Pine Castle FL Waterfront Homes for Sale

3 Beds ⋅ 4 Baths ⋅ Jessamine Beach Rep SubDv. ⋅ 32839 Zip Code

Virtually Staged. Welcome to this beautifully maintained lakefront estate located on the pristine shores of Lake Jessamine, offering a rare opportunity to own in one of the area’s most coveted lake communities. Nestled on a sprawling lot with 120 feet of lake frontage, this home effortlessly blends luxury, comfort, and serene natural beauty. As you enter through a beautifully landscaped courtyard with a horseshoe driveway, you’re immediately greeted by the charm and grandeur of this exceptional property. The interior boasts 3 spacious bedrooms plus a flexible 4th bedroom, currently transformed into a custom California Closets-designed primary walk-in closet. The heart of the home is a modern chef’s kitchen complete with premium appliances, double ovens, expansive counter space, and a massive butler’s pantry/bonus kitchen, perfect for entertaining. Adjacent, the living area is both inviting and impressive, featuring two gas fireplaces, French doors, and large windows that frame breathtaking lake views with downtown Orlando as your scenic backdrop. Step outside to a custom-designed patio with an elegant fireplace, and a fully equipped outdoor kitchen, perfect for hosting gatherings overlooking the tranquil waters. The estate also features an oversized heated pool and spa with a covered 16 x 60 deck area, plus a private boat dock with electric lift, creating endless opportunities for lakefront leisure and entertainment. Additional highlights include; Roof replaced in 2022, upgraded pool & spa equipment 2024, Custom wet bar with built-in wine storage, integrated speaker system and hidden security system, Travertine tile throughout bathrooms, dining room, and a spa-inspired primary bath with custom finishes, Ample storage space with custom built-in shelving throughout, AC unit replaced 2023, floating jet ski dock recently installed, and custom garage cabinetry. This estate offers privacy and elegance while being just minutes from Orlando’s premier shopping, dining, entertainment, and city center. Experience the perfect balance of luxury living with the tranquility of a lakeside retreat.

5400 Kenmore Lane, Orlando

$639,000

3 Beds ⋅ 2 Baths ⋅ Jessamine Terrace Sub SubDv. ⋅ 32839 Zip Code

**Seller is willing to contribute money towards CLOSING COSTS or RATE BUY DOWN with acceptable offer!!!****SKI, BOAT, FISH & RELAX—YOUR LAKE JESSAMINE LIFESTYLE STARTS HERE!** Why buy a lakefront home that needs months of renovations when you can move right in and start enjoying the water from day one? This beautifully remodeled 3-bedroom, 2-bath lakefront home pairs stylish, move-in-ready interiors with something increasingly hard to find: your own **private boathouse, boat lift and dock directly on Lake Jessamine. Designed around the water, the bright open floor plan showcases beautiful lake views from nearly every room, with expansive sliders connecting the living spaces to a wraparound porch and backyard. Whether you're enjoying morning coffee overlooking the lake, entertaining friends for the afternoon, or heading out on the boat, this home was made for the Florida lake lifestyle. Inside, modern updates mean the work has already been done for you. Luxury vinyl flooring, contemporary finishes and automated shades complement the open living areas, while the beautifully remodeled kitchen serves as the heart of the home. It features porcelain tile flooring, quartz countertops, high-end appliances, an oversized island with bar seating, plus an additional quartz-topped serving and dry bar area with extra cabinetry—ideal for entertaining. Outside is where this property truly sets itself apart. The fenced backyard leads to your **private waterfront setup featuring a boathouse, boat lift, dock and screened-in lakeside lounge area**—ready to enjoy without taking on the time, expense and hassle of creating it yourself. Spend your weekends boating, waterskiing, fishing, entertaining by the water or simply relaxing and taking in the view from your own backyard. And you don't have to sacrifice convenience to live on the lake. You're just minutes from Downtown Orlando, Orlando International Airport, shopping, dining, major highways and Central Florida's world-famous attractions. Updated, move-in ready and already equipped for life on the water—this is your opportunity to own the complete Lake Jessamine lifestyle in the heart of Orlando.

