Location: Leesburg , 34748
Do Not Show Listings
33236 GRAND CYPRESS WAY, LEESBURG, FL 34748
$279,247501 Days on yellowkey MLS ID: G5089755
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1598 Built: 2003Monthly Fee: $265 Tax: $3,053 (2023)Community: Pennbrooke FairwaysSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,053
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Welcome to Pennbrooke Fairways, a 55+ Community! This hidden gem of a community is located just 5 minutes south of The Villages, less than an hour to Orlando, Tampa and Daytona Beach within 90 minutes... just a perfect location for day trips! Pennbrooke Fairways golf course offers golfers two executive nines and one regulation nine. Golfing packages are available for community residents and open to the public. Pennbrooke offers RV and Boat Storage with Dump & Wash Stations and 24-hour Gated, Guarded Security. The community center offers a Hair Salon, Library and Real Estate Community Office onsite. Your HOA includes cable, internet and lawn cutting services. 55+ only community with pools, club recreational centers, 3 golf courses, restaurant, pub, walking trails, pickleball, shuffleboard and much more! Loads of fun activities are planned throughout the year! Conveniently located within minutes of The Villages and Brownwood Town Square... enjoy all the shopping and dining the Villages has to offer and just minutes to Downtown Leesburg. Central Florida living at its best! THIS HOME IS A MUST VISIT!! UNEXPECT THE UNEXPECTED! The view of this home is spectacular to say the least! 3/2 home with oversized birdcage offers much to your outdoor living space! Plenty of room for you to create an outdoor oasis!! Beautiful flooring in main Living room area, and Florida room which is encased with stunning glass windows. There is a custom built pantry that features pull out shelving. You will enjoy the front screen enclosure, Open floorplan, and the VIEW! The birdcage area also has room for a hot tub. Lots of privacy and nature abounds! MUST SEE THIS HOME! ROOF 2019 AC 2024
Listing is courtesy of: MAXREV LLC (904-460-2789)
Listing Agent: Jayne Marvin (352-205-5379)
32747 TIMBERWOOD DR, LEESBURG, FL 34748
$229,24783 Days on yellowkey MLS ID: G5107140
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1504 Built: 1999Monthly Fee: $265 Tax: $2,015 (2025)Community: Pennbrooke FairwaysSingle Family
Taxes:$2,015
Tax Year: 2025
Remarks: WATER VIEW! BEAUTIFUL LANDSCAPING! PLENTY OF UPGRADES! EXPECT THE UNEXPECTED! This adorable 2/2 home has lots of upgrades. There is NO CARPETING in the main living areas. You have newer appliances in your eat in kitchen-where plenty of sunlight shines in. The VIEW is what will draw you in. You have a beautiful backyard space that opens to the WATER VIEW. Nature at its best! Welcome to Pennbrooke Fairways, a 55+ Community! This hidden gem of a community is located just 5 minutes south of The Villages, less than an hour to Orlando, Tampa and Daytona Beach within 90 minutes... just a perfect location for day trips! Pennbrooke Fairways golf course offers golfers two executive nines and one regulation nine. Golfing packages are available for community residents and open to the public. Pennbrooke offers RV and Boat Storage with Dump & Wash Stations and 24-hour Gated, Guarded Security. The community center offers a Hair Salon, Library and Real Estate Community Office onsite. Your HOA includes cable, internet and lawn cutting services. 55+ only community with pools, club recreational centers, 3 golf courses, restaurant, pub, walking trails, pickleball, shuffleboard and much more! Loads of fun activities are planned throughout the year! Conveniently located within minutes of The Villages and Brownwood Town Square... enjoy all the shopping and dining the Villages has to offer and just minutes to Downtown Leesburg. Central Florida living at its best! HVAC 2025, REROOF 2019, FURNITURE IS NEGOTIABLE
642 GLEN OAKS DR, LEESBURG, FL 34748
$214,247236 Days on yellowkey MLS ID: G5100872
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1632 Built: 1994Monthly Fee: $265 Tax: $1,999 (2024)Community: Pennbrooke FairwaysSingle Family
Taxes:$1,999
Tax Year: 2024
Remarks: Welcome to 642 Glen Oaks, nestled in the heart of Leesburg, Florida—a home where comfort meets simplicity. This inviting residence offers a rare opportunity to enjoy peaceful living with no homes behind, granting you added privacy and tranquil views from your backyard. Step inside to discover a practical floor plan for this 2 bedroom and 2 bathroom home enhanced with easy-care tile and laminate flooring throughout, ensuring both durability and effortless cleaning. While the home is in its original condition with no recent updates, it presents a wonderful canvas for your personal touch and creative vision. Enjoy bright, open living spaces perfect for gathering with friends or relaxing after a long day. The kitchen and bathrooms maintain their classic charm, allowing you to move in and settle comfortably or plan your dream renovations at your own pace. Your laundry room is inside as well. Outside, unwind in the backyard oasis, creating a serene natural backdrop—no neighbors to interrupt your view. This unique setting is perfect for morning coffee, outdoor dining, or simply savoring Florida’s beautiful weather. Additional features include a spacious driveway, 2 car garage, low-maintenance landscaping, and a friendly neighborhood atmosphere. Welcome to Pennbrooke Fairways - a 55+ gated guarded community! This hidden gem of a community is located just 5 minutes south of The Villages, less than an hour to Orlando, Tampa and Daytona Beach within 90 minutes... just a perfect location for day trips! Pennbrooke Fairways golf course offers golfers two executive nines and one regulation nine. Golfing packages are available for community residents and open to the public. Pennbrooke offers RV and Boat Storage with Dump and Wash Stations & 24-hour Gated Security. The community center offers a Restaurant, Hair Salon, Library and Real Estate Community Office onsite. Your HOA includes cable, internet and lawn cutting services. Guarded, gated community with pools, club recreational centers and more. Loads of fun activities are planned throughout the year! Conveniently located within minutes of The Villages and Brownwood Town Square... enjoy all the shopping and dining the Villages has and just minutes to Downtown Leesburg. Central Florida living at its best! ROOF 2013 HVAC 2024
