Leesburg Homes with Pool View

Leesburg Homes with Pool View

Welcome to Leesburg, Florida, a charming city nestled in the heart of Lake County, where small-town warmth meets the beauty of nature. Known for its picturesque lakes and vibrant community, Leesburg offers a delightful blend of outdoor adventures, rich history, and modern conveniences. With its friendly neighborhoods, residents enjoy a relaxed lifestyle surrounded by stunning landscapes and recreational opportunities.

One of the standout features of Leesburg is its stunning homes with pool views. Imagine waking up each morning to the serene sight of sparkling water just outside your window. These properties not only provide a refreshing escape but also serve as the perfect backdrop for entertaining friends and family or enjoying peaceful evenings under the stars. Many of these homes boast expansive outdoor living spaces, allowing you to soak up the Florida sun while enjoying the comfort of your own oasis.

In addition to the allure of poolside living, Leesburg is home to a variety of parks, lakes, and nature trails, making it a haven for outdoor enthusiasts. Whether you prefer fishing, boating, or simply taking a leisurely stroll, there’s no shortage of activities to enjoy. The city’s rich cultural scene, featuring local festivals, art shows, and community events, ensures that there’s always something happening.

With its inviting atmosphere and beautiful homes with pool views, Leesburg is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the charm of this lovely city and find your dream home by the pool today!

Newest Leesburg Homes with Pool View

$275,000
6 Beds ⋅ 3 Baths ⋅ Leesburg SubDv. ⋅ 34748 Zip Code
ESTATE SALE — INVESTOR OPPORTUNITY, HIGHEST & BEST DEADLINE, NO CONTINGENCIES. Historic 1927 fixer-upper on 0.48 acres in the heart of Downtown Leesburg, including an additional buildable lot (1118 W line St former home site — prior impact fees paid may reduce future construction costs). 3,462 sq ft, 6 bedrooms, 3 baths, two full kitchens, large deep pool with expansive back deck. Originally used as a boarding house with separate entrances upstairs and down — incredible flexibility for renovation, multi-generational living, or income potential. Gorgeous original wood floors, soaring ceilings, rare 1927 architecture. Recent partial PVC plumbing update. Being sold by the estate, priced to sell at or above asking. Terms: Listed at $275,000. Seller requires all offers at or above asking price with NO contingencies. Buyers may inspect during the first 7 days from list date; highest and best offer due by Monday August 10, 2026. Closing required within 14 days of contract execution — earnest money due immediately upon acceptance. Sold as-is.

1116 W Line Street, Leesburg
$394,900
3 Beds ⋅ 2 Baths ⋅ Chelsea Park Sub SubDv. ⋅ 34788 Zip Code
Move-in ready, beautifully renovated, and complete with a solar-heated pool—this home delivers the Florida lifestyle without the wait. Located in the desirable, low-HOA Chelsea Park community, this 3-bedroom, 2-bath home blends modern design, upgraded finishes, and a private outdoor oasis rarely found in new construction. Roof new in 2020. A fresh, light, and bright interior welcomes you the moment you step inside. Brand-new luxury vinyl plank flooring flows throughout the expanded living and dining areas, complemented by updated light fixtures that elevate the home’s clean, modern aesthetic. The renovated kitchen is a true showpiece, featuring quartz countertops with a waterfall edge, a spacious island, breakfast bar, updated cabinetry, newer appliances, and stylish finishes that rival today’s new-build design packages. The primary suite offers a peaceful retreat with a new walk-in shower, garden tub, updated ensuite features, a generous walk-in closet, and French doors leading directly to the screened lanai—a perfect blend of comfort and luxury. Step outside to your private outdoor haven—an impressive screen-enclosed, solar-heated sparkling pool, freshly painted pool deck, and a fully fenced backyard with mature landscaping and exceptional privacy. This move-in-ready outdoor living space is a major advantage over new construction, where pools, fencing, and landscaping often require significant additional cost and long wait times. A 2-car garage provides secure parking and additional storage, rounding out the home’s functional design. Located minutes from restaurants, shopping, medical facilities, and everyday conveniences, this modern Florida pool home delivers upgraded design, a private pool lifestyle, and a prime location—an exceptional opportunity that stands out among new-build competition.

