32789 Zip Code FL Multi-Family Real Estate, Homes for Sale

2 Beds ⋅ 2 Baths ⋅ Mack Peter Rev SubDv. ⋅ 32789 Zip Code

Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

901 Harmon 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

$1,185,999

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

$640,000

4 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Beautiful income-producing duplex located in the highly desirable Winter Park area! This well-maintained property features two units, each offering 2 bedrooms, 1 bathroom, and a dedicated utility room for added convenience. Both sides provide functional layouts with comfortable living spaces, making it ideal for tenants or owner-occupants looking to offset their mortgage. Situated on Indiana Ave, this property is just minutes from Park Avenue, shopping, dining, and major roadways, offering both convenience and strong rental appeal. Whether you're looking to expand your investment portfolio or live in one unit while renting the other, this duplex presents a fantastic opportunity in a prime location.

1618 Indiana Avenue, Winter Park

$1,050,000

6 Beds ⋅ 4 Baths ⋅ Huntington Court SubDv. ⋅ 32789 Zip Code

Welcome to 831 & 833 Huntington Court, a rarely available duplex tucked away on a quiet cul-de-sac in one of Winter Park’s most walkable and desirable locations. Just minutes from Park Avenue, local lakes, dining, shopping, and entertainment, this property offers the perfect blend of privacy, convenience, and long-term value. Both properties are beautifully landscaped and have pavered driveways offering plenty of parking for the residents and their guests. Each thoughtfully designed unit lives like a single-family home. Both sides feature private, fully fenced yards complete with patios ideal for outdoor dining or relaxing, as well as access to a shared saltwater pool. Additional amenities include two storage sheds, one for pool equipment and another for general storage. Inside, each property welcomes you directly into the living room, which flows naturally into the updated kitchen. In addition to the living room, each unit offers a flexible downstairs room that can be used as a sitting area, separate dining space, home office, or additional living area, allowing the home to adapt to a variety of lifestyles. Each unit offers a functional and inviting layout with one bedroom and full bathroom downstairs, and two bedrooms with a full bathroom upstairs. The downstairs features tile flooring throughout, an updated kitchen with granite countertops, stylish backsplash, stainless steel appliances, under-cabinet lighting, and a breakfast bar with overhang seating. Indoor laundry and ample cabinetry are conveniently located near the kitchen, and generous closet space can be found throughout both homes. Upstairs, you’ll find two comfortable bedrooms with newer carpet and a shared bathroom, creating a private and peaceful retreat. Each unit features a front porch with a portico to the one car garage. Lovingly maintained over the years, this duplex offers exceptional privacy, great walkability, and versatile use. It's ideal as a long-term rental investment, or for an owner-occupant looking to live in one unit while enjoying income from the other. It's truly a special opportunity in the heart of Winter Park.

831/833 Huntington Court, Winter Park

$630,000

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$429,000

2 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

ATTENTION INVESTORS!!! DIAMOND LOCATION!! THIS IS THE MOST WONDERFUL OPORTUNITY FOR BUYING YOUR DREAM DUPLEX WITH 1 BED 1 BATH ON EACH OF TWO FLOORS IN THE MOST DISERABLE AREA FOR LIVING CALLED WINTER PARK IN THE 32789 ZIDE CODE. NO HOA NEITHER CDD. IT IS LOCATED JUST MINUTES FROM PARK AVE., ROLLING COLLEGE, AND TONE OF RESTAURANTS!! EACH UNIT HAS 1 BED 1 BATH WITH ITS COZY KITCHEN, AND NICE FAMILY ROOM. THIS DUPLEX HAS A ENORMEOUS POTENTIAL INCOME. GREAT SCHOOLS!!, NEAR TO HIGH-WAYS!! RIGHT PRICE!! IT WILL NOT LAST LONG!!

