Glen Head, NY Homes

/29
$6,499,000
- 6 Beds
- 5.5 Baths
89 Pound Hollow Rd, Glen Head, NY 11545

Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable.From the moment you step inside, you’re swept into a world of high style and high impact. The

Karen Sharf Daniel Gale Sothebys Intl Rlty

89 Pound Hollow Rd, Glen Head, NY 11545
$1,750,000 Sold Jul 21, 2025
- 5,485 Sq Ft
- $319/SF
- 170 Days On Market
- 6 Beds
- 5.5 Baths
- Built 2006
277 Piping Rock Rd, Locust Valley, NY 11560

Stunning 6-Bedroom Home on Piping Rock Road, Locust Valley. Welcome to your dream home! Nestled on the serene Piping Rock Road in Locust Valley, this expansive 13-room residence offers an unparalleled blend of elegance and comfort. With six spacious bedrooms and five full baths plus a half bath, this home is designed for both relaxation and entertaining. The soaring ten-foot ceilings create an

James Clark Signature Premier Properties

277 Piping Rock Rd, Locust Valley, NY 11560

Est $1,179,032 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,626 Sq Ft
3 Tennis Ct, Glen Head, NY 11545

3 Tennis Ct, Glen Head, NY 11545

/12
$15,000,000
2340 Cedar Swamp Rd, Glen Head, NY 11545

Brookville | On the market for the first time in over a century, welcome to 2340 Cedar Swamp Road - a once-in-a-lifetime opportunity to own an estate in the heart of Long Island's Gold Coast. This property, totaling a near 52-acres of undeveloped land, was once home to the Joan of Arc Chapel - a small chapel imported by Gertrude Hill Gavin, daughter of railway director, James Jerome Hill. It was

Joe Scavo Douglas Elliman Real Estate

2340 Cedar Swamp Rd, Glen Head, NY 11545
$790,000 Sold Jul 15, 2025
- 1,660 Sq Ft
- $476/SF
- 29 Days On Market
- 3 Beds
- 1 Bath
- Built 1920
4 Hillcrest Dr, Glen Head, NY 11545

Nestled in the charming Community of Glen Head on Long Island's North Shore, this original 1920 expanded Cape offers timeless character with modern potential. The home features a spacious living room, dining area, and a cozy sunken den perfect for relaxing. A first-floor bedroom and full bath provide convenience and flexibility, while the oversized yard offers ample space for outdoor enjoyment

Amy Tansill Daniel Gale Sothebys Intl Rlty

4 Hillcrest Dr, Glen Head, NY 11545

Est $2,822,451 Not Listed For Sale
- 5 Beds
- 6 Baths
- 5,532 Sq Ft
13 Beechwood Dr, Glen Head, NY 11545

13 Beechwood Dr, Glen Head, NY 11545

/11
$15,000,000
- Land
- 51.6 Acres
- $290,698 per Acre
2340 A Cedar Swamp Rd, Glen Head, NY 11545

Brookville | On the market for the first time in over a century, welcome to 2340 Cedar Swamp Road - a once-in-a-lifetime opportunity to own a historical estate in the heart of Long Island's Gold Coast. This property, totaling a near 52-acres of undeveloped land, was once home to the Joan of Arc Chapel - a small chapel imported by Gertrude Hill Gavin, daughter of railway director, James Jerome

Joe Scavo Douglas Elliman Real Estate

2340 A Cedar Swamp Rd, Glen Head, NY 11545
$2,500,000 Sold Jul 15, 2025
- 5,470 Sq Ft
- $457/SF
- 11 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1981
12 Shelter Ln, Glen Head, NY 11545

Located at the end of a beautiful tree-lined private cul-de-sac, this Upper Brookville contemporary David Chotan built home in Upper Brookville sits on over 2.5 acres and offers a luxurious, sunlit retreat designed for entertaining. The grand foyer opens to an expansive layout featuring a sunken living room with a built-in wet bar, fireplace, soaring ceilings, and floor-to-ceiling windows. All

Melanie Cogan Compass Greater NY LLC

12 Shelter Ln, Glen Head, NY 11545

Est $1,035,481 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,643 Sq Ft
3 Central Dr, Glen Head, NY 11545

3 Central Dr, Glen Head, NY 11545

/27
$3,699,000
- 5 Beds
- 4.5 Baths
5 Peacock Ln, Glen Head, NY 11545

Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with

Peggy Carillo Douglas Elliman Real Estate

5 Peacock Ln, Glen Head, NY 11545
$4,100,000 Sold Jul 11, 2025
- 7,000 Sq Ft
- $586/SF
- 10 Days On Market
- 6 Beds
- 5.5 Baths
- Built 2005
1 Peacock Ln, Glen Head, NY 11545