33150 Kaylee Way, Leesburg
$390,000
3 Beds ⋅ 3 Baths ⋅ Golfview Sub SubDv. ⋅ 34788 Zip Code
POOL HOME ON NEARLY HALF AN ACRE WITH NO HOA! Welcome to this spacious 3-bedroom, 2.5-bath Leesburg home offering 2,496 heated square feet, a private in-ground pool, attached 2-car garage, downstairs primary bedroom, formal dining room, interior laundry room, and a large upstairs loft. The living room features vaulted ceilings, exposed wood beams, and a stone wood-burning fireplace, creating a warm central gathering space. The kitchen offers granite-look counters, a breakfast nook, range, microwave, refrigerator, and dishwasher. Enjoy multiple outdoor living areas, including a covered rear patio, screened upper porch, poolside gazebo, storage shed, fenced yard, mature trees, and peaceful pond views. Conveniently located near US-441, shopping, dining, downtown Leesburg, and area amenities.

9916 Jackson Road, Leesburg
$82,500
3 Beds ⋅ 2 Baths ⋅ Leesburg Chesterbrook 02 Condo SubDv. ⋅ 34748 Zip Code
DISCOVER EASY FLORIDA LIVING-in the desirable Chesterbrook Condominiums in Leesburg! This centrally located 3-bedroom 2- bath home is nestled in a welcoming 55+ community featuring a community pool and clubhouse. NEW ROOF 2026, AND NEWER AC. The HOA also covers water, sewer, trash, and cable making for a truly hassle-free living. Whether you're looking for a full time residence or the perfect winter retreat , this is an opportunity you want to miss!!

500 Newell Hill Road Unit 108D, Leesburg
$649,000
3 Beds ⋅ 2 Baths ⋅ Eagles Point Sub SubDv. ⋅ 34788 Zip Code
Your Harris Chain Boating Lifestyle starts here! Experience the best of Florida waterfront living in this beautifully maintained 3-bedroom, 2-bath canal-front home with direct access to Lake Eustis and the renowned Harris Chain of Lakes. Perfectly situated on the edge of Leesburg, this move-in-ready property offers the ideal combination of comfort, convenience, and an exceptional boating lifestyle. Designed for both relaxation and entertaining, the backyard is your private oasis. Enjoy a sparkling inground pool with a tanning ledge, a spacious covered lanai, and a screened enclosure complete with a convenient dog door. The fully fenced yard offers plenty of space for children and pets to play, while the lawn irrigation system draws water directly from the canal, helping keep the landscaping lush while reducing irrigation costs. Water enthusiasts will appreciate the Trex dock with a covered boathouse and boat lift, providing effortless access to boating, fishing, sunset cruises, and all that the Harris Chain has to offer. This home has been thoughtfully updated and meticulously cared for, offering peace of mind with numerous recent improvements. Updates include interior and exterior paint, newer appliances, Trex dock decking, shutters, lighting, and professional landscaping. Major mechanical updates include a new roof (2022), new water heater (2024), new exterior AC unit (2024) and a new state-of-the-art high-efficiency AC air handler, just installed in July 2026. Whether you're searching for a year-round residence, a seasonal escape, or the perfect waterfront retreat, this exceptional canal-front home delivers everything you've been looking for—modern updates, outstanding outdoor living, and direct access to one of Central Florida's most sought-after chains of lakes. Don't miss this rare opportunity to own your own piece of the Harris Chain lifestyle!

12037 Eagle Point Ct, Leesburg
$879,000
5 Beds ⋅ 4 Baths ⋅ Silver Lake Meadows Sub SubDv. ⋅ 34788 Zip Code
THIS EXCEPTIONAL ONE OF A KIND home is located in the highly sought after SILVER LAKE MEADOWS community, with NO HOA. Situated in this mature, quiet and golf cart friendly neighborhood and near Silver Lake which is 2.9 miles around and suited for walking, running or biking. Meticulously maintained, this 5 bedroom, 4 bath residence on a high and dry .54 acre homesite, is the kind of space and privacy that you have been looking for. This beautifully custom built home offers comfort, style and incredible entertaining spaces inside and out. From the moment you enter its decorative glass front entry doors with fan light, you enter your Formal Living Room with custom lighting, bamboo floors and crown molding, which opens up a view of a beautiful pool, lanai and firepit in your private fenced and Oak shaded back yard. A Formal Dining Room with decorative lighting, trey ceilings, Plantation shutters, and bamboo floors is exquisite. Right of the entryway is an office, den or bonus room with Plantation shutters, bamboo floors and beautiful trey ceiling. Moving on to the Kitchen, Family Room and Dinette area is an Aquarium Glass window for the perfect view of your private yard, resort style pool and lanai. Crown molding is found throughout with ceramic tile floors in the Kitchen, Family Room and Dinette area. The Gourmet Kitchen features chiseled leather granite countertops, Kitchen Island with granite, Stainless appliances, new lighting feature over the island, and new touch water faucet, gas range, and wine bar with refrigerator, built-in wine rack and walk in pantry. The Family Room has a gas fireplace with heat and glow fire concrete composite, 2 zone surround sound system and French door to pool deck. The Laundry Room has ceramic tile floors, cabinets below with laundry sink and cabinets above washer and dryer. A spacious 14 x 19 Master Suite with new carpet, and crown molding has French doors that open to the Lanai with a private gas fireplace. The Primary Bath has ceramic tile floors, His and Her Walk in Closets, separate vanities, garden tub and separate shower with Rain head, crown molding, separate water closet and Plantation Shutters. The Second and Third Bedrooms have new carpet and are connected with a Jack n Jill Bath. A large Fourth Bedroom is 15 x 19 above the Garage, with carpet, separate full bath with tile, tub & shower, and separate Walk-in-closet with attic access. There is a Fifth Bedroom that was added to one of the garage bays 10 x 17, with laminate floors, closet and split system HVAC. The 16 x 44 screened Pool Lanai has been freshly painted, and features an Outdoor Wet-bar with chiseled granite counter. The resort style pool with stone and waterfall hot tub, and lighting that changes colors for relaxing and entertaining. The Separate Paver Fire-pit offers seating, lighting and a power outlet. There is a poured and scored Concrete area 14 x 21 for your grilling area which is covered. There is an additional Concrete pad for a storage building, or gaming area. The enclosed backyard, backing up to a retention area, has majestic oak trees, azaleas, and beautiful landscaping. The attention to detail shows in every aspect of this beautiful home.

