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Southold, NY Houses for Rent

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  • /22

    $6,500 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • House for Rent

    400 Town Creek Ln, Southold, NY 11971

    Charming 2-Bedroom, 1-Bath Cottage in Southold – Perfect for Seasonal or Annual RentalsExperience the idyllic escape of this enchanting cottage, offering endless charm and privacy on a beautiful 1.5-acre property in sought-after Southold. This cozy residence features two inviting bedrooms and a well-appointed bathroom, making it ideal for relaxing getaways or year-round living.Private and

    Agent Photo

    Nicholas Accardi

    Hartford Homes & Estates of LI

    (631) 489-8119

    400 Town Creek Ln, Southold, NY 11971
  • /32

    $20,000 Per Month

    • 4 Beds
    • 4 Baths
    • 3,585 Sq Ft
    • House for Rent

    580 Gin Ln, Southold, NY 11971

    Wonderful opportunity to spend time in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the community's private bay beach. There is more than ample space to host in this brightly renovated cape with room for everyone. The main level is comprised of a lounge area with fireplace and dry bar, an open kitchen and a large great

    Scott Bortzner Compass Greater NY LLC

    580 Gin Ln, Southold, NY 11971
  • /20

    $15,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,750 Sq Ft
    • House for Rent

    1854 N Bayview Rd, Southold, NY 11971

    Last Minute deal on Summer rental. Amazing location with private beach, amazing waterviews and a private dock! Home is fully furnished and has 2 bedrooms, 2 full bathrooms and a 1/2 bathroom. Bring your boat or kayaks!

    Isaac Israel Richmond Realty Corp

    1854 N Bayview Rd, Southold, NY 11971
  • /18

    $22,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    2845 Hobart Rd, Southold, NY 11971

    Mint mid-century modern cottage offering 3 bedrooms and 2 baths, ideally located just 100 yards from sandy Founders Landing beach. The interior features clean, modern lines, anchored by a fireplace and expansive picture windows that fill the space with natural light and capture beautiful water views. Outdoors, your backyard with fire pit and outdoor shower creates an ideal setting for summer

    Eric Elkin Compass Greater NY LLC

    2845 Hobart Rd, Southold, NY 11971
  • /20

    $55,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 2,750 Sq Ft
    • House for Rent

    7635 Main Bayview Rd, Southold, NY 11971

    Elegant Historic Home in Southold – Coastal Charm Meets Modern Luxury Escape to the North Fork and enjoy this beautifully restored historic Southold home, perfectly blending timeless elegance with every modern comfort. This spacious retreat features 5 bedrooms and 3.5 baths, ideal for families or groups seeking a serene getaway. Enjoy central air conditioning, high-speed internet, and five smart

    Mary Terry MCKENNASHEA LLC

    7635 Main Bayview Rd, Southold, NY 11971
  • /20

    $20,000 Per Month

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

    465 Tarpon Dr, Southold, NY 11971

    This elegant mid-century coastal charming North Fork rental is nestled in Southold Shore Community with a bayfront beach, marina and water access for launching a kayak. This chic and sophisticated modern home has been completely renovated and sits on a private road with a manicured front lawn and a two car garage. Enjoy your cup of coffee or lunch on the beautiful large deck overlooking a

    Maryse Bransfield William Raveis New York LLC

    465 Tarpon Dr, Southold, NY 11971
  • /19

    $28,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    1100 Pine Ave, Southold, NY 11971

    Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement

    Colin McCarthy Thomas J McCarthy Real Estate

    1100 Pine Ave, Southold, NY 11971
  • /21

    $60,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    355 Windjammer Dr, Southold, NY 11971

    This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach!

    Sheri Winter Parker Corcoran

    355 Windjammer Dr, Southold, NY 11971
  • /26

    $15,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • House for Rent

    1000 Rambler Rd, Southold, NY 11971

    Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Fully Furnished. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Available July $15,000, August-Labor Day $20,000, July-Labor Day $35,000, utilities included.

