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$2,590,000
7 Beds ⋅ 8 Baths ⋅ Alisa SubDv. ⋅ 32801 Zip Code
One of Orlando’s signature homes in the Cherokee Historic District, this extraordinary estate exudes elegance and timeless grandeur, offering a resort-style pool, private guest house and expansive grounds in one of downtown’s most coveted neighborhoods. Set on an oversized lot (.56 acres), this stately three-story, 18-room residence offers an impressive blend of scale, craftsmanship and thoughtful updates. A dramatic oval, handcrafted three-story staircase creates a striking first impression in the grand black-and-white marble foyer, flanked by formal living and family rooms designed for both elegant entertaining and comfortable living. The living room extends into a light-filled sunroom, ideal as a private office or studio, while the family room opens to a screened porch with slate flooring, seamlessly connecting indoor and outdoor spaces. The chef’s kitchen is both functional and refined, featuring an oversized island, Wolf convection gas range, Sub-Zero refrigeration with additional drawer units, custom cabinetry, and purified drinking water. Overlooking the beautifully refinished pool and outdoor entertaining areas, the kitchen flows effortlessly into a well-appointed summer kitchen, perfect for hosting. Interior details reflect exceptional character and craftsmanship, including wood flooring throughout most of the home, decorative ceiling elements, picture rails, brass antique light switches, and a wood-burning fireplace. The spacious primary suite features soaring ceilings and a large bath with an oversized shower and distinctive metal sinks. A secondary staircase and basement level-with updated laundry, dual washers, drying area, and laundry chute-add both charm and functionality. Extensive recent improvements totalling over $200,000 enhance both beauty and peace of mind, including a new slate roof (2024), copper gutters and soffits, updated flat roofs, new insulation, upgraded electrical and multiple HVAC systems, along with a tankless water heater for the main house and separate for the guest house. The outdoor setting is equally impressive, with mature landscaping, a motor court, two-car garage, and a private one-bedroom guest house complete with full kitchen and bath. Additional features include Tesla charging capability and a prepaid termite bond. Ideally located just minutes from downtown Orlando, within walking distance Restaurants, Farmers market, Arts festivals, Dr. Phillips Center for the Performing Arts and less than a mile from Orlando Health ORMC, the home offers both convenience and prestige. Originally built for Dr. and Mrs. John S. McEwan, among early Orlando’s most prominent families and featured on the cover of Orlando Magazine in 1923, this residence is a rare legacy property, thoughtfully maintained and updated to meet the standards of today’s most discerning buyer while preserving its rich architectural heritage. Furnishings may convey with acceptable contract. Home has been pre-inspected.

705 Delaney Avenue, Orlando
$2,290,000
6 Beds ⋅ 5 Baths ⋅ Wilmott J W Rev SubDv. ⋅ 32801 Zip Code
Completed in 2024, this exceptional custom residence by M. Lahr Homes, thoughtfully designed by Willow Tree Partners, blends timeless architecture with modern luxury across 4,105 square feet of beautifully curated living space. Offering six bedrooms, five baths and a tandem three-car garage, every detail has been meticulously crafted for elevated everyday living and effortless entertaining. Perfectly positioned just minutes from Downtown Orlando, you'll enjoy easy access to Michelin-recommended restaurants, charming local boutiques, neighborhood coffee shops, vibrant parks, cultural venues and year-round events, bringing the very best of city living to your doorstep while offering the privacy and comfort of a custom luxury home. Inside, the open-concept floor plan showcases soaring ceilings, custom millwork, designer lighting, solid-core 8-foot doors and expansive PGT impact-rated windows that flood the home with natural light. At the heart of the home is a chef's kitchen featuring premium Thermador appliances, a stunning crystallized quartzite waterfall island, custom cabinetry, a walk-in pantry and an adjoining beverage center. The primary suite is a true spa-inspired retreat with luxurious finishes, custom cabinetry and a beautifully appointed bath. Throughout the home, curated stone surfaces, porcelain tile, custom built-ins and exceptional craftsmanship create a refined yet welcoming atmosphere. Outdoor living rivals a private resort with a heated saltwater pool and spa, a fully equipped summer kitchen, a covered lanai, custom landscaping and architectural cypress ceilings designed for year-round enjoyment. Modern convenience is seamlessly integrated with whole-home audio, professional-grade Wi-Fi, security and surveillance systems, hardwired motorized shades and extensive pre-wiring for future expansion. Built with quality and efficiency in mind, the home also features spray foam insulation, dual Carrier HVAC systems, natural gas service, a tankless water heater and premium construction finishes throughout. This is a rare opportunity to own a truly turnkey custom luxury residence where exceptional design, craftsmanship, technology and an unbeatable Downtown Orlando lifestyle come together. An extensive list of luxury features and upgrades is available in the attached supplemental documents.

