SOUTHOLD, NY
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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: 145
Average Price: $785,178
Highest Price: $2,500,000
Lowest Price: $149,900

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Southold Homes For Sale

145 Properties Found. Page 1 of 4
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Custom Spacious, Light Filled 3 Bedroom Waterfr...

NEW Photo of Listing #2950011

$895,000

240 Windjammer Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.66 Acres
  • 2,342 sqft

School District: Southold

Custom Spacious, Light Filled 3 Bedroom Waterfront In Harbor Lights Beachfront Community. Open Floor Plan W/vaulted Ceiling, Skylights, 2-story Stone Fireplace, Inviting Screened Porch Brings The Outside In. Large Deck To Enjoy Water Views & Bay Breezes. 2...

Gorgeous, Light, Bright & Airy! This Immaculate...

NEW Photo of Listing #2950221

$335,000

2555 Youngs Ave 19d, Southold

  • 2 Beds
  • 2 Baths
  • 0.18 Acres
  • 1,200 sqft

School District: Southold

Gorgeous, Light, Bright & Airy! This Immaculate 2 Bedroom, 2 Bath Condo Is The Ideal Place To Retire. Magnificent Location In The Heart Of Southold, Just A Stroll Away From Town!

Lovely 2 Bedroom, 2 Bath Condo In The Sought Af...

NEW Photo of Listing #2950223

$399,000

2555 Youngs Ave 9a, Southold

  • 2 Beds
  • 2 Baths
  • 0.02 Acres
  • 1,200 sqft

School District: Southold

Lovely 2 Bedroom, 2 Bath Condo In The Sought After Over 55 Founders Village Community. Full Basement, Lr W/ Fp. Pool And Clubhouse Within Complex. Close To Public Transportation, Town, Parks And Beaches.

Sophisticated Soundfront Cottage ~ Nestled Betw...

NEW Photo of Listing #2949970

$1,495,000

20275 Soundview Ave, Southold

  • 3 Beds
  • 2 Baths
  • 0.42 Acres
  • 1,200 sqft

School District: Southold

Sophisticated Soundfront Cottage ~ Nestled Between The Spectacular Sound & Bucolic Vineyards, This Charming & Chic 3br 2 Bath Traditional Cedarshake Has Just Been Fully Renovated. This New Light-filled, Open Concept With Waterviews From Almost Every Room Is...

Great Waterfront Offering With Sailing, Kayakin...

NEW Photo of Listing #2949991

$499,000

295 Bayview Ave, Southold

  • 1 Beds
  • 0.19 Acres

School District: Greenport

Great Waterfront Offering With Sailing, Kayaking And Paddle Boarding At Your Doorstep. At The End Of A Cul-de-sac This Recently Updated Year-round Cottage Has Everything You Need. A Painted Front Porch Welcomes You Into A The Main Living Room Dining Room ...

1 Acre Of Waterfront Property On Corey Creek In...

NEW Photo of Listing #2949770

$375,000

8150 N Bayview Rd, Southold

  • 1 Acres

School District: Southold

1 Acre Of Waterfront Property On Corey Creek Inlet To Build Your New Home In Southold. Board Of Health Approvals Already, Survey Completed, Can Have Dock Within Inlet For Boat. Plan Your New Home And Build. Electric And Paved Roads Already There.

Exquisitely Constructed, No Detail Spared, Over...

NEW Photo of Listing #2949272

$2,250,000

915 N Lakeside Dr, Southold

  • 4 Beds
  • 4 Baths
  • 1.03 Acres
  • 4,800 sqft

School District: Southold

Exquisitely Constructed, No Detail Spared, Over 230' Of Waterfront & Deep Water Dock On Cedar Beach Creek. Open Floor Plan, Soaring Ceilings, Gmt Kit, Fdr, 3 Fpl, 4 Br Incl 2 Mst Suites, 4 Ba, Office, Media Rm, 2 Laundry Rm & 2.5 Car-gar. Magnificent Views...

Tasteful Blend Of Old & New, Quality New Englan...

NEW Photo of Listing #2948443

$1,250,000

1035 Beachwood Ln, Southold

  • 4 Beds
  • 4 Baths
  • 0.51 Acres
  • 4,085 sqft

School District: Southold

Tasteful Blend Of Old & New, Quality New England Home Overlooks Goose Creek. Gourmet Kitchen, Professional Viking Cook Top & Wine Fridge Opens To Great Rm/fireplace. Enter Gracious Atrium Foyer Between Water View Sun Room & Formal Dining Room. 1st Floor Mas...

Eastward Cottage-georgian Revival, Historic Hom...

