Dutchess County NY Homes for Sale with Private Pool

/36
$5,500,000
- 7 Beds
- 5 Baths
- 6,019 Sq Ft
20 Smithfield Way, Amenia, NY 12501

Set on 53+ Bucolic acres in the heart of the Hudson Valley, Smithfield Farm is an exquisite estate, offering breathtaking, sweeping western views of the Smithfield Valley and the Catskill mountains. The centerpiece of the estate is a meticulously preserved 1790 Colonial main house with a stately brick exterior and a grand center hall. Inside, you will find four woodburning fireplaces, central air

OLIVER BROWN Houlihan Lawrence Inc.

20 Smithfield Way, Amenia, NY 12501
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/65
$1,750,000
- 6 Beds
- 2 Baths
- 3,000 Sq Ft
831 Wolcott Ave, Beacon, NY 12508

Experience a rare blend of historic charm and modern luxury in this graceful circa 1900 Dutch Colonial Revival, nestled just minutes from Beacon's lively Main Street.Six spacious bedrooms and two full bathrooms, ideal for comfortable family living or hosting guests.Original period details: Soaring ceilings, restored hardwood floors creaking gently underfoot, intricate woodwork, and

Nicola Friedman Windsor Realty Services, Inc.

831 Wolcott Ave, Beacon, NY 12508
/39
$483,976
- 3 Beds
- 1 Bath
- 2,094 Sq Ft
137 S Highland Rd, Wappingers Falls, NY 12590

Welcome to 137 S Highland Rd, a distinctive 1938-built residence that masterfully blends rustic charm with contemporary comfort across 2,094 square feet. Situated on nearly an acre in Wappingers Falls, this three-bedroom, one-bath home offers a rare combination of classic architectural character and modern amenities that appeal to buyers seeking authentic style without sacrificing today's

Jules Zaphire Locqube New York, Inc.

137 S Highland Rd, Wappingers Falls, NY 12590
/16
$550,000
- 3 Beds
- 1.5 Baths
- 1,170 Sq Ft
25 Orchard Dr, Wappingers Falls, NY 12590

Pool area (enclosed by fence), garage.

Jose Abeijon Irene G. DaSilva Real Estate

25 Orchard Dr, Wappingers Falls, NY 12590
/31
$599,999
- 2 Beds
- 2.5 Baths
- 1,902 Sq Ft
4034 Chestnut Ridge Rd Unit 62, Fishkill, NY 12524

Why wait to build when this stunning, newly constructed townhome is ready now — with all the upgrades already done? Built in 2025, this beautifully designed home offers modern living at its finest, featuring recessed lighting and rich wood floors throughout — including the bedrooms — creating a seamless and elevated feel. The heart of the home is a tastefully appointed kitchen with a large center

Susan McMullen eXp Realty

4034 Chestnut Ridge Rd Unit 62, Fishkill, NY 12524
/12
$389,000
- 2 Beds
- 1.5 Baths
- 1,187 Sq Ft
508 Somerset Ct, Fishkill, NY 12524

Two bedroom townhouse with beautiful hardwoods floors throughout. Newer Stainless steel appliances , lots of cabinets and large pantry are some of the great features to this home. Unit is in very good condition but could use a little updating which is reflected in the price. But there is nothing home needs but a little bit of fresh paint. Full bath upstairs features separate walk in shower and

Toni Scalici Asset Property Realty Services

508 Somerset Ct, Fishkill, NY 12524
/42
$13,500,000
- 5 Beds
- 8 Baths
- 5,867 Sq Ft
1190 Chestnut Ridge Rd, Dover Plains, NY 12522

A singular and exceedingly rare residence, this exquisite home was masterfully designed by renowned AD100 architect Gil Schafer, featuring interiors by Antony Todd and landscape architecture by Warren Byrd, all set against panoramic views of the Hudson Valley and Catskill Mountains. This home is a Greek Revival masterpiece that blends timeless elegance with modern sophistication. As featured in

OLIVER BROWN Houlihan Lawrence Inc.

