Southold, NY Homes

• 

  

  

  /9

  $775,000 Pending

  • 1 Bed
  • 4 Baths
  • 2,890 Sq Ft

  Unlisted Address

  Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this

  Andrew Stype Andrew Stype Realty Inc

  Unlisted Address
• 

  

  

  /10

  $3,800 per month

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Apartment for Rent

  775 Hummel Ave Unit A, Southold, NY 11971

  This Freshly Renovated Apartment is centrally located in Southold Village. The Two Family Home is in proximity to everything the North Fork has to offer. Three upstairs Bedrooms are comfortably separated from a large kitchen and entertainment area. The move-in ready apartment is located within Southold School District, and provides for the perfect year round home or North Fork Retreat. Additional

  Joseph Divello Century 21 Albertson Realty

  775 Hummel Ave Unit A, Southold, NY 11971
• 

  $762,000 Sold Sep 12, 2025

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 1,572 Sq Ft
  • Built 1982

  Last Sold Summary

  • 20% Below List Price
  • $485/SF
  • 320 Days On Market

  Current Estimated Value $803,773

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  Unlisted Address
• 

  Est $908,658 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  685 Bay Haven Ln, Southold, NY 11971

  685 Bay Haven Ln, Southold, NY 11971
• 

  

  

  /28

  $899,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft

  920 Pine Neck Rd Unit 2D1, Southold, NY 11971

  Stylishly Renovated Ranch with Saltwater Pool! Bright, white, and move-in ready—this renovated ranch offers the modern coastal look every buyer is searching for. The open, airy layout features a cozy living room, spacious dining area, and an eat-in kitchen with white cabinetry, brushed gold hardware, and new flooring. The living room features large windows overlooking the backyard and gorgeous

  Erica Kelly Daniel Gale Sothebys Intl Rlty

  920 Pine Neck Rd Unit 2D1, 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
• 

  $500,000 Sold Oct 21, 2025

  2555 Youngs Ave Unit 7D, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1987

  Last Sold Summary

  • 13% Below List Price
  • $455/SF
  • 250 Days On Market

  Last Listing Agent Timothy O'Keefe Signature Premier Properties

  2555 Youngs Ave Unit 7D, Southold, NY 11971
• 

  /2

  Est $863,585 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  1430 Bay Haven Ln, Southold, NY 11971

  1430 Bay Haven Ln, Southold, NY 11971
• 

  

  /47

  $1,399,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,226 Sq Ft

  1465 Ackerly Pond Ln, Southold, NY 11971

  Nestled in the heart of Southold’s coveted North Fork, 1465 Ackerly Pond Lane offers a rare opportunity to own a custom home on over 2.5 acres of serene, private land. This single-family property is surrounded by natural beauty and tucked away on a quiet lane, making it ideal for those seeking peace and space just minutes from the village, vineyards, and beaches. Home features a large gourmet

  Scott Bennett Douglas Elliman Real Estate

  1465 Ackerly Pond Ln, Southold, NY 11971
• 

  

  /31

  $25,000 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
• 

  $599,000 Sold May 21, 2025

  45 Smith Dr N, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1959

  Last Sold Summary

  • $666/SF
  • 11 Days On Market

  Current Estimated Value $596,780

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  45 Smith Dr N, Southold, NY 11971
• 

  Est $3,508,333 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,051 Sq Ft

  9502 N Bayview Rd, Southold, NY 11971

  9502 N Bayview Rd, Southold, NY 11971
• 

  

  /46

  $3,825,000

  • 5 Beds
  • 6 Baths
  • 5,285 Sq Ft

  150 Deer Run, Southold, NY 11971

  Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany

  Jeffrey Mead Corcoran

  150 Deer Run, Southold, NY 11971
• 

  

  /40

  $25,000 per month

  • 4 Beds
  • 5.5 Baths
  • 3,855 Sq Ft
  • House for Rent

  525 S Harbor Rd, Southold, NY 11971

  The Ultimate North Fork Retreat! This recently renovated home offers 4 ensuite bedrooms including a ground floor primary suite, with a total of 5.5 baths. The sprawling and very private 2.4 acre property features resort-like amenities including a 20 x 50 heated pool, fully equipped outdoor kitchen, multiple seating areas and more. Inside, the open floor plan flows from the living room with a gas

