Upper Brookville, NY Homes

/41
$3,795,000
- 6 Beds
- 5.5 Baths
- 5,911 Sq Ft
23 Overbrook Ln, Glen Head, NY 11545

Framed by sweeping pond views and surrounded by over 2 private acres of beautifully landscaped grounds, this beautifully renovated brick estate offers a rare blend of luxury, privacy, and serene waterfront living. Tucked away on a quiet cul-de-sac, the home is perfectly positioned to capture the beauty of the pond from both the interior living spaces and the resort-style outdoor setting.A

Jagmeet Bedi

Compass Greater NY LLC

23 Overbrook Ln, Glen Head, NY 11545
Explore Upper Brookville
/38
$8,500 Per Month
- 5 Beds
- 3.5 Baths
- 2,968 Sq Ft
- House for Rent
5 Linda Ct, Oyster Bay, NY 11771

A Private Cul-de-Sac Home in Upper Brookville Backing Golf CourseTucked away at the end of a long private driveway, this well-positioned residence offers exceptional privacy on a coveted cul-de-sac and overlooks a scenic golf course. Built in 1962, the home features 5 bedrooms and 3.5 baths across approximately 2,968 square feet of living space.Landscaping, Grounds and at landlord's

Giulio Ferrante

Signature Premier Properties

5 Linda Ct, Oyster Bay, NY 11771
$3,000,000

Sold Mar 27, 2026

1347 Chicken Valley Rd, Oyster Bay, NY 11771
- 4 Beds
- 5 Baths
- 3,683 Sq Ft
- Built 1928
Last Sold Summary
- 8% Below List Price
- $815/SF
- 44 Days On Market
Current Estimated Value $3,008,324

Last Listing Agent Kimberly Bancroft Daniel Gale Sothebys Intl Rlty

1347 Chicken Valley Rd, Oyster Bay, NY 11771

Est $3,539,865

Not Listed For Sale

77 Linden Ln, Glen Head, NY 11545
- 6 Beds
- 5.5 Baths
- 5,732 Sq Ft
- Built 1964
77 Linden Ln, Glen Head, NY 11545

Last Sold Summary
- 45 Days On Market
Last Listing Agent Debra Quinn Petkanas Daniel Gale Sothebys Intl Rlty

/49
$8,995,000

$2M PRICE DROP
- 6 Beds
- 10 Baths
- 10,109 Sq Ft
31 Chestnut Hill Dr, Oyster Bay, NY 11771

Maison Blanche: An Architectural Icon in Upper BrookvilleExperience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated

Ephraim Simon

Serhant East End LLC

31 Chestnut Hill Dr, Oyster Bay, NY 11771
/30
$10,000 Per Month
- 6 Beds
- 4.5 Baths
- 3,031 Sq Ft
- House for Rent
1719 Cedar Swamp Rd, Glen Head, NY 11545

Welcome to an Extraordinary Rental opportunity where Privacy, Space, and Luxury converge. Set on approximately 2.5 acres of Lush Manicured Grounds, this stunning 3,000+ sqft Expanded Ranch offers an Unmatched Living Experience within the Prestigious Jericho School District. From the moment you turn down the long, Private Driveway, you know this home is something special. Featuring 6 Spacious

George Gatt Stephen Joseph Properties

1719 Cedar Swamp Rd, Glen Head, NY 11545
$2,400,000

Sold Feb 10, 2026

40 W View Dr, Oyster Bay, NY 11771
- 5 Beds
- 5.5 Baths
- 6,219 Sq Ft
- Built 1987
Last Sold Summary
- 3% Below List Price
- $386/SF
- 21 Days On Market
Current Estimated Value $2,496,132

Last Listing Agent Barbara Drucker Douglas Elliman Real Estate

40 W View Dr, Oyster Bay, NY 11771

Est $2,918,730

Not Listed For Sale

67 Mill River Rd, Oyster Bay, NY 11771
- 6 Beds
- 8 Baths
- 5,699 Sq Ft
- Built 2014
67 Mill River Rd, Oyster Bay, NY 11771

