45

Homes for Rent near Pierson Middle/High School

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  • /22

    $40,000 per month

    • 4 Beds
    • 4.5 Baths
    • 3,190 Sq Ft
    • House for Rent

    1557 Millstone Rd, Sag Harbor, NY 11963

    This privately located home is waiting for you to come and enjoy! Just minutes away from the Village of Sag Harbor, restaurants and the bay beaches, this home features 4 bedrooms, 4.5 baths with an open concept. The main floor offers a primary bedroom with primary bath, a beautiful kitchen, dining and living room, as well as a family room with a fireplace and a powder room. The second floor

    Agent Photo

    Deborah Pirro

    Daniel Gale Sothebys Intl Rlty

    (631) 641-7868

    1557 Millstone Rd, Sag Harbor, NY 11963
  • /25

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • House for Rent

    15 Hamilton St, Sag Harbor, NY 11963

    This beautifully renovated home in Sag Harbor Village has 3 bedrooms, 2.5 baths, fireplace, central air, hardwood floors, and separate garage with lovely landscaped yard and patio for entertaining. Close to Haven's Beach and the village.

    15 Hamilton St, Sag Harbor, NY 11963
  • /36

    $190,000 per month

    • 4 Beds
    • 5.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    25 Deerwood Path, Sag Harbor, NY 11963

    Your Dream Hamptons Escape Awaits!Step into a world of coastal elegance and effortless luxury in this spectacular Hamptons retreat—available for summer rental, month-to-month, or year-round living. Whether you're planning an extended getaway or seeking the ultimate work-from-vacation lifestyle, this home offers everything you need and more.Flooded with natural light, the expansive open

    Karen Richter Rett Branch Real Estate Group

    25 Deerwood Path, Sag Harbor, NY 11963
  • /23

    $100,000 per month

    • 3 Beds
    • 4 Baths
    • House for Rent

    28 Cliff Dr, Sag Harbor, NY 11963

    This gorgeous coastal cottage comes fully furnished, and is located in the very special Sag Harbor community of Bay Point. It's just been completely renovated, perfect in every way, and ready for you to move in. Enjoy glimpses of Noyac Bay from the open floor plan living room and custom kitchen with Fisher Paykel appliances. The three ensuite bedrooms are thoughtfully laid out, with each bedroom

    28 Cliff Dr, Sag Harbor, NY 11963
  • /24

    $100,000 per month

    • 6 Beds
    • 6.5 Baths
    • 5,500 Sq Ft
    • House for Rent

    51 Brandywine Dr, Sag Harbor, NY 11963

    This traditional-style Sag Harbor Village residence offers approximately 5,500 SF± across three finished levels on a beautifully landscaped half-acre. With 6 bedrooms, 6 full bathrooms, and 1 half bathroom, the home seamlessly blends classic Hamptons charm with modern luxury. Inside, the open layout features a living room with a fireplace, a dining room, an eat-in kitchen, and a sitting room, all

    Jennifer Ponzini Douglas Elliman Real Estate

    51 Brandywine Dr, Sag Harbor, NY 11963
  • /10

    $84,000 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    26 Meadowlark Ln, Sag Harbor, NY 11963

    This newly available Sag Harbor Village rental offers easy living in the heart of it all. With two bedrooms, bright and functional interiors, and a relaxed, unfussy style, it's the ideal in-town escape. Step outside and you're moments from Main Street's shops, restaurants, and marinas-yet tucked away on a peaceful street that feels worlds apart. The perfect base for enjoying village life, with

    26 Meadowlark Ln, Sag Harbor, NY 11963
  • /14

    $8,500 per month

    • 5 Beds
    • 2 Baths
    • 10,019 Sq Ft
    • House for Rent

    1 Dogwood St, Sag Harbor, NY 11963

    Imagine life unfolding in the very heart of Sag Harbor, where village charm meets everyday convenience. This isn't just a rental; it's your invitation to secure a beautifully located home with ample space, available for you to cherish all year long! Nestled at 1 Dogwood Lane, Sag Harbor, NY, this residence boasts an absolutely unbeatable location, offering the quintessential Sag

