- May 13
- 10 min read
May is when the East End, The Hamptons and Shelter Island begin to open up for the season. People are heading outdoors where water sports, racket sports, golf, village walks and restaurants with outdoor dining are becoming active again.
Second home owners and renters officially begin their summer season on May 22nd, Memorial Day weekend.
Last minute renters continue to seek their perfect homes with a good deal of rental inventory still on the market and increasing inventory for sale.
AMERICAN REVOLUTION & BEYOND
This year’s House Tour will feature 5 extraordinary and historic Shelter Island homes. June 6th - 1:30 PM to 4 PM. Party, Raffles, 250th Exhibit and Culinary Bites catered by The Pridwin - 4-6pm.
Mark your calendar for May!
Here's what to enjoy all month long.
Relax and enjoy seasonal menus, fresh air, and vibrant village scenes throughout May.
Union Burger Bar – Southampton
A casual, lively spot known for celebrating “the most American of foods”—the burger— Union Burger Bar serves up gourmet burgers, hand-cut fries, indulgent milkshakes, and a full bar with craft beer and bourbon selections. Located at Bowden Square, it’s a go-to for relaxed dining with outdoor seating, takeout, and a fun, family-friendly atmosphere.
Nick & Toni’s – East Hampton Village
This beloved Italian restaurant offers seasonally inspired, farm-to-table cuisine in a warm Tuscan-style setting with a wood-burning oven and vibrant dining scene. Known for handmade pastas, fresh seafood, and locally sourced ingredients
Tutto il Giorno – Sag Harbor Village
A chic, upscale Italian restaurant offering authentic Southern Italian cuisine with a lively bar scene and stylish indoor-outdoor dining. Known for handmade pastas, fresh seafood, and a warm, romantic atmosphere inspired by European coastal living.
North Sea Farms - Southampton
Known for organic free-range chickens, fresh eggs, vegetables, flowers, baked goods, and local East End products.
Opening hours are daily from 8AM - 5PM
Pierre's – Bridgehampton
Enjoy elegant outdoor dining featuring classic French cuisine and a charming open-air patio. Open daily for breakfast, lunch, and dinner from 8:00 AM to 10:00 PM.
SALT Waterfront Bar & Grill – Shelter Island
Enjoy waterfront outdoor dining with fresh seafood, cocktails, and live music at SALT Waterfront Bar & Grill in Shelter Island. Open Thursday from 5:00 PM–9:00 PM, Friday–Saturday from 12:00 PM–10:00 PM, and Sunday from 12:00 PM–9:00 PM.
The 1901 Grill – Shelter Island Heights
Enjoy casual dining with scenic deck views overlooking the water, featuring American favorites and a relaxed atmosphere in Shelter Island Heights. Open Friday–Saturday from 3:00 PM–9:00 PM and Sunday from 12:00 PM–8:00 PM.
Lulu Kitchen & Bar – Sag Harbor
Experience wood-fired cuisine and lively open-air dining in the heart of Sag Harbor, featuring outdoor seating, brunch, lunch, dinner, and happy hour specials. Open daily, with brunch on Sundays from 11:30 AM–3:30 PM and dinner until 10:00 PM on Fridays and Saturdays.
Cowfish - Hampton Bays
Enjoy waterfront outdoor dining with canal-view patio seating, a large open-air bar, and seafood, sushi, and steak dishes in Hampton Bays. Open Monday–Thursday from 12:00 PM–9:00 PM, Friday until 10:00 PM, Saturday from 11:00 AM–10:00 PM, and Sunday from 11:00 AM–9:00 PM.
Rumba - Hampton Bays
Experience island-style outdoor dining on Shinnecock Bay with waterfront deck seating, tropical cocktails, Caribbean-inspired cuisine, and live music in Hampton Bays. Open daily for lunch and dinner, with extended evening hours on weekends
Having reliable service professionals in place is essential. Here are a few trusted plumbers across the Hamptons and Shelter Island that are consistently used by local homeowners and property managers.
