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MLS ID KEY1027434Last updated Sep 30, 2026

Single Family

90 Caiola Court

Pending · Southold · Suffolk County, NY 11944

Bedrooms
4 Beds
Bathrooms
3 Baths
Year built
2007
Est. monthly taxes
$1,210.08
Property gallery0 / 38
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About this home

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.

Listing snapshot

Days on site
59 days
Listed on MLS
Jul 17, 2026
Full baths
3
Half baths
0
Annual property tax (MLS)
$14,521
Tax year
2025
Association / maintenance fees (MLS)
$350 / Annually
Fees include (MLS)
Other
Area source (MLS)
CubiCasa
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY1027434
Last updated
Sep 30, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
2007
Garage
Yes
Garage spaces
2
Parking
Driveway, Garage
Water source
Public
Sewer
Septic Tank
Utilities
Cable Connected, Electricity Connected, Natural Gas Available, Phone Connected, Underground Utilities, Water Connected

Interior features

Basement
Full, Walk-Out Access
Heating
Forced Air, Natural Gas
Cooling
Central Air
Interior
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)
Appliances
Dishwasher, Dryer, Electric Oven, Electric Range, Exhaust Fan, Freezer, Refrigerator, Washer
Flooring
Tile, Wood
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Post Modern
Construction materials
Cedar, Fiberglass Insulation, Frame
Exterior
None
Private pool
No

Schools (MLS)

Elementary school
Greenport Elementary School
Elementary school district
Greenport
Middle school
Greenport High School
Middle school district
Greenport
High school
Greenport High School
High school district
Greenport

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. MLS status changed
  3. Price changed to $1,585,000
  4. First seen on this site

Location

Southold · Suffolk County, NY 11944Show interactive map
90 Caiola Court

Southold · Suffolk County, NY 11944

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.