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: 97
Average Price: $792,963
Highest Price: $2,699,000
Lowest Price: $149,900

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Southold Homes For Sale

97 Properties Found. Page 1 of 3
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Large Cape With In-ground Pool Situated On Over...

NEW

$745,000

305 Tuthill Rd Ext, Southold

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

School District: Southold

Large Cape With In-ground Pool Situated On Over 1.25 Acres Surrounded By Mature Privacy Plantings And Perennial Gardens. Cozy Living Room Includes A Wood Burning Stove And Connects To The Dining Room W/ Sliding Glass Doors That Open On To The Large Deck And...

Inviting 3 Bedroom Ranch In The Coveted Harbor ...

NEW

$749,000

700 Harbor Lights Dr, Southold

  • 3 Beds
  • 1 Baths
  • 0.46 Acres
  • 1,575 sqft

School District: Southold

Inviting 3 Bedroom Ranch In The Coveted Harbor Lights Community Directly Across From Private Association Beach. Welcoming Floor Plan, Living Room With Fireplace, Kitchen And Dining Room. Sliding Doors Open To Large Deck For Summer Entertaining.

Perfect 55 Plus In Town Co-op To Call Home. En...

$182,000

55075 Route 25 1, Southold

  • 1 Beds
  • 1 Baths
  • 529 sqft

School District: Southold

Perfect 55 Plus In Town Co-op To Call Home. End Unit With Easy Access To Shopping, Transportation And Everything You Need. This Unit Offers An Updated Bathroom, Fresh Paint, Refinished Hardwood Floors.

Beautiful Homesite Overlooking Development Righ...

Photo of Listing #2995529

$350,000

4402-3 Old North Rd, Southold

  • 0.93 Acres

School District: Southold

Beautiful Homesite Overlooking Development Rights Sold Farmland Preserving Your Sunsets Forever. This Homesite Is Ready To Be Built Upon And Sits Near To An Historic 1820s Farmhouse With All The Charm Of The North Fork. Enjoy This Forever Protected Bucolic...

Beautiful Homesite Overlooking Development Righ...

Photo of Listing #2995532

$400,000

4402-4 Old North Rd, Southold

  • 1.27 Acres

School District: Southold

Beautiful Homesite Overlooking Development Rights Sold Farmland Preserving Your Sunsets Forever. This Homesite Is Ready To Be Built Upon And Sits Near To An Historic 1820s Farmhouse With All The Charm Of The North Fork. Enjoy This Forever Protected Bucolic...

Beautiful 1.27 Ac. Building Lot Overlooking Dev...

Photo of Listing #2995724

$750,000

4402-4&5 Old North Rd, Southold

  • 8.59 Acres

School District: Southold

Beautiful 1.27 Ac. Building Lot Overlooking Development Rights Sold Farmland Preserving Your Sunsets Forever. Flat And Level, This Homesite Is Ready To Be Built Upon And Sits Near To An Historic 1820's Farmhouse With All The Charm Of The North Fork. Include...

Unspoiled & Private 2.15 Acres, Level & Partial...

Photo of Listing #2994778

$460,000

13425 Main Bayview Rd, Southold

  • 2.15 Acres

School District: Southold

Unspoiled & Private 2.15 Acres, Level & Partially Cleared Has Many Gorgeous Specimen Trees To Enhance The Estate-like Quality Of The Land. Located On A Private Access Road Off Of Main Bayview & Just Around The Corner From Cedar Beach Park. A 68-acre Park Wi...

Southold Nunnakoma Waters- Land. 0.52 Acre Resi...

Photo of Listing #2993597

$370,000

50 Teepee Trl, Southold

  • 0.52 Acres

School District: Southold

Southold Nunnakoma Waters- Land. 0.52 Acre Residential Building Parcel In Desirable Beachfront Community. Level And Wooded, And Waiting For You To Build Your Dream Full-time Or Vacation Home. Town Water In Street. Deeded Sandy Beach And Marina With Direct ...

Wonderful Waterfront, 1.4 Acres, With Panoramic...

$1,799,000

835 Tarpon Dr, Southold

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

School District: Greenport

Wonderful Waterfront, 1.4 Acres, With Panoramic Views Include Sunset Beach! Deep Water Dock Can Handle Substantial Boats. Waterviews From Living Room W/fireplace, Dining Room, Eik, Family Room W/fireplace And 4 Bedrooms, 3 Baths, Wine Cellar, Gym, Very Priv...

