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$210,000
2 Beds 3 Baths Whisperwood Condo SubDv. 32792 Zip Code
Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered parking plus additional guest parking, Community pool. The HOA covers exterior maintenance, roof, trash, landscaping and community pool, allowing owners to enjoy a low maintenance lifestyle. Why You'll Love It !! This well maintained townhome offers the perfect combination of comfort, convenience, and value. The bright, open floor plan is ideal for everyday living, while the two upstairs ensuite bedrooms provide privacy for homeowners, guests, or roommates. Enjoy your morning coffee or unwind in the evening on the private fenced patio—your own outdoor retreat. Prime Winter Park Location: Conveniently located just minutes from: Full Sail University, University of Central Florida (UCF), Downtown Winter Park, Major highways (417 & 408), Shopping, dining, parks, and entertainment Great Opportunity, Whether you're a first-time homebuyer, downsizing, or looking for an investment property, this home offers exceptional value in one of Central Florida's most convenient locations. Schedule your private showing today and discover everything this Winter Park townhome has to offer.

7488 Whisperwood Drive Unit 28, Winter Park

$199,000
2 Beds 2 Baths Whisperwood Condo SubDv. 32792 Zip Code
One of the lowest-priced homes in Winter Park with nearly 1,400 square feet, a private carport, screened balcony, community pool, and easy access to UCF, Full Sail, Rollins, Valencia East, Orlando International Airport, and downtown Orlando! The monthly HOA covers many exterior maintenance items so you can enjoy low-maintenance living.This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

7471 Canford Court Unit 19, Winter Park

$185,000
2 Beds 3 Baths Hidden Oaks Condo Ph 10 SubDv. 32792 Zip Code
This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!

7450 Wynnewood Square Unit 189, Winter Park

$185,000
2 Beds 2 Baths Wrenwood Condo SubDv. 32792 Zip Code
Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown ceilings, and a functional floor plan designed for comfortable everyday living. All kitchen appliances are included, making your transition even easier. The end-unit location provides additional privacy and natural light while offering pleasant views of the community pool. Built with solid concrete block construction, this condominium offers durability and low-maintenance ownership. The bathrooms could benefit from updating, providing the perfect opportunity for the next owner to customize the home to their own taste and preferences. Whether you're a first-time homebuyer, downsizing, looking for a seasonal residence, or seeking an investment property, this home offers tremendous potential and value. Wrenwood Condominium allows up to two pets, with a maximum weight of 25 pounds each, making it a great option for pet lovers. Conveniently located near shopping, dining, entertainment, major highways, and everything Winter Park and the greater Orlando area have to offer. Don't miss this opportunity to own an affordable Winter Park condominium and create the home you've always envisioned.

4756 Tangerine Avenue Unit 4756, Winter Park

$180,000
2 Beds 2 Baths Parkview Village SubDv. 32792 Zip Code
PRICE IMPROVEMENT! TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax and enjoy the Florida weather. The kitchen comes complete with stainless steel appliances, ample cabinet and counter space, and a convenient pass-through opening overlooking the main living area for easy entertaining. Both bedrooms are generously sized with similar layouts, while the two full bathrooms provide everyday comfort and convenience. The interior laundry space adds functionality to the home. Located in Parkview Village Condominium, residents can enjoy community amenities including a clubhouse, community pool, gazebo, and more. This well-maintained community is surrounded by mature trees and landscaping and offers a prime location just minutes from Downtown Winter Park, Full Sail University, UCF, shopping, dining, entertainment, and major roadways including 417 and 436. Whether you’re looking for a primary residence, seasonal getaway, or investment opportunity, this centrally located condo offers comfort, convenience, and low-maintenance living.

2923 Antique Oaks Circle Unit 34, Winter Park

$172,000
2 Beds 2 Baths Hidden Oaks Condo Ph 7 SubDv. 32792 Zip Code
Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new interior paint and new blinds throughout, and all appliances are included for added convenience. Step through the sliding glass doors off the kitchen to enjoy a private fenced patio, complete with an additional exterior storage room — perfect for extra storage space or outdoor essentials. Upstairs, you’ll find comfortable carpet flooring throughout, including a generously sized primary bedroom with a large closet, as well as a spacious guest bedroom with ample closet space. Residents of Hidden Oaks Condominium enjoy access to excellent community amenities, including a sparkling community pool and a fenced playground area. The monthly HOA fee includes water and trash services. Ideally located near Full Sail University, University of Central Florida, and Valencia College, with convenient access to shopping, dining, Downtown Orlando, Downtown Winter Park, FL-408, and FL-417. This move-in ready home offers comfort, convenience, and an excellent location. Schedule your private showing today — this opportunity won’t last long!

