SOUTHOLD, NY HOMES FOR SALE


Southold

Southold, which was established 1640, has long been a delightful community and continues to evolve with its unspoiled beaches, sprawling vineyards and wineries, agricultural production and farm stands, historic buildings, museums and unlimited recreational opportunities. Its bucolic qualities, culture and history have made Southold a special place to be, and continues to thrive with its unique shopping opportunities and casual and fine dining fare.

Southold

Total Listings: 127
Average Price: $914,457
Highest Price: $8,800,000
Lowest Price: $99,000

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EXPLORE SOUTHOLD

 

Southold Homes For Sale

127 Properties Found. Page 1 of 3
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Brick Cove Was Originally A Brickyard Built In ...

$8,800,000

1760 Sage Blvd, Southold

  • 4 Beds
  • 2 Baths
  • 11.83 Acres
  • 1,500 sqft

School District: Greenport

Brick Cove Was Originally A Brickyard Built In 1887. Today, It Is Home To A Thriving Marina With 138 Slips And A Single-family Residence. Other Buildings On The Property Include Workshops, A Steel Barn, An Office/marina Store, Pool House And Sheds. Guests C...

This Magical Waterfront Homestead Encompasses O...

$6,750,000

Southold

  • 5 Beds
  • 6 Baths
  • 5.23 Acres
  • 4,565 sqft

School District: Southold

This Magical Waterfront Homestead Encompasses Over 5 Acres, 421 Ft Of Water W. A Dock And Channels Vacation Vibes. 5+ Brs, 5.5 Bas, Grand Eik W/ Fpl, Encl. Porch, Sun-room, Lr W. A Fpl And A Partially Fin Basement. Step Outside And Experience The Magic W/a ...

Southold Bayfront - Bright 5 Br, 4.5 Ba Contemp...

$2,300,000 Under Contract

495 North Parish Dr, Southold

  • 5 Beds
  • 5 Baths
  • 0.8 Acres
  • 3,675 sqft

School District: Southold

Southold Bayfront - Bright 5 Br, 4.5 Ba Contemporary. Spacious Open Floor Plan For Family Gatherings And Entertaining. Great Room With Vaulted Ceiling Leads To Four Season Waterside Porch With Sweeping Water Views Over Southold Bay To Shelter Island. Four ...

This Home Is Made For Entertaining! 5500 Sf And...

REDUCED 10%

$2,250,000

21075 Soundview Ave, Southold

  • 5 Beds
  • 6 Baths
  • 0.8 Acres
  • 5,544 sqft

School District: Southold

This Home Is Made For Entertaining! 5500 Sf And 100' Of Sound Front With Incredible Views And Spectacular Sunsets. The Main House Features 5 Br Including Master Suite With Office, 6 Ba, A Loft And A Full Finished Basement Including A Bathroom With A Steam S...

Spacious Center Hall Colonial On Goose Creek W/...

REDUCED 9%

$1,999,999

105 Waterview Dr, Southold

  • 4 Beds
  • 4 Baths
  • 4 Acres
  • 5,000 sqft

School District: Southold

Spacious Center Hall Colonial On Goose Creek W/ Private Dock. Gated Custom-built Waterfront Estate W/ Attention To Every Detail. 52' X 50' Deck Ready For Pool Insert. Premium Oak Floors, Sauna, Radiant Floor Heat, Designer Lighting & Gourmet Kitchen W/ Glob...

Diamond In The Rough! A Rare Paradise Point Ba...

$1,899,000

450/520 Basin Rd, Southold

  • 4 Beds
  • 2 Baths
  • 2,100 sqft

School District: Southold

Diamond In The Rough! A Rare Paradise Point Bayfront Opportunity In A Stunning Location That Offers Spectacular Views Of Southold Bay, Shelter Island And Breathtaking Sunsets. 175' On The Water, Wooded, Private And An Association Marina Basin Just Steps A...

Southold, North Fork: Authentic Barn House On ...

REDUCED 5%

$1,895,000

1395 Sleepy Hollow Ln, Southold

  • 4 Beds
  • 5 Baths
  • 1.08 Acres
  • 4,500 sqft

School District: Southold

Southold, North Fork: Authentic Barn House On Goose Creek Waterfront. Private Setting. Sublime Views. Flexible Floorplan Lends Itself To Owner Occupied B&b (w/town Permit Req'd). Large, Open Rooms Include Vaulted Ceiling In The Main Living Spaces And L...

Its All About Location! Stunning Views From Thi...