  Thomas Perry Brown Harris Stevens W Hampton

  525 S Harbor Rd, Southold, NY 11971
• 

  $1,900,000 Sold Mar 18, 2025

  670 Kenneys Rd, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,417 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $786/SF
  • 4 Days On Market

  Current Estimated Value $1,822,731

  Last Listing Agent Robert Merolla Aurora Property Group

  670 Kenneys Rd, Southold, NY 11971
• 

  Est $901,432 Not Listed For Sale

  • 2 Beds
  • 1 Bath

  580 Jacobs Ln, Southold, NY 11971

  580 Jacobs Ln, Southold, NY 11971
• 

  

  /5

  $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
• 

  

  /16

  $35,000 per month

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

  3693 Pine Neck Rd, Southold, NY 11971

  Elegant Waterfront Retreat on the North Fork - Welcome guests in style at this exquisite waterfront residence, where timeless design meets relaxed coastal living. Overlooking serene, protected waters, this expansive home features a sparkling waterside pool, private dock, and inviting fire pit—creating an idyllic setting for summer entertaining.Thoughtfully designed living and gathering spaces

  Eric Frend Corcoran

  3693 Pine Neck Rd, Southold, NY 11971
• 

  $975,000 Sold Aug 28, 2025

  6815 Soundview Ave, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1938

  Last Sold Summary

  • 3% Above List Price
  • $812/SF
  • 9 Days On Market

  Current Estimated Value $1,042,216

  Last Listing Agent Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  6815 Soundview Ave, Southold, NY 11971
• 

  Est $1,776,333 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  425 Jacobs Ln, Southold, NY 11971

  425 Jacobs Ln, Southold, NY 11971
• 

  

  /23

  $725,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  340 Pine Rd, Southold, NY 11971

  Southold- Get ready to kick off your shoes this summer... Kenneys Beach is waiting for you. This two bedroom, one bath ranch home has been lovingly maintained. An easy, open floor plan consists of a living room, eat-in-kitchen, and separate dining room/den. Slider to a large patio perfect for entertaining and family get-togethers. Two comfortable bedrooms. One bath with a tub/shower combo. Wood

  Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  340 Pine Rd, Southold, NY 11971
• 

  

  /27

  $10,000 per month

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

  275 Maier Place, Southold, NY 11971

  Seasonal Rental in Scenic Southold, NY – 3 Bed, 3 Bath RetreatEscape to the heart of the North Fork with this beautifully appointed 3-bedroom, 2-bath seasonal rental in picturesque Southold, NY. Nestled among the region's famed vineyards, farm stands, and white sand beaches, this home offers the perfect blend of charm, comfort, and convenience.Inside, you'll find a spacious and

  Mary Terry MCKENNASHEA LLC

  275 Maier Place, Southold, NY 11971
• 

  $1,730,000 Sold Nov 12, 2025

  20845 Soundview Ave, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1951

  Last Sold Summary

  • 4% Below List Price
  • $1,229/SF
  • 39 Days On Market

  Last Listing Agent Stephanie Ranghelli Realty Connect USA LI Inc

  20845 Soundview Ave, Southold, NY 11971
• 

  Est $1,209,172 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths

  1715 Minnehaha Blvd, Southold, NY 11971

  1715 Minnehaha Blvd, Southold, NY 11971
• 

  

  /50

  $1,350,000

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft

  2055 Boisseau Ave, Southold, NY 11971

  Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a

  Nicholas Planamento William Raveis New York LLC

  2055 Boisseau Ave, Southold, NY 11971
• 

  

  /20

  $5,000 per month

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

  145 Founders Path, Southold, NY 11971

  Beautiful Charming Cottage Located in the Coveted Community of Founders. Close to a gorgeous sandy beach, grocery shopping, coffee shop, restaurants, jitney stop, and all things North Fork. Three bedrooms, one bath, LR, kitchen, outdoor deck, fire pit, outdoor shower. Available Sept. $5000, Oct & Nov $4000, Dec through March $3,000, April $3,500. May $5,000, June $6,000 and August $12,000.

