Dutchess County NY Homes for Sale with Pool

/36
$3,500,000
- 5 Beds
- 4.5 Baths
- 4,972 Sq Ft
0 Wing Rd, Washington, NY 12545

The artistry of Coole Park is in the way it unfolds from the center. Two gracious wings on either side of the original 1888 house create an architectural triptych that conveys elegance and comfort in equal measure. Warm wide board floors, soaring French doors, six working fireplaces, and numerous demi-lune windows create a sense of space and style as well as history. To the right of the entryway,

Candy Anderson Compass Greater NY, LLC

0 Wing Rd, Washington, NY 12545
/50
$419,000
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
44 Hurlihe St, Poughkeepsie, NY 12601

Where Riverfront Serenity Meets City-Smart Convenience in a True Turnkey Unit. Start every morning with coffee on your private deck, watching the sun rise over the Hudson as boats glide past and the river sparkles. Then—if you must- stroll less than 3 blocks to the Metro North station and be in Grand Central before your second cup.This rare, fully turnkey end unit offers front row river

Leigh Bahnatka BHHS Hudson Valley Properties

44 Hurlihe St, Poughkeepsie, NY 12601
/50
$2,150,000
- 7 Beds
- 7.5 Baths
- 7,720 Sq Ft
143 Bedell Rd, Poughkeepsie, NY 12603

Hilltop Retreat, built in the Millenium Mansion style, provides an incomparable experience of country living. This gracious residence is approached via a meandering driveway past stone walls and a pond and is secluded within 66 acres of curated lawns w/ majestic trees, a shimmering pond, old growth forest, and year-round Catskill mountain views. Casually formal, w/over 7,000sqft of living space

Eliane Abramoff Four Seasons Sothebys Intl

143 Bedell Rd, Poughkeepsie, NY 12603
/44
$500,000
- 4 Beds
- 3.5 Baths
- 2,425 Sq Ft
152 Bart Dr, Poughkeepsie, NY 12603

Deal Feel though-house fully available-Charming 4-Bedroom Home with Saltwater Pool in the Heart of LaGrangeLocated on a quiet no-outlet street in wonderful LaGrange, this lovingly maintained 4-bedroom, 3.1-bathroom home offers the perfect blend of space, comfort, and character. Featuring hardwood floors and many original details throughout, the home exudes warmth and timeless appeal. The

Nicole Porter

152 Bart Dr, Poughkeepsie, NY 12603
/38
$649,900
- 3 Beds
- 2.5 Baths
- 3,447 Sq Ft
107 Stony Brook Rd, Fishkill, NY 12524

Affordable Luxury! Come preview this gorgeous contemporary colonial built by the award winning luxury home builder Toll Brothers. Featuring over 3400 finished square feet and situated in the highly desired Van Wyck Glen subdivision, in the heart of Fishkill, a commuter’s dream location. This beautiful home offers unsurpassed value in today’s market. Highlights include: Spacious, contemporary

Lisa Sgobbo Century 21 Alliance Rlty Group

107 Stony Brook Rd, Fishkill, NY 12524
/42
$1,699,000
- 7 Beds
- 7 Baths
- 8,033 Sq Ft
125 Bedell Rd, Poughkeepsie, NY 12603

Timeless Elegance Meets Modern Comfort in the Heart of the Hudson Valley. Step into a world of refined charm and historic grandeur with this magnificent estate, originally constructed in 1867 and meticulously restored to preserve its legacy. Lovingly maintained over generations, the property blends classic architectural detail with the comforts of contemporary living, offering an unparalleled

Jillian Pajer Douglas Elliman Real Estate

125 Bedell Rd, Poughkeepsie, NY 12603
/34
$698,000
- 3 Beds
- 3 Baths
- 2,596 Sq Ft
354 Sunset Hill Rd E, Fishkill, NY 12524

Don't miss this incredible opportunity to live the vacation lifestyle every day. This unique log cabin offers a seamless blend of rustic charm and modern updates, set on three private acres with stunning mountainside views. The heart of the home is a beautifully updated open kitchen featuring an island, breakfast bar, two pantry closets, and direct access to the expansive full length

Jayne Morelock Howard Hanna Rand Realty

354 Sunset Hill Rd E, Fishkill, NY 12524
/26
$499,000
- 3 Beds
- 2.5 Baths
- 2,450 Sq Ft
6204 High Ridge Ct, Wappingers Falls, NY 12590

Modern 3 bed, 2.5 bath townhouse in a sought after community just outside the vibrant city of Beacon. This sun filled home features a sleek design, finished basement, and a one-car garage. Enjoy top notch amenities including a pool, basketball court, and clubhouse. Conveniently located near the Beacon train station, I-84, and the NY State Thruway, ideal for commuters and weekend getaways.

