Leesburg, FL Homes for Sale under $300,000

• 

  

  

  /42

  $299,900

  • 3 Beds
  • 3 Baths
  • 2,316 Sq Ft

  34847 Learn Rd, Leesburg, FL 34788

  Home Sweet Home come and see this beautiful 3 bedrooms 2 baths single family home. It features large living room, dining room combo with wood floors and a family room with a fire place, large galley kitchen, large spacious bedrooms and a converted garage for extra room and storage. Additional to that a detached single car garage. All found in a well established community. Sitting on over a

  Claudia Montes LPT REALTY, LLC

  34847 Learn Rd, Leesburg, FL 34788
• 

  

  

  /25

  $224,900 Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  1313 Vine St, Leesburg, FL 34748

  One or more photo(s) has been virtually staged. Price Improvement! Seller Motivated. Charming & Unique Home with BONUS LOFT ROOM!Welcome to this beautiful 1/2 Duplex and one-of-a-kind home, offering the perfect blend of character and modern convenience. This well-maintained property features spacious living areas, a thoughtfully designed layout, and an inviting atmosphere.A

  Jennifer Gotlewski OLYMPUS EXECUTIVE REALTY INC

  1313 Vine St, Leesburg, FL 34748
• 

  

  

  /16

  $210,000

  • Land
  • 3.48 Acres
  • $60,345 per Acre

  3150 Bright Lake Cir Unit 71, Groveland, FL 34736

  3.48 Lot Acres for this price! This won’t be on the market for long. It’s a gated community in Clearwater Reserve, one of central Florida’s best country estate gated communities. This lot has over 150,000 square feet, giving you ample space to build your dream home. You won’t have any rear neighbors on this waterfront homesite. There are no time requirements to build, and you can bring your own

  Rene Guillen Portillo LA ROSA REALTY SUCCESS LLC

  3150 Bright Lake Cir Unit 71, Groveland, FL 34736
• 

  

  

  /60

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,483 Sq Ft

  5004 Saint Andrews Arcade, Leesburg, FL 34748

  One or more photo(s) has been virtually staged. ***NEW INTERIOR PAINT COMING SOON!***Views of the 16th hole! Come see this Baron Model home with two large bedrooms, two bathrooms and an enclosed Florida Room overlooking the Monarch Golf Course! The exterior has a stacked stone accent with vinyl siding, a new postlamp, shade trees, no neighbors to the right, and a welcoming landscape. Paver

  Tonya Tibbetts FLORIDA PLUS REALTY, LLC

  5004 Saint Andrews Arcade, Leesburg, FL 34748
• 

  

  

  /48

  $299,999

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  21721 Loch Haven Pass, Leesburg, FL 34748

  Move-In Ready Block Home in Royal Highlands – Newer Roof & No Renovation Needed! Welcome to Royal Highlands, a premier 55+ gated golf course community in sunny Central Florida, known for its vibrant lifestyle, top-notch amenities, and beautifully maintained homes. If you're looking for peace of mind and zero hassle, this home checks all the boxes—block construction, a newer roof (2018), fresh

  Melissa Samar PICKET FENCE REALTY LLC

  21721 Loch Haven Pass, Leesburg, FL 34748
• 

  

  /27

  $287,900

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft

  32712 Timberwood Dr, Leesburg, FL 34748

  Beautiful 3 bedroom 2 bath home on a premium cul-de-sac homesite with pond view in the guard gated golf community of Pennbrooke Fairways. This home features a brand new roof, new stainless steel appliances, new carpet and tile flooring, new paint inside and out, new hot water heater and 2019 AC system. The primary bedroom has a large walk-in closet and dual vanity. Bedroom 3 has a built-in Murphy

  Gerry Klaus VELEZ COURTESY MANAGEMENT

  32712 Timberwood Dr, Leesburg, FL 34748
• 

  

  /60

  $209,000

  • 2 Beds
  • 2 Baths
  • 1,310 Sq Ft

  312 Brigadoon Cir Unit 12C, Leesburg, FL 34788

  BEST PRICE, BEST LOCATION AND ADORABLE SHOWPLACE! THE PRICE JUST GOT BETTER -AND- LENDER PAID 2-1 INTEREST RATE BUYDOWN-REDUCED MONTHLY PAYMENTS FOR THE FIRST 2 YEARS! Why wait? Act Now Before It’s Gone! NEW Roof (under 1 year old) – big savings for YOU! Imagine waking up to picturesque waterfront views in the highly sought-after 55+ community of Scottish Highlands—now at an even better price!

