Luxury homes for sale & real estate in Oyster Bay, NY

389 homes

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ABOUT THIS HOME
Luxury Home for sale in Oyster Bay, NY:
Welcome to 35 Chicken Valley Road, an extraordinary estate in the prestigious enclave of Old Brookville. This gated Brick Center Hall Colonial, masterfully built by the renowned Worrell Group, sits on 4.5 acres of impeccably manicured, estate-quality grounds and offers nearly 10,000 sq ft of finished living space across all levels. A circular drive leads to the stately entryway, accented by a stunning fountain that anchors the grand approach. Step inside to a breathtaking 22-foot entryway with soaring ceilings, intricate moldings, and wainscot paneling framing the sweeping staircase. The double-height foyer introduces refined formal spaces, including a living room with a wood-burning firepl

$5,699,999

6 beds7.5 baths7,200 sq ft

35 Chicken Valley Rd, Glen Head, NY 11545

Custom cabinetry • Stunning entryway • 4.5 acres of grounds

Listing by LAFFEY REAL ESTATE

ABOUT THIS HOME
Luxury Home for sale in Oyster Bay, NY:
0.4 mi to Syosset-Woodbury Community Park • Near Mongo’s Coffee • Fenced yard with patio & firepit Set on a quiet block, this expanded ranch blends comfort and functionality with an open layout connecting the renovated kitchen—featuring quartz counters and stainless-steel appliances—to generous living and dining areas. The home offers 3 bedrooms and 3 full baths, including a large primary suite with a spa-inspired granite bath, Jacuzzi tub, and separate shower. French doors lead to a fenced backyard with a new patio and firepit, ideal for relaxed outdoor living. The full basement spans the home’s footprint and includes a recreation area, playroom, fu

$949,000

3 beds3 baths1,357 sq ft

5 Willets Dr, Syosset, NY 11791

New patio • Quartz counters • Private playground

Listing by Compass Greater NY LLC

ABOUT THIS HOME
Luxury Home for sale in Oyster Bay, NY:
Set on a beautiful corner lot in the heart of Plainview’s most sought-after Washington Avenue neighborhood, this completely renovated residence showcases sophisticated design, high-end finishes, and effortless livability. Every element of the home has been thoughtfully reimagined—from the custom kitchen and designer baths to the flooring, lighting, and trim—creating a bright, modern aesthetic that feels brand new. The open-concept main living area is defined by soaring ceilings, abundant natural light, and a seamless flow that makes everyday living and entertaining equally inviting. The chef’s kitchen features bespoke cabinetry, quartz countertops, a large center isl

$1,495,000

5 beds2.5 baths2,011 sq ft

4 Long Ridge Rd, Plainview, NY 11803

Custom kitchen • Soaring ceilings • Corner lot

Listing by Nest Seekers LLC

OPEN SUN, 12:30PM TO 2PM

ABOUT THIS HOME
Luxury Home for sale in Oyster Bay, NY:
Welcome to this spacious 3-bedroom, 2.5-bath Knoll Model located in the gated community of Hidden Ridge. Filled with potential, this home is ready for you to make it your own. The upper level features three generously sized bedrooms and two full baths, providing comfortable living for all. The full finished basement offers exceptional bonus space, complete with an unrepresented full bath and a versatile playroom—perfect for recreation, guests, or a home office. Hidden Ridge offers resort-style amenities, including a clubhouse, inground pool, tennis courts, and a playground. All within the Syosset School District.

$899,888

3 beds2.5 baths1,926 sq ft

105 Glen Way, Syosset, NY 11791

Gated community • Clubhouse • Tennis courts

Listing by Compass Greater NY LLC

ABOUT THIS HOME
Luxury Home for sale in Oyster Bay, NY:
Set on two exceptional acres at the end of a private cul-de-sac, this classic 5-bedroom, 4-bath Colonial offers timeless elegance, privacy, and a rare connection to Long Island’s storied estate era. A long, sweeping driveway leads to the residence, which sits elevated on the property, creating a stately first impression against its beautifully wooded surroundings. This home occupies the historic site of the Sir Ashley Sparks Estate, Northaw, once part of a 275-acre retreat tied to prominent international figures. Blending history and opportunity, it offers traditional comfort and tremendous potential for customization or expansion. Inside, approximately 4,200 square feet of light-fill