610 COTTAGE PARK LN, LEESBURG, FL 34748
$89,24776 Days on yellowkey MLS ID: G5107513
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 432 Built: 1987Monthly Fee: $265 Tax: $409 (2025)Community: Pennbrooke FairwaysManufactured Home
Taxes:$409
Remarks: One or more photo(s) has been virtually staged. Discover Your Perfect Central Florida Retreat at Pennbrooke Fairways! Nestled just 5 minutes south of The Villages, this hidden gem offers the ultimate in convenient Florida living. Whether you're dreaming of day trips to Orlando, Tampa, or Daytona Beach—all within 60-90 minutes—or simply enjoying everything this vibrant community has, you'll be perfectly positioned for the lifestyle you've been imagining. Golf enthusiasts will appreciate the exceptional Pennbrooke courses featuring two executive nines and one regulation nine, with packages available exclusively for residents and open to the public. Beyond the greens, Pennbrooke Fairways truly shines with its thoughtful amenities: secure RV and boat storage complete with dump and wash stations, 24-hour gated security for peace of mind, and a welcoming community center housing a hair salon, library, and on-site real estate office—all just steps from your door! Your HOA fees work hard for you, too -- covering cable, internet, and lawn cutting services. Take a refreshing dip in one of the sparkling pools, gather with neighbors at the recreational centers, or join in the calendar full of engaging activities planned year-round. The location truly can't be beat—minutes from The Villages and Brownwood Town Square for nightly entertainment, shopping and dining, and a short drive to charming Downtown Leesburg. With an exceptional community like Pennbrooke, opportunities like this don't last long. This is Central Florida living at its finest! Schedule your showing today—you're going to love calling Pennbrooke Fairways home!
27601 COUNTRY STONE CT, LEESBURG, FL 34748
$379,88882 Days on yellowkey MLS ID: G5107236
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2066 Built: 2007Monthly Fee: $295 Tax: $3,826 (2025)Community: Leesburg Legacy Leesburg Unit 06Single Family
Taxes:$3,826
Remarks: Set on a prominent corner cul-de-sac lot, this expanded Pringle Scarsboro delivers space, privacy, and effortless livability in one of Legacy of Leesburg’s most desirable settings. Thoughtful expansion and a smartly composed floor plan create a home that feels open yet defined, offering multiple living zones that accommodate both refined entertaining and relaxed daily life. The interior is balanced and functional, featuring three well-sized bedrooms and two baths arranged in a split configuration for maximum privacy. A seamless connection between indoor and outdoor living leads to an oversized lanai - an ideal extension of the home for hosting, unwinding, or simply enjoying the Florida climate. Meaningful updates, including a 2020 roof, refreshed interior and exterior finishes, updated flooring, and stainless steel kitchen appliances, underscore the home’s move-in-ready appeal and long-term value. Beyond the front door, Legacy of Leesburg offers a gated, 55+ lifestyle centered on activity, connection, and convenience. Residents enjoy access to tennis, pickleball, bocce, softball, a resort-style pool and spa, and an impressive variety of clubs and social opportunities. HOA services include internet, irrigation, and amenity maintenance, allowing for a truly low-maintenance experience. Ideally located near lakes, natural surroundings, and convenient routes to Orlando and both Florida coasts, this home provides a rare blend of tranquility and accessibility. This is not simply a residence... it’s a well-positioned opportunity to enjoy the best of active adult living in a community designed to elevate everyday life.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Scott Cohara (407-398-9554)
109 N OAKLAND ST, LEESBURG, FL 34748
$242,400199 Days on yellowkey MLS ID: O6348065
1 Days Off yellowkey (back on 3/3/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1512 Built: 1950 Tax: $2,875 (2024)Community: Leesburg Oak CrestSingle Family
Taxes:$2,875
Elementary School: Leesburg Elementary
High School: Leesburg High
Middle School: Oak Park Middle
Remarks: Under contract-accepting backup offers. This charming property at 109 N Oakland Street offers a prime location just steps from historic downtown Leesburg. With its inviting curb appeal and classic Florida character, the property is functional and well maintained. The home sits on a spacious lot and provides easy access to Leesburg’s growing downtown district, where you’ll find boutique shops, restaurants, lakefront parks, and community events year-round. Inside, the property maintains its traditional charm while offering functional living areas filled with natural light. The flexible layout makes it a great option for a buyer looking to customize and add value. Outside, the yard provides ample space for outdoor enjoyment, gardening, or future improvements along with a complimenting workshop in the backyard. Located within minutes of Lake Harris, Venetian Gardens, and major roadways like US-441, this property combines convenience with small-town charm. Whether you’re seeking an affordable home close to downtown or a smart investment in a growing area, 109 N Oakland Street delivers excellent potential.