1190 Chestnut Ridge Rd, Dover Plains, NY 12522
/38
$750,000
- 3 Beds
- 2 Baths
- 1,548 Sq Ft
104 S Quaker Ln, Hyde Park, NY 12538

A unique opportunity to own a charming, historic one-family home on an expansive parcel of land in the desirable Hyde Park area of Dutchess County. This property offers privacy and space, perfect for those seeking a tranquil country lifestyle while remaining close to local amenities. Situated on a substantial 25.43-acre lot with RA (Rural Residence) zoning, the property features a mix of open

Luis Gordillo Schunk Realty Group

104 S Quaker Ln, Hyde Park, NY 12538
/34
$499,000
- 4 Beds
- 1.5 Baths
- 1,362 Sq Ft
201 Linden Ave, Red Hook, NY 12571

Once in a generation does a home like this come available. Meticulously cared for by the previous family; this Red Hook gem features a fabulous floor plan. One level easy living and a full finished basement with room for so much expansion. Walk in through the breezeway with blue stone floors and walls of windows, perfect for a grand entry way or lounge area to have a sunlight morning cup of

Chelsea Pollard-Seiler Mondello Upstate Properties

201 Linden Ave, Red Hook, NY 12571
/18
$524,950
- 3 Beds
- 2.5 Baths
- 1,967 Sq Ft
733 Huntington Dr, Fishkill, NY 12524

Welcome to Toll Brothers Luxury Homes. This Bainbridge Model offers the perfect blend of comfort and style, featuring three spacious bedrooms. The primary bathroom boasts an upgraded, spectacular walk-in California-style closet, and two other generously sized bedrooms provide ample space for relaxation and privacy. Two and a half bathrooms; the primary bathroom features a Roman tub, a secondary

Marion McKinley K. Fortuna Realty, Inc.

733 Huntington Dr, Fishkill, NY 12524
/44
$600,000
- 3 Beds
- 4 Baths
- 2,853 Sq Ft
1123 Cold Spring Rd, Fishkill, NY 12524

Prime Fishkill location! Built by Toll Brothers, this sought-after Bainbridge model offers 2,853 square feet of well-designed living space on 3 levels with 3 bedrooms, 2 full and 2 half baths. The thoughtful upgrades enhance both comfort and style in this classic Townhome located in Van Wyck Meadows. The main level features custom moldings and rich cherry floors that run throughout, creating a

Debra Allan BHHS Hudson Valley Properties

1123 Cold Spring Rd, Fishkill, NY 12524
/50
$699,000
- 4 Beds
- 3.5 Baths
- 4,208 Sq Ft
19 Ridgeview Rd, Poughkeepsie, NY 12603

Nestled in complete privacy on 3.25 acres and surrounded by nature, this extraordinary mid-century modern home offers some of the most spectacular views you’ll find anywhere in the Hudson Valley. Designed to embrace light, space, and scenery, this 4 bedroom, 3.5 bath retreat perfectly blends timeless architecture with modern comfort. Gleaming hardwood floors and beamed ceilings highlight the

Jennifer Amicucci

19 Ridgeview Rd, Poughkeepsie, NY 12603
/3
$550,000
- 4 Beds
- 2.5 Baths
- 2,456 Sq Ft
147 Mayfair Rd, Poughquag, NY 12570

Four bedroom home, just waiting for your personal touch. Large family room with access to deck . Beautiful seasonal mountain views. Some updating and repairs needed which is reflected in the price. House has a above ground pool, but hasn't been opened in three years. Owner states pool pump may need some work. Some boards on deck need to be placed so owner is asking to not go on deck with all the

Toni Scalici Asset Property Realty Services

147 Mayfair Rd, Poughquag, NY 12570
/34
$629,000 Open Sat 11AM - 2PM
- 3 Beds
- 2.5 Baths
- 2,037 Sq Ft
45 Lewis Rd, East Fishkill, NY 12533

