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$275,000
6 Beds ⋅ 3 Baths ⋅ Leesburg SubDv. ⋅ 34748 Zip Code
ESTATE SALE — INVESTOR OPPORTUNITY, HIGHEST & BEST DEADLINE, NO CONTINGENCIES. Historic 1927 fixer-upper on 0.48 acres in the heart of Downtown Leesburg, including an additional buildable lot (1118 W line St former home site — prior impact fees paid may reduce future construction costs). 3,462 sq ft, 6 bedrooms, 3 baths, two full kitchens, large deep pool with expansive back deck. Originally used as a boarding house with separate entrances upstairs and down — incredible flexibility for renovation, multi-generational living, or income potential. Gorgeous original wood floors, soaring ceilings, rare 1927 architecture. Recent partial PVC plumbing update. Being sold by the estate, priced to sell at or above asking. Terms: Listed at $275,000. Seller requires all offers at or above asking price with NO contingencies. Buyers may inspect during the first 7 days from list date; highest and best offer due by Monday August 10, 2026. Closing required within 14 days of contract execution — earnest money due immediately upon acceptance. Sold as-is.

1116 W Line Street, Leesburg
$399,000
2 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 34705 Zip Code
Looking for your very own slice of heaven on an Oversized Lot in the heart of Central Florida's Lakeside Escape? This property is full of historical charm as it served as the town's schoolhouse, bell and all! The home features 3 Entry Ways and a Large Great Room with a Real Wood-burning Fireplace. The Kitchen, stocked with Beautiful Walnut Cabinets, provides ample space for those meaningful conversations whether you're the one preparing the meal or relaxing at the bar. The Primary Bedroom has Plenty of Storage space while the Guest Bedroom has Plenty of Privacy. Take an evening stroll around the oversized lot featuring avacado, peach, and sugar cane. You will be near enough for all your shopping and entertainment needs while far enough to experience all the peace and serenity you thought could only be found in your dreams. Come see what the buzz is all about because this home is Priced To Sell and Will Not Last Long!

13234 South Carolina Avenue, Astatula
$595,000
4 Beds ⋅ 3 Baths ⋅ Mount Dora Dickerman Sub SubDv. ⋅ 32757 Zip Code
Welcome to a truly special Mount Dora Historic District property offering timeless charm, incredible flexibility, and a proven short-term rental history. This beautifully maintained and tastefully decorated 3-bedroom, 2-bath cottage with a separate 1-bedroom, 1-bath guest house is ideally located within walking distance or a quick golf cart ride to downtown Mount Dora’s shops, restaurants, festivals, parks, waterfront, and the scenic Tremain Street walking and biking path. Zoned R-2, this exceptional property offers a unique investment opportunity in one of Mount Dora’s most desirable and walkable areas. Whether you are looking for an established short-term rental, a primary residence with additional income potential, or a flexible property that can accommodate multiple uses, this rare Historic District offering provides both lifestyle appeal and long-term value. Offered fully furnished and turnkey with acceptable offer, this exceptional property provides the opportunity to step into an established and successful short-term rental or enjoy it as your own private retreat. The possibilities are endless — rent both units, live in one cottage while renting the other for additional income, enjoy the main home while guests, family, or friends have their own private guest cottage, create a multi-generational family compound, provide a comfortable space for in-laws or adult children, or simply enjoy having a separate retreat for visitors! The main residence welcomes you with classic cottage character, including beautiful wood floors, a cozy fireplace, updated kitchen with granite countertops and stainless steel appliances, and a charming enclosed sun porch. The thoughtfully designed floor plan offers comfortable living spaces, a spacious primary suite, and an inside utility room. The 380-square-foot guest house features a kitchenette, living area, bedroom, eat in area and bathroom, offering privacy and convenience for guests, extended family, or rental opportunities. Combined with the inviting outdoor gathering areas, this property creates the perfect environment for hosting visitors while allowing everyone their own comfortable space. Enjoy a private outdoor garden oasis with mature landscaping, inviting walkways, a fenced patio area, fire pit, covered parking, and storage shed. The lovely outdoor spaces provide the perfect setting for entertaining, relaxing, and enjoying the beautiful Florida lifestyle. Located near the Tremain Street walking and biking path and just moments from downtown Mount Dora, this property captures the very best of small-town living. Whether you are looking for a full-time residence, vacation getaway, income-producing property, or a place where generations can gather while maintaining their own space, this rare R-2 zoned Historic District property delivers a lifestyle and investment opportunity unlike any other. HVAC systems 2020 and 2021, Roof 2021, hot water heater 2020.

