Holly Hill, FL homes for sale & real estate

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ABOUT THIS HOME
Holly Hill, FL Homes for Sale
Exceptional Value in Windsor Island Resort! Luxuriously Upgraded & Themed Vacation Home. Discover the perfect blend of luxury, fun, and investment potential with this stunning 10-bedroom, 8-bathroom vacation home in the sought-after Windsor Island Resort. With space to comfortably host over 20 guests, this fully furnished and professionally designed home is ideal for memorable family vacations or maximizing short-term rental income. No detail was spared—over $170,000 in thoughtful upgrades bring sophistication and excitement to every corner. Step inside to an open-concept layout featuring elegant finishes, a spacious gourmet kitchen, a generous dining area, and a stylish living

$935,000

10 beds8 baths4,399 sq ft

3715 Lana Ave, Davenport, FL 33897

Themed bedrooms • 000 sq ft clubhouse • 8

ABOUT THIS HOME
Holly Hill, FL Homes for Sale
Welcome to your dream home in Davenport! This stunning, spacious residence offers 8 bedrooms and 6 bathrooms, providing ample room for a large family or someone who needs plenty space. The inviting layout combines comfort and elegance, with cozy living areas and a beautifully designed interior. Step outside to enjoy the private pool, perfect for relaxing or entertaining guests. Don’t miss the chance to own this exquisite home, where every detail is crafted for both luxury and functionality.

$1,150,000

8 beds6.5 baths4,036 sq ft

3625 Lily Ln, Davenport, FL 33897

5,994 sq ft lot • 2 garage spots • Pool

3D WALKTHROUGH

ABOUT THIS HOME
Holly Hill, FL Homes for Sale
Stunning 10-Bedroom Pool Home | Corner Lot | High-Yield STR in Windsor Island Resort Welcome to an extraordinary opportunity to own a fully furnished 10-bedroom, 8-bathroom single-family home on a premium corner lot in the prestigious Windsor Island Resort—Central Florida’s most captivating vacation community. This impressive residence is now available and offers a rare blend of luxury, location, and strong short-term rental performance. Step inside and experience the scale and elegance of this professionally designed home. With a spacious, open-concept layout and carefully curated finishes throughout, this home is built for both entertaining and relaxing. The highlight: a pr

$830,000

10 beds8 baths4,399 sq ft

2191 Lelani Cir, Davenport, FL 33897

Lazy river • Dual water slides • Fitness center

ABOUT THIS HOME
Holly Hill, FL Homes for Sale
Get ready to be enchanted by this magnificent 5-bedroom, 4.5-bathroom townhome , nestled in the prestigious Windsor Island Resort — a coveted address blending luxury and comfort! This home comes equipped with a fully installed solar panel system, offering significant savings on electricity bills and a more sustainable lifestyle. Just a short walk from the clubhouse, this stunning home is designed with modern sophistication, making it perfect for families seeking unforgettable memories or investors looking for a high-return short-term rental property. Enjoy spacious living areas, contemporary finishes, and a private outdoor retreat, ideal for relaxation. Windsor Island Resort elevates

$500,000

5 beds4.5 baths2,283 sq ft

236 Jetty Way, Davenport, FL 33897

Fitness center • Mini golf • $734 HOA

ABOUT THIS HOME
Holly Hill, FL Homes for Sale
Welcome to 3353 Lilac Way - a must-see for anyone in search of a great Airbnb rental property in an iconic, Disney area, Vacation home resort - just a few short miles to Orlando’s world famous theme parks and local area attractions! Discover the captivating charm of Windsor Island Resort, where Hawaiian-inspired vacation vibes prevail throughout, from its picturesque clubhouse and amenities to its enchanting street names. Prepare to be impressed by this gorgeous 2022 Pulte built home, which epitomizes modern comfort and entertainment, offering an ideal retreat for short-term vacation rentals or personal getaways. Windsor Island Resort sets the standard as a highly desirable destinatio