Nestled in a secluded, highly desirable community in Hopewell Junction, this impeccably maintained luxury townhouse offers over 2,100 sq ft of sophisticated living with 3 bedrooms, 3 full baths, gleaming hardwood floors, a gourmet kitchen featuring granite and marble countertops, two-zone central air conditioning, a brand-new water heater (2024), and a private manicured backyard with patio. Enjoy

Faisal Faisal Faze One Real Estate, LLC

45 Lewis Rd, East Fishkill, NY 12533
/18
$3,995,000
- 3 Beds
- 2 Baths
- 5,000 Sq Ft
3362 New York 199, Pine Plains, NY 12567

. To-Be-Built Luxury Estate with Infinity Pool & Panoramic Catskill Views – Pine Plains, NY. Elevated high above the valley floor with sweeping, unobstructed Catskill Mountain views, this to-be-built custom estate is a rare opportunity in the heart of the Hudson Valley. Set on an extraordinary piece of land—offering total privacy and dramatic natural beauty—this 5,000+ square foot residence is

Michael Lund Corcoran Country Living

3362 New York 199, Pine Plains, NY 12567
/38
$469,000
- 2 Beds
- 2 Baths
- 852 Sq Ft
15 E Dogwood Dr, Poughkeepsie, NY 12601

Don’t miss your chance to own this charming home in the desirable Town of Poughkeepsie, nestled within the top-rated Spackenkill School District. Perfectly updated and move-in ready, this home combines cozy living with modern conveniences — making it ideal for both relaxation and entertaining.Step inside to a bright and airy living room that flows effortlessly into the newly remodeled

Lisa DiMarzio BHHS Hudson Valley Properties

15 E Dogwood Dr, Poughkeepsie, NY 12601
/50
$289,888
- 3 Beds
- 1.5 Baths
- 1,729 Sq Ft
3 Hook Rd Unit 32, Poughkeepsie, NY 12601

This spacious three level townhouse has full basement walk-out located at The Arbors condo. Freshly painted interiors, hardwood floors in the Living room & Dining room. Eat-in kitchen with built-in seating & storage. Formal Dining Room has sliders to deck. Oversized Primary bedroom with 2 walk-in closets. 2nd bedroom has walk-in closet and single closet. 3rd bedroom has built in bunk bed.

Frances Chiu Realty Center Hudson Valley

3 Hook Rd Unit 32, Poughkeepsie, NY 12601
/47
$624,900
- 4 Beds
- 4 Baths
- 3,250 Sq Ft
90 Cedar Ave, Poughkeepsie, NY 12603

You could be living the dream on Poughkeepsie’s south side! Enjoy one level living in this expanded ranch with a Mid Century Modern vibe. The striking design harmoniously blends with nature, creating a private outdoor retreat. Situated on 1.5 acres with an in-ground pool, this home offers 4 bedrooms, 2 full and 2 half baths. This home perfectly balances space and privacy for you and your nearest

Pamela Kandel

90 Cedar Ave, Poughkeepsie, NY 12603
/22
$599,000
- 3 Beds
- 1 Bath
- 988 Sq Ft
425 Spring Lake Rd, Red Hook, NY 12571

Discover the untapped potential of this charming three-bedroom, one-bath cottage, complete with a barn and garden, set on 19 captivating acres in the heart of the Hudson Valley. Nestled along the peaceful shores of Spring Lakea private, spring-fed haven reserved exclusively for residentsthis unique property offers a harmonious blend of tranquility and opportunity.Winding stone walls and dramatic

SHERI SCEROLER Four Seasons Sotheby's Int.