  Robin Skaggs COLDWELL BANKER VANGUARD EDGE

  312 Brigadoon Cir Unit 12C, Leesburg, FL 34788
• 

  

  /36

  $248,000

  • 2 Beds
  • 2 Baths
  • 1,673 Sq Ft

  5505 Tangelo St, Leesburg, FL 34748

  This one-of-a-kind unique home is nestled in the sought after Award - Winning Gated Golf Community. Featuring a rare double owner’s suite layout plus a den, this residence offers flexibility, comfort, and space. The open split floor plan is filled with natural light, especially in the kitchen, which boasts ample counter and storage space along with a sunny breakfast area.The dining and

  Mary Jane Grimes CENTURY 21 MYERS REALTY

  5505 Tangelo St, Leesburg, FL 34748
• 

  

  /38

  $234,247

  • 3 Beds
  • 2 Baths
  • 1,611 Sq Ft

  32622 Oak Park Dr, Leesburg, FL 34748

  MINI MAKEOVER! EXPECT THE UNEXPECTED!!!!!! Interior painted in livining room, dining area and the kitchen, new light fixture in kitchen nook, NEW CARPET in living & dining area...garage walls being painted on Thursday. Lanai has been painted and landacaping has been enhanced. This 3/2 home is listed below market value and ready for new owners. If you've been looking for a private setting, THIS

  YOUR 24/7 Real Estate Team MAXREV LLC

  32622 Oak Park Dr, Leesburg, FL 34748
• 

  

  /69

  $244,900

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft

  24947 Cranes Roost Cir, Leesburg, FL 34748

  BELOW CURRENT APPRAISED VALUE. The 3 bedroom 2 bath home located on a premium private lot in the Village of Golfview can be a very comfortable home with a little love.Golfview Village is the only Village in The Plantation at Leesburg with it's own private pool for Village members only. You will notice there is room to lounge when stepping up to the front porch. The inviting entrance and

  Karen LaMantia CARLINO REAL ESTATE GROUP INC

  24947 Cranes Roost Cir, Leesburg, FL 34748
• 

  

  /25

  $210,000

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  201 N East St, Leesburg, FL 34748

  Nestled on a spacious corner lot, this charming 1940s bungalow-style home offers a solid concrete block foundation and a classic, welcoming layout. Perfect for a handy first-time homebuyer or a savvy investor, this property boasts brand-new carpeting, a freshly painted interior, and a new air conditioning system for year-round comfort.The inviting screened-in front porch is the ideal spot to

  Dorothy Williams FLORIDA BREEZE REALTY

  201 N East St, Leesburg, FL 34748
• 

  

  /5

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  206 Cooke St, Leesburg, FL 34748

  This home is back on the market!!! Buyer financing fell through. This home is nested comfortably in a nice & quiet neighborhood in Leesburg, FL. This home feature 3 bedrooms 2 bathrooms and a 1 car garage with over 1,635 sq ft of living space built in 1954. This home also feature newer windows that was replaced in 2018 and the roof was replace in 2021.

  Gerard Corbin COMBS PREMIER REALTY GROUP

  206 Cooke St, Leesburg, FL 34748
• 

  

  /16

  $209,900

  • 2 Beds
  • 2 Baths
  • 910 Sq Ft

  12141 Lake Pines Rd, Leesburg, FL 34788

  For your own home or as an income investment this is the property for you! Canal frontage to Lake Eustis. 14' singlewide manufactured home. It has been used very successfully as a short term rental property. Roof over porch and shed. Fenced backyard. NO HOA!!!Located only 50 minutes to downtown Orlando and all theme parks. An hour to Orlando International Airport and the beautiful East

  Michell Middleton CENTURY 21 SPOUSES WITH HOUSES REALTY

  12141 Lake Pines Rd, Leesburg, FL 34788
• 

  

  /45

  $299,247

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  33236 Grand Cypress Way, Leesburg, FL 34748

  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

  YOUR 24/7 Real Estate Team MAXREV LLC

  33236 Grand Cypress Way, Leesburg, FL 34748
• 

  

  /74

  $299,500

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  21630 King Henry Ave, Leesburg, FL 34748

