Location: Leesburg , 34748
Do Not Show Listings
25045 PINE HL, LEESBURG, FL 34748
$159,90062 Days on yellowkey MLS ID: G5108405
REDUCED by $9,100 (5.4%) on 04/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1188 Built: 1987Monthly Fee: $195 Tax: $1,871 (2025)Community: Plantation At LeesburgManufactured Home
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,871
Elementary School: Leesburg Elementary
High School: Leesburg High
Tax Year: 2025
Middle School: Oak Park Middle
Remarks: Attention investors. Excellent rental income from this home or your own private oasis. Discover comfortable, low-maintenance living in this partially furnished 2-bed, 2-bath home located in the desirable **55+ Pine Hill Village** within **Plantation at Leesburg**. Offering **1,188 sq ft** of well-designed space, this move-in-ready home that is partially furnished . Recent upgrades include new doors and windows (2022), a new roof (2019), and HVAC (2014)—providing peace of mind for years to come. The bright, fully glassed-in front sunroom is perfect for morning coffee or relaxing afternoons. A covered carport with an attached storage/workshop area adds extra convenience and functionality. A golf cart is included**. Plantation at Leesburg offers an exceptional lifestyle with two championship golf courses three pools, a clubhouse, pickleball and tennis courts, billiards, fitness classes, arts and crafts, and 24-hour security. You’ll be close to medical facilities, restaurants, multiple lakes, The Villages, and just a short drive to Orlando. HOA approval is required for new buyers with a one-time **$250 transfer fee**. ---
Listing is courtesy of: RE/MAX PREMIER REALTY (352-460-4396)
Listing Agent: Brad Craycraft (859-983-1440)
803 N SHORE DR, LEESBURG, FL 34748
$369,000246 Days on yellowkey MLS ID: O6336921
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1834 Built: 1968 Tax: $1,556 (2024)Community: Leesburg Beverly ShoresSingle Family
Taxes:$1,556
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Beautiful ranch home situated on a corner, double lot on Leesburg's Beverly Shores. A quiet natural setting with access to the Chain of Lakes and just a block away from water access, docks and fishing. Just minutes to downtown Leesburg and parks. The quality of this well maintained home will catch your attention! The brick exterior is solid and in excellent condition and terrazzo flooring. House has a life time rhino covering and windows and screens have a lifetime warranty. There is a side room that could be converted to a bedroom or potential "mother-in-law" suit. Several renovations have been done including the roof and windows replaced in 2017; AC replaced in 2012 & newer flooring throughout. The spacious floor plan is great for entertaining and has a separate office/storage room with private entrance which could be converted to an additional bedroom. The oversized, finished garage is great for storage and parking but could be great to turn into a home gym or ever turn into additional living space. An additional carport is built off of the house as well. This is a great place to call “home” scheduled your showing today.