Jason Lysack K. Fortuna Realty, Inc.

6204 High Ridge Ct, Wappingers Falls, NY 12590
/32
$395,000
- 2 Beds
- 1.5 Baths
- 1,972 Sq Ft
18 Larch Ct, Fishkill, NY 12524

Fishkill, in the sought after Round Hill complex is a 2 bedroom, 1.5 bath End unit Townhome with one car garage waiting for you. With very low HOA! Enter into a spacious living room with brick fireplace and hand built bookshelves. Kitchen with stainless steel appliances and light wood cabinets. Large dining room with Anderson sliders to nice sized deck with room for a table and chairs to enjoy

Jean Ellen Baker RE/MAX Town & Country

18 Larch Ct, Fishkill, NY 12524
/49
$5,950,000
- 4 Beds
- 8 Baths
- 7,070 Sq Ft
141 Ackert Hook Rd, Rhinebeck, NY 12572

Located just 90 seconds from the heart of Rhinebeck Village and sited at the end of a long, boulder-lined drive, Fieldstone offers unparalleled privacy and proximity. A private oasis set on 31 acres, this masterfully crafted custom modern farmhouse is surrounded by open lawns, pastures, old-growth forest, historic stone walls, and a flowing stream. The light-filled great room dazzles with

Lindsay Allen Upstate Down

141 Ackert Hook Rd, Rhinebeck, NY 12572
/51
$19,995,000
- 7 Beds
- 9 Baths
- 11,970 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
/36
$600,000
- 3 Beds
- 3 Baths
- 2,224 Sq Ft
1056 Beekman Rd, Hopewell Junction, NY 12533

Welcome to 1056 Beekman Road—a beautifully updated Cape Cod where timeless charm meets resort-style living, set on over 3 acres.This home is full of character and thoughtful updates, featuring hardwood floors, exposed beams, and natural light throughout. The living room impresses with vaulted ceilings and a dramatic marble fireplace, creating a warm, welcoming space for cozy nights or

Corinna Deigan Compass Greater NY, LLC

1056 Beekman Rd, Hopewell Junction, NY 12533
/45
$895,000
- 4 Beds
- 4.5 Baths
- 5,445 Sq Ft
46 Duncan Rd, Lagrangeville, NY 12540

Stunning Custom Colonial in the heart of Beekman, Arlington Schools! Home features almost 5500 finished SQFT, 4 bedrooms, 4.5 baths, situated on just over an acre of privacy with tasteful updates throughout. First floor features a two-story grand foyer, formal living and dining rooms, oak floors throughout, 2-story great room with stone surround gas fireplace, custom chefs kitchen with SS

Justin LaFalce KW MidHudson

46 Duncan Rd, Lagrangeville, NY 12540
/36
$79,000
- 2 Beds
- 1 Bath
- 800 Sq Ft
191 Sylvan Lake Rd Unit 1, Hopewell Junction, NY 12533

Fully Renovated cottage has everything your looking for...come Findyourgetaway#. This seasonal cottage (May 1 - November 1) In the Sylvan Lake Area features a fenced in yard, private setting and perennial gardens. Can come minimally furnished as scene. Interior features new kitchen and bath updates, new floors, new lighting fixtures, fresh paint throughout and more. Laundry facility on site,

RYAN SCHWARZ

191 Sylvan Lake Rd Unit 1, Hopewell Junction, NY 12533
/50
$5,500,000
- 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
/45
$1,399,000
- 4 Beds
- 4.5 Baths
- 4,500 Sq Ft
145 Whalesback Rd, Red Hook, NY 12571

Welcome to this stunning colonial-style residence, beautifully situated on 6.26 acres in the scenic HudsonValley. This exceptional home greets you with a grand entrance, as pink cherry blossoms line thedriveway leading to a spacious three-car garage, while elegant Japanese Red Maples frame the street.Zoned for up to four horses, this private estate offers a perfect blend of charm and

Nancy Gaska Coldwell Banker American Homes

145 Whalesback Rd, Red Hook, NY 12571
/34
$1,525,000 Open Wed 11AM - 1:30PM
- 3 Beds
- 2.5 Baths
- 2,820 Sq Ft
101 Drake Rd, Pleasant Valley, NY 12569

