Leesburg Homes with Pool Community Features

Leesburg Homes with Pool Community Features

Welcome to Leesburg, Florida—a charming city nestled in the heart of Lake County, where Southern hospitality meets a vibrant community spirit. Known for its picturesque lakes and lush landscapes, Leesburg offers a delightful blend of small-town charm and modern amenities. With its rich history, diverse recreational opportunities, and a welcoming atmosphere, it’s no wonder that Leesburg is a sought-after destination for families, retirees, and everyone in between.

One of the standout features of Leesburg is its array of beautiful homes with pool community options. Imagine coming home to your very own oasis, where you can unwind in the refreshing waters of your private pool or enjoy sunny afternoons lounging poolside with friends and family. These communities are designed with your lifestyle in mind, offering not just homes but a vibrant way of life. Many neighborhoods boast additional amenities such as clubhouses, fitness centers, and walking trails, all while fostering a sense of camaraderie among residents.

Beyond the allure of poolside living, Leesburg is also home to a plethora of parks, lakes, and recreational activities. Whether you’re exploring the scenic shores of Lake Harris, indulging in local dining, or attending community events, there’s always something happening in this dynamic city.

Discover the charm of Leesburg, where your dream home with pool awaits, and experience a community that truly feels like home. Let the sunshine and warm breezes of Florida enhance your lifestyle in this idyllic setting!

Newest Leesburg Homes with Pool Community Features

622 Cottage Park Lane, Leesburg
$139,500
1 Beds ⋅ 1 Baths ⋅ Pennbrooke Ph 01a SubDv. ⋅ 34748 Zip Code
Welcome to easy Florida Living in this well-maintained, gated 55+ Golf Community!! This charming cottage-style home offers a comfortable, low-maintenance lifestyle and is conveniently located near shopping, medical facilities, dining, and entertainment in The Villages - all approximately 10 minutes away. Recent updates include a new 30-year shingle roof with a one time 10 year transferrable warranty (August 2026), high capacity Heat Pump Air-Conditioning system (May 2025), luxury plank vinyl flooring throughout and fresh interior paint. The home is move in ready, while still offering the perfect opportunity to add your own personal touches. If that's not enough, there is a restaurant on property and an RV/Boat Storage facility including a wash and dump station. Best of all, this bright and welcoming home is filled with natural light and is being sold furnished, making your transition even easier. Whether you are looking for a full time residence or a Florida retreat, this delightful home is ready to welcome you! Don't miss the opportunity to make this lovely cottage your home. ***ITEMS THAT DO NOT CONVEY***Picture of the lady on the turquoise wall, Picture in the bedroom, and the new stainless steel-silverware.

622 Cottage Park Lane, Leesburg
21516 Castle View Court, Leesburg
$380,000
3 Beds ⋅ 2 Baths ⋅ Royal Hlnds Ph 1-D SubDv. ⋅ 34748 Zip Code
SELLER INCENTIVE! Seller will contribute up to 3% of the purchase price toward buyer’s allowable closing costs, prepaids and/or interest-rate buydown with a full-price offer, subject to lender guidelines. BEAUTIFULLY RENOVATED AND MOVE-IN READY in Royal Highlands, a gated 55+ golf community in Leesburg! This impressive 3-bedroom, 2-bath home features a BRAND-NEW ROOF installed in September 2026 and offers 1,798 sq. ft. of living area under air and 2,830 sq. ft. of total area, combining generous indoor and outdoor spaces with extensive recent improvements. Step inside to a bright, fresh interior where the renovation is immediately evident. The home features new plank-style flooring throughout the main living areas and bedrooms, fresh interior paint, updated lighting and ceiling fans, modern fixtures and hardware, and beautifully refreshed living spaces. The open living and dining areas provide an inviting setting for everyday living and entertaining. The completely updated kitchen is a centerpiece of the home, featuring white shaker-style cabinetry, beautiful countertops, contrasting hardware, stainless-steel appliances, abundant cabinet and counter space, and a convenient breakfast bar. Both bathrooms have also been extensively renovated. The spacious primary suite features a beautifully remodeled bath with dual vanities, contemporary mirrors and fixtures, soaking tub and separate shower. The guest bathroom carries the fresh, modern finishes throughout the home. A dedicated interior laundry room provides additional convenience. One of the home's most enjoyable features is the large enclosed Florida room, surrounded by windows and providing wonderful additional space for entertaining, hobbies, reading, morning coffee or simply enjoying the Florida sunshine year-round. Additional screened, covered and outdoor areas further extend the home's versatility. Garage space is another major advantage: an attached 2-car garage PLUS a dedicated golf-cart garage—an especially desirable feature in this golf-cart-friendly community. The home is situated on an attractive corner lot near the beginning of a cul-de-sac, with mature landscaping and generous outdoor space. Royal Highlands offers an exceptional Florida lifestyle with an 18-hole golf course, clubhouse, indoor and outdoor pools, fitness center, pickleball, tennis, bocce, shuffleboard, softball, billiards, restaurant, pro shop, numerous clubs and an active calendar of social activities. Everyday conveniences are within easy reach, including shopping, restaurants, groceries and medical services, with convenient access to US-27 and Florida's Turnpike. Enjoy historic Leesburg, the Harris Chain of Lakes and Venetian Gardens waterfront, or head south toward Clermont and the greater Orlando area, including Central Florida's world-famous attractions and Orlando International Airport. NEW ROOF. EXTENSIVE RENOVATION. 2-CAR PLUS GOLF-CART GARAGE. SELLER CONTRIBUTION AVAILABLE WITH FULL-PRICE OFFER. Schedule your private showing today!