$659,000

7 beds5.5 baths3,282 sq ft

3353 Lilac Way, Davenport, FL 33897

Upgraded cabinetry • 4,953 sq ft lot • 2 garage spots

Property at 3012 Mahalo Dr, Davenport, FL 33897, 10 beds, 8 baths

$950,000

10 beds8 baths4,399 sq ft

3012 Mahalo Dr, Davenport, FL 33897

Property at 3016 Mahalo Dr, Davenport, FL 33897, 8 beds, 6 baths

$758,000

8 beds6 baths4,036 sq ft

3016 Mahalo Dr, Davenport, FL 33897

Property at 1978 Summer Dr, Davenport, FL 33897, 10 beds, 8 baths

$949,000

10 beds8 baths4,399 sq ft

1978 Summer Dr, Davenport, FL 33897

Property at 4237 Lana Ave, Davenport, FL 33897, 8 beds, 6 baths

$790,000

8 beds6 baths4,028 sq ft

4237 Lana Ave, Davenport, FL 33897

Property at 3428 Lilac Way, Davenport, FL 33897, 5 beds, 5.5 baths

$679,900

5 beds5.5 baths2,622 sq ft

3428 Lilac Way, Davenport, FL 33897

Property at 2166 Lelani Cir, Davenport, FL 33897, 8 beds, 6 baths

$849,000

8 beds6 baths4,036 sq ft

2166 Lelani Cir, Davenport, FL 33897

Property at 3818 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$535,000

5 beds4.5 baths2,293 sq ft

3818 Lana Ave, Davenport, FL 33897

Property at 4305 Lana Ave, Davenport, FL 33897, 8 beds, 6 baths

$875,000

8 beds6 baths4,399 sq ft

4305 Lana Ave, Davenport, FL 33897

Property at 3083 Mahalo Dr, Davenport, FL 33897, 10 beds, 8 baths

$1,150,000

10 beds8 baths4,399 sq ft

3083 Mahalo Dr, Davenport, FL 33897

Property at 880 Paradise Dr, Davenport, FL 33897, 5 beds, 4.5 baths

$518,000

5 beds4.5 baths2,293 sq ft

880 Paradise Dr, Davenport, FL 33897

Property at 1166 Aloha Blvd, Davenport, FL 33897, 5 beds, 5.5 baths

$675,000

5 beds5.5 baths2,621 sq ft

1166 Aloha Blvd, Davenport, FL 33897

Property at 2260 Lelani Cir, Davenport, FL 33897, 10 beds, 8 baths

$840,000

10 beds8 baths4,399 sq ft

2260 Lelani Cir, Davenport, FL 33897

Property at 2190 Lelani Cir, Davenport, FL 33897, 10 beds, 8 baths

$980,000

10 beds8 baths4,399 sq ft

2190 Lelani Cir, Davenport, FL 33897

Property at 1876 Summer Dr, Davenport, FL 33897, 7 beds, 5.5 baths

$687,000

7 beds5.5 baths3,282 sq ft

1876 Summer Dr, Davenport, FL 33897

Property at 301 Jetty Way, Davenport, FL 33897, 5 beds, 4.5 baths

$521,900

5 beds4.5 baths2,283 sq ft

301 Jetty Way, Davenport, FL 33897

Property at 3413 Lilac, Davenport, FL 33897, 6 beds, 4.5 baths

$673,900

6 beds4.5 baths3,113 sq ft

3413 Lilac, Davenport, FL 33897

Property at 1320 Lava Tree Dr, Davenport, FL 33897, 5 beds, 4.5 baths

$499,900

5 beds4.5 baths2,293 sq ft

1320 Lava Tree Dr, Davenport, FL 33897

Property at 1870 Summer Dr, Davenport, FL 33897, 5 beds, 5.5 baths

$699,000

5 beds5.5 baths2,621 sq ft

1870 Summer Dr, Davenport, FL 33897

Property at 2026 Lelani Cir, Davenport, FL 33897, 8 beds, 6 baths

$790,000

8 beds6 baths4,025 sq ft

2026 Lelani Cir, Davenport, FL 33897

Property at 2123 Lelani Cir, Davenport, FL 33897, 8 beds, 6 baths

$830,000

8 beds6 baths4,036 sq ft

2123 Lelani Cir, Davenport, FL 33897

Property at 866 Paradise Dr, Davenport, FL 33897, 5 beds, 4.5 baths

$499,900

