$999,999
- 2 Beds
- 1 Bath
- 1,954 Sq Ft
600 Highwood Rd, Southold, NY 11971
Alexis Meadows Compass Greater NY LLC
$999,999
600 Highwood Rd, Southold, NY 11971
Alexis Meadows Compass Greater NY LLC
$12,500 Per Month
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
$1,130,000
70 Mockingbird Ln, Southold, NY 11971
Last Sold Summary
Current Estimated Value $1,110,074
Last Listing Agent Kelly Gatanas Daniel Gale Sothebys Intl Rlty
70 Mockingbird Ln, Southold, NY 11971
Est $1,315,704
295 Grove Dr, Southold, NY 11971
Last Sold Summary
$1,699,000
1700 Smith Dr S, Southold, NY 11971
Kristy Naddell Douglas Elliman Real Estate
$16,000 Per Month
2380 S Harbor Rd, Southold, NY 11971
Available: July $16K, August $19.5K, Oct 1, 2026 to Sept 30, 2027 - Monthly Rate $3,700. The Yellow House sits on five secluded acres in Southold on the North Fork of Long Island, offering sweeping vineyard views and stunning sunsets. One of the North Fork's best bay beaches is just a five-minute stroll to the end of the road. The home has been newly painted and furnished and features central air
Sheri Winter Parker Corcoran
$1,943,000
630 Tarpon Dr, Southold, NY 11971
Last Sold Summary
Current Estimated Value $1,678,999
Last Listing Agent Tom Uhlinger Douglas Elliman Real Estate
630 Tarpon Dr, Southold, NY 11971
Est $973,813
950 Paradise Shores Rd, Southold, NY 11971
Last Sold Summary
$1,295,000
1220 Youngs Ave, Southold, NY 11971
Lee Beninati Beninati Associates
$19,500 Per Month
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
$1,500,000
3635 Old North Rd, Southold, NY 11971
Last Sold Summary
Current Estimated Value $1,485,626
Last Listing Agent Kristy Naddell Douglas Elliman Real Estate
3635 Old North Rd, Southold, NY 11971
Est $1,376,312
2230 Paradise Shores Rd, Southold, NY 11971
Last Sold Summary
$975,000
445 Budds Pond Rd, Southold, NY 11971
Bridget Elkin Compass Greater NY LLC
$10,000 Per Month
1050 Pine Ave, Southold, NY 11971
North Fork summers are defined by sun-soaked beach days, vineyard hopping, and slow evenings spent cooking under the open sky—and this charming 3-bedroom, 2-bath cottage captures it all. Tucked away in Southold, this inviting rental places you right in the heart of the North Fork, perfectly positioned to experience everything the area has to offer. Spend your mornings browsing Southold’s curated
Kieran Collings Douglas Elliman Real Estate
$785,000
6980 N Bayview Rd, Southold, NY 11971
Last Sold Summary
Current Estimated Value $832,377
Last Listing Agent Nicholas Planamento William Raveis New York LLC
6980 N Bayview Rd, Southold, NY 11971
Est $1,779,594
9390 N Bayview Rd, Southold, NY 11971
Last Sold Summary
$1,799,000
420 Leon Rd, Southold, NY 11971
420 Leon Rd, Southold, NY 11971$6,800 Per Month
51970 New York 25, Southold, NY 11971
Pack your bags and relax this summer in this beautifully renovated farmhouse in the heart of the North Fork! Enjoy a delightful retreat in this irresistible and stylishly appointed cottage with charm and comfort throughout! The recently updated eat-in kitchen features brand new stainless steel appliances, and all of the rooms throughout are fresh clean awaiting your arrival. This home is right in
Suzette Reiss Douglas Elliman Real Estate
$650,000
900 Cedar Dr, Southold, NY 11971
Last Sold Summary
Current Estimated Value $671,449
Last Listing Agent Lisa Cerreta BERKSHIRE HATHAWAY