    Pamela Hunt Colony Realty

    1000 Rambler Rd, Southold, NY 11971
  • /45

    $10,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • House for Rent

    1275 the Esplanade, Southold, NY 11971

    STUNNER 4BR DESIGNER HOME ~ PET FRIENDLY, HEATED POOL & BEACH!Fabulous Lux Vacations on the coveted Esplanade in "Angel Shores", with a deeded sandy bay beach and heated freeform lagoon pool with a waterfall. Property is fully fenced and private, with many lounge areas for sunning, a shady pergola when needed, and a great new outdoor shower. We offer a pet friendly policy, rare for an

    Kate Carpluk William Raveis New York LLC

    1275 the Esplanade, Southold, NY 11971
  • /22

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    440 Longview Ln, Southold, NY 11971

    Experience effortless one-level living in this immaculate Southold retreat. Set in the coveted Terry Waters community with its own sandy beach just down the road, this clean, airy home offers comfort, privacy, and classic North Fork charm. A welcoming front porch opens to an inviting living room and a spacious den featuring hardwood floors and a wood-burning fireplace. The dining area flows into

    Ryan McQueeney True North Realty Luxury Homes

    440 Longview Ln, Southold, NY 11971
  • /20

    $25,000 Per Month

    • 3 Beds
    • 4 Baths
    • 2,600 Sq Ft
    • House for Rent

    2045 Lake Dr, Southold, NY 11971

    Offered June $15,000; July $25,000; August $30,000; September $20,000; October $15,000. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is

    Janet Markarian Daniel Gale Sothebys Intl Rlty

    2045 Lake Dr, Southold, NY 11971
  • /17

    $6,000 Per Month

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

    215 Leon Rd, Southold, NY 11971

    Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plus an additional bedroom and full bath. The well-equipped kitchen opens to the dining and living rooms, where a cozy fireplace adds charm and warmth. Sliding glass doors lead to a deck overlooking a large backyard, perfect for

    Jeanmarie Bay William Raveis New York LLC

    215 Leon Rd, Southold, NY 11971
  • /32

    $30,000 Per Month

    • 6 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • House for Rent

    1695 Old Woods Path, Southold, NY 11971

    Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a

    Nicholas Planamento William Raveis New York LLC

    1695 Old Woods Path, Southold, NY 11971
  • /10

    $4,000 Per Month

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft
    • House for Rent

    8515 Soundview Ave, Southold, NY 11971

    Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quiet mornings with water views and spend your days kayaking, paddle boarding, or fishing right from your backyard. Barbecue and dine on the spacious deck with a sunset view of the lake. Ideally situated just moments from Kenny's

    Nicole Fitzgerald Signature Premier Properties

    8515 Soundview Ave, Southold, NY 11971
  • /14

    $25,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • House for Rent

    2662 Paradise Shores Rd, Southold, NY 11971

    Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning,

    JoAnn Wind Daniel Gale Sothebys Intl Rlty

    2662 Paradise Shores Rd, Southold, NY 11971
  • /15

    $3,500 Per Month

    • 2 Beds
    • 1 Bath
    • House for Rent

    3825 S Harbor Rd, Southold, NY 11971

    Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2025 Rates: January- April $3500, May $5000, June $7000,

    Barbara Poliwoda Douglas Elliman Real Estate

    3825 S Harbor Rd, Southold, NY 11971
  • /19

    $4,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    1975 Youngs Ave, Southold, NY 11971

    This beautifully furnished farmhouse offers you a warm welcome home on the North Fork. Amazing decor throughout every room for you to enjoy your stay. There are three bedrooms and two full bathrooms, hardwood floors, central air conditioning, and a back deck overlooking a fenced in yard. Great location just one block from the town restaurants, shops, and all transportation. Numerous beaches to

    Barbara Poliwoda Douglas Elliman Real Estate

    1975 Youngs Ave, Southold, NY 11971
  • /30

    $30,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    365 Chablis Path, Southold, NY 11971

    Space, Luxury, and Privacy Await in This Stunning Contemporary Home! Experience the perfect blend of elegance and comfort in this beautiful home, offering an expansive backyard ideal for dining, lounging, and entertaining. Enjoy endless hours of relaxation in the inground pool, or gather with loved ones in the spacious yard. A charming gazebo provides a welcome retreat from the sun, weather, or

    Diane Arpaia Signature Premier Properties

    365 Chablis Path, Southold, NY 11971
  • /31

    $16,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • House for Rent

    75 Clearview Ave, Southold, NY 11971

    2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal

    William Walters Daniel Gale Sothebys Intl Rlty

    75 Clearview Ave, Southold, NY 11971
  • /29

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    250 Wesland Rd, Southold, NY 11971

    JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS -SUPER COMFORTABLE CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING OUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! Additional information: Appearance excellent! Lease

    Marie Beninati Beninati Associates

    250 Wesland Rd, Southold, NY 11971
  • /22

    $30,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,233 Sq Ft
    • House for Rent

