Location: Orlando , 32801
Do Not Show Listings
300 E SOUTH ST #6004, ORLANDO, FL 32801
$187,00034 Days on yellowkey MLS ID: S5144812
Bed: 1 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 744 Built: 2002Monthly Fee: $530 Tax: $3,124 (2025)Community: Grande Downtown OrlandoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,124
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Location, location, ...Charming one bedroom one bath on top 6th floor with Balcony overlooking the courtyard. Laminated flooring in Living and Dining, Split bedroom plan, Full size washer/dryer hookup. The Grande Downtown is a gated condominium community close to Thornton Park, Sun Rail, major highways, Orlando’s top attractions and the Dr. Phillips Center for the Performing Arts—including the new Judson’s Live Jazz Bar, Lake Eola, a dog park just down the street off Jackson, restaurants, boutique shopping and stores, so many cultural, social, and sports activities at your doorstep to enjoy. The entire community has undergone Recent exterior renovations (2020-21) including the installation of new windows, roofing, and fresh paint to ensure that the Owners will benefit for years to come. The unit is located on a quiet side, with a garden view, and 2 parking spots. The HOA includes water, sewer, trash pickup, pest control, exterior maintenance, and nighttime security, giving you peace of mind, 24-hour gym, grilling areas, secured access, and onsite management. Perfect home for owner-occupants, first-time buyers, or investors who value location, convenience, and beautiful downtown lifestyle.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Gloria Mejia (407-207-2220)
1455 CATHERINE ST, ORLANDO, FL 32801
$1,350,000Listed 04/03/2026 4:05PM MLS ID: O6396233
Bed: 6 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 3884 Built: 2008 Tax: $20,081 (2025)Community: Lake Davis HeightsSingle Family
Taxes:$20,081
Remarks: Welcome to 1455/1459 Catherine St — a rare opportunity to own a beautifully maintained duplex in one of Downtown Orlando’s most desirable pockets. Perfectly positioned on a quiet, low-traffic street, this property offers a unique sense of tranquility while being just a short walk from the vibrant energy of downtown and the picturesque Lake Eola area.This well-appointed two-unit property combines timeless character with thoughtful upgrades throughout. Each residence has been carefully maintained and enhanced, offering a comfortable and inviting living experience that continues to attract and retain high-quality tenants, both currently in place.The property also features ample on-site parking, a highly sought-after amenity in this prime urban location, providing convenience and added value for residents and guests alike. The rear unit enjoys a fully fenced yard, offering added privacy and outdoor space—ideal for relaxation, pets, or extended tenant appeal.Surrounded by tree-lined streets and established homes, yet moments from Orlando’s top dining, entertainment, and business hubs, this location truly offers the best of both worlds — peaceful residential living with immediate access to city life.Whether you’re seeking a refined addition to your investment portfolio or a property with long-term appreciation potential in a premier location, this duplex delivers on every level.
Listing is courtesy of: LIPPI REALTY LLC (321-972-6823)
Listing Agent: Vivian Lippi (407-951-1390)
405 CALHOUN PL, ORLANDO, FL 32801
$599,90053 Days on yellowkey MLS ID: O6380196
REDUCED by $44,100 (6.8%) on 04/03/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1857 Built: 2025 Tax: $689 (2024)Community: Lake Olive HeightsSingle Family
Taxes:$689
Elementary School: Lake Como Elem
High School: Edgewater High
Tax Year: 2024
Middle School: Lake Como School K-8
Remarks: Your Dream Home in Lawsona-Fern Creek Awaits!! Imagine coming home to a space where every detail reflects modern comfort and elegance. Just completed- this brand-new custom home in the serene Lawsona-Fern Creek neighborhood of Orlando, FL, offers the perfect blend of tranquility and convenience. Located on a picturesque, tree-lined street, this is where your next chapter begins. Designed for Your Lifestyle. This 3-bedroom, 2.5-bathroom home spans 1,857 square feet, providing the ideal layout for relaxation, family time, and entertaining. The open-concept design welcomes natural light, creating a seamless flow throughout the home—every space thoughtfully designed for modern living. A Gourmet Kitchen That Inspires. At the heart of this home is a chef’s kitchen, where luxurious countertops, stylish cabinetry, and high-end appliances come together to create a space that’s both beautiful and functional. Whether preparing a quiet meal or hosting friends, this kitchen sets the stage for unforgettable moments. Elegance in Every Detail. Sophisticated finishes and modern fixtures define each space. From elegantly tiled bathrooms to designer details throughout, every element has been selected to enhance comfort and style. Prime Location & Unmatched Convenience. Located in Lawsona-Fern Creek, this home offers easy access to parks, top-rated schools, and Orlando’s vibrant downtown. Whether enjoying a stroll through the neighborhood or dining at local hotspots, everything you need is just minutes away. Secure your place in this sought-after neighborhood now and start planning your future in this stunning new home. New photos coming soon!!
