New homes for sale & real estate in Holly Hill, FL

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ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Luxurious Ten-Bedroom Home at Windsor Island Resort, Minutes from Disney World! This grand, fully furnished home built in 2023 offers exceptional rental income potential and is located at Windsor Island Resort, less than 10 miles from the Magic Kingdom. With 10 bedrooms, 8 bathrooms, and ample space to host guests, this home features an open kitchen, a private pool, spa, and a luxury-covered lanai. The two-car garage has been converted into a game room with insulation and AC/heater installed, providing additional entertainment space for guests. The home comfortably sleeps up to 22 guests, with each room professionally and thoughtfully themed-designed for guests of all ages. Enjoy a spacious

$995,000

10 beds8 baths4,399 sq ft

4494 Kaipo Rd, Davenport, FL 33897

Private pool • Luxury-covered lanai • Game room

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
This professionally designed, fully furnished 7-bedroom, 5.5-bath vacation retreat offering over 3,200 square feet of upgraded living space in one of Central Florida’s most sought-after resort communities. This turnkey property blends upscale finishes with functional design, ideal for investors and vacationers alike. Step inside to discover a spacious open-concept layout perfect for large groups. The gourmet kitchen features rich espresso cabinetry, granite countertops, stainless steel appliances, and a generous center island with seating that's ideal for casual dining and entertaining. The main-level primary suite offers direct pool access and a spa-inspired en suite bath with dual s

$709,000

7 beds5.5 baths3,282 sq ft

3937 Lana Ave, Davenport, FL 33897

Lazy river • Gourmet kitchen • Private game room

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Welcome to the epitome of themed luxury living! Step into a world of enchantment with this well-themed, nearly brand-new vacation home, nestled in the heart of the newly developed Windsor Island Resort. This fully furnished 10-bedroom, 8-bathroom haven is not just a house; it's a turnkey cash cow that can comfortably accommodate 20+ guests, making it the perfect retreat for group vacations. As you enter, you'll be captivated by the exquisite details that adorn this residence, creating an atmosphere of sophistication and charm. The gourmet kitchen, large dining area, and spacious living room seamlessly blend together, offering the perfect setting for entertaining and creating unforgettable m

$850,000

10 beds8 baths4,399 sq ft

4361 Lana Ave, Davenport, FL 33897

Gated community • Lazy river • Gourmet kitchen

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Welcome to the Ultimate Dream Home in Windsor Island! Get ready to fall in love with this fully themed townhouse, perfect for unforgettable vacations, or short-term rental investment! With 210 square meters (approx. 2,260 sq ft) of living space, this stunning home offers 5 bedrooms, 4.5 bathrooms, and custom-designed environments that deliver fun, comfort, and magic for the whole family. Themed Bedrooms & Endless Entertainment: Mickey Mouse bedroom, Super Mario bedroom, Harry Potter bedroom, Star Wars bedroom, Prada bedroom, Private home theater, fully equipped game room with arcade machines, slot machine, and more! Every space has been carefully decorated to create a truly immersi

$599,000

5 beds4.5 baths2,283 sq ft

3922 Lana Ave, Davenport, FL 33897

Slot machine • Private home theater • Arcade machines

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
This luxurious 5-bedroom, 4.5-bathroom vacation home is located in Windsor Island Resort, one of Orlando’s top vacation communities with the highest occupancy rates. Built in 2023 and fully furnished and professionally decorated, this home is income-ready and already has confirmed bookings for 2025. The modern open-concept design features a kitchen with stainless steel appliances, a central island, integrated living and dining areas, and themed bedrooms that delight guests of all ages. The outdoor space offers a private screened-in pool and lanai, perfect for fun and relaxation. Windsor Island Resort provides world-class amenities including a water park, lazy river, water slides, fitn

$540,000

5 beds4.5 baths2,283 sq ft

4358 Lana Ave, Davenport, FL 33897

Themed bedrooms • Fitness center • $810 HOA

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 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 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 4250 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$520,000

5 beds4.5 baths2,283 sq ft

4250 Lana Ave, Davenport, FL 33897

Property at 4306 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$630,000

5 beds4.5 baths2,263 sq ft

4306 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 4294 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$549,000

