Dutchess Homes with Pool Amenities

Welcome to Dutchess County, New York, a picturesque region that beautifully blends the charm of small-town living with the vibrancy of urban amenities. Nestled in the heart of the Hudson Valley, Dutchess County is renowned for its stunning landscapes, rich history, and an array of outdoor recreational activities. With the majestic Hudson River winding through it and the scenic foothills of the Catskills as a backdrop, this county is a haven for nature lovers and adventure seekers alike.

In Dutchess County, you’ll find a diverse real estate market that caters to every lifestyle, including homes with luxurious pool amenities. Imagine stepping into your backyard oasis on a warm summer day, where a sparkling pool awaits you, surrounded by lush gardens and serene landscapes. These homes not only provide a perfect space for relaxation and entertainment but also offer a lifestyle that embraces the beauty of outdoor living.

Whether you’re hosting a summer barbecue, enjoying a quiet evening under the stars, or simply taking a refreshing dip, having a pool at home elevates your living experience. Many properties in Dutchess County feature expansive decks, outdoor kitchens, and beautifully landscaped yards, making them ideal for family gatherings or peaceful retreats.

Dutchess County is also home to a vibrant community, with charming towns like Rhinebeck and Beacon offering unique shops, delightful restaurants, and cultural attractions. With excellent schools and a strong sense of community, it’s no wonder families are drawn to this enchanting region. Explore the possibilities of finding your dream home with pool amenities in Dutchess County, where every day feels like a vacation!

Newest Dutchess Homes with Pool Amenities

$499,000

1 Beds ⋅ 2 Baths ⋅ 1047253 MLS

Beautifully maintained unit on second floor in a premier 55+ community at The Regency in Fishkill. Primary bedroom with walk in closet, den for office, media room or the perfect guest room with a full bath right outside the door. Balcony, open floor plan, laundry, water view, Recently professionally cleaned recently, ready to move in and enjoy! Amenities include heated pool, grilling area active clubhouse with full kitchen and meeting room, manicured grounds. Easy access to shopping, medical facilities, hotels, Fishkill and Beacon Main St attractions, Route 9, 52, Taconic State Parkway and I-84. If you are looking for a low maintenance lifestyle, convenience and great amenities this is it!

621 Regency Drive, Fishkill

$499,000

2 Beds ⋅ 3 Baths ⋅ 1050080 MLS

You will fall in love with this unique and impeccably maintained, end unit townhouse with 3 finished floors! The kitchen was custom designed, which includes breakfast bar that opens up to dining area, stainless appliances and quartz counter tops. Sliding glass doors from your dining area leads to your oversized, 10X25, deck with retractable awning. The center of attraction is your gorgeous limestone, 18-foot fireplace wall with custom walnut slab mantel in your living room with expansive Palladian window to keep this unit light and bright. Your main floor also has your office/den/library, a full bath and laundry room. Your upstairs offers the inviting primary bedroom suite that includes full updated bath with heated flooring and over-sized closets plus additional bedroom and generous sized loft which had the windows replaced. But that's not all! Your lowest level offers a generous sized gathering room for all occasions with gas stove and walk out to your blue stone patio. Central air, landscaped yard, maximized use of available outdoor space with deck and patio, walk to community pool and clubhouse, new roof in 2014, One car garage with new garage door system with battery back up and wifi capability (2018) plus generator hookup. Deer Crossing is a community of 50 units near all commuter routes, shopping and medical services. Pride of ownership shows with all that this beautiful townhouse has to offer. You truly will not be disappointed viewing this overly spacious gem if you are in the market for a townhouse.

50 Deer Crossing Drive, Fishkill

$396,000

2 Beds ⋅ 2 Baths ⋅ 1046364 MLS

Natural light, room to live, and convenience at every turn. This 2-bedroom end-unit townhouse in Elmcrest offers 1,563 square feet of flexible living space. The bright two-story entry opens to a living room with hardwood floors, a gas fireplace, and direct access to the back deck. A first-floor half bath adds convenience. The home was refreshed and upgraded in December 2025 with fresh paint throughout, newly painted kitchen cabinets, a new fireplace insert, and a refreshed full bath with new fixtures. The kitchen also features granite countertops, LG stainless-steel appliances purchased in 2025, and a large pantry. Upstairs, the primary bedroom includes a walk-in closet, while the full bath offers a large linen closet. Downstairs, the finished basement adds two flexible rooms for a home office, gym, media room, hobby space, or extra storage. A one-car attached garage, two-car driveway, and nearby guest parking make daily life easier. Elmcrest’s community pool gives you a place to cool off and unwind, while the HOA handles lawn care, snow removal, trash, and pool access. With shopping, restaurants, train access, and transportation routes nearby, errands and commuting are easier, leaving more time to enjoy the space you come home to.