Gated, Private Brick Manor Home situated on 2.32 acres of beautifully manicured lawns and gardens. The property is located on the prestigious and highly coveted Peacock Lane in the sought after North Shore Village of Upper Brookville. This Architectural Masterpiece is unparallel for its luxury, amenities and attention to details.The private 2.32 acre Estate is graced with the expansive circular

Diana Hiotis BERKSHIRE HATHAWAY

1 Peacock Ln, Glen Head, NY 11545

Est $912,047 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
8 Terry Ct, Glen Head, NY 11545

8 Terry Ct, Glen Head, NY 11545

/34
$14,900,000
- 7 Beds
- 9 Baths
1985- 4 Cedar Swamp Rd, Glen Head, NY 11545

'Haut Bois' - is an elegant brick and stucco French Chateau located in the heart of Brookville, NY. Drawing inspiration from the Louis XIV Hunting Lodge, now known as the Palace At Versailles, this stunning 18 room estate is rich in history and beauty. Originally built by Ogden Codman Jr. in 1916 and later restored in the late 1900's and also in 2023, this one-of-a-kind masterpiece stands tall at

Jason Friedman Daniel Gale Sothebys Intl Rlty

1985- 4 Cedar Swamp Rd, Glen Head, NY 11545
$2,801,000 Sold Jul 09, 2025
- 5,732 Sq Ft
- $489/SF
- 45 Days On Market
- 6 Beds
- 7.5 Baths
- Built 1984
4 Paddock Ct, Glen Head, NY 11545

Welcome to a life of luxury - Nestled on a meticulously landscaped 2.1-acre lot in a peaceful cul-de-sac at Glen Head, this beautifully contemporary home offers the perfect blend of luxury and comfort. Upon entering, you're welcomed by a grand two-story great room with expansive glass sliding doors leading out to a spacious back deck, providing stunning views of the vast backyard. The left wing

Michelle Zhao ZI Realty LLC

4 Paddock Ct, Glen Head, NY 11545

Est $1,134,407 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,289 Sq Ft
20 Terry Ct, Glen Head, NY 11545

20 Terry Ct, Glen Head, NY 11545

/16
$6,000,000
- 4 Beds
- 3.5 Baths
- 4,285 Sq Ft
156 Brookville Rd, Glen Head, NY 11545

Imagine the most incredible, private setting you can think of... well here it is. Three gorgeous acres set far off the main road. Koi ponds, beautiful landscaping, green grass and trees as far as the eye can see. All of this surrounded by 300 acres of town preserve land. This contemporary home has 4 bedrooms, incredible high ceilings, spacious rooms and tons of natural light. One of a kind

Melissa Kaminsky Julia B Fee Sothebys Int. Rlty

156 Brookville Rd, Glen Head, NY 11545
$1,600,000 Sold Jul 01, 2025
- 2,978 Sq Ft
- $537/SF
- 16 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1993
41 William St, Glen Head, NY 11545

A must see!!! This beautifully maintained colonial home offers an open and inviting floor plan, perfect for modern living. Enjoy seamless indoor-outdoor entertaining with an incredible backyard, complete with a heated saltwater pool, built in barbecue, an architectural stone patio with awnings for shade, surrounded with evergreen trees for complete privacy. Inside, you'll find 4 bedrooms, 3.5

John Langone Daniel Gale Sothebys Intl Rlty

41 William St, Glen Head, NY 11545

Est $1,747,296 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,985 Sq Ft
8 Cross Ln, Glen Head, NY 11545

8 Cross Ln, Glen Head, NY 11545

/15
$849,900 Pending
- 3 Beds
- 1.5 Baths
- 1,300 Sq Ft
16 Wagon Ln, Glen Head, NY 11545

Welcome to 16 Wagon Lane, a 3 bedroom, 1.5 bath Colonial tucked away in a cul de sac. This home offers a comfortable layout filled with natural light. The living areas flow seamlessly, creating an ideal setting for everyday living and entertaining. Enjoy the private backyard which is perfect for gardening or relaxing in a peaceful setting.

Lynda Torel Daniel Gale Sothebys Intl Rlty

16 Wagon Ln, Glen Head, NY 11545
$1,030,000 Sold Jun 30, 2025
- 2,140 Sq Ft
- $481/SF
- 9 Days On Market
- 5 Beds
- 4 Baths
- Built 1951
14 Washington Ave, Glen Head, NY 11545

Welcome to this sunny, spacious, 5-bedroom, 4-bath home in a perfect mid-block location in the sought-after Hill Terrace section of Glen Head. Enter through the charming 2-door foyer into the living room, dining room, and kitchen. The first floor also includes a primary bedroom with a full bath and an additional bedroom and hallway bath. The second floor has an additional primary bedroom with a