Listing is courtesy of: RLW REALTY (352-771-2560)
Listing Agent: Logan Wilson (352-771-2560)
25039 PINE HILL, LEESBURG, FL 34748
$149,00049 Days on yellowkey MLS ID: G5108806
REDUCED by $3,900 (2.6%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1440 Built: 1989Monthly Fee: $180 Tax: $1,349 (2025)Community: Plantation At LeesburgManufactured Home
Taxes:$1,349
Remarks: Welcome to this two bedroom two bath home located in the highly sought after 55 plus community of Plantation at Leesburg. A new roof was installed 6 years ago plus luxury vinyl plank flooring throughout most of the home, separate living and family room areas, dining room, kitchen with stainless appliances and tiled counter tops, inside laundry with cabinets, full guest bath, large guest bedroom with 8 ft closet with mirror and doors, master bedroom with dual closets, renovated primary bathroom with dual sinks and dual medicine cabinets, newer shower and light fixtures and upgraded fans throughout the home. Sheetrock was installed throughout the home. There's a Florida room and a nice size wood deck for barbecuing an outside entertaining. They're good size shed combination workshop with golf cart garage door and covered carport. A/C was installed in 2011 works very well and was recently serviced. This golf course community has 2 golf courses, 24 hr. guards at the entrances, three club houses, three swimming pools, large Manor clubhouse which hosts plays and musical events as well as many other activities. Activities include billiards, exercise facilities, bocce ball, tennis, pickleball, baseball field, batting cage, archery, RV and boat storage as well as many others.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Dennis Hjorten (352-255-4526)
5618 ROSEWALL CIR, LEESBURG, FL 34748
$215,00015 Days on yellowkey MLS ID: G5110464
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1306 Built: 1990Monthly Fee: $125 Tax: $2,306 (2025)Community: Highland Lakes Ph 01Single Family
Taxes:$2,306
Remarks: This 2/2 home is a must see in this highly sought after 55+ community of Highland Lakes in beautiful Leesburg. Centrally located close to Leesburg and Clermont. Both cities have a lot for those of you that likes walks around lakes or parks and an abundance of restaurants, markets, breweries and other outdoor activities. The community of Highland Lakes have for their community a beautiful clubhouse, tennis courts and pool, picnic tables overlooking a tranquil lake.
