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408 Holt Avenue, Winter Park
$745,000
2 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code
Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.

408 Holt Avenue, Winter Park

4947 N Palm Avenue, Winter Park
$515,000
Suburban Homes SubDv. ⋅ 32792 Zip Code
Prime Freestanding Commercial Opportunity in the heart of Winter Park! This versatile property is zoned 1210 – Store/Office/Residential II, offering flexible use for investors, owner-occupants, or live/work scenarios. Previously utilized as a real estate office and currently operating as a counseling center, the layout easily adapts to a wide range of professional or service-based businesses including legal, financial, medical, wellness, or boutique retail. Strategically positioned directly across from the United States Postal Service, the property benefits from consistent daily traffic and strong visibility. Located along N Palm Avenue with quick connectivity to major corridors including State Road 436, State Road 417, and State Road 408, providing seamless access to the greater Orlando metro and both major airports. Surrounded by established residential communities and professional offices, and just minutes from the highly desirable Winter Park amenities including dining, retail, and business services. The property features a functional floor plan, a 12x12 storage addition, and a newly upgraded paver driveway enhancing curb appeal and client accessibility. An exceptional opportunity to own a standalone building in a high-demand area where commercial inventory is limited. Ideal for businesses seeking visibility, accessibility, and long-term growth potential, or investors looking for a strong rental asset in a thriving corridor.

4947 N Palm Avenue, Winter Park

446 Melrose Avenue, Winter Park
$1,495,000
4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

726/720 N Pennsylvania Avenue, Winter Park
$999,000
6 Beds ⋅ 4 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.

726/720 N Pennsylvania Avenue, Winter Park

7393 Grand Avenue, Winter Park
$325,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Short Sale. SHORT SALE – SUBJECT TO THIRD-PARTY LENDER APPROVAL. Investor and builder opportunity in Winter Park. This property is situated on a generously sized lot with no HOA and offers potential for renovation, rental use, resale, or redevelopment, subject to applicable zoning, permitting, and governmental approvals. The existing residence provides a starting point for a value-add renovation, while the lot may offer additional possibilities for builders or investors. Buyer is responsible for independently verifying zoning, land use, development potential, lot dimensions, property condition, measurements, school information, and intended use. Conveniently located near shopping, dining, parks, and major roadways. Property is being sold AS-IS, with the right to inspect. Seller will not make repairs. All offers are subject to lender approval. Allow additional time for short-sale review and approval.

7393 Grand Avenue, Winter Park

901 Enclave Place, Winter Park
$1,550,000
4 Beds ⋅ 4 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code
Under Construction. Buyer Incentive Limited time - Choose from $30,000.00 cash credit or $40,000 credit towards upgrades. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. Design book is available upon request. Please inquire for details and customization options.

901 Enclave Place, Winter Park

905 Enclave Place, Winter Park
$1,550,000
4 Beds ⋅ 4 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code
Under Construction. Under Construction Buyer Incentive Limited time - Choose from $30,000.00 cash credit or $40,000 credit towards upgrades.The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located, walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.

905 Enclave Place, Winter Park

1927 Eland Avenue, Winter Park
$799,000
5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code
A rare single family home with a HUGE guest house, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park

1113 Via Del Mar, Winter Park
$1,595,000
3 Beds ⋅ 2 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code
Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

1751 Goodrich Avenue, Winter Park
$1,380,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code
Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

1751 Goodrich Avenue, Winter Park

330 Elkhorn Court, Winter Park
$509,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Merrie Oaks SubDv. ⋅ 32792 Zip Code
Virtually Staged. Owner welcomes all offers! Seller is motivated and open to considering all reasonable offers. Schedule your showing today! 330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.

330 Elkhorn Court, Winter Park

3425 Forsyth Road, Winter Park
$2,500,000
32792 Zip Code
Looking for the next location of your current or future business? There is no better place than this! Located in the heart of Winter Park and zoned for C-3, this space is right next to popular foot traffic places such as Costco and Full Sail University, as well as several apartments and shopping centers which would greatly increase the chance of profit! An amazing thing about this deal is the two in one package it has, having two facilities! The front building is massive, offering a giant open space with several office rooms and bathrooms. The second building behind the front building has even more office spaces, bathrooms, and most importantly can be leased or rented! There is no need to worry about parking, the parking space can fit several cars!

3425 Forsyth Road, Winter Park

2231 Nairn Drive, Winter Park
$499,000
3 Beds ⋅ 2 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code
Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

2231 Nairn Drive, Winter Park

230 Strathy Lane, Winter Park
$499,000
2 Beds ⋅ 1 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code
Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

230 Strathy Lane, Winter Park

560 Ololu Drive, Winter Park
$849,000
2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

311 Scottsdale Square Unit 311, Winter Park
$109,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.

311 Scottsdale Square Unit 311, Winter Park

503 N Interlachen Avenue, Winter Park
$4,500,000
Winter Park SubDv. ⋅ 32789 Zip Code
RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses. Future residents will enjoy picturesque walks along Winter Park's famous brick streets just off the shores of the chain of lakes. Nearby attractions like the Winter Park Farmer's Market, the Winter Park Golf Course, a highly rated 9-hole gem in the center of town, Casa Feliz, Central Park, and more are all within just a few minutes stroll.

503 N Interlachen Avenue, Winter Park

3071 George Mason Avenue Unit 5, Winter Park
$89,900
1 Baths ⋅ Colonies SubDv. ⋅ 32792 Zip Code
Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat! Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to maintain. Enjoy a bright and open layout, a well-equipped kitchen, and a full bathroom, all designed for convenience and efficiency. Step outside to your private covered patio, where you can relax while overlooking the serene courtyard setting. Whether you’re looking for a low-maintenance home or a smart investment opportunity, this condo checks all the boxes. Schedule your showing today!

3071 George Mason Avenue Unit 5, Winter Park

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