809 E Church Street, Orlando
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Edgewater Terrace SubDv. ⋅ 32801 Zip Code
Price Improvement! Welcome home to one of Thornton Park’s most distinctive private compounds, where expansive outdoor living spaces and thoughtful design create the perfect backdrop for everyday living and unforgettable entertaining. This exceptional 4-bedroom, 4.5-bath residence offers the rare opportunity to enjoy the charm of classic front-porch living paired with the energy and convenience of Downtown Orlando. The moment you arrive, you're greeted by lush landscaping, a tranquil fountain, and an inviting 35-foot-wide covered front porch illuminated by designer gas lanterns. Whether you're enjoying your morning coffee, visiting with neighbors, or unwinding after a long day, this incredible front porch becomes a true extension of the home and sets the tone for the warm, welcoming atmosphere found throughout. Inside, the 3,528-square-foot main residence features soaring ceilings, abundant natural light, newly refinished oak hardwood floors, and an open-concept layout designed for both comfortable daily living and effortless entertaining. The chef’s island kitchen flows seamlessly into the spacious great room with its dramatic fireplace, custom wine display, and flexible bonus space perfect for a home office, media room, or quiet retreat. Upstairs, the private primary suite offers a peaceful escape complete with a spa-inspired bath, custom walk-in closet, and its own balcony overlooking the property. Two additional oversized bedroom suites provide exceptional comfort and privacy for family and guests. Outdoor living truly takes center stage. The oversized covered back porch overlooks a beautifully landscaped and newly fenced backyard, creating the perfect setting for weekend gatherings, al fresco dining, or relaxing under the glow of the custom landscape lighting. And then there’s the showstopper—a spectacular rooftop deck spanning nearly the entire footprint of the main house. With panoramic views of the Downtown Orlando skyline, this incredible space is ideal for sunset cocktails, entertaining under the stars, yoga at sunrise, or simply enjoying front-row seats to the city lights and seasonal fireworks. Adding even more versatility is the detached, air-conditioned three-car garage with Pebble Tech flooring and EV charging, topped by a beautifully appointed 726-square-foot guest residence complete with 1 bedroom, 1 bath, full kitchen, washer and dryer, and private balcony—perfect for guests, multigenerational living, a private office, or income-producing opportunities. Recent upgrades include 27 new Renewal by Andersen custom windows, three brand-new HVAC systems and condensers, all-new fencing, fresh interior and exterior paint, refinished hardwood floors, custom drapery and motorized shades, a new KitchenAid refrigerator, washer and dryer, integrated security system and cameras, plus extensive landscaping and architectural lighting enhancements throughout the property, including the rooftop deck. Perfectly positioned in the heart of the highly walkable Thornton Park District, you'll be just blocks from Lake Eola and Downtown Orlando’s acclaimed dining, entertainment, arts, and sports venues, while still enjoying the privacy and tranquility of this truly one-of-a-kind urban retreat.