Last Sold Summary
- 255 Days On Market
Last Listing Agent John Messina Daniel Gale Sothebys Intl Rlty

/47
$25,000,000
- 13 Beds
- 17 Baths
- 22,429 Sq Ft
1 Applewood Estate, Upper Brookville, NY 11545

Experience Applewood Estate — a generational North Shore compound where timeless architecture, historic provenance, and resort-caliber living unfold across more than 35 secluded acres in the esteemed Village of Upper Brookville. Once an operating apple orchard in the early 1900s and later owned by renowned American artist Montague Flagg, this extraordinary estate carries a legacy as rich as the

Ephraim Simon

Serhant East End LLC

1 Applewood Estate, Upper Brookville, NY 11545
/21
$3,400 Per Month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Apartment for Rent
Unlisted Address

A long driveway leads up to a secluded, hilltop cottage, freshly painted, hardwood floors throughout, high ceilings, washer, dryer on premises.There is private parking with lovely grounds.; quiet and serene. The cottage is ground level with no stairs.This is very special!

Donna Scala LAFFEY REAL ESTATE

Unlisted Address
$2,700,000

Sold Feb 24, 2026

183 Linden Ln, Glen Head, NY 11545
- 3 Beds
- 4 Baths
- 3,602 Sq Ft
- Built 2016
Last Sold Summary
- 19% Above List Price
- $750/SF
- 9 Days On Market
Current Estimated Value $2,612,121

Last Listing Agent Alexis Mcandrew Daniel Gale Sothebys Intl Rlty

183 Linden Ln, Glen Head, NY 11545

Not Listed For Sale

No # Linden Ln, Upper Brookville, NY 11545
No # Linden Ln, Upper Brookville, NY 11545

Last Sold Summary
- 82 Days On Market
Last Listing Agent Debra Quinn Petkanas Daniel Gale Sothebys Intl Rlty

/35
$9,750,000

Pending
- 7 Beds
- 14 Baths
- 11,926 Sq Ft
4 Red Fox Ln, Glen Head, NY 11545

Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a

Pierce Dellafera Daniel Gale Sothebys Intl Rlty

4 Red Fox Ln, Glen Head, NY 11545
/33
$16,500 Per Month
- 5 Beds
- 3.5 Baths
- 4,633 Sq Ft
- House for Rent
3 Farmwoods Ln, Glen Head, NY 11545

Gated Elegance in the Incorporated Village of Upper Brookville - Set inside a gated entrance to the street of fine homes, this beautifully renovated 5-bedroom, 3.5-bath Colonial offers a rare combination of turnkey luxury and resort-style outdoor living — all on 2 flat, park-like acres in the Locust Valley School District. Thoughtfully updated throughout, the home features new windows, new

Neena Chowdhary Daniel Gale Sothebys Intl Rlty

3 Farmwoods Ln, Glen Head, NY 11545
$3,550,000

Sold May 08, 2026

5 Peacock Ln, Glen Head, NY 11545
- 5 Beds
- 4.5 Baths
- 4,816 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $737/SF
- 502 Days On Market
Current Estimated Value $3,378,949

Last Listing Agent Peggy Carillo Douglas Elliman Real Estate

5 Peacock Ln, Glen Head, NY 11545

Est $2,789,202

Not Listed For Sale

999 Wolver Hollow Rd, Oyster Bay, NY 11771
- 6 Beds
- 4.5 Baths
- 6,595 Sq Ft
- Built 1958
999 Wolver Hollow Rd, Oyster Bay, NY 11771

Last Sold Summary
- 15 Days On Market
Last Listing Agent Lindsey Barnett Compass Greater NY LLC

