Pleasant Valley NY real estate sits at something of an unofficial crossroads. The 200-year-old town of Pleasant Valley is mid-way between highly-developed Poughkeepsie to its west and the thickly forested lands to its east that stretch well into Connecticut. Its residential enclaves, a combination of suburban developments from the last half-century and old farmhouses from the town's beginnings, are cushioned by woodsy areas; only the very center of the hamlet of Pleasant Valley, directly on Route 44, shows little green on the map.
Pleasant Valley offers some wonderful real estate. As the local experts in Hudson Valley real estate we'd love show you the town.
Pleasant Valley Properties For Sale
| All Listings |
Under $100,000 |
$100,000 - $200,000 |
| $200,000 - $300,000 |
$300,000 - $400,000 |
$400,000 - $500,000 |
| $500,000 - $600,000 |
$600,000 - $700,000 |
$700,000 - $800,000 |
| $800,000 - $900,000 |
$900,000 - $1,000,000 |
Over $1,000,000 |
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Commercial Sale
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0 Beds
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0 Baths
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14,350
SqFt
$4,000,000
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Commercial Sale
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0 Beds
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0 Baths
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11,093
SqFt
$1,800,000
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Residential
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5 Beds
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4 Baths
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5,370
SqFt
$1,300,000
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Residential
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4 Beds
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3.5 Baths
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3,888
SqFt
$1,295,000
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Residential
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4 Beds
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5 Baths
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6,085
SqFt
$1,250,000
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Residential
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4 Beds
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5 Baths
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5,200
SqFt
$1,125,000
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Residential
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3 Beds
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3 Baths
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2,470
SqFt
$998,000
↓ $52,000
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Commercial Sale
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0 Beds
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0 Baths
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6,478
SqFt
$995,000
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Residential
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3 Beds
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3 Baths
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3,770
SqFt
$900,000
Sale Pending
![166 Creek Road, Pleasant Valley]()
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Residential
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3 Beds
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4 Baths
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4,059
SqFt
$725,000
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Residential
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3 Beds
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3 Baths
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2,678
SqFt
$600,000
↓ $15,000
New
![65 O'halloran Circle, Pleasant Valley]()
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Residential
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3 Beds
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2 Baths
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1,500
SqFt
$599,000
Time to relax after house-hunting: Cottonwood Inn is rural & close to restaurants. Golden Manor Motel is handy to the Roosevelt & Vanderbilt sites. Wing’s Castle views are stupendous! See our list...
The original cinder bed of the Poughkeepsie & Eastern Railroad comprises the trail at Bower Park. Meadow Creek Farm Equestrian Center offers lessons, sales, leasing & boarding. See our list...
Check out programs & exhibitions of The Art Effect & Millbrook Arts Group or classes, workshops & performances of Cocoon Theater. See movies at the drive-ins or Roosevelt Cinema. See our list...
Go for group treks or farm tours at Lilymoore Alpaca Farm. Clover Brooke Farm has alpacas but also Pygoras goats, sheep & barn cats. Netherwood Acres has been going since 1950. See our list...
Mama’s Baked Apple Pancakes at the Village Restaurant. Broccoli Garlic Soup & The Bella salad at Madison’s. Vegetable Tempura at Tokyo Tavern. Soupe du Jour at Café les Baux. See our list...
At Styles by Maureen you’re with a life-long Pleasant Valley-ite. Download a $20 gift towards new services at Marion Salon Spa. Plan a birthday party with Cherilyn’s School of Dance. See our list...
Among other great things, Hummingbird Ranch makes Hive Mix, a blend of raw wildflower honey, propolis, pollen & royal jelly. Browse vintage to contempo at Past ‘n’ Perfect. See our list...
One of the remnants of Pleasant Valley’s past is the lovely Mill Site & Memorial Park. You’re invited to explore the woods & trails & fish the lakes & streams of Bilmar Nursery. See our list...
There's so much to do in Pleasant Valley, NY - it can be hard to decide! Contact one of our Local Experts at . We’d love to give you our recommendation on the best things to do in Pleasant Valley.
What is now known as Route 44 follows what was once a Native American trail along the Wappingers Creek. In the early 1700s it was called Filkintown Road, because of Isaac Filkins’ grist mill, and some folks from Connecticut built a church there in 1747 and established a burial grounds, where you can visit the old graves in their idyllic setting to this day.
