For discerning buyers in New York, New York, luxury real estate Long Island offers a rare blend of privacy, prestige, and lifestyle that’s hard to match anywhere in the Northeast. From the Gold Coast’s storied estates to the oceanfront compounds of the Hamptons and the vineyard-framed retreats of the North Fork, Long Island is a natural extension of Manhattan luxury living—without sacrificing access to the city. I’m Daniel S. Colomban of Skyler Realty LLC, and this guide distills what you need to know about neighborhoods, lifestyle amenities, property types, and strategy so you can move with confidence, whether you’re buying or selling at the top of the market.
Why Long Island Is the Natural Extension of New York, New York Luxury Living
If you live or work in Manhattan, Long Island puts you within easy reach of world-class beaches, deepwater marinas, private clubs, elite schools, and sprawling estates—all while staying connected to the city’s business and cultural core.
- Seamless access: The Long Island Rail Road serves express routes to Penn Station and Grand Central Madison, with prime lines through Port Washington, Great Neck, Manhasset, and Hicksville; private car service and helicopter charters can put you in East Hampton in under an hour depending on conditions. For private aviation, Republic (Farmingdale), Francis S. Gabreski (Westhampton Beach), and MacArthur (Islip) are popular choices.
- Space and privacy: Acreage, gated entries, and landscaped buffers are common at the upper tiers—features that are nearly impossible to replicate in New York City.
- Lifestyle: Ocean beaches (Southampton to Montauk), North Shore harbors (Sands Point to Oyster Bay), golf clubs (Shinnecock Hills, Maidstone, Piping Rock, Sebonack), and yachting hubs (Sag Harbor, Port Washington, Oyster Bay) anchor an elevated year-round or second-home lifestyle.
- Schools and healthcare: Top public districts (Great Neck, Manhasset, Jericho, Syosset, Roslyn) and respected private schools (Friends Academy in Locust Valley, Portledge School in Locust Valley, Chaminade in Mineola, St. Anthony’s in South Huntington) are a draw, along with comprehensive medical systems, including Northwell Health and Stony Brook Medicine.
For New York, New York buyers seeking luxury real estate Long Island, the value proposition is clear: uncompromising amenities and privacy without losing proximity to Manhattan.
The Premier Enclaves: Where to Shop for Luxury on Long Island
Long Island comprises several distinct luxury corridors. Each offers a different expression of the high-end lifestyle.
- Gold Coast/North Shore Estates
- Old Westbury, Brookville, Old Brookville, Muttontown: Grand, gated estates on multiple acres with long, tree-lined drives, tennis courts, and resort-style pools. Architecture spans Georgian, Colonial, and contemporary custom builds. School districts like Jericho, East Williston, and Locust Valley often underpin value.
- Sands Point, Kings Point, and Manhasset: Waterfront residences with skyline views, private docks (where permitted), and quick Port Washington Line access to Manhattan. Manhasset’s proximity to Americana Manhasset (luxury retail) is a frequent lifestyle consideration.
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Oyster Bay Cove, Matinecock, Locust Valley, Lloyd Harbor, and Cold Spring Harbor: Park-like estates, equestrian properties, and vintage mansions nestled near preserved woodlands and harbors. Lloyd Harbor and Cold Spring Harbor offer a blend of coastal living and historic charm.
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The Hamptons and East End
- Southampton Village, Water Mill, Bridgehampton, Sagaponack: Ocean-to-bay compounds, agricultural-reserve views, and new-construction modern farmhouses with wellness wings, screening rooms, and guest cottages. Eight-figure trades are not unusual in top locations.
- East Hampton Village and Amagansett: Cedar-shingled traditional homes and contemporary glass pavilions near the Maidstone Club and Atlantic beaches. Amagansett’s dunes neighborhoods are prized for privacy and proximity to the ocean.
- Sag Harbor Village: A year-round harbor town with historic captain’s houses, luxury new builds seamlessly integrated into the village fabric, and vibrant marinas. Boaters love the deepwater access; culture lovers enjoy its dining and arts scene.
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Montauk: For those craving an oceanfront edge, Montauk offers bluffs, surf culture, and modern residences with dramatic Atlantic vistas.
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North Fork Wine Country
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Southold, Cutchogue, Mattituck, and Peconic: Vineyard-framed estates, waterfront homes on the Peconic Bay and Long Island Sound, and a slower pace that appeals to buyers who prefer a more understated luxury profile.
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South Shore and Five Towns
- Hewlett Harbor, Lawrence, Atlantic Beach, and Lido Beach: Bayfront and canalfront residences with boat access, private beach clubs, and a tight-knit community feel.
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Merrick, Bellmore, and Massapequa waterfronts: Deepwater docks for larger vessels in select canals and peninsulas; excellent options for buyers prioritizing boating lifestyle within a convenient commute.
