Location: Leesburg
Do Not Show Listings
27343 ROANOKE DR, LEESBURG, FL 34748
$327,000236 Days on yellowkey MLS ID: R4910273
REDUCED by $18,000 (5.2%) on 05/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1607 Built: 2017Monthly Fee: $126 Tax: $5,983 (2025)Community: Arlington RidgeSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,983
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: "DARE TO COMPARE!!" How would you like to run your A/C all summer long in this scorching heat and only pay $36 a month?! The sun becomes your friend at this home because it produces solar energy and you don't have to do anything but enjoy the benefits from it! Wouldn't you'd like to have your lawn mowed and trimmed every week, "PLUS" have 24-hour gated security, "PLUS" get HighSpeed Internet/WIFI/HDTV that offers over 250 cable channels with a 'Record On Demand' feature that operates with a push of a button all covered by the HOA dues! These are just some of the many perks you will receive as being a resident of the Arlington Ridge Community. Inside the community boasts The Chesapeake Bay Grille that serves up amazing dishes and The Village Tavern will be there to serve up your favorite beverage to quench your thirst after a vigorous round of golf! There's the St. Charles Movie Theater that is so cozy and quaint or perhaps you prefer O'Hara's to shoot a round of billiards. The Fairfax Hall hosts those special engagements (concerts, dances, parties etc.), The Charleston Social Center has the Crafts room, Library and The Blue Ridge Activity Center is where the hardcore Card Sharks and Game Players entertain. Your pleasure awaits as you bask in the sun along the two heated pools (a lap pool and the other is resort style) or melt away in the jacuzzi. Inside the Activity Center you'll find the Fitness Room, Sauna, indoor Aerobics Room & Spa and right next door you'll find the Cafe and Golf Shop. ** This home nests along the first hole of a championship golf course, it has no front or rear neighbors and is surrounded by mature trees that make for picturesque settings both sun up and sun down!. ** Say you need room to park your small 'Yacht or RV' no worries because there is a special gated area just for the Toys and only costs $25 a month. ** Still want more?! How about having your mailbox at the end of your driveway (now there's a luxury you can't do without). Are you into playing Pickleball, Bocce Ball, Tennis anyone?! There's water aerobic classes or pool volleyball done weekly!! ** This home has no carpeting and has been upgraded with vinyl flooring and the second bathroom had a Safe Step Shower installed in 2025. ** Both the CDD Bond and the Solar panels have been paid so no worries, just rewards. ** An added bonus that most overlook is there is a small pond that is stocked with fish and a great place to take the grandkid(s) to catch some. ** Pear Park is conveniently located nearby and offers amazing nature walking and hiking trails ** If you're looking to stay active with endless possibilities then you can't beat the savings of living in the Ridge! *** All that being said; "what are you waiting for?!" A quick close is possible so get out your phone and schedule your showing today!! ***
Listing is courtesy of: ARROW STAR REALTY LLC (602-524-7222)
Listing Agent: Eric Fiori (602-524-7222)
26709 AUGUSTA SPRINGS CIR, LEESBURG, FL 34748
$375,00068 Days on yellowkey MLS ID: G5111899
2 Days Off yellowkey (back on 7/7/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2235 Built: 2008Monthly Fee: $127 Tax: $5,267 (2025)Community: Arlington Ridge Ph 1-BSingle Family
Taxes:$5,267
Remarks: Virtually Staged. NEW ROOF & NEW AC Replaced 8/2025. Golf Front Living in Arlington Ridge – A Premier 55+ Community! Discover the perfect blend of luxury and relaxation in this spacious 2-bedroom, 2-bathroom home with a large Den/Office, nestled in the highly sought-after Arlington Ridge Golf Club Community in Leesburg, FL. Situated on the 18-hole championship golf course, this stunning home offers breathtaking views and a serene, uncrowded setting in Central Florida’s beautiful Lake County. Enjoy the best of retirement living while being just an hour from Orlando’s world-class attractions, dining, entertainment, and international airport. BOND PAID!!! This home features an expansive primary bedroom with Jack & Jill closets, providing plenty of storage space. The spacious kitchen is designed with elegant granite countertops and durable tile flooring, making it both stylish and functional. With both a family room and a living room, there is ample space for relaxation and entertaining. A large Den/Office offers the perfect setting for work, hobbies, or additional guest space. The home also includes an extended two-car garage, providing extra room for storage or a golf cart. With resort style amenities, a vibrant social scene, and a premier golfing experience right in your backyard, this home is an opportunity you don’t want to miss! Schedule your private showing today and start your next chapter in Arlington Ridge!