    Elizabeth Cordova Alata Douglas Elliman Real Estate

    1 Dogwood St, Sag Harbor, NY 11963
  • /20

    $80,000 per month

    • 4 Beds
    • 5 Baths
    • House for Rent

    19 Ezekillis Hollow, Sag Harbor, NY 11963

    Spend August in a setting designed for the ultimate Hamptons summer. This fully renovated North Haven Point waterfront home offers a seamless flow of indoor-outdoor living, with every space oriented toward the water and its unforgettable sunsets. The open, sunlit main level features a stunning chef's kitchen with quartzite counters-perfect for preparing memorable summer meals-alongside a

    19 Ezekillis Hollow, Sag Harbor, NY 11963
  • /32

    $75,000 per month

    • 3 Beds
    • 3 Baths
    • 1,848 Sq Ft
    • House for Rent

    15 Mount Misery Dr, Sag Harbor, NY 11963

    Indulge in Design: Hamptons Summer Rental Experience the magic of Sag Harbor Village has to offer in this charming Hamptons Designer Retreat just moments from Heavens beach-Indulge in design and sophistication in this Hamptons summer rental. Nestled in the charming enclave of Sag Harbor Village, experience world-class dining, art galleries, and a vibrant cultural scene of stunning natural beauty.

    Elizabeth Cordova Alata Douglas Elliman Real Estate

    15 Mount Misery Dr, Sag Harbor, NY 11963
  • /17

    $42,000 per month

    • 2 Beds
    • 2 Baths
    • House for Rent

    37 Trout Pond Rd, Sag Harbor, NY 11963

    Newly renovated in 2025, this adorable 2-bedroom, 1.5-bath cottage is the perfect Hamptons getaway. Just a short distance to Long Beach and 5 minutes to Sag Harbor Village, the home features a king-bedded primary suite with an ensuite half bath, all new appliances, and stylish, fully furnished interiors. Set on a private, quiet lot, surrounded by nature. It's cozy, comfortable, and the perfect

    37 Trout Pond Rd, Sag Harbor, NY 11963
  • /15

    $4,500 per month

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • House for Rent

    35 Bayberry Ln, Sag Harbor, NY 11963

    Amazing Winter Rental with a Perfect Location in Sag HarborWelcome to your new Sag Harbor lifestyle! Tucked away on a quiet cul-de-sac, this home is the perfect blend of peaceful living and prime location, just moments from everything you love about the Hamptons. The moment you step inside this charming beach cottage, you're greeted by an open floor plan bathed in natural light, creating a

    Elizabeth Cordova Alata Douglas Elliman Real Estate

    35 Bayberry Ln, Sag Harbor, NY 11963
  • /20

    $35,000 per month

    • 4 Beds
    • 3 Baths
    • House for Rent

    4056 Noyack Rd, Sag Harbor, NY 11963

    Be the first to experience a luxurious summer escape in Sag Harbor at this newly furnished, never-before-rented, coastal Cape. With four well-appointed bedrooms-three offering king-size beds and their own TVs, and a fourth featuring a twin trundle and crib-this home provides comfort and convenience for all. The primary en-suite features an oversized closet, a luxurious soaking tub, a separate

    4056 Noyack Rd, Sag Harbor, NY 11963
  • /33

    $130,000 per month

    • 4 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • House for Rent

    28 Windermere Dr, Sag Harbor, NY 11963

    4 BR Modern Sag Harbor Rental - Bay PointSag Harbor Rental - Bay Point Spend your summer in style at this beautifully updated 4-bedroom, 3-bath rental in the coveted waterfront community of Bay Point, Sag Harbor. Just minutes from the village and a moments from Foster Memorial Beach, this tastefully appointed home offers a perfect blend of modern comfort and Hamptons charm. Step inside to an

