This home's estimate is 12.4% higher than the average sale price ($567K) of 6 comparable homes.
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366 Overlook Rd, Pleasant Valley, NY 12569
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About this home
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.
Redfin Estimate
Market trends in 12569, NY
Last updated August 2026
Buyer's Market
Seller's Market
Balanced market
- $650,0003 beds2.5 baths2,232 sq ft2800 Route 82, Pleasant Valley, NY 12569Listing by Houlihan Lawrence Inc.
- $449,9003 beds1.5 baths1,640 sq ft1078 Salt Point Tpke, Pleasant Valley, NY 12569Listing by Century 21 Alliance Rlty Group
- COMING SOON
- $649,0003 beds2.5 baths2,264 sq ft71 O'halloran Cir, Pleasant Valley, NY 12569Listing by BERKSHIRE HATHAWAY
- $615,0004 beds2.5 baths1,804 sq ft13-17 Clark Hts, Pleasant Valley, NY 12569Listing by BHHS Hudson Valley Properties
- $339,0002 beds1.5 baths1,766 sq ft33 North Ave, Pleasant Valley, NY 12569Listing by George T Whalen Real Estate
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Est. $3,848 per month, based on comparable rentals
Redfin agents who toured
- Beautifully renovated home.8 months ago• May not reflect the current state of the homeRedfin Premier agent
Sale and tax history for 366 Overlook Rd
- Sale History
- Tax History
$238/sq ft
$234/sq ft
$234/sq ft
$60/sq ft
Public record
Property details
Parking
- Parking Information
- Carport YN: No
- Parking Total: 6
- Parking Features: Attached, Driveway, Garage, Garage Door Opener
- Garage Information
- Garage Spaces: 2
- Has Garage
Interior
- Fireplace Information
- Has Fireplace
- Fireplaces Total: 1
- Fireplace Features: Family Room
- Heating & Cooling
- Cooling: None
- Heating: Baseboard, Oil
- Interior Features
- Interior 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
- Laundry Features: In Basement
- Appliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
- Flooring: Tile, Wood
- Levels: Two
- Patio And Porch Features: Covered, Deck, Patio
- Room Information
- Basement YN: Yes
- Attic: Pull Stairs
- Rooms Total: 10
- Basement: Finished, Full, See Remarks, Walk-Out Access
- Bathroom Information
- Bathrooms Full: 3
Exterior
- Exterior Features
- Construction Materials: Vinyl Siding, Wood Siding
- Foundation Details: Concrete Perimeter
- Waterfront YN: No
- Lot Information
- Lot Features: Back Yard, Front Yard
- Property Information
- Living Area Source: Public Records
- Living Area (Sq. Ft.): 2668.00
- Property Sub Type: Single Family Residence
Financial
- Tax Information
- Tax Year: 2025
- Tax Source: Municipality
- Tax Annual Amount: $15,386
- Financial Information
- Buyer Financing: Conventional
Utilities
- Utility Information
- Electric Company: Central Hudson
- Sewer: Septic Tank
- Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Trash Collection Public, Water Connected
Location
- School Information
- Elementary School: Overlook Primary School
- Elementary School District: Arlington
- Middle Or Junior School: Lagrange Middle School
- Middle Or Junior School District: Arlington
- High School: Arlington High School
- High School District: Arlington
- Location Information
- County Or Parish: Dutchess County
Public facts
- Beds: 5
- Baths: 3.5
- Sq. Ft.: 2,668
- Stories: 1.0
- Lot Size: 0.69 acres
- Style: Single Family Residential
- Year Built: 1975
- Year Renovated: 1980
- County: Dutchess County
- APN: 133400A00646100010108720000
Around this home
Schools
Public K-2 • Assigned • 2.0mi
Public 6-8 • Assigned • 2.9mi
Public 9-12 • Assigned • 2.0mi
Climate risks
Minimal risk of a flood reaching the building in the next 30 years
0.15% chance of being in a wildfire in next 30 years
7 days above 98° expected this year, 15 days in 30 years
13% chance of strong winds in next 30 years
2 unhealthy days expected this year, 3 days in 30 years
Sun exposure
In this area, properties receive around 8.7 hours in June and 3.9 hours in December, placing it below the U.S. average for solar exposure.
Nearby similar homes
New listings for sale in 12569
Home values near 366 Overlook Rd
| Address | Redfin Estimate |
|---|---|
3 Beds | 1 Baths | 1082 Sq. Ft. | $417,131 |
3 Beds | 1 Baths | 2097 Sq. Ft. | $429,929 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 2 Baths | 1248 Sq. Ft. | $558,032 |
3 Beds | 1.5 Baths | 2896 Sq. Ft. | $494,537 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 1.5 Baths | 1544 Sq. Ft. | $432,523 |
3 Beds | 1.5 Baths | 1684 Sq. Ft. | $397,350 |
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