NEW Photo of Listing #2948533

$999,000

1600 Mount Beulah Ave, Southold

  • 3 Beds
  • 3 Baths
  • 0.5 Acres

School District: Southold

Eastward Cottage-georgian Revival, Historic Home. Brick Construction, Slate Roof, Copper Fittings,& Delightful Brick Garden House Just Waiting For Your Creative Imprint. 3 Bedrms, 2.5 Baths, Dining Rm, Living Rm, English Country Kit. W/charming Butler's Pan...

New To The Market. Authentic North Fork Farmhou...

NEW Photo of Listing #2948587

$579,000

49805 Route 25, Southold

  • 4 Beds
  • 2 Baths
  • 0.55 Acres
  • 2,500 sqft

School District: Southold

New To The Market. Authentic North Fork Farmhouse. Lots Of Charming And Original Details. Updated Kitchen, Open Spacious Living Room And Den With Copper Hooded Fireplace. Formal Dining Room, Eat-in Kitchen. Four Bedrooms, 1.5 Baths. Great Attic! House Is Ni...

Your Summer Fun Begins Here! Located In Desirab...

Photo of Listing #2946982

$498,990

1150 Bayview Ave, Southold

  • 3 Beds
  • 2 Baths
  • 0.34 Acres
  • 1,250 sqft

School District: Greenport

Your Summer Fun Begins Here! Located In Desirable Summerhaven, This 3 Bedroom Boasts 2 Full Baths, Family Rm, Study, Basement W/ose, Garage And More. Beautiful Oak Floors Throughout. Waterview With Boat Ramp Close By. Swimming, Boating, Kayak, Canoe In Win...

Southold - Laughing Waters - Water View Cottage...

Photo of Listing #2947347

$479,000

780 Minnehaha Blvd, Southold

  • 2 Beds
  • 2 Baths
  • 0.37 Acres
  • 1,056 sqft

School District: Southold

Southold - Laughing Waters - Water View Cottage. Experience Barefoot Summer Days. Community Beach And Marina. Two Bedroom, Two Bath, Great Room With Vaulted Ceiling. Indoor-outdoor Living. Fabulous Potential For Charming, Prime Location North Fork Property.

Rare Opportunity To Build Your Dream Home On Th...

Photo of Listing #2946959

$775,000 Under Contract

1071 Bay Home Rd, Southold

  • 0.51 Acres

School District: Southold

Rare Opportunity To Build Your Dream Home On This Vacant Half Acre Lot With Over 100' Of Waterfront. Enjoy Warm Bay Breezes And Spectacular Views From This Special Location. See Video/virtual Tour.

The Gold Standard In Waterfront Living! Easy C...

Photo of Listing #2946339

$549,000

980 Oak Ave, Southold

  • 2 Beds
  • 1 Baths
  • 0.22 Acres

School District: Southold

The Gold Standard In Waterfront Living! Easy Connection To Worlds Beyond Your Front Door. Get Access To All The East End Has To Offer With Your Boat Parked Outside Your Door And A Quarter Mile Of Unobstructed Water Views From Anywhere. Build A Spectacular...

Southold Vacant Residential Lot That Is Level A...

Photo of Listing #2945143

$182,499 Under Contract

2600 Youngs Ave, Southold

  • 0.32 Acres

School District: Southold

Southold Vacant Residential Lot That Is Level And Cleared And Backs Up To Preserved Land With Vineyard. 2 Blocks Away From Southold Village Shops And Transportation. Across The Street From Founders Village Complex. Short Distance To Southold Park District B...

Expansive 3 Bedroom 2 Bath Ranch In Laughing Wa...

Photo of Listing #2944112

$569,000

810 Hiawathas Path, Southold

  • 3 Beds
  • 2 Baths
  • 0.67 Acres
  • 1,650 sqft

School District: Southold

Expansive 3 Bedroom 2 Bath Ranch In Laughing Waters Beach Community. Newly Updated With An Inviting, Sunny, Bright Lr, Fdr, Eik/ Great Room With Wood-burning Stove And Rear Deck. Attached One Car Garage With Additional Storage And Bright Open Basement. Ver...

Pristine Single Level Living. Meticulously Main...

REDUCED 3% Photo of Listing #2944127

$599,000

295 Bennett Ln, Southold

  • 3 Beds
  • 2 Baths
  • 0.41 Acres
  • 1,600 sqft

School District: Southold

Pristine Single Level Living. Meticulously Maintained And Updated 3 Bedroom, 2 Bathroom Ranch. Wood Floors Throughout, Crown Molding, And Wood Burning Fireplace. Paver Driveway And Large Backyard. Close To Southold Village Amenities And Goose Creek Beach.

