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Old Hill Homes for Sale

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  • 119 Kings Hwy N, Westport, CT 06880
    119 Kings Hwy N, Westport, CT 06880
    119 Kings Hwy N, Westport, CT 06880
    /25

    $1,150,000

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    119 Kings Hwy N, Westport, CT 06880

    Build your dream house on this beautiful property close to town in the Old Hill section of Westport. This .87 acre lot in a AA zone has views of town and river through the trees. There is a small single-family home that was converted into two apartments in the 1930s by its then-owners. This can be a perfect ADU opportunity as part of a new house to be built. Have an office on one level and an

    Helen Cusa Brown Harris Stevens

    119 Kings Hwy N, Westport, CT 06880
  • 4 Crawford Rd, Westport, CT 06880
    4 Crawford Rd, Westport, CT 06880
    4 Crawford Rd, Westport, CT 06880
    /40

    $2,799,000

    Open Thu 10AM - 1PM Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 4,471 Sq Ft

    4 Crawford Rd, Westport, CT 06880

    Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeless character & modern comfort come together beautifully. Thoughtfully updated while preserving its remarkable architectural details, the residence features sun-filled interiors, beautifully scaled rooms, & an inviting warmth

    Barbara Sweeney Coldwell Banker Realty

    4 Crawford Rd, Westport, CT 06880
  • 34 Woodside Ave, Westport, CT 06880
    34 Woodside Ave, Westport, CT 06880
    34 Woodside Ave, Westport, CT 06880
    /37

    $2,699,000

    • 4 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    34 Woodside Ave, Westport, CT 06880

    Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, exceptional functionality, and a coveted location just an easy stroll to downtown Westport. Designed for both everyday living and easy entertaining, the home features warm gathering spaces and private retreats. A chef's kitchen with

    Cyd Hamer William Pitt Sotheby's Int'l

    34 Woodside Ave, Westport, CT 06880
  • 48 Woodside Ave, Westport, CT 06880
    48 Woodside Ave, Westport, CT 06880
    48 Woodside Ave, Westport, CT 06880
    /7

    $4,100,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 6,244 Sq Ft

    48 Woodside Ave, Westport, CT 06880

    A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and

    Judy Michaelis Coldwell Banker Realty

    48 Woodside Ave, Westport, CT 06880
  • 50 Sylvan Rd N, Westport, CT 06880
    50 Sylvan Rd N, Westport, CT 06880
    50 Sylvan Rd N, Westport, CT 06880
    /18

    $1,475,000

    • Land
    • 1.05 Acres
    • $1,404,762 per Acre

    50 Sylvan Rd N, Westport, CT 06880

    ATTENTION BUYERS : FLAT DRY, ONE -OF-A-KIND LAND OPPORTUNITY NOW HUGELY IMPROVED WITH WELL DEFINED SITE PLAN. Do you hope for new custom construction no bigger than "about" 4500sf, yet continue to see 7000sf and larger get the edge? Stop wishing for it and take action! Bring your architect or builder to consider a new home that meets your dream to be practically-sized for every life stage. No

    Martha Eidman Coldwell Banker Realty

    50 Sylvan Rd N, Westport, CT 06880
  • 31 Stonybrook Rd, Westport, CT 06880
    31 Stonybrook Rd, Westport, CT 06880
    31 Stonybrook Rd, Westport, CT 06880
    /36

    $5,750,000

    • 5 Beds
    • 8 Baths
    • 6,503 Sq Ft

    31 Stonybrook Rd, Westport, CT 06880

    Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an

    Kristi Law William Pitt Sotheby's Int'l

    31 Stonybrook Rd, Westport, CT 06880
  • 119 Kings Highway North Rd, Westport, CT 06880
    119 Kings Highway North Rd, Westport, CT 06880
    /2

    $1,150,000

    • Land
    • 37,897 Sq Ft
    • $1,321,839 per Acre

    119 Kings Highway North Rd, Westport, CT 06880

    Don't miss this great opportunity close to town. The .87Acre lot is elevated ,rolling and ideally positioned off Kings Highway. There are distance views of the river and town through the trees. There is an older small 1400 sq ft. single family home that has been a rental for many years. The previous owners in the 30's made each floor into apartments. Each level with its own entrance features a

    Helen Cusa Brown Harris Stevens

    119 Kings Highway North Rd, Westport, CT 06880
  • 1 Twin Oaks Ln, Westport, CT 06880
    1 Twin Oaks Ln, Westport, CT 06880
    1 Twin Oaks Ln, Westport, CT 06880
    /36

