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Homes for Sale in 12545

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  • /35

    $1,400,000

    • 3 Beds
    • 8 Baths
    • 10,689 Sq Ft

    4258 Route 44, Millbrook, NY 12545

    This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring

    Stephen Pener William Pitt Sothebys Int Rlty

    4258 Route 44, Millbrook, NY 12545
  • /9

    $995,000

    • Land
    • 23.49 Acres
    • $42,358 per Acre

    Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545

    Located just outside the Village of Millbrook on a scenic gravel country road, Old Oaks Woods is a 23.49-acre parcel offering a picturesque setting for your dream retreat. The land features a mix of old-growth forest and walking trails, bordered by charming stone walls and highlighted by a pair of peaceful ponds. A large barn and chicken coop remain on the property. Build your private weekend

    OLIVER BROWN Houlihan Lawrence Inc.

    Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545
  • /23

    $639,000

    $56K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft

    3875 Route 82, Millbrook, NY 12545

    Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway.Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living.Upstairs includes full, eat in kitchen, dining

    Valerie Foster K. Fortuna Realty, Inc.

    3875 Route 82, Millbrook, NY 12545
  • /33

    $11,500,000

    • 5 Beds
    • 6.5 Baths
    • 6,054 Sq Ft

    129 W Meadow Ln, Millbrook, NY 12545

    Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance

    Candy Anderson Compass Greater NY, LLC

    129 W Meadow Ln, Millbrook, NY 12545
  • /24

    $895,000

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,136 Sq Ft

    35 Appaloosa Ln, Millbrook, NY 12545

    Perfectly situated at the end of a long driveway and enjoying complete privacy is this four bedroom Ranch on 8.94 +/- acres offering a picturesque setting and located only minutes to the Village of Millbrook. The lovely interior features an open floor plan with many fine details throughout such as Anderson windows, custom trim and hardwood floors. The spacious open country Kitchen is fully

    Carey Whalen Compass Greater NY, LLC

    35 Appaloosa Ln, Millbrook, NY 12545
  • /9

    $1,050,000

    • Land
    • 28.43 Acres
    • $36,933 per Acre

    TBD Woodstock Rd, Millbrook, NY 12545

    Quiet Meadow South – A rare offering of 28.43 acres of open land at the corner of Stanford Road and Woodstock Road. Bucolic field, a corner pond, and distant views create a stunning backdrop for a future homestead or agricultural endeavor. Located just outside the Village of Millbrook, this scenic parcel offers easy access with the feel of wide-open countryside. Additional land available.

    OLIVER BROWN Houlihan Lawrence Inc.

    TBD Woodstock Rd, Millbrook, NY 12545
  • /26

    $16,500,000

    • 4 Beds
    • 8 Baths
    • 7,500 Sq Ft

    365 Tower Hill Rd, Wassaic, NY 12592

    Introducing Sky House. This 7,500-square-foot modern estate atop 138 acres of meadows, woodland, and rolling hills in Millbrook’s storied hunt country is a study in serenity and design intelligence. Conceived by the celebrated firm Resolution: 4 Architecture and completed in 2019, the residence rises from the landscape with a long, linear silhouette tempered by floor-to-ceiling glass that invites

    Ashley Whittaker Spence Compass Greater NY, LLC

    365 Tower Hill Rd, Wassaic, NY 12592
  • /16

    $950,000

    • 4 Beds
    • 2 Baths
    • 3,005 Sq Ft

    41 Flint Rd, Millbrook, NY 12545

    Welcome to The Flint Road Retreat!! Beautifully maintained one-owner ranch situated on 3.53 private acres along a quiet country road, this property offers a peaceful and serene setting with plenty of room to enjoy the surrounding natural beauty, while remaining just minutes from local shops, restaurants and area amenities. The home features stunning hardwood floors, custom cherry cabinetry,

    AURA QUARTARARO William Pitt Sothebys Int Rlty

    41 Flint Rd, Millbrook, NY 12545
  • /50

    $725,000

    $150K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    568 Oak Summit Rd, Millbrook, NY 12545

    Millbrook Modern Log Retreat sited on Nearly 3.5 Secluded Acres. Set quietly amid rolling landscape and enveloped by nature, this exquisitely restored log residence offers a rare blend of rustic authenticity and modern refinement. Perched on a knoll, the home unfolds as a serene escape—thoughtfully reimagined to deliver both comfort and understated luxury. From the moment you enter, the interiors

    Nicole Porter Houlihan Lawrence Inc.