418 E 10th Avenue, Mount Dora
$599,000
3 Beds ⋅ 2 Baths ⋅ Mount Dora SubDv. ⋅ 32757 Zip Code
A RARE opportunity to own a true piece of Mount Dora history. The David St. Clair Simpson House is a historic property dating back to the early 1900s and sits on nearly one acre in a C-2A zoned location near downtown Mount Dora. Built on what was once part of the original Simpson homestead, this property represents an important chapter in the community’s early development. Rich in history and full of potential, the property features an existing historic structure, a two-car garage, front and rear porches, and a rare underground bomb shelter! After more than a century, the home is ready for its next chapter. Whether envisioned as an ambitious restoration project or a future redevelopment opportunity, the property offers exceptional possibilities consistent with its commercial zoning and applicable City of Mount Dora and Historic District requirements. Its prominent location, generous nearly one acre parcel, and unique historical character make it an outstanding investment opportunity. Located on a corner lot near downtown shops, restaurants, parks, and year-round festivals, this is a chance to preserve a piece of Mount Dora's heritage while creating something special for the future. Buyers are encouraged to verify zoning, permitted uses, redevelopment requirements, and Historic District guidelines with the City of Mount Dora.

316 N Highland Street, Mount Dora
$549,947
4 Beds ⋅ 3 Baths ⋅ Fruitland Park SubDv. ⋅ 34731 Zip Code
Own a nationally recognized piece of Fruitland Park history on the shores of Mirror Lake. Known as Hill Crest, this distinctive residence is listed on the National Register of Historic Places and is associated with W. A. Rooks, one of the city’s founders. Historic records date the home to 1883 and note 1901 alterations that introduced Craftsman influences to its Frame Vernacular and Colonial Revival character. The two-story residence offers 4 bedrooms, 3 full baths and approximately 3,175 square feet of living space on approximately 2.70 acres. Original wood flooring extends through much of the home and up the grand staircase, while custom trim, intricate moldings, formal living and dining rooms, two wood-burning fireplaces and a spacious second-floor bonus room preserve its timeless appeal. The remodeled kitchen adds modern function with white cabinetry, stainless steel appliances, a closet pantry and a vented chimney hood. Outdoor features include Mirror Lake frontage, fenced acreage, covered parking and a detached outbuilding with flexible workshop or storage potential. Hill Crest offers a rare combination of architectural distinction, acreage, waterfront setting and everyday livability. For its next owner, Hill Crest is not simply an address. It is an opportunity to become the steward of a Florida landmark—and to write the next chapter of a story that began in the nineteenth century. Call today and Schedule your private showing and make 511 East Mirror Lake Drive your new home!

511 E Mirror Lake Drive, Fruitland Park
$499,900
3 Beds ⋅ 2 Baths ⋅ Gullera Homestead SubDv. ⋅ 32757 Zip Code
RP ZONING AND NEW ROOF! Located in the heart of Mount Dora’s Historic District, this charming 1923 cottage offers the perfect blend of vintage character and modern-day versatility. Zoned RP (Residential Professional), the property allows for residential, office, or live/work use—an exceptional opportunity in one of the city’s most desirable walkable corridors. Original features and wood floors flow throughout the home, complemented by classic built-ins and a cozy gas fireplace that add warmth and timeless historic appeal. The home features 3 bedrooms, 2 baths, and 1,383 square feet of thoughtfully arranged living space filled with natural light and authentic charm. The primary bedroom boasts a walk-in closet and an updated ensuite bathroom with a walk-in shower, while the guest bedrooms are generously sized, and the guest bathroom showcases a classic clawfoot tub. The kitchen offers abundant cabinet space and a breakfast bar, and a stand-up attic could be finished to create a loft or additional living space—the possibilities are endless! Welcoming front and back porches, historic architectural touches, a spacious 0.22-acre lot, a detached one-car garage, ample parking and a large shed complete the inviting setting, just moments from historic downtown. Whether you’re seeking a classic Mount Dora residence, a boutique office space with charm, or a flexible live/work environment, this beautiful historic cottage offers unmatched character and convenience. With RP zoning, the property’s possibilities extend beyond traditional residential use, yet it remains an ideal choice for buyers who cherish original architecture and want to live in a neighborhood known for its tree- lined streets, walkability, and small-town charm, with downtown shops, cafés, festivals, and the waterfront just steps away!! MORE PHOTOS TO COME!

1022 N Donnelly Street, Mount Dora
$135,000
1 Beds ⋅ 1 Baths ⋅ Astor Forest Campsites SubDv. ⋅ 32102 Zip Code
Perfectly proportioned, easy to manage cottage just minutes from the Springs and St. Johns River. Proven guest favorite with excellent review history. Unique, rare opportunity to purchase a piece of Old Florida lifestyle, in this beautiful historic cottage. Located in the quaint, up-and-coming town of Astor right by the Ocala National Forest, this fully furnished gem is a true boater’s dream with plenty of space to store your outdoor toys, making it an easy source of steady side income, a personal retreat, or a peaceful downsize. **Key Highlights** * High & Dry * No HOA ( optional for community boat ramp access, approx $5 per month) * Zoned mini splits for energy efficient heating and cooling * City Utilities: Connected to city water and sewer (no well or septic maintenance).High speed fibre optic internet just installed. * Prime Location: Minutes from the St. Johns River, forest trails, and famous freshwater springs in a town seeing great recent investment.