246 Crestwood Court, Fishkill

$484,900

2 Beds ⋅ 3 Baths ⋅ 1049793 MLS

Welcome to this beautiful end-unit townhome in the sought-after Holly Ridge community of Fishkill! Built in 2005, this inviting 2-bedroom, 2.5-bath home offers an abundance of natural light, thoughtful living spaces, and the privacy of a beautifully landscaped, tree-lined backyard. Step inside through the open foyer and discover a home designed for comfortable everyday living. The spacious primary bedroom features a private en suite bath, while large closets throughout provide plenty of storage. A full, unfinished basement offers even more storage space and the opportunity to create additional living areas to suit your needs. The attached 2-car garage and double driveway accommodate up to four vehicles, making parking and entertaining a breeze. Outside, enjoy the peaceful backyard setting, where mature trees and beautiful landscaping create a private retreat. Holly Ridge offers an exceptional array of amenities for an active and enjoyable lifestyle, including a clubhouse with an inground pool, kiddie pool, gym with changing areas and restrooms, and a kitchen. Tennis, basketball, and pickleball courts provide plenty of opportunities for recreation and fun. Recent updates include a new roof in 2025 and a central air conditioning unit replaced in 2015. Conveniently located near major roads, Metro-North, the City of Beacon, and the Village of Fishkill, this home offers easy access to shopping, dining, commuting, and all that the Hudson Valley has to offer. Come discover the comfort, privacy, and wonderful community amenities that make Holly Ridge Townhomes such a special place to call home!

1402 Pondview Loop, Wappingers Falls

$199,999

2 Beds ⋅ 2 Baths ⋅ 1047305 MLS

Welcome to 3 Hook Road, Unit 72A, a charming 2-bedroom, 1.5-bath condo at The Arbor Condominiums, offering comfortable living, thoughtful updates, and a convenient Poughkeepsie location in Hyde Park School District. Step inside and feel right at home in the inviting living space, where everyday living feels easy and relaxed. The tastefully designed kitchen features stainless steel appliances and a welcoming layout that makes preparing meals and entertaining a pleasure. Just off the main living area, walk-out access leads to your private patio and the beautifully shared backyard- an ideal spot for morning coffee, an evening unwind, or enjoying a little fresh air. The pet-friendly community makes it easy for your four-legged friends to feel at home, too! Residents of The Arbor enjoy wonderful community amenities, including a refreshing communal pool and playground, perfect for enjoying those warm summer days. One assigned parking space is included, with plentiful visitor parking available for guests. And when it’s time to head out, you’ll love the convenience of being just 2.9 miles-approximately 9 minutes-from the train station, with shopping, dining, entertainment, and everyday conveniences along Route 9 all close by. This inviting condo offers a wonderful combination of comfort, community, and convenience. Come see all that 3 Hook Road #72A has to offer and imagine yourself calling The Arbor Condominiums home!

3 Hook Road Unit #72A, Poughkeepsie

$325,000

1 Beds ⋅ 1 Baths ⋅ 1048326 MLS

Welcome home to stunning Hudson River views. Experience nature's magic through all the seasons with an exclusive front row seat to the majestic Hudson River. Whether it's the vibrant autumn leaves, crackling ice, return of leisure boats in the spring or festive summer fireworks, the exceptional tidal views are ever changing and always spectacular. The home is perfectly positioned between the iconic Mid-Hudson Bridge and Shadows Marina. Inside you'll appreciate thoughtful touches throughout with custom built-ins, extra wide molding, pocket French doors and designer lighting. The beautifully designed kitchen boasts Thomasville cabinetry, an abundance of counter space and stainless-steel appliances. The walk-in, custom closet comes complete with all the bells and whistles and the convenience of in-unit laundry is discreetly hidden behind cabinetry. Enjoy the newly renovated community pool, grill stations and exceptional walkability just steps away from Shadows on the Hudson and the train station. HOA fee includes real estate taxes, water, sewer, exterior building maintenance, snow removal, landscaping, pool, garbage removal, insurance and exterior lighting.