Enjoy Forever Vineyard Views And Sunsets From T...

$1,495,000

1375 Ackerly Pond Ln, Southold

  • 4 Beds
  • 3 Baths
  • 10 Acres

School District: Southold

Enjoy Forever Vineyard Views And Sunsets From This Serene 10-acre Horse Farm In Bucolic Southold. The Property Boasts A 4 Bedroom, 3 Bath Updated Farmhouse, 2 Barns With 8 Stalls And 2 Tack Rooms, 100' By 200' Irrigated Riding Arena, And 5 Irrigated Paddock...

Nestled At The Tip Of The Founders Landing Area...

$574,999

1605 Old Shipyard Ln, Southold

  • 3 Beds
  • 3 Baths
  • 0.14 Acres
  • 3,000 sqft

School District: Southold

Nestled At The Tip Of The Founders Landing Area, This Expansive Home Sits Proudly Only One Block From The Coveted Founders Landing Beach. The Perfect Summer Retreat With Space For The Extended Family. Featuring Three Bedrooms And 2.5 Baths Spread Over Nea...

Located In Laughing Waters Beach/marina Communi...

REDUCED 1%

$375,000

190 Osseo Ave, Southold

  • 2 Beds
  • 1 Baths
  • 0.3 Acres

School District: Southold

Located In Laughing Waters Beach/marina Community On Corey Creek. Spacious Backyard With Screened Porch, Room To Entertain Or Expand. Take Advantage Of The North Fork Lifestyle In This Adorable Southold Beach Community Offering.

Picture Perfect Set On A Cul De Sac. Move In R...

$799,000 Under Contract

380 Garden Ct, Southold

  • 3 Beds
  • 3 Baths
  • 0.56 Acres

School District: Southold

Picture Perfect Set On A Cul De Sac. Move In Ready Is This 2 Story Home That Has Been Updated With Great Taste. Enjoy This Peaceful Location Yet Close To Town And The Jitney. Hardwood Floors, Cac, Private Backyard Are Just A Few Characters That Await.

Majestic 6300sf +, 5 Bed En-suite Looming High ...

$2,275,000

1700 N Hyatt Rd, Southold

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

School District: Southold

Majestic 6300sf +, 5 Bed En-suite Looming High On The Bluffs Of The Sound. Over 1 Acre In A Rare Nfork Location Where Value Far Exceeds Asking Price. Ride In The 3-story Elevator To Enjoy Sea Side Living; Cozy And Charming With 3 Fireplaces, Private Road, 1...

Historic And Charming 1820's Farmhouse Compound...

$500,000

4402-1 Youngs Ave, Southold

  • 3 Beds
  • 2 Baths
  • 1.01 Acres

School District: Southold

Historic And Charming 1820's Farmhouse Compound Featuring A 2 Story Barn With Lofts, Garage And Outbuildings That Speak To Days Gone By. The Ultimate In Classic Simplicity Translates Into A Fading Opportunity To Put Your Own Mark On Southold. Preserved Scen...

The Perfect East End Getaway! 3br 2 Bath Renov...

$499,000

985 Oak Ave, Southold

  • 3 Beds
  • 2 Baths
  • 0.19 Acres
  • 1,435 sqft

School District: Southold

The Perfect East End Getaway! 3br 2 Bath Renovated Cottage Nestled In Coveted Goose Bay Estates. Enjoy Summer Nights With Family And Friends Dining On The Screened Porch With Glimpses Of The Creek And Relaxing After A Tough Day At The Many Nearby Beautiful...

Beautiful Shy Acre Homesite Overlooking Develop...

Photo of Listing #2990425

$300,000

4402-2 Old North Rd, Southold

  • 0.91 Acres

School District: Southold

Beautiful Shy Acre Homesite Overlooking Development Rights Sold Farmland Preserving Your Sunsets Forever. Flat And Level, This Homesite Is Ready To Be Built Upon And Sits Adjacent To An Historic 1820s Farmhouse With All The Charm Of The North Fork. Enjoy ...

Weekend Getaway With Water Views Of Long Island...