119 N Hyer Avenue, Orlando
$1,679,996
4 Beds ⋅ 5 Baths ⋅ Lawsona Park SubDv. ⋅ 32801 Zip Code
One or more photo(s) has been virtually staged. Meticulously renovated over two years, this residence reflects more than $875,600 in improvements and was independently appraised above the current asking price on July 2, 2026. Located in the coveted Lake Lawsona Historic District in the heart of downtown Orlando, this extraordinary 1920s estate sits on an oversized double lot with dual street access and features a completely reimagined saltwater pool, among the largest in the area, along with a private studio apartment (ADU) with its own entrance, full kitchen, and bath. Just blocks from acclaimed dining, boutique shops, parks, cultural venues, and entertainment, this distinguished historic residence is surrounded by majestic live oaks and offers a rare combination of privacy, outdoor living, and urban convenience. Inspired by the timeless architectural principles of Andrea Palladio, the home harmoniously blends historic character with modern luxury and exceptional craftsmanship. The property offers a 3-bedroom, 3.5-bath main residence with a private office, spacious laundry room, and an independent ADU ideal for guests, multigenerational living, a home office, or income-producing potential. Nearly every major system has been upgraded or replaced, including the 50-year concrete tile roof (2019), Pella windows, complete plumbing and drain systems, gas tankless water heater, electrical system and panel, dual HVAC systems, ductwork, and insulation (2024–2025). The rebuilt carport includes a new engineered foundation designed to support the expanded primary suite above, featuring its spa-like bath and custom walk-in closet. The expansive double lot provides exceptional privacy and future possibilities, while the completely reimagined saltwater pool retreat is surrounded by elegant white travertine decking and complemented by a covered lanai with motorized screens, creating a private resort-style experience rarely found in an urban setting. The thoughtfully designed interior features soaring ceilings, elegant living spaces, a formal dining room, and a chef’s kitchen with custom cabinetry, oversized island, premium Dacor double ovens, and gas cooktop. The primary suite includes a spa-inspired bath with a freestanding bathtub and expansive custom walk-in closet, while additional bedrooms offer comfort and privacy. Minutes from Lake Eola, Thornton Park, the Dr. Phillips Center for the Performing Arts, Winter Park, Park Avenue, Michelin-recognized dining, Orlando Health, and AdventHealth, this extraordinary residence offers a rare opportunity to own a fully reimagined historic estate in the center of Orlando’s most desirable urban lifestyle.

1408 E Church Street, Orlando
$1,225,000
8 Beds ⋅ 5 Baths ⋅ Lake Davis Heights SubDv. ⋅ 32801 Zip Code
4-UNIT INCOME PROPERTY • ~$108K+ ANNUAL GROSS RENT • NEAR DOWNTOWN ORLANDO • MINUTES FROM LAKE EOLA • 3 UNITS 2023 NEW CONSTRUCTION W/ FIRE SPRINKLERS • FRONT HOUSE RENOVATED 2018 • 4BR/2BA, 2BR/1BA, 2BR/1BA & STUDIO • 4X IN-UNIT LAUNDRY • 5 PRIVATE PARKING SPACES • NO HOA A rare multi-family home and exceptional quadplex investment opportunity located in Downtown Orlando's highly sought-after Lake Davis-Greenwood neighborhood. This turnkey multiplex combines one fully renovated historic home with a triplex featuring three new apartments on a single parcel, offering an ideal opportunity for investors, owner-occupants, or those seeking a multi-generational living arrangement. Encompassing approximately 3,658 square feet, this quadraplex includes four income-producing units with eight bedrooms, five bathrooms, and one separately metered one-car garage accessed from the exterior. Tenants enjoy four private parking spaces plus guest parking off Catherine Street. Each residence features its own private washer and dryer, creating a highly desirable, low-maintenance rental property designed to support premium rents. The property typically generates approximately $9,000 per month in gross rental income (approximately $108,000 annually), with a diversified unit mix that provides multiple income streams and strong rental demand. The front residence, originally built in 1950 and extensively renovated in 2018, offers three bedrooms, two bathrooms, and a flexible bonus room ideal for a home office, playroom, or guest suite. Additional features include a natural gas range, an on-demand gas water heater, a gas dryer, a spacious primary bedroom, and a walk-in closet. Behind the main home is a newly constructed building, completed in 2023, featuring three separate apartments with individual addresses (Units A, B, and C). The rear building includes a downstairs two-bedroom, one-bath apartment with a private fenced backyard, an upstairs two-bedroom, one-bath apartment with soaring 12-foot ceilings, and an upstairs studio apartment, all finished with contemporary materials and designed for low-maintenance ownership. Whether you're searching for a high-performing multi-family home, an investment quadplex, a multiplex with excellent income potential, or a property suited for multi-generational living, this offering provides exceptional flexibility. Live in one unit while generating rental income from the others, or lease all four units for immediate cash flow and long-term appreciation. Located within walking distance of 903 Mills Market, Lake Davis, Greenwood Urban Park, Delaney Park, and Thornton Park, the property also offers convenient access to Orlando Health, the Dr. Phillips Center for the Performing Arts, the Kia Center, Inter&Co Stadium (Orlando City Soccer), and Downtown Orlando's premier dining, entertainment, and employment centers.