    568 Oak Summit Rd, Millbrook, NY 12545
  • /50

    $5,500,000

    New Construction
    • 4 Beds
    • 5.5 Baths
    • 6,244 Sq Ft

    3585 Route 82, Millbrook, NY 12545

    Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined

    Jordan Vaccaro Serhant LLC

    3585 Route 82, Millbrook, NY 12545
  • /6

    $944,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,829 Sq Ft

    37 Maple Hill Dr, Millbrook, NY 12545

    This to-be-built Mayfair style home will be located in Hidden Glen, Millbrook's newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level, tree-lined homesites. This popular design offers 2,829 square feet of beautifully crafted living space and upscale finishes throughout. A grand two-story entry foyer leads to an open kitchen and breakfast area overlooking the

    TINA TOWNSEND BHHS Hudson Valley Properties

    37 Maple Hill Dr, Millbrook, NY 12545
  • /40

    $1,069,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,001 Sq Ft

    45 Maple Hill Dr, Millbrook, NY 12545

    Introducing the first home in Hidden Glen, Millbrook's Newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level tree-lined homesites. This Millbrook Design offers 3,001 square feet of expertly crafted living space, featuring custom design and upscale finishes throughout. Located within the highly regarded Millbrook School District, this elegant new construction

    TINA TOWNSEND BHHS Hudson Valley Properties

    45 Maple Hill Dr, Millbrook, NY 12545
  • /6

    $954,000

    • 3 Beds
    • 2 Baths
    • 2,030 Sq Ft

    66 County House Rd, Millbrook, NY 12545

    To Be Built. Introducing Millbrook's newest luxury community, Hidden Glen at Millbrook, offering eight custom residences set on gorgeous one+ acre, level tree-lined homesites. The Rochester ranch-style home is positioned on a premium lot and offers 2,030 square feet of convenient one-level living. The foyer opens to a dramatic family room with volume ceilings, flowing seamlessly into the kitchen

    Brian Mossey BHHS Hudson Valley Properties

    66 County House Rd, Millbrook, NY 12545
  • /31

    $65,000,000

    • 10 Beds
    • 8 Baths
    • 14,706 Sq Ft

    45 Hitchcock Ln, Millbrook, NY 12545

    The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer

    HEATHER CRONER William Pitt Sothebys Int Rlty

    45 Hitchcock Ln, Millbrook, NY 12545
  • /34

    $385,000

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    884 Camby Rd, Millbrook, NY 12545

    Estate property being sold AS, including contents. 5+/-acre parcel of lovely land with meadows, views of rolling hill tops and majestic trees. There is an old growth of grape vines and an orchard with various fruit trees. A truly special piece of property conveniently located to communte to NYC either by car or train. Just the land and improvements alone proof the value of this offering. The

    Amy Levine Howard Hanna Rand Realty

    884 Camby Rd, Millbrook, NY 12545
  • /20

    $4,495,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 5,679 Sq Ft

    101 N Tower Hill Rd, Millbrook, NY 12545

    **TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort,

    Ronald Green KW MidHudson

    101 N Tower Hill Rd, Millbrook, NY 12545
  • /30

    $720,000

    • 3 Beds
    • 3 Baths
    • 1,986 Sq Ft

    3881 U S 44, Millbrook, NY 12545

    This cozy shingle style cottage is set on top of a daffodil freckled hill in the middle of the Millbrook hunt country. It has been remodeled giving it a more modern feel, increased light and views of hills, valley and farms. All the windows on the first floor have been replaced as has the roof, furnace, water heater and UV system. The terrace has been re-pointed and and an enclosed garden with