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Amanda Wood (321-229-8389)
110 N BROWN AVE, ORLANDO, FL 32801
$475,00023 Days on yellowkey MLS ID: O6388981
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1925 Tax: $3,078 (2024)Community: Eola Rose AnnexSingle Family
Taxes:$3,078
Remarks: Charming 2 bedroom, 2 bath historic bungalow in Thornton Park just minutes from Lake Eola and Downtown Orlando. This character-filled home features vaulted ceilings, original hardwood floors, and a cozy wood-burning fireplace, blending historic charm with thoughtful updates. The kitchen includes a walk-in pantry and a new dishwasher (2025), offering both function and convenience. The home offers flexible living space with a den/office, perfect for working from home. One of the standout features is the original clawfoot bathtub, preserving the timeless appeal of this classic bungalow. Enjoy indoor-outdoor living with a private deck off the dining room, ideal for entertaining or relaxing. The large fenced backyard includes a double gate for easy access and provides plenty of space to add a pool or expanded outdoor living area. Located in the heart of Thornton Park, this home is within walking distance to Lake Eola, Downtown Orlando, shops, dining, and nightlife that make the neighborhood one of Orlando’s most sought-after historic districts and close proximity to 408 and I4. Relax on the welcoming front porch and enjoy the charm of one of the city’s most vibrant communities.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
155 S COURT AVE #1001, ORLANDO, FL 32801
$435,00043 Days on yellowkey MLS ID: O6383965
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1261 Built: 2007 Tax: $5,876 (2024)Community: Solaire/Plaza CondoCondo
Taxes:$5,876
Remarks: Experience elevated living at Solarie at the Plaza in the vibrant heart of Orlando. This breathtaking 10th-floor corner residence is a true modern masterpiece in the sky, offering outside living with a private balcony unique to this unit boasting unbeatable views of the City Beautiful. This two-bedroom, two-bath open floor plan showcases a striking loft-style design with sleek architecture and floor-to-ceiling windows that flood the home with natural light and frame sweeping panoramic sunsets and sparkling city lights. Upgrades throughout elevate the space, while the split-bedroom layout provides exceptional comfort and privacy. The luxurious primary suite features custom California Closets and a spa-inspired ensuite, and there’s even room to create a stylish dry bar for your morning coffee or tea ritual. In unit Laundry included in the luxurious condo. Residents enjoy a grand lobby with 24-hour concierge service, fingerprint and fob-secured entry, and the ultimate blend of sophistication and convenience. Community Pool, Fitness, and work station living area are all located on the 10th floor for great convenience. Discover the pinnacle of urban luxury where contemporary elegance meets dynamic downtown living. NOTE - Some photos are virtually staged.