425 Spring Lake Rd, Red Hook, NY 12571
/29
$705,000
- 4 Beds
- 3 Baths
- 3,888 Sq Ft
12 Rebecca Dr, Pawling, NY 12564

Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

Kevin Sanabria eRealty Advisors, Inc

12 Rebecca Dr, Pawling, NY 12564
/35
$2,600,000
- 3 Beds
- 6 Baths
- 2,614 Sq Ft
188 Nine Partners Ln, Millbrook, NY 12545

This 1800’s Millbrook farmhouse has been totally renovated to today’s buyers wishes and needs featuring an open floor plan for the kitchen and dining area with three sets of French doors opening to a porch and the new outdoor kitchen pavilion and pool house equipped with kitchenette and powder room. A light filled three season sunporch offers views of the meadow. The formal living room and den

ANN WILKINSON Compass Greater NY, LLC

188 Nine Partners Ln, Millbrook, NY 12545
/13
$580,000
- 4 Beds
- 3 Baths
- 2,006 Sq Ft
16 Lenny Ct, Wappingers Falls, NY 12590

Set on a quiet cul-de-sac, this well-maintained home offers space, privacy, and a layout designed for everyday living and entertaining. The home features 4 bedrooms with 2 walk-in closets, 3 full renovated bathrooms, a separate laundry room with washer and dryer hookup, and an attached garage. Generous room sizes and a functional floor plan provide flexibility throughout. Sliding doors lead to a

Jose Cruz Douglas Elliman Real Estate

16 Lenny Ct, Wappingers Falls, NY 12590
/26
$569,900
- 2 Beds
- 2.5 Baths
- 1,902 Sq Ft
4044 Chestnut Ridge Rd, Fishkill, NY 12524

Brand new and never lived in, this luxurious two-bedroom townhouse is located in the desirable Van Wyck Mews community in Fishkill. This popular design includes a separate study that functions perfectly as a third bedroom or home office. Enjoy an open concept layout featuring a spacious living room, dining room, and breakfast area that flows seamlessly into the designer kitchen. The kitchen

TINA TOWNSEND BHHS Hudson Valley Properties

4044 Chestnut Ridge Rd, Fishkill, NY 12524
/50
$1,495,000
- 3 Beds
- 3 Baths
- 1,723 Sq Ft
31 Blueberry Ln, Stormville, NY 12582

Welcome to 31 Blueberry Lane in Stormville, a unique estate offering two homes and a guest studio on over 17 private acres with stunning natural features, including two ponds and an inground pool. The primary residence is a 3-bedroom, 3-bathroom home designed for comfort and entertaining, featuring a large living area with modern windows and exterior doors, an efficient heating and cooling system

STEVEN WROBEL JR. Serhant LLC

31 Blueberry Ln, Stormville, NY 12582
/44
$619,000
- 4 Beds
- 3 Baths
- 2,350 Sq Ft
35 Rapalje Rd, Fishkill, NY 12524

Welcome to 35 Rapalje Rd- A Charming Village Retreat Nestled in Fishkill. Discover the perfect blend of character, comfort, and location. With its classic cape-style design, this home has been completely renovated while retaining its vintage charm with no expense spared. 1st floor bedroom with a full bathroom is just one of its many attributes. Upstairs has 3 additional bedrooms and two full

Owais Khan OXM Realty Group LLC

35 Rapalje Rd, Fishkill, NY 12524
/35
$6,995,000
- 3 Beds
- 4.5 Baths
- 6,216 Sq Ft
151 Rowe Rd, Red Hook, NY 12571

Crestline is a visionary to-be-built residence offering 6,216 finished square feet of meticulously designed living space, including three bedroom suites and four-and-a-half luxurious baths. Pricing has been thoughtfully recalibrated to reflect the finalized construction scope and delivery approach, presenting an exceptional opportunity to secure a landmark Hudson Valley residence with enduring

Sean Eidle BHHS Hudson Valley Properties

151 Rowe Rd, Red Hook, NY 12571
/50
$1,999,999
- 7 Beds
- 7 Baths
- 11,222 Sq Ft
3893 Route 82, Millbrook, NY 12545

Set on 11.1 private acres in the heart of Millbrook, this stately brick Colonial estate offers over 11,222 square feet of refined living space, combining timeless elegance with exceptional versatility. A true legacy property, it delivers the scale, design, and amenities expected by the most discerning buyers. A dramatic two-story granite foyer welcomes you with a sweeping double staircase and a