    1700 Cedar Dr, Southold, NY 11971

    2026 Availability: June $30,000. July RENTED. Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an open floor plan, large screened-in porch, full finished basement, wood burning fireplace, outdoor shower, and a saltwater, gunite pool. The primary bedroom has a large roof deck overlooking the pool and rear yard. Bedrooms and full

    Shane Hafer Compass Greater NY LLC

    1700 Cedar Dr, Southold, NY 11971
  • /17

    $9,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    1265 Brigantine Dr, Southold, NY 11971

    Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor

    Barbara Poliwoda Douglas Elliman Real Estate

    1265 Brigantine Dr, Southold, NY 11971
  • /28

    $7,500 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    3400 Youngs Ave, Southold, NY 11971

    Beautifully renovated North Fork farmhouse retreat blending relaxed luxury with resort-style outdoor living. Set on a private, tree-lined property, the home features a heated saltwater pool, expansive lawn, dramatic landscape lighting, and multiple indoor/outdoor entertaining spaces designed for unforgettable summer living. Thoughtfully updated interiors, a detached pool house, and curated

    Thomas McCarthy Thomas J McCarthy Real Estate

    3400 Youngs Ave, Southold, NY 11971
  • /33

    $36,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,769 Sq Ft
    • House for Rent

    450 Sterling Woods Ln, Southold, NY 11971

    Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Bedrooms and Hall Bath on Second

    Paul Loeb Douglas Elliman Real Estate

    450 Sterling Woods Ln, Southold, NY 11971
  • /42

    $4,900 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    6710 Soundview Ave, Southold, NY 11971

    Enjoy Southold this Summer at a Sleek Scandinavian Style Farm Ranch. Available for Bi-Weekly Rental Only. The Rate is Weekly at a Bi-Weekly Minimum. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout.

    Rene Giacobbe Douglas Elliman Real Estate

    6710 Soundview Ave, Southold, NY 11971
  • /24

    $15,000 Per Month

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

    935 Corey Creek Ln, Southold, NY 11971

    Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorated and impeccably finished, this residence offers three bedrooms, four full bathrooms, a bonus room, and a beautifully finished lower level with an additional private half bath. Step outside to your own private retreat featuring

    Melissa Principi Douglas Elliman Real Estate

    935 Corey Creek Ln, Southold, NY 11971
  • /21

    $22,500 Per Month

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

    270 N Sea Dr, Southold, NY 11971

    Southold, North Fork: Endless sunsets await at this exceptional vacation rental, available year-round with flexible terms and rates. Ideally located in the sought-after Kenny’s Beach community, this sun-drenched home is surrounded by wide sandy dunes perfect for walking, birdwatching, swimming, and relaxing days by the shore.Immaculately maintained, the residence offers 4 bedrooms and 3 full

    Nicholas Planamento William Raveis New York LLC

    270 N Sea Dr, Southold, NY 11971
  • /20

    $13,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,300 Sq Ft
    • House for Rent

    215 Northfield Ln, Southold, NY 11971

    Permit 0681- Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. BOOK NOW FOR SUMMER 2026. Terms & Availability: May

    Mitch Pickman Thomas J McCarthy Real Estate

    215 Northfield Ln, Southold, NY 11971
  • /21

    $6,000 Per Month

    • 4 Beds
    • 3 Baths
    • House for Rent

    1155 Old Harbor Rd, Southold, NY 11971

    Quintessential North Fork sandy bay beachfront rental. Stunning views across Cutchogue Harbor and Peconic Bay will be yours at this spacious waterfront home, whether from the airy great room, the brick patio, or from the beachside deck. Tucked away down a quiet drive, this home offers peace and privacy in historic New Suffolk. There are 3 bedrooms and 2 baths upstairs, one bedroom and one bath

    Marianne Collins Brown Harris Stevens N Fork

    1155 Old Harbor Rd, Southold, NY 11971
  • /24

    $8,000 Per Month

    • 3 Beds
    • 3 Baths
    • House for Rent

    355 Midway Rd, Southold, NY 11971

    Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a

    Marianne Collins Brown Harris Stevens N Fork

    355 Midway Rd, Southold, NY 11971
  • /32

    $44,000 Per Month

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

    70 Arshamomaque Ave, Southold, NY 11971

    Southold, North Fork AUGUST 1-14, 2026 Rental: Heaven Off Main. Chic new retreat with ultra vacation vibe. 4 en suite bedrooms, each with a different theme and a full bath, complement the 'public' rooms designed for entertaining. Home opens up to poolside terrace and gorgeous sun! Located in the private bayfront beach community of Beixedon. Book your stay today. Pets on an individual basis.