    $5,500,000

    • 5 Beds
    • 5.5 Baths
    • 9,421 Sq Ft

    1 Twin Oaks Ln, Westport, CT 06880

    Discover exceptional modern living in this stunning new construction home set on 1.68 acres of private, serene property in Westport, CT. Designed with both luxury and functionality in mind, this residence offers 5 spacious bedrooms and 7 beautifully appointed bathrooms. The primary suite is a true sanctuary, featuring three generous closets and a spa-inspired feel. Each additional bedroom is

    Zuzana Dankova HomeSmart Homes and Estates

    1 Twin Oaks Ln, Westport, CT 06880
Connecticut Fairfield County Westport

Real Estate & Homes for Sale in Old Hill, Westport

Why Live in Old Hill
Old Hill in Westport is an upscale suburb located west of the Saugatuck River, known for its larger lots and proximity to downtown. The neighborhood features a variety of home styles, including Colonial-inspired mansions, New England estates, and modern and rustic farmhouses, often set back from the road under mature trees. Many homes boast four or more bedrooms, private pools, and large garages. Trendy condo units at Bankside House offer modern industrial designs with floor-to-ceiling windows and views of the Saugatuck River. The Westport School District, which serves Old Hill, is highly rated, with King’s Highway Elementary School, Coleytown Middle School, and Staples High School all receiving top marks. Residents can enjoy a range of activities and amenities, including art galleries, boutiques, and locally-owned restaurants in downtown Westport. Community events at the Levitt Pavilion and Compo Beach foster a sense of togetherness. The Westport Library offers a coffee shop and hosts various events, while the Westport Weston Family YMCA provides family-friendly activities. Partrick Wetlands offers walking trails and views of native plants, though some homes may experience wetter seasons due to the marshy landscape. Old Hill is conveniently located less than 3 miles from downtown Westport, with Norwalk about 4 miles south. Essential shopping can be done at Trader Joe’s, Organic Market, and Westport Hardware on Post Road. Dining options include Outpost Pizza and Mexicue, known for its barbecue menu and lively atmosphere. Annual events such as the Levitt Pavilion’s festival season and the Westport Fine Arts Festival provide entertainment and cultural enrichment for residents.
Learn more about living in Old Hill

Old Hill Home Prices vs. Nearby Westport, CT Neighborhoods

Old Hill Staples Coleytown Compo
Median Home Price
$2,199,000
$2,218,000
$2,724,500
$2,747,000
Median Sale Price
$2,050,000
-21% YoY
$2,325,000
+5% YoY
$2,438,000
+13% YoY
$2,460,000
+78% YoY
Median Single Family Price
$2,400,000
$2,775,000
$2,662,500
$2,825,000
Total Active Listings
6
18
10
8
Market Conditions
2 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market

Frequently Asked Questions

Is Old Hill a good place to live?
Old Hill is a good place to live. Old Hill is considered car-dependent and somewhat bikeable with minimal transit options. Old Hill is a suburban neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Old Hill has 6 parks for recreational activities. It is sparse in population with 2.0 people per acre and a median age of 46. The average household income is $250,870 which is above the national average. College graduates make up 84.6% of residents. A majority of residents in Old Hill are home owners, with 13% of residents renting and 87% of residents owning their home. A local real estate agent serving Old Hill can help you decide if this neighborhood is the right one for you. Learn more on our Old Hill neighborhood guide.
Is Old Hill, CT a safe neighborhood?
Old Hill, CT is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Old Hill?
The median home price in Old Hill is $2,199,000. If you put a 20% down payment of $439,800 and had a 30-year fixed mortgage with an interest rate of 6.55%, your estimated principal and interest payment would be $11,180 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $479K a year to afford the median home price in Old Hill. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Old Hill is $251K.
What are the best public schools in Old Hill?
The best public schools that serve Old Hill are:
What are the best private schools in Old Hill?
The best private schools that serve Old Hill are:
What are the most popular zip codes in Old Hill, Westport, CT?
The most popular zip codes in Old Hill, Westport, CT include 06880, 06851, 06897, 06883 and 06855.
What are the most popular neighborhoods near Old Hill, Westport, CT?
The most popular neighborhoods near Old Hill, Westport, CT are Westport Village, Saugatuck, Wolfpit, Cranbury and Woods Pond.
Are home prices dropping in Old Hill?
Yes, home prices in Old Hill are down 22% in the last 12 months.
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