Listing is courtesy of: CONWAY REALTY CORP (407-540-8888)
Listing Agent: Jane Slone (407-540-8888)
150 E ROBINSON ST #30C, ORLANDO, FL 32801
$1,295,0004 Days on yellowkey MLS ID: O6390122
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2158 Built: 2007Monthly Fee: $2,016 Tax: $17,508 (2025)Community: Vue/Lk EolaCondo
Taxes:$17,508
Remarks: Positioned on the 30th floor of The Vue at Lake Eola’s upper residential tier, this southwest corner 02 residence offers an elevated vantage point where the skyline opens into a broader horizon—layered with city, sky, and distant traces of water across the western landscape. Spanning 2,159 square feet, the residence is part of a limited collection of larger-format southwest corner layouts, defined by dual exposures and a continuous architectural wrap of glass. Natural light shifts throughout the day, transitioning into an illuminated skyline in the evening. The layout is deliberately composed, with the primary suite scaled to function as a private hotel suite, incorporating a dedicated lounge along the glass. The residence has undergone a design-led renovation centered on a full reconfiguration of the kitchen and the introduction of herringbone wood flooring—establishing the architectural foundation of the home. Custom rift-cut oak cabinetry is executed to full height with integrated storage, its vertical grain and tailored, furniture-quality finish introducing warmth and material depth. The linear cut of the wood creates a clean, architectural presence—more aligned with high-end hospitality design than traditional residential cabinetry. The herringbone wood flooring continues seamlessly beneath all millwork, introducing movement and subtle contrast while grounding the space with depth and continuity. Material selections are intentionally restrained, with matte blackened hardware and a champagne-toned faucet echoed in the lighting for a cohesive, controlled palette. An extended run of rift oak cabinetry with integrated wine storage anchors the open plan, while the living space is scaled to allow furnishings to float. The result is a space that reads as quiet luxury—where material, proportion, and restraint take precedence over ornamentation. The primary suite offers a true suite experience, with a clear separation between sleeping and living zones. A dedicated lounge sits along the glass with direct balcony access, while the sleeping area is set back - creating a more composed, restful environment that lives like a private hotel retreat. The primary bath is finished in full-height stone with a soaking tub, glass-enclosed shower, and dual vanity—offering a clean, well-proportioned space with opportunity for future customization. A walk-in closet provides substantial volume, allowing for a more tailored configuration over time. A guest en suite is positioned at the front of the residence—set apart from both the primary suite and main living areas—ensuring a high level of privacy. The additional bedroom adjacent to the primary suite is well suited as an executive office or private study. The building offers a fully serviced residential experience with 24/7 staffed security, biometric access, and valet parking - providing a level of ease and discretion expected in a luxury high-rise. Amenities include a fitness center, basketball and tennis courts, a junior Olympic pool with cabanas, club lounge, private theater, and outdoor dining. Positioned in the heart of downtown, the residence offers walkability to Lake Eola Park, the Dr. Phillips Center for the Performing Arts, and surrounding dining - allowing the city experienced as a natural extension of home.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Kathryn King (407-635-7778)
155 S COURT AVE #PENTHOUSE (2905), ORLANDO, FL 32801
$899,000165 Days on yellowkey MLS ID: O6353021
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1786 Built: 2007Monthly Fee: $1,890 Tax: $10,586 (2024)Community: Solaire/Plza CondoCondo
Taxes:$10,586
Remarks: CASH BUYERS BRING ALL OFFERS.. This is your opportunity to purchase a PENTHOUSE SUITE in the most sought high-rise in downtown Orlando at a heavily reduced price. Stay in front of the Condo curve and gain immediate equity as the Condo market begins its recovery. This is a rare find and seldom available, it is a must see! If luxury, aesthetics and entertainment are what you fancy, you have found all of that and so much more. This fully remodeled, high-tech smart Penthouse offers an unparalleled lifestyle with top-tier finishes, cutting-edge features, and breathtaking panoramic views of the City Beautiful. Step inside to discover the luxurious illuminated marble kitchen, a true centerpiece of this Penthouse, featuring customizable lighting and aesthetically pleasing style. The expansive open-concept layout is perfect for entertaining, with floor-to-ceiling windows that flood the space with natural light and offer unobstructed panoramic city views. Motorized black-out blinds are installed throughout for effortless privacy and ambiance control. The primary suite is a luxurious retreat, boasting a massive bedroom, spa-like bathroom with high-end finishes, and a separate water closet for added comfort. Throughout the unit, you'll find sleek ceramic tile flooring, ceramic tile walls, elegant color schemes, and detailed trim work that elevate the overall aesthetic like no other, including HUE lighting imbedded beneath all the baseboards throughout the Penthouse. All of your guests will impressed upon entry in this rare high-end fully remodeled Oasis. This prime location is fully walkable and just steps away from Orlando's best dining, nightlife, entertainment, sporting arenas and cultural venues including the Dr Phillips Performing Arts Center. There are two reserved secured parking spots located right by the resident elevator in the nested parking garage with 24 hour surveillance. Park your car and enjoy the vibrant and walkable downtown lifestyle. Solaire at the Plaza is currently undergoing an exciting transformation, further enhancing its status as Downtown Orlando's Premier Residential Tower. Enjoy 24 hour concierge service and facial recognition biometric entry, solidifying that Solaire keeps resident safety 1st place. Seeing is truly believing in this spectacular Penthouse soaring far above the rest, move-in ready and awaiting your arrival. Bring me your offer!