North Sea Plumbing & Heating
Hamptons & Shelter Island
Provides full-service plumbing, heating, irrigation, and water care solutions, including installations, repairs, maintenance, and 24/7 emergency service for residential and commercial properties. Serving the Hamptons, the East End, and Shelter Island, they bring over 60 years of experience and comprehensive coverage across local communities.
Mr. Rooter Plumbing - Southampton
Offers professional plumbing services including drain cleaning, sewer and drain solutions, water heater services, and general plumbing for residential and commercial clients.
Okey Plumbing & Heating - Southampton
Provides a wide range of plumbing and heating services, including drain cleaning, fixture repairs, repiping, water heater and boiler installation, water filtration, and 24-hour emergency service for residential and commercial clients.
R. Bono Jr. Plumbing & Heating
East Hampton
Offers general plumbing repairs, maintenance, and heating services for residential properties.
R M Steffens Plumbing & Heating
Sag Harbor
Delivers comprehensive plumbing and heating services, including pipe repairs, system installations, water filtration, backflow prevention, and winterization, along with 24/7 emergency repairs.
Montauk Plumbing & Heating
Offers full-service plumbing and heating solutions, including residential and commercial plumbing, gas services, boiler installation, repairs, water main work, fire sprinklers, and new construction projects.
East Points Plumbing & Heating – Shelter Island
Providing residential and commercial plumbing and heating services across the East End of Long Island, including pipe repairs, water heater installation, heating systems, emergency plumbing, and routine maintenance. Available for 24/7 emergency service in Shelter Island Heights.
Flanders Service Experts – Hampton Bays
Providing residential HVAC, plumbing, and water treatment services throughout the East End, including AC and heating repair, heat pumps, ductwork, indoor air quality systems, water heaters, and 24/7 emergency service. Serving Hampton Bays, Bridgehampton, Sag Harbor, Shelter Island, and surrounding areas since 1954.
Additional Sources
Kyle - Watts Water Works - 631-574-8763
Bryan Philips Plumbing and Heating - 516-449-5694
Mahoney Plumbing - 631-283-2225
April Percent Discount
Active listings increased through April as new inventory entered the market place. Homes closed in April 2026 at a 4.53% discount from the last list price versus 8.72% from the original list price showing sellers were aggressively pricing their houses which resulted in large price reductions before their homes sold. This is compared to April 2025 where homes sold at their last list price of 3.75% and 4.90% of the original price where pricing was more realistic. (See highlighted graph above.)
This month inventory continued to build giving buyers more options as the market moved closer to the early summer season. Demand remained active, but buyers were more selective and price-sensitive, resulting in increased pricing adjustments and a more negotiation-driven environment.
April Hamptons & North Fork Stats
New Listings
New listings remained active throughout April, starting strong at 54 and holding within the 39 to 49 range for the remainder of the month. This steady flow reflects a continued spring push from buyers, contributing to a more competitive environment as inventory builds ahead of the early summer season.
In Contract
Contract activity ranged from 26 to 34, with a slight uptick toward the end of the period. While not accelerating sharply, this consistency indicates that buyers remain engaged and are gradually responding to the increase in available inventory.
Closed Sales
Closed sales showed a steady upward trend, moving from 22 early in the month to 32 by the final week. This progression reflects both prior deals reaching completion and continued buyer activity. With consistent contract levels in place, closed sales may continue to improve in the near term.
Price Changes
Price adjustments remained active, ranging from 44 to 63, with higher levels mid- to late month. This suggests that as competition increased, some sellers adjusted pricing to stay aligned with market expectations. Price changes also continued in order to entice new buyers to the market and existing buyers to pull the trigger on purchasing their well priced summer home.