  *** ONE OR MORE PHOTOS HAVE BEEN VIRTUALLY STAGED *** ***NEW ROOF July 2025 !!! *** Welcome home to Royal Highlands!! A highly sought-after 55+ GATED/POOL community!! Simplicity and Serenity galore!! This is your opportunity to live in one the most desirable neighborhoods!! MOVE IN READY!! NO DIRECT REAR NEIGHBORS!! PLUS, A SPECTACULAR “TOUCH OF NATURE” backyard on a PREMIUM LOT!! This

  Steven Boone EXIT REALTY TRI-COUNTY

  21630 King Henry Ave, Leesburg, FL 34748
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  /28

  $250,000

  • 4 Beds
  • 2 Baths
  • 2,096 Sq Ft

  1009 Perkins St, Leesburg, FL 34748

  This charming 4-bedroom, 2-bathroom home offers the perfect blend of comfort and style. The kitchen features sleek stainless steel appliances, gorgeous granite countertops, and timeless white cabinetry. With four well-sized bedrooms, there's plenty of space for everyone, guests, or a home office. The two full bathrooms offer both functionality and relaxation. Don’t miss the opportunity to own

  Cheryl Fabian MAINSTAY BROKERAGE LLC

  1009 Perkins St, Leesburg, FL 34748
• 

  

  /30

  $240,000

  • 4 Beds
  • 3 Baths
  • 1,505 Sq Ft

  112 S Moss St, Leesburg, FL 34748

  Welcome to your dream home! This stunning 4-bedroom, 3-bathroom residence boasts a bright and inviting living/dining room combo, perfect for entertaining or gatherings. The kitchen features elegant granite countertops and modern stainless steel appliances, making it a chef's delight. Step outside to discover a spacious backyard, ideal for outdoor activities or relaxing in the sun. With its

  Cheryl Fabian MAINSTAY BROKERAGE LLC

  112 S Moss St, Leesburg, FL 34748
• 

  

  /38

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  32857 Timberwood Dr, Leesburg, FL 34748

  BEAUTIFUL GOLF COURSE HOME!! Located in Pennbrooke Fairways a 55+ gated community! This desirable block/stucco Mclean model home features 3 bdrs, 2 baths, inside laundry rm, and a 2 car garage. The spacious open floorplan makes it a perfect space for entertaining family and friends. Roof replaced 2015. Both bathrooms have been nicely updated. The Mstr suite offers a walk-in closet and a large

  Dalemarie Lamb-Witter ERA GRIZZARD REAL ESTATE

  32857 Timberwood Dr, Leesburg, FL 34748
• 

  

  /20

  $299,000

  • Land
  • 0.52 Acre
  • $575,000 per Acre

  700 Physicians Ct, Leesburg, FL 34748

  Prime Development Opportunity in Leesburg!Unlock the potential of this half-acre lot, ideally suited for medical or professional development. Located at the highly desirable corner of Physicians Court and Medical Plaza Drive, this parcel offers an exceptional location for a doctor’s office, assisted living facility, or healthcare practice.Surrounded by established medical and

  Brandon Rimes KELLER WILLIAMS REALTY- PALM H

  700 Physicians Ct, Leesburg, FL 34748
• 

  

  /39

  $229,000

  • 3 Beds
  • 2 Baths
  • 1,546 Sq Ft

  34811 Barger Ct, Leesburg, FL 34788

  Welcome to this one-owner, well-maintained home in Leesburg! This home features 3 bedrooms that all have WALK-IN CLOSETS, 2 full bathrooms, split-bedroom floorplan, spacious living and dining combo with built-in cabinets in the dining space, a nook in the kitchen with cafe-style doors and loads of natural light that flows through. Making up the OVER 2800 total square footage, we have 1546 square

  Mary Palerino WEICHERT REALTORS HALLMARK PRO

  34811 Barger Ct, Leesburg, FL 34788
• 

  

  /40

  $299,999

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  34323 Island Dr, Leesburg, FL 34788

  **Price Reduction**This property is ideally situated along a deep-water canal for boat clearance that connects directly to LAKE EUSTIS, one of the 7 HARRIS CHAIN of LAKES. This beautiful 3/2 chain of lakes home is in a 55+ community and is a paradise for fishing, boating and nature lovers with a quiet and fun community. It's a great life, drop your boat in the water to fish in the morning, water

  Cindy Sonne SONNE REAL ESTATE INC

  34323 Island Dr, Leesburg, FL 34788
• 

  

  /60

  $292,000

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft

  5430 Sir Churchill Dr, Leesburg, FL 34748

  Back on the market—previous contract fell through due to no fault of the home—so here’s your second chance to make it yours!Welcome to your custom-built home in the sought-after 55+ community of Royal Highlands, perfectly situated on an oversized lot with pristine views and peaceful surroundings. This inviting 3-bedroom, 2-bathroom residence blends comfort and style. Step inside to a