    Craig Beem Brown Harris Stevens Hamptons

    28 Windermere Dr, Sag Harbor, NY 11963
  • /20

    $25,000 per month

    • 4 Beds
    • 3 Baths
    • House for Rent

    36 Hamilton St, Sag Harbor, NY 11963

    Step behind the gate and into this private village getaway, where sun-drenched Provençal tones, lush gardens, and timeless charm set the scene for a summer to remember. This one-of-a-kind home brings together two historic 1800s houses, masterfully combined into a single, design-forward retreat. Inside, it's all curated details and unexpected moments-from the secret bar tucked behind a panel in

    36 Hamilton St, Sag Harbor, NY 11963
  • /22

    $15,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    2723 Deerfield Rd, Sag Harbor, NY 11963

    Welcome to an exquisite Sag Harbor retreat, perfectly situated on a quiet lane in the coveted Noyac area. This home is a testament to the ideal Hamptons lifestyle, offering a stunning blend of convenient location, timeless elegance, and modern luxury. Recently and meticulously renovated, it’s an opportunity to own a turnkey property that feels both completely fresh and perfectly

    Elizabeth Cordova Alata Douglas Elliman Real Estate

    2723 Deerfield Rd, Sag Harbor, NY 11963
  • /16

    $180,000 per month

    • 4 Beds
    • 3 Baths
    • House for Rent

    46 Cliff Dr, Sag Harbor, NY 11963

    Super stylish, fully renovated Sag Harbor designer masterpiece for discerning Hampton-goers. Main floor has open kitchen, living room with fireplace, den that can be converted to guest room and full bath, topped off by a sexy master suite and spa bath. Two large decks with water views offer amazing sunsets over the bay beach. Lower level has sitting area with kitchenette, two bedrooms, full

    46 Cliff Dr, Sag Harbor, NY 11963
  • /32

    $19,999 per month

    • 5 Beds
    • 3 Baths
    • 3,600 Sq Ft
    • House for Rent

    170 Northside Dr, Sag Harbor, NY 11963

    Trees, foliage, and a long driveway await you as you open the gates to 170 Northside Drive. Located Conveniently 5 mins to Sag Harbor Town Beach! As the door opens, you are greeted by a grand foyer with vaulted ceilings and an elegant chandelier. Off the foyer is a living room with a wood-burning fireplace, a gracious dining room with floor-to-ceiling French doors leading to a stone patio, an

    Domenick Cartelli Nest Seekers International LLC

    170 Northside Dr, Sag Harbor, NY 11963
  • /20

    $135,000 per month

    • 4 Beds
    • 3 Baths
    • House for Rent

    11 Henry St, Sag Harbor, NY 11963

    Graceful and beautiful 1830 Greek Revival home on .22 acres, and once the first Presbyterian parsonage, is where old charm still abounds! Although there are modern updates such as central air, many of the original details, including timeless pocket doors, wide plank wood flooring, and five fireplaces, are preserved. The original front door welcomes you into the classic living room with fireplace

    11 Henry St, Sag Harbor, NY 11963
  • /22

    $30,000 per month

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • House for Rent

    23 Marjorie Ln, Sag Harbor, NY 11963

    Waterfront SunsetsEscape to the tranquility of waterfront living with this 2 bedroom 2 bathroom cottage - perfect for those who crave stunning sunsets, serene waters and nature. Nestled right on the water this cozy haven offers endless relaxation and summer entertainment, whether you are hosting friends or enjoying a quiet retreat. Amazing sunsets - Enjoy breathtaking views every evening from

    Elizabeth France Brown Harris Stevens Hamptons

    23 Marjorie Ln, Sag Harbor, NY 11963
  • /16

    $35,000 per month

    • 4 Beds
    • 4 Baths
    • House for Rent

    41 Rawson Rd, Sag Harbor, NY 11963

    This beautiful 4 bedroom home in a special bayfront enclave in Sag Harbor is steps away from the residents-only beach. Spacious 4 bedrooms and 3.5 baths on an acre of manicured grounds, with immense outdoor space for summer entertaining - think pool parties, afternoon barbeques, and dinner parties under the summer stars. Open floor plan includes eat-in kitchen, light-filled, two-story great room