1505 Catherine Street, Orlando
$798,000
4 Beds ⋅ 4 Baths ⋅ Bailey Heights SubDv. ⋅ 32801 Zip Code
This beautiful FULL duplex (BOTH SIDES)is located in the highly desirable Lake Eola Heights Historic District, just minutes from downtown. The property has been completely renovated, offering modern updates while maintaining its classic charm. Each unit features a brand-new kitchen and updated bathrooms, along with two spacious bedrooms and 1.5 renovated baths on each side. The refinished hardwood floors and staircase add warmth and character throughout the home. Major upgrades include a new roof installed in September 2025, along with fresh interior and exterior paint for a crisp, move-in ready fe The exterior offers a beautiful fenced yard with elegant paver walkways and driveways, creating a welcoming outdoor space for residents and guests. This is a rare opportunity to own a fully updated duplex in one of Orlando’s most charming historic neighborhoods. This perfect for investors or owner-occupants seeking rental income. Lease Purchase option as well as possible owner financing available, call Listing agent for details

608 Highland Avenue, Orlando
$725,000
4 Beds ⋅ 3 Baths ⋅ Thornton Park Add SubDv. ⋅ 32801 Zip Code
Virtually Staged. **THORNTON PARK TREASURE** Built in 1929 and nestled in Orlando's coveted Historic Thornton Park District, this beautifully restored bungalow is your chance to own a piece of the city's architectural history. Every effort has been made to preserve the home's original details, from restored rope-and-weight windows and original hardwood floors to its period-correct millwork and charming fireplace, preserving the authentic character and craftsmanship that make this home truly special. The property includes a detached guest house (ADU), offering a total of 4 bedrooms and 2.5 bathrooms. Complete with its own bedroom, full bath, kitchenette, and laundry area, the guest house provides exceptional flexibility for extended family, guests, a private home office, studio, or fitness space. Lovingly maintained and thoughtfully refreshed, the home has undergone extensive maintenance and improvements while preserving its historic integrity. Recent upgrades provide peace of mind and include an electrical rewire with two new electrical panels (2021), tankless water heater (2022), a BRAND-NEW ROOF to be installed prior to closing, and a new washer and gas dryer (2024). Unwind on the front porch, entertain on the private backyard deck, and enjoy one of Orlando's most walkable neighborhoods. Just a short stroll to Lake Lawsona Park, Thornton Park's acclaimed restaurants, boutique shopping, Lake Eola, neighborhood parks, and Downtown Orlando, this one-of-a-kind historic home offers an exceptional lifestyle where history, craftsmanship, and modern convenience come together.