$2,199,000

5 beds3.5 baths4,178 sq ft

62 Sabine Rd, Syosset, NY 11791

Natural landscaping • Gunite pool • Private cul-de-sac

Listing by Compass Greater NY LLC

Property at 60 Moss Ln, Jericho, NY 11753, 5 beds, 5.5 baths

$2,555,000

5 beds5.5 baths3,196 sq ft

60 Moss Ln, Jericho, NY 11753

Listing by Skylux Realty Inc

Property at 9 Princeton Dr, Plainview, NY 11803, 5 beds, 2.5 baths

$1,299,000

5 beds2.5 baths2,438 sq ft

9 Princeton Dr, Plainview, NY 11803

Listing by Howard Hanna Coach

Property at 51 Deer Ln, Hicksville, NY 11801, 4 beds, 2 baths

$899,000

4 beds2 baths1,720 sq ft

51 Deer Ln, Hicksville, NY 11801

Listing by Signature Premier Properties

Property at 9 Oak Shore Dr, Bayville, NY 11709, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths1,928 sq ft

9 Oak Shore Dr, Bayville, NY 11709

Listing by NY Space Finders Inc

Property at 20 Briarwood Ln, Plainview, NY 11803, 4 beds, 2 baths

$1,199,000

4 beds2 baths2,238 sq ft

20 Briarwood Ln, Plainview, NY 11803

Listing by Taft Corp

Property at 15 Vista Rd, Plainview, NY 11803, 3 beds, 2.5 baths

$1,150,000

3 beds2.5 baths1,800 sq ft

15 Vista Rd, Plainview, NY 11803

Listing by Compass Greater NY LLC

Property at 12 Orchard Dr, Woodbury, NY 11797, 5 beds, 3.5 baths

$2,475,000

5 beds3.5 baths— sq ft

12 Orchard Dr, Woodbury, NY 11797

Listing by Nest Seekers LLC

Property at 68 Mccouns Ln, Oyster Bay, NY 11771, 3 beds, 2 baths

$950,000

3 beds2 baths1,675 sq ft

68 Mccouns Ln, Oyster Bay, NY 11771

Listing by Daniel Gale Sothebys Intl Rlty

Property at 40 Park Way, Sea Cliff, NY 11579, 5 beds

$2,299,000

5 beds— baths2,982 sq ft

40 Park Way, Sea Cliff, NY 11579

Listing by Daniel Gale Sothebys Intl Rlty

Property at 20 Michaels Ln, Glen Head, NY 11545, 4 beds, 3 baths

$1,350,000

4 beds3 baths2,200 sq ft

20 Michaels Ln, Glen Head, NY 11545

Listing by Douglas Elliman Real Estate

Property at 21 Macarthur Ave, Plainview, NY 11803, 3 beds, 2 baths

$949,000

3 beds2 baths1,712 sq ft

21 Macarthur Ave, Plainview, NY 11803

Listing by Cornerstone Properties of LI

Property at 13 Garden Blvd, Hicksville, NY 11801, 5 beds, 4 baths

$1,138,000

5 beds4 baths2,100 sq ft

13 Garden Blvd, Hicksville, NY 11801

Listing by Douglas Elliman Real Estate

Property at 9 Briggs St, Hicksville, NY 11801, 5 beds, 4.5 baths

$1,598,000

5 beds4.5 baths3,085 sq ft

9 Briggs St, Hicksville, NY 11801

Listing by Douglas Elliman Real Estate

Property at 2 Blueberry Ln, Hicksville, NY 11801, 5 beds, 5 baths

$1,699,999

5 beds5 baths3,400 sq ft

2 Blueberry Ln, Hicksville, NY 11801

Listing by Property Professionals Realty

Property at 4530 Merrick Rd, Massapequa, NY 11758, 4 beds, 3 baths

$2,050,000

4 beds3 baths3,485 sq ft

4530 Merrick Rd, Massapequa, NY 11758

Listing by Signature Premier Properties

Property at 9 Hillside Ave, Glen Head, NY 11545, 4 beds, 1 bath

$928,000

4 beds1 bath1,846 sq ft

9 Hillside Ave, Glen Head, NY 11545

Listing by B Square Realty

Property at 105 7th St, Hicksville, NY 11801, 4 beds, 2 baths

$899,999

4 beds2 baths1,672 sq ft

105 7th St, Hicksville, NY 11801

Listing by Keller Williams Realty Elite

Property at 18304 Aspenwood Dr #239, Plainview, NY 11803, 2 beds, 2.5 baths

$1,600,000

2 beds2.5 baths1,976 sq ft

18304 Aspenwood Dr #239, Plainview, NY 11803

Listing by Realty Connect USA LLC

Property at 2 Mountain Ave, Bayville, NY 11709, 4 beds, 2.5 baths

$985,000

4 beds2.5 baths2,466 sq ft

2 Mountain Ave, Bayville, NY 11709

Listing by Branch Real Estate Group

Property at 141 Old Cedar Swamp Rd, Jericho, NY 11753, 6 beds, 5.5 baths

$2,950,000

6 beds5.5 baths4,500 sq ft

141 Old Cedar Swamp Rd, Jericho, NY 11753

Listing by Douglas Elliman Real Estate

Property at 4 Norgate Rd, Glen Head, NY 11545, 5 beds, 3.5 baths

$2,480,000

5 beds3.5 baths3,959 sq ft

4 Norgate Rd, Glen Head, NY 11545

Listing by United Real Estate Fortune