$1,875,000

695 N Parish Dr, Southold

  • 4 Beds
  • 3 Baths
  • 0.53 Acres

School District: Southold

Its All About Location! Stunning Views From This Southold Bayfront Ranch Home With Walk Out Lower Level. Rare Opportunity To Own A Home Directly On Southold Bay Near Goose Creek. Open Floor Plan. Gorgeous View From Living Room, Dining Room, And Master Bedro...

28 Acres On North Bayview. Development Rights E...

REDUCED 22% Photo of Listing #2965814

$1,800,000

8360 N Bayview Rd, Southold

  • 28 Acres

School District: Southold

28 Acres On North Bayview. Development Rights Entact. Possible Sub-division With Approval. All Or Part Of Development Rights May Be Sold To A Variety Of Local Municipalities. Development Potential : Possible Use As An Estate, Horse Farm. Agricultural Friend...

Cape Cod Waterfront Located On One Of Southold'...

$1,800,000

1515 Calves Neck Rd, Southold

  • 2 Beds
  • 2 Baths
  • 0.58 Acres
  • 2,350 sqft

School District: Southold

Cape Cod Waterfront Located On One Of Southold's Most Coveted Streets, Combines The Best Of Elegance, Style, & Craftsmanship. Vaulted Ceilings, 2 Wb Frplcs & A Long Stretch Of Windows W/ Spectacular Views Of Town Creek & Southold Bay Connect The Open Chef's...

Come See This One Of A Kind Sprawling Beach Hou...

REDUCED 4%

$1,775,000

9326 Main Bayview Rd, Southold

  • 5 Beds
  • 6 Baths
  • 3.62 Acres
  • 4,500 sqft

School District: Southold

Come See This One Of A Kind Sprawling Beach House Situated On 3.5+acres Of Waterfront Privacy, Elevator, 5+br, 5.5ba.,gunite Heated Pool. Stunning Waterfront Views From Every Room, Creek To Bay Access. This Is A Fantastic Buy

Unique Waterfront Property On It's Own Private ...

REDUCED 3%

$1,700,000

2850 Cedar Beach Rd, Southold

  • 3 Beds
  • 1 Baths
  • 2.91 Acres
  • 1,856 sqft

School District: Southold

Unique Waterfront Property On It's Own Private Peninsula Includes 2 Rare Single & Separate Creek Front Lots. Reno The House/finish The Barn And Enjoy Stunning Views Of Peconic Bay. An Ideal Family Compound In A Pastoral Setting. The Dock Can Accommodate A...

Welcome To This Impeccably Maintained Post Mode...

REDUCED 4%

$1,700,000

1380 Oakwood Dr, Southold

  • 4 Beds
  • 5 Baths
  • 0.7 Acres
  • 3,800 sqft

School District: Southold

Welcome To This Impeccably Maintained Post Modern Home. With Over 3800 Sq.ft. Of Living Space And 92' Water Front W/dock & Direct Bay Access.this Home Expemplifies Pride In Ownership. Contained Within Are 4 Brs, 4.5 Baths Including 2 Master Suites, Office, ...

Spacious 3bd Waterfront Home In Calves Neck Are...

$1,699,000

1175 W Hill Rd, Southold

  • 3 Beds
  • 3 Baths
  • 1.15 Acres
  • 2,100 sqft

School District: Southold

Spacious 3bd Waterfront Home In Calves Neck Area Of Southold. 30' Of Bulkheading & Dock (3' Mlt) W/direct Access To Peconic Bay. Large Waterfront Deck, Lush Grounds W/waterfall, Gourmet Kitchen W/granite, Finished Lower Level, And 2 Fireplaces. Separate Uti...

Breathtaking Views Of The Sound All The Way To ...

REDUCED 6%

$1,549,000

17975 Soundview Ave, Southold

  • 3 Beds
  • 2 Baths
  • 1.2 Acres

School District: Southold

Breathtaking Views Of The Sound All The Way To Connecticut Are Yours In This Light Filled Home. Very Private Setting On Beautifully Landscaped 1.4 Acres. 115' Of Beachfront. Beautifully Renovated With Open Floor Plan Ideal For Summer Entertaining. New Kitch...

Situated On 6.75 Tranquil And Very Priv. Acres,...

REDUCED 3%

$1,545,000

1475 Waterview Dr, Southold

  • 5 Beds
  • 2 Baths
  • 6.75 Acres

School District: Southold

Situated On 6.75 Tranquil And Very Priv. Acres, This Is One Of The Last Large Goose Creek Waterfront Parcels And Has The Possibility Of Encompassing 3 Add'l Building Lots. This Charming Circa 1850 Historic Home, Known As The Pease Property, Includes 5 Brs, ...

Immaculate Home With 100' Of Creek Front, Priva...