Madeline Moritz Douglas Elliman Real Estate

14 Washington Ave, Glen Head, NY 11545

Est $2,395,781 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,600 Sq Ft
10 Central Dr, Glen Head, NY 11545

10 Central Dr, Glen Head, NY 11545

/25
$749,000 Pending
- 2 Beds
- 2 Baths
- 1,180 Sq Ft
5 Cody Ave, Glen Head, NY 11545

Pristine & Perfect!! Welcome to this Warm and Inviting Ranch!! Offers open floor plan with updated Kitchen, Quartz Counter Tops, Stainless Steel Appliances, Huge Bay Window offering natural light, Dining Area, Large Living Room, Harwood Floors, Moldings, Primary Suite with Walk in Closet and Primary Bath with heated floors, Additional Bedroom with huge closet and hardwood floors, Updated Full

Mishelle Berger Calo Compass Greater NY LLC

5 Cody Ave, Glen Head, NY 11545
$3,359,999 Sold Jun 27, 2025
- 45 Days On Market
- 6 Beds
- 5.5 Baths
- Built 1964
77 Linden Ln, Glen Head, NY 11545

Nestled on a 2.1 -acre beautifully landscaped property, this six-bedroom, five-and-a half bath home offers an unparalleled blend of modern luxury and timeless charm. Completely renovated in 2024, it features a large living room and den, both with wood-burning fireplaces and expansive windows offering stunning views of the vast property. The eat-in kitchen is a chef's delight, equipped with

Debra Quinn Petkanas Daniel Gale Sothebys Intl Rlty

77 Linden Ln, Glen Head, NY 11545

Est $2,064,343 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,100 Sq Ft
9 Central Dr, Glen Head, NY 11545

9 Central Dr, Glen Head, NY 11545

/49
$3,449,000 Pending
- 6 Beds
- 5 Baths
- 5,500 Sq Ft
13 Locust Ln, Glen Head, NY 11545

La Isabella : A Gracious 2 Acre Estate In Prestigious Upper Brookville Offering Timeless Colonial Architecture With Modern Luxury. Set Behind A Sweeping Drive And Surrounded By Mature Magnolia, Dogwood, And Maple Trees, This Home Is Crafted For Multigenerational Living With Privacy And Sophistication. Inside, A Dramatic Double-Height Foyer And Sweeping Staircase Welcome You To Spacious Sunlit

Lisa Fasano Compass Greater NY LLC

13 Locust Ln, Glen Head, NY 11545
$2,350,000 Sold Jun 26, 2025
- 4,644 Sq Ft
- $506/SF
- 178 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1979
30 Glenby Ln, Glen Head, NY 11545

This stunning 4,600-square-foot French inspired masterpiece boasts 5 bedrooms and 4.5 baths, perfectly blending elegance and comfort. As you step into the grand 2-story foyer, you'll find a spacious living room featuring a charming fireplace, a formal dining room ideal for special occasions, and a welcoming family room with a double-sided fireplace that seamlessly connects to a large eat-in

Shawn Elliott Nest Seekers LLC

30 Glenby Ln, Glen Head, NY 11545

Est $1,012,939 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,704 Sq Ft
17 Glen Ln, Glen Head, NY 11545

17 Glen Ln, Glen Head, NY 11545

/20
$835,000 Pending
- 4 Beds
- 2 Baths
- 2,036 Sq Ft
1 William St, Glen Head, NY 11545

Single-family “Cape” style home. The property contains 2,036+square spread over 3 levels, including a finished basement with interior and exterior access. The home is frame/brick construction with asphalt shingle roof, cedar shingles siding and double hung aluminum windows. The home consists of bedrooms, two full bathrooms, a kitchen with original appliances and a living room with an arched entry

Kerry Ann Fyne Citizens International Realty

1 William St, Glen Head, NY 11545
$1,295,000 Sold Jun 24, 2025
- 1,900 Sq Ft
- $682/SF
- 12 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1951
16 Bryant Rd, Glen Cove, NY 11542

A flawless gem. Fully renovated in 2022, this home defines move-in ready! Upon entry you will enjoy a thoughtfully open floor plan with stunning white kitchen, quartz countertops & premium stainless steel appliances. Flooded with natural light, this combined living and dining space flows perfectly for entertaining with easy access to the resort-style backyard. Completing the main floor is a

Lauren Grella Daniel Gale Sothebys Intl Rlty

16 Bryant Rd, Glen Cove, NY 11542

Est $806,361 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,831 Sq Ft
13 Glen Cove Dr, Glen Head, NY 11545

13 Glen Cove Dr, Glen Head, NY 11545

/29
$2,275,000 Pending
- 3 Beds
- 4 Baths
- 3,602 Sq Ft
183 Linden Ln, Glen Head, NY 11545