38 Hurlihe Street Unit #38B, Poughkeepsie

$349,000

3 Beds ⋅ 2 Baths ⋅ 1032826 MLS

Welcome to easy living in the desirable Roundtree community! This inviting end-unit townhouse offers three bedrooms, one-and-a-half baths, and the added privacy and natural light of an end location. Enjoy a two-car driveway, convenient guest parking directly across the way, and close proximity to the community pool. The low HOA fee includes snow removal, grounds maintenance, and pool access, allowing for a more carefree lifestyle. Ideally located near shopping, restaurants, Fishkill Ridge trails, and just nine minutes from the Beacon train station—perfect for commuters and anyone looking to enjoy everything the Hudson Valley has to offer!

31 Roundtree Court, Beacon

$829,900

2 Beds ⋅ 3 Baths ⋅ 1036134 MLS

Welcome to The Regency at Wappinger!! Discover your dream lifestyle in this stunning detached home, perfectly situated within a highly sought-after 55+ active adult community. This beautifully appointed residence features 2 spacious bedrooms, a versatile den, a formal dining room, and an inviting great room with sliding glass doors that open to a private deck with a staircase to the lower level. Entertain or unwind in the impressive full, finished walk-out basement! Beyond your front door, enjoy resort-style living with unparalleled amenities, including a vibrant clubhouse, swimming pool, pickleball courts, tennis courts, bocce courts, a fitness center, and a variety of social clubs. Your next chapter begins here! This home features an entrance foyer with very high ceilings which opens up to the formal dining room and well-equipped kitchen with pantry. The very spacious great room features magnificent mountain views from the deck. The primary bedroom includes a large walk-in closet and a private primary bath with a dual-sink vanity, a Roman tub, a separate shower with a seat, and a private toilet area. Additional highlights include a convenient first-floor laundry room, a two-car garage, and plenty of extra parking in the driveway. Plus, you'll love the commuter-friendly location with easy access to shopping, highways, and the Hudson train line.

5 Palmerton Drive, Wappingers Falls

$597,500

3 Beds ⋅ 3 Baths ⋅ 1047471 MLS

Welcome Home! You will fall in love with this beautiful, well-maintained Colonial! Relax on the covered front porch, which overlooks lovely park-like property, numerous perennial gardens, mature trees. Special features of this wonderful home are central air, a hard to find 1st floor Primary Suite with an updated full bath and walk-in closet. Off the large foyer is a spacious, warm & inviting Living Rm with hardwood, which is open to an equally inviting Dining Rm, also with hardwood. Fantastic Kitchen has beautiful, ceiling-height cabinets, granite counters, hardwood floor, tons of storage. Great for entertaining, the Kitchen is open to a large, sunny Family Rm, which has a fireplace, hardwood and sliders to a Deck with retractable awning. From the Deck you will enjoy a scenic pond view and the large, level back yard. The first floor offers crown molding, hardwood and an elegant half-bath. Upstairs you will discover a large, beautiful full bath with dual sink vanity & laundry area, two great Bedrooms, plus a Den or Guest Rm with hardwood. This home has been very-well maintained, the driveway is freshly sealed. Large unfinished basement has endless uses! Deerfield Ponds offers the community an inground Pool, Tennis, Basketball court and Clubhouse with Fitness Rm. Right down the road from Deerfield Ponds is Dykeman Farm, known for their delicious corn, tomatoes, more. Pawling is a lovely town which offers a large array of businesses on Route 22 and the picturesque Village, where you will find Metro-North Train Station (Harlem Line), wonderful Restaurants, Pubs, Bakeries, Shops, Clothing Boutique, Book & Antique store, Library, Museums... Dutcher Golf Course is the oldest public course in America! we also have Lakeside Park with sand beach & playground, Daryl's House Music Club & Restaurant, Gyms, so much more! Pawling has something for everyone!

41 W Deer Trail, Pawling

$452,000

2 Beds ⋅ 3 Baths ⋅ 1047529 MLS

Welcome home to 6 N Cambridge Court located in the highly desirable Fox Ridge community. This is a lovely multi-level townhouse that radiates true pride of ownership. Spanning a spacious 1,572 square feet, this beautifully maintained 2-bedroom, 2.5-bathroom residence has been comprehensively updated for modern, worry-free living. Step inside to discover a bright and inviting interior featuring fresh paint and premium new flooring throughout the entire home. The main level boasts a fully updated kitchen that flows seamlessly into the open dining and living areas, which are anchored by a cozy woodburning fireplace. There is also a beautifully remodeled first-floor bathroom and a brand-new washer and dryer set. No detail has been overlooked: brand-new windows and doors elevate both the home’s energy efficiency and its curb appeal, while professional landscape improvements create an enchanting outdoor welcome. Complete with central air and an attached garage, this immaculate property offers a rare combination of stylish updates and an exceptional location. Fox Ridge offers a relaxing, maintenance-free lifestyle. The HOA provides complete snow removal—including driveways, pathways, and front porches—along with exterior maintenance, allowing you to enjoy the community's pool and tennis courts without the hassle of seasonal upkeep. Ideally located just minutes from shopping, restaurants, Metro-North, I-84, and all that the charming Village of Fishkill has to offer, this move-in-ready home provides both comfort and convenience.