$1,495,000

225 South Lakeside Dr, Southold

  • 3 Beds
  • 4 Baths
  • 0.48 Acres
  • 2,600 sqft

School District: Southold

Immaculate Home With 100' Of Creek Front, Private Dock, Waterside Salt Water Pool Set Into Custom Mahogany Deck And Gazebo, All Within A Short Distance To Private Association Sandy Bay Beach. Dock Can Accommodate Craft Up To 24' With Passage To Bay In Under...

Southold Circa 1910 Converted Barn. This Is You...

$1,475,000

622 Lighthouse Rd, Southold

  • 3 Beds
  • 2 Baths
  • 1.56 Acres
  • 2,800 sqft

School District: Southold

Southold Circa 1910 Converted Barn. This Is Your Opportunity To Own A Truly Special Property On The North Fork. Set On 1.5 Secluded Acres. Brilliantly Renovated Combining Original Rustic Barn Details With Modern Amenities. Original Exposed Wood Beams, And S...

3,400sqft Traditional Home W/ A Contemporary Vi...

$1,400,000

90 Kimberly Ln, Southold

  • 4 Beds
  • 3 Baths
  • 1.09 Acres
  • 3,400 sqft

School District: Southold

3,400sqft Traditional Home W/ A Contemporary Vibe, Located On One Of Southold's Most Coveted Streets.4-beds,2.5-baths, Living Room W/ Fireplace, Formal Dining, & Large Den Open To A Gourmet Kitchen & Breakfast Area.double French Doors Lead Out To A Stone Pa...

Stunning Panoramic Bay Front Views With 100 Ft ...

REDUCED 7%

$1,389,000

435 Watersedge Way, Southold

  • 3 Beds
  • 1 Baths
  • 0.48 Acres
  • 990 sqft

School District: Southold

Stunning Panoramic Bay Front Views With 100 Ft Of Sandy Private Beach. Home Is Set On A Gracious Lawn That Is Fully Bulk-headed. Impeccably Maintained Ranch, Offering One Floor Living With Foyer, Living Room With Wood Burning Fireplace, Eat-in Kitchen, Parq...

Enchanting Stone Tuscan Style Home, Surrounded ...

NEW

$1,375,000

1760 Reydon Dr, Southold

  • 4 Beds
  • 2 Baths
  • 1 Acres

School District: Southold

Enchanting Stone Tuscan Style Home, Surrounded By Incredible Gardens With Labyrinth! Enjoy Incredible Sunrises And Breezy Afternoons From This Waterfront Property With Deep Water Dock On The Inlet With Direct Access To Peconic Bay. 4 Bedrooms, 2 Baths, Huge...

Views, Views, Views! Fresh, Move-in, Light-fill...

REDUCED 6%

$1,299,000

20845 Soundview Ave, Southold

  • 3 Beds
  • 2 Baths
  • 0.64 Acres
  • 1,400 sqft

School District: Southold

Views, Views, Views! Fresh, Move-in, Light-filled Sound Front Contemporary. Recent Renovation Sparkles Throughout. Fabulous Feeling In This Modern, Convenient, One-level Waterfront Home With Stellar Sound Views. Your Own Stairs To Bulkheaded Waterfront. Ac...

A Long Tree Lined Drive To This Custom Built 4 ...

$1,299,000

535 Lighthouse Rd, Southold

  • 4 Beds
  • 3 Baths
  • 5.38 Acres
  • 2,850 sqft

School District: Southold

A Long Tree Lined Drive To This Custom Built 4 Br, 2.5 Bath Post Modern. Sited On 5+ Private Acres. Perfect For Horses, Vineyard Or Many Other Ideas. The Choice Is Yours. Large Great Room With Stone F/p Opens Into A Gourmet Kitchen, Dbl Ovens, Granite Tops,...

Entertainers' Delight On The North Fork! Patio...

REDUCED 6%

$1,295,000

1080 Kimberly Ln, Southold

  • 4 Beds
  • 3 Baths
  • 0.95 Acres

School District: Southold

Entertainers' Delight On The North Fork! Patio, Deck, Pool, Hot Tub And Private Beach Access... Great Home For A Summer Party And Bbq. Spacious Modern Eat In Kitchen, Den With Fireplace Plus Formal Living Room And Dining Room Gives The Homeowner The Choic...

Southold - Angel Shores Bayfront Community - S...

$975,000

805 Water Terrace, Southold

  • 4 Beds
  • 3 Baths
  • 0.7 Acres
  • 2,700 sqft

School District: Southold

Southold - Angel Shores Bayfront Community - Spacious & Light Filled 4-5 Bedroom 3 Bath Traditional Featuring A Stunning Custom Designed Chef's Kitchen, Great Room W/fireplace, Living Room & Formal Dining Room Including Master Bedroom Suite With Gorgeous C...