/39
$2,988,000

Pending
- 6 Beds
- 4.5 Baths
- 5,000 Sq Ft
110 Linden Ln, Glen Head, NY 11545

Welcome to luxury living in Upper Brookville's most desirable location. This stunning furnished residence features 6 bedrooms, 5 bathrooms, an office, and a luxurious master suite with a steam shower, jacuzzi tub and a huge walk-in closet. Spread across beautifully landscaped grounds, enjoy amenities such as a Har-Tru tennis court, a heated Olympic-size pool with a spa, and a sun filled deck with

Cassandra DiPietro F2 Firm Inc

110 Linden Ln, Glen Head, NY 11545
$3,900,000

Sold Jun 15, 2026

51 Linden Ln, Glen Head, NY 11545
- 5 Beds
- 4.5 Baths
- 4,934 Sq Ft
- Built 1951
Last Sold Summary
- 4% Above List Price
- $790/SF
- 21 Days On Market
Current Estimated Value $3,811,056

Last Listing Agent Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

51 Linden Ln, Glen Head, NY 11545

Est $2,314,654

Not Listed For Sale

22 W View Dr, Oyster Bay, NY 11771
- 5 Beds
- 4.5 Baths
- 5,187 Sq Ft
- Built 1987
22 W View Dr, Oyster Bay, NY 11771

Last Sold Summary
- 96 Days On Market
Last Listing Agent Jasleen Sabharwal Douglas Elliman Real Estate

/50
$1,895,000

$100K PRICE DROP Pending
- 5 Beds
- 4.5 Baths
- 3,938 Sq Ft
195 Cedar Swamp Rd, Glen Head, NY 11545

A Rare 2-Acre North Shore Estate-Like Setting Offering Privacy, Presence, and Endless Potential Set on approximately 2 acres of private, park-Like grounds, this timeless Colonial with vintage charm presents a truly rare opportunity in the heart of Glen Head. Privately set back and gently elevated from the road along a long, tree-lined approach, the property offers an exceptional sense of space

Nicole Commisso OverSouth LLC

195 Cedar Swamp Rd, Glen Head, NY 11545
$2,200,000

Sold Mar 19, 2026

21 Overbrook Ln, Glen Head, NY 11545
- 6 Beds
- 4.5 Baths
- 5,900 Sq Ft
- Built 1992
Last Sold Summary
- 2% Below List Price
- $373/SF
- 75 Days On Market
Current Estimated Value $2,795,997

Last Listing Agent Dalia Elison Douglas Elliman Real Estate

21 Overbrook Ln, Glen Head, NY 11545

Est $922,092

Not Listed For Sale

25 Derby Ct, Oyster Bay, NY 11771
- 3 Beds
- 3 Baths
- 1,917 Sq Ft
- Built 1982
25 Derby Ct, Oyster Bay, NY 11771

Last Sold Summary
- 12 Days On Market
Last Listing Agent Laura Cochran BERKSHIRE HATHAWAY

/43
$1,980,000

Pending
- 4 Beds
- 3 Baths
- 2,917 Sq Ft
279 Hillcrest Ln, Oyster Bay, NY 11771

Welcome to 279 Hillcrest Lane — A Rare Gold Coast Retreat on Over 2 Private AcresNestled in the prestigious Village of Upper Brookville on New York's storied North Shore, 279 Hillcrest Lane is a beautifully updated modified ranch offering the perfect blend of timeless elegance, thoughtful modern upgrades, and exceptional outdoor living. Set on over 2 park-like acres (87,133 sq ft) of lush,

Huailing Deng Daniel Gale Sothebys Intl Rlty

279 Hillcrest Ln, Oyster Bay, NY 11771
$2,300,000

Sold Oct 08, 2025

199 Terrace Ln, Oyster Bay, NY 11771
- 5 Beds
- 5 Baths
- 6,300 Sq Ft
- Built 1932
Last Sold Summary
- 14% Below List Price
- $365/SF
- 91 Days On Market
Current Estimated Value $3,192,000

