The summer crowds have faded. The leaves will fall while the Hamptons and Shelter Island take on a quieter, more relaxed rhythm. From fall traditions, local events, pumpkin picking, vineyard harvests, to home and real estate updates, here are some highlights to enjoy this month.
Mark your calendar for October!
Here's what to enjoy all month long.
North Fork & Hamptons
Highlight Events
October brings plenty of family-friendly Halloween fun to the East End, from costume parades and trick-or-treating to fall festivals and pumpkin-filled afternoons.
Haunted Village at the Southampton History Museum
Enjoy a family-friendly Halloween experience at the Southampton
History Museum featuring safe trick-or-treating, live 19th-century
music, and pumpkin painting on Saturday, October 24, 2026, from
11:00 AM–4:00 PM.
Ragamuffin Parade & Carnival - Sag Harbor
Costumed children, adults, and even pets parade down Main
Street before heading to the Sag Harbor Whaling Museum
for games, activities, and music on the lawn.
Sunday, October 25, 2026. 1:30 PM 2:30 PM.
Halloween Pumpkin Trail - Sag Harbor
Children in costume can visit participating businesses
along Main Street and collect Halloween treats.
The Sag Harbor Chamber has been hosting this
tradition for more than 40 years.
Saturday, October 31. 1:30–3:30 PM
Little Lucy’s Halloween Pet Parade - Southampton
A festive Halloween tradition at Agawam
Park featuring costumed pets and family-friendly fun.
Saturday, October 24, 2026. 1PM
Beach Bar Halloween Bash - Hampton Bays
Join the Southampton Animal Shelter Foundation for a
spooky Halloween evening at Beach Bar
on Saturday, October 17, 2026. 6:00 PM–10:00 PM.
Hampton Library Annual Halloween Parade - Bridgehampton
Families are invited to dress in costume and meet at
the Hampton Library before heading out onto Main Street
to collect treats from local businesses. There will also be children's
Halloween activities at the Bridgehampton Museum.
Saturday, October 31. 10 AM
Trunk or Treat: A Halloween Party - Bridgehampton
A free afternoon of costumes, Halloween treats
and community fun hosted by the Bridgehampton
Child Care & Recreational Center and
Hayground School. Saturday, October 31. 2–5 PM
Places to pick your own pumpkins, explore local farms, and enjoy the best of fall.
Milk Pail U-Pick Farm - Water Mill
Pick-your-own pumpkins, apples and sunflowers.
Hank's Pumpkintown - Water Mill
Actual pumpkin picking from the vine, plus corn mazes,
hayrides and other fall activities.
Harbes Farms Jamesport
On-vine pumpkin picking is part of the fall season,
with a confirmed Sept. 19–20, 2026
Sunflower Festival featuring the pumpkin patch.
Lewin Farms — Calverton
Pumpkin, gourd and winter-squash picking is expected
mid/late September through late October.
Fairview Farm – Bridgehampton
Enjoy fall pumpkin picking and an eight-acre corn maze
with scenic views of Mecox Bay and the Atlantic Ocean.
The 2026 fall season is open on weekends through November 8.
September Percent Discount
Active listings eased to 1,453, with 213 new listings coming to market and 126 homes sold. A total of 157 homes went in-contract, while price changes reached 265, reflecting continued movement in pricing as buyers have more options. Homes closed at a 2.27% discount from the last list price versus 6.82% from the original list price, showing that pricing adjustments are bringing sellers much closer to where buyers are willing to transact.
After holding around 1,500 listings through the summer, inventory has begun to edge lower, while sales and contracts remain active. With the market moving deeper into fall, activity is likely to remain steady before the typical winter slowdown. For buyers, current conditions still offer a meaningful range of options, while sellers can take advantage of continued activity before the seasonal shift. Looking ahead to January, new listings will begin to replenish inventory and create another wave of opportunities.
The market and buyers are looking for consistency in interest rates. If rates remain stable, even if higher, potential buyers will continue to enter the market as rate consistency reduces potential risk.
September Hamptons & North Fork Stats
New Listings
New listings remained active in September and should continue through October, September ranged from 39 to 50 per week. Activity was strongest during the first week following Labor Day, then settled into the low 20s. As the East End moves thru the fall market, the pace of new listings should continue into November.
In Contract
Contract activity was mixed, ranging from 22 to 46, with a noticeable increase during the third week. The 46 in-contracts is encouraging and shows that buyer interest continues even after the summer season. This activity should continue to support closing activity as we move further into the fall. The activity also reflects buyers who are taking advantage of the fall market and the opportunities that come with it.
