Southold, NY Homes

/26
$527,500
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
2555 Youngs Ave Unit 11D, Southold, NY 11971

Welcome to Founders Village in Southold. This quiet and quaint 55+ community is located in the heart of Southold Town. This 2 bed 2 bath condo is ready for you to make it home. Just minutes away to Jitney, train station, shopping, groceries, retail, dining, post office, gym and so much more. Either enjoy the beautiful common grounds with the community pool & club house in a quaint setting, or

Patrick Carpenter Signature Premier Properties

2555 Youngs Ave Unit 11D, Southold, NY 11971
/25
$3,500 per month
- 3 Beds
- 1 Bath
- House for Rent
400 Diamond Ln, Peconic, NY 11958

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 to access the

Sheri Winter Parker Corcoran

400 Diamond Ln, Peconic, NY 11958
$515,000 Sold Dec 18, 2024
- 1,200 Sq Ft
- $429/SF
- 74 Days On Market
- 2 Beds
- 2 Baths
- Built 1986
2555 Youngs Ave Unit 16C, Southold, NY 11971

.Take advantage of this newly adjusted price on a spacious 2-bedroom, 2-full bath condo in the highly sought-after Founders Village 55+ community. Offering the perfect blend of comfort and convenience, this home is just minutes from town and all its amenities. The washer and dryer are conveniently located on the first floor for easy living. Enjoy the community pool or relax in the peaceful

Katie DiGregorio Corcoran

2555 Youngs Ave Unit 16C, Southold, NY 11971

Est $1,380,353 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,020 Sq Ft
2305 Glenn Rd, Southold, NY 11971

2305 Glenn Rd, Southold, NY 11971

/7
$1,700,000
- Land
- 5 Acres
- $323,810 per Acre
11200 N Bayview Rd, Southold, NY 11971

Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an equestrian grazing meadow to an adjoining 33 acre estate, this land offers a scenic, tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land.Just a few miles to fine dining and cafes, tasting rooms & vineyards,

Kathleen Travers Douglas Elliman Real Estate

11200 N Bayview Rd, Southold, NY 11971
/21
$70,000 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
$860,000 Sold Dec 11, 2024
- 1,720 Sq Ft
- $500/SF
- 93 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
810 Greenfields Ln, Southold, NY 11971

Discover tranquility and convenience in this inviting 3-bedroom, move-in ready home nestled on a shy acre in a private, quiet neighborhood. Located just moments from the village and pristine beaches, this property offers the perfect blend of privacy and accessibility. Step inside to find a meticulously maintained interior boasting ample natural light and a cozy atmosphere. The spacious living

Erin Kaelin Signature Premier Properties

810 Greenfields Ln, Southold, NY 11971

Est $1,216,732 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,200 Sq Ft
480 Grissom Ln, Southold, NY 11971

480 Grissom Ln, Southold, NY 11971

/29
$999,000
- 4 Beds
- 3 Baths
- 2,000 Sq Ft
9875 Main Bayview Rd, Southold, NY 11971

Amazing opportunity to own a charming 1830s home with a detached accessory apartment built in 2016. Renovated in 2003, this home sits on an acre of land surrounded by unbuildable land, offering privacy and a peaceful setting. With great bones and timeless appeal, the main house features a well-designed floor plan, a cozy living room with a wood-burning fireplace, and plenty of character

Kristy Naddell Douglas Elliman Real Estate

9875 Main Bayview Rd, Southold, NY 11971
/23
$6,000 per month
- 3 Beds
- 2 Baths
- House for Rent
600 Corey Creek Ln, Southold, NY 11971

Chic ranch at 600 Corey Creek Lane, Southold. Featuring a beautiful wood-burning fireplace centered in the living room with high vaulted ceilings. 3 beds and 2 baths complete this home with an updated kitchen flowing into the dining area. Outside is a generous-sized patio with a firepit perfect for unwinding and having a relaxing night. Great location; close to town with shops and restaurants