Listing is courtesy of: KELLER WILLIAMS CORNERSTONE RE (352-233-2200)
Listing Agent: Paul Lemieux Ii, Pa (786-514-5182)
4358 ANTIETAM CREEK TRL, LEESBURG, FL 34748
$354,9006 Days on yellowkey MLS ID: G5114701
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1776 Built: 2012Monthly Fee: $132 Tax: $170 (2024)Community: Arlington Rdg Ph I-ASpa: YesSingle Family
Taxes:$170
Tax Year: 2024
Remarks: Virtually Staged. Make sure to check out the 3d visual tour!! Looking for a home that offers both an active lifestyle and the peace and quiet that's becoming harder to find? Welcome to this beautifully maintained 3-bedroom, 2-bath concrete block home tucked inside a secure, gated 55+ golf community where every day feels like you're on vacation. Perfectly positioned with convenient access to both Orlando and Tampa, you'll enjoy the best of Central Florida while coming home to a setting that feels worlds away from the hustle and bustle. One of this home's most desirable features is what lies beyond your back door—protected state-owned land. Instead of looking directly into a neighbor's lanai every morning, you'll sip your coffee surrounded by privacy, natural beauty, and tranquil views that are expected to remain unchanged. It's the kind of peaceful backdrop that homeowners dream about but rarely find. Inside, the thoughtfully designed open floor plan is ideal for entertaining and everyday living. The kitchen is the heart of the home, showcasing elegant stone countertops, upgraded cabinetry, an oversized island with seating, dual built-in ovens including a convection oven, a gas cooktop, built-in microwave, decorative tile backsplash, abundant prep space, and plenty of conveniently placed outlets for today's appliances. The spacious 18' x 24' great room flows effortlessly through sliding doors to the impressive 20' x 40' screened lanai, featuring both covered and open areas, ceiling fans, and your own private spa—the perfect place to unwind after a day of golf, recreation, or exploring Central Florida. The primary suite offers soaring 9-foot ceilings, two generous walk-in closets, and a well-appointed ensuite bath complete with dual vanities featuring stone countertops, a private water closet, and a large walk-in shower. A dedicated laundry and mudroom provides easy access to the oversized two-car garage, which includes overhead storage racks and a 220-volt outlet ready for your electric vehicle. Whether you're searching for an active retirement, a lock-and-leave lifestyle, or simply a beautiful home with unmatched privacy, this exceptional property is truly move-in ready and offers the perfect balance of comfort, convenience, and carefree Florida living.
Listing is courtesy of: BLACK TIE REALTY, INC. (352-751-7888)
Listing Agent: Mark Dyer (352-516-8808)
3851 MANOR OAKS CT, LEESBURG, FL 34748
$350,0005 Days on yellowkey MLS ID: G5114468
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2555 Built: 1998Monthly Fee: $180 Tax: $4,182 (2025)Community: Plantation At Leesburg River Crest Unit 02Single Family
Taxes:$4,182
Remarks: Expanded Rose Model! This spacious home features 2 owner's suites with large walk-in closets and an abundance of living space, including a family room, formal living room, dining room, den, and great room. The kitchen offers a large breakfast bar with seating and plenty of workspace. Major updates include Lifetime Anderson windows, a new roof, and a new A/C. Enjoy the privacy of the screened lanai overlooking green space, plus a large patio perfect for grilling and entertaining. The oversized 2-car garage includes a separate golf cart garage, and the extended driveway provides ample parking. Beautiful mature landscaping adds to the home's curb appeal. Located in the highly desirable Plantation at Leesburg, this premier 55+ gated community offers outstanding amenities, including 2 championship golf courses, 3 clubhouses, 3 swimming pools, 2 fitness centers, pickleball, tennis, walking trails, softball, basketball, billiards, a woodworking shop, horseshoes, a pro shop, and countless clubs and activities. Residents also enjoy the community restaurant and lounge featuring live entertainment, drink specials, and weekend bands. Low HOA fees, resort-style living, and a quick closing available make this home an exceptional value. Schedule your private showing today!