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Jude Devito (352-427-2070)
101 S EOLA DR #1202, ORLANDO, FL 32801
$489,900156 Days on yellowkey MLS ID: O6356604
REDUCED by $19,000 (3.7%) on 03/31/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1740 Built: 2008 Tax: $9,179 (2024)Community: 101 Eola CondosCondo
Taxes:$9,179
Remarks: 101 Eola – Penthouse Residence with Office/Den | Downtown Orlando, FL 32801 Experience chic urban luxury in this penthouse-level residence at the iconic 101 Eola Condominiums, perfectly positioned in the heart of Orlando’s sought-after South Eola–Thornton Park District. This spacious open-concept unit features a dedicated office/den, ideal for remote work, creative projects, or guest accommodations. The residence showcases expansive skyline views from its large private balcony—perfect for entertaining or simply enjoying the vibrant city energy below. Step inside to find floor-to-ceiling emerald glass architecture, 10-foot ceilings, and premium finishes throughout, including stainless steel appliances, granite countertops, ceramic tile, and wood flooring. The penthouse layout offers abundant natural light, modern design, and livable comfort. Recent building renovations further elevate the experience with fresh exterior paint, comprehensive window sealing, and a fully updated clubhouse, pool, and hot tub. Building Highlights & Amenities: • 24-hour concierge and controlled access • Resort-style 5th-floor pool deck with hot tub and sauna • Contemporary fitness center • Entertainment lounge and media room • Assigned garage parking and guest parking • Ground-floor restaurants, cafés, and boutique retail • Walkable access to Publix Urban Market, Lake Eola Park, and Thornton Park boutiques Community & Lifestyle: 101 Eola stands as a distinctive 12-story glass landmark, surrounded by oak-lined streets, historic bungalows, and the lively downtown scene—an exceptional blend of sophistication, comfort, and walkability. Legal & Financial Disclosures: The monthly Homeowners’ Association (HOA) dues include repayment of a ten-year HOA loan, currently estimated at $361.94 per month. The HOA’s reserve fund and Special Infrastructure Reserve Schedule (SIRS) are fully funded per the adopted reserve plan. Disclaimer: The monthly HOA dues reflect inclusion of the loan repayment of approximately $361.94. All financials, reserves, assessments, and HOA disclosures are subject to verification by the buyer. Features: 10’ Ceilings | Office / Den | Concierge | Controlled Access | Entertainment Lounge | Floor-to-Ceiling Glass | Granite Counters | Guest Parking | Gym | Hot Tub | Laundry | Private Balcony | Pool | Sauna | Stainless Steel Appliances | Street Parking | TV Cable | Washer & Dryer | WiFi | Window Coverings | Wood Floors Offered Exclusively at 101 Eola – The Epitome of Downtown Penthouse Urban Living.