12 N Thornton Avenue, Orlando
$699,000
4 Beds ⋅ 3 Baths ⋅ Lake Lawsona Place SubDv. ⋅ 32801 Zip Code
Virtually Staged. HUGE PRICE REDUCTION! LAST CHANCE ON THIS BEAUTIFUL DOWNTOWN HOME, AS THE SELLER WILL PULL THE LISTING IN 30 DAYS IF NOT SOLD AND LEASE IT. PROPERTY FOR SALE OR LEASE – SHOWINGS BY APPOINTMENT ONLY Rare opportunity to own or lease a beautifully remodeled modern home in a historic home district in the heart of Thornton Park with stunning lake views of Lake Lawsona. Homes like this rarely become available — especially with a FULL 2-CAR GARAGE, a feature that is almost impossible to find. This modern home is located in Downtown Orlando’s historic districts. You can also watch the Space Shuttles launch from your porch with an unimpeded view of the eastern sky! Located in one of Orlando’s most desirable and truly walkable neighborhoods, this home places you just minutes from Lake Eola, the famous Sunday Farmers Market (Live Music and Food), award-winning restaurants, coffee shops, wine bars, nightlife, downtown events, the Kia Center, and the Dr. Phillips Center. This is one of the very few locations in Central Florida where you can genuinely enjoy an upscale lifestyle without needing a car for most daily errands, dining, entertainment, and social outings. This large modern home built in (1998) is located in the historic home district blends timeless character with modern upgrades and flexibility. Recently remodeled, the property offers the charm of historic downtown scenery while providing modern updated finishes and conveniences that are difficult to find in the area. The oversized layout, rare 2 car garage, premium location, and incredible Lake Lawsona water views make this a truly unique offering. There is a 0.6 mile sidewalk walking / jogging path just outside the property that circle Lake Lawsona park area. Ideal for a primary residence, executive housing, seasonal home, luxury rental, or investment opportunity. Potential Airbnb or corporate housing use may be possible subject to local regulations. CALL FOR LEASING OPTIONS: Available furnished for an additional fee. Flexible lease terms may be considered, including shorter furnished stays with minimum term requirements. Long-term lease discounts available. Lease-to-purchase may be considered with substantial down payment and acceptable terms. Opportunities like this in Thornton Park are exceptionally rare — especially a remodeled historic home with this size, this location, lake views, and a true 2-car garage. LEASE REQUIREMENTS: Starting at $5500 / Month Background check, credit/income verification, and references required for tenants. Pets negotiable. OWNER IS A LICENSED REAL ESTATE PROFESSIONAL

148 S Thornton Avenue, Orlando
$499,900
4 Beds ⋅ 4 Baths ⋅ Douglass Sub SubDv. ⋅ 32801 Zip Code
Investor opportunity in Orlando’s desirable Lake Cherokee Historic District, minutes from Downtown Orlando. This 1920s duplex offers two income-producing units, each historically renting for approximately $1,800–$2,000 per month. Renovate and reposition the existing duplex, occupy one unit while leasing the other, explore conversion to a single-family residence, or evaluate potential redevelopment options. The property needs renovation but offers significant potential through its location, flexible configuration and established rental history.

522 S Osceola Avenue, Orlando
$499,900
4 Beds ⋅ 4 Baths ⋅ Lake Cherokee Historic District SubDv. ⋅ 32801 Zip Code
Opportunity awaits in Orlando’s Lake Cherokee Historic District! This 1920s duplex offers flexibility for an owner-occupant seeking to live in one unit while renting the other, an investor, a multigenerational household, or a buyer interested in converting it back into a single-family home. Each side has historically rented for approximately $1,800–$2,000 per month. The property needs renovation and is ideal for buyers who recognize the potential of its location, layout and historic character. Conveniently located near Downtown Orlando, Lake Cherokee Park, dining, entertainment and major roadways. Bring your vision and contractor to restore this unique property.

522 S Osceola Avenue, Orlando