  Tracy Campoli RE/MAX FREEDOM

  5430 Sir Churchill Dr, Leesburg, FL 34748
• 

  

  /46

  $285,900

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  21242 Braveheart Dr, Leesburg, FL 34748

  Welcome to the beautifully furnished 21242 Braveheart Dr., located in the heart of the Royal Highlands 55+ Golf Community! This home is Clean and Move In Ready while still allowing for plenty of updates and your own personal touches. The Regent Model is the perfect place to call home, featuring 3 bedrooms, 2 baths, and nearly 2,000 sq. ft. of living space. Situated on one of the community’s most

  Katherine Nguyen THE NAVY HOUSE

  21242 Braveheart Dr, Leesburg, FL 34748
• 

  

  /45

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft

  5610 King James Ave, Leesburg, FL 34748

  One or more photo(s) has been virtually staged. Gated Community Charming home, Customized Topaz model has 3 bedrooms, 2 baths and a media room. Open floor plan, Living/Dining room combo with Ceramic Tile and separate Media/Family room with wood laminate flooring. Bright & Airy Master suite with wood laminate & large walk in closet. Master bath with dual sinks, instant hot water, large step in

  Claudia Montes LPT REALTY, LLC

  5610 King James Ave, Leesburg, FL 34748
• 

  /2

  $250,000

  • Land
  • 0.80 Acre
  • $312,500 per Acre

  0 Euclid Ave, Leesburg, FL 34748

  Current lot is APPROVED for 14 townhomes! under existing zoning. Vacant Lot available for sale! Zones commercial or Multifamily: Car wash, Recreational facilities, Automobile sales and more! **Per conversations with Lake County they are open to options! Don't miss this Opportunity!City of Leesburg is open and flexible if the buyer/investor wants to do any rezoning, if buyer/investor is

  Bernardo Carrasquel B EXP REALTY LLC

  0 Euclid Ave, Leesburg, FL 34748
• 

  

  /11

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1009 Loves Point Dr, Leesburg, FL 34748

  NO HOA! Beautifully Renovated Leesburg Home with New Roof.Welcome home to 1009 Loves Point in Leesburg, FL! This beautifully renovated home features a new roof, granite countertops, Shaker-style cabinets, water-resistant vinyl floors, and modern finishings. The spacious living areas are perfect for entertaining guests or relaxing in comfort. This home has ample land for RV

  Leslee Starke EXP REALTY LLC

  1009 Loves Point Dr, Leesburg, FL 34748
• 

  

  /37

  $259,900

  • 3 Beds
  • 2 Baths
  • 2,037 Sq Ft

  24801 Cranes Roost Cir, Leesburg, FL 34748

  PRICED TO SELL! This 3 Bedroom 2 Bath provides you the opportunity to move into a newly updated home and start fresh by using your creativity to make it truly your own. A brand new roof 2024. The new luxury vinyl plank flooring is waterproof and flows through the house enhancing the open floor plan. The living room and dining room merge which will allow you to use all the space to meet your life

  Aileen Indictor CENTURY 21 MYERS REALTY

  24801 Cranes Roost Cir, Leesburg, FL 34748
• 

  

  /33

  $285,000

  • 2 Beds
  • 3 Baths
  • 1,643 Sq Ft

  32525 Oak Park Dr, Leesburg, FL 34748

  HONEY STOP THE CAR!!! It's so gorgeous!! We're pleased to present the opportunity to acquire a Rare gem property in the highly demanded Pennbroke fairways at 32525 Oak Park Dr, Leesburg FL. This Golf front home has 2 bedrooms and 3 full bathrooms oversized 2 CAR GARAGE. You are going to enjoy the spacious 1,643 sqft that composes this House built in 1998. Updated in 2022 with a New roof, A/C

  Steven Koleno BEYCOME OF FLORIDA LLC

  32525 Oak Park Dr, Leesburg, FL 34748
• 

  

  /68

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft

  32676 Oak Park Dr, Leesburg, FL 34748

  HUGE PRICE IMPROVEMENT......... Brand NEW Wind Mitigation Inspection completed..... Discover the epitome of comfortable living in this splendid 3-bedroom, 2-bathroom residence spanning just over1700 sq. ft. within the esteemed Pennbrooke Fairways, an inviting gated 55+ community. The home boasts a harmonious blend of modern elegance and practicality, featuring a well-designed floor plan that

  Danny Torchia EPIQUE REALTY, INC.