Listing is courtesy of: MICKI BLACKBURN REALTY (352-394-6611)
Listing Agent: Sonia Brown (407-600-5150)
7716 PARK HILL AVE, LEESBURG, FL 34748
$389,90087 Days on yellowkey MLS ID: O6375467
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3022 Built: 2008Monthly Fee: $42 Tax: $5,155 (2025)Community: Park Hill SubSingle Family
Taxes:$5,155
Elementary School: Beverly Shores Elem
Remarks: OPPORTUNITY JUST KNOCKED - 20K LOUDER! Big home, big lot, BIG $20K price drop—this one just became the best value in the subdivision. Welcome to a home that truly lives large—inside and out. Set on an impressive .34-acre corner lot, this sprawling residence is one of the largest homes with one of the biggest lots in the neighborhood, offering room to spread out, entertain, and live comfortably for years to come. From the moment you step into the two-story foyer and living room, the sense of openness is undeniable, with soaring ceilings that set the tone for the generous layout throughout. The first floor offers incredible flexibility, including an extra-spacious bedroom and the potential for an in-law or multi-generational living setup. Upstairs, a bright bonus office or loft overlooks the living area through thoughtfully added windows—maintaining the open feel while creating a perfect space for work, play, or relaxation. Storage is abundant at every turn—this home was designed with space in mind. At the heart of the home is a gourmet kitchen built for entertaining, complete with double ovens, a gas stove, TWO refrigerators, large decorative tile, a cozy dinette area, and a separate formal dining room for hosting memorable gatherings. Upstairs, the primary suite is a true retreat, featuring an en-suite layout that flows into a large bathroom and two separate walk-in closets—plenty of room for all your Florida lifestyle essentials, especially when you’re living near the Chain of Lakes. Now let’s talk about the backyard—because this is where the fun happens. Fully fenced, beautifully spacious, and rarely found at this size, the outdoor area offers endless possibilities: gatherings, play, pets, gardening, or simply enjoying the Florida sunshine. The screened-in lanai is perfect for year-round relaxation or entertaining, while the extended concrete patio expands your outdoor living space even further. This is the kind of backyard that invites memories. Additional highlights include a newer upstairs A/C (2024), epoxy garage floors, and thoughtful upgrades throughout. Located in a quiet neighborhood, you’re just minutes from the beauty of Venetian Gardens, nestled between Lake Harris and Lake Griffin, and close to everything Leesburg has to offer. Enjoy a charming downtown filled with local restaurants and shops, easy access to US-441 and US-27, proximity to Sleepy Hollow Sports Complex, Leesburg Hospital, Lake Square Mall, and nearby colleges including Lake-Sumter State College and Beacon College. Whether your lifestyle calls for space, convenience, entertaining, or simply room to breathe—this home delivers it all. Plenty of room, plenty to do, and a location that truly connects you to the best of Leesburg living.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Carrie Pappas (352-460-1109)
147 ROYAL PALM DR, LEESBURG, FL 34748
$225,00045 Days on yellowkey MLS ID: G5108999
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1308 Built: 2020Monthly Fee: $397 Tax: $1,851 (2025)Community: Hawthorne At Leesburg A CoopManufactured Home
Taxes:$1,851
Remarks: Be prepared to FALL IN LOVE with this 2020 HOME that is LIKE NEW and has been IMPECCABLY MAINTAINED. LUXURY VINYL PLANK FLOORS throughout make the LIVING EASY and an OPEN FLOOR PLAN lends a feeling of SPACIOUSNESS and COMFORT. KITCHEN appliances are STAINLESS STEEL and there are AMPLE CABINETS and COUNTER SPACE. There are CEILING FANS placed strategically in the home, crown molding and a neutral color scheme. The PRIMARY BEDROOM has an EN SUITE with DUAL SINKS, SHOWER with a BUILT-IN BENCH, COMFORT-HEIGHT COUNTER & TOILET, and a WINDOW for NATURAL LIGHT. There are TWO ADDITIONAL BEDROOMS for GUESTS, AN OFFICE, TV ROOM or extra STORAGE ~ whatever you like! UPGRADES TO THIS MODEL INCLUDE: DOUBLE-PANE WINDOWS, SLIDING DOOR FRONT OF HOME, and some BULLNOSE CORNERS. The OVERSIZED CARPORT has space for CARS and a GOLF CART, too, plus a LARGE STORAGE SHED WITH STEEL SHELVING (Fridge and portable shelving in shed do not convey). TRANSFERABLE TERMITE BOND.HAWTHORNE is a PREMIER manufactured home CO-OP COMMUNITY with a plethora of AMENITIES, ACTIVITIES AND CLUBS. Included in the monthly fee are: 24-HOUR GUARDED GATE, CABLE, WATER, SEWER, COMMUNITY FACILITIES USE, ACCESS to HARRIS CHAIN of lakes, A BOAT SLIP, DOCK, MARINA, POOL, TENNIS, RV STORAGE & PICKLEBALL COURTS, EMT SERVICES WITHIN THE COMMUNITY & so MUCH MORE! See attachments for comprehensive list/details.