21516 Castle View Court, Leesburg
5418 Barnwell Court, Leesburg
$349,000
2 Beds ⋅ 3 Baths ⋅ Plantation At Leesburg Riverside Village SubDv. ⋅ 34748 Zip Code
Welcome to this beautifully maintained, one-owner home located in the sought-after 55+ community of The Plantation at Leesburg. Situated on a desirable corner lot, this spacious home offers a versatile floor plan with two primary bedrooms, each featuring its own en-suite bathroom, plus a separate den that could easily serve as a third bedroom, office, or hobby room. An additional half bath provides convenience for guests. The home features a separate living room, dining room, and family room, providing plenty of space for entertaining or relaxing. The family room overlooks the beautifully landscaped backyard, creating a peaceful setting to enjoy the Florida lifestyle. A charming breakfast nook offers the perfect spot for casual morning meals. Step outside to the large, screened lanai, an ideal place to enjoy your morning coffee, entertain friends, or unwind while taking in the beautiful surroundings. Additional features include Corian countertops, an inside utility room, and an abundance of well-maintained living space. Major updates include a new roof installed in 2024 and a top-of-the-line 4-ton, two-stage HVAC system installed in 2023, providing added comfort and efficiency. This home has been lovingly cared for by its original owner and is truly move-in ready. Furniture is also negotiable, offering buyers the opportunity for a convenient, furnished transition into their new Florida home. Located in The Plantation at Leesburg, residents enjoy a vibrant 55+ lifestyle with an array of amenities, activities, and opportunities to enjoy everything Central Florida has to offer.

5418 Barnwell Court, Leesburg
4431 Nottoway Drive, Leesburg
$260,000
3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Nottoway Village SubDv. ⋅ 34748 Zip Code
Welcome to 4431 Nottoway Drive, a spacious 3-bedroom, 2-bath home with 1,751 square feet of living space and a 2-car garage, located in Nottoway Village within The Plantation at Leesburg, a gated 55+ golf community. With a NEW ROOF in 2024 and NEW HVAC in 2025, two of the home's major systems have already been updated. Inside, the light and bright floor plan features tall ceilings in the living room and kitchen, creating an open and spacious feel. The living area is centered around a propane fireplace, while the kitchen overlooks the main living space and offers plenty of cabinetry and counter space, making it easy to stay connected while cooking or entertaining. A separate dining area provides additional space for gathering with family and friends. The spacious primary suite features direct access to the screened lanai, generous closet space and an en-suite bath. The second bedroom provides comfortable space for guests, while the third room is ideally suited as a study, den, office or hobby room. You'll also appreciate the indoor laundry room and abundant storage, including a large walk-in pantry/storage area. Multiple sliding glass doors connect the interior to the expansive SCREENED LANAI, creating an inviting extension of the living space and a comfortable place to enjoy Florida's year-round lifestyle. Mature landscaping and established trees add to the home's setting. Residents of The Plantation at Leesburg enjoy an active lifestyle with 36 holes of golf, The Oaks Bar & Grill, multiple pools, fitness centers, hot tubs, pickleball, tennis, softball, bocce, shuffleboard, archery, horseshoes, cornhole, activity halls, a woodworking shop, library, art room, billiards and a wide variety of clubs and activities. Whether you're enjoying a morning round of golf, relaxing on the screened lanai, meeting friends for dinner or taking advantage of the many amenities, 4431 Nottoway Drive offers an opportunity to enjoy the Florida lifestyle in one of Leesburg's established 55+ communities. Schedule your private showing today!