441 Clay Street, Winter Park

$662,500

4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Explore this unique and profitable opportunity to invest in this charming duplex in historic Winter Park! Nestled among luxury and lakefront homes in the much sought after "College Quarter." This duplex features 2 units, each with a 2-bedroom, 1-bathroom units both with a light and airy sunroom, functional laundry room, courtyard area, and 2 parking spots (4 total). Unit 600 is approximately 1193 square feet and features a beautiful sunroom, courtyard, kitchen and UPDATED bathroom. Rental income for 600 is presently $1900/month which expires 7/31/25. Unit 602 is approximately 1303 square feet and features an UPDATED bathroom, lawn space and nicely appointed kitchen. Rental income for 602 is presently $1800/month which expires 5/31/25. Both units in this duplex include the washer and dryer. This duplex is a 5 to 10 minute stroll to Lake Virginia, Rollins College, Dinky Dock and the Winter Park Tennis Center. Also within walking and bicycling distance are the Park Ave shops and restaurants and the Winter Park Farmer's Market. I-4 is 10 minutes away and the Orlando International Airport is 30 minutes away. Duplexes such as this are a rare find in this area and don't come on the market often. Take advantage of this opportunity to invest and prosper in the Winter Park community TODAY! Roof 2007, Plumbing 2018. Unit 600- HVAC 2018, Water Heater 2012. Unit 602- HVAC 2017, Water Heater 2004.

600 Huntington Avenue, Winter Park

$656,000

4 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32789 Zip Code

Highly in demand, charming and rare 2 unit duplex for sale near the “College Quarter” in Winter Park: each unit offers 2 bedrooms and 1 bath plus each side has its own laundry room with washer/dryer included. Surrounded by luxury townhomes, lakefront mansions, and located on a tree lined, brick street close to Winter Park's famed Park Ave, it’s just a short 5 to10 minute walk to the shore of beautiful Lake Virginia and Rollins College campus. White tile floors run throughout unit 1101 & terra cotta tile is in unit 1107, with plenty of light coming through the energy efficient double pane windows. Both units have access to their own private paver patio to enjoy the lovely evening weather in beautiful Winter Park. There’s plenty of off-street parking with 2 dedicated spots in front and 2+ additional dedicated parking spots in back for residents and guests as well. Great value in just the land for future development too with the availability to start fresh and build two very large townhouses for resale, each over 2,000+ sq ft and each having a 1 car garage. The back unit is currently rented for $1,800 per month with lease through May 2025. The other unit is currently vacant and can easily be shown. Too many improvements to list here, please see features/updates attachments.

1101 S Pennsylvania Avenue, Winter Park

$2,925,000

18 Beds ⋅ 18 Baths ⋅ Minnesota Condos SubDv. ⋅ 32789 Zip Code

Welcome to your income-producing oasis in the heart of Winter Park! These exclusive townhomes complex boasts six units, providing a rare opportunity for full control with no HOA fees. Each unit offers three bedrooms and two and a half bathrooms, fully upgraded to meet the highest standards of modern living, In addition 2 car garage , large upper patio and a fenced backyard. Recent renovations include a brand-new roof, redone in March 2021, ensuring durability and peace of mind for years to come. Select units feature new HVAC systems and water heaters, adding to the appeal of this investment opportunity. Strategically positioned, this property is a mere 5-15 minutes away from Downtown Orlando, the Mills District, and Downtown Winter Park, offering unparalleled convenience and access to the vibrant pulse of the city. Despite its prime location, all leases are currently under market value, presenting a promising chance to maximize returns. Currently fully occupied, these units offer below-market rents, making them an attractive proposition for investors seeking immediate cash flow. The updated interiors ensure tenant satisfaction and minimal maintenance, allowing you to build your portfolio effortlessly. Situated in the bustling Winter Park area, this property is surrounded by a myriad of shopping, dining, and entertainment options, catering to the diverse needs of tenants. Additionally, its close proximity to Rollins College adds to its appeal, attracting a steady stream of potential renters seeking convenience and quality living. Don't miss out on this exceptional opportunity to own six income-producing properties in one of Winter Park's most sought-after locations. Seize the chance to secure your financial future with this lucrative investment. Schedule a viewing today and experience the essence of effortless property ownership!

875 Miles Avenue Unit 4, Winter Park

$575,000

4 Beds ⋅ 4 Baths ⋅ Magnolia Sub SubDv. ⋅ 32789 Zip Code

This outstanding investment opportunity is strategically positioned between the vibrant downtown area of Winter Park. Boasting close proximity to upscale shopping centers, key transportation arteries, and renowned educational institutions, the property stands as a prime investment with unparalleled appeal. The property has been upgraded with a New Roof and New A/C Central Unit.