Listing is courtesy of: PIXEL REALTY (352-678-9405)
Listing Agent: Benjamin Larbus (419-231-0668)
2123 ANOKA WAY, LEESBURG, FL 34748
$299,50021 Days on yellowkey MLS ID: O6394935
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1612 Built: 2005Monthly Fee: $35 Tax: $3,548 (2025)Community: Overlook/Lk GriffinSingle Family
Taxes:$3,548
Remarks: Welcome to 2123 Anoka Way in Leesburg, FL — a beautifully updated home that blends modern upgrades with a lovely curb-appeal, comfort, space, and natural light. From the moment you walk in, you’re greeted by vaulted ceilings and an open, airy feel that carries throughout the home. With two separate, generously sized living areas, this layout offers flexibility for entertaining and relaxing! The kitchen has been thoughtfully refreshed with brand new quartz countertops, freshly painted and sealed cabinetry, a stylish backsplash, and new appliances — giving it a clean, modern feel that truly stands out. Major updates have already been taken care of for you, including a brand new roof (December 2024) and a NEW AC system (2025), offering peace of mind for years to come. The home also features updated LVP flooring throughout and fresh interior paint, making it completely move-in ready. Natural light pours into the home, highlighting the finishes and creating a warm, inviting atmosphere in every room. Step outside and you’ll find a meticulously maintained lawn and landscaping, adding to the overall pride of ownership and curb appeal. If you’re looking for a home that checks all the boxes — updated, spacious, and truly turnkey — this is one you don’t want to miss.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Brian Batiz Salazar (407-693-1033)
5024 LONG MEADOW DR, LEESBURG, FL 34748
$329,90048 Days on yellowkey MLS ID: G5109100
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1847 Built: 2001Monthly Fee: $180 Tax: $3,734 (2025)Community: Plantation At Leesburg Long Meadow VillageSingle Family
Taxes:$3,734
Remarks: +++ Check Out The New Price +++ Welcome to The Plantation at Leesburg and this inviting golf course home with a scenic view of the 4th hole of Cranes Roost Golf Course. Enjoy the landscape from the screen-enclosed lanai and the generous windows of the Florida room, creating a bright and comfortable space to relax and take in the setting. Tucked near the end of a cul-de-sac, the location offers a quieter feel with minimal drive-by traffic, and it’s also just a short walk to the community’s popular pool and pickleball courts. This concrete block and stucco home features 2 bedrooms, plus office/den, 2 baths, and a tall garage with excellent storage. Since 2024, the home has seen meaningful improvements, including fresh interior paint, updated laminate flooring throughout most of the living areas, and new carpet in all three bedrooms. The primary bathroom has been thoughtfully updated by removing the jetted garden tub and adding beautiful cabinetry and a new vanity with expanded storage, along with a comfortable, easy-access shower and a spacious walk-in closet. The garage is equally impressive with new gray epoxy floor finished with black and blue flakes for a clean, finished look. Additional updates include a new hot water heater (2025) and a new backflow valve on the irrigation system (2026). The roof was replaced in 2018 and the A/C has been maintained. The Plantation at Leesburg is a gated, 55+ community offering two 18-hole championship golf courses, three pools and community centers, and an active calendar of clubs and amenities for a variety of lifestyles. Schedule your showing and come see the view, the updates, and the easy Florida living this home offers.
Listing is courtesy of: CARLINO REAL ESTATE GROUP INC (352-326-2662)
Listing Agent: Marty Bouhall (352-326-2662)
344 HAWTHORNE BLVD, LEESBURG, FL 34748
$139,00027 Days on yellowkey MLS ID: G5110140
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1974Monthly Fee: $397 Tax: $1,449 (2025)Community: Hawthorne At Leesburg A CoopMobile Home
Taxes:$1,449
Remarks: Rare opportunity to own a fully furnished home tucked away on a quiet cul-de-sac, perfectly positioned to capture peaceful views of the woods and a county pond at 344 Hawthorne Blvd. This two-bedroom, two-bath residence offers a setting that feels both private and connected to nature, creating a calm and inviting atmosphere from the moment you arrive. The home welcomes you with standout curb appeal, featuring clean, crisp vinyl siding and a recently serviced roof for added peace of mind. Inside, the home is move-in ready, reflecting a level of care and upkeep that’s immediately noticeable. Updated windows throughout, excluding the Florida room, bring in natural light while enhancing efficiency. Beautiful laminate flooring flows through the main living areas, complemented by built-in dining room cabinetry that adds both character and practical storage. The kitchen has been thoughtfully updated with striking countertops and a stylish backsplash, offering a space that is as functional as it is visually appealing. A spacious, extra-large 8 x 16 utility room provides exceptional storage and workspace. Both bathrooms feature walk-in showers, including a well-appointed primary bath designed for ease and comfort, as well as a walk-in shower in the guest bath for added convenience...............Hawthorne at Leesburg is an active, resident owned, 55+ cooperative, waterfront, gated community, with beautifully landscaped grounds, lakes with illuminated fountains and a relaxing and comfortable gazebo. The affordable monthly maintenance fee of $397 includes water, sewer, lawn mowing, private emergency services and storage space for recreational vehicles, boats, trailers and much more! The beautiful clubhouse is complete with a full-time program coordinator, more than 100 different activities and seating for 550. It has a hospitality lounge, card rooms, craft rooms, billiard room, fitness center, library, fine arts room and many more. There is excellent fishing, outdoor geo-thermally heated pool and two enclosed therapeutic pools. Hawthorne boasts a private marina monitored by an electronic security system with over 120 boat slips and access to the Harris Chain of Lakes and beyond.