The Allen Tobey Carriage House Was Built In 191...

$975,000

3295 Pine Neck Rd, Southold

  • 3 Beds
  • 3 Baths
  • 0.84 Acres
  • 3,482 sqft

School District: Southold

The Allen Tobey Carriage House Was Built In 1910 And Moved To Its Present Location To Become A Residence In The 1950's. It Is One Of The Iconic Red Jockey Creek Houses With History And Charm Located On A Flag Lot With 10' Access To The Creek. Features Inclu...

Southold Quintessential Farmhouse C. 1898 Livin...

REDUCED 14%

$949,000

13675 Main Bayview Rd, Southold

  • 6 Beds
  • 3 Baths
  • 0.9 Acres
  • 3,093 sqft

School District: Southold

Southold Quintessential Farmhouse C. 1898 Living Room, Dining Room, And Den With Built-ins. Wood Floors, Original Doors And Moldings. Large Kitchen With Walk In Pantry. Mud Room With Stone Fireplace And Stone Bathroom, An Office And Screened Porch Complete ...

North Fork Charm Meets Modern Living In This Ne...

REDUCED 5%

$949,000

475 Midfarm Rd, Southold

  • 3 Beds
  • 2 Baths
  • 0.76 Acres
  • 2,160 sqft

School District: Southold

North Fork Charm Meets Modern Living In This Newly Renovated 3 Bed 2 Bath Home Built With An Eye For Design And Uncompromising Quality. Located On One Of Southold's Quietest Streets Yet Just Steps From Downtown Southold's Restaurants, Shops And Jitney/lirr ...

Location! Location! Location! 3 Houses From ...

$899,000

1275 The Esplanade, Southold

  • 3 Beds
  • 3 Baths
  • 0.83 Acres

School District: Southold

Location! Location! Location! 3 Houses From The Community Bay Beach On 0.83 Acres. Inground Heated Gunite Pool With Waterfall Feature. So Close To Beach That You Can Hear The Waves Crash On The Shore From Your Porch Or Pool Side Patio. Nicely Updated. ...

Motivated Seller!! Location! Build You Dream Ho...

REDUCED 10% Photo of Listing #3124731

$895,000

1080 Ackerly Pond Ln, Southold

  • 23.9 Acres

School District: Southold

Motivated Seller!! Location! Build You Dream House On 1.5 Acres Cleared Land, Surround By 22.4 Acres Of Drs (development Rights Sold) Acreage. Seller Is A Builder, Will Build To Suit A Custom Home & Outbuildings Or Bring Your Owner Builder. Land Is Set On C...

Drop Your Bags And Your Worries! Completely Ren...

$879,000

230 Jockey Creek Dr, Southold

  • 4 Beds
  • 2 Baths
  • 0.5 Acres
  • 1,630 sqft

School District: Southold

Drop Your Bags And Your Worries! Completely Renovated Impeccable Coastal Style Waterfront Home Nestled On Jockey Creek With Your Own Dock, Waterside Pool And Recreation Room. Easy Access To The Bay, Close To Town And All Your Favorite Adventures. This Turnk...

Lighthouse Inspired Lakefront Beach House With ...

REDUCED 12%

$875,000

175 Lake Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.5 Acres
  • 2,100 sqft

School District: Southold

Lighthouse Inspired Lakefront Beach House With Views Of Sun Setting In Li Sound. This 3-4 Bedroom, Two Bath, Mint Condition Beach House Is The Perfect Location For A Summer Retreat For Your Family. Located On A Quiet Country Lane With Water Views Out Of E...

Boaters Delight! 4 Bedroom 2 Bathroom Cape With...

$869,000

3995 Wells Ave, Southold

  • 4 Beds
  • 2 Baths
  • 0.51 Acres
  • 2,000 sqft

School District: Southold

Boaters Delight! 4 Bedroom 2 Bathroom Cape With Hardwood Floors Throughout, Spacious Bedrooms, And Potential For Open Floor Plan In Living Area. Private Deep Water Dock Perfect For All Water Sports, 4.5 Feet At Low Tide, Direct Bay Access. Enjoy Waterfront ...

Waterfront Ranch With Dock .enter From The Deli...

$850,000

590 Budds Pond Rd, Southold

  • 2 Beds
  • 2 Baths
  • 0.37 Acres
  • 1,560 sqft

School District: Southold

Waterfront Ranch With Dock .enter From The Delightful Covered Front Porch & You Are Immediately Drawn To The Lovely Waterview Through Big Picture Windows. The Interior Has A Open Floor Plan. The Kitchen, Dining Area, & Living Rm W/ Gas Flp All Have A Water...

