September has a way of making the East End feel a little more relaxed. The beaches are quieter, the villages feel less crowded, and the first signs of fall begin to appear. I've rounded up some of my favorite things to see, do, and know around the Hamptons and Shelter Island this month.
Mark your calendar for September!
Here's what to enjoy all month long.
As summer winds down, September is the perfect time to get ahead of fall and winter home needs. Here are a few local professionals homeowners should consider scheduling before the season comes to an end.
Pool Service 🏊
Schedule closing, equipment maintenance,
and winterization.
Landscaper 🌿
Service heating systems before the
first cold weather arrives.
Plumber 🚰
Check outdoor plumbing, showers, irrigation lines,
and winterization needs.
Roofer & Gutter Service 🏠
Inspect the roof and clear
gutters before fall storms.
Window & Door Professional 🪟
Check seals, screens, and weatherproofing.
Electrician ⚡
Address outdoor lighting, generators, and any
electrical projects before winter.
Pest Control 🐜
Schedule a seasonal inspection and
preventative treatment.
Housekeeping / Home Management / Handyman🧹
Arrange regular off-season visits.
Security / Smart Home Service 🔐
Make sure cameras, alarms, locks, and monitoring
systems are ready for the off-season.
Places to have apple picking, explore local farms, and enjoy the best of fall.
Milk Pail U-Pick Farm - Water Mill
A classic Hamptons fall tradition, Milk Pail offers U-Pick apples and pumpkins, with more than 20 apple varieties throughout September and October. Their official 2026 announcement lists Saturday, September 5, 2026 as opening day, with U-Pick hours Friday–Sunday, 10:00 AM–5:30 PM. Reservations are not required.
Seven Ponds Orchard — Water Mill
A charming family-friendly orchard, Seven Ponds offers U-Pick apples along with seasonal produce, sunflowers, and other fall activities. Apple picking is available during the September–October 2026 season, and the farm is generally open daily from 9:00 AM–6:00 PM; however, specific apple availability can vary, so it is best to call ahead.
Hank’s Pumpkintown — Water Mill
A popular destination for a full day of fall fun, Hank’s Pumpkintown combines apple picking with pumpkins, corn mazes, and other seasonal activities. For 2026, apple picking is offered on Saturdays, Sundays, and school holidays, generally from 9:30 AM–5:30 PM, making it especially good for a family fall outing.
Harbes Farms Jamesport
Pick your own Honeycrisp apples at this family-friendly North Fork farm, with hayrides, a corn maze, live music, and seasonal activities. Open weekends and holidays, 9:00 AM–6:00 PM, through November 1, 2026.
Woodside Orchards – Aquebogue
Enjoy fall apple picking with seasonal varieties, fresh-baked treats, and hard cider at this family-run orchard. Apple picking runs from the second week of September through October, with the exact varieties available changing throughout the season.
Lewin Farms – Calverton
Enjoy fall apple picking at this fourth-generation family farm, with apples available for U-pick from late August through October. The farm notes that picking dates and availability vary with weather and crop conditions, so visitors should call ahead to confirm.
August Percent Discount
Monthly active listings increased to 1,529, with 221 new listings coming to market a substantial increase from 197 the year prior with 125 homes sold. A total of 150 homes went in-contract, while price changes continue to increase monthly, reaching 272 yet substantially lower than the yearly comparison of 362 in August 2025. Homes closed at a 4.72% discount from the last list price versus 9.94% from the original list price, showing that sellers who adjust to current market conditions are getting closer to the price buyers are willing to pay.
The summer market ended with a healthy level of activity, particularly toward the end of August when contracts and closings picked up. Expect increases in inventory throughout September as homeowners get their homes back after renting and decide to list their homes for sale. With total inventory and new listings higher than August 2025 buyers have more to choose from than earlier in the year. As we move into fall—historically our second buying season—I expect more motivated buyers and sellers with a bit more urgency in September.
August Hamptons & North Fork Stats
New Listings
August continued to bring new listings, with 45 to 56 properties entering the market each week. The second week was the busiest at 56. Sellers continue to bring properties to market as Labor Day approaches, giving buyers new opportunities to consider for the fall market.
