Location: Leesburg
Do Not Show Listings
304 BRIGADOON CIR, LEESBURG, FL 34788
$193,000222 Days on yellowkey MLS ID: OM712733
REDUCED by $5,000 (2.5%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1278 Built: 1987Monthly Fee: $215 Tax: $1,392 (2024)Community: Scottish Highlands CondoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,392
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Best Buy in Scottish Highlands. There’s something special about a place that feels calm the moment you walk in. This charming 55+ home was designed for easy living, with gleaming hardwood floors throughout—no carpet anywhere—and sunlight streaming through and NO REAR NEIGHBORS! The high ceilings add an airy sense of space, while every room feels warm and inviting. Step out back and you’ll find your own private garden oasis. With no rear neighbors, it’s peaceful and secluded, surrounded by lush Zoysia grass that stays green thanks to a private IRRIGATION WELL. The porch is the perfect spot for morning coffee or quiet evenings. Inside, thoughtful updates make life effortless: a NEWER ROOF, HVAC, UPDATED WINDOWS and WATER HEATER, a beautiful primary suite with double closets and an updated en suite bath, plus a spacious second bedroom with a generous walk-in closet. While the home could use a few small cosmetic touches (paint) to make it truly your own, the solid structure and well-maintained systems mean the hard work is already done. The neighborhood is known for its friendliness and sense of community. You’ll be close to everything—just a mile from shopping, dining, and the post office, and a short drive to Mount Dora, The Villages, two hospitals, and the airport. Residents here enjoy resort-style amenities, including an indoor heated Olympic-sized pool, an outdoor pool, two community centers full of activities, and even a private neighborhood TV station. The affordable HOA covers basic cable, internet, and private sewer, so you can simply relax and enjoy life. This home offers the best of Florida living—beautiful weather, lively seasonal festivals, and a welcoming community that truly feels like home. Call now and arrive just in time for Winter Festivals and Activities in Lake County. Seller will consider a Lease Purchase for the right person.
Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE (800-948-0938)
Listing Agent: Valerie Foerst (352-360-3492)
33809 SILVER PINE DR, LEESBURG, FL 34788
$299,900192 Days on yellowkey MLS ID: G5105154
1 Days Off yellowkey (back on 5/20/2026)
REDUCED by $10,000 (3.2%) on 05/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1509 Built: 2000 Tax: $2,896 (2025)Community: Hidden Forest SubSingle Family
Taxes:$2,896
Tax Year: 2025
Remarks: Under contract-accepting backup offers. You will appreciate this well maintained home located on a quiet dead end street with cul-de-sac on both ends! Did I mention NO HOA? Woohoo. This is a sidewalk community, great for taking quiet afternoon strolls, riding your bike or just sitting out on your front patio enjoying the peace and quiet. This 3 bedroom, 2 bath like new home has newer water heater replaced 2025! Roof replaced in 2022! Home features include an open floor plan, tinted windows to keep those electrical cost down, split bedrooms with closet organizers, inside laundry, spacious primary bath with double sinks, walk in closet and step in shower, huge backyard is fully fenced and has a great burn pit for roasting smores on the weekend. Home Warranty included with full price offer to give you peace of mind with your purchase! The location is hard to beat. Treadway Elementary School is close by, along with everyday conveniences.