: Newly Updated. Shy Acre, Waterfront Property,...

Photo of Listing #2946791

$634,000

3145 N Main Bayview Rd, Southold

  • 4 Beds
  • 3 Baths
  • 0.86 Acres
  • 2,500 sqft

School District: Southold

: Newly Updated. Shy Acre, Waterfront Property, Beautiful Views, And Private Dock. Home Can Accommodate Lots Of Guests! Great Outdoor Dining On The Water, Lots Of Indoor Dining And Living Space With Water Views Or Vineyard Views From Every Window! 4-bedroo...

As This Home Nears Completion, It Has Surpassed...

Photo of Listing #2943775

$995,000

435 Willow Pond Ln, Southold

  • 4 Beds
  • 4 Baths
  • 0.92 Acres
  • 2,700 sqft

School District: Southold

As This Home Nears Completion, It Has Surpassed Expectations. Beautifully Constructed, With Interesting Architectural Details, A Hamptons Style Home In The Heart Of Southold In A Park-like Setting With A Heated Pool. A Well-equipped Chef's Kitchen, First ...

Beautifully Maintained Waterfront Home On Jocke...

REDUCED 6% Photo of Listing #2942738

$1,699,000

505 Light House Ln, Southold

  • 4 Beds
  • 4 Baths
  • 1.2 Acres
  • 2,400 sqft

School District: Southold

Beautifully Maintained Waterfront Home On Jockey Creek With Deepwater Dock, Wide Open Creek-views In A Very Private Location. Top Quality Custom Built Cape Cod With 4 Bedrooms, 3.5 Baths And Heated Enclosed Porch On 1.2 Acres.

Private, Pristine Colonial In Southold Gardens,...

Photo of Listing #2940899

$759,000

380 Garden Ct, Southold

  • 3 Beds
  • 3 Baths
  • 0.56 Acres
  • 2,052 sqft

School District: Southold

Private, Pristine Colonial In Southold Gardens, Bordering Preserved Land &walking Distance To Town Located In Southold Park District With Access To All Beaches , Close To A Marina., Jitney, Park &beaches,3+brs 3 Bths Finish Basement Cac, Security System,sto...

Welcome To Paradise! Boater's Delight! 84' Vin...

Photo of Listing #2938598

$1,100,000

750 Budd's Pond Rd, Southold

  • 3 Beds
  • 3 Baths
  • 0.31 Acres
  • 2,500 sqft

School District: Southold

Welcome To Paradise! Boater's Delight! 84' Vinyl Bulkhead, Floating Dock, Deep Water, Unobstructed And 2 Minutes To The Bay! Open Floor Plan With Vaulted Ceiling, Wood Deck! Hi Hat Lighting, Central Air, 3 Bedrooms And 3 Full Baths. Anderson Windows! ...

Immaculate Ranch Located In Founder's Park Dist...

REDUCED 6% Photo of Listing #2938747

$505,000 Under Contract

810 Greenfields Ln, Southold

  • 3 Beds
  • 2 Baths
  • 0.97 Acres
  • 1,725 sqft

School District: Southold

Immaculate Ranch Located In Founder's Park District. Sit On Your Front Porch Or Back Patio Where There Is Plenty Of Room For A Pool On This Just Shy Of An Acre Property. Close To Town.

5.7 Acres, Front 1.7 Acres Are Zoned Hamlet Bus...

Photo of Listing #2938811

$1,299,000

56995 Route 25, Southold

  • 5 Beds
  • 2 Baths
  • 5 Acres
  • 2,500 sqft

School District: Southold

5.7 Acres, Front 1.7 Acres Are Zoned Hamlet Business And Back 4 Acres Are Zoned Agricultural. Perfect For A Gentleperson's Farmstead, B&b, Or Convert To Business Use (check Permitted Uses.) Also Subdivision Possibilities.. Two Large Barns And A Victorian F...

This Shy 2.5 Acre Property Is A Peaceful Place ...

Photo of Listing #2938220

$750,000

9502 N Bayview Rd, Southold

  • 3 Beds
  • 3 Baths
  • 2.44 Acres

School District: Southold

This Shy 2.5 Acre Property Is A Peaceful Place Near Paradise Point. The Property Has A Quality Home Well Under Construction With A Traditional Open Floor Plan With Finished Features Throughout. There Is A Barn And Corral In Place For A Horse Owners Dream. ...

New To The Market! Wonderful Waterfront, 1.4 A...

