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Olde Cypress Homes for Sale

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  • /21

    $599,000

    $31K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,783 Sq Ft

    3134 Santorini Ct, Naples, FL 34119

    Welcome to 3134 Santorini Ct, a beautifully maintained single-family villa tucked inside the coveted gated enclave of Santorini at Olde Cypress. This light-filled 2-bedroom + den, 2-bath residence delivers comfort, privacy, and resort-style living in one of North Naples’ most desirable communities. Inside, the open-concept layout features soaring ceilings, neutral tones, and seamless

    Robert DeSiano DomainRealty.com LLC

    3134 Santorini Ct, Naples, FL 34119
  • /47

    $1,630,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,621 Sq Ft

    7352 Lantana Way, Naples, FL 34119

    Welcome to effortless Florida living in the prestigious Olde Cypress community, home to a celebrated P.B.Dye–designed golf course. This beautifully appointed fully turnkey Ruffino II residence allows you to simply arrive, unwind, and begin enjoying the lifestyle you’ve been waiting for—just bring your suitcase. Designed with both elegance and peace of mind, the light-filled interior features

    Angelo Sottosanti Coldwell Banker Realty

    7352 Lantana Way, Naples, FL 34119
  • /29

    $1,995,000

    • 3 Beds
    • 3 Baths
    • 2,816 Sq Ft

    3105 Terramar Dr, Naples, FL 34119

    Set against a picturesque golf course and lake backdrop with no homes in sight, this beautifully upgraded residence offers refined living in the sought-after community of Olde Cypress. Spanning approximately 2,800 square feet, the home features three bedrooms, a private study, and three full baths, thoughtfully designed for both everyday comfort and effortless entertaining. A grand interior

    Gregory Sofranko William Raveis Real Estate

    3105 Terramar Dr, Naples, FL 34119
  • /49

    $3,390,000

    • 4 Beds
    • 5 Baths
    • 5,538 Sq Ft

    3027 Mona Lisa Blvd, Naples, FL 34119

    One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to an amazing opportunity in Da Vinci Estates at Olde Cypress—an exclusive DOUBLE-GATED community known for estate-sized homes and unparalleled privacy. This property has LAKE VIEWS, a RARE FIVE-CAR GARAGE and a GUEST HOUSE. Major 2025 upgrades include: NEW ROOF, GUTTERS, FULL EXTERIOR PAINT, AND HVAC. Designed for

    Natalie Zimmer Coldwell Banker Realty

    3027 Mona Lisa Blvd, Naples, FL 34119

Why Live in Olde Cypress

Olde Cypress in Naples is a gated community known for its intimate atmosphere and Mediterranean-style homes. With only 540 homes, the neighborhood fosters a close-knit environment. The community features custom-built houses with tiled roofs, stucco siding, and indoor pools, set amidst wide green lawns and mature palm trees. Residents enjoy access to The Club at Olde Cypress, which includes an 18-hole championship golf course designed by P.B. Dye, a fitness center, pickleball and tennis courts, and a variety of social events. The area is safer than the national average, providing a secure living environment. Olde Cypress is conveniently located less than 10 miles from the Gulf Coast and near several retail hubs along Immokalee Road, offering dining options like Oak & Stone and Straight From New York Bagels, as well as grocery stores such as Target, Publix, and Walmart. For a unique shopping experience, Seed to Table offers farm-fresh produce and live music. The community is served by highly rated schools, including Laurel Oak Elementary School, Gulf Coast High School, and Oakridge Middle, all of which are located nearby. While the beach is a bit further away, Delnor-Wiggins Pass State Park is just seven miles down the road, and the heart of Naples is 15 miles away. Southwest Florida International Airport is 20 miles from the neighborhood, providing convenient travel options.

Frequently Asked Questions

Is Olde Cypress a good place to live?
Olde Cypress is a good place to live. Olde Cypress is considered very car-dependent and somewhat bikeable. Olde Cypress has 6 parks for recreational activities. It is sparse in population with 2.0 people per acre and a median age of 44. The average household income is $152,552 which is above the national average. College graduates make up 45% of residents. A majority of residents in Olde Cypress are home owners, with 28% of residents renting and 72% of residents owning their home. A local real estate agent serving Olde Cypress can help you decide if this neighborhood is the right one for you. Learn more on our Olde Cypress neighborhood guide.
Is Olde Cypress, FL a safe neighborhood?
Olde Cypress, FL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
How much do you need to make to afford a house in Olde Cypress?
The median home price in Olde Cypress is $1,325,000. If you put a 20% down payment of $265,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $6,680 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $286K a year to afford the median home price in Olde Cypress. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Olde Cypress is $153K.
What are the best public schools in Olde Cypress?
The best public schools that serve Olde Cypress are:
What are the best private schools in Olde Cypress?
The best private schools that serve Olde Cypress are:
What are the most popular zip codes in Olde Cypress, Naples, FL?
The most popular zip codes in Olde Cypress, Naples, FL include 34119, 34120, 34110, 34109 and 34113.
What are the most popular neighborhoods near Olde Cypress, Naples, FL?
The most popular neighborhoods near Olde Cypress, Naples, FL are Riverstone, Longshore Lake, Arrowhead-Island Walk, Quail Creek and Esplanade Golf and Country Club.
Are home prices dropping in Olde Cypress?
Yes, home prices in Olde Cypress are down 11% in the last 12 months.

Olde Cypress Home Prices vs. Nearby Naples, FL Neighborhoods

Olde Cypress Vineyards Pelican Marsh Kensington Park
Median Home Price
$1,325,000
$949,500
$1,065,000
$1,100,000
Median Sale Price
$1,275,000
-8% YoY
$885,000
+7% YoY
$915,000
+2% YoY
$885,000
-3% YoY
Median Single Family Price
$1,275,000
$1,300,000
$1,625,000
$1,624,500
Median Townhouse Price
--
$590,000
$2,775,000
$850,000
Median Condo Price
--
$525,000
$760,000
$770,000
Total Active Listings
8
193
78
8
Market Conditions
1 Months
Seller's Market
3 Months
Seller's Market
2 Months
Seller's Market
1 Months
Seller's Market
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