Listing is courtesy of: CENTURY 21 ALTON CLARK (352-728-2121)
Listing Agent: Betty Salas (352-516-2156)
30364 ARMENIA RD, LEESBURG, FL 34748
$275,000277 Days on yellowkey MLS ID: O6342549
REDUCED by $25,000 (8.3%) on 04/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 2022Monthly Fee: $50 Tax: $3,813 (2024)Community: Lake Denham EstatesSingle Family
Taxes:$3,813
Remarks: One or more photo(s) has been virtually staged. Short Sale. MOVE-IN READY! Modern Smart Home with Serene Preserve Views in Lake Denham Estates! This 3-bedroom, 2-bathroom turnkey home blends modern convenience with natural beauty, offering the perfect balance of comfort, style, and community. Designed with an open floor plan, this home is ideal for family gatherings and entertaining, while large windows fill the space with an abundance of natural light. The spacious, modern kitchen features custom cabinetry, ample counter space, and seamless flow into the dining and living areas, creating a warm and inviting atmosphere. The primary suite provides a peaceful escape with its private ensuite bath, while two additional bedrooms offer flexibility for family, guests, or a home office. Step outside to your backyard oasis, where serene views of the Flat Island Preserve make it feel like a private retreat, perfect for morning coffee or evening relaxation. This energy-efficient home is equipped with solar panels and smart home features, including a touchscreen panel, video doorbell, and door and window sensors for convenience and peace of mind. Located in a quiet, safe neighborhood filled with friendly neighbors, Lake Denham Estates also offers fantastic community amenities such as a pool, playground, park, and nearby trails for nature walks. Surrounded by forest views and modern conveniences, this home truly delivers the lifestyle you’ve been searching for.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Stacey Vazquez (407-874-5751)
11408 HUGGINS ST, LEESBURG, FL 34788
$180,000131 Days on yellowkey MLS ID: TB8471851
REDUCED by $3,000 (1.6%) on 04/07/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 780 Built: 1956 Tax: $1,329 (2025)Community: N/ASpa: YesSingle Family
Taxes:$1,329
Elementary School: Treadway Elem
High School: Tavares High
Middle School: Tavares Middle
Remarks: This is an incredible opportunity to own a 2-bedroom home on nearly half an acre (.46 acres) ideally located between Leesburg and Tavares—just minutes from Lake Eustis, Lake Harris, and Lake Dora. Properties with this much land, this location, and this price point are hard to find and don’t last. Step outside and enjoy the lifestyle buyers are searching for—walk to Haynes Creek Preserve and Twin Lakes Park, or relax in your fully fenced backyard complete with fruit trees, garden space, and a chicken house—perfect for those wanting space, flexibility, and a little self-sufficiency. The screened back porch adds valuable living space and features the laundry area along with a jacuzzi tub, creating a one-of-a-kind outdoor retreat. Entertain with ease thanks to the above-ground pool, large concrete patio, and a spacious garage/shed ideal for storage or a workshop. Major updates have already been taken care of, including a new roof and hot water heater (2022), termite tenting (Sept 2025), and HVAC recently serviced (Oct 2025)—giving buyers added confidence and value. Plus, fiber internet keeps you connected while enjoying peaceful surroundings. Living room ceiling being retextured 4/8/2026. With limited inventory at this price point and strong buyer demand for properties with land, this home is priced to move—schedule your showing today before it’s gone.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Gina Mcwilliams (727-677-8037)
1311 BRAEBURY DR, LEESBURG, FL 34748
$260,000123 Days on yellowkey MLS ID: O6378780
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1256 Built: 1961 Tax: $2,048 (2025)Community: Leesburg Hampton CourtSingle Family
Taxes:$2,048
Remarks: Lots of room with a view! Bring your easy chair, sit back, and relax while you enjoy the park-like, gentle water view of Lake Robinhood directly across the street from your front yard or in central air-conditioned comfort through your large living room picture window. This charming 3-bedroom, 2 full bath home with a large privacy fenced back yard has no rear neighbors and plenty of room for your toys and trailers. Some updates started. New Roof, Kitchen and floor renovated in 2022. Five minutes to restaurants, grocery stores, shopping, medical facilities, and parks. Leesburg is home to the Harris Chain of Lakes, with fantastic pleasure boating and fishing. Only one hour to most Orlando attractions and incredible ocean beaches. Don't miss this one!