Photo of Listing #2937352

$1,849,000

835 Tarpon Dr, Southold

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

School District: Greenport

New To The Market! Wonderful Waterfront, 1.4 Acres, With Panoramic Views; Deep Water Dock Can Handle Substantial Boats. Waterviews From Living Room W/fireplace, Dining Room, Eik, Family Room W/fireplace And 3 Bedrooms. 3-4 Bedrooms, 3 Baths, Wine Cellar, G...

Enjoy The Peace & Luxury Of Li North Fork.custo...

Photo of Listing #2937581

$1,695,000

3370 Paradise Point Rd, Southold

  • 5 Beds
  • 4 Baths
  • 2.76 Acres
  • 4,300 sqft

School District: Southold

Enjoy The Peace & Luxury Of Li North Fork.custom Built On 2.76 Acs In Highly Desirable Paradise Point. One Of A Kind Home W/access To Boat Basin, Docks & Bay Beach. Pristine 5 Br,3.5 Bths Post Modern. Large High End Kitchen, Hardwood & Marble Flooring Thro...

Beautiful Ranch In A Prime Location!! Minutes F...

Photo of Listing #2936853

$319,900 Under Contract

670 Grove Rd, Southold

  • 3 Beds
  • 2 Baths
  • 0.32 Acres
  • 1,520 sqft

School District: Southold

Beautiful Ranch In A Prime Location!! Minutes From Gorgeous Water/beach Fun At Southold Town Beach . Three Airy Bedrooms, 1 1/2 Baths For Your Summer Escape Or Year Round Sanctuary. Plenty Of Space In The Rear Yard For Entertaining. Water View Of Hashamomuc...

Sweet Charming 3 Bedroom Ranch With Cac And Flo...

Photo of Listing #2937177

$475,000

1050 Long Creek Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.53 Acres
  • 1,700 sqft

School District: Southold

Sweet Charming 3 Bedroom Ranch With Cac And Florida Room. Close To Beaches, Shopping, Transportation. Perfect Getaway For Second Home Buyer. Room For Expansion And Pool.

Beautifully Appointed Stone&wood Exp Cape, W/ W...

Photo of Listing #2935939

$780,000

1250 Bayview Ave, Southold

  • 3 Beds
  • 4 Baths
  • 0.34 Acres
  • 2,400 sqft

School District: Southold

Beautifully Appointed Stone&wood Exp Cape, W/ Waterviews From All Front Windows Up & Down, Master Crafted Fireplace & Customwoodwork Throughout, Lst Fl Master Bedroom Suite W/walk-in Closet, Powder Room, Linen& Sep Rm For Bath (sep Jacuzzi & Walk In Shower)...

Large Home Diamond Condition Must See, Complete...

REDUCED 4% Photo of Listing #2935187

$529,000

605 Seawood Dr, Southold

  • 4 Beds
  • 4 Baths
  • 0.28 Acres
  • 2,500 sqft

School District: Southold

Large Home Diamond Condition Must See, Completely Renovated 4 Bed, 3.5 Bath Cape-style Home. An Open Layout On The 1st Floor Offers A Beautifully Updated Granite Eat-in Kitchen & Spacious Family Room Leading Out To New Custom Built Trex Deck. Additional Upd...

Arts & Craftsman Contemporary On Private, Seclu...

Photo of Listing #2935358

$795,000

460 Anderson Rd, Southold

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

School District: Southold

Arts & Craftsman Contemporary On Private, Secluded, Deer-fenced And Well Landscaped 1.2 Acre Property W/deeded Li Sound Beach. Hickory Grove Features Open Plan W/lots Of Natural Light, Woodstove In Lr, Master Suite, Screened In Cocktail Porch, Guest Rooms,...

Southold North Fork: Look No Further - Move In...

REDUCED 2% Photo of Listing #2934997

$559,000

1150 S Harbor Rd, Southold

  • 3 Beds
  • 2 Baths
  • 0.5 Acres
  • 1,500 sqft

School District: Southold

Southold North Fork: Look No Further - Move In Ready Ranch By Beach - Immaculate. Sunken Pool In Deck W/pergola - Overlooks Daily Incredible Sunsets. Lush And Private Landscaping. Home Features Lr W/fp, Dr, Eik, Mbr W/bath And 2 Additional Br And Bath. ...

This Eclectic Chateau On 1.06 Acres Offers 4 Be...

Photo of Listing #2935021

$2,500,000

1700 Hyatt Rd, Southold

  • 6 Beds
  • 6 Baths
  • 1.06 Acres
  • 6,365 sqft

School District: Southold

This Eclectic Chateau On 1.06 Acres Offers 4 Bedrooms And 4.5 Baths In The Main House, While The Legal 2 Bed 2 Bath Accessory Apartment Is Perfect For Staff, Weekend Guests Or Family And Friends. Upscale Fixtures, Imported Tiles And Marble, Hardwood Floorin...