Listing is courtesy of: CENTURY 21 MYERS ROSE REALTY (352-717-2000)
Listing Agent: Mary Jane Grimes (410-353-0795)
27103 CAMERONS RUN, LEESBURG, FL 34748
$400,0004 Days on yellowkey MLS ID: O6424199
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2236 Built: 2016Monthly Fee: $128 Tax: $6,646 (2025)Community: Leesburg Arlington Ridge Ph 02Spa: NoSingle Family
Taxes:$6,646
Remarks: Virtually Staged. BOND PAID + GOLF COURSE VIEWS! Welcome to 27103 Camerons Run, a beautifully maintained 3-bedroom, 2-bath home offering over 2,000 square feet of living space, an extended 2-car garage, and a fantastic location overlooking the #2 fairway of the Arlington Ridge Golf Course! Located in the sought-after gated 55+ community of Arlington Ridge, this home offers exceptional value paired with a resort-style lifestyle. Step inside to a bright and spacious open floor plan with a desirable split-bedroom layout that provides privacy for both owners and guests. The living, dining, and kitchen areas flow seamlessly together, creating the perfect setting for entertaining family and friends or simply enjoying everyday life. The spacious kitchen is the heart of the home, featuring upgraded granite countertops, quality cabinetry, stainless steel appliances, a natural gas range, a large center island, and two pantries offering exceptional storage. Relax and unwind on the large enclosed, screened lanai overlooking the golf course. Enjoy your morning coffee, entertain guests, or take in the peaceful views of the #2 fairway at the end of the day. The extended 2-car garage provides additional space for vehicles, storage, hobbies, and more. Residents of Arlington Ridge enjoy an exceptional active-adult lifestyle with an 18-hole championship golf course, putting and chipping greens, Pro Shop, on-site restaurant and tavern, spa and fitness center, tennis and pickleball courts, screening room, and a full calendar of clubs, activities, and social events. Even better, the low HOA fee includes lawn mowing, edging and blowing, high-speed internet, cable TV with more than 200 channels, community security, sidewalks, and street lighting—giving you more time to enjoy the Florida lifestyle. Ideally located near shopping, dining, medical facilities, and hospitals, Arlington Ridge is also surrounded by Lake County's many lakes, offering endless opportunities for boating, fishing, and outdoor recreation. With the BOND PAID, golf course views, spacious split-bedroom floor plan, extended garage, and resort-style amenities, this home delivers the lifestyle you've been looking for. Schedule your private showing today and experience everything Arlington Ridge has to offer!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Christine Landrau (407-949-1421)
1117 BEN HOPE DR, LEESBURG, FL 34788
$325,0004 Days on yellowkey MLS ID: G5114745
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2280 Built: 1991Monthly Fee: $220 Tax: $3,963 (2025)Community: Scottish Highlands Condo Ph KSingle Family
Taxes:$3,963
Remarks: Welcome to the largest home in the desirable 55+ community Scottish Highlands! Stepping through the front door you enter into the spacious living room with stylish wood-look luxury vinyl that continues through the home. The dining area leads to a bonus room that is perfect for an office, hobby room, or even a home gym! If you love to cook, this kitchen is for you! Center island, tons of cabinet space, beautiful marble counters, electric cook top AND gas range! You will have plenty of space in the primary bedroom that features private bath with duel sinks, stand up shower, and garden tub. The secondary bathroom is at the other end of the home that has access to the full hall bathroom. Scottish Highlands is an active community with a lot to offer. Tennis courts, fitness center, outdoor pool, Olympic size indoor pool which features a hot tub. Gatherings and classes are always taking place at the clubhouse and residents enjoy the benefits of community perks such as cable, internet, and water included in your association membership. Call for your private tour today!
Listing is courtesy of: EXIT REALTY TRI-COUNTY (352-385-3948)
Listing Agent: Jaret Whitney (352-385-3948)
27305 RACQUET CIR, LEESBURG, FL 34748
$328,0004 Days on yellowkey MLS ID: O6423691
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2886 Built: 1997Monthly Fee: $135 Tax: $2,364 (2025)Community: Highland Lakes SubSingle Family
Taxes:$2,364
Remarks: Virtually Staged. SPACIOUS CUSTOM HOME WITH POND VIEWS! Discover nearly 2,900 square feet of comfortable Florida living in this beautifully maintained 3-bedroom, 2-bath custom home with a 2-car garage, tucked away on a quiet street in the sought-after, gated 55+ community of Highland Lakes. The spacious split-bedroom floor plan features soaring vaulted ceilings, abundant natural light, generous living and dining areas, and plenty of room for guests, hobbies, and working from home. One guest bedroom features a built-in desk and organized workspace, while an additional tiled office area provides even more flexibility. Relax or entertain in the expansive enclosed Florida room, then step outside to the screened lanai overlooking a peaceful pond and lush greenbelt—an ideal setting for morning coffee, wildlife watching, and beautiful Florida sunsets. Residents of this gated community enjoy an exceptional active lifestyle with indoor heated and outdoor pools, fitness facilities, tennis and pickleball courts, shuffleboard, bocce ball, a golf driving range and practice facilities, nature trails, seven lakes with catch-and-release fishing, clubhouse activities, billiards, crafts, clubs, social events, and secure RV and boat storage included with the HOA. Enjoy the space you want, the peaceful setting you'll love, and the security and active lifestyle of one of the Leesburg area's most amenity-rich gated 55+ communities. Schedule your private showing today!