Lori Feilen William Raveis New York LLC

600 Corey Creek Ln, Southold, NY 11971
$831,000 Sold Dec 10, 2024
- 1,200 Sq Ft
- $692/SF
- 12 Days On Market
- 3 Beds
- 1 Bath
- Built 1940
145 Founders Path, Southold, NY 11971

Location, location! Founders Landing community! Enjoy all the North Fork has to offer with this beautiful three bedroom, one bath cottage. Centrally located and a stone's throw away from the Jitney, LIRR, quaint coffee shops, restaurants and beach, this prime location offers convenience as well as privacy. After a fun summer beach day, take advantage of the outdoor shower and spend the evenings

Connie Liappas Compass Greater NY LLC

145 Founders Path, Southold, NY 11971

Est $965,919 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
2230 Cedar Dr, Southold, NY 11971

2230 Cedar Dr, Southold, NY 11971

/26
$849,000
- 2 Beds
- 2 Baths
- 1,300 Sq Ft
150 Hobart Rd, Southold, NY 11971

Experience the ultimate North Fork retreat in Southold—this stunning, turnkey cottage is a true embodiment of coastal living! Ideally situated near Founder’s Landing Park with effortless beach access and close to the Wharf House, this charming cedar-shake farmhouse is designed for entertaining and showcases an unrivaled in-town location where a car is simply unnecessary. Take advantage of

Nicholas Planamento William Raveis New York LLC

150 Hobart Rd, Southold, NY 11971
/32
$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 smart TV and a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze.

Jeanmarie Bay William Raveis New York LLC

1355 Watersedge Way, Southold, NY 11971
$1,520,000 Sold Dec 06, 2024
- 3,000 Sq Ft
- $507/SF
- 53 Days On Market
- 4 Beds
- 2 Baths
- Built 1965
775 Hill Rd, Southold, NY 11971

RARE OPPORTUNITY to own with 100ft of Bulkhead on Jockey Creek. Sitting on .5 acre with room for a POOL, this 4 bed and 2 bath has tons of potential waiting to be unlocked, while being fully operational and ready to enjoy Day 1. House has updated FORCED AIR heating system and has CENTRAL AC as well! Large bedrooms/common rooms and kitchen all with high ceilings, and an incredible Full Unfinished

Bryce Levy Daniel Gale Sothebys Intl Rlty

775 Hill Rd, Southold, NY 11971

Est $611,767 Not Listed For Sale
- 2 Beds
- 1.5 Baths
375 Oak Ave, Southold, NY 11971

375 Oak Ave, Southold, NY 11971

/4
$799,000
- Land
- 2.29 Acres
- $348,908 per Acre
1350 Hortons Ln, Southold, NY 11971

Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot, Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life, You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom

Thomas McCarthy Thomas J McCarthy Real Estate

1350 Hortons Ln, Southold, NY 11971
/25
$7,500 per month
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
3400 Youngs Ave, Southold, NY 11971

Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farmfield. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at One

Thomas McCarthy Thomas J McCarthy Real Estate

3400 Youngs Ave, Southold, NY 11971
$815,000 Sold Dec 06, 2024
- 27 Days On Market
- 3 Beds
- 2 Baths
- Built 1959
685 Bay Haven Ln, Southold, NY 11971

This lovely well cared for home near stunning water views allows you to enjoy all the magnificence of Long Island's East End. The home offers an entry foyer, a sun filled living room, a formal dining room, an eat-in-kitchen, 3 bedrooms, 2 baths, and a large garage, all well situated on a beautiful lush property just feet from the beach., Additional information: Appearance:Excellent,Separate

Eleanor Dunne Andron Realty Group Tulip R E

685 Bay Haven Ln, Southold, NY 11971

Est $796,539 Not Listed For Sale
- 2 Beds
- 1 Bath
980 Oak Ave, Southold, NY 11971

980 Oak Ave, Southold, NY 11971

/6
$4,495,000
- Land
50100 County Road 48, Southold, NY 11971

Attention Developers and Discerning Investors! Opportunity knocks with this 36-acre parcel, Development Rights in Tact, nestled in the heart of the North Fork. Ideally positioned along Arshamomack Creek with access to both County and Municipal roadways, this property offers a perfect setting for the development of either workforce housing, an exclusive residential enclave or a private estate. A