Listing is courtesy of: FLORIDA PLUS REALTY, LLC (352-901-9100)
Listing Agent: Celie White (352-223-2580)
2316 N GRIFFIN DR, LEESBURG, FL 34748
$545,00021 Days on yellowkey MLS ID: G5110219
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1197 Built: 1952 Tax: $3,439 (2025)Community: Griffin ShoresSingle Family
Taxes:$3,439
Remarks: Direct lake front home on Lake Griffin, part of the Harris chain, this home has been completely reimagined from the inside out, which offers the rare combination of modern finishes, privacy and direct access to one of Central Florida’s most sought-after waterways on the Harris Chain of Lakes. Set on nearly one acre with no HOA, the property slopes gently toward the lake, creating stunning views and a peaceful setting where wildlife, boating activity and spectacular sunrises become part of your everyday backdrop. The interior has been fully renovated to deliver a fresh, modern feel throughout the two-bedroom, two-bath home. From the moment you enter, the open living spaces are designed to showcase the lake, with views stretching from the living room, family room and dining area toward the water. The gorgeous kitchen is truly the centerpiece of the home, featuring an abundance of cabinetry, stainless steel appliances including built-in ovens and a sleek cooktop accented by a touchless vent hood that blends style with convenience. The finishes throughout the home feel thoughtful and elevated, including beautifully selected tile and flooring in both showers. The second bathroom features a clever space-saving shower door design, while the primary bedroom includes a generous walk-in closet area intentionally left open, so you can design the custom closet system that perfectly fits your lifestyle. Practical upgrades add tremendous value and peace of mind, including a brand-new AC system, updated plumbing and electrical and new gutters. An inside laundry area with a stackable washer and dryer is already in place for convenience. Outside, the property shines. Nearly one acre of land with no HOA provides room to breathe and the freedom to enjoy the waterfront lifestyle. The lot gently slopes down to Lake Griffin where you will find a fishing dock ideal for relaxing, casting a line or simply watching the incredible wildlife that makes this lake so special. A private concrete boat ramp allows you to launch your own boat and explore the Harris Chain of Lakes, known for its world-class bass fishing, scenic waterways and the ability to boat between multiple lakes, waterfront restaurants and marinas throughout the chain. Enjoy the outdoors from multiple vantage points, whether you are relaxing on the spacious 22-by-12-foot front patio, entertaining on the rear deck overlooking the backyard and lake or sitting on the dock directly over the water as the sun sets across the lake. A circular driveway leads you to the home and adds both convenience and curb appeal. With a serviced well, well house and a recently pumped septic system, you’ll enjoy the benefit of no water or sewer bills while living on one of Florida’s beloved fishing and boating lakes. This is the perfect opportunity to enjoy a completely updated home with lake views, private lake access, and the freedom of nearly an acre on Lake Griffin, where boating, fishing and nature are right outside your door.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Dawn Giachetti (352-874-2100)
4242 LEAFWAY CIR, LEESBURG, FL 34748
$345,000176 Days on yellowkey MLS ID: O6354460
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2297 Built: 1994Monthly Fee: $165 Tax: $2,526 (2025)Community: Plantation At Leesburg Oak Tree VillageSingle Family
Taxes:$2,526
Remarks: Welcome to The Plantation at Leesburg, a vibrant 55+ active community perfectly located less than an hour from Disney World, Universal Studios, and SeaWorld, and just under two hours from both Florida coasts. Only minutes from Downtown Leesburg, you’ll enjoy convenient access to shops, dining, lakes, and parks; truly the ideal spot for your permanent vacation! This friendly, fully developed community offers over 100 active clubs, two 18-hole golf courses with a full-service restaurant and bar, and three staffed activity centers ensuring there’s always something exciting to do. Your next home features 2 bedrooms, 2 full baths, an office, and a 2-car garage with additional storage cabinets the seller is willing to leave behind. Enjoy the screened-in pool and spacious backyard, perfect for entertaining family and friends. Experience the best of Florida’s active community. The Plantation at Leesburg, where every day feels like a vacation! Buyer must be approved by the HOA. See attachments for the application.
Listing is courtesy of: WYNNMORE REALTY LLC (407-535-0335)
Listing Agent: Cora Johnson (407-535-0335)
3850 PLANTATION BLVD, LEESBURG, FL 34748
$339,00058 Days on yellowkey MLS ID: G5108438
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1822 Built: 1998Monthly Fee: $180 Tax: $4,121 (2025)Community: Plantation At LeesburgSingle Family
Taxes:$4,121
Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bathroom POOL HOME in the highly desirable 55+ community of Plantation at Leesburg. Offering an open and spacious floor plan, this home is designed for both comfortable everyday living and effortless entertaining. Step inside and you’ll immediately appreciate the inviting layout, featuring a formal dining room and a generous family room with sliding glass doors that open to the screened-in pool area. The pool is equipped with solar heating—allowing you to enjoy a swim year-round—and features a pump that was replaced in 2025, providing added peace of mind for the new owner. The primary suite is a true retreat, offering ample space, a walk-in closet, and a private en-suite bath complete with granite countertops, a soaking tub, and a walk-in shower. A private door from the bedroom provides direct access to the pool area, creating the perfect indoor-outdoor flow. The upgraded kitchen is a standout, showcasing quartz countertops, elegant cabinetry, a luxurious backsplash, and a large pantry. The adjacent dinette overlooks the pool, making every meal feel like a getaway. The spacious living room also features sliding glass doors to the pool, providing abundant natural light and additional space for gathering with family and friends. Both guest bedrooms are generously sized and share a well-appointed bathroom with granite countertops and a tub/shower combination. Step outside to the screened pool and back porch area, where you can enjoy alfresco dinners, morning coffee, or evening cocktails while overlooking the sparkling water. With plenty of space for outdoor dining and entertaining, this private retreat is perfect for hosting friends and family or simply relaxing and enjoying Florida’s beautiful weather year-round. The Plantation at Leesburg is an active 55+ community with several amenities including 3 club houses, three swimming pools, two 18-hole golf courses, lighted tennis courts, world class fitness centers, men's & women's wet and dry saunas in the fitness center, pickle ball, bocce ball, shuffleboard, softball/ baseball field, horseshoes, beautiful lakes, great fishing, drama clubs, computer clubs, broadway caliber shows, ballroom dancing, billiards, crafts, full-time activity directors, and Plantation Oaks Restaurant. As an added bonus Plantation is located close to shopping, dining, and all the amenities that The Villages has to offer. This home truly has it all — style, space, and the Florida lifestyle you’ve been dreaming of. Call for your private showing today!