34028 Matthews Cove, Leesburg
$1,775,000
5 Beds ⋅ 5 Baths ⋅ Leesburg Palmora Park SubDv. ⋅ 34748 Zip Code
A rare opportunity to own one of Leesburg’s iconic lakefront estates, offering 164 feet of direct frontage on Lake Harris and set on a beautifully positioned 1.24-acre corner lot. This exceptional property delivers unmatched curb appeal with its stately presence, circular drive, mature landscaping and timeless architectural charm. The main residence spans nearly 5,000 square feet and has been thoughtfully updated to blend classic elegance with modern comfort. The 2020-renovated kitchen serves as the heart of the home, complemented by updated bathrooms throughout. Offering five bedrooms and 4.5 baths, the layout is ideal for everyday living and hosting guests. A private mother-in-law suite with its own fully equipped kitchen provides flexibility for extended family or long-term guests, while a detached efficiency apartment above the garage creates additional living space or an excellent income-producing opportunity. Designed for relaxation and recreation, the outdoor living experience is resort-style. Enjoy a recently renovated heated pool and spa, expansive patio areas, and sweeping lake views that create a backdrop for entertaining or quiet evenings at home. The private boathouse with dock and lift provides effortless access to the Harris Chain of Lakes, making this a dream setting for boating enthusiasts. Within city limits in a golf cart-friendly area, the home offers a blend of privacy and convenience, just minutes from downtown Leesburg dining, shopping and waterfront parks. With its expansive homesite, impressive 164 feet of shoreline and premier lakefront amenities, this is a one-of-a-kind offering that captures the best of Florida waterfront living.

405 Lakeshore Drive, Leesburg
$1,395,000
5 Beds ⋅ 4 Baths ⋅ N/A SubDv. ⋅ 34748 Zip Code
Welcome to your lakefront retreat designed for those who love to host, relax, and live life in style. Nestled on 1.66 acres along the shores of Lake Harris, part of Florida’s highly sought-after Chain of Lakes, this 4,420+ sq ft, 5-bedroom, 4-bath home exudes classic Florida charm. It provides comfort, thoughtful updates, and exceptional outdoor amenities for a resort-style estate. Enjoy 150 feet of direct waterfront with your private boathouse featuring a 418 sqft, upper-level guest apartment and balcony overlooking the lake, perfect for friends or weekend visitors. Spend your days boating, fishing, or exploring miles of scenic waterways, then unwind poolside or enjoy a twilight match on your private lighted tennis court. The outdoor experience is truly resort-caliber, highlighted by a sparkling pool surrounded by an entertainment deck and $90,000 in professional landscaping and lighting enhancements that elevate the property’s beauty day and night. Mature oaks, manicured grounds, and custom illumination create a warm, inviting ambiance ideal for gatherings and peaceful evenings by the water. Inside, the home exudes comfort and relaxation. The formal living area features a beautifully renovated stone fireplace, thoughtfully transformed from its original brick design to create a timeless focal point. The heart of the home, a spacious entertainer’s kitchen is perfectly designed for dinner parties and gatherings, with generous counter space, dual islands, quartz countertops, modern appliances, a large walk-in pantry and a seamless open layout connecting to multiple living and dining areas, this kitchen makes entertaining effortless and functional. With 5 bedrooms and 4 full baths, the home offers flexibility for family and guests. The primary bedroom is expansive with a large L-shaped walk-closet. Additional spaces include formal and casual living areas, a home office, and a flex room. The three-car garage provides abundant space for vehicles and storage. Located on a quiet dead-end street, the property offers privacy and tranquility while remaining just minutes from shopping, dining, and entertainment. Recent upgrades within the last five years include: $90,000 in Landscaping and lighting, two new HVAC systems, replaced well and sprinkler pumps, a well water treatment system, new outdoor privacy fence, rescreened pool deck, new hot water heaters in both the main home and boathouse, new boathouse roof with portable A/C, metal roof maintenance on the main home (screws and boots replaced), and fresh interior paint in multiple rooms. The kitchen has been extensively updated with a new refrigerator, dual oven, stovetop, sink, faucets, island countertop, and cabinet hardware—plus numerous additional improvements enhancing comfort, efficiency, and style. Live the ultimate Florida lifestyle—launch your boat from your private dock, take a refreshing swim, or host unforgettable gatherings under the stars. Nearby attractions include Mission Inn Resort & Club (championship golf, spa, and dining), Yalaha German Bakery & Beer Garden (a local favorite for brunch and live music), Lakeridge Winery (Central Florida’s premier vineyard and festival destination), Venetian Gardens Park (waterfront trails, marina, and community events), and The Villages, offering world-class shopping, dining, and nightly entertainment. Conveniently located minutes from the Florida Turnpike and 441, to all major attractions, and Orlando Airport(MCO)