Listing is courtesy of: URBANISTA BROKERS (407-619-7272)
Listing Agent: Thomas Williams (407-619-7272)
101 S EOLA DR #808, ORLANDO, FL 32801
$210,00085 Days on yellowkey MLS ID: O6372612
Bed: 1 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 644 Built: 2008 Tax: $3,488 (2025)Community: Eola CondosCondo
Taxes:$3,488
Remarks: Stunning 8th floor condominium in the luxury 101 Eola high rise! This freshly painted one bedroom features a sectioned bedroom, full bathroom with walk-in closet, gorgeous kitchen and living area with floor to ceiling windows. The kitchen boasts beautiful cherry cabinetry, granite countertops, stainless steel appliances, and a breakfast bar. Relax on the balcony and enjoy the panoramic view of other downtown neighborhoods and skyline. This unit includes a washer/dryer and two assigned parking spaces and a storage unit. The building has undergone extensive renovation that includes waterproofing all windows and balconies, fresh exterior paint, new roof, new access control system, and security camera. All new outstanding amenities such as a newly renovated community pool, spa, sauna, freshly painted and new carpeted clubhouse with pool table and outdoor lounge area, a full fitness center, guest lobby and a 24-hour concierge! The building has just been approved for FHA Financing. You cannot beat this downtown location near Lake Eola, restaurants, shopping, and entertainment! THIS UNIT HAS TWO ASSIGNED PARKING SPACES AND AN ADDITIONAL STORAGE UNIT!!
Listing is courtesy of: GATE PROPERTIES & MANAGEMENT INC (407-704-7904)
Listing Agent: Nicholas Wild (407-704-7904)
5 JAMES AVE, ORLANDO, FL 32801
$585,0002 Days on yellowkey MLS ID: O6395190
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1601 Built: 1928 Tax: $7,795 (2025)Community: Thornton Park AddSingle Family
Taxes:$7,795
Middle School: Howard Middle
Remarks: Welcome to 5 James Avenue, a nearly 100-year-old home blending historic charm with thoughtful updates designed for today’s lifestyle. Offering 3 bedrooms, 2 bathrooms, and approximately 1,600 square feet of living space. The interior has been thoughtfully remodeled with an updated kitchen, renovated bathrooms, and new flooring throughout, creating a clean and cohesive feel while maintaining the home’s historic charm. The HVAC was recently replaced in 2025; ensuring comfortable living without the worry. Outside, the fully paved backyard provides a functional, low-maintenance space ideal for entertaining or relaxing. A detached storage shed or garage adds versatility, while the extra-long driveway provides ample parking which is something that’s hard to come by in this area. Situated just minutes from Lake Eola Park, you’re within a leisurely distance to some of Orlando’s top-rated restaurants, coffee shops, and local favorites, making it easy to enjoy the vibrant downtown lifestyle. If you’ve been looking for a home with soul, style, and a prime location, 5 James Avenue is truly one-of-a-kind. Schedule your private tour today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Riki Cantelli (919-757-8551)
151 E WASHINGTON ST #611, ORLANDO, FL 32801
$209,0001 Day on yellowkey MLS ID: O6395456
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 831 Built: 1963Monthly Fee: $665 Tax: $3,734 (2025)Community: Metropolitan/Lk EolaCondo
Taxes:$3,734
Remarks: Your urban oasis awaits in the heart of Downtown Orlando! This beautifully maintained 2BR/2BA unit at The Metropolitan puts you directly across from Lake Eola Park, home to swan boats, Sunday Farmers Markets, and year-round festivals. Spanning 831 SF, this unit features an open-concept living area with light, aesthetic tones, and high-quality flooring. Enjoy the ultimate convenience of a walkable lifestyle with Publix, the Dr. Phillips Center, and vibrant nightlife just a short stroll away. Building highlights include a resort-style pool deck, a fully equipped gym, and a clubhouse perfect for entertaining. Secure building access and assigned garage parking provide peace of mind in this bustling city center. Whether you're looking for a turnkey residence or a rental-ready property, this condo offers exceptional value in Orlando's premier location.
Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)
Listing Agent: Ozan Cifci (407-782-4866)
155 S COURT AVE #1507, ORLANDO, FL 32801
$275,000618 Days on yellowkey MLS ID: G5084958
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 730 Built: 2007 Tax: $3,540 (2023)Community: Solaire/Plaza CondoCondo
Taxes:$3,540
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. The Solaire at the Plaza in downtown Orlando offers luxurious living. This Studio Condo on the 15th floor features modern design elements such as floor-to-ceiling windows, marble flooring, stone walls, and premium finishes. Advanced technology includes a surround sound system, built-in TVs, electronic blinds, and recessed lighting. The bathroom boasts opulent features like marble countertops, upgraded fixtures, and an integrated TV. The chef's kitchen has granite countertops and stainless-steel appliances with stunning downtown views. Solaire at the Plaza includes a security desk, fitness center, media and game room, rooftop pool, and grill stations. The Association is set to upgrade the pool and common areas (check with association for details and timeline). With its central location near various attractions, this condo offers a lifestyle tailored for urban exploration and luxury living.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Vanessa Rattigan (352-720-0920)
530 S EOLA DR, ORLANDO, FL 32801
$999,90086 Days on yellowkey MLS ID: O6372256
0 Days Off yellowkey (back on 2/16/2026)
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3273 Built: 1925 Tax: $8,346 (2024)Community: F T Poynters AddSingle Family
Taxes:$8,346
Elementary School: Blankner Elem
High School: Boone High
Middle School: Blankner School (K-8)
Remarks: Under contract-accepting backup offers. This completely modernized historic residence offers the rare combination of luxury downtown living and built-in income potential with a DETACHED IN-LAW SUITE and sitting on a rare QUARTER ACRE LOT. Just steps from Lake Eola Park and a one-minute walk to beautiful Lake Cherokee. The main home has been thoughtfully renovated throughout, blending modern upgrades with preserved historic charm and character. Inside, you’ll find a renovated kitchen, two spacious bedrooms, and a versatile flex space on the main level—ideal for a home office, studio, or additional living area. Upstairs, the expansive primary suite features a generous walk-in closet. Additionally, you'll find 2 more bedrooms that open to a private deck overlooking the backyard. A standout feature of the property is the 750 sqft DETACHED IN-LAW SUITE, complete with one bedroom, one bathroom, a living area, and a full kitchen. Currently generating $1,900+ per month, it offers excellent income potential or flexibility for multi-generational living. Additional highlights include a 3-CAR GARAGE, NEW ROOF (installed May 2025) with a transferable 7-year warranty, and a rare ¼-acre downtown lot—providing ample space for a large swimming pool and expanded outdoor living. The outdoor space has been recently enhanced with a NEWLY INSTALLED DECK, custom pavers, and a fireplace, creating an ideal setting for entertaining or relaxing year-round. Situated on South Eola Drive in one of Downtown Orlando’s premier residential neighborhoods, this home offers walkable access to Lake Eola’s Sunday farmers market, dining, and cultural attractions—while being surrounded by tree-lined streets, historic architecture, and strong long-term appreciation. A truly unique opportunity to own a move-in-ready downtown home with income potential, space, and an unbeatable location!
Listing Agent: Jason Asa (407-337-7702)
705 DELANEY AVE, ORLANDO, FL 32801
$2,710,00012 Days on yellowkey MLS ID: O6382619
Bed: 7 Bath: 7.5 Gar: 2 Liv Area Sq Ft: 5828 Built: 1922 Tax: $31,260 (2024)Community: AlisaSingle Family
Taxes:$31,260
Remarks: 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.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Jennifer Sloan (407-810-8333)
101 S EOLA DR #1209, ORLANDO, FL 32801
$497,900156 Days on yellowkey MLS ID: O6356643
REDUCED by $1,000 (0.2%) on 03/31/2026