Listing is courtesy of: CENTURY 21 MYERS ROSE REALTY (352-536-0100)
Listing Agent: Dustin Dubie (352-978-5445)
400 CARMAN DR, LEESBURG, FL 34748
$545,000156 Days on yellowkey MLS ID: G5104429
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2356 Built: 2006 Tax: $5,369 (2025)Community: AcreageSingle Family
Taxes:$5,369
Remarks: Welcome to your beautiful 3-bedroom 2 bath home, located in the heart of Leesburg. This 2356 square foot single story style home sits on 1+ gorgeous acre located in a small private gated community of only 5 homes with the friendliest neighbors one could want. New and upgraded features of this property include plenty of room for storage of all of your recreational toys because there is NO HOA to bother you! The home features a large open space with cathedral ceilings, a large bonus Florida room, extra-large added screened lanais off the front and back of the home to enjoy your morning coffee or evening wine while catching a rocket launch, enjoying an easy to access recessed hot tub for safely getting in and out, plus an automated cover to keep in the warmth. Enjoy this bug free space for relaxing anytime of the day. Indoors, the chef-style kitchen features plenty of custom real wood cabinets with newly updated appliances. The laundry features full sized washer and dryer, a hanging space and cabinets to keep the room tidy. The guest bathroom is newly renovated and offers handicap accessibility. New hurricane rated windows with transferable warranty throughout the home, as well as a new energy efficient front door add efficiency for lower utilities. Enjoy your spacious 2-car garage with hurricane rated insulated garage door with Wi-Fi camera capabilities. Room to store all your holiday decorates with 12 feet of overhead storage racks and a climate controlled mechanical roof for storage of delicate items. The property is topped by a metal roof for best hurricane insurability. Rain will empty into the full wrap around 6-inch super gutters with leaf filter gutter guards and downspouts which makes easy maintenance with no worries of leaves from the majestic oak trees that dot the property. The property backs up to 15 acres of private land that will never be developed, beautifully grassed offering a lovely view of sunrise. Desirably located between The Villages, Mount Dora, and Tavares with short drives to restaurants and recreational opportunities. A quick trip to the public boat ramp will have you cruising on Lake Griffin or the chain of lakes from the Lake Harris boat ramp. Come see all that this home has to offer, call for your private showing today!
Listing is courtesy of: DOWN HOME REALTY, LLLP (352-753-0976)
Listing Agent: Rachel Sowder (863-308-3668)
30215 REDTREE DR, LEESBURG, FL 34748
$3,875,000185 Days on yellowkey MLS ID: S5136187
Bed: 6 Bath: 7.5 Gar: 5 Liv Area Sq Ft: 8596 Built: 2002 Tax: $17,078 (2024)Community: Johnsons Mary K & T SSingle Family
Taxes:$17,078
Remarks: 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.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Andy Neal (407-619-3517)
4844 HERON RUN CIR, LEESBURG, FL 34748
$257,00016 Days on yellowkey MLS ID: G5110301
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1289 Built: 1995Monthly Fee: $180 Tax: $1,620 (2025)Community: Plantation At Leesburg Heron RunSingle Family
Taxes:$1,620
Remarks: Welcome to your own private retreat—where comfort meets lifestyle! This beautifully maintained, **furnished home** is move-in ready and perfectly situated in a sought-after **55+ gated community**, offering both convenience and peace of mind. Enjoy added value with a newer water heater, while the wood and vinyl fencing provides charm and privacy. Step out back and unwind with tranquil preserve views—no rear neighbors, just nature and serenity. With its desirable **southwest exposure**, you’ll be treated to stunning sunsets right from your spacious porch, the perfect spot for relaxing or entertaining. Residents of this vibrant community enjoy an exceptional array of amenities, including a clubhouse, fitness center, golf course, sparkling pool, relaxing spa/hot tub, pickleball and tennis courts, shuffleboard, and scenic walking trails—everything you need for an active and social lifestyle. Ideally located just a **short drive from Walt Disney World Resort and other world-class Orlando attractions**, this home offers the perfect balance of peaceful living and nearby excitement. Come see it yourself--you'll fall in love!
