete with soapstone counters, Wolf range, Sub-Zero refrigerator and massive

  Dan Axtmann BHHS Hudson Valley Properties

  17 Audubon Trail, Salt Point, NY 12578
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  $729,000

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  580 Oak Summit Rd, Millbrook, NY 12545

  Charming country Cape Cod style home located minutes from the Village of Millbrook. This home offers an open floor plan with wood flooring, custom built kitchen cabinets, granite countertops, and stainless steel appliances. Dining room has slider to deck. Primary bedroom on first floor with full bath, including washer & dryer. Two large bedrooms are located on the second floor with a second full

  George Whalen III George T Whalen Real Estate

  580 Oak Summit Rd, Millbrook, NY 12545
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  /25

  $650,000

  • 3 Beds
  • 1.5 Baths
  • 3,193 Sq Ft

  59-61 Valley Farm Rd, Millbrook, NY 12545

  Step back in time and bring your vision to this classic 1870s Colonial, featuring original details throughout, perfectly situated on a lovely one + acre lot on a quiet country road. Flanked by mature pines and Flowering Hibiscus. The property offers a serene setting while being conveniently located near the charming village of Millbrook, NY. A unique opportunity for those looking to restore a

  Sarah Sartorini-Yarmoluk William Pitt Sothebys Int Rlty

  59-61 Valley Farm Rd, Millbrook, NY 12545
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  $1,195,000

  $180K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,820 Sq Ft

  101 Drake Rd, Pleasant Valley, NY 12569

  Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind

  Jake Garay Serhant LLC

  101 Drake Rd, Pleasant Valley, NY 12569
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  $1,250,000

  $250K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,068 Sq Ft

  3311 Franklin Ave, Millbrook, NY 12545

  Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire

  Ann Stettner Neil Charles Real Estate, LLC

  3311 Franklin Ave, Millbrook, NY 12545
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  /2

  $325,000

  • Land
  • 12.8 Acres
  • $25,391 per Acre

  0 Deer Pond Rd Unit KEY958812, Union Vale, NY 12585

  Ideal 12+ acre home site, near the iconic Millbrook Village. This level fertile land features an existing pond and privacy being at the end of a cul-de-sac. This property is Board of Health approved for a four bedroom home (no filled required). Create your own country farm estate. Make an inspection visit today!

  Robert D Ferris R. Ferris Real Estate, LLC

  0 Deer Pond Rd Unit KEY958812, Union Vale, NY 12585
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  $699,900

  $29K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 1,196 Sq Ft

  676-678 Oak Summit Rd, Millbrook, NY 12545

  Escape to this private retreat sited on 1.5 acres, on a country road, minutes to the Village of Millbrook. Imagine what you could do with this property. The two separate structures offer endless possibilities. The huge barn, with a garage below, which can accommodate 8+ cars, is perfect for a car enthusiast or other hobbyist, also includes a 1900 square foot, three bedroom, two-bath finished

  Lori Rheingold Houlihan Lawrence Inc.

  676-678 Oak Summit Rd, Millbrook, NY 12545
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  /23

  $799,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  991 Freedom Rd, Pleasant Valley, NY 12569

  TO BE BUILT – The Vanderbilt Model Colonial on Over 3 Acres!This stunning 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance and functionality. The thoughtfully designed main level features a formal living room and dining room, a spacious family room that showcases a gas fireplace and a wall of windows, seamlessly opening to the kitchen with quartz counters, a center island,

  John Gabriel Jr KW MidHudson

  991 Freedom Rd, Pleasant Valley, NY 12569
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  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 3,920 Sq Ft

  49 Barkit Kennel Rd, Pleasant Valley, NY 12569

  Rare and extraordinary custom built private estate nestled on 43 private acres in the heart of Pleasant Valley. Surrounded by rolling woodlands and breathtaking natural beauty, this exceptional residence offers an unparalleled blend of timeless elegance, refined craftsmanship, and resort-style living. Whether you're seeking a luxurious full-time residence, an executive retreat, or a secluded

  Justin Phillips United RE Hudson Valley Edge

  49 Barkit Kennel Rd, Pleasant Valley, NY 12569
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  /16

  $899,000

  • Land
  • 49.36 Acres
  • $18,213 per Acre

  0 Mallory Rd Unit KEY1016545, Union Vale, NY 12585

  Nearly 50 acres of enchanted woodland in the heart of Clove Valley, just minutes from the Village of Millbrook and within the Millbrook Central School District. Meandering trails wind through mature forest, past centuries-old stone walls and a picturesque pond, opening to sweeping countryside and distant Catskill views. A place of extraordinary beauty and complete privacy, where every season

  DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

  0 Mallory Rd Unit KEY1016545, Union Vale, NY 12585
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  /22

  $665,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  12 Ciferri Dr, Millbrook, NY 12545

  Welcome to this charmer located right in the Village of Millbrook and set on one acre of beautifully landscaped land with magnificent specimen trees and a covered patio that invites one to cook, eat or just sit and admire the lush property. Abundant light streams through this cape style home which features a handsome eat-in kitchen with all modern appliances and gleaming granite counters, a

  SHARON MAHAR Compass Greater NY, LLC

  12 Ciferri Dr, Millbrook, NY 12545
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  $1,250,000

  New Construction Open Sat 1PM - 3:30PM

  • 4 Beds
  • 3.5 Baths
  • 3,196 Sq Ft

  43 Maple Hill Dr, Millbrook, NY 12545

  New home under construction featuring a primary bedroom on the first level, high-end finishes, and exceptional attention to detail throughout. A two-story foyer with arched entry welcomes you to the formal living room, dining room, and the seamlessly connected kitchen and family room. Beautiful white oak flooring spans the entire first level, and the thoughtfully designed layout provides the

  TINA TOWNSEND BHHS Hudson Valley Properties

  43 Maple Hill Dr, Millbrook, NY 12545
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  $1,100,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,300 Sq Ft

  129 Clinton Corners Rd, Salt Point, NY 12578

  Set behind a sweeping driveway canopied by pear trees in bloom, this extraordinary post-and-beam contemporary is a study in what privacy truly looks like — 18.5 acres of curated landscape, forest trails, and open sky, ten minutes from the Taconic State Parkway. The architecture announces itself immediately: soaring 25-foot cathedral ceilings, a commanding central stone fireplace, and grand

  Ryan Arket Compass Greater NY, LLC

  129 Clinton Corners Rd, Salt Point, NY 12578
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  /15

  $184,900

  • 2 Beds
  • 1 Bath
  • 1,098 Sq Ft

  4 Wilbur Rd, Pleasant Valley, NY 12569

  DIAMOND IN THE ROUGH! HUGE POSSIBILITIES! RANCH HOME TWO BEDROOM, OFFICE OR NURSERY, DEN, LIVINGROOM. EAT IN KITCHEN WITH SLIDERS TO HUGE DECK. SPACIOUS ROOMS. BASEMENT AND WORKSHOP. PRIVATE YARD. ENJOY BACK YARD CREEK VIEWS.MATURE LANDSCAPING. CONVENIENT TO EASTDALE VILLAGE AND ALL AMENITIES. MIN. TOTSP AND TRAIN. WAPPINGERS CREEK FOR FISHING. KAYAKING AND SUMMER FUN.

  Angela Kern BHHS Hudson Valley Properties

  4 Wilbur Rd, Pleasant Valley, NY 12569
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  $1,495,000

  • 4 Beds
  • 3 Baths
  • 3,228 Sq Ft

  508 Woodstock Rd, Millbrook, NY 12545

  Set along a country road just beyond the Village of Millbrook, this cedar-sided traditional overlooks a serene, spring-fed pond and unfolds across 23 acres of rolling fields, mature trees, and thoughtfully kept grounds. The setting feels both expansive and private, with long views and a true sense of escape. The 3,200+ square foot home offers a spacious and flexible layout, with four bedrooms,

  Oliver Brown Houlihan Lawrence Inc.

  508 Woodstock Rd, Millbrook, NY 12545
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  /49

  $699,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  394 Smith Rd, Hyde Park, NY 12538

  Welcome to 394 Smith Rd. A sprawling Mid-Century Ranch on Nearly 10 Acres with Pond & Panoramic Views. Set on nearly 10 private acres, this picturesque sprawling ranch offers true one-level living with breathtaking 360-degree views, including stunning sunrises and sunsets. Tucked back from the road and elevated for maximum privacy, this special property blends natural beauty and charm.The

  LISA WOHLMUTH KW MidHudson

  394 Smith Rd, Hyde Park, NY 12538
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  /40

  $799,900

  • 3 Beds
  • 2.5 Baths
  • 2,595 Sq Ft

  137 Old Camby Rd, Verbank, NY 12585

  Privately set on a lovely country lane, this charming residence is the perfect retreat. The post and beam design fits well into its surroundings, nestled in the midst of 4.1 acres of nature and woodlands. Comfort abounds in this inviting home with a rustic feel, pleasantly designed with open, airy spaces. With nearly 2600 square feet, it boasts three bedrooms, a first floor den or home office, 2

  Susan Whalen George T Whalen Real Estate

  137 Old Camby Rd, Verbank, NY 12585

Showing Results 41 - 71, Page 2 of 2