Listing is courtesy of: HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC. (352-360-6226)
Listing Agent: Maria Crisostomo (352-626-2914)
25527 OAK ALY, LEESBURG, FL 34748
$257,500411 Days on yellowkey MLS ID: G5093909
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1518 Built: 1992Monthly Fee: $165 Tax: $1,656 (2024)Community: Plantation At Leesburg Belle GroveSingle Family
Taxes:$1,656
Remarks: *** Fresh Price Improvement — Now $257,500 *** Great opportunity in The Plantation at Leesburg! This easy-living Cayman floor plan sits on a shady, low-maintenance lot and offers a comfortable, well-laid-out interior with several flexible spaces. You’re welcomed by an open living area with a convenient pass-through to the kitchen. The separate dining room features a bright bay window and a recessed china cabinet nook, and it could easily be repurposed as a den or possible third sleeping space depending on your needs. The breakfast nook is also accented by a bay window, bringing in great natural light. The kitchen offers plenty of cabinet storage plus a pantry. Out back, the enclosed lanai features easy-to-open sash sliding windows—perfect for letting in morning light and fresh air. Just outside is a shaded patio ideal for grilling or relaxing, with no rear neighbors and a peaceful view toward the driving range. Enjoy added privacy from the rear hedge and take in those brilliant Florida sunsets. The primary suite is generously sized (12' x 15') and opens to a large bath with double sinks, a spacious walk-in shower, and a walk-in closet. The guest bedroom is also comfortably sized with a built-in closet. The garage floor has been freshly painted and the garage is 1.5 cars wide with a deeper 7' x 8' storage nook—great for extra storage and can potentially accommodate a golf cart. Major updates include a roof replacement in June 2021, and the A/C has been maintained on a regular 6-month schedule. The Plantation at Leesburg is a gated, 55+ community known for its active lifestyle, featuring three community centers with pools, hot tubs, meeting rooms and more, plus amenities like archery, billiards, fitness rooms, and two championship 18-hole golf courses. Schedule your showing and come see what easy Florida living looks like!
26601 BULL RUN, LEESBURG, FL 34748
$361,00019 Days on yellowkey MLS ID: O6396041
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1913 Built: 2006Monthly Fee: $105 Tax: $6,295 (2025)Community: Leesburg Arlington Ridge Ph 1-ASingle Family
Taxes:$6,295
Remarks: Beautiful 2 Bedroom 2 Bathroom Dream Home Located in the Premier 55+ Golf Course Community of Arlington Ridge. This home boasts wall-to-wall upgrades with a newer roof, gutters, A/C system, flooring and much more. The open floorplan offers a kitchen overlooking the living room with a dinette area between and tile floors throughout the common areas. The kitchen features wood cabinets, a tile backsplash, stone countertops, a walk-in pantry and stainless-steel appliances including the refrigerator, dishwasher and microwave. The home also features two wonderful bedrooms with a den/office space that can be used as a bonus room, office or for guest. The community of Arlington Ridge offers the lifestyle that you've been looking for with world-class amenities including an 18-Hole Golf Course, on-site restaurants, tennis courts, pickleball courts, bocce ball, softball, community pools, hot tub and a state-of-the-art fitness center. The full-service spa offers massages, manicures, pedicures, and more. Please call to schedule a showing today!