Listing is courtesy of: CENTURY 21 MYERS ROSE REALTY (352-717-2000)
Listing Agent: Mildred Feidner (219-669-1201)
1502 HIGH ST, LEESBURG, FL 34748
$399,900175 Days on yellowkey MLS ID: O6355283
Bed: 0 Bath: 0.0 Liv Area Sq Ft: 10883 Built: 1910 Tax: $3,357 (2024)Community: Leesburg Archbell SubMulti-Family 5+
Taxes:$3,357
Remarks: Here is a chance to convert this nine-unit property into a cash-flowing, 10-unit multifamily residence. Located in Leesburg, a market with strong tenant demand and long-term growth, this property holds tremendous potential to address an undersupplied rental market and achieve significant returns. A complete renovation, estimated at $400,000, will be required to achieve its maximum potential. Repairs and upgrades will include reroofing, general system maintenance, cosmetic improvements, updated floor plans, and modern interiors. While this project will require significant work, it presents an opportunity for incredible returns, with an After-Repair Value (ARV) of $1,700,000. This property is a fantastic opportunity to provide value for tenants in a location where demand is strong. Don't miss out on this chance to create affordable and comfortable housing for 10 families. Contact your EquityPro Advisor today.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
26807 BULL RUN, LEESBURG, FL 34748
$294,900351 Days on yellowkey MLS ID: O6304952
3 Days Off yellowkey (back on 3/12/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1962 Built: 2007Monthly Fee: $124 Tax: $2,661 (2023)Community: Leesburg Arlington Ridge Ph 1-ASingle Family
Taxes:$2,661
Remarks: One or more photo(s) has been virtually staged. **MOTIVATED SELLER**Coveted Corner lot on highly sought after street. Pride of home ownership, must see in person! Motivated Seller! New Roof, New HVAC unit, new gas heater, and all new kitchen appliances and sink. PAID CDD. Welcome to the desirable Arlington Ridge, a retirement community that cultivates an active and convenient lifestyle. Arlington Ridge is a gate guarded 55+ community with low monthly HOA fees which include lawn maintenance, high speed internet, WIFI with DISH cable TV: 200+ channels included and a DVR system to record your favorite programs. Amenities in the community include an 18 hole golf course, driving range, putting green, bar and grill restaurant, gym, movie theater, tennis and pickleball courts, and a heated swimming pool and spa! This home is a beautiful, well-maintained corner-lot, two bedroom, two bathroom house and an office with a two-car garage and over 1962 square feet of spacious comfort. As you enter the home, enjoy the luxury of a screen enclosed front patio. Enter the home and be greeted by the dining room which seamlessly flows into the living room and kitchen. Step outside into your glass enclosed outdoor lanai, which offers a serene and peaceful atmosphere. Tile flooring is featured throughout the home and berber carpet is in all bedrooms and office, providing a seamless elegance to the home. The kitchen is equipped with all new stainless steel appliances. Escape into the primary suite with beautiful tray ceilings and enjoy the oversized space featuring a door that leads directly outside onto your covered lanai and an en-suite bathroom. The oversized primary closet is an added bonus with plenty of space and additional storage. An additional bedroom and bathroom are also in the house and an office space allows for the flexibility of an additional bedroom or office space. Step outside and enjoy the fresh, well-manicured landscaping with a yard that extends to the flower bed and magnolia tree, orange tree, and holly tree. A new generator plug-in on the main circuit box allows for added security and reassurance to your home. This house is sure to check off all your boxes! Schedule a showing today and start living a resort-like lifestyle in the Arlington Ridge community!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ivey Asenjo (321-294-7195)
205 PALO VERDE DR, LEESBURG, FL 34748
$169,900177 Days on yellowkey MLS ID: R4910116
REDUCED by $4,600 (2.6%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1024 Built: 1974Monthly Fee: $397 Tax: $860 (2024)Community: Hawthorne At Leesburg A CoopMobile Home
Taxes:$860
Remarks: One or more photo(s) has been virtually staged. TOTAL RENOVATION! Hawthorne at Leesburg. Thoughtfully redesigned with today’s buyer in mind, this elegant residence offers modern convenience, timeless finishes, and a tranquil setting. Beautifully renovated with Chain of Lakes Access. From the moment you arrive, you’ll appreciate the all-new exterior siding, double-pane windows, fresh paint, textured and painted driveway, and updated landscaping that enhance the home’s inviting curb appeal. Inside, the open floor plan allows for natural flow and effortless entertaining, complemented by warm wood tones and carefully chosen design elements that create a welcoming and balanced atmosphere. This spacious two-bedroom, two-bath home also includes a versatile bonus room/den—ideal for a home office, formal dining area, or game room. The living area features a beautiful accent wall, recessed lighting, and an open, comfortable space perfect for relaxing or hosting guests. The custom-designed kitchen is a true showpiece, showcasing 36-inch shaker-style cabinetry, quartz countertops, a workstation