5 beds4.5 baths2,283 sq ft

866 Paradise Dr, Davenport, FL 33897

Property at 3209 Lilac Way, Davenport, FL 33897, 10 beds, 8 baths

$949,000

10 beds8 baths4,399 sq ft

3209 Lilac Way, Davenport, FL 33897

Property at 3525 Lavender Dr, Davenport, FL 33897, 8 beds, 6 baths

$884,900

8 beds6 baths4,036 sq ft

3525 Lavender Dr, Davenport, FL 33897

Property at 3922 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$599,000

5 beds4.5 baths2,283 sq ft

3922 Lana Ave, Davenport, FL 33897

Property at 3373 Lilac Way, Davenport, FL 33897, 5 beds, 5.5 baths

$727,000

5 beds5.5 baths2,622 sq ft

3373 Lilac Way, Davenport, FL 33897

Property at 3811 Lana Ave, Davenport, FL 33897, 5 beds, 5 baths

$719,000

5 beds5 baths2,622 sq ft

3811 Lana Ave, Davenport, FL 33897

Property at 2031 Lelani Cir, Davenport, FL 33897, 10 beds, 8 baths

$830,000

10 beds8 baths4,399 sq ft

2031 Lelani Cir, Davenport, FL 33897

Property at 197 Jetty Way, Davenport, FL 33897, 5 beds, 4.5 baths

$550,000

5 beds4.5 baths2,283 sq ft

197 Jetty Way, Davenport, FL 33897

Property at Undisclosed address, Davenport, FL 33897, 10 beds, 8 baths

$1,128,000

10 beds8 baths4,399 sq ft

Undisclosed address, Davenport, FL 33897

Property at 2176 Lelani Cir, Davenport, FL 33897, 9 beds, 6 baths

$875,000

9 beds6 baths4,399 sq ft

2176 Lelani Cir, Davenport, FL 33897

Property at 4321 Lana Ave, Davenport, FL 33897, 10 beds, 8 baths

$898,000

10 beds8 baths4,399 sq ft

4321 Lana Ave, Davenport, FL 33897

Property at 4322 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$579,990

5 beds4.5 baths2,283 sq ft

4322 Lana Ave, Davenport, FL 33897

Property at 3834 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$490,000

5 beds4.5 baths2,283 sq ft

3834 Lana Ave, Davenport, FL 33897

Property at 1000 Paradise Dr, Davenport, FL 33897, 5 beds, 4.5 baths

$549,000

5 beds4.5 baths2,283 sq ft

1000 Paradise Dr, Davenport, FL 33897

Property at 900 Paradise Dr, Davenport, FL 33897, 5 beds, 4.5 baths

$550,000

5 beds4.5 baths2,283 sq ft

900 Paradise Dr, Davenport, FL 33897

Property at 3312 Lilac WA, Davenport, FL 33897, 5 beds, 5 baths

$700,000

5 beds5 baths2,491 sq ft

3312 Lilac WA, Davenport, FL 33897

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Based on information submitted to the MLS GRID as of Fri Oct 24 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Holly Hill, FL

Cities

Neighborhoods

Highlands Reserve homes for sale
$280,000
Happy Trails homes for sale
$814,950
Paradise Palms homes for sale
$399,995
Caribe Cove homes for sale
$240,000
Bimini Bay homes for sale
$310,000
Bahama Bay Condominiums homes for sale
$219,925
Citrus Ridge homes for sale
$455,000
Polo Park homes for sale
Championsgate homes for sale
$465,000
Emerald Island homes for sale
$469,950

Holly Hill, FL real estate trends

$516K

Sale price

-26.5%
since last year

$198

Sale $/sq ft

-8.3%
since last year

Under list price

4.2%

Days on market

169

Down payment

—

Total homes sold

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