CONVERTED BARNS WITH POOL. This charming getaway offers fun lofty spaces to gather, entertain and enjoy the countryside, while conveniently located to the TSP and Millbrook Village. This 19th century converted barn was beautifully preserved and showcases the exposed beams and wide board floors. Upon entering, one is enamored by the soaring vaulted ceilings with exposed beams in the center of the

PAULA REDMOND Corcoran Country Living

101 Drake Rd, Pleasant Valley, NY 12569
/50
$2,200,000
- 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
/50
$1,699,000
- 7 Beds
- 7 Baths
- 8,033 Sq Ft
125-127 Bedell Rd, Poughkeepsie, NY 12603

Timeless Elegance Meets Modern Comfort in the Heart of the Hudson Valley. Step into a world of refined charm and historic grandeur with this magnificent estate, originally constructed in 1867 and meticulously restored to preserve its legacy. Lovingly maintained over generations, the property blends classic architectural detail with the comforts of contemporary living, offering an unparalleled

Jillian Pajer Douglas Elliman Real Estate

125-127 Bedell Rd, Poughkeepsie, NY 12603
/21
$149,000
- 1.5 Baths
- 650 Sq Ft
160 Academy St Unit 5C, Poughkeepsie, NY 12601

**Bright & Comfortable Studio in Executive Towers – Prime Poughkeepsie Location**Welcome to this well-maintained 650 sq ft studio located in the desirable Executive Towers, a high-rise residence just minutes from Route 9, shopping, hospitals, local colleges, and the Poughkeepsie train station.This inviting space features hardwood floors in good condition, ample natural light, and functional

Shirley Mojica Compass Greater NY, LLC

160 Academy St Unit 5C, Poughkeepsie, NY 12601
/42
$759,900
- 4 Beds
- 2 Baths
- 1,880 Sq Ft
224 Fraleigh Ln, Red Hook, NY 12571

Country Cape on near end cul-de-Sac situate on 6 private acres , country kitchen with dining area ,LR with mason chimney pellet stove. double dutch door lead to4 season room, access to L shaped decking with jacuzzi, overlooking fire pit and landscaped yard and fenced in pool 16x36 area.Hardwd floors on main floor, and tile flrd baths ,4 Bedrooms,( 2 up, 2 down) 2 updated full baths (1

Karen Vetere Vetere, Karen Real Estate

224 Fraleigh Ln, Red Hook, NY 12571
/31
$455,000
- 3 Beds
- 2 Baths
- 2,052 Sq Ft
287 Norton Rd, Red Hook, NY 12571

Discover the perfect blend of comfort and seclusion in this charming 3- bedroom, 2-bath ranch, ideally set on a private, wooded lot with a picturesque pond. This home welcomes you with an open and airy floor plan, featuring a spacious living area filled with natural light and views of the surrounding landscape. Whether you're looking for a year-round residence or a serene weekend retreat, this

Amanda Wilcox eXp Realty

287 Norton Rd, Red Hook, NY 12571
/40
$459,000
- 2 Beds
- 1.5 Baths
- 1,376 Sq Ft
44 Vanderburgh Rd, Poughquag, NY 12570

Back On Market due to buyer financing! Welcome to this beautifully renovated 2-bedroom townhouse nestled in the highly sought-after Dalton Farm Community. The main level features an inviting, light-filled layout that flows seamlessly from room to room. The dining area opens through sliding glass doors to a spacious deck overlooking a serene and scenic shared backyard—perfect for relaxing or

Phil Risi KW MidHudson

44 Vanderburgh Rd, Poughquag, NY 12570
/46
$825,000
- 3 Beds
- 3.5 Baths
- 4,211 Sq Ft
66 Carol Ln, Poughquag, NY 12570

Welcome to this deluxe twelve room contemporary colonial, located 75 miles north of NYC, offering a perfect blend of classic charm and modern sophistication. The first floor features a grand two-story foyer, hardwood flooring, an expansive chef's kitchen with a large island and stainless steel appliances and seamless access to a private,wrap around deck and pool. Unforgettable living spaces

Helen Schweitzer Helen Schweitzer Realty, LLC

66 Carol Ln, Poughquag, NY 12570
/35
$1,179,000
- 3 Beds
- 2 Baths
- 2,700 Sq Ft
129 Clinton Corners Rd, Salt Point, NY 12578

129 Clinton Corners Road, Salt Point, NYA rare and exceptional offering—this private 18.5-acre estate blends natural beauty, architectural charm, and modern updates, all in a prime location just off the Taconic Parkway for easy commuting.This stunning post-and-beam 4,300 sq ft contemporary home features soaring 25-foot cathedral ceilings, a central stone wood-burning fireplace, and

Ginalea Healy K. Fortuna Realty, Inc.