Listing is courtesy of: ACRE TERRA GROUP LLC (321-368-3649)
Listing Agent: Olga Rolon (407-666-3066)
27601 STONEY BROOK DR, LEESBURG, FL 34748
$299,90037 Days on yellowkey MLS ID: G5112043
0 Days Off yellowkey (back on 5/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1490 Built: 2007Monthly Fee: $293 Tax: $3,081 (2025)Community: Legacy/Leesburg Un #7Single Family
Taxes:$3,081
Remarks: THIS IS THE ONE YOU HAVE BEEN WAITING FOR AND IT CHECKS ALL THE BOXES. GREAT KITCHEN WITH LG STAINLESS STEEL APPLIANCES, LAMINATE FLOORING, EAT IN KITCHEN, 2023 PAINTED INSIDE 2025 EXTERIOR PAINTED 2023 ROOF 2019 DOUBLE PANE WINDOWS, AND 3 BEDROOMS WITH 2 FULL BATHS. IF YOU HAVE ALWAYS WANTED OUTDOOR SPACE TO ENTERTAIN, ROOM ENOUGH FOR THE GRANDKIDS OR ENJOY WATCHING FLORIDA SUNSETS THEN LOOK NO FURTHER. ALL OF THIS IN ONE OF CENTRAL FLORIDA'S PREMIER 55+ COMMUNITIES. LEGACY OF LEESBURG. LEGACY IS A NATURE THEMED COMMUNITY WITH MILES OF WALKING TRAILS AND ACRES OF CONSERVATION. FOR THE ACTIVE ADULT THERE IS PICKLEBALL, TENNIS, BOCCE, AND A RESORT STYLE POOL. RV AND BOAT STORAGE ON SITE. COME SEE WHY SO MANY CALL LEGACY HOME.
Listing is courtesy of: DOUBLE MM DEVELOPMENT, LLC (352-552-0017)
Listing Agent: Mo Mclay (352-552-0017)
7320 MARLO RD, LEESBURG, FL 34788
$325,000117 Days on yellowkey MLS ID: G5108305
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2584 Built: 1966 Tax: $2,139 (2025)Community: NoneSingle Family
Taxes:$2,139
Remarks: Under contract-accepting backup offers. Classic Florida charm meets peaceful privacy in this spacious 3-bedroom, 3-bath home offering 2,584 square feet of flexible living space on a generous 150x150 lot just over half an acre in established Leesburg. Inside, you’ll find both a formal living room with a gas fireplace and a generous family room with its own gas fireplace, creating multiple gathering spaces for everyday living and entertaining. The kitchen flows easily into the dining room, offering a functional layout with comfortable connectivity. Significant updates provide long-term peace of mind, including a new roof on both the home and shed in 2021, attic reinsulated in 2021, and a new AC system installed in 2021. The home originally featured copper plumbing and was fully repiped in 2021 — eliminating concerns about water leaks and enhancing overall reliability. Updated bathrooms further add to the home’s comfort and value. Enjoy Florida living year-round from the large screened-in back porch overlooking a private backyard. The property includes a non-navigable canal that creates a conservation-like backdrop, and no one can build behind you — preserving natural views and enhancing the sense of seclusion. With no HOA and well and septic utilities, this property offers freedom, space, and timeless appeal in a desirable Lake County setting. Schedule your private showing today
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tania Matthews (407-497-9660)
34125 S HAINES CREEK RD, LEESBURG, FL 34788
$279,90029 Days on yellowkey MLS ID: G5111777
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1268 Built: 1952 Tax: $2,957 (2025)Community: Hilltop SubSingle Family
Taxes:$2,957
Remarks: Under contract-accepting backup offers. Beautifully remodeled 3-bedroom, 2-bath home situated on a spacious .62-acre fully fenced lot with no HOA! Located in the county just outside of Leesburg, this property offers the benefit of lower county taxes while still being conveniently close to shopping, dining, and everyday amenities. This move-in ready home features luxury vinyl plank flooring throughout, updated cabinetry, granite countertops, newer stainless steel appliances, LED lighting, and tastefully renovated bathrooms with tiled shower. The metal roof offers durability and peace of mind, while the expansive open lot provides endless possibilities for gardening, animals, outdoor entertaining, or storing your toys. Major updates include a new septic system installed last year and a new well pump replaced last month. Enjoy country-style living with modern upgrades and plenty of room to spread out!