    41 Rawson Rd, Sag Harbor, NY 11963
  • /20

    $75,000 per month

    • 6 Beds
    • 6.5 Baths
    • 5,000 Sq Ft
    • House for Rent

    29 Bittersweet Ln, Sag Harbor, NY 11963

    NEW TO MARKET. ENDLESS WATERFRONT VISTAS & ICONIC SUNSETS. Water views from almost every room! This sprawling home has it all. Open concept floor plan perfect for entertaining. Main floor features larger than life eat in kitchen, sun room, sunken living room, open concept living and dining, powder, laundry, extra large primary suite with walk in closet and XL en suite bathroom. 2nd floor features

    Matthew Melinger Brown Harris Stevens Hamptons

    29 Bittersweet Ln, Sag Harbor, NY 11963
  • /20

    $40,000 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    32 Poplar St, Sag Harbor, NY 11963

    Newly renovated and impeccably designed Sag Harbor light filled home includes an open kitchen/dining room with 3 bedrooms and 2 baths. Heated Pool. Outdoors is a screened in patio as well as an adjacent brick patio and beautifully landscaped private yard. Enjoy summer from this quiet tree lined street just a few blocks from a lovely bay beach, Cromer's Market, wine store and several restaurants.

    32 Poplar St, Sag Harbor, NY 11963
  • /47

    $250,000 per month

    • 8 Beds
    • 7.5 Baths
    • 8,000 Sq Ft
    • House for Rent

    780 Sagg Rd, Sagaponack, NY 11962

    Welcome to your luxurious retreat in Sagaponack, where tranquility meets sophistication. This newly built, eight-bedroom, seven-bath home is a testament to modern elegance, boasting high-end finishes and designer furnishings throughout. Situated on nearly 3 acres of lush vibrant landscaping, privacy abounds in this sanctuary, offering a serene escape from the hustle and bustle of everyday life.

    Maida Srdanovic Compass Greater NY LLC

    780 Sagg Rd, Sagaponack, NY 11962
  • /15

    $180,000 per month

    • 4 Beds
    • 4 Baths
    • House for Rent

    6 Sunset Dr, Sag Harbor, NY 11963

    Beautifully renovated 4 bedroom, 3.5 bath contemporary with bay views from second floor living room. Open floor plan, with professional kitchen, marble countertops, and stainless steel appliances. Additional office space with futon. Bathrooms are also all recently renovated. Short distance to Long Beach and minutes from Sag Harbor Village! [[Rental Registration # RP241233]]

    6 Sunset Dr, Sag Harbor, NY 11963
  • /37

    $45,000 per month

    • 4 Beds
    • 3 Baths
    • 3,293 Sq Ft
    • House for Rent

    8 S Harbor Dr, Sag Harbor, NY 11963

    Welcome to the perfect summer escape in the heart of Sag Harbor nestled in the exclusive Bay Haven waterfront community all just moments from Sag Harbor Village. With 115 feet of private water frontage and your own dock, this serene retreat sits at the edge of Sag Harbor Bay, offering unobstructed vistas of the village skyline and breathtaking sunset views. Enjoy access to Bay Haven's private

    Thomas Cavallo Douglas Elliman Real Estate

    8 S Harbor Dr, Sag Harbor, NY 11963
  • /18

    $30,000 per month

    • 5 Beds
    • 5 Baths
    • House for Rent

    34 Redcoats Ln, Sag Harbor, NY 11963

    Nestled in a prestigious section of Sag Harbor, this exceptional 5-bedroom, 4.5-bathroom residence offers the perfect combination of elegance, privacy, and modern living. Set on over two acres of lush grounds, this rental has a host of luxurious features that will make you feel right at home. Inside, the large chef's kitchen will delight the most discerning cook, flowing into the dining room