Lisa Gillooly Compass

50100 County Road 48, Southold, NY 11971
/29
$10,500 per month
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
- House for Rent
250 Wesland Rd, Southold, NY 11971

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

Marie Beninati Beninati Associates

250 Wesland Rd, Southold, NY 11971
$465,000 Sold Dec 03, 2024
- Land
- 0.42 Acre
- $1,107,143 per Acre
- 20 Days On Market
295 Grange Rd, Southold, NY 11971

Don't miss your opportunity to build your very own custom home in Southold. Located on the south side in the Bayview section just minutes from town, vineyards and Greenport Brewery. This parcel being offered is level throughout and mostly wooded on a quiet dead end street ways away from any noise or water disturbance. There is 100 feet fronting Grange Rd and 160 feet deep and the zoning on this

Thomas Panebianco Realty Connect USA L I Inc

295 Grange Rd, Southold, NY 11971

Est $1,101,760 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
1145 Smith Dr S, Southold, NY 11971

1145 Smith Dr S, Southold, NY 11971

/16
$999,999 Open Sun 11AM - 1PM
- 5 Beds
- 2 Baths
- 1,500 Sq Ft
65 Lake Dr, Southold, NY 11971

The Perfect Beach Bungalow Getaway! An Idyllic Location, With Kenney's Beach Practically At Your Doorstep, This Charming Bungalow Offers Ample Space For Everyone With Five Bedrooms And Two Bathrooms. Relax And Unwind On The Outside Decks Enjoying Morning Coffee, Fresh Sea Breezes And Evening Sunsets Or Warm-up Indoors by the Fireplace. With Its Wonderful Location, Numerous Amenities And

Thomas McCarthy Thomas J McCarthy Real Estate

65 Lake Dr, Southold, NY 11971
/30
$15,000 per month
- 4 Beds
- 2 Baths
- House for Rent
3675 Wells Ave, Southold, NY 11971

Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek

Kristen Rishe Signature Premier Properties

3675 Wells Ave, Southold, NY 11971
$3,149,000 Sold Nov 27, 2024
- 4,400 Sq Ft
- $716/SF
- 192 Days On Market
- 4 Beds
- 5.5 Baths
- Built 2023
630 Calves Neck Rd, Southold, NY 11971

Welcome to 630 Calves Neck Road! This new construction North Fork diamond boasts 4,400 square feet of luxury with 4 en-suite bedrooms, 5.5 baths and a huge bonus room with skylights. Set on .75 acres and offering seamless architectural details, the meticulous craftsmanship is evident in a gorgeous EIK with center island, high end finishes including Wolf and Sub-zero appliances, marble and

Connie Liappas Compass Greater NY LLC

630 Calves Neck Rd, Southold, NY 11971

Est $1,199,083 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,400 Sq Ft
305 Smith Dr S, Southold, NY 11971

305 Smith Dr S, Southold, NY 11971

/8
$690,000
- 3 Baths
- 1,860 Sq Ft
Unlisted Address

1-1/2 story medical office, with reception area, offices, exam rooms, 1 full bathroom, 2 half bathrooms, supply room, attic storage, 80% full, unfinished basement w/6-1/2 ft ceiling and outside entrance, 20 crawl space. Detached garage. Great location. Area is mixed use with single family residential homes, offices and light business. Zoned Residential/Office - Currently used as a medical

Andrew Stype Andrew Stype Realty Inc

Unlisted Address
/34
$30,000 per month
- 8 Beds
- 7 Baths
- 5,400 Sq Ft
- House for Rent
650 Pine Ave, Southold, NY 11971

Permit 816. Beautiful New Construction In Private Beach Community. Creekfront Beach Access Along With 20x40 Heated Saltwater Pool. Ideal For Large Groups & Perfect For Entertaining, This Property Has It All. 8 Bedrooms And 7 Bathrooms Set On Lush Manicured Grounds, Provides Spacious Accommodations For Up To 16 Guests. Spend Afternoons Lounging By The Pool & Evenings Gathering With Family And

