Welcome to 366 Overlook Road in Pleasant Valley—an exceptional raised ranch offering refined updates, thoughtful design, and outstanding flexibility. This spacious 5-bedroom, 3.5-bath home features two full kitchens with stainless steel appliances, ideal for versatile living arrangements, extended household needs, or guest accommodations. Additional highlights include a cozy fireplace, dedicated laundry room, and a 2-car garage, all set within a well-designed layout that balances comfort and functionality.
Ideally located near Route 44, the Taconic State Parkway, and Metro-North access in nearby Poughkeepsie for an easy commute. Enjoy proximity to shopping, dining, and everyday conveniences, as well as outdoor destinations such as James Baird State Park, Walkway Over the Hudson, and local trails and parks. A move-in-ready opportunity in a desirable Dutchess County location offering space, flexibility, and lifestyle appeal.
Sold for $635,000
$635,000
366 Overlook Road, Pleasant Valley, NY 12569
4beds
2,668sqft
Single Family Residence, Residential
Built in 1975
0.69 Acres Lot
$638,000 Zestimate®
$238/sqft
$4,650 Estimated rent
Home value
$638,000
$587,000 - $695,000
$4,650/mo
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$4,240/mo
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Zillow last checked: 7 hours ago
Listing updated: March 31, 2026 at 11:46am
Listed by:
Joseph Lukic 914-334-3805,
Compass Greater NY, LLC 914-752-8763,
Geno M. George 917-374-2591,
Compass Greater NY, LLC
Bought with:
Liudmila Lobeeva, 10401375127
eXp Realty
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 948268
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Baseboard, Oil
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
- Laundry: In Basement
Features
- First Floor Bedroom, First Floor Full Bath, Chandelier, Crown Molding, Eat-in Kitchen, Entrance Foyer, In-Law Floorplan, Open Floorplan, Open Kitchen, Primary Bathroom
- Flooring: Tile, Wood
- Basement: Finished,Full,See Remarks,Walk-Out Access
- Attic: Pull Stairs
- Number of fireplaces: 1
- Fireplace features: Family Room
Interior area
- Total structure area: 2,668
- Total interior livable area: 2,668 sqft
Property
Parking
- Total spaces: 6
- Parking features: Attached, Driveway, Garage, Garage Door Opener
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Two
- Patio & porch: Covered, Deck, Patio
Lot
- Size: 0.69 Acres
- Features: Back Yard, Front Yard
Details
- Parcel number: 1334006461010108720000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence, Residential
Materials
- Vinyl Siding, Wood Siding
- Foundation: Concrete Perimeter
Condition
- Year built: 1975
Utilities & green energy
- Sewer: Septic Tank
- Water: Private
- Utilities for property: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Trash Collection Public, Water Connected
Community & neighborhood
Location
- Region: Pleasant Valley
Other
Other facts
- Listing agreement: Exclusive Right To Sell
Price history
| Date | Event | Price |
|---|---|---|
| 3/31/2026 | Sold | $635,000+1.6%$238/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #948268 Report a problem | ||
| 2/11/2026 | Pending sale | $625,000$234/sqft |
Source: OneKey® MLS as distributed by MLS GRID #948268 Report a problem | ||
| 1/7/2026 | Listed for sale | $625,000+290.9%$234/sqft |
Source: OneKey® MLS as distributed by MLS GRID #948268 Report a problem | ||
| 9/30/1993 | Sold | $159,900$60/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $296,600 |
| 2023 | -- | $296,600 |
| 2022 | -- | $296,600 |
| 2021 | -- | $296,600 |
| 2020 | -- | $296,600 |
| 2019 | -- | $296,600 +4% |
| 2018 | -- | $285,200 |
| 2017 | $7,821 | $285,200 |
| 2016 | -- | $285,200 |
| 2015 | -- | $285,200 |
| 2014 | -- | $285,200 -6% |
| 2012 | -- | $303,300 -6.7% |
| 2011 | -- | $325,000 |
| 2010 | -- | $325,000 -10% |
| 2009 | -- | $361,000 -7.9% |
| 2008 | -- | $392,000 -8.9% |
| 2007 | -- | $430,500 +123.1% |
| 2006 | -- | $193,000 |
| 2005 | -- | $193,000 |
| 2004 | -- | $193,000 |
| 2003 | -- | $193,000 |
| 2002 | -- | $193,000 |
| 2001 | -- | $193,000 |
| 2000 | -- | $193,000 |
Find assessor info on the county website
Neighborhood: 12569
Nearby schools
GreatSchools rating
- NAOverlook Primary SchoolGrades: K-2Distance: 2.1 mi
- 4/10Lagrange Middle SchoolGrades: 6-8Distance: 2.9 mi
- 6/10Arlington High SchoolGrades: 9-12Distance: 2 mi
Schools provided by the listing agent
- Elementary: Overlook Primary School
- Middle: Lagrange Middle School
- High: Arlington High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$638,000
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$638,000
- New York
- Dutchess County
- Pleasant Valley
- 12569
- 366 Overlook Road