    34 Redcoats Ln, Sag Harbor, NY 11963
  • /19

    $75,000 per month

    • 5 Beds
    • 5.5 Baths
    • 5,500 Sq Ft
    • House for Rent

    19 Fairlea Ct, Sag Harbor, NY 11963

    ELEGANT GAMBREL-STYLE IN PRIVATE COMMUNITYThis luxurious 5-bedroom, 5.5-bath traditional home blends timeless architecture with every modern amenity. Nestled on 2 meticulously landscaped acres, the residence offers over 5,500 square feet of finely appointed living space. The grand foyer opens to a formal living room with a fireplace and an elegant dining room, ideal for entertaining. At the rear

    Elizabeth Phenis Brown Harris Stevens Hamptons

    19 Fairlea Ct, Sag Harbor, NY 11963
  • /17

    $40,000 per month

    • 6 Beds
    • 5 Baths
    • House for Rent

    116 Bay St, Sag Harbor, NY 11963

    Sited on a gentle rise across the street from the Village beach, this stunning, award-winning restoration of a 1885 updated Traditional "Sea Breeze" has been totally restored to its original splendor with the added benefits and comforts of today's amenities. Five bedrooms in the main house and an additional guest suite with bath in the pool house/guest cottage provide comfortable

    116 Bay St, Sag Harbor, NY 11963
  • /18

    $25,000 per month

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • House for Rent

    16 Payne Ave, Sag Harbor, NY 11963

    Chic & Spacious Sag Harbor Summer Retreat with Saltwater PoolAvailable: June 22 - August 22 | Special Offer: August 1-14 for $10,000 Escape to tranquility in this beautifully renovated Sag Harbor home, perfectly located on a quiet cul-de-sac just 1 mile from Long Beach and 2 miles from the boutiques and restaurants of Sag Harbor Village. This bright and airy residence offers the ideal setting for

    Elizabeth Phenis Brown Harris Stevens Hamptons

    16 Payne Ave, Sag Harbor, NY 11963
  • /20

    $165,000 per month

    • 5 Beds
    • 6 Baths
    • House for Rent

    173 Bay St, Sag Harbor, NY 11963

    5,500+- sf New 5 bedroom, 5 1/2 bath A modern perspective on a classic Sag Harbor home home is set on shy 1/2 acre in the heart of Sag Harbor Village. Manicured lawn and hedges provide a serene lifestyle with covered porches, patios, outdoor living and dining with fireplace inside and out, gunite heated pool and designer finishes throughout. Conveniently located adjacent to village reserve

    173 Bay St, Sag Harbor, NY 11963
  • /21

    $35,000 per month

    • 4 Beds
    • 3 Baths
    • 2,323 Sq Ft
    • House for Rent

    4056 Noyac Rd, Sag Harbor, NY 11963

    *** Available for 2 week time periods*** Be the first to experience a luxurious summer escape in Sag Harbor at this newly furnished, never-before-rented, coastal Cape. With four well-appointed bedrooms—three offering king-size beds and their own TVs, and a fourth featuring a twin trundle and crib—this home provides comfort and convenience for all.The primary en-suite features an oversized

    Christa Kearns Corcoran

    4056 Noyac Rd, Sag Harbor, NY 11963
  • /20

    $52,800 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    3766 Noyack Rd, Sag Harbor, NY 11963

    This Hamptons classic 3 bedroom 2 bath cottage offers charm, convenience and is situated near Long Beach (Foster Memorial Beach) for those beautiful sunny beach days and amazing sunsets. This great Sag Harbor location is just under 10 minutes away from Sag Harbor village with its amazing restaurants and shops. Don't miss out on this one... [[Rental Registration # RP240316]]

    3766 Noyack Rd, Sag Harbor, NY 11963
  • /4

    $5,800 per month

    • 2 Beds
    • 2 Baths
    • 750 Sq Ft
    • House for Rent

    200 Division St Unit 2C, Sag Harbor, NY 11963

    City-style living in this 2-bedroom, 2-bath apartment, located on the second floor of a mixed-use building in Sag Harbor Village. With abundant natural light, the space offers the comfort and convenience of a city apartment paired with the charm of the Hamptons. The apartment features light-filled rooms, living area, and an equipped kitchen-perfect for relaxing or entertaining. Both bedrooms are