Listing is courtesy of: MIGHTY REALTY INC (407-403-6540)
Listing Agent: Joann Bonilla (317-435-5235)
4834 INDEPENDENCE TRL, LEESBURG, FL 34748
$250,000107 Days on yellowkey MLS ID: G5105914
0 Days Off yellowkey (back on 4/3/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1772 Built: 2011Monthly Fee: $126 Tax: $5,756 (2025)Community: Leesburg Arlington Ridge Ph 02Single Family
Taxes:$5,756
Remarks: Under contract-accepting backup offers. **MOTIVATED SELLER - BRING ALL OFFERS!!** CHAMPIONSHIP GOLF COURSE VIEWS! Welcome to Leesburg's Premier 55+ Golfing Community of Arlington Ridge. QUIET LOCATION at End of Cul-de-sac. Fabulous OPEN Split Floor Plan on this CLEAN & BRIGHT Block/Stucco 2 Bed / 2 Bath Villa with Bonus Den/Dining Room Space. This home offers a Spacious Kitchen with abundance of rich 36" Maple Cabinets, Built-In Oven & GAS Cooktop! Kitchen Breakfast Bar opens to Large Great Room and Screened Sunny 17'x17' Southern Exposure Lanai OVERLOOKING GOLF COURSE! Tile Floors at Entry, Kitchen & Bathrooms. Primary Bedroom is generous and offers Large WALK-IN Closet & En-Suite Bath with Soaking Tub. Private Guest Bedroom with Bay Window & Adjacent Guest Bath. TALL 9'+ CEILINGS with Solar Tube at Front Foyer Entrance. NEW ROOF 2024! Arlington Ridge is an Active 55+ Golf Community, with 2 Resort-Style Pools, State-of-the-Art Fitness Facility, Tennis & Pickleball Courts, and Numerous On-going Activities. Enjoy the On-site Restaurant/Pub & Community Movie Theater. Arlington Ridge offers a STUNNING 18 Hole CHAMPIONSHIP GOLF Course. Security Guards at Entrance are On-Duty 24/7. Back Resident-Only Gate for ease of entry. Low HOA @ $126/Month for Lawn Mowing/Edging/Blowing, TV/CABLE with 200+ Channels, High-Speed Internet, Insurance, Lighted Sidewalks/Streets, & Amenities that are Resident/Guest Exclusive! Close to 3 Hospitals, Multiple Private-Practice Physician offices & Minutes from Shopping, Restaurants, Hardware, Groceries, Urgent-Care Centers, Banks, & More! Beautifully Landscaped with NO HOMES ACROSS THE STREET. Arlington Ridge is the best kept secret in Leesburg!! Don’t miss out on this Lovely Home!
Listing is courtesy of: REALTY EXECUTIVES IN THE VILLAGES (352-753-7500)
Listing Agent: Gail Damon (352-626-3121)
24914 CRANES ROOST CIR, LEESBURG, FL 34748
$275,900168 Days on yellowkey MLS ID: G5104174
1 Days Off yellowkey (back on 2/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1801 Built: 1999Monthly Fee: $180 Tax: $1,350 (2024)Community: Plantation At Leesburg GolfviewSingle Family
Taxes:$1,350
Remarks: Under contract-accepting backup offers. Snowbird approved!!!Friendly neighbors invite you to join in the fun. This villa is virtually maintenance free so you can enjoy all the Plantation at Leesburg has to offer.Interior has been upgraded with luxury vinyl plank flooring, gas stove and tankless water heater. . Plenty of room inside and out with 3 bedrooms, living/diningroom and family room. Additionally a 3-season porch and additional patio for chillin and grillin. Patio has electronic awning with mood lighting. Spend your days swimming, in one of 4 heated pools, golfing 36 holes of golf, pickleball, softball, horseshoes, bocce ball, card games, water aerobics, crafting, boating, fishing, exploring Florida. Lawn care trimming and fertilizing done regularly and pressure washing once a year as part of the neighborhood hoa. Orlando Parks less than an hour away. Plantation is located within minutes of all that The Villages have to offer in restaurants and entertainment. You can retire here or snowbird here in this guard gated 55 plus community.