4431 Nottoway Drive, Leesburg
4711 Heritage Trail, Leesburg
$535,000
2 Beds ⋅ 2 Baths ⋅ Arlington Ridge SubDv. ⋅ 34748 Zip Code
Love to travel? Then you’re going to want to see where you can park the RV when you get home. This turnkey property is ready for you to simply bring your bags and move in. As one of the few homes in Arlington Ridge with an RV garage, this property gives you the freedom to keep your RV or motorcoach right at home. The oversized RV garage features a 12' wide x 14' high door and generous space that can be adapted to suit your lifestyle, whether that means an RV, boat, classic car, motorcycles, extra storage, or a workshop. And because the RV garage is in addition to a separate two-car garage, there’s no need to choose between the things you love and the space to keep them. The community RV clean-out station is just down the street, adding another layer of convenience for your next adventure. Inside, the home is as inviting as its setting, with a kitchen that opens to the living room and a charming Tuscan-inspired courtyard tucked between the home and RV garage. A gas stone fireplace, gas-lit wall sconces, wrought-iron gate, and potted lemon and lime trees create a private outdoor space that feels made for morning coffee, evening conversations, or unwinding after a day on the road. With no rear neighbors, the backyard offers an added sense of privacy, and HOA-approved pool renderings are available from the seller for those considering a future pool. Recent improvements include a 2023 roof and 2026 A/C unit. Arlington Ridge is a 55+ community designed to keep life active, social, and fun, with golf, pickleball, tennis, swimming, fitness, walking and biking trails, dining, arts and crafts, live entertainment, and more. HOA fees include lawn maintenance, Fiber Now/OpticalTel Cable TV and Internet, and access to the back gate. The CDD covers the golf course, restaurant, additional amenities, common areas, and 24/7 guarded front gate. Conveniently located minutes from the Florida Turnpike, grocery stores, restaurants, businesses, and hospitals, this is a place designed around the freedom to travel while still having a great place to come home to. Schedule your private tour and see how well this home fits the lifestyle you’ve been looking forward to.

4711 Heritage Trail, Leesburg
4513 Antietam Creek Trail, Leesburg
$437,500
3 Beds ⋅ 3 Baths ⋅ Arlington Rdg SubDv. ⋅ 34748 Zip Code
RARE FIND IN ARLINGTON RIDGE: 3-CAR GARAGE | NEW ROOF 6/2026 | TWO MASTER SUITES | DOUBLE OVEN | GOLF COURSE FRONTAGE. Discover a lifestyle of comfort and leisure you’ve waited your whole life for in this charming home located in the popular, high-demand 55+ active adult, guard-gated community of Arlington Ridge. Designed for luxurious, low-maintenance living with stucco construction and a low HOA fee of just $126 per month, this property is the ultimate retreat. FOUR PRIME HIGHLIGHTS: **THE 3 CAR GARAGE: Features ample room for vehicles, golf carts, and extra storage, over 700 sq ft complete with a screened garage door enclosure. **THE TWO MASTERS: Includes two full master suites (ideal for an in-law suite or multi-generational living), each featuring en-suite baths, step-in Roman showers for safety, private water closets, and expansive walk-in closets. **THE DOUBLE OVEN: Gourmet kitchen built for hosting, featuring rich wood cabinets, quartz countertops, a closet pantry, upgraded stainless steel appliances, and a convenient extra wall oven. **THE GOLF COURSE FRONTAGE VIEW: Step through sliding glass doors to your 450 sq. ft. golf-front, always-shady lanai overlooking the fairway, plus two paver patios perfect for grilling and watching sunsets. INTERIOR & ENERGY HIGHLIGHTS: Zero Carpet: 9-foot ceilings and sleek engineered hardwood & tile flooring throughout. Open-Concept Layout: High ceilings seamlessly connect the Great Room, dining area, and chef's kitchen. Turnkey Ready: Indoor laundry room with washer and dryer included. Major Insurance Savings: High construction standards built to modern wind codes, high elevation for flood protection, and low-wind zone status qualify this home for lower). UNBEATABLE HOA VALUE ($126/MONTH INCLUDES): Full lawn care (mowing, edging, and blowing). High-speed 250MB Wi-Fi with router coverage throughout the home. 200+ Cable TV channels with 2 DVRs included RESORT-STYLE COMMUNITY AMENITIES: Located just a 5-minute golf cart ride to the community center: 18-hole championship golf course with year-round tee times (NO mandatory social or golf membership required!). Driving range & putting greens. Heated swimming pools, hot tub, and state-of-the-art fitness facilities. Lighted tennis & pickleball courts, billiards, and a free movie theater. On-site restaurant and tavern. Nearby free boat ramp and fishing pier on a 15,000-acre lake (5 minutes away). Conveniently located near grocery stores, banks, pharmacies, and dining. Just 20 minutes from regional malls and a 12-screen movie theater, 45 minutes from Orlando, major theme parks, and the airport, and 90 minutes from both Daytona Beach and Clearwater!