    Jessica Von Hagn Compass

    200 Division St Unit 2C, Sag Harbor, NY 11963
  • /20

    $45,000 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    28 Eastview Ct, Sag Harbor, NY 11963

    Meticulous very private 3 bedroom, 2 bath home with heated pool, outdoor shower and new landscaping. One floor living situated on a 1 plus acre lot at the end of a cul-de-sac. Recently renovated new kitchen and baths, nicely furnished, open floor plan, minutes to Long Beach, Sag Harbor Village stores and restaurants. The perfect summer home. Owner/agent [[Rental Registration # RP250366]]

    28 Eastview Ct, Sag Harbor, NY 11963
  • /10

    $115,000 per month

    • 4 Beds
    • 3 Baths
    • 1,572 Sq Ft
    • House for Rent

    32 Sunset Dr, Sag Harbor, NY 11963

    Discover this stunning home in the desirable Baypoint community, now available for seasonal or year-round living. This property features a brand-new entertaining area perfect for gatherings, alongside a beautifully crafted in-ground gunite pool that invites relaxation and fun. With four spacious bedrooms and three well-appointed baths, this home combines comfort and style. Enjoy

    Clare Ambrose Au Dela Real Estate LLC

    32 Sunset Dr, Sag Harbor, NY 11963
  • /11

    $3,500 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    54 Howard St, Sag Harbor, NY 11963

    Charming cottage in the heart of Sag Harbor Village available for off-season rental from October 1, 2025 to May 31, 2026. It is not available for year-round rental. Close walking proximity to Main Street, galleries, fine restaurants, Bay Street Theater, and newly renovated Cinema. Eat-in kitchen, living room plus a separate den, 2 bedrooms, and bath. Spacious backyard. Included are TV, VCR,

    54 Howard St, Sag Harbor, NY 11963
  • /12

    $55,000 per month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    51 Stoney Hill Rd, Sag Harbor, NY 11963

    This charming two bedroom one bathroom home with private office is newly renovated and a short distance to Long Beach and the Village. Come and relax in this tranquil outdoor space among nature. The brand new kitchen and living area is the perfect place to relax and cook amazing meals throughout the summer. Don't miss this amazing retreat close to all.

    Clare Ambrose Au Dela Real Estate LLC

    51 Stoney Hill Rd, Sag Harbor, NY 11963
  • /20

    $115,000 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    54 Pheasant Rd, Sag Harbor, NY 11963

    Light-filled architect designed modernist home features an open floor plan with 3 bedrooms, 2 baths, kitchen, dining room and living room with a fireplace that faces a wall of glass with its own private deck. The beautifully heated pool offers maximum seclusion and privacy and is well suited for entertaining. This home is centrally located between Sag Harbor and Bridgehampton village shops,

    54 Pheasant Rd, Sag Harbor, NY 11963
  • /17

    $15,000 per month

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • House for Rent

    112 Laurel Valley Dr, Sag Harbor, NY 11963

    Welcome to beautiful 112 Laurel Valley Drive, your destination to enjoy all that Sag Harbor has to offer. This is also a perfect launch pad to explore Southampton, Bridgehampton, some of the worlds best ocean and bay beaches, shops and the restaurants that The Hamptons are known for. Majestically set upon a hill, this home provides a private back yard with a heated in-ground pool that is a

    Robert Wilner Douglas Elliman Real Estate

    112 Laurel Valley Dr, Sag Harbor, NY 11963
  • /20

    $60,000 per month

    • 3 Beds
    • 3 Baths
    • House for Rent

    23 Bayview Rd, Sag Harbor, NY 11963

    Sag Harbor Bayfront home with dock and sandy beach. Enjoy summer sunsets from this stunning three bedroom, three bathroom home. Primary en-suite bedroom with two large terraces overlooking Sag Harbor Bay. Minutes to Sag Harbor Village and Long Beach. [[Rental Registration # RA251582]]

    23 Bayview Rd, Sag Harbor, NY 11963

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How to Rent a Home