1000 LOVES POINT DR, LEESBURG, FL 34748
$873,8004 Days on yellowkey MLS ID: G5114858
Bed: 2 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2945 Built: 1957 Tax: $3,449 (2025)Community: Leesburg, Loves PointSingle Family
Taxes:$3,449
Remarks: Experience the waterfront lifestyle you've been dreaming of in this beautifully rebuilt and renovated lakefront retreat, where timeless craftsmanship, energy efficiency, and breathtaking natural beauty come together. Nestled beneath majestic moss-draped cypress trees, this exceptional 2 Bdrm/3 Bath home with bonus room & office offers panoramic views across Lake Harris, spectacular sunsets, and front-row seats to rocket launches viewed across the water. Designed to maximize both comfort and scenery, the open floor plan is filled with natural light and features soaring vaulted tongue-in-groove ceilings, a spacious great room, and expansive windows framing the ever-changing waterfront. A striking coquina rock gas fireplace creates a warm focal point while seamlessly connecting the living, dining, and entertaining areas. The gourmet kitchen features custom 42- inch solid wood cabinetry, a cabinet-paneled refrigerator, abundant counter space, a gas cooktop, and a halogen oven. Wake each morning to tranquil lake views from the spacious primary suite with dual vanities, a walk-in shower & private water closet and a generous California-style walk-in closet. Step outside the living room to an expansive patio already plumbed for a future summer kitchen, perfect for entertaining or simply relaxing while enjoying cooling lake breezes and unforgettable sunsets. Just steps away, the impressive 14' x 34' boathouse with a boat lift and reinforced pilings places you only seconds from open water on Lake Harris and the renowned Harris Chain of Lakes. Spend your days boating, fishing, waterfront dining, or exploring miles of interconnected lakes. Adding exceptional long-term value, the home includes a fully warranted rooftop solar system installed in 2023, with the seller paying the balance in full at closing, allowing you to enjoy outstanding energy efficiency and dramatically reduced electric costs. This meticulously maintained home also offers underground city utilities including natural gas service, a new roof in 2021, two zoned HVAC systems, and two water heaters for added comfort and peace of mind. Conveniently located just minutes from historic downtown Leesburg, Venetian Gardens, UF Health Leesburg Hospital, The Villages, shopping, dining, and entertainment, this remarkable property delivers one of Central Florida's finest waterfront lifestyles. Don't miss this rare opportunity to own an energy-efficient lakefront retreat where every day feels like a vacation. Schedule your private showing today and experience everything this remarkable property has to offer.
Listing is courtesy of: CENTURY 21 ALTON CLARK (352-728-2121)
Listing Agent: Ted Trawick (352-322-9329)
1671 ANN ROSE WAY, LEESBURG, FL 34748
$355,9006 Days on yellowkey MLS ID: O6423135
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1970 Built: 2026Monthly Fee: $18 Tax: $253 (2025)Community: Arbor ParkSpa: NoSingle Family
Taxes:$253
Elementary School: Fruitland Park Elem
High School: Leesburg High
Middle School: Carver Middle
Remarks: Under Construction. Under Construction – Welcome Home to Comfortable Florida Living! Discover the perfect combination of modern design, quality craftsmanship, and everyday comfort in this beautiful 3-bedroom, 2-bath home located in one of Leesburg's newest and most desirable communities. Inside, you'll find a thoughtfully designed single-story floor plan featuring an open-concept layout filled with natural light. The spacious living, dining, and kitchen areas flow seamlessly together, creating the perfect setting for entertaining guests or enjoying quiet evenings at home. The well-appointed kitchen offers granite countertops, ample cabinetry, and generous workspace, making meal preparation both convenient and enjoyable. The private owner's suite provides a relaxing retreat, while two additional bedrooms provide flexibility for family, guests, or a home office. Designed with comfort and functionality in mind, this home is ideal for first-time homebuyers, downsizers, or anyone looking to enjoy low-maintenance Florida living. Conveniently located in Leesburg, you'll be just minutes from shopping, dining, major roadways, the Chain of Lakes, the Leesburg Public Library, historic Downtown Leesburg, and approximately 15 minutes from Florida's Turnpike, providing easy access throughout Central Florida. Residents of this growing community will enjoy outstanding planned amenities, including a resort-style swimming pool with cabanas, pickleball courts, scenic nature trails, a tot playground, dog park, community pavilions, and open green spaces designed for recreation and relaxation. Please note: This home is currently under construction. The photos shown are from a previously completed home featuring the same floor plan with a different elevation and are for illustrative purposes only. Colors, finishes, fixtures, landscaping, and design selections may vary from the home currently under construction. Don't miss the opportunity to own a beautifully designed new home in one of Leesburg's fastest-growing communities. Contact us today for construction updates and to schedule your private tour of Arbor Park!