REDUCED 7%

$789,500

1895 Leeton Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.5 Acres

School District: Southold

Weekend Getaway With Water Views Of Long Island Sound, 3 Bdr 2 Full Bath Exp Cape,eik, Great Room,hdw Pine Wood Flooring Thru Out,sets Of Sliding Glass Doors To Wraparound Deck, 2nd Floor Deck, 2 Skylights,out Door Shower, Enjoy The Beautifull Sunsets And M...

2.6 Acres Of Secluded Land Setback From The Roa...

Photo of Listing #2988367

$886,000

9785 Main Bayview Rd, Southold

  • 2.59 Acres

School District: Southold

2.6 Acres Of Secluded Land Setback From The Road. Your Own Private Sanctuary Just Outside Of Town And Moments From Some Of North Fork's Best Beaches. An Equestrian Or Winemakers Dream, Custom Craftsman Barn And Fenced In Backyard With Deck.

Rare Opportunity To Custom Build Your North For...

Photo of Listing #2986983

$249,000

415 S Lakeside Dr, Southold

  • 0.44 Acres

School District: Southold

Rare Opportunity To Custom Build Your North Fork Dream Home. Prime .44 Acre Waterfront Parcel With Survey, Nys Dec, Board Of Health, And Southold Town Trustee Permits In Place. Steps To A Private Sandy Association Bay Beach And Close To Cedar Beach Park. Be...

Calling All Buyers,colonial, 5 Bedrooms, 3 Bath...

REDUCED 25%

$485,000 Under Contract

1065 Jasmine Ln, Southold

  • 5 Beds
  • 3 Baths
  • 0.43 Acres

School District: Southold

Calling All Buyers,colonial, 5 Bedrooms, 3 Bathroom, Formal Living Rm, Dining Rm, Hardwood Floors, Room For Entertaining. 2 Car Detatched Garage, Add Your Own Touch And Made This Your Dream Home. The Subject Property Is Currently Used As A Summer House Fami...

This Lovely 4 Bedroom, 2 Bath Cape Cod Features...

REDUCED 4%

$525,000

15725 Soundview Ave, Southold

  • 4 Beds
  • 2 Baths
  • 0.43 Acres

School District: Southold

This Lovely 4 Bedroom, 2 Bath Cape Cod Features An Eat In Kitchen W/sliders To A Partially Covered Exterior Patio, 1 Car Attached Garage, Full Basement And Spacious Back Yard With Room For Pool. There Are Charming Built-ins, New Siding, Hardwood Floors On T...

The Quintessential Modern Farmhouse, Covered Fr...

$886,000

9785 Main Bayview Rd, Southold

  • 3 Beds
  • 3 Baths
  • 2.59 Acres

School District: Southold

The Quintessential Modern Farmhouse, Covered Front Porch, Open Kitchen Den Combo With Formal Living & Dining Space. Situated On 2.6 Acres Of Secluded Land Setback From The Road. Your Own Private Sanctuary Just Outside Of Town And Moments From Some Of North...

This Magnificient Waterfront Home Located In De...

$999,000 Under Contract

845 Budds Pond Rd, Southold

  • 3 Beds
  • 3 Baths
  • 0.59 Acres

School District: Southold

This Magnificient Waterfront Home Located In Desirable Willow Point Estates Has It All! With A Culdesac Location... Spectacular Views Of Shelter Island!!! Enjoy Hw Floors, Lvr W/ Frplc, Skylights, Central Air! Views From Every Window! Multi Decking Overl...

Location, Style, Privacy, Beach, Boating...this...

REDUCED 7%

$1,295,000

3735 Paradise Point Rd, Southold

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

School District: Southold

Location, Style, Privacy, Beach, Boating...this Property Has It All! Open Floor Plan With Plenty Of Natural Light To Highlight The Hardwood Floors And High Ceilings. Sprawling Entertaining Spaces Flow Outside To The Wood Deck Where You'll Enjoy Pond And...

Immaculate Discerning Only The Very Best For Th...

$749,000

80 Wild Cherry Way, Southold

  • 4 Beds
  • 3 Baths
  • 0.62 Acres

School District: Southold

Immaculate Discerning Only The Very Best For This No Stone Unturned Home. Palatial Grounds, Room For A Fabulous Pool. Clse To Greenport And Southold Town Shopping, Yet Protected And Serene Area.beautiful Peach Trees In Your Garden.

In The Heart Of Beautiful Southold, This Charmi...