Last Listing Agent Huailing Deng Daniel Gale Sothebys Intl Rlty

199 Terrace Ln, Oyster Bay, NY 11771

Est $5,754,315

Not Listed For Sale

3 Donna Dr, Oyster Bay, NY 11771
- 6 Beds
- 9 Baths
- 7,000 Sq Ft
- Built 2024
3 Donna Dr, Oyster Bay, NY 11771

Last Sold Summary
- 578 Days On Market
Last Listing Agent Tracey Murray Kupferberg Douglas Elliman Real Estate

/38
$2,895,000
- 4 Beds
- 5 Baths
- 3,200 Sq Ft
1017 Friendly Rd, Oyster Bay, NY 11771

UPPER BROOKVILLE. Privately set behind sweeping lawns on over two acres in the Village of Upper Brookville, this elegant North Shore residence offers the privacy, scale, and timeless character synonymous with Gold Coast estate living. The home features 4 bedrooms, with primary suite on the main, and 3 full and 2 half baths, along with sun-filled living spaces, hardwood and tiled (radiant heated)

Maria Babaev Douglas Elliman Real Estate

1017 Friendly Rd, Oyster Bay, NY 11771
$3,300,000

Sold Mar 09, 2026

13 Locust Ln, Glen Head, NY 11545
- 6 Beds
- 5 Baths
- 5,500 Sq Ft
- Built 2012
Last Sold Summary
- 11% Below List Price
- $600/SF
- 143 Days On Market
Current Estimated Value $3,515,159

Last Listing Agent Lisa Fasano Compass Greater NY LLC

13 Locust Ln, Glen Head, NY 11545

Est $5,894,176

Not Listed For Sale

353 Juniper Dr, Oyster Bay, NY 11771
- 6 Beds
- 9 Baths
- 11,200 Sq Ft
- Built 2013
353 Juniper Dr, Oyster Bay, NY 11771

Last Sold Summary
- 278 Days On Market
Last Listing Agent Jason Friedman Daniel Gale Sothebys Intl Rlty

/45
$3,500,000

$300K PRICE DROP
- 5 Beds
- 4.5 Baths
- 4,528 Sq Ft
61 Linden Ln, Glen Head, NY 11545

Dream homes do exist. Perfectly situated on 2+ private, meticulously landscaped acres on a winding country lane, this charming 5-bedroom residence offers an unparalleled lifestyle. Every sun-drenched room provides stunning, expansive views of lush lawns, specimen trees, and vibrant perennial gardens. Exquisite Craftsmanship & Main Level Living. The main level showcases exceptional millwork, fine

Kathryn Maxwell Pournaras Daniel Gale Sothebys Intl Rlty

61 Linden Ln, Glen Head, NY 11545
$2,450,000

Sold Sep 12, 2025

363 Juniper Dr, Oyster Bay, NY 11771
- 5 Beds
- 3.5 Baths
- 4,067 Sq Ft
- Built 1962
Last Sold Summary
- 2% Above List Price
- $602/SF
- 11 Days On Market
Current Estimated Value $2,531,687

Last Listing Agent Paula Handler LAFFEY REAL ESTATE

363 Juniper Dr, Oyster Bay, NY 11771

Est $8,785,634

Not Listed For Sale

43 Chestnut Hill Dr, Oyster Bay, NY 11771
- 7 Beds
- 13 Baths
- 10,861 Sq Ft
- Built 1993
43 Chestnut Hill Dr, Oyster Bay, NY 11771

Last Sold Summary
- 19 Days On Market
Last Listing Agent Shawn Elliott Nest Seekers LLC

/49
$5,599,000

Open Sun 12:30PM - 3PM
- 6 Beds
- 6.5 Baths
- 7,300 Sq Ft
730 Remsens Ln, Oyster Bay, NY 11771

Introducing an Extraordinary new Construction Estate in the prestigious Village of Muttontown, Set on approximately 3 Private acres overlooking a Picturesque Golf Couse. This Exceptional 2026 built residence offers the perfect blend of Modern Luxury , Elegance, and Sophistication.Featuring Six (6) Spacious Bedrooms and 6.5 designer bathrooms, with Radiant Heated Floors. The home showcases

