Location: Pennbrooke Fairways, Leesburg
Do Not Show Listings
752 OLD OAKS LN, LEESBURG, FL 34748
$224,24747 Days on yellowkey MLS ID: G5108177
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1620 Built: 2000Monthly Fee: $265 Tax: $998 (2025)Community: Pennbrooke FairwaysSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$998
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: FRESHLY PAINTED 2 BEDROOM/2 BATH HOME WITH A 3RD ROOM FOR OFFICE OR DEN WITH NO CLOSET. This 2 car garage home has a new roof in 2019 and a new heat pump in 2024. 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! Expect the unexpected!
Listing is courtesy of: MAXREV LLC (904-460-2789)
Listing Agent: Jayne Marvin (352-205-5379)
33236 GRAND CYPRESS WAY, LEESBURG, FL 34748
$279,247488 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
32747 TIMBERWOOD DR, LEESBURG, FL 34748
$229,24770 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
$214,247223 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
32747 WESTWOOD LOOP, LEESBURG, FL 34748
$219,24750 Days on yellowkey MLS ID: G5108173
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1997Monthly Fee: $265 Tax: $2,408 (2025)Community: Pennbrooke FairwaysSingle Family
Taxes:$2,408
Remarks: LOVELY 2/2 BRENTWOOD MODEL IN PENNBROOKE FAIRWAYS... 55+ COMMUNITY NOT FAR FROM THE VILLAGES, SHOPPING & RESTAURANTS. This home features an enclosed lanai, Roof replacement in 2017, newer HVAC in 2018, NEW WINDOWS in 2024 and a NEW DRIVEWAY with river rock coating. Gorgeous flooring, stainless appliances, spacious walk-in shower with frameless door and more... come see for yourself! 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 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, dining, and nightly entertainment and just minutes to Downtown Leesburg. Make your appointment to see this home today!
610 COTTAGE PARK LN, LEESBURG, FL 34748
$89,24763 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!
548 GRAND VISTA TRL, LEESBURG, FL 34748
$329,000158 Days on yellowkey MLS ID: G5103810
REDUCED by $20,900 (6.0%) on 04/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1999 Built: 2001Monthly Fee: $265 Tax: $3,137 (2024)Community: Pennbrooke FairwaysSingle Family
Taxes:$3,137
Remarks: One of a Kind GOLF Frontage Home with WATER VIEWS PLUS a large 2 car garage with a BONUS Room in the desirable 55+ Pennbrooke Fairways! This 3 Bedroom 2 bath is 1999 square feet of Living space. The primary bedroom is 17 x 13 and features a large walk-in closet and an ensuite with a water closet, 2 separate vanities, dual sinks and a large walk-in shower. The 2 guest bedrooms are spacious in size (one of the bedrooms does not have a closet) and share a bathroom nearby. The Inside laundry room is oversized and has lots of storage space and a utility sink. This home showcases lots of natural light in addition to the 4 solar tubes. Lovely finished glass enclosed Lanai has wood like ceramic tile flooring and breathtaking Water & Golf Course views! New roof in 2020,New HVAC in 2021 and water heater in 2015. Kitchen & bathrooms feature granite countertops. Also the kitchen has newer stainless steel appliances, white cabinets, a desk area as well as eat-in space overlooking the water and golf course views. Living room and Dining room combo has Luxury Vinyl plank floors. Between the inside Laundry room and garage is a 20x10 workshop that is heated and cooled (not included in the living sq ft) which could be a great Man Cave, Craft Room or storage! The low $265 Monthly HOA fee includes grass cutting, Hi-speed internet, cable and amenities. Pennbrooke Fairways is a lovely Gated Golf community. 27 holes of golf, pro shop and restaurant. Two recreation Centers, 2 pools and Fitness Center, Shuffleboard, pickleball, tennis, softball, horse shoes, water volleyball and cornhole. If you like inside activities, there are darts, billiards, Line dancing, Quilting, Art room and over 100 Clubs. Pennbrooke is convenient to Shopping and dining and 6 miles East of The Villages Brownwood Paddock Town Square.