island with seating, tile backsplash, recessed lighting, pantry, and all-new stainless-steel appliances. Every detail has been thoughtfully upgraded throughout the home, including luxury vinyl plank flooring, tile, new interior doors, vents, ceiling fans, lighting, and plumbing fixtures. The primary suite offers a spa-like retreat with a beautifully designed tile shower featuring glass doors and a modern sliding barn door for style and space efficiency. Both bathrooms have been completely updated with new vanities, toilets, custom linen storage, and expanded shower and tub designs. Additional updates include a new hot water heater, a new whole-house A/C system with additional venting for the bonus room, a freshly sealed roof, and an updated irrigation system with a French drain for improved drainage. Every inch of this home reflects care, quality, and attention to detail, making this renovation truly complete and move-in ready. Hawthorne at Leesburg is a vibrant 55+ community that offers comfort, convenience, and an active lifestyle. For just $397 a month, residents enjoy a maintenance-free way of living that includes water, sewer, lawn care, emergency services, and access to an array of resort-style amenities. The expansive clubhouse serves as the social heart of the neighborhood, offering over 100 organized activities along with a fitness center, library, fine arts studio, card rooms, billiards, and more—all coordinated by a dedicated activities director. Outdoor enthusiasts will love the private marina with over 120 boat slips providing direct access to the beautiful Harris Chain of Lakes. Safety and peace of mind are at the forefront, with 24/7 on-site firefighter and EMT services, emergency vehicles, and in-home emergency response systems. Residents also enjoy scenic walking trails, lake views, and golf cart–friendly streets that make it easy to reach nearby shopping, dining, and medical facilities. With a sparkling pool, welcoming neighbors, and a warm community atmosphere, Hawthorne at Leesburg isn’t just a place to live—it’s a lifestyle. Schedule your private showing today and experience the perfect blend of comfort, community, and lakefront living.
Listing is courtesy of: BLACK TIE REAL ESTATE PROFESSIONALS, INC. (352-516-8810)
Listing Agent: Dee Brown (352-516-8810)
26812 AUGUSTA SPRINGS CIR, LEESBURG, FL 34748
$475,000187 Days on yellowkey MLS ID: G5103238
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2318 Built: 2018Monthly Fee: $124 Tax: $6,261 (2024)Community: Leesburg Arlington Ridge Ph 1-BSingle Family
Taxes:$6,261
Remarks: Fantastic Gated Golf Community for Active 55+ Living! This home offers a unique and versatile layout, featuring 4 bedrooms, or 3 bedrooms plus an office/study, an uncommon find in a 55+ community! Enjoy the flexibility to create the perfect space for guests, hobbies, or a quiet workspace, all within a premier golf community known for its beautiful surroundings and resort-style amenities. This gorgeous home features a WHOLE HOUSE GENERATOR, thermal pane windows, a beveled glass front door, epoxy garage floor, extra closet space throughout, and beautiful, easy-care landscaping designed for stress-free living. Open and bright kitchen featuring 42-inch cabinets, granite countertops, a convenient breakfast bar, soft-close drawers, pull-out shelves, recessed lighting, and a spacious breakfast nook, perfect for casual dining and morning coffee. Wonderful space throughout this home! There’s plenty of room to accommodate family and friends when they come to visit. The primary suite is extra spacious, featuring a huge walk-in closet and a beautifully designed bath with a large tiled walk-in shower with a built-in seat, an extended vanity with a makeup area, a generous linen closet, and a private water closet for added comfort and privacy. Lastly, enjoy evening cookouts or gatherings on the large covered patio and open screened areas, ideal for hosting friends and family during Florida’s perfect weather months. The backyard offers wonderful privacy, with neighbors set back at a distance, a spacious grassy area, and mature trees that create a peaceful, secluded atmosphere. So much to offer! This wonderful community offers an exceptional lifestyle! Enjoy a Championship golf course surrounded by a winding river and majestic old oaks that frame all 18 holes. Take advantage of the resort-style pool, perfect for cooling off on warm Florida days, or stay active in the spacious fitness center. Additional amenities include tennis courts, a full-service restaurant and bar, numerous clubs and activities, and so much more! With two convenient gated entrances and plenty of sidewalks throughout, this is truly a premier Central Florida location. Just 10–15 minutes to the Florida Turnpike, 45 minutes to Disney World and major theme parks, and 30 minutes to historic downtown Mount Dora. The Villages are only a short drive away, and everyday conveniences like an emergency care hospital, dog park, restaurants, grocery stores, and pharmacies are just minutes from your doorstep. Come discover the perfect blend of relaxation, recreation, and community. Make this gorgeous home and lifestyle yours today!
Listing is courtesy of: WATSON REALTY CORP (352-536-6530)
Listing Agent: Nancy Mccloskey (352-536-6530)
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