$639,000

220 Mechanic St, Southold

  • 2 Beds
  • 3 Baths
  • 0.3 Acres

School District: Southold

In The Heart Of Beautiful Southold, This Charming Cottage Is Close To Library, Opera House, Shops And All Conveniences. Bright And Airy Entrance Leading Into An Updated Gourmet Eik, Equipped With Viking Appliances Open To Dr. Generous Lr W/ French Doors Ope...

Quaint North Fork Cedar Shingled Ranch With A G...

$465,000

100 Terry Ct, Southold

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

School District: Southold

Quaint North Fork Cedar Shingled Ranch With A Great Location Near Town And Between Both Long Island Sound And Peconic Bay Beaches To Enjoy. This Home Offers Many New Updates Throughout The Home Which Include Fresh Paint, Refinished Oak Floors, Etc... In Wh...

Charming North Fork Cottage In Beach Community ...

$599,000 Under Contract

580 Gin Ln, Southold

  • 3 Beds
  • 3 Baths
  • 0.65 Acres
  • 1,700 sqft

School District: Southold

Charming North Fork Cottage In Beach Community ~ This Enchanting 3 Bedroom 2.5 Bath Cedar Shake Cape Is Set On A Beautiful .65 Acre, Backed By Wooded Preserve With Natural Pond Views In The Popular Beach Community Of Bay Haven. Great Beach, Park, & Location!

The Lot,which Features 110 Ft Of Water Frontage...

Photo of Listing #2978825

$599,000

17877 Soundview Ave, Southold

  • 0.98 Acres

School District: Southold

The Lot,which Features 110 Ft Of Water Frontage, Sits On A 60 Ft High Bluff Overlooking The Li Sound. Located In The Beautiful Town Of Southold, This Land Is Ideally Located Near Hortons Point Lighthouse, Hashamomuck Pond, And Many Other Attractions. The M...

Natures Lovers Paradise!spacious A Frame Home S...

REDUCED 3%

$725,000

435 Private Rd, Southold

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

School District: Southold

Natures Lovers Paradise!spacious A Frame Home Secluded In The Woods For Your Ultimate Privacy. Just Off Soundview Ave. W/ Short Stroll To Kenneys Beach. Floor To Ceiling Windows On Main Floor. First Floor: Granite Kit W/ Prof. Stove, Dining Room & Lr W/ Fpl...

Adorable Cedar Shingled Cottage In Southold.. L...

$429,000

1825 Main Bayview Rd, Southold

  • 2 Beds
  • 1 Baths
  • 0.42 Acres

School District: Southold

Adorable Cedar Shingled Cottage In Southold.. Living Room And Sitting Room/office With Wood Pellet Stove. Large Kitchen, With Stainless Steel Appliances. Expansive Deck Overlooking Yard And Bucolic Views Of The Adjacent Tree Farm. Detached Garage.

Come Enjoy This Well-kept Ranch In Goose Creek ...

$457,000 Under Contract

475 Oakwood Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.34 Acres
  • 1,380 sqft

School District: Southold

Come Enjoy This Well-kept Ranch In Goose Creek Area; Beach, Boat Launch & Shopping. Open Eat In Kitchen W/granite, Lr W/fp, Mbr Ensuite, 2 Bedrooms,hall Bath, Ldry Area. Garage And Rear Deck.

Featured In Coastal Living Magazine, This Conte...

$1,800,000

1455 Cedar Point Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.47 Acres

School District: Southold

Featured In Coastal Living Magazine, This Contemporary Beach Cottage Overlooks The Peconic Bay, A Nature Preserve, And A Deep Water Inlet. 3 Bedrooms, 2 Baths, Open Concept, Including Living, Dining, Kitchen And An Entertainment Nook, Wood Burning Fireplace...

Currently Under Construction With A Late Fall C...

$869,000

285 Ripple Water Ln, Southold

  • 4 Beds
  • 3 Baths
  • 0.69 Acres
  • 2,560 sqft

School District: Southold

Currently Under Construction With A Late Fall Completion Date. Similar Home Shown In Photography Of Similar Floor Plan. Located In The Estates On West Creek, This Well Proportioned New Construction Offers Timeless Finishes, Open Floor Plan, And New Feature ...

Waterfront Paradise! Boater's Delight! 84' Vin...

$988,000

750 Budd's Pond Rd, Southold

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

School District: Southold

Waterfront 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! Very ...

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