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Village of Hillsborough Homes for Sale

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  • /39

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    2104 Iveywood St, The Villages, FL 32163

    SHORT GOLFCART RIDE to BROWNWOOD TOWN SQUARE. NESTLED IN THE VILLAGE OF HILLSBOROUGH Discover your dream home in this stunning 3 bed, 2-bath At Ease Model home. This corner lot property offers Room for a Pool, perfect for those who enjoy outdoor leisure. Step inside to find luxurious vinyl plank flooring that seamlessly flows throughout the open-concept layout, accentuated by elegant crown

    Agent Photo

    Karen Kamperman

    KELLER WILLIAMS CORNERSTONE RE

    (352) 605-7386

    2104 Iveywood St, The Villages, FL 32163
  • /23

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    2092 Ironton Place, The Villages, FL 32163

    Welcome to this rare FAIRMONT MODEL nestled just minutes from Brownwood Paddock Square. This beautifully updated 3-bedroom, 2-bath home offers an inviting OPEN FLOOR PLAN with BRAND NEW LUXURY VINYL PLANK flooring throughout—NO CARPET. The tile has been professionally cleaned, and the FRESHLY PAINTED exterior adds to its MOVE-IN READY appeal. The ENTERTAINMENT-style kitchen is brightened by a

    Chesney Mcgee NEXTHOME SALLY LOVE REAL ESTATE

    2092 Ironton Place, The Villages, FL 32163
  • /39

    $355,900

    • 2 Beds
    • 2 Baths
    • 1,206 Sq Ft

    2085 Ironton Place, The Villages, FL 32163

    TURN KEY Cambridge style Courtyard Villa in the sought after Village of Hillsborough. This home is beautifully furnished, decorated and maintained. As you arrive, notice the mature landscaping, covered front porch and leaded glass entry door. Stepping inside, admire the engineered hardwood flooring (new 2023) and high ceilings. The large sliding doors, windows and bright walls (newly painted

    Mark Sevegny RE/MAX PREMIER REALTY

    2085 Ironton Place, The Villages, FL 32163
  • /39

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,035 Sq Ft

    1965 Gatehouse Terrace, The Villages, FL 32163

    This Gardenia model sounds like a wonderful place to call home! With its oversized lot and prime location in the Village of Lake Deaton, it offers both space and tranquility. The strategic positioning ensures that there is no one directly off the lanai, and it is complemented by a privacy wall, enhancing your peaceful retreat. Recent updates, including a new HVAC and roof, provide peace of mind

    Darcie Furnier REALTY EXECUTIVES IN THE VILLAGES

    1965 Gatehouse Terrace, The Villages, FL 32163
  • /61

    $750,000

    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    2082 Vision Ct, The Villages, FL 32163

    Don’t miss this extraordinary opportunity to own a beautifully upgraded Camellia Designer home with a tranquil water view with room for a pool, located in the highly desirable Village of Hillsborough. This one-of-a-kind property offers both elegance and peace of mind with a built-in, in-ground “SURVIVE-A-STORM” tornado/hurricane shelter, discreetly tucked within the enclosed lanai—possibly the

    Katy Kelly RE/MAX PREMIER REALTY

    2082 Vision Ct, The Villages, FL 32163
  • /24

    $294,900 Open Wed 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft

    3780 Viscaya Ct, The Villages, FL 32163

    Motivated Seller! Welcome to 3780 Viscaya Court, in the vibrant Village of Hillsborough! Experience the ultimate in Florida living at The Villages in this charming 2-bedroom, 2-bath home, perfectly designed for comfort and convenience. Unwind in the spacious primary suite, complete with a private en suite bathroom and a generous walk-in closet. Enjoy the Florida sunshine on the enclosed front

    Tim DiMaria NEXTHOME SALLY LOVE REAL ESTATE

    3780 Viscaya Ct, The Villages, FL 32163
  • /34

    $375,000 Open Fri 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,501 Sq Ft

    3810 Cosmos Way, The Villages, FL 32163

    Nestled in the desirable Village of Hillsborough, this charming 3/2 Seabreeze home offers an oversized TWO-CAR + GOLF-CAR GARAGE, LARGE LANAI with a birdcage extension, REAR PRIVACY (NO KISSING LANAIS), a STUNNING KITCHEN, and a PRIME LOCATION just minutes from Brownwood Paddock Square. The front exterior features a large driveway leading to a beautifully landscaped entryway, complete with a

    Matt Roberts RE/MAX PREMIER REALTY LADY LK

    3810 Cosmos Way, The Villages, FL 32163

Why Live in Village of Hillsborough

The Village of Hillsborough in Wildwood features contemporary homes starting around $300,000, with styles such as Courtyard Villa and Cottage. These homes typically include two bedrooms and two bathrooms, while larger homes with three to four bedrooms, corner lots, and lake views can reach up to $800,000. Many homes come with high-end appliances, heated backyard pools, oversized lanais, and two-car garages with additional space for golf carts. The neighborhood is known for its neatly manicured front yards adorned with small palm trees and flowers. Hillsborough lacks sidewalks, but the streets are spacious enough for walking dogs and biking. The neighborhood boasts an adults-only pool at its recreation center, while nearby golf options include the 27-hole Evans Prairie Country Club and the nine-hole Palmetto and Mangrove Executive Golf Courses. Residents can shop at Aldi, Publix, and Lowe's on Sumter County Road 466A, or visit Brownwood Paddock Square, less than 2 miles away, for dining and specialty shops. Dining options include Fiesta Grande for Mexican cuisine and Prima Italian Steakhouse. For travel, State Route 44 and Florida’s Turnpike provide access to Orlando, about 55 miles away.

Frequently Asked Questions

Is Village of Hillsborough a good place to live?
Village of Hillsborough is a good place to live. Village of Hillsborough is considered very car-dependent and somewhat bikeable. Village of Hillsborough is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Village of Hillsborough has 1 park for recreational activities. It has a median age of 73. The average household income is $100,070 which is above the national average. College graduates make up 53.1% of residents. A majority of residents in Village of Hillsborough are home owners, with 4.6% of residents renting and 95.4% of residents owning their home. A local real estate agent serving Village of Hillsborough can help you decide if this neighborhood is the right one for you. Learn more on our Village of Hillsborough neighborhood guide.
Is Village of Hillsborough, FL a safe neighborhood?
Village of Hillsborough, FL is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
What are the best public schools in Village of Hillsborough?
The best public schools that serve Village of Hillsborough are:
What are the most popular zip codes in Village of Hillsborough, Wildwood, FL?
The most popular zip codes in Village of Hillsborough, Wildwood, FL include 34785, 32162, 34748, 33585 and 34731.
What are the most popular neighborhoods near Village of Hillsborough, Wildwood, FL?
The most popular neighborhoods near Village of Hillsborough, Wildwood, FL are Village of Dunedin, Village of Collier, Village of Fernandina, Village of Gilchrist and Village of Pinellas.
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