    CATHERINE HOWARD Corcoran Country Living - Mill

    3881 U S 44, Millbrook, NY 12545
  • /45

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,706 Sq Ft

    22 Haight Ave, Millbrook, NY 12545

    Charming Cape Cod style home with thoughtful updates and wonderful natural light throughout. The first floor features a fully renovated kitchen with a cheerful breakfast bar, a living room with wood-burning fireplace, a sunroom overlooking the lovely backyard, a full bathroom, a bedroom, and an office. Upstairs, you will find another well-proportioned bedroom, a second full bath and a large

    Susan Whalen George T Whalen Real Estate

    22 Haight Ave, Millbrook, NY 12545
  • /45

    $850,000

    $50K PRICE DROP
    • 4 Beds
    • 6.5 Baths
    • 5,050 Sq Ft

    3534 Route 82, Millbrook, NY 12545

    Discover a truly unique Millbrook estate set on over 6 acres with a private pond, fruit trees, and beautiful natural surroundings. This expansive stone and brick residence offers remarkable craftsmanship and imported finishes, including marble and other materials brought in directly from Italy. Designed for both elegance and comfort, the home features multiple kitchens, two formal dining rooms,

    Christian Baez KW Hudson Valley United

    3534 Route 82, Millbrook, NY 12545
  • /49

    $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
  • /33

    $3,500,000

    • 4 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
  • /32

    $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
  • /39

    $575,000

    $74K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,576 Sq Ft

    6 Route 343, Millbrook, NY 12545

    Owner listening to all offers. 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

    Rebecca Marino Corcoran Country Living

    6 Route 343, Millbrook, NY 12545
  • /36

    $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
  • /37

    $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 property! Set on

    Ann Stettner Neil Charles Real Estate, LLC

    3311 Franklin Ave, Millbrook, NY 12545
  • /38

    $729,000

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    676-678 Oak Summit Rd, Millbrook, NY 12545

    Your dream awaits. Escape to this private retreat sited on 1.5 acres, on a quiet country road, minutes to the Village of Millbrook. This property offers endless possibilities. The detached barn/garage can accommodate 8+ cars and includes a 1900 square foot, three-bedroom, two bath, finished space above. If you are a car enthusiast searching for an oversized garage with space to store 8+ cars,

    Lori Rheingold Houlihan Lawrence Inc.

    676-678 Oak Summit Rd, Millbrook, NY 12545
  • /36

    $374,900

    • 3 Beds
    • 2 Baths
    • 4,072 Sq Ft

    646 Oak Summit Rd, Millbrook, NY 12545

    Discover a unique and rare opportunity in this sprawling ranch-style 2-family home with generous space, flexible layout, and charming character— ready for your renovations and visions. Set on a picturesque 1.7-acre corner lot with an expansive yard, gazebo, shed, mature landscaping, the potential of this home welcomes a serene Hudson Valley lifestyle.The upper unit features over 2,000 sq. ft.

    LISA WOHLMUTH KW MidHudson

    646 Oak Summit Rd, Millbrook, NY 12545
  • /36

    $720,000

    • 2 Beds
    • 3 Baths
    • 1,986 Sq Ft

    3881 Route 44, Millbrook, NY 12545

    This cozy shingle style cottage is set on top of a daffodil freckled hill in the middle of the Millbrook hunt country. It has been remodeled giving it a more modern feel, increased light and views of hills, valley and farms. All the windows on the first floor have been replaced as has the roof, furnace, water heater and UV system. The terrace has been re-pointed and and an enclosed garden with

    CATHERINE HOWARD Corcoran Country Living

    3881 Route 44, Millbrook, NY 12545
  • /9

    $1,250,000

    New Construction
    • 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
  • /46

    $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
  • /35

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,480 Sq Ft

    50 Horseshoe Rd, Millbrook, NY 12545

    Welcome to this Contemporary Raised Ranch set on 1.52 acres in the Millbrook area, just minutes to the Village. Offering 2,480 finished square feet, the home has been thoughtfully updated to combine modern finishes with a practical, well-designed layout that flows with ease. The main level features a bright, inviting living area enhanced by a fresh coat of paint throughout, an updated kitchen

    STEVEN WROBEL JR. Serhant LLC

    50 Horseshoe Rd, Millbrook, NY 12545
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