Listing is courtesy of: ADAMS HOMES REALTY, INC (850-469-0977)
Listing Agent: Bri Mcswain (407-454-0960)
1684 ANN ROSE WAY, LEESBURG, FL 34748
$355,9006 Days on yellowkey MLS ID: O6423122
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1755 Built: 2026Monthly Fee: $18 Tax: $253 (2026)Community: Arbor ParkSingle Family
Tax Year: 2026
Remarks: Under Construction – Only $1,000 Down at Contract! Discover the perfect combination of modern design, everyday comfort, and exceptional value in this beautifully crafted 4-bedroom, 2-bath home. Designed with today's lifestyle in mind, this thoughtfully planned layout features spacious open living areas, abundant natural light, and stylish finishes throughout. The heart of the home is the stunning kitchen, complete with granite countertops, ample cabinetry, a large center island, and modern appliances—perfect for preparing meals, gathering with family, or entertaining friends. Just off the kitchen, a separate dining room provides the ideal setting for holiday meals, dinner parties, or everyday dining. The private owner's suite offers a relaxing retreat with generous space, while three additional bedrooms provide endless flexibility for guests, kids, a home office, or hobby room. Every inch of this home has been designed to maximize comfort, storage, and functionality. Step outside and imagine creating your own backyard oasis with plenty of room for outdoor entertaining, pets, gardening, or simply enjoying Florida's beautiful weather. Residents of this growing community will enjoy outstanding planned amenities, including a resort-style swimming pool with cabanas, pickleball courts, scenic nature trails, a tot playground, dog park, community pavilions, and open green spaces designed for recreation and relaxation. With only $1,000 due at contract, owning a brand-new home has never been more attainable. Please note: This home is currently under construction. The photos shown are from a previously completed home featuring the same floor plan and are for illustrative purposes only. Colors, finishes, fixtures, elevations, landscaping, and design selections may vary from the home currently under construction. Visit our model home today to experience the quality craftsmanship, thoughtfully designed floor plans, and lifestyle this exceptional community. Schedule your private tour today and see why so many buyers are choosing to call Arbor Park home!
8604 OAKSTONE CIR, LEESBURG, FL 34748
$348,99099 Days on yellowkey MLS ID: O6396647
0 Days Off yellowkey (back on 6/19/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1876 Built: 2026Monthly Fee: $100 Tax: $239 (2025)Community: Oakstone FarmsSingle Family
Taxes:$239
Elementary School: Treadway Elem
Middle School: Oak Park Middle
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Set within Oakstone Farms, a thoughtfully planned new community just 5.5 miles from downtown Leesburg, this home places you in the heart of the celebrated Harris Chain of Lakes. More than 50,000 acres of sparkling waterways span eight interconnected lakes, creating a paradise for boating, fishing, and days spent exploring Central Florida’s natural beauty. Nearby favorites such as Mount Dora and Tavares bring charming waterfront dining, boutique shopping, and year-round festivals, while the surrounding area keeps everyday conveniences within easy reach. Within Oakstone Farms itself, residents enjoy welcoming neighborhood spaces including dedicated greenspace, a dog park, and a tot lot designed to bring neighbors together. The Maple showcases a modern layout designed for comfortable everyday living. Entry and driveway pavers add curb appeal, while a 6'8" full-lite front door opens into a bright foyer beneath 8'8" ceilings. Two secondary bedrooms are positioned toward the front of the home, one featuring a walk-in closet, with a full bath conveniently centered between them. At the heart of the home, the open living, dining, and kitchen areas create a seamless gathering space. The kitchen is finished with granite countertops, a tile backsplash, and gas appliances, blending style with everyday functionality. Nearby, a versatile flex room provides additional space that can easily serve as a home office, hobby room, or quiet retreat. Privately situated toward the rear, the owner’s suite delivers a peaceful escape with a spacious walk-in closet and a well-appointed bath featuring dual sinks, granite countertops, and an oversized ceramic tile walk-in shower. An additional secondary bedroom at the back of the home adds even more flexibility to the floor plan. A walk-through laundry room with gas hookup connects to the two-car garage, and practical features such as a gas tankless water heater, gutters, dual-pane windows, and architectural shingles contribute to efficiency and long-term value. Ceramic tile flooring runs through the main living areas, with soft carpet in the bedrooms, and blinds are included throughout. Step outside to a 10x22 aluminum screened porch, an inviting setting for relaxing evenings or weekend gatherings. Smart home technology including a Ring video doorbell, smart thermostat, and keyless entry door lock adds modern convenience, all backed by a full builder warranty. Life at Oakstone Farms places recreation, small-town charm, and scenic lakefront destinations within reach, while the community’s greenspaces, dog park, and tot lot help shape a welcoming neighborhood atmosphere from the very beginning. Secure your homesite and begin shaping this Maple residence from the ground up in one of Lake County’s newest communities.