  Diane Mollica Compass Greater NY LLC

  145 Founders Path, Southold, NY 11971
• 

  $2,700,000 Sold Sep 25, 2025

  54985 Middle Rd, Southold, NY 11971

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft
  • Built 2010

  Last Sold Summary

  • 16% Below List Price
  • $771/SF
  • 133 Days On Market

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  54985 Middle Rd, Southold, NY 11971
• 

  Est $3,590,333 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,300 Sq Ft

  1480 Old Wood Path, Southold, NY 11971

  1480 Old Wood Path, Southold, NY 11971
• 

  

  /39

  $1,200,000

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft

  3475 Oaklawn Ave, Southold, NY 11971

  Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence

  Trish Bergin Signature Premier Properties

  3475 Oaklawn Ave, 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
• 

  $685,000 Sold Nov 18, 2025

  2555 Youngs Ave Unit 14A, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $571/SF
  • 12 Days On Market

  Last Listing Agent Diane Mollica Compass Greater NY LLC

  2555 Youngs Ave Unit 14A, Southold, NY 11971
• 

  Est $2,827,275 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  100 W Shore Dr, Southold, NY 11971

  100 W Shore Dr, Southold, NY 11971
• 

  

  /34

  $2,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,238 Sq Ft

  1665 Glenn Rd, Southold, NY 11971

  Southold-West Creek Estates - Beautifully appointed, light-filled home. Recently completed with attention to every detail. A wood and glass front door and natural wood architectural accents set the tone at the front entrance. The large great room features a living area with a two-sided gas fireplace, dining area, and a generous chefs eat-in kitchen. The second side of the fireplace faces the

  Barry Novick Daniel Gale Sothebys Intl Rlty

  1665 Glenn Rd, 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
• 

  $370,000 Sold May 23, 2025

  55075 Route 25 Unit 1, Southold, NY 11971

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $370/SF
  • 28 Days On Market

  Current Estimated Value $337,000

  Last Listing Agent Kenneth Poliwoda Douglas Elliman Real Estate

  55075 Route 25 Unit 1, Southold, NY 11971
• 

  Est $3,180,333 Not Listed For Sale

  • 4 Beds
  • 4 Baths

  150 W Shore Dr, Southold, NY 11971

  150 W Shore Dr, Southold, NY 11971
• 

  

  /15

  $749,000

  • 2 Beds
  • 1 Bath
  • 1,114 Sq Ft

  265 Hummel Ave, Southold, NY 11971

  Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives

  Amanda Lin Douglas Elliman Real Estate

  265 Hummel Ave, Southold, NY 11971
• 

  

  /25

  $50,000 per month

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

  1160 Goose Creek Ln, Southold, NY 11971

  Available: July $50,000; Aug - LD: $55,000; July/Aug-LD $85,000Step back in time-without sacrificing comfort-in this beautifully preserved 5-bedroom, 3-bath home brimming with charm and nestled along the tranquil banks of Goose Creek. Surrounded by water on two sides and set on a private road, this unique property offers a rare blend of historic character and modern amenities. From the moment

  Sheri Winter Parker Corcoran

  1160 Goose Creek Ln, Southold, NY 11971
• 

  $1,940,000 Sold Feb 15, 2025

  650 Old Harbor Rd, Southold, NY 11971

  • 2 Beds
  • 3 Baths
  • 2,025 Sq Ft
  • Built 1971

  Last Sold Summary

  • 8% Above List Price
  • $958/SF
  • 27 Days On Market

  Current Estimated Value $1,929,842

  Last Listing Agent Bridget Elkin Compass Greater NY LLC

  650 Old Harbor Rd, Southold, NY 11971
• 

  Est $1,447,656 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,492 Sq Ft

  295 Grove Dr, Southold, NY 11971

  295 Grove Dr, Southold, NY 11971

Showing Results 81 - 120, Page 3 of 18