55914 Bay Road, Astor
$674,900
3 Beds ⋅ 3 Baths ⋅ Brynes SubDv. ⋅ 32757 Zip Code
COTTAGE-INSPIRED DOWNTOWN MOUNT DORA RETREAT WITH LUXURY UPDATES, EXCEPTIONAL OUTDOOR LIVING, AND UNMATCHED FLEXIBILITY! Welcome to one of downtown Mount Dora's most distinctive and beautifully renovated homes. Blending historic charm, modern luxury, and a versatile cottage-style design, this one-of-a-kind property offers the lifestyle buyers dream about when they imagine living in Mount Dora. Situated on a beautifully landscaped corner lot with no HOA, just blocks from downtown's boutiques, restaurants, cafés, waterfront parks, marina, festivals, farmers market, and entertainment district, this exceptional residence invites you to enjoy the walkable, golf cart-friendly lifestyle that has made Mount Dora one of Central Florida's most sought-after destinations. Step inside and discover a home thoughtfully transformed with attention to detail. Rich engineered hardwood flooring, abundant natural light, elegant fixtures, fresh interior and exterior paint, and a stunning wood-burning fireplace with updated hearth, surround, and mantle create warm, inviting spaces filled with character and charm. At the heart of the home is a show-stopping chef's kitchen featuring gorgeous marble countertops, an oversized center island, subway tile backsplash, stainless steel appliances, extensive cabinetry, generous prep space, and exceptional storage. Designed for both entertaining and everyday living, this space serves as the centerpiece of the home. The primary suite is a private sanctuary offering comfort and luxury. The beautifully renovated ensuite bath features marble countertops, dual vanities, a relaxing jetted garden tub, separate walk-in shower, and a spacious walk-in closet. Marble countertops continue throughout all bathrooms, providing timeless elegance throughout the home. One of the home's most desirable features is its unique cottage-inspired layout. With five separate entrances and multiple private living areas, the flexible floor plan offers exceptional versatility. A private studio-style suite with its own entrance includes a kitchenette with granite countertops, refrigerator, microwave, and range, while additional cottage-style spaces provide privacy and flexibility. Upstairs and downstairs laundry areas add convenience and functionality. Outside, the property truly comes to life. Designed to feel like a private boutique retreat, the grounds feature multiple outdoor living spaces, peaceful terraces, mature landscaping, decorative brick accents, a side deck, and a beautiful firepit courtyard perfect for gathering under the stars. The outdoor spaces offer a setting rarely found this close to downtown. Additional features include a covered carport, storage shed, new driveway and sidewalks, irrigation system, tankless natural gas water heater, two HVAC zones, and natural gas capacity for a generator, fireplace, and outdoor grill. Located near US Highway 441, SR 429, SR 414, the Florida Turnpike, Orlando, Sanford, area hospitals, airports, and Central Florida attractions, this extraordinary property combines the charm of small-town living with convenient access to everything Central Florida has to offer. Rarely does a home capture the essence of Mount Dora living so perfectly. Combining luxury finishes, cottage-inspired charm, exceptional outdoor spaces, remarkable flexibility, and an unbeatable downtown location, this is a truly special opportunity to own a one-of-a-kind Mount Dora retreat.

102 N Clayton Street, Mount Dora
$1,775,000
5 Beds ⋅ 5 Baths ⋅ Leesburg Palmora Park SubDv. ⋅ 34748 Zip Code
A rare opportunity to own one of Leesburg’s iconic lakefront estates, offering 164 feet of direct frontage on Lake Harris and set on a beautifully positioned 1.24-acre corner lot. This exceptional property delivers unmatched curb appeal with its stately presence, circular drive, mature landscaping and timeless architectural charm. The main residence spans nearly 5,000 square feet and has been thoughtfully updated to blend classic elegance with modern comfort. The 2020-renovated kitchen serves as the heart of the home, complemented by updated bathrooms throughout. Offering five bedrooms and 4.5 baths, the layout is ideal for everyday living and hosting guests. A private mother-in-law suite with its own fully equipped kitchen provides flexibility for extended family or long-term guests, while a detached efficiency apartment above the garage creates additional living space or an excellent income-producing opportunity. Designed for relaxation and recreation, the outdoor living experience is resort-style. Enjoy a recently renovated heated pool and spa, expansive patio areas, and sweeping lake views that create a backdrop for entertaining or quiet evenings at home. The private boathouse with dock and lift provides effortless access to the Harris Chain of Lakes, making this a dream setting for boating enthusiasts. Within city limits in a golf cart-friendly area, the home offers a blend of privacy and convenience, just minutes from downtown Leesburg dining, shopping and waterfront parks. With its expansive homesite, impressive 164 feet of shoreline and premier lakefront amenities, this is a one-of-a-kind offering that captures the best of Florida waterfront living.

405 Lakeshore Drive, Leesburg