Inventory
Inventory increased steadily from 1,426 to 1,482, reflecting the continued addition of new listings outpacing completed sales. The buildup provides buyers with more choices, while also requiring sellers to remain competitive in pricing and active marketing as the market moves closer to peak season.
21 Cove Road, Sag Harbor
4 Beds | 3.5 Baths | 3,000 SF
NOW: $4,450,000
BOOK AN APPOINTMENT
Located in the coveted Redwood waterfront community of Sag Harbor Village, this architect-designed, Victorian-style home presents a striking, modern interior. Completely renovated and expanded with 2 primary bedroom suites, the 4 bed, 3.5 bath residence showcases luxurious updates alongside captivating harbor views. Set just two blocks from Sag Harbor's vibrant Main Street, this 3,000 +/- sq. ft. house exudes classic Hamptons allure with its inviting wrap-around porch, mahogany and stone patios, high-end finishes, and impeccable attention to detail. With an open concept design, the main level encompasses a sitting area centered around a fireplace, dining area, and exquisite kitchen with island seating. Set on the second floor, two guest bedrooms and bath plus the expansive primary suite includes a spacious bathroom and private balcony. The second primary suite with exceptional bath is accessed separately also on the second floor. The finished 9 foot ceiling lower level enhances the home's versatility with an additional 500sf +/- great room featuring a lounge alongside a gym area and a pool/ping-pong table.
70 S Ferry Road, Shelter Island
5 Beds | 3 Baths | 2,300 SF
$1,950,000
RE-ENVISONED ICONIC CAPTAIN CARTWRIGHT HOUSE
Enter by way of a circular drive to this Designers own fabulous reconstruction and renovation of the Classic and Iconic Captain Cartwright House handsomely landscaped in Shelter Island. This classic 5 bedroom home, detached garage, covered porches, blue stone patios and heated 20 x 40 gunite pool with all the bells and whistles is centrally located between the South and the North Ferries and across the street from the 2350 acre Mashomack Preserve on Shelter Island. The very private setting is ideal for relaxing by the chic lounging areas around the pool or entertaining summer guests on the beautifully landscaped grounds perfect for intimate dinners. An oversized outdoor shower is a show stopper. Dine at the many new and established restaurants including Leon 1909, Vine Street Cafe, 1901, The Pridwin, The Chequit, Rams Head Inn, Isola, Sunset Beach, Marie Eiffel, Stars Cafe and Eccentric Bagel and more on the island. Golf, sail, motorboat, tennis or pickleball and enjoy the spectacular beaches the Shelter Island has to offer. This so very special get-away retreat summer or all year round is now available for sale for the first time since the re-construction and will not last.
172 Narrow Lane East, Sagaponack
Compound
7 Beds | 6.5 Baths | 6,500 SF
$150K JULY | $175K AUG-LD$325K JUL/AUG-LD
FABULOUS RE-PRICING
YOUR HAMPTONS SUMMER TO REMEMBER
SAGAPONACK HORSE FARM VIEWS
Enjoy quintessential Sagaponack farm views all Summer! This newly built Modern farm style 7 bedroom Compound for rent is a rare find in the Hamptons. It includes a 4,000sf 4 bedroom Main Farmhouse and an adjoining 2,500sf 3 bedroom Cottage exquisitely designed by Val Florio set on 1.7 pasture-like acres indicative of Sagaponack's agricultural history. The grounds boast a magnificent lawn, specimen trees and landscaping, a heated gunite pool, pool/zen pavilion with bar and a state-of-the-art pickle-ball court and volleyball station. Located across from Wolffer Estate Stables,Sagaponack's premier horse farm, around the corner from Wolffer Estate Vineyards, close to Sagaponack's world class Sagg Main Beach, the compound is a few miles from Bridgehampton and Sag Harbor Main Street shops, restaurants and marinas. The Main House first floor double height foyer sets the stage for an easy flow into the great room, dining area and open kitchen with center island , double sinks and breakfast nook. The sun filled living room opens out to an elegant covered porch for casual outdoor dining, enjoying cocktails and lounging while watching the spectacular sunsets. The upstairs includes a spacious master suite, an outdoor deck allowing for southern facing views of the horse farm and 3 additional king and queen guest bedrooms. The lower level game room is set up for endless pool and ping pong competitions or a Peloton bike ride! The 2 homes are connected via the lower level tunnel. There is also an option to rent either the Main House or the Cottage separately for your Hamptons summer to remember. What more could one ask for?
