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$775,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • Updated 11 days ago
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This Is More Than A Home, It Is A Piece of Long Island History, Offering Space, Character, Low Taxes and An Unbeatable East End Lifestyle. Perfectly Situated On A Picturesque 2 Acre Property. A Hidden Gem Within The Town of Southampton. Offering Exceptionally Low Taxes of Just $5,599. This Rare East End Treasure Combines Timeless Character With Thoughtful Updates. Rich in History and Overflowing With Charm, This 3 Bedroom, 3 Bath Residence Features An Updated Kitchen (2023), New Roof (2022) Rustic Hardwood Floors, Spacious Primary Suite Complete With 2nd Floor Laundry. Welcoming You Into The Home is The All Seasons Room, Complete With New Eze-Breeze Windows. The Full Basement Was Recreated With Impressive 7.5ft Ceilings, Providing Endless Possibilities For Home Gym, Workshop Space or Future Finishing. A Walk Up Attic Showcases The Craftmanship of the Era and Offers Tremendous Potential For Additional Living Space. Modern Conveniences Include 200 Amp Electrical Service, Central Air Conditioning, Separate Hot Water Heater (2023), Inground (6) Zone Sprinkler System. Located In Flanders, A Hamlet within The Town of Southampton, Residents Enjoy Easy Access To The Beaches, Vineyards, Marinas, Farm Stands, Golf Courses, and World Renowned Destinations Of The Hamptons and East Quogue. A More Relaxed Setting at A Remarkable Value. Flanders sits at The Gateway To The South Fork, Boarding The Peconic River & Peconic Bay and Offering Convenient Access To Both Southampton and Riverhead Amenities.

Full Property Details for 38 Pleasure Dr

General

  • Price: $775,000
  • Taxes: $5,599
  • Status: Pending
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 1014808
  • Updated: 7/2/2026
  • Added to Site: 26 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: First Floor Full Bath, Eat-in Kitchen, Entrance Foyer, Formal Dining, Natural Woodwork, Open Floorplan, Open Kitchen, Primary Bathroom, Recessed Lighting, Storage
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Wood Burning
  • Appliances: Dishwasher, Dryer, Electric Cooktop, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater
  • Laundry Facilities: Yes
  • Flooring: Laminate, Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Bathroom

Exterior

  • Porch/Patio/Deck: Covered, Patio, Porch

Parking

  • Parking Features: Driveway, Oversized, Private

Location

  • County: Suffolk County
  • Neighborhood: Flanders
  • Cross Streets: Flanders Road (Route 24)
  • Driving Directions: Sunrise Highway (Route 27), Quogue Riverhead Road to Pleasure Drive, #38 LIE East to Exit 71, Hampton Bays, Edwards Ave S, Routh 24 South to Pleasure Drive, #38

School Information

  • High School District: Riverhead
  • Elementary School: Phillips Avenue School
  • Middle School: Riverhead Middle School
  • High School: Riverhead Senior High School

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Oil
  • Heating Zones: 1

Utilities

  • Sewer: Cesspool
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Trash Collection Private, Water Connected

Structural Information

  • Architectural Style: Colonial
  • Detached/Attached: Detached
  • Construction: Cedar
  • Basement: Yes
  • Basement Desc.: Partially Finished, Walk-Out Access
  • Sq. Ft. Source: Public Records
  • Year Built: 1860

Lot Features

  • Lot Size (Acres): 2.1
  • Lot Size (Sq. Ft.): 91,476
  • Road Maintenance: Public Maintained Road
  • Fence: Yes
  • Lot Features: Back Yard, Front Yard, Garden, Landscaped, Level, Near Golf Course, Part Wooded, Private, Sprinklers In Front, Sprinklers In Rear
  • Fencing (Description): None

Financial Considerations

  • Tax Amount: $5,599

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 0900-168-00-01-00-012-000
  • Block: 100
  • Lot Number: 12

Listed by Signature Premier Properties

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Listing agent

— 38 Pleasure Dr —

  • Signature Premier Properties

631-368-6800

Get Pre-Approved Today

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with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 38 Pleasure Dr

School District:Riverhead Central School District
NameGradesDistance
Phillips Avenue School
141 Phillips Avenue, Riverhead, NY 11901
K-41.9 mi
Riverhead Middle School
600 Harrison Avenue, Riverhead, NY 11901
7-83.4 mi
Riverhead Senior High School
700 Harrison Avenue, Riverhead, NY 11901
9-123.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 38 Pleasure Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/17/2026
Listed
$775,000
76.94%
MLS
7/31/2020
Sold
$438,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 38 Pleasure Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,236
3%
$307,000
—
2020
$5,083
-2%
$307,400
—
2016
$5,174
2%
$307,400
—
2020
$5,053
-2%
$307,400
4%
2018
$5,155
1%
$294,600
3%
2017
$5,112
-1%
$286,300
—
2016
$5,186
1%
$286,300
—
2015
$5,152
-2%
$286,300
—
2015
$5,246
-2%
$286,300
—
2014
$5,330
7%
$286,300
—
2013
$4,985
—
$286,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 38 Pleasure Dr

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Down Payment
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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Signature Premier Properties

38 Pleasure Drive, Flanders, NY 11901 (MLS# 1014808) is a Single Family property with 3 bedrooms and 3 full bathrooms. 38 Pleasure Drive is currently listed for $775,000 and was received on June 17, 2026. Want to learn more about 38 Pleasure Drive? Do you have questions about finding other Single Family real estate for sale in Flanders? You can browse all Flanders real estate or contact a Coldwell Banker agent to request more information.

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