5 beds4.5 baths2,280 sq ft

4294 Lana Ave, Davenport, FL 33897

Property at 4270 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$549,000

5 beds4.5 baths2,283 sq ft

4270 Lana Ave, Davenport, FL 33897

Property at 4314 Lana Ave, Davenport, FL 33897, 5 beds, 4 baths

$639,000

5 beds4 baths2,283 sq ft

4314 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 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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NEW 18 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
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. 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 room designed for effortless entertaining. T

$819,000

10 beds8 baths4,399 sq ft

4149 Lana Ave, Davenport, FL 33897

Fitness center • Resort style pool • Gourmet kitchen

OPEN TODAY, 12PM TO 5PM

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Under Construction. Upon entering the Malibu III, guests are greeted by a grand foyer that leads to a home built for entertaining. The kitchen features an expansive island complemented with granite counter tops, a chef-worthy walk-in pantry, a dining room, and stainless-steel appliances. At 3,500+ square feet, the Malibu III boasts 7 bedrooms, 6.5 bathrooms, a 2nd-floor loft and a gathering room bathed in natural light from the adjacent lanai. The Malibu III includes 2 primary rooms, with one located on the 1st floor. Featuring generous walk-in closets and a bathroom with a double sink vanity, the primary rooms are the perfect oasis for guests to relax and unwind after a long day. Melt away

$805,990

7 beds6.5 baths3,544 sq ft

2371 Sea Rock Rose Trl, Kissimmee, FL 34747

Expansive island • Gathering room • Grand foyer

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Epic listing!!! Discover one of the most exceptional 5-bedroom vacation townhomes in the coveted Windsor Island Resort. This professionally designed retreat features high-end finishes and immersive themed spaces throughout, creating a one-of-a-kind experience for guests of all ages. Every detail has been carefully curated by a luxury design team, from the custom wall treatments to the thoughtfully integrated lighting and decor. Themed bedrooms evoke the excitement of Harry Potter, Star Wars, Frozen, Mickey Mouse, and Minions—perfect for transporting families into the heart of their favorite worlds. The fun continues with a dedicated game room equipped with multiple arcade setups and e

$559,000

5 beds4.5 baths2,283 sq ft

4210 Lana Ave, Davenport, FL 33897

Themed bedrooms • Short term rental • Dedicated game room

3D WALKTHROUGH

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Escape to luxury in this immaculate Windsor Island Resort home in Davenport, Florida. This 8-bedroom, 6-bathroom residence offers a full sun, south-facing pool, and an open, airy floor plan perfect for vacation living, multigenerational guests, or a lucrative rental opportunity. Interiors feature tasteful, whimsical decor with carpeted bedrooms and durable ceramic tile plus luxury vinyl plank throughout for easy maintenance. Entertainment highlights include a dedicated game room and a game loft. Outdoor living is highlighted by a covered lanai and sun-drenched pool, with easy-to-maintain landscaping. The community provides a fully guarded, gated resort-within-a-resort experience and access

$869,000

8 beds6 baths4,025 sq ft

4125 Lana Ave, Davenport, FL 33897

Clubhouse • Gated resort • Covered lanai

OPEN TODAY, 12PM TO 5PM

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Upon entering The Laguna III, guests are greeted by a grand foyer that leads to a home built with entertaining in mind. The kitchen features an expansive island complemented with granite counter tops, a breakfast bar, a chef-worthy pantry, a breakfast nook and stainless-steel appliances. At 2,700+ square feet, The Laguna III boasts 6 bedrooms, 4.5 bathrooms, a 2nd-story loft and a gathering room bathed in natural light from the adjacent covered lanai. Located on the 1st floor and featuring generous closet space and an owner's bath with a double sink vanity, the owner's suite is the perfect oasis for guests to relax and unwind after a long day. Melt away stress and take advantage of the Flor