Listing is courtesy of: FLORIDA PLUS REALTY, LLC (352-901-9100)
Listing Agent: Sandy Twito (352-901-9100)
25251 CRANES ROOST, LEESBURG, FL 34748
$259,90083 Days on yellowkey MLS ID: G5107331
3 Days Off yellowkey (back on 4/3/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1313 Built: 2001Monthly Fee: $180 Tax: $3,342 (2026)Community: The Plantation At LeesburgSingle Family
Taxes:$3,342
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully maintained 2-bedroom, 2-bath single-family residence located in a gated 55+ golf community offering relaxed, resort-style living. Filled with abundant natural light and a cozy from porch, this bright and airy home features an open floor plan with both a formal living area and a comfortable family room, creating distinct yet connected spaces for entertaining and everyday living. The eat-in kitchen opens to the living room, while the separate dining room is attached to the family room, with the kitchen thoughtfully positioned between the two—providing both functionality and privacy while maintaining an open, welcoming flow. Spacious bedrooms offer comfort and retreat, and the home’s layout enhances its open yet well-defined feel. Recent updates include a roof in 2021, resurfaced kitchen counters and master bath shower, new shower glass enclosures, fresh interior paint, front door paint and garage door paint! The yard was also resoded! Enjoy additional living and entertaining space in the screened-in lanai, perfect for morning coffee or evening gatherings. Residents have access to outstanding amenities including three community pools, two golf courses, a clubhouse with restaurant, tennis courts, and pickle ball courts. Golf View features a secondary quarterly HOA covering lawn maintenance and granting exclusive access to a private pool reserved for Golf View residents. This home offers easy, low-maintenance living in a vibrant community designed to enjoy every day.
Listing is courtesy of: CENTURY 21 MYERS ROSE REALTY (352-536-0100)
Listing Agent: Ashlee Mohammed (407-489-5458)
2306 EDGEWATER AVE, LEESBURG, FL 34748
$135,50071 Days on yellowkey MLS ID: G5107988
4 Days Off yellowkey (back on 3/23/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1940 Tax: $1,317 (2025)Community: Edgewater Heights CorrSingle Family
Taxes:$1,317
Remarks: Under contract-accepting backup offers. Solid Bungalow in Established Leesburg Neighborhood – Possible 2 Bedroom Conversion. Great opportunity for investors or first-time buyers. Currently configured as a 1-bedroom, this home was previously a 2-bedroom and offers potential to convert back if desired. This home features hardwood floors and a functional, easy-flow layout with good natural light. Located on a quiet dead-end street in a stable, established neighborhood primarily made up of long-term residents and working homeowners. Convenient to schools, shopping, parks, and everyday necessities. Property is centrally located in Leesburg with easy access to surrounding areas, the Harris Chain of Lakes, and a short drive to The Villages. Suitable for rental, light renovation, or owner-occupant purchase. Seller will consider all offers.
Listing is courtesy of: EXIT REALTY TRI-COUNTY (352-385-3948)
Listing Agent: Fred Slotnick (352-455-1918)
33236 GRAND CYPRESS WAY, LEESBURG, FL 34748
$279,247506 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
Taxes:$3,053
Tax Year: 2023
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
$229,24788 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
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
$214,247241 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
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
$89,24781 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!
109 N OAKLAND ST, LEESBURG, FL 34748
$242,400204 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
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
$149,00054 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
$215,00020 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
$389,90092 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)
2316 N GRIFFIN DR, LEESBURG, FL 34748
$545,00026 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)
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