4513 Antietam Creek Trail, Leesburg
11 Hawaiian Way, Leesburg
$69,900
2 Beds ⋅ 1 Baths ⋅ Molokai Co-Op SubDv. ⋅ 34788 Zip Code
This 2-bedroom, 1-bathroom home is perfectly sized for a new homeowner in the 55+ Molokai Co-Op community, where you own the land with no lot rent. The home features updated flooring throughout and new cabinetry in the kitchen. The inviting Florida Room is ideal for relaxing and enjoying the beautiful Florida surroundings. While you’re here, be sure to explore the community amenities, including the clubhouse, pool, and a variety of clubs you can join to make the most of life in the park.

11 Hawaiian Way, Leesburg
408 Palo Verde Drive, Leesburg
$129,900
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Welcome to easy Florida living in this beautifully maintained 2-bedroom, 2-bath home offering 1,236 square feet of comfortable living space. Bright, inviting, and filled with natural light, this home has been thoughtfully cared for and is ready for its next owner. The spacious living room is highlighted by impressive panoramic windows that create an open, airy feel and provide plenty of natural light. Fresh interior finishes, attractive ceiling fans, updated light fixtures, and beach-inspired touches give the home a relaxed Florida style. One of the standout features is the enclosed Florida room with glass windows and heat, providing additional year-round space for relaxing, entertaining, hobbies, or enjoying your morning coffee. The well-maintained kitchen offers a functional layout with plenty of room for everyday meal preparation. Both bedrooms are comfortably sized, with the primary suite featuring a private bath with walk-in shower. The guest bathroom includes a tub, offering added convenience for visitors. A large laundry room provides valuable additional storage space. Outside, the long driveway, vinyl siding, and refreshed exterior add to the home’s curb appeal. Additional improvements include newer windows, a well-maintained roof-over, and a 2022 HVAC system. Whether you are searching for a full-time Florida residence or a seasonal getaway, this home offers comfort, functionality, and plenty of space to enjoy. Located in Hawthorne at Leesburg, a gated, resident-owned 55+ cooperative waterfront community, residents enjoy an impressive selection of amenities and activities. The $397 monthly maintenance fee includes water, sewer, lawn mowing, private emergency services, and secure storage for RVs, boats, and trailers. The community clubhouse features seating for approximately 550, a full-time program coordinator, and more than 100 activities, along with a hospitality lounge, card rooms, craft and fine arts rooms, billiards, fitness center, and library. Residents can also enjoy an outdoor geothermal-heated pool, two enclosed therapeutic pools, excellent fishing, beautifully landscaped grounds, lakes with illuminated fountains, and a relaxing gazebo. Hawthorne’s private, marina offers 120 boat slips with direct access to the Harris Chain of Lakes and beyond.