129 Clinton Corners Rd, Salt Point, NY 12578
/9
$75,000
- 2 Beds
- 1 Bath
- 800 Sq Ft
191 Sylvan Lake Rd Unit 5, Hopewell Junction, NY 12533

Come and spend May 1st to November 1st in beautiful Dutchess County. This lovely 2 bedroom stand alone, cozy cottage/home is located in a private seasonal community. This home has an eat-in kitchen, new living room, newly renovated bathroom with heat lamp, a large screened in porch with plenty of storage in the full size attic. Porch newly painted. No need to worry about furniture, it comes

Elaine Delduca Judith Guzzi & Associates, LLC

191 Sylvan Lake Rd Unit 5, Hopewell Junction, NY 12533
/32
$1,750,000
- 5 Beds
- 4 Baths
- 4,410 Sq Ft
645 Tyrrel Rd, Millbrook, NY 12545

This historic home was originally built in Millbrook, New York in 1733 by one of the nine partners of the early English land grant. The carefully maintained original architectural features reflect its heritage. On 10 ½ acres the property is a mixture of meadows and woods and bordered on 2 sides by a year round running stream. Clipped lawns surround the house and a privately situated

HEATHER CRONER William Pitt Sothebys Int Rlty

645 Tyrrel Rd, Millbrook, NY 12545
/49
$2,500,000
- 4 Beds
- 4.5 Baths
- 4,960 Sq Ft
163 Hapeman Hill Rd, Red Hook, NY 12571

Nestled in the heart of the Hudson Valley, this striking custom-built compound offers a rare combination of luxury, privacy, and serenity. Set on 3.15 acres of beautifully landscaped grounds, the estate includes a main residence, a legal accessory apartment/guest house, a commercial-sized detached garage, an in-ground heated pool, a pool pavilion, and multiple outdoor living spaces—all

Sean Eidle BHHS Hudson Valley Properties

163 Hapeman Hill Rd, Red Hook, NY 12571
/33
$1,399,999
- 4 Beds
- 3.5 Baths
- 3,674 Sq Ft
36 Spruce Ln, Poughkeepsie, NY 12603

Luxury meets sustainability in this one-of-a-kind custom estate home nestled on 9 serene, wooded acres. Meticulously designed with an eye for elegance and a commitment to energy efficiency, this 4-bedroom, 3.5-bath residence blends sophisticated craftsmanship with modern environmental consciousness.Step inside to find wide-plank white oak flooring, soaring ceilings, and an abundance of

Rich Rundle Greenan Properties RE Agency

36 Spruce Ln, Poughkeepsie, NY 12603
/28
$1,999,999
- 5 Beds
- 2 Baths
- 2,618 Sq Ft
148 Creek Rd, Staatsburg, NY 12580

Welcome to 148 N creek, a stunning property boasting 136 acres of preserved farmland. The sale features a charming 5 bedroom 2 bath farmhouse from the 1800s, several restored and updated barns, . This property is also home to an active farm brewery and agrotourism center. The acreage is protected by the Winnakee Land Conservancy, with future upgrades in mind. Upgraded electric, septic, and well

EUGENE VALOY BHHS Hudson Valley Properties

148 Creek Rd, Staatsburg, NY 12580
/37
$609,000
- 3 Beds
- 2.5 Baths
- 2,688 Sq Ft
53 Leo Ln, Poughquag, NY 12570

Make this 4 Bedroom colonial your home for the summer and beyond! 53 Leo Lane boasts four bedrooms and two and a half bathrooms and plenty of room for entertaining. Situated on over one acre of property which includes an inground pool, a large rear yard, screened in porch and patio space. Enter through the inviting front foyer to access to the family room, living room and spacious dining room.

Melissa Pettinella Century 21 Alliance Realty Grp

53 Leo Ln, Poughquag, NY 12570
/45
$3,750,000
- 5 Beds
- 7 Baths
- 6,050 Sq Ft
33 Pells Rd, Rhinebeck, NY 12572

This magnificent Modern Farmhouse, sheltered in an elegant landscape of rolling hills, mature trees, colorful gardens and a 7-acre lake, is the quintessential Hudson Valley retreat on 43+ picturesque acres. Located an easy five minutes from historic, cultural-rich Rhinebeck Village, it’s the country destination for the sophisticated buyer who values privacy, property and proximity. The striking

Peggy Santamorena Houlihan Lawrence Inc.

