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Old Hill Homes for Sale

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  • 10 Side Hill Rd, Westport, CT 06880
    10 Side Hill Rd, Westport, CT 06880
    10 Side Hill Rd, Westport, CT 06880
    /40

    $3,250,000

    • 6 Beds
    • 6 Baths
    • 6,844 Sq Ft

    10 Side Hill Rd, Westport, CT 06880

    Now more than ever, home is a haven - a place to live, work, relax, and entertain. Privately sited on 1 beautifully landscaped acre in highly sought-after Old Hill, this sophisticated 6,000+ SF home with a brand-new pool offers 6 bedrooms, exceptional living spaces, and breathtaking western sunsets overlooking Earthplace's 62-acre nature sanctuary. A rare blend of privacy, style, and convenience,

    Agent Photo

    Susan Lieberman

    The Riverside Realty Group

    (475) 303-4846

    10 Side Hill Rd, Westport, CT 06880
  • 34 Pequot Trail, Westport, CT 06880
    34 Pequot Trail, Westport, CT 06880
    34 Pequot Trail, Westport, CT 06880
    /28

    $2,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,782 Sq Ft

    34 Pequot Trail, Westport, CT 06880

    Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases

    Lynn Fraund William Pitt Sotheby's Int'l

    34 Pequot Trail, Westport, CT 06880
  • 2 Grassy Plains Rd, Westport, CT 06880
    2 Grassy Plains Rd, Westport, CT 06880
    2 Grassy Plains Rd, Westport, CT 06880
    /40

    $1,699,000

    • 4 Beds
    • 3.5 Baths
    • 2,881 Sq Ft

    2 Grassy Plains Rd, Westport, CT 06880

    *SELLERS ARE AKSING FOR HIGHEST AND BEST OFFERS BY 4PM MONDAY JUNE 1ST*Set on a beautifully landscaped, bucolic acre at the top of a quiet cul-de-sac in Westport's coveted Old Hill neighborhood, this charming cottage-style ranch home offers the perfect blend of modern convenience, and luxurious Westport lifestyle. Move-in ready and beautifully maintained it's thoughtful layout is ideal for both

    Jessica Brookbanks Coldwell Banker Realty

    2 Grassy Plains Rd, 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
  • 30 Pequot Trail, Westport, CT 06880
    30 Pequot Trail, Westport, CT 06880
    30 Pequot Trail, Westport, CT 06880
    /34

    $1,599,876

    $75K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,156 Sq Ft

    30 Pequot Trail, Westport, CT 06880

    Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a

    Lynn Fraund William Pitt Sotheby's Int'l

    30 Pequot Trail, Westport, CT 06880
  • 50 Sylvan Rd N, Westport, CT 06880
    50 Sylvan Rd N, Westport, CT 06880
    50 Sylvan Rd N, Westport, CT 06880
    /19

    $1,475,000

    Open Sat 1AM - 3PM
    • 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 seek new custom construction no bigger than "about" 4500sf. Are you frustrated by the spec-builder focus on super-sized 7000-to-10,000sf homes that you can't make practical sense of for your lifestyle? Stop wishing for it and take action! Bring your architect or builder to consider

    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
  • 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
  • 5 Tanglewood Ln, Westport, CT 06880
    5 Tanglewood Ln, Westport, CT 06880
    5 Tanglewood Ln, Westport, CT 06880
    /40

    $1,975,000

    • 4 Beds
    • 3 Baths
    • 3,253 Sq Ft

    5 Tanglewood Ln, Westport, CT 06880

    Set on a quiet, convenient street in Westport's coveted Old Hill, this charming home captures the essence of Fairfield County living. A picturesque acre with level lawns, a sparkling pool, and expansive patios creates an exceptional outdoor retreat ideal for relaxing or entertaining. A welcoming front porch leads into a thoughtfully renovated interior with beautifully proportioned spaces and

    Doug Bross Coldwell Banker Realty

    5 Tanglewood Ln, Westport, CT 06880
Connecticut Fairfield County Westport Old Hill

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

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 $2,174,500. If you put a 20% down payment of $434,900 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $10,780 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $462K 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 06850.
What are the most popular neighborhoods near Old Hill, Westport, CT?
The most popular neighborhoods near Old Hill, Westport, CT are Wolfpit, Westport Village, Saugatuck, Cranbury and Staples.
Are home prices dropping in Old Hill?
Yes, home prices in Old Hill are down 14% in the last 12 months.

Old Hill Home Prices vs. Nearby Westport, CT Neighborhoods

Old Hill Staples Coleytown Greenfield Hill
Median Home Price
$2,174,500
$2,147,000
$2,647,000
$1,599,000
Median Sale Price
$2,199,060
-19% YoY
$2,120,500
-4% YoY
$2,335,000
+26% YoY
$1,600,000
Median Single Family Price
$2,257,500
$2,725,000
$2,535,000
$1,652,750
Median Townhouse Price
$450,500
$1,395,000
$2,099,000
--
Median Condo Price
$525,000
$1,420,000
--
$1,050,000
Total Active Listings
8
24
12
25
Market Conditions
3 Months
Seller's Market
3 Months
Seller's Market
4 Months
Seller's Market
3 Months
Seller's Market
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