Howard Payson RE/MAX Town & Country

3893 Route 82, Millbrook, NY 12545
/46
$39,000,000
- 9 Beds
- 15 Baths
- 55,000 Sq Ft
104 N Garden Dr, Pawling, NY 12564

Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

104 N Garden Dr, Pawling, NY 12564
/41
$2,875,000
- 7 Beds
- 6.5 Baths
- 5,486 Sq Ft
20 Orchard Hill Dr, Millbrook, NY 12545

Modern Country Retreat with Iconic Hudson Valley Views Proven Investment or Private Escape Seconds from Millbrook Experience refined country life in this beautifully updated Hudson Valley home, nestled on 12+ private acres with sweeping views of the Catskill Mountains. Surrounded by lush lawns, open meadows and a fenced paddock, the property offers a sense of serenity, space, and elevated

Kathryn Johnson William Pitt Sotheby's Interna

20 Orchard Hill Dr, Millbrook, NY 12545
/50
$1,375,000
- 3 Beds
- 2.5 Baths
- 2,820 Sq Ft
101 Drake Rd, Pleasant Valley, NY 12569

Tucked behind a quiet country approach, two meticulously restored 19th-century barns have been reimagined into a refined luxury residence and companion pool house that feel timeless in character and elevated in execution. Inside the main residence, soaring vaulted ceilings, original hand-hewn beams, and wide-plank floors establish a sense of warmth and permanence, while expansive walls of glass

Jake Garay Serhant LLC

101 Drake Rd, Pleasant Valley, NY 12569
/48
$995,000
- 4 Beds
- 3.5 Baths
- 3,888 Sq Ft
27 Gallagher Dr, Pleasant Valley, NY 12569

Salt Point / Clinton Corners | 5.6 Private Acres | Pool | Mountain Views Set on a quiet cul-de-sac just off Salt Point Turnpike in the desirable Salt Point / Clinton Corners corridor between Millbrook and Rhinebeck, this private Hudson Valley retreat offers convenience, seclusion, and sweeping mountain and valley views. Surrounded by farmland and mature trees, and just minutes to the Taconic

DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

27 Gallagher Dr, Pleasant Valley, NY 12569
/41
$595,000
- 3 Beds
- 2 Baths
- 2,254 Sq Ft
79 W Main St, Pawling, NY 12564

One of the prettiest homes you will see! Lovingly maintained home has all the original character and charm yet offers desired modern updates. Truly park-like property features a babbling brook, stone walls and perennial gardens. Special interior features throughout the home include solid hardwood floors, vintage doors with glass doorknobs, original trim work, all new windows, central air. A

Lisa Liffland McGrath Realty Inc

79 W Main St, Pawling, NY 12564
/42
$11,200,000
- 8 Beds
- 6 Baths
- 8,280 Sq Ft
40 Morton Rd, Rhinebeck, NY 12572

Stonecrest on the Hudson is a stunningly designed home on 16 inspiringly landscaped acres with extensive views of the river and the Catskills. A creation of stone, metal, and glass, the home, though imposing, inhabits its environment with seamless grace and is curated for comfort and meditative living. Many exquisite features make Stonecrest one-of-a-kind, impossible to duplicate. Upon approach,

Jill Rose Houlihan Lawrence Inc.