408 Palo Verde Drive, Leesburg
4512 Inverness Drive, Leesburg
$309,900
3 Beds ⋅ 2 Baths ⋅ Royal Highlands Ph 01d SubDv. ⋅ 34748 Zip Code
Virtually Staged. Tucked on a cul-de-sac in the gated 55+ community of Royal Highlands, this expanded Balmoral offers a peaceful conservation setting with no rear neighbors. The 3-bedroom, 2-bath home has 1,559 square feet of living space and solid surface flooring throughout, including engineered hardwood and ceramic tile. The eat-in kitchen features a breakfast bar, closet pantry, built-in microwave and recessed lighting. It opens to a spacious great room with sliding doors to the screened lanai, where vinyl stacking windows and a convenience bar with a refrigerator make the space easy to enjoy in every season. An adjoining patio offers another spot to relax outdoors and take in the natural setting. The primary suite includes a walk-in closet, jetted tub, separate shower and dual-sink vanity. An inside laundry room leads to the two-car garage, while plantation shutters and a screened front entry add to the home’s appeal. All appliances, the water heater and the HVAC system have been replaced within the last five years. Royal Highlands offers indoor and outdoor pools, pickleball and a convenient Leesburg location near the Florida Turnpike.

4512 Inverness Drive, Leesburg
5384 Aurora Drive, Leesburg
$525,000
3 Beds ⋅ 3 Baths ⋅ Leesburg SubDv. ⋅ 34748 Zip Code
Picture your mornings starting on your own private, second-story balcony, sipping coffee as the sun rises over the quiet woods behind your home. Located in one of Leesburg’s premier communities, this beautiful property welcomes you with a picture-perfect paver driveway, a cozy front porch, and the effortless upkeep of premium Rhino Shield exterior paint. Inside, warm, real hardwood floors flow through an open and airy layout. Step into a light-filled gourmet kitchen where baking and hosting feel effortless. Crisp double ovens stand ready for holiday meals, while a generous central island and breakfast bar invite friends to pull up a stool and chat while you cook. This beautiful space flows naturally into a formal dining room, making it easy to transition from casual meal prep to elegant candlelit dinners. Downstairs also features a cozy fireplace in the living room and a bright, dedicated office that could easily become a fourth bedroom or a creative studio. The layout offers a rare and luxurious setup with two separate primary suites. The main-floor suite is perfect for guests, while the upstairs serves as your ultimate personal sanctuary, complete with a charming reading loft. When it's time to unwind, step out into the massive, screened-in lanai. With a dramatic two story screen and a backyard that backs right up to the trees with no rear neighbors, it feels like your own private, peaceful oasis. Welcome home.

5384 Aurora Drive, Leesburg
29496 Caspian Street, Leesburg
$284,900
3 Beds ⋅ 2 Baths ⋅ Lake Denham Estates SubDv. ⋅ 34748 Zip Code
Welcome to Lake Denham Estates, where this immaculate 3-bedroom, 2-bath Jemison offers a USDA 0% down financing option for qualified buyers, along with seller-offered closing cost assistance. Beautiful curb appeal welcomes you into 1,645 square feet of thoughtfully designed living space. A spacious entry and wide hallways lead to an open living and dining area overlooking the expansive, fully fenced backyard. The kitchen offers abundant cabinet space, a large walk-in pantry, and a gas range. A dedicated laundry room, ample storage, smart home features, a sprinkler system, and a tankless gas water heater add everyday convenience. The desirable split floor plan gives everyone room to spread out. One bedroom and a full bath sit in their own wing, while another bedroom with French doors makes a wonderful guest room or home office. The spacious primary suite features a walk-in closet and an en suite bath with double sinks, a private water closet, and a walk-in shower. Out back, the covered lanai is the perfect place to relax and enjoy the generous yard. Lake Denham Estates offers a community pool overlooking a conservation area and a playground, with shopping, dining, and major Central Florida routes nearby. Whether you’re searching for a primary residence, second home, or investment property, come see all this home has to offer. Schedule your private showing today and ask about the available financing and closing cost options!

29496 Caspian Street, Leesburg
107 Diamond Head Drive, Leesburg
$103,000
2 Beds ⋅ 2 Baths ⋅ Molokai Co-Op SubDv. ⋅ 34788 Zip Code
Welcome to 107 Diamond Head Drive in the 55+ resident-owned Molokai community! This 2-bedroom, 2-bathroom home offers a pond view and an enclosed Florida room providing additional flexible living space. Enjoy the amenities of this active community, including a swimming pool, shuffleboard court, clubhouse, and much more. Conveniently located in Leesburg near shopping, dining, recreation, and everyday conveniences. Whether you're looking for a comfortable full-time residence or a place to enjoy the Florida lifestyle, this home offers the opportunity to become part of an established 55+ resident-owned community.

107 Diamond Head Drive, Leesburg
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