Listing is courtesy of: EXPERT REAL ESTATE ADVISORS (352-577-5201)
Listing Agent: Eddy Workinger, Jr. (352-217-1073)
31631 BROADWATER AVE, LEESBURG, FL 34748
$339,999132 Days on yellowkey MLS ID: O6378728
REDUCED by $5,000 (1.4%) on 05/04/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 2019Monthly Fee: $42 Tax: $3,459 (2025)Community: Park Hill Ph 02Single Family
Taxes:$3,459
Elementary School: Beverly Shores Elem
High School: Leesburg High
Middle School: Oak Park Middle
Remarks: Welcome to your next chapter in one of Leesburg's most desirable residential pockets, where everyday living feels like a permanent vacation. This beautifully constructed 4-bedroom, 2-bathroom home delivers an impressive 2,140 square feet of thoughtfully designed living space that strikes the perfect balance between comfort and functionality. From the moment you step inside, the quality craftsmanship reveals itself through solid construction details and well-appointed finishes throughout. The spacious layout accommodates both everyday routines and entertaining with ease, while the generous primary bedroom offers a true retreat after long days spent exploring everything this location has to offer. And speaking of location—prepare to be spoiled. Just a stone's throw away sits the Sleepy Hollow Sports Complex, perfect for active families craving tennis, softball, or simply burning off some energy. When hunger strikes, venture over to the beloved Ski Beach Bar and Grill for waterfront dining that locals rave about. The stunning Lake Harris beckons outdoor enthusiasts with world-class boating and fishing opportunities that will have you wondering why you didn't make this move sooner. Downtown Leesburg adds another layer of charm, offering eclectic shops, delicious eateries, and that authentic Florida small-town warmth that's increasingly hard to find. The Venetian Cove Marina sits nearby for those with nautical aspirations, while UF Health Leesburg Hospital provides peace of mind just minutes away. This isn't just a house—it's a lifestyle upgrade wrapped in quality construction. Schedule your private showing today and discover why this address might just become your forever home.
Listing is courtesy of: REAL BROKER, LLC (407-922-8986)
Listing Agent: Jason Burke (352-267-7349)
33857 SKY BLOSSOM CIR, LEESBURG, FL 34788
$296,00049 Days on yellowkey MLS ID: S5148631
1 Days Off yellowkey (back on 5/19/2026)
REDUCED by $4,000 (1.3%) on 05/13/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1845 Built: 2023Monthly Fee: $104 Tax: $4,198 (2025)Community: Liberty PreserveSingle Family
Taxes:$4,198
Remarks: Under contract-accepting backup offers. A modern Construction Open-Concept 2023 home! Located in the highly desirable Liberty Preserve community. This 4-bedroom, 2-bath modern property features a bright, open floor plan with spacious living areas, perfect for family gatherings. The home boasts a modern kitchen with stainless steel appliances and a gas stove; the kitchen overlooks the family room and dining area, creating a harmonious atmosphere that blends practicality with today’s lifestyle. The Quartz Pebble White island and countertops complement the bright light from the patio doors. The patio is ideal for outdoor grilling or relaxing. A thoughtful floor plan provides privacy and comfort, with the spacious Main Suite situated at the back of the home and an attached bathroom that includes a dual-sink vanity, a generous walk-in closet, a shower, and a water closet. The three additional bedrooms are accessible from the foyer at the front of the house, offering flexibility for family, guests, or a home office. A guest bathroom with a light-colored countertop and a tub/shower combo is conveniently located between two guest bedrooms at the front of the house. The reasonably-sized laundry room is situated next to the garage. The SMART TECHNOLOGY in this home includes Remote Controlled Retractable Chandelier Ceiling Fans with Lights, different colors, and speeds in the dining and living rooms, a Ring system, a smart thermostat, and MY Q option for the garage. The 2-car garage offers convenience and extra storage if needed. If you're looking for a community with a LOW HOA fees and NO CDD fees that offers a community park, playground, open field, and a picnic area, look no further, THIS IS YOUR PLACE! The community is located near HWY 44 and HWY 441. It’s close to UF Health Leesburg Hospital, Leesburg International Airport, shopping, dining, banks, and parks such as Venetian Gardens, Lake Harris, and Lake Griffin, along with Lake Square Mall, marvel at the bird sanctuary at Venetian Gardens, Mount Dora, and The Villages.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Sonia Pires (407-308-5333)
22145 PINE GROVE LOOP, LEESBURG, FL 34748
$429,99046 Days on yellowkey MLS ID: W7885273