50 Bucks Path, East Hampton
4 Beds | 3 Baths | 2,000 SF
$30K JULY | $30K AUG
$40K JUNE/JULY | $50K JUL/AUG-LD
EAST HAMPTON SUMMER FUN - BEST BET
Well maintained 4 bedroom home with oversized pool. Private setting new not far from East Hampton Main Street. A special light filled home. Excellent choice for an enjoyable summer.
24 S Midway Road, Shelter Island
4 Beds | 4 Baths | 2,775 SF
$45K JULY | $60K AUG | $65K AUG-LD
$140K MD-LD
SPECTACULAR WATERFRONT RENTAL AND DOCK
Spend your summer looking at the magnificent sunsets over the expansive Menantic Creek or take a cruise around Shelter Island towards the North or South Forks with your boat or kayak and pull into the house's own deep water dock. This 4 bedroom boater's paradise was completely rebuilt and renovated in 2019. Enjoy the open floor plan with walls of glass doors leading to the waterfront deck spanning the length of the house. The light filled home has 2 primary bedrooms and two guest bedrooms on the first floor off of the vaulted and beamed great room, open and chic stainless chef's kitchen. An additional living and lounging area in the lower ground level is perfect for overflow guests with glass doors leading directly to the dock. The lower level also includes a gym, additional lounge and TV area, and a double wood burning fire hearth and pizza oven with cozy seating after a day on the water. So close to numerous beaches, intimate hotels with newly opened and refurbished restaurants including Leon1909, , Isola, The Pridwin, The Chequit, Ramshead Inn and Sunset Beach on Shelter Island or take a day trip to Sag Harbor on the South Fork or Greenport on the North Fork both serviced by 3-8 minute ferries.
2 East Brander Parkway, Shelter Island
3 Beds | 3 Baths | 2,292 SF
$35K JUL | $60K JUL/AUG-LD
$43K AUG-LD | $35K AUG
Water Dock GORGEOUS WATERFRONT WITH DEEP WATER
Awesome Silver Beach waterfront property with a private deep water dock that can accommodate up to a 45ft boat that feeds into West Neck Harbor. The 3-4 bedroom Classic Hamptons style home has an inviting covered wrap around porch, patio, outdoor shower and access to a private beach next door. The home has breathtaking water views from almost every room. The first floor open sitting room, dining and kitchen make for wonderful sun-filled living all day long while watching the shimmering waterway. Down the hall is a cozy den, first floor bedroom, bath and 2-car garage. The second floor has two large ensuite bedrooms, an office/forth bedroom, and a large deck overlooking West Neck Harbor for morning coffee or a nightcap while watching the sunrise or sunset. Enjoy a summer boater's paradise to remember!
24 Forest Crossing, Sagaponack
4 Beds | 3 Baths | 5 Half Baths | 2,292 SF
$62K Jul 23rd - Aug 16th 2026
Contact me for more rental details!
SAGAPONACK SUMMER, 48' SALT WATER POOL
Beautifully furnished newly renovated 4-bedroom home, 3.5 baths plus outdoor shower on 1.5 private acres. Micro-mini pond outside master bedroom. HDTV in every bedroom and den with cable and Apple TV. Heated 48-ft. salt water pool. Nestled within Sag Harbor, East Hampton and Bridgehampton villages. Short distance to ocean, shops, restaurants, Jitney and airport. Around the corner from Wolffer Estate Vineyard and Poxabogue Golf Course.
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