$745,990

6 beds4.5 baths3,021 sq ft

2311 Sea Rock Rose Trl, Kissimmee, FL 34747

Expansive island • Breakfast nook • Chef-worthy pantry

OPEN TODAY, 12PM TO 5PM

ABOUT THIS HOME
New Home for sale in Holly Hill, FL:
Under Construction. Upon entering The Laguna III, guests are greeted by a grand foyer that leads to a home built with entertaining in mind. The kitchen features an expansive island complemented with granite counter tops, a breakfast bar, a chef-worthy pantry, a breakfast nook and stainless-steel appliances. At 2,700+ square feet, The Laguna III boasts 6 bedrooms, 4.5 bathrooms, a 2nd-story loft and a gathering room bathed in natural light from the adjacent covered lanai. Located on the 1st floor and featuring generous closet space and an owner's bath with a double sink vanity, the owner's suite is the perfect oasis for guests to relax and unwind after a long day. Melt away stress and take a

$745,990

6 beds4.5 baths3,021 sq ft

2319 Sea Rock Rose Trl, Kissimmee, FL 34747

Expansive island • Breakfast nook • Chef-worthy pantry

Property at Undisclosed address, Davenport, FL 33897, 5 beds, 4.5 baths

$610,000

5 beds4.5 baths2,283 sq ft

Undisclosed address, Davenport, FL 33897

Property at 2328 Distant Sun Trl, Kissimmee, FL 34747, 6 beds, 4.5 baths

$745,990

6 beds4.5 baths3,009 sq ft

2328 Distant Sun Trl, Kissimmee, FL 34747

Property at 2312 Distant Sun Trl, Kissimmee, FL 34747, 6 beds, 4.5 baths

$747,990

6 beds4.5 baths3,009 sq ft

2312 Distant Sun Trl, Kissimmee, FL 34747

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

$1,149,000

10 beds8 baths4,399 sq ft

Undisclosed address, Davenport, FL 33897

Property at 4098 Lana Ave, Davenport, FL 33897, 5 beds, 4 baths

$499,000

5 beds4 baths2,283 sq ft

4098 Lana Ave, Davenport, FL 33897

Property at 4070 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$659,000

5 beds4.5 baths2,283 sq ft

4070 Lana Ave, Davenport, FL 33897

Property at 4014 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$489,000

5 beds4.5 baths2,283 sq ft

4014 Lana Ave, Davenport, FL 33897

Property at 3966 Lana Ave, Davenport, FL 33897, 5 beds, 4 baths

$559,000

5 beds4 baths2,283 sq ft

3966 Lana Ave, Davenport, FL 33897

Property at 4166 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$514,990

5 beds4.5 baths2,263 sq ft

4166 Lana Ave, Davenport, FL 33897

Property at 3974 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$489,850

5 beds4.5 baths2,283 sq ft

3974 Lana Ave, Davenport, FL 33897

Property at 4058 Lana Ave, Davenport, FL 33897, 5 beds, 4.5 baths

$590,000

5 beds4.5 baths2,269 sq ft

4058 Lana Ave, Davenport, FL 33897

Property at 4458 Kaipo Rd, Davenport, FL 33897, 7 beds, 5.5 baths

$800,000

7 beds5.5 baths3,281 sq ft

4458 Kaipo Rd, Davenport, FL 33897

Property at 4424 Kaipo Rd, Davenport, FL 33897, 7 beds, 5.5 baths

$874,000

7 beds5.5 baths3,286 sq ft

4424 Kaipo Rd, Davenport, FL 33897

Property at 4063 Lana Ave, Davenport, FL 33897, 6 beds, 4.5 baths

$729,000

6 beds4.5 baths3,286 sq ft

4063 Lana Ave, Davenport, FL 33897

Based on information submitted to the MLS GRID as of Sun Nov 30 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.

New Homes for Sale in Holly Hill

There are currently 16 new homes for sale in Holly Hill at a median listing price of $709K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Holly Hill stay on the market for 165 days. Popular neighborhoods include Highlands Reserve, Happy Trails, Paradise Palms, Caribe Cove, Bahama Bay Condominiums, Silvermine, Citrus Ridge, Polo Park, Championsgate, and Emerald Island. This map is refreshed with the newest listings in Holly Hill every 15 minutes.

In the past month, 7 homes have been sold in Holly Hill. In addition to houses in Holly Hill, there were also 0 condos, 35 townhouses, and 0 multi-family units for sale in Holly Hill last month. Find your dream home in Holly Hill using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Holly Hill are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Holly Hill. If you're looking to sell your home in the Holly Hill area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Holly Hill with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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