REDUCED by $10,000 (2.3%) on 05/19/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2850 Built: 2026Monthly Fee: $95Community: Cedar LandingsSingle Family
Taxes:$0
Elementary School: Leesburg Elementary
Tax Year: 2026
Remarks: Pre-Construction. To be built. Welcome to the Serena, where convenience meets comfort across two thoughtfully designed stories. This clever home puts the owner’s suite right where you want it – on the main level – while keeping three additional bedrooms tucked away upstairs. The heart of the home shines with 9’4 ceilings and an open layout that makes the kitchen, dining, and family areas feel like one gorgeous space. Speaking of the kitchen, it boasts a 10’6” island that’s ready for everything from breakfast rushes to holiday cookie baking. Upgrades like a wall oven and beverage center can turn this space into your culinary dream. Upstairs holds a special surprise – a bedroom that can become a second owner’s suite – hello, multi-generational living! The adaptable loft space is ready for whatever your family throws at it – from movie marathons to homework sessions. With walk-in closets in every bedroom and smart storage solution throughout, the Serena keeps clutter at bay. Best of all, the wall of windows and sliding glass doors leading to your patio (or optional lanai) bring the outdoors in, making every day feel a bit more like vacation. Introducing Cedar Landings in Leesburg, Florida! Resort-Style amenities including a zero-entry pool with cabana, a dog park with separate spaces for small and large dogs, a playground, and a 1-acre multi-use green space. 2 miles to the Florida Turnpike, 20 miles to Mt. Dora & Winter Garden, 35 miles to Downtown Orlando, 10 miles to Main Street in Leesburg with local favorite restaurants including The Brick and Barrel Public House, Turners Kitchen, & Prime 3, and 2 miles to The Monarch at Royal Highlands Golf Course. Golfers can play this course and grab burgers and brews at the club's eatery. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.
Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)
Listing Agent: Bill Maltbie (813-819-5255)
12067 CALLICARPA LN, LEESBURG, FL 34788
$310,00037 Days on yellowkey MLS ID: O6405967
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 2020Monthly Fee: $49 Tax: $3,176 (2025)Community: Meadow Rdg/Grand Island Ph 2Single Family
Taxes:$3,176
Remarks: BACK ON THE MARKET! Buyer got cold feet! This beautifully maintained 3-bedroom, 2-bath home located in the desirable Meadow Ridge at Grand Island community is BACK! Built in 2020 and kept in exceptional condition, this home offers a desirable split floor plan with spacious living areas and modern finishes throughout. Situated on a premium corner lot, the property provides added privacy and curb appeal. Enjoy peace of mind with a recently serviced septic system and the benefit of a low HOA. Move-in ready and conveniently located near shopping, dining, and major roadways, this home is a must see!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Janet Lynn (407-314-6198)
262 VERNY GROVE LANE, LEESBURG, FL 34748
$320,000168 Days on yellowkey MLS ID: O6369544
5 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1780 Built: 2025Monthly Fee: $18 Tax: $253 (2025)Community: Arbor ParkSpa: NoSingle Family
Taxes:$253
Elementary School: Fruitland Park Elem
Middle School: Carver Middle
Remarks: Under contract-accepting backup offers. New Price Drop of $5400.00, combined with either $12,000. in Flex Funds or a 4.99 interest with one of our Preferred Lenders makes this a Sweet Deal! Welcome home to this brand-new, move-in-ready 3-bedroom, 2-bath home located in the beautiful Arbor Park community. Designed with everyday comfort and easy entertaining in mind, this home features an open-concept layout that brings everyone together while still offering private, relaxing spaces. The upgraded kitchen is the heart of the home, showcasing stunning granite countertops throughout, a large center island, and sleek Whirlpool stainless-steel appliances—perfect for cooking, hosting, and casual gatherings. A spacious laundry room adds extra convenience and storage, making daily routines a breeze. Both bathrooms are generously sized and finished with elegant granite, creating calm, spa-like retreats. For added peace of mind, your new home includes a 1-year builder warranty along with a 10-year structural warranty. Arbor Park offers a wonderful blend of comfort and lifestyle, with planned community amenities including a beautiful pool with cabanas. Best of all, this community features a small CDD fee and a very low HOA, making it an exceptional value for homeowners. If you’re looking for a move-in-ready home in a welcoming community with modern finishes and future amenities, this Arbor Park home checks all the boxes.