Remarks: 101 Eola #1209 – Luxury Penthouse Residence with Bonus Room/Den | Floor-to-Ceiling Glass Lines Experience the pinnacle of contemporary urban luxury in this penthouse-level residence at the iconic 101 Eola Condominiums, perfectly situated in the heart of the Eola South–Thornton Park District, one of Orlando’s most stylish and walkable neighborhoods. This spacious open-concept home offers a bonus room/den or private office, ideal for remote work, creative pursuits, or guest accommodations. The expansive private balcony captures panoramic skyline views and abundant natural light... perfect for entertaining or simply enjoying the vibrant rhythm of downtown living. Inside, the residence showcases floor-to-ceiling emerald glass architecture, 10-foot ceilings, and high-end finishes throughout, including stainless steel appliances, granite countertops, ceramic tile, and wood flooring. The penthouse design delivers an impressive combination of natural light, volume, and sophisticated comfort. Recent Building Renovations: The building has undergone extensive capital improvements, including fresh exterior paint, full window sealing, and upgrades to the clubhouse, pool, and hot tub, enhancing both its visual appeal and long-term investment value. Building Highlights & Amenities: • 24-hour concierge and controlled access • Resort-style 5th-floor pool deck with hot tub • Contemporary fitness center • Entertainment lounge and media room • Two assigned garage parking spaces • Ground-floor restaurants, cafés, and boutique retail • Walkable access to Publix Urban Market, Lake Eola Park, and Thornton Park’s shops and eateries Lifestyle & Location: 101 Eola rises 12 stories of signature emerald glass design, surrounded by oak-lined streets, historic bungalows, and Thornton Park’s lively cafés and markets. The building’s combination of refined architecture, boutique amenities, and premier downtown convenience make it one of Orlando’s most desirable residential addresses. Legal & Financial Disclosures: Monthly Homeowners’ Association (HOA) dues include repayment of a ten-year HOA loan, currently estimated at $361.94 per month. The HOA’s reserve fund and Special Infrastructure Reserve Schedule (SIRS) are fully funded in accordance with the adopted reserve plan. Disclaimer: Monthly HOA dues reflect inclusion of the loan repayment of approximately $361.94. All financials, reserves, assessments, and HOA disclosures are subject to independent buyer verification. Features: 10’ Ceilings | Bonus Room / Den / Office | Concierge | Controlled Access | Entertainment Lounge | Floor-to-Ceiling Glass | Granite Counters | Guest Parking | Gym | Hot Tub | Laundry | Private Balcony | Pool | Stainless Steel Appliances | Two Garage Parking Spaces | Storage | Street Parking | Cable | WiFi | Window Coverings | Wood Floors Offered Exclusively at 101 Eola – The Pinnacle of Contemporary Downtown Living. Legal & Financial Disclosures: The monthly Homeowners’ Association (HOA) dues include repayment of a ten-year HOA loan, currently estimated at $361.94 per month. The HOA’s reserve fund and Special Infrastructure Reserve Schedule (SIRS) are fully funded in accordance with the adopted reserve plan. Disclaimer: The monthly HOA dues reflect inclusion of the loan repayment of approximately $361.94. All financials, reserves, assessments, and HOA disclosures are subject to independent verification by the buyer.
150 E ROBINSON ST #2409, ORLANDO, FL 32801
$575,000233 Days on yellowkey MLS ID: O6336112
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1261 Built: 2007 Tax: $8,312 (2024)Community: Vue/Lk EolaCondo
Taxes:$8,312
Remarks: Enjoy the breath taking panoramic view of Lake Eola & Downtown ='s skyline city beautiful Orlando, Florida. This high rise Condo at he Vue was recently updated with a newly remodeled Master bathroom, brand new top of the line LG refrigerator, new faucet and disposal in kitchen and entry way new electronic thermostat.
Listing is courtesy of: ASPIRE REALTY INC (407-737-7478)
Listing Agent: Andre Rattray (407-715-9633)
665 JACKSON ST, ORLANDO, FL 32801
$859,00037 Days on yellowkey MLS ID: O6384794
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2029 Built: 2016Monthly Fee: $653 Tax: $13,746 (2025)Community: Brownstones Of Thorton ParkTownhouse
Taxes:$13,746
Remarks: PRICE ADJUSTMENT Experience refined urban living at The Brownstones, nestled in Thornton Park—one of Orlando’s most sought-after neighborhoods. Just steps from the vibrant heart of Downtown Orlando, Thornton Park offers the city’s premier dining, entertainment, and cultural experiences, all within a charming historic setting.This elegant three-story, 3-bedroom, 3.5-bath brownstone faces the serene Constitution Green and blends the convenience of modern construction with timeless architectural character. Inside, you’ll find luxury finishes throughout, including:*Thermador natural gas appliances*Granite countertops*Porcelain wood-look flooring*Marble primary bath with double vanities, freestanding soaking tub, and separate shower*Spacious walk-in closets*High ceilings on every levelEnjoy outdoor living on your private rooftop terrace, perfect for relaxing or entertaining. A two-car rear-entry garage adds everyday convenience to this exceptional home.