Listing is courtesy of: NEW HOME STAR FLORIDA LLC (407-803-4083)
Listing Agent: Charles Pennant (407-305-4317)
8592 OAKSTONE CIR, LEESBURG, FL 34748
$375,99099 Days on yellowkey MLS ID: O6396600
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1989 Built: 2026Monthly Fee: $100 Tax: $239 (2025)Community: Oakstone FarmsSingle Family
Remarks: Pre-Construction. To be built. Set within Oakstone Farms, this beautifully designed home places you in the heart of one of Central Florida’s most treasured lake regions, the renowned Harris Chain of Lakes. Spanning more than 50,000 acres across eight interconnected lakes and scenic canals, the area is beloved for boating, fishing, and days spent enjoying Florida’s natural beauty. Within the neighborhood, thoughtfully planned greenspace, a dog park, and a tot lot contribute to a welcoming setting where neighbors connect and outdoor living is part of everyday life. Inside, the four-bedroom Drexel floor plan blends comfort and thoughtful design. A striking 8-foot glass full-lite front door opens to a welcoming foyer accented by 9-foot 4-inch ceilings and deluxe interior trim that continue throughout the home. Two secondary bedrooms are positioned at the front and share a full bath, creating a functional layout with both privacy and convenience. The living areas unfold into a bright, open space where the kitchen serves as the centerpiece. Quartz countertops, soft-close cabinetry, a gas range, a large center island, and a generous pantry create a kitchen designed for both everyday living and gatherings. The space flows seamlessly into the kitchen nook and expansive great room, while sliding doors lead to the covered lanai for relaxed indoor and outdoor living. Privately positioned at the rear of the home, the owner’s suite provides a quiet retreat with a spacious walk-in closet and a well-appointed deluxe primary bath with an oversized shower and dual vanity. An additional bedroom features a built-in closet, and the laundry room is conveniently located just behind the kitchen with direct access to the two-car garage. Additional features include dual-pane windows, gas tankless water heater, architectural shingles, entry & driveway brick pavers, full landscaping, and irrigation in the front and sides supplied by reclaimed water. Modern convenience continues with a built-in Smart Home Package that includes a Ring Video Doorbell, smart thermostat, keyless entry smart door lock, and Deako smart switches. A full builder warranty adds lasting peace of mind. Beyond the home itself, life in Oakstone Farms connects you with some of Central Florida’s most charming destinations. The lakeside communities of Mount Dora and Tavares are known for waterfront dining, boutique shopping, and year-round festivals, while Leesburg sits just 5.5 miles away for everyday shopping, dining, and entertainment. Here, the beauty of Florida’s lake country and the comforts of a thoughtfully designed home come together in a setting that truly feels special.
3909 RIVER CREST CIR, LEESBURG, FL 34748
$284,000493 Days on yellowkey MLS ID: G5093974
REDUCED by $5,000 (1.7%) on 07/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1690 Built: 1997Monthly Fee: $162 Tax: $3,569 (2024)Community: Plantation At Leesburg River Crest Unit 01Spa: YesSingle Family
Taxes:$3,569
Remarks: Highly motivated seller, bring all offers. Beautifully maintained home with Stunning Golf Course Views in The Plantation at Leesburg Welcome to this beautifully maintained three-bedroom, two-bathroom home in the highly sought-after Plantation at Leesburg community. Boasting a breathtaking 180-degree view of the 17th and 18th fairways, this is truly a golfer’s dream location! Enjoy Florida living at its finest with a screened-in Florida room and a spacious paver patio, perfect for relaxing and entertaining while soaking in the serene golf course views. This turn-key home comes fully furnished and includes an 2008 EZGO golf cart for easy access to the course and community amenities. Recent upgrades include a new Roof (2018), Samsung HE washer and dryer (2024) and a new water heater (2021), New HVAC (2011), ensuring comfort and efficiency. Whether you’re a snowbird, an avid golfer, or seeking a peaceful, well-maintained 55+ community, this home is an excellent choice. Located just minutes from The Villages, you’ll have easy access to shopping, dining, and entertainment while enjoying the tranquility of this wonderful retirement community. Don’t miss this rare opportunity—schedule your showing today!
Listing is courtesy of: FLAMINGO REAL ESTATE & MNGMT (352-689-1000)
Listing Agent: Kody Ondriezek (352-461-4667)
33651 OVERTON DR, LEESBURG, FL 34788
$475,00076 Days on yellowkey MLS ID: O6402186
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $10,000 (2.1%) on 05/19/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2678 Built: 1974 Tax: $5,432 (2025)Community: Country Club View SubSpa: NoSingle Family
Taxes:$5,432
Remarks: Under contract-accepting backup offers. Welcome to Leesburg, the “City of Lakes,” where space, privacy, and convenience come together on this nearly one-acre homesite just minutes from Lake Silver and the Harris Chain of Lakes. This solid concrete block home offers a flexible split floor plan with two primary suites featuring private ensuites, plus an additional bedroom and bathroom, ideal for multi-generational living or guests. The updated kitchen with newer cabinetry and granite countertops opens seamlessly to a spacious living and entertaining area with a wood-burning fireplace and built-in bar, all connecting to a bright enclosed sunroom and pool area for easy indoor-outdoor living. A separate oversized living room with large windows brings in abundant natural light and adds even more functional space. Outside, enjoy mature oak trees, a large private pool with a recently replaced pump (2025), and plenty of yard space to relax or entertain. The property also features an oversized driveway with ample parking, a two-car garage, and no HOA, giving you flexibility and room for additional vehicles. Major upgrades include a metal roof installed in 2019 with a lifetime warranty, a newer drainfield, and a fully connected natural gas whole-home generator for reliable backup power. This is a well-maintained property offering land, upgrades, and a peaceful setting just minutes from everything Leesburg has to offer.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Evan Caulfield (407-432-9767)