900 Cedar Dr, Southold, NY 11971
Est $1,226,965
670 Seawood Dr, Southold, NY 11971
Last Sold Summary
$4,300,000
11535 N Bayview Rd, Southold, NY 11971
11535 N Bayview Rd, Southold, NY 11971$20,000 Per Month
950 Blue Marlin Dr, Southold, NY 11971
Beachfront, located in Southold Shores, this architect's own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite,
Lori Feilen William Raveis New York LLC
$2,600,000
1635 Laurel Ave, Southold, NY 11971
Last Sold Summary
Last Listing Agent Kristy Naddell Douglas Elliman Real Estate
1635 Laurel Ave, Southold, NY 11971
Est $906,073
1750 Seawood Dr, Southold, NY 11971
Last Sold Summary
$2,495,000
1455 Cedar Point Dr E, Southold, NY 11971
Maureen Sullivan Daniel Gale Sothebys Intl Rlty
$14,950 Per Month
100 W Shore Dr, Southold, NY 11971
Set in the highly sought-after Reydon Shores community, 100 W Shore Dr, Southold is a rare dog-friendly North Fork waterfront seasonal rental with your own private, sandy beach and sweeping bay views to Shelter Island. This renovated classic offers three levels of living with a great room and sunroom, 6 bedrooms, 3.5 baths, two wood-burning fireplaces, and a huge Trex deck built for sunset
Basil Boziotis Compass Greater NY LLC
$665,000
205 Grange Rd, Southold, NY 11971
Last Sold Summary
Current Estimated Value $688,371
Last Listing Agent Rita Rooney Douglas Elliman Real Estate
205 Grange Rd, Southold, NY 11971
Est $813,084
1785 Seawood Dr, Southold, NY 11971
Last Sold Summary
$1,699,000
530 Sunset Way, Southold, NY 11971
Thomas McCarthy Thomas J McCarthy Real Estate
$25,000 Per Month
910 Glenn Rd, Southold, NY 11971
Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car
Andrea Parks Douglas Elliman Real Estate
$890,000
4100 Youngs Ave, Southold, NY 11971
Last Sold Summary
Current Estimated Value $925,673
Last Listing Agent Jeannine Kowaleski William Raveis New York LLC
4100 Youngs Ave, Southold, NY 11971
Est $1,034,580
605 Topsail Ln, Southold, NY 11971
Last Sold Summary
$500,000
265 Arshamomaque Ave, Southold, NY 11971
265 Arshamomaque Ave, Southold, NY 11971$30,000 Per Month
650 Pine Ave, Southold, NY 11971
Masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.
Colin McCarthy Thomas J McCarthy Real Estate
$1,175,000
1475 Oaklawn Ave, Southold, NY 11971
Last Sold Summary
Current Estimated Value $1,154,396
Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty
1475 Oaklawn Ave, Southold, NY 11971
Est $1,344,402
1525 Leeward Dr, Southold, NY 11971
Last Sold Summary
$4,000,000
1480 Old Wood Path, Southold, NY 11971
Bridget Elkin Compass Greater NY LLC
$7,000 Per Month
Unlisted Address
Experience the charm of this delightful rental cottage nestled in Southold, North Fork, just a stone’s throw from Founder's Landing Park and Wharf House, with one of the most amazing sugar sand beaches in our community. This unique, fully furnished one-bedroom retreat features flexible rental periods and competitive rates throughout the year.Imagine waking up to the serene views of a
Nicholas Planamento William Raveis New York LLC
$1,150,000
2865 S Harbor Rd, Southold, NY 11971
Last Sold Summary
Current Estimated Value $1,185,496
Last Listing Agent Shane Hafer Compass Greater NY LLC
2865 S Harbor Rd, Southold, NY 11971
Est $3,757,000
10995 N Bayview Rd, Southold, NY 11971
Last Sold Summary
Showing Results 161 - 200, Page 5 of 18