Closed Sales
Closed sales started slower after Labor Day, with 16 closings. Activity then improved, with 28 homes closing in the third week and 38 in the fourth week, before easing to 25 in the final week. This activity accounts for deals that occurred over the summer and closed in September after Labor Day.
Price Changes
Price changes remained active throughout September, ranging from 47 to 60. The lower number in the second week was followed by an increase, indicating that sellers continue to adjust pricing.
Inventory
Inventory moved between 1,521 and 1,551 throughout September, ending at 1,453 yet buyers still have a healthy selection of properties to consider. While some properties may come off the market as we move deeper into fall and winter, some sellers may decide to re-list in January 2027, the beginning of our primary Hamptons sale season.
70 S Ferry Road, Shelter Island
5 Beds | 3 Baths | 2,300 SF
$1,950,000
⭐ Also available as a winter rental!
OCTOBER 2026 - MAY 2027 $5,500/mo
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.
691 Sagg Road, Sagaponack
4 Beds | 3 Baths | Heated Pool | 2,600 SF
OCT 15, 2026 -APR 15, 2027 $32k
MD-LD 2027 $95K
JULY 2027 $42K | AUG-LD 2027 $42K
(Contact me for more 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.
24 s Midway Road, Shelter Island
4 Beds | 4 Baths | 2,775 SF
JAN 1, 2027 -APR 30, 2027 $3,500/mo
JULY-LD 2027 $95K
(Contact me for more 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, 2027 - APR 30, 2027 $15,000
SUMMER 2027
MD-LD $55K | JULY or AUGUST $29K
(Contact me for more 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.
2221 Scuttle Hole Road, Bridgehampton
6 Beds | 4.5 Baths | 3,788 SF
OCT 1 - OCT 31, 2026 $15k
MD-LD 2027 $170K
July or August 2027 $72K
Year-round Oct 1, 2026 - Oct 1, 2027 $225k
BRIDGEHAMPTON with POOL and 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.
1705 Noyack Road, Southampton
4 Beds | 4 Baths | 4,300 SF
OCTOBER $25K
(Contact me for more details)
STUNNING MODERN IN SOUTHAMPTON
Beautiful, sleek one level spacious modern 2016 fully renovated with all new furnishings and an open floor plan makes this home a very desirable rental. Located on a private 500 ft. deep. flag lot offering tranquility and privacy. The living room has a wood burning fireplace and dining area has high ceilings and open glass sliding doors to a new deck creating an impressive great room. Brand new gourmet kitchen with top of the line stainless steel appliances.The north wing of the master has an oversized master with a gorgeous marble bath with an oversized 3 head shower and soaking floating tub. In addition, this wing also offers two additional guest bedrooms with a full bath. The opposite wing has a very spacious guest studio bedroom with a private bath and separate entrance. The newly-finished lower level includes a full bath and a great play/media room. Enjoy this perfect Hampton Summer rental located close to all.
172 Narrow Lane East, Sagaponack
Compound
7 Beds | 6.5 Baths | 6,500 SF
SUMMER 2027JULY/AUG-LD $300K | JULY $150K | AUG-LD $175K
MAY 28TH - JUNE 30TH $75K
COTTAGE AVAILABLE FOR WINTER
OCT. 1, 2026 - APR 30, 2027 $55k
(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?
76 White Street, Southampton
5 Beds | 5.5 Baths | 5,400 SF
SUMMER 2027
JULY $115K | AUG-LD $125K
CLASSICALLY MODERN SOUTHAMPTON VILLAGE
Located in the heart of Southampton Village, this newly completed designer furnished 5 bedroom, new construction modern farm-style home with a loft like ultra-chic interior and soaring ceilings make this the ultimate summer Hamptons rental. Combined with a fully finished lower level which has a fifth bedroom and media room, the home has 5400sf+- of living space on 3 levels plus a detached one car garage. Enter the home on the first floor and immediately feel the open and beachy design accented with modern finishes. The vaulted ceiling, grand open living area, chic kitchen and loft used as a home office or gym, has two sets of floor to ceiling foldable glass walls that fully open in the front and to the pool area exemplifying the sense of indoor/outdoor living. Prepare a wonderful summer meal in the Sub-zero & Wolf open kitchen complete with a grand island counter and stools for casual dining. The first floor also includes one of two primary suites, a powder room and a guest en-suite bedroom. The second floor includes a second primary suite with vaulted ceilings, a large ensuite bath and walk-in closets, an additional guest ensuite bedroom and access to the loft area. Outside, the manicured villagesque grounds surround the heated gunite pool, stone patio, indoor/outdoor double sided fireplace and an outdoor shower. Explore the wonderful boutiques, shops, restaurants, and world-class beaches that Southampton Village has to offer or stay by the pool for your well deserved rest and relaxation.
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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