1010 NEWMAN DR, LEESBURG, FL 34748
$239,00041 Days on yellowkey MLS ID: O6413295
REDUCED by $6,000 (2.4%) on 07/10/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1182 Built: 1955 Tax: $1,914 (2025)Community: Leesburg Bel MarSingle Family
Taxes:$1,914
Remarks: NO HOA Fully renovated 4 bedroom, 2 bath home offering 1182 sqft of updated living space on an oversized 0.22-acre lot with no HOA. This beautifully redesigned property features a spacious suite with an oversized walk in closet, including a flexible split-bedroom layout with one bedroom offering its own private entrance and adjacent full bathroom. Recents upgrades include a brand-new roof, A/C system, luxury vinyl flooring throughout, fres interior and exterior paint, renovated bathrooms, and a completely updated kitchen with new cabinetry, countertops, and appliances. Covered parking and detached storage buildings providing extra storage and functionality. Move in ready and conveniently located in an established area of Leesburg. All information provided is believed to be accurate but should be independently verified by buyers and buyer’s agents.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Ana Martin (407-989-3597)
204 ROUND MAN ST, LEESBURG, FL 34748
$300,0006 Days on yellowkey MLS ID: O6423369
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2057 Built: 2006Monthly Fee: $38 Tax: $4,718 (2025)Community: Leesburg Sleepy Hollow First AddSpa: NoSingle Family
Taxes:$4,718
Remarks: Virtually Staged. Experience 204 Round Man St, recently updated with fresh interior paint that brightens every space. The kitchen contains all stainless steel appliances, ready for daily use. The primary bathroom provides functional design with double sinks and a separate tub and shower, promoting ease. Outside, a covered patio extends the living area for enjoyable moments. Move right into this thoughtfully updated, comfortable residence.. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
5909 WINDSONG OAK DR, LEESBURG, FL 34748
$300,00045 Days on yellowkey MLS ID: O6411614
REDUCED by $5,000 (1.6%) on 06/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1875 Built: 2013Monthly Fee: $86 Tax: $3,578 (2025)Community: Windsong At LeesburgSpa: NoSingle Family
Taxes:$3,578
Elementary School: Leesburg Elementary
Remarks: Virtually Staged. Lowest Price per foot in Windsong at Leesburg! Seller will put on a NEW Roof prior to closing with accepted contract! Welcome to 5909 Windsong Oak Drive NEAR the quiet culdesac in the very back of this quiet community, in the desirable Windsong at Leesburg community—where modern comfort, convenience, and Florida living come together beautifully. This move-in-ready home offers 1,875 square feet of thoughtfully designed living space featuring attractive stone accents, durable block-and-stucco construction, energy-efficient double-pane windows, and a spacious two-car garage. Step through the impressive foyer and discover an open-concept floor plan highlighted by large ceramic tile flooring, abundant natural light, and spacious gathering areas perfect for entertaining or everyday living. The heart of the home is the oversized kitchen featuring rich espresso cabinetry, granite countertops, stainless steel appliances, abundant prep space, and a large dining area ideal for family dinners and holiday celebrations. The expansive living room flows seamlessly to the large covered lanai through oversized sliding glass doors, creating the perfect indoor-outdoor lifestyle. Whether you're enjoying your morning coffee, relaxing after work, or hosting friends and family, this inviting space is designed to be enjoyed year-round. The oversized primary suite serves as a private retreat with plenty of room for a sitting area, a huge walk-in closet, and a luxurious ensuite bath featuring dual vanities, solid-surface countertops, a soaking tub, and a separate walk-in shower. Secondary bedrooms are with comfort and privacy, while the oversized laundry room provides additional storage and functionality. Beyond the home itself, Windsong at Leesburg offers exceptional community amenities with low HOA fees. Residents enjoy a beautiful community pool, covered seating and gathering areas, and a playground, creating the perfect setting for relaxation, recreation, and neighborhood gatherings. Location is another standout feature. Conveniently situated near Publix, shopping, restaurants, medical facilities, and daily conveniences, everything you need is just minutes away. Outdoor enthusiasts will appreciate the close proximity to public boat ramps and the area's beautiful lakes, providing endless opportunities for boating, fishing, kayaking, and waterfront fun. Commuters will love the easy drive to Clermont, Minneola, and surrounding Central Florida destinations, while wine enthusiasts can enjoy nearby weekends at Lakeridge Winery, one of Florida's premier wineries known for its scenic vineyards, festivals, and live entertainment. If you've been searching for a move-in-ready home in Leesburg with granite countertops, stainless steel appliances, an oversized primary suite, covered lanai, low HOA fees, community pool, playground, and convenient access to shopping, boating, and Clermont, then 5909 Windsong Oak Drive is the opportunity you've been waiting for. Schedule your private showing today and discover why this exceptional home stands out from the competition.