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Jay Wood (407-405-3800)
204 E SOUTH ST #4056, ORLANDO, FL 32801
$217,500312 Days on yellowkey MLS ID: O6310667
REDUCED by $7,400 (3.3%) on 04/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1215 Built: 2002Monthly Fee: $855 Tax: $2,591 (2024)Community: Grande Downtown Orlando CondoCondo
Taxes:$2,591
Remarks: Freshly painted in neutral color. *One Year HOME WARRANTY. Located in the heart of downtown, this spacious 2 bedroom 2 bathroom has a pool view from the balcony. This split floor plan corner unit has similar sized master and guest bedrooms. Walk-in closets, oversized tubs in both bathrooms, dual sink vanity in master bath, ceiling fans. The Grande features amenities which include a private fitness center and community pool. Only steps from the Dr. Phillips Center for the Performing Arts, Lake Eola, shopping, resturants and entertainment. AC replaced in 2021. Two reserved parking spots in addition to guest parking. VACANT SO EASY SHOW.
Listing is courtesy of: COSMOPOLITAN HOME REALTY LLC (407-644-4663)
Listing Agent: Shailesh Limbachia (407-765-9563)
202 E SOUTH ST #2039, ORLANDO, FL 32801
$214,9003 Days on yellowkey MLS ID: O6395211
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1115 Built: 2002Monthly Fee: $803 Tax: $3,883 (2025)Community: Grande Downtown OrlandoCondo
Taxes:$3,883
Remarks: Experience comfortable downtown living in this well-maintained condo located in the heart of Orlando, offering convenient access to dining, entertainment, shopping, and major roadways. This 2-bedroom unit features an open-concept layout connecting the kitchen, living, and dining areas—creating a functional and inviting space for both everyday living and entertaining. Faux walnut flooring flows throughout, adding warmth and continuity to the interior. The kitchen is equipped with updated appliances and modern lighting fixtures, blending style and practicality. The living area extends to a private balcony overlooking the community pool and landscaped courtyard, where a desirable south-facing exposure brings in natural light and provides a peaceful outdoor retreat. Ideally situated near Lake Eola Park, Thornton Park, and the downtown business district, this home offers the perfect balance of vibrant city access and comfortable residential living.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Mary Herrod De Boer (219-771-1332)
860 N ORANGE AVE #159, ORLANDO, FL 32801
$279,00030 Days on yellowkey MLS ID: O6385787
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1070 Built: 2000Monthly Fee: $518 Tax: $4,647 (2025)Community: Park North/Cheney PlaceCondo
Taxes:$4,647
Elementary School: Princeton Elem
Middle School: College Park Middle
Remarks: Beautiful Condo in the heart of Downtown Orlando - Park North at Cheney Place. This beautiful 2 bed / 2 baths First Floor well-maintained, pet friendly, split master bedroom layout - each with their own bathroom and walk in closet. Vinyl floors throughout. Enjoy in-unit laundry with a washer and dryer conveniently tucked away in a dedicated laundry closet, walk out to covered patio with view to the courtyard, perfect for morning coffee and relaxation. You will also have a secure, gated parking in your own dedicated one-car garage space, with the option to add a second space. Key-card building access ensures peace of mind. and amenities including two tropical pools, Club room with a billiard table, two fully-equipped fitness centers, on-site business center and two fenced dog parks. Convenient location with easy pedestrian access to downtown via the overpass across Colonial Walk to dining, entertainment. Steps away is the scenic Urban Trail for biking, jogging, or a relaxing stroll. Don't miss your opportunity to live in this prime location in Orlando!!
Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)
Listing Agent: Ken Warren (407-370-4400)
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