Listing is courtesy of: ADAMS HOMES REALTY, INC (850-469-0977)
Listing Agent: Michael Soto (689-294-0148)
2710 LORRAINE DR, LEESBURG, FL 34748
$244,90026 Days on yellowkey MLS ID: O6407819
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1989Monthly Fee: $11 Tax: $2,833 (2025)Community: Leesburg Westside OaksSpa: NoSingle Family
Taxes:$2,833
Remarks: This move-in ready three-bedroom, two-bathroom home is located in the charming Leesburg Westside Oaks neighborhood. The interior features a functional layout highlighted by an updated kitchen. This stylish cooking space is complete with modern granite countertops and sleek stainless steel appliances. The residence offers a comfortable living environment designed to accommodate a variety of lifestyles. The exterior includes a private, fully fenced backyard, providing a secure space for outdoor entertaining or pets. Situated in a prime location, this home is just a short drive from local schools, shopping centers, restaurants, and hospitals. Schedule your private showing today
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
4331 MAGNOLIA AVE, LEESBURG, FL 34748
$299,90026 Days on yellowkey MLS ID: L4961818
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1396 Built: 1960 Tax: $1,441 (2025)Community: UnincorporatedSingle Family
Taxes:$1,441
Remarks: Fractional Ownership. Step into timeless Florida charm with this beautifull 1960-built waterfront home featuring 2 bedrooms, 2 bathrooms, and a dedicated office space. Nestled on a peaceful freshwater canal with direct access to the renowned Lake Harris Chain of Lakes, this property blends historic character with an unbeatable outdoor lifestyle. From the moment you arrive, you’ll appreciate the home’s classic charm, warm character, and inviting atmosphere that newer homes simply can’t replicate. Spend your days bass fishing from your backyard or enjoying endless waterfront activities including water skiing, jet skiing, paddle boarding, canoeing, and kayaking. Whether you’re searching for a full-time residence, weekend retreat, or waterfront getaway, this unique home offers vintage charm, scenic beauty, and true Florida living at its finest
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Skip Scism, Ii (863-608-4356)
5106 CHANTICLEER DR, LEESBURG, FL 34748
$535,00026 Days on yellowkey MLS ID: G5112349
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3112 Built: 2006Monthly Fee: $180 Tax: $4,549 (2025)Community: Plantation At Leesburg Chanticleer Village LSingle Family
Taxes:$4,549
Remarks: Welcome to 5106 Chanticleer Dr, a rare and extensively expanded custom home located in the highly sought-after Plantation at Leesburg, one of Central Florida’s premier 55+ gated golf communities. Offering 3 bedrooms, 2.5 baths, a versatile flex room, and an impressive 3,112 square feet of living space, this thoughtfully designed residence combines spacious living, quality upgrades, and exceptional functionality rarely found in the community. From the moment you enter, you’ll appreciate the soaring ceilings, elegant archways, abundant natural light, and oversized living spaces that create an open yet inviting feel throughout the home. The expansive layout offers multiple entertaining and gathering areas, while the split-bedroom floor plan provides privacy and flexibility for guests or multigenerational living. The flex room is ideal for a home office, hobby space, library, or additional guest accommodations. The kitchen is both spacious and functional, featuring upgraded appliances, abundant cabinetry, generous counter space, and a large center island perfect for cooking and entertaining. The adjacent living areas flow seamlessly to the oversized rear porch through beautiful French doors, creating the ideal indoor-outdoor Florida lifestyle. Extensive structural upgrades set this home apart, including a garage expansion with an additional 6’ on the right side and 4’ to the front, a 4’ bedroom extension, a fully enclosed 16’x10’ room off the left-side patio with windows, and a massive 30’x10’ rear porch ideal for relaxing or entertaining. Additional custom storage spaces include a 10’x10’ closet with window in the flex room and another 12’x10’ closet in the rear guest room. The primary suite features upgraded luxury vinyl plank flooring and its own dedicated HVAC system for enhanced comfort and efficiency. Major mechanical updates include a new roof (2021), HVAC system (2021), and hot water heater (2020). The home also features an upgraded oversized gutter and downspout system engineered to meet FBC2001 wind load standards for added durability and peace of mind. Residents of Plantation at Leesburg enjoy resort-style amenities including two 18-hole championship golf courses, three clubhouses, three heated pools, fitness centers, tennis and pickleball courts, walking trails, fishing lakes, an on-site restaurant, and countless clubs and social activities. Conveniently located near shopping, dining, medical facilities, and the Florida Turnpike, this one-of-a-kind property offers the perfect blend of comfort, flexibility, and active Florida living.