  32676 Oak Park Dr, Leesburg, FL 34748
• 

  

  /14

  $267,000

  • 4 Beds
  • 2.5 Baths
  • 2,606 Sq Ft

  912 Holiday Ln, Leesburg, FL 34748

  INVESTMENT PROJECT/PROPERTY, Looking for a good return on your sweat equity? Don't miss this unique income producing opportunity. Roll up your sleeves and tackle this 4 BR 2 BA originally used as duplex. Indoor pool. City of Leesburg location near schools, medical, worship and recreation.

  Kathi Hill CENTURY 21 ALTON CLARK

  912 Holiday Ln, Leesburg, FL 34748
• 

  /2

  $212,900

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  5530 Rosewall Cir, Leesburg, FL 34748

  Charming Villa located in the highly sought-after Highland Lakes gated community of Leesburg, Florida, this well-maintained 2-bedroom, 2-bath villa offers comfort, convenience, and peace of mind with numerous recent updates. The home features an enclosed Florida room, providing additional living space and versatility. Appliance upgrades have been thoughtfully completed, including Roof (2020),

  Tracy Campoli RE/MAX FREEDOM

  5530 Rosewall Cir, Leesburg, FL 34748
• 

  /2

  $299,000

  • Land
  • 6 Acres
  • $52,091 per Acre

  6825 Silver Charm Ct, Leesburg, FL 34748

  Trade the noise for nature on this 5.74+/- acre slice of quiet Florida countryside, located on the tucked away Silver Charm Ct. Picture gentle breezes, and plenty of room to create your dream residential estate home. Whether you're envisioning a modern farmhouse, weekend getaway this property is positioned perfectly—close enough to Orlando for easy access, yet far enough to truly disconnect. Just

  Dan Tatro GRIZZARD COMMERCIAL REALESTATE

  6825 Silver Charm Ct, Leesburg, FL 34748
• 

  

  /8

  $294,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,589 Sq Ft

  9162 Harris Hawk Dr, Leesburg, FL 34788

  Welcome to The Portland at Silver Lake Pointe! This stunning property boasts 3 spacious bedrooms and 2 full bathrooms, providing plenty of room for you and your loved ones. As you step inside, you'll be greeted by an abundance of natural light that floods through the windows, creating a warm and inviting atmosphere. The heart of this home is the open-concept living area, perfect for entertaining

  

  Stanley Martin

  Builder

  9162 Harris Hawk Dr, Leesburg, FL 34788
• 

  

  /45

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  5315 Meadow Song Dr, Okahumpka, FL 34762

  Short Sale. This beautifully designed 3-bedroom, 2-bath home offering modern comfort and energy efficiency. Perfect for first-time buyers, this low-maintenance home sits in a peaceful community with no rear neighbors and a serene pond view—your private Florida retreat! Enjoy the benefits of low property taxes and energy-efficient features that help keep expenses down. Relax with your morning

  Lina Torres BROKER HUB REALTY GROUP LLC

  5315 Meadow Song Dr, Okahumpka, FL 34762
• 

  

  /14

  $262,000

  • 3 Beds
  • 2 Baths
  • 2,253 Sq Ft

  21708 Royal St Georges Ln, Leesburg, FL 34748

  Auction Property. Royal Highlands a gated 55+ active community is ready for a new owner. Royal Highlands is a golf course community with pools, tennis courts, and tons of clubs to keep you social. This home has a large Living room, Formal dining area, Eat-in Kitchen, split bedroom plan and enclosed Lania. The spacious kitchen boasts tons of storage and counter space, eat-in kitchen and

  JoAnn Bonilla MIGHTY REALTY INC

  21708 Royal St Georges Ln, Leesburg, FL 34748
• 

  

  /40

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 1,789 Sq Ft

  1208 Bonaire Dr, Leesburg, FL 34748

  Short Sale. Short Sale. ***Lender Approved Price!*** Don’t miss this rare opportunity to own a beautifully remodeled 3-bedroom plus office, 2 1⁄2-bath home on nearly half an acre, with NO HOA fees! This stunning property is perfect for anyone seeking modern style, comfort, and convenience. With a NEW roof in 2021, this home boasts a spacious and open floor plan flooded with natural light,

  Jenn Carlisle LPT REALTY, LLC

  1208 Bonaire Dr, Leesburg, FL 34748

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