Sophisticated Colonial set on two flat, beautifully landscaped acres, offering the best of modern luxury and timeless elegance. Built in 2016, this custom home features an ideal floor plan designed for today’s lifestyle. The main level boasts a Ken Kelly–designed kitchen with premium appliances, a spacious dining area, and a comfortable family room centered around a gas fireplace. A formal living

Alexis Mcandrew Daniel Gale Sothebys Intl Rlty

183 Linden Ln, Glen Head, NY 11545
$4,800,000 Sold Jun 24, 2025
- 7,000 Sq Ft
- $686/SF
- 83 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2006
6 Wenwood Dr, Glen Head, NY 11545

This exquisite Hampton Colonial-style home sits nestled on over 2 manicured acres in prestigious Brookville. With more than 7,000 square feet of meticulously designed living space, this exceptional estate blends classic architecture with contemporary amenities. The grand two-story foyer features distinctive herringbone hardwood floors, setting the tone for the sophisticated open-concept layout

Zach Elliott Nest Seekers LLC

6 Wenwood Dr, Glen Head, NY 11545

Est $682,591 Not Listed For Sale
- 3 Beds
- 1 Bath
- 960 Sq Ft
1 Maiden Ln, Glen Head, NY 11545

1 Maiden Ln, Glen Head, NY 11545

/42
$1,599,000 Pending
- 5 Beds
- 3.5 Baths
- 2,957 Sq Ft
18 Knoll Ln, Glen Head, NY 11545

Welcome to luxury living in Glen Head. This meticulously maintained colonial spans nearly 3,000 sq ft and blends modern comfort with timeless style. Featuring 4 spacious bedrooms, 3.5 baths, and an option for a 5th bedroom. The chef’s kitchen offers radiant heated floors, Sub-Zero refrigerator, Thermador oven, and opens to a bright breakfast area. The den features a wood-burning fireplace, custom

Raquel Knoell Douglas Elliman Real Estate

18 Knoll Ln, Glen Head, NY 11545
$999,000 Sold Jun 23, 2025
- 13 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
65 The Cir Unit 65, Glen Head, NY 11545

A rare opportunity awaits in the gated community of The Knolls—welcome to the largest and most desirable corner unit, offering privacy, space, and beautiful natural light throughout. This bright and expansive home boasts a grand entry foyer that sets the tone for the elegant design, seamlessly flowing into both the main and lower living spaces—ideal for everyday comfort and stylish entertaining.

Sandi Lefkowitz Daniel Gale Sothebys Intl Rlty

65 The Cir Unit 65, Glen Head, NY 11545

Est $798,330 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,409 Sq Ft
5 Maiden Ln, Glen Head, NY 11545

5 Maiden Ln, Glen Head, NY 11545

/50
$2,000,000 Pending
- 4 Beds
- 5 Baths
- 3,628 Sq Ft
10 Eastview Ln, Glen Head, NY 11545

Heritage lives beautifully in this one-of-a-kind residence where timeless architecture and refined design bring both grace and nostalgia. Set on a private, tree-lined lot, the home offers four bedrooms, three full bathrooms, and two half-baths, along with a sun-filled kitchen featuring a wood-burning fireplace, a formal library, music room, office, and a fully finished basement. The grounds are

Catherine Davis Serhant East End LLC

10 Eastview Ln, Glen Head, NY 11545
$2,275,000 Sold Jun 23, 2025
- 3,658 Sq Ft
- $622/SF
- 117 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1975
37 Linden Ln, Glen Head, NY 11545

Perfectly located in the coveted North Shore community of Old Brookville this 5 bedroom 4 bath colonial awaits your finishing touch. This colonial home sits proudly on expansive level 2 acre lot. Many updates have been added to the home including 3 newly renovated baths with custom fixtures and radiant heat tastefully designed for today's lifestyle. The home includes formal living and dining

Laura Algios Daniel Gale Sothebys Intl Rlty

37 Linden Ln, Glen Head, NY 11545

Est $1,153,861 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,625 Sq Ft
11 Oak Valley Dr, Glen Head, NY 11545

11 Oak Valley Dr, Glen Head, NY 11545

/19
$1,699,000 Pending
- 6 Beds
- 4 Baths
- 3,416 Sq Ft
270 Frost Pond Rd, Glen Head, NY 11545

A versatile and desirable property located in the Village of Old Brookville, NY. This colonial style house is positioned on 2.138 level acres, all flat and usable, providing space for recreation, expansion or future customization. A separate structure oversized concrete garage with high ceilings can be accessed by a long driveway in from the road. Bring your vision to renovate this 6 bedroom

Michael Stanco Compass Greater NY LLC

270 Frost Pond Rd, Glen Head, NY 11545

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