Colin McCarthy Thomas J McCarthy Real Estate

650 Pine Ave, Southold, NY 11971
$1,325,000 Sold Nov 22, 2024
- 2,971 Sq Ft
- $446/SF
- 47 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1910
3295 Pine Neck Rd, Southold, NY 11971

SOUTHOLD WATERFRON - Step back in time and connect with nature at the historic Allen Tobey Carriage House. Constructed in 1910, this charming residence was relocated to the verdant expanse of Jockey Estates in the 1950s, becoming a part of the "Red Road" community. Today, the house is nestled within private, mature grounds, featuring 300-year-old trees. The expansive lawn rolls down to a creek,

Linda Statam William Raveis New York LLC

3295 Pine Neck Rd, Southold, NY 11971

Est $691,210 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
305 Bayberry Rd, Southold, NY 11971

305 Bayberry Rd, Southold, NY 11971

/35
$2,399,000
- 6 Beds
- 5.5 Baths
- 3,630 Sq Ft
47100 Route 25, Southold, NY 11971

The Beautiful Gunite Pool with Spa Features and Beach Rights to the lovely South Harbor Beach, add to the allure of this stunning, North Fork Farmhouse, cleverly Re-imagined and Restored in 2023! Start your tour as you step across the expansive covered Front Porch and enter the Elegant Entry Hall featuring wonderfully Preserved, Decorative Wood Floors. As you pass through the hall, you'll

Deborah Kusa Douglas Elliman Real Estate

47100 Route 25, 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: May $5000, June $7000, October $4500,

Kenneth Poliwoda Douglas Elliman Real Estate

3825 S Harbor Rd, Southold, NY 11971
$1,268,000 Sold Nov 22, 2024
- 2,492 Sq Ft
- $509/SF
- 38 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1945
295 Grove Dr, Southold, NY 11971

Southold--Reydon Shores--Beautiful, charming, farmhouse invites you in. 3-bedroom, 2.5 bath home in sought after community of Reydon Shores with easy access to the Association Bay beach and Marina. First floor large primary en-suite bedroom, chef's kitchen with top shelf stainless appliances including a Thermador cooktop and double oven. Radiant heat in Primary Bath and Kitchen. Closets beyond

Nancy Cervelli Daniel Gale Sothebys Intl Rlty

295 Grove Dr, Southold, NY 11971

Est $1,049,135 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
855 Grange Rd, Southold, NY 11971

855 Grange Rd, Southold, NY 11971

/27
$9,275,000
- 5 Beds
- 4.5 Baths
- 4,627 Sq Ft
1750 Hobart Rd, Southold, NY 11971

Welcome to a stunning, one-of-a-kind waterfront home in the highly sought-after hamlet of Southold. This custom, new construction, modern residence is perfectly situated on Town Creek, featuring 160 feet of waterfront and expansive views of Peconic Bay. It includes a private 6' x 20' floating dock connected by an 82' Trex catwalk. Constructed with meticulous attention to detail, this home is

Alexis Meadows Douglas Elliman Real Estate

1750 Hobart Rd, Southold, NY 11971
/22
$20,000 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
$1,050,000 Sold Nov 22, 2024
- 3,000 Sq Ft
- $350/SF
- 103 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1975
345 Colonial Rd, Southold, NY 11971

REYDON HEIGHTS GEM! Expertly finished space for premier living, entertaining and enjoyment - inside and outside! In the summer, enjoy all the fun and activities outdoors in a private, enclosed backyard complete with an oversized, freeform, in-ground pool, hot tub, outdoor kitchen and plenty of chaise lounges and comfy chairs to enjoy the lazy days of summer! Inside the home's modern open flair

Lee Beninati Beninati Associates

345 Colonial Rd, Southold, NY 11971

Est $925,583 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
46660 Route 25, Southold, NY 11971

46660 Route 25, Southold, NY 11971

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