Over the years some important early structures have disappeared from the town. People who live here support keeping historic buildings intact and seeing that new buildings fit in with the character of the hamlets. A few Pleasant Valley buildings are listed on the National Register of Historic Places: the 1760s Georgian/Dutch-style Newcomb-Brown Estate and the buildings in the Bloomvale Historic District. Other historic buildings include the Smith Road barn, Peter Flagler House and the Firemen’s Hall.
Pleasant Valley has some very nice parks with Bower Park, the Taconic Hereford Multiple Use Area, James Baird State Park, Helen Aldrich Park and Cady Field (behind town hall) amongst them. Just over the town border in Millbrook is the renowned Innisfree Garden.
Everyone is welcome to revel in the town's annual celebrations. Pleasant Valley Weekend is one, with parades and parade-watchers, fireworks, games and rides… and the Little Miss Pleasant Valley pageant! Partying with neighbors, taking care of one another, doing things together is what matters. At the Pleasant Valley/LaGrange Senior Drop-In Center at Town Hall, the town’s older citizens meet new friends, socialize, enjoy meals and stay active. At the library, aside from the usual reading groups and story-time, you may find workshops like; “Reducing Plastic in Our Lives and Our Environment,” “Remember the Ladies: Finding Your Maternal Ancestors” and “Haunted Objects.”
One Pleasant Valley business keeping local ties strong is the family-owned Hudson Valley Cold-Pressed Oils. All materials used in the production of their oil are either grown on site or within 30 miles, and they’re conscientiously creating an ecological circle whereby all byproducts of production are used for something else, such as gluten-free flour, baking mixes and skin-care products.
There are opportunities to acquire a home for sale in Pleasant Valley in almost any style you can imagine, from a 1935 Cape Cod to a 1974 split-level with pool to a 2021 contempo with Catskills views. Perhaps you'll fall in love with the fine, old wide-board floors an or a waterfall.
Get in touch with a agent who will help you explore the terrain and real estate of Pleasant Valley, NY.
For more information about Pleasant Valley real estate in New York, feel free to We'd love help you find your dream home!
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INFORMATION COPYRIGHT 2022, ONEKEY™ MLS. ALL RIGHTS RESERVED. THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. THIS INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS’ PERSONAL, NON-COMMERCIAL USE. THE DATA RELATING TO REAL ESTATE FOR SALE ON THIS WEBSITE COMES IN PART FROM THE IDX PROGRAM OF ONEKEY® MLS
Listing information last updated on March 22nd, 2025 at 11:45am EDT.
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THE DATA RELATING TO REAL ESTATE ON THIS WEBSITE COMES IN PART FROM THE IDX OF THE MULTIPLE LISTING SERVICE OF ULSTER COUNTY, INC. REAL ESTATE LISTINGS HELD BY BROKERAGE FIRMS OTHER THAN Coldwell Banker Village Green Realty ARE MARKED WITH IDX LOGO AND THE DETAILED INFORMATION ABOUT THEM INCLUDES THE NAME OF THE LISTING BROKER.
COPYRIGHT © 2025 BY THE MULTIPLE LISTING SERVICE OF ULSTER COUNTY, INC. ALL RIGHTS RESERVED.
ALL INFORMATION PROVIDED IS DEEMED RELIABLE BUT IS NOT GUARANTEED AND SHOULD BE INDEPENDENTLY VERIFIED.
IDX INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS' PERSONAL, NON-COMMERCIAL USE AND MAY NOT BE USED FOR ANY PURPOSE OTHER THAN TO IDENTIFY PROSPECTIVE PROPERTIES CONSUMERS MAY BE INTERESTED IN PURCHASING.
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IDX INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS' PERSONAL, NON-COMMERCIAL USE AND MAY NOT BE USED FOR ANY PURPOSE OTHER THAN TO IDENTIFY PROSPECTIVE PROPERTIES CONSUMERS MAY BE INTERESTED IN PURCHASING.
IDX INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS' PERSONAL, NON-COMMERCIAL USE AND MAY NOT BE USED FOR ANY PURPOSE OTHER THAN TO IDENTIFY PROSPECTIVE PROPERTIES CONSUMERS MAY BE INTERESTED IN PURCHASING.