40 Morton Rd, Rhinebeck, NY 12572
/48
$3,750,000
- 3 Beds
- 5 Baths
- 4,134 Sq Ft
97 Valley Farm Rd, Millbrook, NY 12545

New, never lived in, move in ready, almost 20 acres, just outside the Village of Millbrook, stunning, fully remodeled total renovation (both inside and out), country property with the most gorgeous sweeping Catskill Mountain Views. No expense was spared. Pure luxury inside and out. Inside: All brand new: windows, doors, heating & cooling system, plumbing and electrical, water purification system,

Susan Whalen George T Whalen Real Estate

97 Valley Farm Rd, Millbrook, NY 12545
/35
$570,000
- 5 Beds
- 2 Baths
- 2,823 Sq Ft
56 Daley Rd, Poughkeepsie, NY 12603

Hudson Valley Haven – 56 Daley Rd, Poughkeepsie, NY Step into your private retreat in the heart of the Hudson Valley. This beautifully updated home offers the perfect blend of space, style, and comfort. The sun-filled main level features a cozy living room with a pellet stove, a dining area, a renovated kitchen with granite countertops and stainless steel appliances, and a four-season sunroom.

Jason Henry Keller Williams Hudson Valley

56 Daley Rd, Poughkeepsie, NY 12603
/39
$1,400,000
- 5 Beds
- 4 Baths
- 3,306 Sq Ft
645 Tyrrel Rd, Millbrook, NY 12545

Step back in time and experience this historic farm house which has been renovated with great attention to period details such as restored wide board flooring, beautiful reconditioned woodwork, exposed beams and 4 fireplaces. There are 5 bedrooms, one of which is ensuite and on the first floor ,and 3 other full baths. The primary is also ensuite.With formal living and dining rooms, office, and a

ANN WILKINSON Compass Greater NY, LLC

645 Tyrrel Rd, Millbrook, NY 12545
/51
$19,995,000
- 7 Beds
- 9 Baths
- 12,659 Sq Ft
309 Woodstock Rd, Millbrook, NY 12545

Presenting Canoe Hill, a remarkable 63-acre estate and vineyard in the heart of Millbrook, New York. This extraordinary property stands as a testament to architectural evolution, where a storied mid-1700s colonial core has been thoughtfully expanded to create a remarkable 12,650 SF main residence that seamlessly marries Colonial, Georgian and Greek Revival influences. Two significant expansions,

Jason Karadus Corcoran Country Living

309 Woodstock Rd, Millbrook, NY 12545
/35
$668,000
- 3 Beds
- 2.5 Baths
- 2,175 Sq Ft
3515 Bennington Dr, Fishkill, NY 12524

Welcome to the luxurious, maintenance-free lifestyle that is Van Wyck Mews! This Caufield Manor end unit is move-in ready and one of the few models to offer a beautifully finished basement featuring a spacious media room, tons of storage, and a roughed in third bath. Seller is sadly being relocated, so pricing below market value and even below what they paid...their great sacrifice is your prime

Susan Todd BHHS Hudson Valley Properties

3515 Bennington Dr, Fishkill, NY 12524
/44
$2,875,000
- 7 Beds
- 6.5 Baths
- 5,486 Sq Ft
20 Orchard Hill Dr, Millbrook, NY 12545

Modern Country Retreat with Iconic Hudson Valley Views Proven Investment or Private Escape Seconds from Millbrook Experience refined country life in this beautifully updated Hudson Valley home, nestled on 12+ private acres with sweeping views of the Catskill Mountains. Surrounded by lush lawns, open meadows and a fenced paddock, the property offers a sense of serenity, space, and elevated living—

Kathryn Johnson William Pitt Sothebys Int Rlty

20 Orchard Hill Dr, Millbrook, NY 12545
/47
$570,000
- 3 Beds
- 2 Baths
- 1,884 Sq Ft
5 Terra Nova Dr, Hopewell Junction, NY 12533

Welcome to this beautifully updated 3 bedroom home. Located in the heart of Hopewell and minutes to everything. Loving care shines through each room that has been kept pristine. So many windows allow lots of light to fill the whole house. This home boasts a huge living room with lots of storage. The kitchen comes equipped with a small walk in pantry and some newer appliances. A light filled four

SUZANNE NAKANO BHHS Hudson Valley Properties

5 Terra Nova Dr, Hopewell Junction, NY 12533

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