Ready To Move In - Centrally Located Ranch, Clo...

REDUCED 5% Photo of Listing #2933898

$429,000

730 Pine Neck Rd, Southold

  • 4 Beds
  • 2 Baths
  • 0.38 Acres

School District: Southold

Ready To Move In - Centrally Located Ranch, Close To Town, Bay, Sound Beaches And Wineries. Bright Sunroom Overlooking Spacious Backyard. Family Room W/ Fireplace. Living / Dining Rm, Eik, 4 Brs, 2 Bths. 2-car Garage.

Gracious Modern 4 Bedroom Farmhouse Set Among S...

Photo of Listing #2933985

$729,000 Under Contract

46000 Main Road, Southold

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

School District: Southold

Gracious Modern 4 Bedroom Farmhouse Set Among Stately Trees, Privet Hedges And Flowering Shrubs. 19th Century Charm With 21st Century Amenities. Custom Designed & Meticulously Built With Farm Views From 2nd Story To Complete This Country Setting Between Two...

This Charming Cape Has Been Completely Renovate...

Photo of Listing #2934045

$559,000

1830 Boisseau Ave, Southold

  • 2 Beds
  • 2 Baths
  • 0.3 Acres
  • 1,700 sqft

School District: Southold

This Charming Cape Has Been Completely Renovated And Is Turn-key. The Light-filled Home Has 2 Beds & 1.5 Baths With Many Extras: A Private, Fenced-in Yard, Full Basement, Separate Garage, New Appliances, Radiant Heat In Kitchen & Dining, All New Windows, Ca...

A Great Opportunity To Own A Home In The Bayvie...

REDUCED 4% Photo of Listing #2934048

$429,000

1150 Seawood Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.34 Acres
  • 1,200 sqft

School District: Southold

A Great Opportunity To Own A Home In The Bayview Area Of Southold. This Quaint Country 3 Bedroom 1.5 Bath Ranch Has Plenty Of Potential And Is Situated On .34 Acre. Close To Area Beaches "sold As Is". All Information Should Be Independently Verified.

Jockey Creek Estates, One Of The Famous "red Ho...

Photo of Listing #2933700

$750,000 Under Contract

3775 Pine Neck Rd, Southold

  • 4 Beds
  • 2 Baths
  • 0.69 Acres

School District: Southold

Jockey Creek Estates, One Of The Famous "red Houses." Classic North Fork Colonial With 4 Bedrooms Including First Floor Master Suite And Double Fireplace In Living And Dining Rooms. Renovated In 2012. Two Big Bonuses! Separate Legal Studio Cottage Plus 20 F...

Southold Harbor Lights Bayfront Community - Wel...

Photo of Listing #2933743

$595,000 Under Contract

910 Brigantine Dr, Southold

  • 3 Beds
  • 3 Baths
  • 0.52 Acres
  • 1,523 sqft

School District: Southold

Southold Harbor Lights Bayfront Community - Well Maintained 3 Bedroom, 2.5 Bath Ranch On .52 Acres Overlooking 37 Acres Of Preserved Land. All Oak Flooring. New Central Air, Living Room With Fireplace, 2- Car Garage, Room For Pool. Steps To Harbor Lights A...

Enjoy This Sunny Contemporary Home, Convenient ...

Photo of Listing #2933554

$525,000

710 Shepard Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.44 Acres

School District: Southold

Enjoy This Sunny Contemporary Home, Convenient To Farmstands, Wineries, Beaches, And Everything North Fork. This Home Features An Open Interior, Great Room With Brick Fireplace, Three Decks Including A Charming Juliet Balcony. Great Spaces Indoors And Out...

Beautifully Renovated Cape, Convenient To Town....

Photo of Listing #2933404

$579,000 Under Contract

2650 Pine Neck Rd, Southold

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

School District: Southold

Beautifully Renovated Cape, Convenient To Town. Bay Beaches And Boat Launch. New Kitchen And Appliances. 3 Bedroom, 1 1/2 Bath, Generous Sized Rooms, Professionally Landscaped With Large Patio.

This Scenic And Private .44 Acre Waterfront Lot...

Photo of Listing #2932360

$299,000

415 S Lakeside Dr, Southold

  • 0.44 Acres

School District: Southold

This Scenic And Private .44 Acre Waterfront Lot Has Permits & Approvals In Place To Build A Two Story, 1,920 Sq. Ft., Residence With A 15' X 20' Attached Deck. With Direct Access To Gardiner's Bay And A Sandy Community Bay Beach Around The Corner, This Pro...

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