5716 Moonlight Circle, Orlando

$585,000

3 Beds ⋅ 2 Baths ⋅ Lake Mary Shores SubDv. ⋅ 32839 Zip Code

PRIVATE SKI LAKE LIVING FOR $585K! A rare opportunity to own direct lakefront property on the private, spring fed waters of Lake Mary Jess, complete with your own private dock, slalom course access, oversized lot, and panoramic water views. Tucked away on a quiet dead end street with exceptional privacy, 5769 Rockwood Ave. offers the kind of Florida lifestyle that's increasingly difficult to find at this price point. This move in ready 3 bedroom, 2 bath home with an additional flex room combines updated interiors with true waterfront living just minutes from Downtown Orlando and MCO. From the moment you step inside, the lake takes center stage. Oversized sliding glass doors fill the home with natural light and frame beautiful water views from the main living areas and primary suite. Wake up overlooking the lake, enjoy your morning coffee by the water, and spend your afternoons boating, waterskiing, fishing, paddle boarding, or relaxing from your own private dock. The renovated kitchen features stone countertops, wood cabinetry, stainless steel appliances, and an open layout ideal for everyday living and entertaining. Outside is where this property truly sets itself apart. The oversized waterfront lot offers mature canopy trees, 10 foot viburnum hedges for added privacy, a summer kitchen, and plenty of space to entertain or create your own private backyard retreat. Additional side yard space provides flexibility for boat storage, extra parking, or a workshop. Recent improvements include a remodeled kitchen and dining area, updated bathrooms, fresh interior paint, exterior waterproofing, new landscaping with irrigation, and more, allowing you to move in and start enjoying the lake from day one. No crowded public lake. No long drive to the boat ramp. Just step into your backyard and enjoy direct access to one of Orlando's private ski lakes. Conveniently located near Downtown Orlando, MCO, major highways, shopping, dining, and entertainment, this is an opportunity to enjoy lakefront living without sacrificing everyday convenience. At $585,000, opportunities like this are hard to replicate. If you've been waiting for a private lakefront home with a dock, privacy, an oversized lot, and room to make it your own, this is one you'll want to experience in person. Schedule your private showing and come see what life on Lake Mary Jess is all about.

5769 Rockwood Avenue, Orlando

$1,599,500

5 Beds ⋅ 5 Baths ⋅ Jessamine Beach Rep SubDv. ⋅ 32839 Zip Code

Welcome to an exceptional lakefront escape on Lake Jessamine, where modern luxury meets serene waterfront living. This beautifully renovated home showcases timeless design, high-end finishes, and over 140 feet of pristine shoreline complete with your own private boat dock, ideal for boating, fishing, or enjoying spectacular sunrise views each morning. Step inside to a bright, open-concept layout that seamlessly blends the living, dining, and kitchen areas, perfect for everyday comfort or entertaining guests. The brand new designer kitchen features sleek cabinetry, quartz-style countertops, modern appliances, and generous storage. Each bathroom has been thoughtfully redesigned with spa-inspired touches, including marble counters and elegant custom tile work. A spacious flex room adds valuable versatility, ideal for a home gym, office, media room, or game room. Outdoors, enjoy a large backyard, a relaxing covered lanai, and a durable metal roof that provides long-term peace of mind. Located in a quiet, convenient neighborhood with NO HOA, this home gives you the freedom to live, rent, or invest as you choose, while still being minutes from top schools, shopping, dining, and major highways. Words can only describe so much seeing this home in person is the only way to truly appreciate the beauty, craftsmanship, and breathtaking lakefront setting. This remarkable waterfront residence offers unmatched comfort, elegance, and lifestyle value. Schedule your private showing today!

5526 Parkdale Drive, Orlando

Start Your Search

Pine Castle FL Waterfront Homes for Sale

Pine Castle has one or two active waterfront homes on the market at any given time, so inventory here is thin. They run from $1,350,000 to $1,599,500, with a median around $1,474,750. The typical one is about 3,875 square feet with 4 bedrooms. The list above is pulled live from the MLS, so it is current even when this write-up is not.

Pine Castle waterfront homes at a glance

Active listings	one or two
Median list price	$1,474,750
Price range	$1,350,000 to $1,599,500
Median size	3,875 sq ft
Median bedrooms	4
Median year built	1958
Median days on market	331

No HOA and optional HOA are not the same thing

Most searches lump these together. They are different to live in, and the difference is worth understanding before you rule a house in or out.

No association at all	2	No HOA, no dues, no architectural approval. You answer to the county and to any deed restrictions recorded on the plat, nothing else.
Association exists, membership optional	0	There is a community association but dues and membership are voluntary. No mandatory assessment, no enforcement arm, and usually no approval process for what you do with your own house. Many owners join for the amenities and nothing happens if you do not.

Neither one carries a mandatory assessment. That is the thing most buyers are actually trying to avoid when they search for no HOA. Deed restrictions can still exist in both cases and are recorded against the plat, so read them before you write.

Pine Castle waterfront homes by price range

$1M+	2

What to check before you write an offer

Lakefront vs canal vs riverfront vs intracoastal
Flood zone and insurance
Dock permits and seawall condition
Boatable vs non-boatable water

Want any of these verified on a specific address? Call or text 407-616-9019 and we will pull it.

Frequently asked questions

How many waterfront homes are for sale in Pine Castle?

There are one or two active at any given time. The list on this page comes straight from the MLS and updates on its own.

What do waterfront homes cost in Pine Castle?

The median list price is around $1,474,750, with the range running $1,350,000 to $1,599,500.

Do waterfront homes need flood insurance?

It depends on the flood zone, not on whether the home touches water. A lender requires it in some zones and not others, and the premium varies widely. Get the elevation certificate early.

Can you show me waterfront homes in Pine Castle?

Yes. Call or text 407-616-9019 and we will set up showings.