Pending
Price CutPrice Drop: $110K (09/30)
Sale Pending at 90 Caiola Ct, Southold, NY 11944 | MLS# 1027434 | Listing updated on 2026-09-30
Photo 1 of Sale Pending at 90 Caiola Ct, Southold, NY 11944 | MLS# 1027434 | Listing updated on 2026-09-30
Photo 2 of Sale Pending at 90 Caiola Ct, Southold, NY 11944 | MLS# 1027434 | Listing updated on 2026-09-30
Photo 3 of Sale Pending at 90 Caiola Ct, Southold, NY 11944 | MLS# 1027434 | Listing updated on 2026-09-30
Photo 4 of Sale Pending at 90 Caiola Ct, Southold, NY 11944 | MLS# 1027434 | Listing updated on 2026-09-30
34+
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Street View

$1,585,000

Monthly Est:$7,889

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon3,392sqft

90 Caiola Ct, Southold, NY 11944

$7,889/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2007

  • $29.17/mo HOA

  • 27,007 sqft lot

  • $467/sq.ft

Description

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

  • Houzeo last checked: 8 minutes ago
  • Listing updated: September 30, 2026 at 2:43 pm
  • Listing Provided by: William J. Walters CBR (631) 553-6533 | Daniel Gale Sothebys Intl Rlty (631) 477-0013
  • Source: OneKey MLS-NY | MLS#: 1027434 OneKey MLS-NY

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Suffolk County

  • City

    Southold

  • Neighborhood

    --

  • Year Built

    2007

  • HOA Fees

    $29.17/mo

  • Finished Area

    3,392 sqft

  • Lot Size

    27,007 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    1027434

  • MLS Status

    Pending

  • Days on Market

    83

  • Cumulative Days on Market

    138

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Location

HOA Management

Rockcove Estates

HOA Fees

$350/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Other Other

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Sewer

    Septic Tank

  • Cooling

    Central Air

  • Exterior Features

    None

  • Flooring

    Tile, Wood

  • Appliances

    Dishwasher, Dryer, Electric Oven, Electric Range, Exhaust Fan, Freezer, Refrigerator, Washer

  • Heating

    Forced Air, Natural Gas

  • Interior Features

    First Floor Full Bath, Cathedral Ceiling(s), Central Vacuum, Crown Molding, Double Vanity, Eat In Kitchen, Entrance Foyer, Formal Dining, High Ceilings, High Speed Internet, His And Hers Closets, Kitchen Island, Primary Bathroom, Recessed Lighting, Soaking Tub, Stone Counters, Walk In Closet(s)

Construction

  • Year Built

    Year Built: 2007

  • Home type

    Single Family Residence

  • Construction Materials

    Cedar, Fiberglass Insulation, Frame

  • Architectural Style

    Post Modern

Utilities & Energy

  • Basement

    Full, Walk Out Access

  • Parking Features

    Driveway, Garage

  • Water Source

    Public

  • Fireplace Features

    Wood Burning

  • Utilities

    Cable Connected, Electricity Connected, Natural Gas Available, Phone Connected, Underground Utilities, Water Connected

  • Laundry Features

    Laundry Room

Other Features

  • Patio And Porch Features

    Deck

  • Lot Features

    Front Yard, Landscaped, Level, Near Golf Course, Near Public Transit, Near School, Near Shops, Private

Price History

DateEventPrice

09/30/2026

Source: mls_logoOneKey MLS-NY #KEY1027434

Pending

$1,585,000

$467/sqft

09/15/2026

Source: mls_logoOneKey MLS-NY #KEY1027434

Price Decreased

$1,585,000 -6.49%

$467/sqft

08/04/2026

Source: mls_logoOneKey MLS-NY #KEY1027434

Price Decreased

$1,695,000 -5.04%

$500/sqft

07/17/2026

Source: mls_logoOneKey MLS-NY #KEY1027434

Listed for Sale

$1,785,000

$526/sqft

Nearby Homes

Based on information from OneKey MLS, through Oct 09, 2026, 11:31AM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group