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New Luxury Condos and Amenities
- North Hills (The Ritz-Carlton Residences): Hotel-branded services and lock-and-leave convenience in the heart of the North Shore.
- Glen Cove’s waterfront renaissance (Garvies Point area): Newer luxury condos and townhomes with marina access and parks, appealing to those who want waterfront living without the upkeep of a single-family estate.
Each of these submarkets behaves differently. My role is to align your lifestyle priorities—waterfront versus acreage, club access, school district, commute—to the neighborhoods most likely to deliver them.
What Defines Luxury on Long Island
At the top of the market, long-term livability is just as crucial as finishes. The most successful properties typically feature:
- Estate-caliber sites: Multi-acre privacy, mature landscaping, gated entries, and outdoor programming (pool, pool house, tennis, pickleball, outdoor kitchens, and lounge pavilions).
- Architecture and craftsmanship: Custom millwork, imported stone, artisan cabinetry, and envelope upgrades like steel windows/doors and formal gardens. In the Hamptons, modern farmhouses and glass-walled contemporaries dominate new builds; on the Gold Coast, classical revival and transitional styles are strong.
- Wellness and technology: Dedicated spa/fitness suites, saunas/steam, cold plunge, infrared, and whole-home automation with security, AV, and climate zoned for efficiency.
- Sustainability: Geothermal and high-SEER systems, solar-ready roofs, EV infrastructure, and modern insulation assemblies are increasingly expected, particularly in new builds.
- Waterfront specifics: Deepwater docks, bulkheads, mooring rights where permitted, boathouses, and elevated siting for resilience. Views are capitalized with terraces, roof decks, and floor-to-ceiling glazing.
When evaluating luxury real estate Long Island, I encourage clients to weigh the interplay between site, design, and lifestyle—because the best homes deliver all three.
Waterfront and Estate Ownership: What to Know Before You Buy
Luxury on Long Island often involves unique due diligence. Here’s how I help clients navigate risk and preserve value:
- Tidal and wetlands considerations: Waterfront improvements like docks, bulkheads, and shoreline stabilization may require permits and compliance with local, state, and federal regulations. Understanding setbacks, elevation certificates, and any recorded restrictions is essential before finalizing terms.
- Flood and insurance planning: Some waterfront or low-lying properties require specialized insurance. Reviewing elevation data, recent flood map changes, and carrier options early can prevent surprises and guide offer strategy.
- Septic and environmental upgrades (East End focus): In many parts of Suffolk County, especially on the East End, advanced (I/A OWTS) septic systems are now standard for new construction and significant renovations. Budgeting for or confirming these upgrades is key for long-term usability and resale.
- Erosion and shoreline dynamics: On ocean and Sound frontages, erosion control and dune preservation are hot-button topics. I connect buyers with local engineers and surveyors to understand historic shoreline changes and permissible protective measures.
- Equestrian and acreage: For estate parcels with barns or paddocks, zoning, conservation easements, and agricultural exemptions may affect current use and future development rights. Verifying any covenants and understanding tax implications protects your plans.
- Condos and HOAs: Luxury condos and gated communities can simplify ownership with amenities and maintenance. I review offering plans, reserve studies, and rules on alterations, rentals, and pets to align with your lifestyle and investment goals.
The takeaway: Long Island’s premier properties reward preparedness. With the right team of local inspectors, attorneys, surveyors, and insurance professionals—and an agent who curates them—you buy with clarity.
The Market Now: Pricing, Inventory, and Timing
The luxury segment has remained resilient. Low inventory characterizes much of the North Shore and East End, while demand is supported by all-cash buyers and New York, New York purchasers seeking more space and coastal access. A few practical realities:
- Inventory remains tight at the top: Trophy waterfronts and new construction in prime villages are scarce. Serious buyers often pre-approve proof of funds and act decisively when the right property surfaces.
- Seasonality matters: Spring through early summer sees the heaviest list and tour activity, particularly in the Hamptons; however, strategic off-season acquisitions can yield opportunities with less competition.
- Luxury is less rate-sensitive: While interest rates influence the broader market, high-net-worth buyers frequently transact in cash or with portfolio lending, insulating prime segments from volatility.
- Off-market access is pivotal: Many high-profile sellers prefer discretion. My network at Skyler Realty LLC regularly surfaces private opportunities before they hit the open market.
Whether you’re seeking a north-shore estate under a canopy of old-growth trees or a new modern on reserved farmland in Bridgehampton, timing and preparation drive outcomes in luxury real estate Long Island.
Working With Daniel S. Colomban at Skyler Realty LLC
My clients choose me for three core reasons:
- Local insight, block by block: School district boundaries that bisect a neighborhood, a marina’s draft depth for your vessel, a street’s microclimate after a storm—these “small” details change value. I bring them forward before you commit.