Beautiful Country Home On 1.5 Acres W/ Lovely V...

$849,000 Under Contract

7630 Main Bayview Rd, Southold

  • 4 Beds
  • 2 Baths
  • 1.1 Acres

School District: Southold

Beautiful Country Home On 1.5 Acres W/ Lovely Views Of Corey Creek, Set Far Back From Road, Quiet & Serene. 4 Large Bedrooms, 1.5 Baths, Huge Updated Eik W/ Brand New Ss Appliances, Granite Counters And Walk In Pantry Area. Large Living Room With Wood Burn...

A Classic Beach Bungalow Set High On A Bluff Ov...

$843,000

1705 Arshamomaque Ave, Southold

  • 4 Beds
  • 3 Baths
  • 0.47 Acres

School District: Southold

A Classic Beach Bungalow Set High On A Bluff Overlooking The Water With Deep Water Dock And Panoramic Views To The Bay. Enjoy The Tranquility Of This Location At The End Of A Private Road, Nestled Among A Few Private Homes With Deeded Beach Access Just Beyo...

Spectacular Custom Home. New Construction Situa...

REDUCED 3%

$825,000 Under Contract

8025 Main Bayview Rd, Southold

  • 4 Beds
  • 4 Baths
  • 1.2 Acres
  • 3,000 sqft

School District: Southold

Spectacular Custom Home. New Construction Situated On 1.2 Acres. Highest Quality Materials & Finishes. Cobble Stone Lined Driveway, Bluestone Patios & 3 Trex Decks. First Floor Master Wing W/ Huge Walk Closet & Private Deck, Eik W/ Quartz Countertops/ss A...

Ultimate Getaway! Serene Wooded 2+ Acres. Craft...

$814,999

3520 Old North Rd, Southold

  • 3 Beds
  • 2 Baths
  • 2.17 Acres
  • 2,100 sqft

School District: Southold

Ultimate Getaway! Serene Wooded 2+ Acres. Craftsman Cabinets, Granite, Ss Appl, Brazilian Cherry Hardwood Fls, French Drs Leading To The Great Rm. Andersens & Custom Moldings. Spacious Mstr, Unfin Bonus Room, Updt, Bth's,new Paved Walk & Dw, Full Bsmt W/ste...

Stunning Chalet-style Home, Impeccably Built An...

REDUCED 5%

$799,000 Under Contract

14395 Main Bayview Rd, Southold

  • 3 Beds
  • 2 Baths
  • 2.18 Acres
  • 2,000 sqft

School District: Southold

Stunning Chalet-style Home, Impeccably Built And Maintained. Covered Porches Perfect For Outdoor Entertaining. Open Floor Plan, Kitchen/dining + Living With Soaring Stone Fireplace At Center Stage. 3 Bedrooms, 2 Baths Perfectly Situated On Over 2 Acres Of L...

New Construction To Be Built! Stunning 2300 Sq...

$799,000

1680 Seawood Dr, Southold

  • 4 Beds
  • 4 Baths
  • 0.34 Acres
  • 2,356 sqft

School District: Southold

New Construction To Be Built! Stunning 2300 Sq. Ft. 4br, 3.5 Bath Cedar Shake Two Story Home. First Floor Features Open Floor Plan With Beautiful Great Room W/ Fireplace, Den, 1/2 Bath, Screened In Porch To Enjoy Summer Breezes Plus A Br With Full Bath Pe...

This Is The Best Of The North Fork! Come Home T...

$799,000 Under Contract

215 Garden Ct, Southold

  • 4 Beds
  • 3 Baths
  • 0.6 Acres

School District: Southold

This Is The Best Of The North Fork! Come Home To This Lovely Dutch Colonial Located On A Quiet Cul-de-sac. Wonderful Private Garden W/ Privets Around Your 20x40 Ig Heated Swimming Pool. This Home Welcomes You And Your Guests W/ 4 Brs, 3 Full Baths, Formal D...

Turn Key & Built For Entertaining. This Traditi...

REDUCED 5%

$799,000

625 Kenneys Rd, Southold

  • 4 Beds
  • 3 Baths
  • 1.84 Acres
  • 2,800 sqft

School District: Southold

Turn Key & Built For Entertaining. This Traditional Style Home Offers Open Living On The Main Level W/ Updated Eik, Living Room & Den All Leading Out To An Impressive Poolside Patio & Deck. Manicured Plantings Established Throughout The Rear & Front Yard W/...

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