Maria Priovolos Keller Williams Points North

730 Remsens Ln, Oyster Bay, NY 11771
$1,800,000

Sold May 25, 2026

111 Mill River Rd, Oyster Bay, NY 11771
- 5 Beds
- 3 Baths
- 4,000 Sq Ft
- Built 1962
Last Sold Summary
- 6% Below List Price
- $450/SF
- 27 Days On Market
Current Estimated Value $1,863,861

Last Listing Agent Rosalinda Silver Blackstone Realty

111 Mill River Rd, Oyster Bay, NY 11771

Est $2,238,102

Not Listed For Sale

959 Ripley Ln, Oyster Bay, NY 11771
- 5 Beds
- 4.5 Baths
- 3,892 Sq Ft
- Built 1978
959 Ripley Ln, Oyster Bay, NY 11771

Last Sold Summary
- 39 Days On Market
Last Listing Agent Linda Lugo Realty Masters North Shore

/22
$3,500,000
- 6 Beds
- 9 Baths
- 7,500 Sq Ft
5 Carol Ln, Glen Head, NY 11545

Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes

Ken Deutsch Deutsch Realty Inc

5 Carol Ln, Glen Head, NY 11545
$1,710,000

Sold Oct 17, 2025

2 W View Dr, Oyster Bay, NY 11771
- 5 Beds
- 5.5 Baths
- 5,625 Sq Ft
- Built 1987
Last Sold Summary
- 8% Below List Price
- $304/SF
- 30 Days On Market
Current Estimated Value $1,926,097

Last Listing Agent Lois Kirschenbaum Daniel Gale Sothebys Intl Rlty

2 W View Dr, Oyster Bay, NY 11771

Est $4,054,540

Not Listed For Sale

963 Ripley Ln, Oyster Bay, NY 11771
- 7 Beds
- 8 Baths
- 7,493 Sq Ft
- Built 1925
963 Ripley Ln, Oyster Bay, NY 11771

Last Sold Summary
- 240 Days On Market
Last Listing Agent Kathryn Zoller Daniel Gale Sothebys Intl Rlty

/37
$4,998,000

$290K PRICE DROP
- 6 Beds
- 6.5 Baths
- 7,111 Sq Ft
7 Fairway Ct, Oyster Bay, NY 11771

A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a

Michelle Cohen Compass Greater NY LLC

7 Fairway Ct, Oyster Bay, NY 11771
$2,500,000

Sold Sep 29, 2025

1039 Friendly Rd, Upper Brookville, NY 11771
- 6 Beds
- 4.5 Baths
- 3,529 Sq Ft
- Built 1958
Last Sold Summary
- 25% Above List Price
- $708/SF
- 8 Days On Market
Current Estimated Value $2,524,944

Last Listing Agent Lisa Lauricella Signature Premier Properties

1039 Friendly Rd, Upper Brookville, NY 11771

Est $3,435,719

Not Listed For Sale

1167 Pine Valley Rd, Oyster Bay, NY 11771
- 6 Beds
- 4.5 Baths
- 5,909 Sq Ft
- Built 1951
1167 Pine Valley Rd, Oyster Bay, NY 11771

Last Sold Summary
- 76 Days On Market
Last Listing Agent Diana Mellone Daniel Gale Sothebys Intl Rlty

Showing Results 1 - 40, Page 1 of 17

New York Nassau County

Home Prices in Upper Brookville, NY

The median home sale price in Upper Brookville, NY is $2,500,000 year-over-year.

Home Price Trends

Median Sale Price $2,500,000	Median Single Family Sale Price $25,000,000
Average Price Per Sq Ft $1,115	Number of Homes for Sale 1
Last 12 months Home Sales 1	Months of Supply 12.00
Median List Price $13,499,000	Median Change From 1st List Price -25%

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Upper Brookville, NY Homes

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Home Prices in Upper Brookville, NY

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