- Advocacy and discretion: At the top of the market, privacy and negotiation prowess matter. I manage communication tightly, coordinate NDA-protected tours when necessary, and negotiate with a deep understanding of seller psychology in low-inventory conditions.
- Data-driven strategy with concierge service: I pair on-the-ground intel with rigorous pricing models, builder cost analysis, and rental yield scenarios where relevant. My team oversees logistics: car-to-door tours, same-day private viewings, inspections, and vendor meetings—all set to your calendar.
Skyler Realty LLC is a boutique brokerage built for high-touch representation. We keep our client roster intentionally limited so we can deliver the attention, speed, and discretion luxury buyers and sellers deserve.
Selling a Luxury Property on Long Island: How We Maximize Value
When representing sellers, I treat your property like a brand. That means:
- Story-led positioning: We surface the narrative that commands a premium—architect, landscape designer, craftsmanship details, provenance, and the lifestyle your home enables (sunrise over Gardiners Bay, equestrian trails at your back gate, quick tender to your mooring).
- Elevated presentation: Architectural photography, twilight sessions, cinematic film, measured floor plans, and immersive 3D tours designed to qualify buyers before they step through the door. Select homes benefit from print features and private broker previews.
- Precision pricing: I model comparable sales, replacement costs, and buyer pool depth to set a price that inspires urgency without leaving money on the table. In ultraprime segments, I often recommend a whisper campaign before public launch to test appetite and gather feedback.
- Private and global reach: We maintain a curated buyer list and agent network across Manhattan, Brooklyn, and established feeder markets. For high-profile listings, we use controlled, appointment-only showings and pre-qualification to protect privacy.
The result is a faster, cleaner negotiation cycle and a closing that reflects your property’s true stature.
For Investors: Rentals and Income Opportunities
Luxury investors look at Long Island for both capital preservation and optionality:
- Hamptons seasonal rentals: Peak-season weekly and monthly rates can be attractive for well-located homes with pools and beach access. Design-forward interiors, hotel-grade bedding, outdoor amenities, and proximity to village dining meaningfully impact yield.
- Year-round and shoulder-season demand: Sag Harbor and select North Fork villages attract year-round tenants drawn to community and waterfront access.
- Regulations and compliance: Towns across the East End require rental registrations and have rules governing minimum stays and occupancy. Reviewing local codes and HOA policies is essential before underwriting returns.
- 1031 and portfolio strategy: For investors repositioning assets, Long Island offers diverse replacement options—from turnkey condos with services to large estates with value-add potential. I coordinate with your attorney and tax advisor to align timing and property type.
I provide rental comps, projected occupancy calendars, and furnishing/amenity recommendations tailored to your target tenant.
Logistics: Access, Schools, Clubs, and Everyday Luxury
- Transportation: The Port Washington, Oyster Bay, Hempstead, and Ronkonkoma lines of the LIRR serve many luxury corridors, with express service to Manhattan. Major parkways (Northern State, Long Island Expressway, Meadowbrook, and Sunrise Highway) connect North Shore living to the Hamptons and South Shore beaches.
- Yachting and marinas: Manhasset Bay (Port Washington), Oyster Bay Harbor, Sag Harbor Cove, and Three Mile Harbor (East Hampton) are favorites for slips and moorings. Draft depth and tidal considerations vary—important data for larger vessels.
- Golf and clubs: From historic institutions like Shinnecock Hills, National Golf Links, and Maidstone in the Hamptons to Piping Rock, Nassau Country Club, The Creek, Glen Oaks, Meadow Brook, and Old Westbury on the North Shore, membership landscapes are nuanced and often relationship-driven.
- Equestrian and events: The Hampton Classic in Bridgehampton and trails in Old Westbury and Brookville support an active equestrian community.
- Education: In addition to standout public districts, private options like Friends Academy, Portledge, Chaminade, and St. Anthony’s are frequently on luxury buyers’ shortlists. I coordinate school tours and introductions when needed.
- Healthcare: Proximity to top-tier hospitals and specialty care is a value driver for many clients; we factor that into neighborhood selection.
These lifestyle pillars aren’t extras—they’re intrinsic to how buyers experience luxury real estate Long Island day to day.
Your Next Step
Whether you’re upgrading from a Manhattan penthouse to a waterfront compound, securing a discreet estate on the Gold Coast, or positioning your Hamptons home for a record sale, the right strategy makes all the difference. As a trusted advisor at Skyler Realty LLC, I deliver confidential, results-focused representation from first conversation to closing—and beyond.
If you’re ready to explore luxury real estate Long Island or to discuss a bespoke selling plan for your property, contact Daniel S. Colomban at Skyler Realty LLC. I’ll curate a targeted shortlist, brief you on off-market opportunities, and put a data-backed plan in motion so you can move decisively and successfully.