Listing is courtesy of: NEXTHOME LOTT PREMIER REALTY (407-222-0495)
Listing Agent: Corey Lott (407-222-0495)
1142 MEADOWBEND DR, LEESBURG, FL 34748
$275,00037 Days on yellowkey MLS ID: G5113417
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 2003Monthly Fee: $265 Tax: $4,045 (2025)Community: Pennbrooke FairwaysSpa: NoSingle Family
Taxes:$4,045
Remarks: Great home in Pennbrooke Fairways; a 55+ active lifestyle community. The home features a spacious dining and living room combination plus a bonus room that will make a perfect den, office, craft room, etc. The kitchen has plenty of cabinet and counter space. The primary bedroom features a walk in closet and the primary bathroom has double vanities. The enclosed lanai is the perfect spot to enjoy your morning coffee as you look out to your private back yard. The home is situated on a quiet dead-end street, offering minimal traffic and added privacy. Pennbrooke Fairways is a gated community located just five minutes south of The Villages and less than an hour from Orlando International Airport. Residents enjoy access to the Pennbrooke Fairways golf course featuring two executive nines and one regulation nine, with golf packages available. Additional amenities include 24-hour security, MULTIPLE POOLS, recreation and fitness centers, a clubhouse with restaurant, hair salon, library, RV and boat storage with dump and wash stations, and a full calendar of planned activities. The HOA includes cable, internet, lawn, and trash service. Conveniently located near Brownwood Town Square, Downtown Leesburg, and all the shopping, dining, and entertainment nearby (The Villages).
Listing is courtesy of: SELLSTATE SUPERIOR REALTY (352-877-3901)
Listing Agent: Susan Beville, Pa (352-804-0297)
4936 SAWGRASS LAKE CIR, LEESBURG, FL 34748
$263,50083 Days on yellowkey MLS ID: G5111335
0 Days Off yellowkey (back on 7/10/2026)
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1784 Built: 2000Monthly Fee: $180 Tax: $2,309 (2025)Community: Plantation At Leesburg Sawgrass VillageSpa: NoSingle Family
Taxes:$2,309
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully maintained one-owner home in the highly sought-after gated community of Plantation at Leesburg! Offering 3 bedrooms, 2 bathrooms, and 1,784 square feet of living space, this home has been exceptionally cared for and is move-in ready. A major highlight is the rare and highly desirable 2-car garage PLUS golf cart garage, perfect for enjoying the active lifestyle this community offers. The home also features a 2017 roof, providing added peace of mind. Inside, you’ll find a spacious and functional layout with generously sized rooms. The large primary suite includes a walk-in closet and an oversized en-suite bathroom with dual vanities, a soaking tub, and a separate shower. Having three bedrooms offers flexibility and can easily serve as a home office or den. Step outside to the screened lanai—an ideal space to enjoy your morning coffee or relax during Florida’s beautiful evenings. Location is key, and this home is just a short distance to one of the community’s resort-style amenity centers, featuring a pool, hot tubs, clubhouse, and pickleball courts. Plantation at Leesburg offers an incredible lifestyle with two golf courses, multiple pools and fitness centers, clubhouses, and a wide variety of activities. With its prime location, excellent condition, and standout features, this home is a fantastic opportunity in one of Central Florida’s premier active communities. Don’t miss your chance to make it yours!
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Richard Gullian Llc (352-223-7713)
1639 ANN ROSE WAY, LEESBURG, FL 34748
$344,900108 Days on yellowkey MLS ID: O6394554
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1820 Built: 2026 Tax: $253 (2025)Community: Arbor ParkSingle Family
Remarks: SPECIAL BUILDER INCENTIVES AVAILABLE! Receive $10,000 Flex Cash to apply toward closing costs, prepaids, or an interest rate buy-down, plus only $1,000 down at contract and closing cost covered with preferred lender! This brand-new 4-bedroom, 2-bathroom home offering 1,820 sq ft of living space is designed with comfort, functionality, and modern living in mind. The home features 10-foot ceilings throughout, creating a bright and open atmosphere. The thoughtfully designed floor plan provides a seamless flow between the living, dining, and kitchen areas, making it ideal for everyday living and entertaining. The spacious primary suite offers a private retreat with vaulted ceilings and conservation views, providing added privacy and a peaceful natural backdrop. At the center of the home is a modern kitchen with a center island, perfect for meal preparation and casual dining, along with a breakfast nook for everyday gatherings. A separate formal dining room offers additional flexibility and may also be used as a home office or multipurpose space. The three additional bedrooms are generously sized, offering comfort and privacy for family members or guests. Outdoor living can be enjoyed from the covered lanai, ideal for relaxing or entertaining while enjoying Florida’s year-round weather. Additional highlights include a 1-year builder warranty, 2-year plumbing and electrical warranty, and a 10-year structural warranty, providing added peace of mind.
Listing Agent: Justin Derazza (352-455-9989)
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