6 N Cambridge Court, Fishkill

$220,000

3 Beds ⋅ 2 Baths ⋅ 1047515 MLS

Welcome to Tally Ho, a desirable 55+ community in Dover Plains, where comfortable living meets convenience. This well-maintained 2021 28'x52' manufactured home offers a 1456 sq. ft. of spacious and inviting floor plan with plenty of room to relax and entertain. The large living room provides a welcoming gathering space, while the generously sized eat-in kitchen features stainless steel appliances, abundant cabinetry, and excellent storage. The kitchen is both functional and comfortable, with plenty of room for dining and everyday living. The spacious primary bedroom offers a full en-suite bathroom and a large walk-in closet, creating a comfortable private retreat. A shed is also included, providing additional storage for tools, outdoor equipment, and more. Enjoy the amenities Tally Ho has to offer, including a clubhouse, in-ground pool, bocce, and a variety of community activities. The lot rent includes taxes, adding to the convenience of ownership. Ideally located just minutes from the Metro-North train station, Harlem Valley Rail Trail, shopping, restaurants, and other local amenities. This move-in-ready home offers low-maintenance living in a welcoming 55+ community in the beautiful Harlem Valley.

60 Celeste Drive, Dover Plains

$579,000

3 Beds ⋅ 3 Baths ⋅ 1045711 MLS

Welcome to 1307 Glastonbury Lane, an exceptional end-unit Carlyle model in the highly desirable Enclave at Toll Brothers Van Wyck Meadows, offering an ideal blend of space, natural light, privacy, and effortless modern living. Ideally positioned on a corner, this coveted location features additional windows throughout, creating a bright, open atmosphere where you may almost forget you are living in a townhouse. A welcoming entry opens to an expansive, thoughtfully designed interior with soaring ceilings, beautiful hardwood floors, and an inviting layout. The formal dining room is accented by a tray ceiling, crown moldings, and an elegant bay window, while a dedicated first-floor office provides the perfect space for working from home. The elegant kitchen showcases rich cherry cabinetry, granite countertops, stainless steel appliances, and an inviting breakfast bar, flowing seamlessly into the family room with a charming bay window and gas fireplace. Upstairs, the primary suite offers a peaceful retreat with a dramatic cathedral ceiling, sitting area, generous walk-in closet, and well-appointed en-suite bath. A versatile bonus space just off the primary bedroom provides endless possibilities for a sitting room, nursery, private office or exercise area. Two additional bedrooms, each with new hardwood flooring, offer comfortable accommodations for family and guests. The expansive walk-out lower level adds another dimension of possibilities, with nearly 900 square feet of unfinished space, high ceilings, and rough plumbing, ready to be transformed into a media room, recreation area, home gym, or a combination of spaces tailored to your needs. Outside, the spacious composite deck, freshly stained in 2023, provides a wonderful setting to relax and enjoy the peaceful surroundings. Meticulously maintained and thoughtfully updated, the home features fresh interior paint from 2021, select areas refreshed in 2026, modern light fixtures, new hardwood flooring in all bedrooms, water heater and water softener in 2025, and an updated HVAC condenser unit. Residents enjoy an exceptional lifestyle with resort-style amenities including a pool, clubhouse, fitness center, tennis, pickleball, basketball courts, and underground utilities. Beyond the community, an abundance of shopping, dining, recreation, and entertainment is just minutes away, including Bowdoin Park, James Baird Golf Course, and the historic village center of Fishkill. Zoned for the highly regarded Wappingers Falls School District, with easy access to Route 9, I-84, the Taconic State Parkway, and New Hamburg Metro-North. Offering the scale and versatility of a single-family home with the convenience and lifestyle of luxury townhouse living, 1307 Glastonbury is a rare opportunity to experience one of Van Wyck Meadows' most desirable end-unit locations.

1307 Glastonbury Lane, Fishkill

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