    Nicholas Planamento William Raveis New York LLC

    70 Arshamomaque Ave, Southold, NY 11971
  • /28

    $9,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • House for Rent

    205 Pine Ave, Southold, NY 11971

    A relaxed North Fork summer retreat with a private beaches, a pool for long afternoons, and easy access to vineyards, farmstands, and waterfront dining. Summer on the North Fork begins at 205 Pine Avenue!Located within the coveted Goose Bay Estates private beach community, this beautifully maintained Southold home offers access to two private beaches at the end of the street—perfect for

    Barbara Poliwoda Douglas Elliman Real Estate

    205 Pine Ave, Southold, NY 11971
  • /31

    $35,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,724 Sq Ft
    • House for Rent

    345 Colonial Rd, Southold, NY 11971

    Tucked away on a private setting in a peaceful North Fork neighborhood just minutes from Corey Creek, Croteaux Vineyards and Greenport Brewery, this exceptional colonial offers the perfect backdrop for an unforgettable summer. With approximately 2,700 sq. ft. of bright, inviting living space across two levels, there is ample room for family and friends to gather and create lasting memories. Step

    Gloria Scrocco STOEBE & CO

    345 Colonial Rd, Southold, NY 11971
  • /17

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 606 Sq Ft
    • House for Rent

    1385 Old Shipyard Ln, Southold, NY 11971

    Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don't miss

    Andrea Parks Douglas Elliman Real Estate

    1385 Old Shipyard Ln, Southold, NY 11971
  • /47

    $20,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft
    • House for Rent

    425 Cedar Point Dr E, Southold, NY 11971

    Now Available for June, July or August 2027. Rented July and August 2026. This Impressive Home is Set Creekfront with Private Dock with Peconic Bay Access and Associated Bay Beach within the Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2

    Rene Giacobbe Douglas Elliman Real Estate

    425 Cedar Point Dr E, Southold, NY 11971
  • /26

    $12,500 Per Month

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

    16125 Soundview Ave, Southold, NY 11971

    Available 2026: September $12,500; October $12,500; November $8,500Experience the very best of the North Fork in this extraordinary soundfront retreat, where miles of pristine Long Island Sound beachfront become your backyard and sunsets RSVP nightly just for you. Wake each morning in the primary suite to panoramic water views that stretch to the horizon, framed by floor-to-ceiling glass that

    Sheri Winter Parker Corcoran

    16125 Soundview Ave, Southold, NY 11971
  • /25

    $6,000 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    400 Diamond Ln, Peconic, NY 11958

    June: $6,000.00 Enjoy stunning water views and all-season access to the Sound from this charming 3-bedroom, 1-bathroom waterfront home. This cozy home channels happy, mid-century vibes. Large living room with fireplace, dining nook, and sunroom, all with breathtaking views of the water. The patio with BBQ is the perfect spot to relax and enjoy the outdoors, and the path to the Sound makes it easy

    Sheri Winter Parker Corcoran

    400 Diamond Ln, Peconic, NY 11958
  • /27

    $19,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    1355 Watersedge Way, Southold, NY 11971

    Welcome to 1355 Watersedge Way, a delightful Bayfront home offering breathtaking water and sunset views in Southold. Nestled next to a nature preserve with 300 feet of private beach, this home provides both serenity and direct water access.Inside, the spacious living room features a a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze. The eat-in

    Jeanmarie Bay William Raveis New York LLC

    1355 Watersedge Way, Southold, NY 11971
  • /47

    $45,000 Per Month

    • 6 Beds
    • 5.5 Baths
    • 6,600 Sq Ft
    • House for Rent

    57305 Route 48, Greenport, NY 11944

    Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

    Zepur Diktas Compass Greater NY LLC

    57305 Route 48, Greenport, NY 11944

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Frequently Asked Questions

How much does it cost to rent a single-family home in Southold, NY?
The median rent for a single-family home in Southold, NY is $10,000 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Southold, NY?
To comfortably afford the median rent in Southold, NY, a household needs to earn roughly $559,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $13,975 per month in Southold, NY, renters typically need to show $41,925 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Southold, NY?
In Southold, NY, the price-to-rent ratio is 5.5, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends in Southold, NY

Rental Home Trends

Number of Houses for Rent
62
Median Single Family Home Rent
$10,000
Median 3 Bedroom Single Family Home Rent
$10,000
Median 4 Bedroom Single Family Home Rent
$16,000
Median 5 Bedroom Single Family Home Rent
$25,000
How to Rent a Home