1256 Michigan Avenue, Winter Park

$455,000

2 Beds ⋅ 2 Baths ⋅ Harper Place SubDv. ⋅ 32789 Zip Code

A prime investment opportunity with a remarkable location. Close to shopping centers, major highways like I-4 and the 408, esteemed institutions like Rollins College, Valencia College and UFC, and nestled between vibrant downtown areas of Orlando and Winter Park. The property offers both convenience and potential for savvy investors. Don't miss out on this extraordinary prospect!

1271 Miller Avenue, Winter Park

$470,000

3 Beds ⋅ 3 Baths ⋅ Pines SubDv. ⋅ 32789 Zip Code

Welcome to the ultimate investment opportunity in Winter Park! We are thrilled to present to you this phenomenal TRIPLEX that boasts a remarkable occupancy history. This gem is an absolute rarity, nestled in one of the most sought-after locations in town. Don't let this golden chance slip through your fingers – seize the moment and come see it TODAY! Positioned just a stone's throw away from the prestigious Dubsdread Golf Course and Country Club, this trilevel treasure offers unrivaled convenience. Imagine waking up to stunning views of the lush green fairways or enjoying a relaxing afternoon on the verdant patio – the possibilities are endless! But that's not all, folks! This extraordinary property is surrounded by a plethora of amenities that Winter Park has to offer. From the vibrant Winter Park Village to the world-renowned Florida Hospital/Advent Health and the bustling Calvary Orlando, you'll find yourself at the heart of it all. And let's not forget the incomparable shopping, dining, and parks that await you in the vibrant enclave of College Park, just a stone's throw away. The location is truly a masterpiece, but what about the property itself? Well, let us assure you that it matches the splendor of its surroundings. With three separate units, each radiating its own unique charm, this TRIPLEX promises versatility and endless possibilities. Whether you're an astute investor looking to maximize returns or a savvy homeowner seeking to offset expenses, this is an opportunity that cannot be missed. Step inside and be mesmerized by the exquisite architecture and thoughtful design. Each unit showcases spacious living areas flooded with natural light, creating an inviting and warm atmosphere. Picture yourself preparing delicious meals in the well-appointed kitchens, entertaining friends and family in the generous living spaces, or enjoying some well-deserved relaxation in the peaceful bedrooms. Investing in this TRIPLEX means becoming a part of Winter Park's thriving community, where timeless elegance meets modern convenience. The potential for long-term growth and substantial returns awaits you. So, what are you waiting for? Don't hesitate, come explore this rare gem today! The perfect investment opportunity is calling your name. Reach out now and let us help you make your real estate dreams come true.

2040 Jewell Avenue, Winter Park

$480,000

Karolina On Killarney SubDv. ⋅ 32789 Zip Code

MULITPLE OFFERS HIGHEST AND BEST BY SUNDAY 27TH BY 5pm, Charming Winter Park Duplex located in 32789 has been completely refreshed for a new investor to immediately start make cash flow. Each unit is a 2 bedroom 1 bath with updated kitchens and baths. With all the character of the era left in place so the charm is abundant throughout. Each unit has washer and dyer hook-up and a large exterior shared storage building.

1960 Staunton Avenue, Winter Park

$520,000

Metzingers Add SubDv. ⋅ 32789 Zip Code

Close to hospital, shops, school, entertainment, I4, 408, markets, restaurants, medical buildings, few miles to Orlando and Winter Park's downtown, golf course, tennis courts, and public boat dock. Five minutes from Rolins and Valencia Community College. 5 minutes to Park Avenue and US Post Office.

1321 Harmon Avenue, Winter Park

$?

Lawndale SubDv. ⋅ 32789 Zip Code

Great duplex in Winter Park-College Park! VERY EASY TO RENT! Live in one and rent the other OR just rent both!!! Won't last! Both currently leased!!Great investment opportunity in Winter Park (College Park area). Both homes are currently leased. The rear home(which is larger) is a month to month lease @ $800.00/mo. The front home is leased through July 2002 @ $700.00/mo. Owner is licensed broker.

2020 Miller, Winter Park

32789 Zip Code Multi-Family Real Estate & Homes

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