Listing is courtesy of: CENTURY 21 MYERS ROSE REALTY (352-717-2000)
Listing Agent: Mary Jane Grimes (410-353-0795)
5028 ST. ANDREWS, LEESBURG, FL 34748
$295,00096 Days on yellowkey MLS ID: G5109308
0 Days Off yellowkey (back on 4/17/2026)
REDUCED by $10,000 (3.3%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 2002Monthly Fee: $229 Tax: $4,257 (2025)Community: Royal HighlandsSpa: NoSingle Family
Taxes:$4,257
Remarks: Beautiful turnkey furnished open floor plan 3/2 Expanded Custom Emerald Model (1,680 sq.ft.) built in 2002 and located on the golf course in 55+ Royal Highlands gated community. NEW ROOF IN 2025, NEW HVAC IN 2024 AND WINDOW WORLD THERMAL WINDOWS IN 2010. The updated eat-in kitchen is open to the great room and features stainless steel appliances, 42” upgraded cabinets with pull out drawers and attractive crown molding, Corian countertops, built-in desk, pantry, recessed lighting and 19” ceramic tile flooring. The primary bedroom suite offers a spacious walk-in closet, comfort height Corian dual sink vanity, shower enclosure with seat, and a lovely ceramic tile floor. Both guest bedrooms have built-in wall units and Murphy beds. The adjacent guest bath offers a dual sink vanity, bathtub and a linen closet. The convenient inside laundry room includes a washer, dryer and shelving. Sliding doors in the great room lead to an enclosed 9x17 screened lanai with sliding acrylic windows and a SunSetter motorized retractable awning. There is an adjoining cement patio where you and your friends can BBQ and enjoy your lovely backyard view. Additional features to this well-designed home include a two-car garage with sliding screen door, vaulted ceiling in the great room, ceiling fans, pocket doors, irrigation system, cement curbing on flower beds, pull-down stairs in the garage for easy access to the attic, a Kinetico water softener and the home is wired for a generator. All appliances are included and the Termite Bond is transferable to buyers. Royal Highlands is located within easy access to the FL Turnpike. Situated on 1,092 acres of land this expertly planned resident owned community of 1500 homes boasts approximately 35 percent conservation land. This natural preserve is the habitat of waterfowl, native birds, and other wildlife. In addition there are 4 lakes, rolling hills with panoramic views, and an 18-hole Golf Course and restaurant, all adding to Royal Highlands' expansive feel. There are many amenities to offer homeowners including an outdoor pool and a heated indoor pool as well as over 100 clubs and common interest groups to choose from. Royal Highlands has four pickleball courts. Royal Highlands is in close proximity to the Orlando Airport and the attractions. The new Orlando Health South Lake Hospital Emergency Room and Medical Pavilion is located nearby on Hwy.27 north.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-394-5900)
Listing Agent: Doug Duvarney (352-255-3236)
32914 CROOKED OAKS LN, LEESBURG, FL 34748
$269,90044 Days on yellowkey MLS ID: G5109347
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1745 Built: 1999Monthly Fee: $265 Tax: $1,836 (2025)Community: Pennbrooke Ph 01K Units 01 & 02Single Family
Taxes:$1,836
Remarks: Spacious MacLean II model with 3 bedrooms/2 baths. It features an open kitchen with oak cabinets and both breakfast nook and separate dining room. Notice the charming leaded glass insert in front door. It has laminate flooring in all but kitchen and laundry, which has cabinets and a freezer which will convey. It has newer double pane windows, the roof was replaced in 2017, and HVAC in 2024. The remaining furniture can convey or be removed prior to closing. There is a 2 car garage with sliding screen doors. It needs a little updating but is priced to sell quickly. This property is in Pennbrooke Fairways, an active 55 plus community located close to The Villages Community and many of their amenities. Pennbrooke has three golf courses--two executive and one regulation. Also tennis, pickleball, two pools with hot tubs, free fitness center, two recreation centers, a restaurant, library, and hair salon. Many activities and classes are offered. If you're not familiar with Pennbrooke, you need to check it out!