33 Pells Rd, Rhinebeck, NY 12572
/34
$72,500
- 1 Bed
- 1 Bath
- 800 Sq Ft
191 Sylvan Lake Rd Unit 16, Hopewell Junction, NY 12533

Price Reduced for Quick sale. Motivated seller offering this cozy, fully furnished 1-bed, 1-bath seasonal cottage (May 1- November 1). Enter into a large and inviting deck and adjoining sunroom with relaxing mountain and wooded views. Continue to the interior of the home which boasts an open concept living room/kitchen with breakfast nook, updated kitchen cabinets and vinyl plank flooring.

RYAN SCHWARZ

191 Sylvan Lake Rd Unit 16, Hopewell Junction, NY 12533
/31
$2,875,000
- 5 Beds
- 6 Baths
- 7,600 Sq Ft
26 Mountain Farm Rd, Millerton, NY 12546

Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring &

Graham Klemm GRAHAM T. KLEMM LIC. RE BROKER

26 Mountain Farm Rd, Millerton, NY 12546
/39
$675,000
- 3 Beds
- 2.5 Baths
- 2,583 Sq Ft
417 Vassar Place, Fishkill, NY 12524

Beautifully maintained, 3 Bedroom, 2.5 Bath, Colonial Condo in the prestigious Toll Bros Van Wyck Glen Community. Country Club-like Maintenance Free Living. First Level entry leads to Sitting Room, Dining room, walk around Kitchen w/Granite Tops, Stainless Steel Appliances, Natural Gas Cooking, Breakfast Area, Large Family Rm w Gas Fireplace, Private Office/Den, Half Bath, Laundry Room w/Washer &

Lisa Walden BHHS Hudson Valley Properties

417 Vassar Place, Fishkill, NY 12524
/50
$2,995,000
- 4 Beds
- 7 Baths
- 6,412 Sq Ft
165 Drake Rd, Pleasant Valley, NY 12569

Welcome to Timber Lake Farm, a stunning property in the heart of Dutchess County horse country. This Adirondack-style estate offers a harmonious blend of rustic elegance and modern luxury, set on 33.26-acre lot with a pristine 9-acre pond that flows over a waterfall at one end. The bespoke stone and wood home boasts 6,412 square feet of living space sited at the highest elevation point on the

Kyle Irwin Corcoran Country Living

165 Drake Rd, Pleasant Valley, NY 12569
/36
$1,600,000
- 5 Beds
- 5.5 Baths
- 5,238 Sq Ft
15 Old Farm Rd, Rhinebeck, NY 12572

Perched on a gentle rise along a private road just ten minutes from Rhinebeck Village, this 5-bedroom custom Craftsman estate—designed by a renowned local architect—seamlessly blends dramatic Art Deco–inspired style with modern comforts. Wide oak floors, premium windows and doors, and brass hardware set the tone, while a suite of advanced systems make the home energy-efficient and off-grid ready.

Zev Eisenberg Hudson Modern Co

15 Old Farm Rd, Rhinebeck, NY 12572
/50
$1,690,000
- 6 Beds
- 2 Baths
- 4,265 Sq Ft
831 Wolcott Ave, Beacon, NY 12508

Elegant Circa 1900 Dutch Colonial Revival in Prime Beacon LocationSituated within walking distance of Beacon’s vibrant Main Street, this distinguished circa 1900 Dutch Colonial Revival residence offers timeless charm and modern luxury. A gracious front entrance, complete with a stately covered porch, welcomes you into this historic brick home, which features six bedrooms and two full

Charlotte Guernsey Compass Greater NY, LLC

831 Wolcott Ave, Beacon, NY 12508
/33
$49,999
- 1 Bed
- 1 Bath
- 750 Sq Ft
50 Glanhope Rd Unit 23, Hopewell Junction, NY 12533

Find your getaway! Located in the beautiful Hudson Valley, this seasonal home with oversized screened porch and large bedroom can easily sleep even the extended family! Additional 150 Sq/Ft deck adds entertaining space. Glanhope Co-Op is a private community of seasonal homes that features a secure gated entry, beautiful inground pool, a great lawn, playground, basketball court, laundry on site

RYAN SCHWARZ

50 Glanhope Rd Unit 23, Hopewell Junction, NY 12533
/33
$12,500,000
- 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

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