In Contract
Contracts stayed relatively steady, ranging from 30 to 38, with the strongest activity coming in the final week. While most buyers are already settled with purchases this summer, the continued contract activity shows that serious buyers are still in the market.
Closed Sales
Closed sales increased steadily from 21 to 30 over the course of August. With in-contracts also strengthening toward the end of the month, we should see continued closings as we move into September.
Price Changes
Closed sales increased steadily from 21 to 30 over the course of August. With in-contracts also strengthening toward the end of the month, we should see continued closings as we move into September.
Inventory
Inventory rose modestly during August and ended at 1,537, compared with 1,520 at the beginning of the month. There is more choice for buyers, but we are not seeing a dramatic buildup. Sellers need to price homes correctly in order to stay competitive in this market. If inventory remains steady or continues to rise, buyers may gain additional negotiating room.
70 S Ferry Road, Shelter Island
5 Beds | 3 Baths | 2,300 SF
$1,950,000
⭐ Also available as a winter rental!
$12K Sept. | $5,500/MO - Winter 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
SUMMER 2027
JULY/AUG-LD $300K | JULY $150K | AUG-LD $175K
MAY 28TH - JUNE 30TH $75K
COTTAGE AVAILABLE FOR WINTER
Contact me for more details
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?
2221 Scuttle Hole Road, Bridgehampton
6 Beds | 4.5 Baths | 3,788 SF
September $30K | October $15K
MD-LD 2027 $170K
July or August 2027 $72K
BRIDGEHAMPTON WITH POOL & TENNIS
Well appointed Classic Hamptons home in Bridgehampton with 5/6 bedrooms heated 20 x 40 pool. loungers, patio tables, grandstand dining and har-tru tennis. The first floor is set up with an Open Floor concept , country style gourmet kitchen, breakfast nook, sitting area with TV and double glass doors out to the expansive deck, formal living and dining area, brick fireplace and den/guest option. The second floor has 4 additional bedrooms and the primary suite with ensuite bath and a private deck overlooking the beautifully landscaped grounds, pool and tennis. Also, a inished lower level with full bath and lounge area is another added plus. Conveniently located near Bridgehampton, Sag Harbor Village and ocean beaches.
24 S Midway Road, Shelter Island
4 Beds | 4 Baths | 2,775 SF
SEPT 8 - 30 $10K | WINTER $2,500
JULY-LD 2027 $95K
CONTACT ME FOR MORE RENTAL DETAILS
SPECTACULAR WATERFRONT RENTAL & 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.
50 Bucks Path, East Hampton
4 Beds | 3 Baths | 2,000 SF
WINTER 2027
JAN 1 - APRIL 30TH $15K or $3,900/MO
SUMMER 2027
MD-LD $55K | JULY or AUGUST $29K
CONTACT ME FOR MORE RENTAL DETAILS
EAST HAMPTON SUMMER FUN
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.
691 Sagg Road, Sagaponack
4 Beds | 3 Baths | 2,600 SF
SEPT '26 $20K | WINTER $32K or $4,900/MO
MD-LD 2027 $95K
JULY 2027 $42K | AUG-LD 2027 $42K
CONTACT ME FOR MORE RENTAL DETAILS
MODERN BARN SAGAPONACK
Perfectly located between Sag Harbor night life and Sagg Main Beach day life, this chic white modern barn is completely renovated Enjoy the quiet serene setting and the fresh new sensibility. 4 bedrooms 3 baths with a media room, full guest room, full bath and laundry room in the lower level. The primary bedroom with gorgeous primary bath and mezzanine office on the second floor Living room with fireplace, dining ang open kitchen with counter seating overlook the pool and large deck. The first floor also includes 2 additional bedrooms and full bath. Fabulous summer home in Sagaponack just down the street from Wolffer Estate Vineyard and farm stands. Close to pristine white sand ocean beaches of Sagaponack, Sag Harbor and Bridgehampton.
GET IN TOUCH
Cynthia R. Barrett
LICENSED ASSOCIATE REAL ESTATE BROKER
cbarrett@bhsusa.com
917-865-9917
Ranked in the Top 1.5% of Agents Nationwide
REAL TRENDS America’s Top Real Estate Professionals
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