Listing is courtesy of: SALLY LOVE REAL ESTATE (352-399-2010)
Listing Agent: Carol Julianelli (352-516-9659)
35724 DAWN DR, LEESBURG, FL 34788
$268,00043 Days on yellowkey MLS ID: O6404214
INCREASED by $38,000 (16.5%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1986 Tax: $2,235 (2025)Community: Haines Creek HeightsSingle Family
Taxes:$2,235
Remarks: One or more photo(s) has been virtually staged. Short Sale. THE PERFECT START OR A SAVVY ADDITION WITH OUTDOOR FREEDOM! This move-in-ready 3BR/2BA home offers the ultimate blend of interior peace of mind and incredible outdoor potential. Tucked away at the very end of a quiet dead-end street, the property sits on a spacious lot that provides exceptional privacy and plenty of room to build your dream backyard oasis, park your toys, or entertain. Major recent interior and structural updates—including a newer roof and a newer AC system—mean you won't have to spend a dime on immediate capital expenses, saving you thousands and ensuring easier insurance options. Enjoy a low-maintenance lifestyle with durable tile and laminate flooring throughout—absolutely NO carpet to worry about after a day spending time outside! Best of all, with NO HOA restrictions, you have the absolute freedom to truly make this expansive outdoor space your own—bring your boat, your RV, or your utility trailers while keeping your monthly carrying costs at a zero-dollar minimum. Whether you’re looking for your first "Home Sweet Home" with room to grow or a lucrative, high-demand rental with great curb appeal, this solid 1986 build is ready for its next chapter. Easy to show and priced to sell—schedule your tour today!
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Elieser Mercado, Jr (321-888-6328)
9531 MID SUMMER LN, LEESBURG, FL 34788
$669,000172 Days on yellowkey MLS ID: G5105863
REDUCED by $6,000 (0.9%) on 05/18/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2972 Built: 2025 Tax: $1,001 (2025)Community: Silver Lake Meadows SubSingle Family
Taxes:$1,001
Remarks: One or more photo(s) has been virtually staged. Brand new, spacious, and impeccably designed—this contemporary 4-bedroom, 3-bath custom home is tucked away on a quiet cul-de-sac in a gated enclave on the highly sought-after north side of Silver Lake, with NO HOA restrictions. Why wait months to build when you can move right in and enjoy nearly 3,000 sq. ft. of thoughtfully designed living space on over half an acre, surrounded by other beautiful custom homes? From the moment you enter, the grand foyer sets the tone with soaring ceilings, tray details, and an open, light-filled layout. The living room, dining area, and gourmet kitchen flow seamlessly together, creating the perfect space for both everyday living and entertaining. High-end wood-look tile runs throughout the home, complemented by tall doors and ceilings that enhance the modern, upscale feel. The chef’s kitchen is a showstopper, featuring premium quartz countertops (carried through all bathrooms), soft-close cabinetry, a range top with vented hood, double ovens, and abundant workspace—ideal for hosting and culinary enthusiasts alike. Just off the main living area, the oversized covered back porch overlooks a massive backyard that is partially fenced and ready for a pool, playground, or outdoor oasis. The split-bedroom floor plan offers exceptional privacy and flexibility. The expansive primary suite features a spa-like bath with double vanities, a walk-in shower, soaking tub, and a massive walk-in closet with custom built-ins and organizers. A secondary bedroom includes its own private en-suite bath—perfect for in-laws or guests. The two additional bedrooms are oversized by today’s standards, each with a walk-in closet, and are separated by a third full bath with double vanities and a tub/shower. Additional highlights include a well-appointed laundry room with a convenient dog-washing station, a long pavered driveway ideal for multiple vehicles when entertaining, and a peaceful setting that still offers quick access to shopping, dining, hospitals, and everyday conveniences. This is a rare opportunity to own a truly turnkey, high-end home in one of Leesburg’s most desirable areas—without HOA limitations. If you’re looking for the premier place to plant your roots, look no further. Schedule your private showing today before this exceptional home is gone. *Aerial photo property lines are approximate and to be verified by buyer.
Listing Agent: Brandie Mathison-Klein (407-488-3446)
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