Property at 2 Buckingham Ct, Syosset, NY 11791, 5 beds, 5.5 baths

$3,995,000

5 beds5.5 baths6,000 sq ft

2 Buckingham Ct, Syosset, NY 11791

Listing by Compass Greater NY LLC

Property at 7 Judith St, Plainview, NY 11803, 4 beds, 2.5 baths

$1,188,000

4 beds2.5 baths2,029 sq ft

7 Judith St, Plainview, NY 11803

Listing by Signature Premier Properties

Property at 61 Riviera Dr S, Massapequa, NY 11758, 4 beds, 2.5 baths

$1,195,000

4 beds2.5 baths2,134 sq ft

61 Riviera Dr S, Massapequa, NY 11758

Listing by Blackstone Realty

Property at 135 Ocean Ave, Massapequa, NY 11758, 4 beds, 3 baths

$1,649,900

4 beds3 baths2,855 sq ft

135 Ocean Ave, Massapequa, NY 11758

Listing by Real Broker NY LLC

Property at 95 Woodlake Dr W #95, Woodbury, NY 11797, 3 beds, 2.5 baths

$920,000

3 beds2.5 baths1,958 sq ft

95 Woodlake Dr W #95, Woodbury, NY 11797

Listing by Coldwell Banker American Homes

Property at 300 Ellen Pl, Jericho, NY 11753, 5 beds, 4 baths

$1,599,888

5 beds4 baths3,228 sq ft

300 Ellen Pl, Jericho, NY 11753

Listing by Daniel Gale Sothebys Intl Rlty

Property at 5 Schoolhouse Ct, Oyster Bay, NY 11771, 5 beds, 6 baths

$2,499,000

5 beds6 baths6,816 sq ft

5 Schoolhouse Ct, Oyster Bay, NY 11771

Listing by Douglas Elliman Real Estate

Property at 70 Avery Rd, Woodbury, NY 11797, 5 beds, 3.5 baths

$1,888,888

5 beds3.5 baths2,599 sq ft

70 Avery Rd, Woodbury, NY 11797

Listing by ZI Realty LLC

Property at 25 Hitching Post Ln, Glen Cove, NY 11542, 4 beds, 3 baths

$999,000

4 beds3 baths2,349 sq ft

25 Hitching Post Ln, Glen Cove, NY 11542

Listing by Redfin Real Estate

Property at 44 E End Ave, Hicksville, NY 11801, 4 beds, 4 baths

$1,175,000

4 beds4 baths2,200 sq ft

44 E End Ave, Hicksville, NY 11801

Listing by Compass Greater NY LLC

Property at 12 Flo Dr, Syosset, NY 11791, 6 beds, 3.5 baths

$1,699,000

6 beds3.5 baths3,043 sq ft

12 Flo Dr, Syosset, NY 11791

Listing by Daniel Gale Sothebys Intl Rlty

Property at 4 Greenway Dr, Syosset, NY 11791, 4 beds, 2 baths

$989,000

4 beds2 baths1,865 sq ft

4 Greenway Dr, Syosset, NY 11791

Listing by Engel & Volkers North Fork

Property at 9 Beatrice Ln, Glen Cove, NY 11542, 4 beds, 2.5 baths

$1,400,000

4 beds2.5 baths2,605 sq ft

9 Beatrice Ln, Glen Cove, NY 11542

Listing by Houlihan Lawrence Inc.

Property at 5 Edward Ave, Hicksville, NY 11801, 4 beds, 3 baths

$999,000

4 beds3 baths2,188 sq ft

5 Edward Ave, Hicksville, NY 11801

Listing by Voro LLC

Property at 2 Coolidge Ave Unit T, Glen Head, NY 11545, 4 beds, 3 baths

$1,650,000

4 beds3 baths2,982 sq ft

2 Coolidge Ave Unit T, Glen Head, NY 11545

Listing by Douglas Elliman Real Estate

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Based on information submitted to the MLS GRID as of Sat Dec 06 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Luxury Homes for Sale in Oyster Bay

There are currently 389 luxury homes for sale in Oyster Bay at a median listing price of $1.09M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oyster Bay stay on the market for 64 days and receive 6 offers. Popular neighborhoods include Douglaston, North Shore Towers & Country Club, Glen Oaks, Queens, and Long Island. This map is refreshed with the newest listings in Oyster Bay every 15 minutes.

In the past month, 203 homes have been sold in Oyster Bay. In addition to houses in Oyster Bay, there were also 51 condos, 1 townhouse, and 13 multi-family units for sale in Oyster Bay last month. Find your dream home in Oyster Bay using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oyster Bay are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oyster Bay. If you're looking to sell your home in the Oyster Bay area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oyster Bay with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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