Listing is courtesy of: CENTURY 21 ALTON CLARK (352-728-2121)
Listing Agent: Regina Rodriguez (352-269-0450)
347 BENTWOOD DR, LEESBURG, FL 34748
$269,24719 Days on yellowkey MLS ID: G5109411
2 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1643 Built: 2004Monthly Fee: $265 Tax: $3,679 (2025)Community: Pennbrooke FairwaysSingle Family
Taxes:$3,679
Remarks: ADORABLE 3 BEDROOM AND 2 BATH HOME IN Pennbrooke Fairways, a 55+ Community! NO CARPET IN MAIN LIVING AREAS. ENCLOSED LANAI WITH A PRETTY BACKYARD SPACE FOR RELAXING. INSIDE LAUNDRY! LOVELY LANDSCAPING! EXPECT THE UNEXPECTED! 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! Expect the unexpected! ROOF 2022
32833 TIMBERWOOD DR, LEESBURG, FL 34748
$299,00023 Days on yellowkey MLS ID: G5109388
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1975 Built: 1999Community: Pennbrooke FairwaysSingle Family
Taxes:
Tax Year:
Remarks: This beautiful Castle Bay model home is located in Pennbrooke Fairways, a gated 55+ community! This home features 3 bdrs, 2 baths, and a 2 car garage. Step into the spacious open floor plan which offers plenty of room for entertaining. This home is a perfect combination of comfort, style and scenic surroundings of the golf course and pond. No rear neighbors. Flooring through out (no carpet). All furniture and contents will stay. The roof was replaced in 2018, HVAC (2020) and hot water heater 2025. The large kitchen has plenty of counter space, blt in desk and a cozy dinette. The primary bdr has plenty of ample space including an en-suite that has 2 walk-in closets, 2 vanities with their own sinks, garden tub and a separate step in shower. Check out the inside laundry rm that has washer, dryer, several cabinets, a large storage closet, wash sink and a stand alone upright freezer. Enjoy the views of the golf course and pond while relaxing with your favorite drink in the large screened lanai.Pennbrooke Fairways is a 55+ community with a low monthly HOA fee of $265.00 that includes cable, internet, lawn mowing, edging, boat & RV parking and storage! There is a 24 hour guarded security gate, pools, golf courses, restaurant, pro shop, fitness center, tennis courts, bocce ball, pickleball, cornhole, shuffleboard plus 2 rec centers. Pennbrooke is conveniently located with in minutes of Publix, Walgreens and The Villages Brownwood Town Square...where there is plenty of shopping, dining, medical and entertainment.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-787-6966)
Listing Agent: Dalemarie Lamb-Witter (352-551-7615)
33409 PENNBROOKE PKWY, LEESBURG, FL 34748
$329,247 MLS ID: G5092982
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2111 Built: 2003Community: Pennbrooke FairwaysSingle Family
Remarks: OFFERED FURNISHED!! PLUS - BRAND NEW STAINLEES STEEL KITCHEN APPLIANCES! EXPECTED THE UNEXPECTED! 3/2 HOME PLUS OVERSIZED BONUS ROOM...... NOT TO MENTION GOLF CART GARAGE AND STUNNING GOLF VIEWS!!! THIS IS A MUST SEE! THIS IS A HIDDEN GEM OF A COMMUNITY!!! Pennbrooke is located just 10 minutes south of The Villages and only 50 minutes from Orlando. The Pennbrooke Fairways golf course offers golfers two executive nines and one regulation nine to appeal to all skill levels while offering a fun, challenging golf experience. Pennbrooke offers RV and Boat Storage with Dump and Wash Stations & 24 hour Gated Security. The community center offers a Hair Salon & Library and Real Estate Community Office onsite. Your HOA included cable/internet service and even Lawn cutting services, pools and club rec centers, many fun activities are planned throughout the year!!! Conveniently located within minutes from grocery stores, The Villages, Brownwood Town Square, and Downtown Leesburg. THIS IS A RARE FIND IN PENNBROOKE, 3 BEDROOM, OVERSIZED BONUS ROOM AND GOLF CART GARAGE HOME! THIS HOME IS A MUST VISIT! SEE ALL THIS HOME HAS TO OFFER FOR YOURSELF! SPACIOUS THROUGHOUT THIS HOME! VIEWS FROM BONUS ROOM, KITCHEN, LIVING ROOM, THIS HOME GIVES YOU THE FEEL OF INDOOR-OUTDOOR LIVING WITH SUCH VIEWS FROM SO MANY ROOMS!!! ADDED BONUS- ROOF 2020, HVAC 2017. PENNBROOKE AT ITS BEST! VISIT THIS RARE FIND IN PENNBROOKE!
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