4345 Corley Island Road, Leesburg
$185,000
2 Beds ⋅ 3 Baths ⋅ Leesburg Royal Oak Estates Sub SubDv. ⋅ 34748 Zip Code
GATED Community, Private Patio, UPDATED kitchen, New HVAC, desirable location Across from POOL and Fitness Center, 2 Master suites, includes ALL APPLIANCES. Best location in the neighborhood. This townhome is very spacious and features nearly 1300 sq ft of living space excluding the courtyard, plus 2 bedrooms and 2 1/2 baths. Great layout with an open and updated kitchen with sliding glass doors to patio. Living room and dining area are mirrored creating the illusion of massive rooms and there is a 1/2 bath downstairs for your guests. Both bedrooms are upstairs each with a balcony overlooking patio and each with its own private bath. Two private reserved parking spaces. Washer and dryer included along with clicker for gate. NO MONEY DOWN FINANCING AVAILABLE !!! CALL TO SCHEDULE A TIME TO SEE TODAY

2942 Poplar Avenue, Leesburg
$3,500,000
6 Beds ⋅ 8 Baths ⋅ Johnsons Mary K & T S SubDv. ⋅ 34748 Zip Code
Experience a rare blend of serenity, sophistication, and lakefront living on the pristine shores of Lake Harris, part of Central Florida’s famed Harris Chain of Lakes. Tucked behind a private gated drive, this extraordinary property spans 3.06 acres with the added benefit of 46± acres of protected conservation land, creating a sense of unrivaled privacy and natural beauty. Inside the 8,596-square-foot custom residence, craftsmanship takes center stage. Walls of windows capture shimmering water views from nearly every room, while rich design details, from diagonal-laid hardwood floors and porcelain tile to tongue-and-groove, barrel, coffered, and tray ceilings, set an elegant tone. Handcrafted millwork, a stunning leaded glass entry, granite surfaces, multiple fireplaces, and upscale finishes add warmth and timeless appeal. The home was designed for both quiet moments and unforgettable gatherings. An open chef’s kitchen flows into welcoming dining and living areas, perfect for entertaining. Additional spaces include a first-floor game room with its own chilled wine room, a private office with custom woodwork, a dedicated homework station, and a versatile bonus room over the garage, ideal for a theater, guest suite, fitness area, or creative retreat. Each bedroom features a private ensuite bath, offering comfort and privacy for family and guests alike. Step outside to an outdoor haven where you can wander a serene path to a lakeside firepit, relax by the pool, or enjoy your private boathouse with dual lifts for effortless days on the water. The expansive, beautifully landscaped grounds have even hosted picturesque weddings, making this estate as enchanting for events as it is for everyday living. All this tranquility comes with surprising convenience. You’re moments from charming downtown Leesburg and Mount Dora, with nearby golf, shopping, dining, and healthcare options such as UF Health and AdventHealth. Leesburg International Airport is close at hand, while Disney and Orlando International Airport are less than an hour away. This is more than a home, it’s a private lakeside retreat designed for refined living, effortless entertaining, and unforgettable memories.

30215 Redtree Drive, Leesburg
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