3243 Forest Oaks Court Unit 117, Winter Park

$164,999
1 Beds 1 Baths Four Seasons Condo SubDv. 32792 Zip Code
Excellent opportunity in the heart of Central Florida! Welcome to this charming 1-bedroom, 1-full-bath condominium located in the desirable Four Seasons Condominiums of Winter Park. Step inside to a spacious living area that flows seamlessly into the dining and kitchen spaces, creating a comfortable and functional layout perfect for everyday living or entertaining. The primary bedroom features a large walk-in closet, offering comfort and convenience. Relax and enjoy the view from the oversized private balcony just off the living room. Ideally situated just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, shopping, and dining, this location truly offers convenience at every turn. Enjoy being only minutes from the renowned Park Avenue, local museums, and everything Winter Park has to offer. Four Seasons Condominiums is a beautifully maintained 20-acre community within the Winter Park city limits and located in a highly sought-after school district. Residents enjoy an array of amenities including three swimming pools, tennis courts, shuffleboard courts, laundry facilities, and a clubhouse with a library. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo is a must-see!

200 Saint Andrews Boulevard Unit 704, Winter Park

$159,000
2 Beds 3 Baths Colonies SubDv. 32792 Zip Code
Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor features durable and stylish vinyl flooring for added comfort. The fully renovated bathrooms boast contemporary designs and quality craftsmanship, and a brand-new AC system ensures year-round efficiency and peace of mind. Natural light pours into every corner of the home, enhancing the open layout and highlighting the elegant upgrades. Ideally located just minutes from shopping, dining, and top-rated schools, this condo offers both luxury living and everyday convenience. Don’t miss the opportunity to own this move-in-ready gem in a prime location!

7300 Daniel Webster Drive Unit M7, Winter Park

$159,000
2 Beds 3 Baths Colonies SubDv. 32792 Zip Code
Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll find stylish and low-maintenance vinyl flooring throughout, adding warmth and continuity to the private living quarters. The fully renovated bathrooms boast contemporary finishes and fixtures, delivering a fresh, spa-like feel. A brand-new AC system ensures year-round comfort and energy efficiency. With its modern upgrades, functional layout, and move-in-ready condition, this condo is a perfect choice for buyers seeking both style and convenience.

3027 Aaron Burr Avenue Unit L1, Winter Park

$144,000
1 Beds 1 Baths Stratford Winter Park SubDv. 32792 Zip Code
One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new screened porch, and new toilet — giving you move-in-ready comfort and peace of mind. The kitchen comes fully equipped with range, dishwasher, refrigerator, and microwave. A stackable washer and dryer are conveniently located in the bedroom, and an additional community laundry room with two washers and dryers is available free of charge. Stratford residents enjoy an amenity-rich lifestyle including: • Two sparkling pools • Tennis courts • 24/7 fitness center • Clubhouse available for private gatherings • Pet station *Planned social events for residents. The HOA adds tremendous value by covering water, trash removal, internet, pest control, exterior maintenance, grounds care, and common areas — simplifying ownership and monthly budgeting. Located in a prime Winter Park area with easy access to 408, Semoran Blvd., 417, I-4, and State Road 50. Just minutes from shopping, dining, grocery stores, and within 20 minutes of UCF, Full Sail University, Rollins College, and Park Avenue. With its thoughtful updates, first-floor convenience, and exceptional community amenities, this condo offers more than just a home — it delivers an above-average lifestyle in one of Central Florida’s most desirable locations.

291 Lewfield Circle Unit 291, Winter Park

$139,500
1 Beds 1 Baths Parkview Village SubDv. 32792 Zip Code
PRICE IMPROVEMENT!! What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, a student prioritizing location and community or a loving and supportive parent wanting to be closer to your excelling child, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. Directly across from Full Sail University, minutes to Rollins College, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, biking, hiking, swimming, volleyball, pickleball, tennis and painting at The Crealde School of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together or get you owning immediately. Let's get your private tour scheduled.

3019 Antique Oaks Circle Unit 124, Winter Park

$138,000
1 Beds 1 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 408, Winter Park

$138,000
1 Beds 1 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 404, Winter Park

$138,000
1 Beds 1 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 306, Winter Park

$129,000
1 Beds 1 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting space for everyday living and entertaining. A set of French doors leads to the screened-in porch, providing the perfect spot to enjoy your morning coffee or unwind after a long day. The spacious bedroom features a large walk-in closet, offering plenty of storage. This condo also includes one assigned parking space, along with additional guest parking for visitors. Residents enjoy access to a community pool and onsite laundry facilities, adding to the convenience of low-maintenance living. Ideally located just minutes from SR 408, the University of Central Florida (UCF), shopping, dining, restaurants, and entertainment, this condo offers an unbeatable combination of comfort, convenience, and value. Whether you're searching for a primary residence or a smart investment opportunity in a high-demand area, this Central Florida gem is one you won't want to miss!

1000 S Semoran Boulevard Unit 305, Winter Park

$115,000
1 Beds 1 Baths Golfside Villas Condo SubDv. 32792 Zip Code
Virtually Staged. ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an oversized bedroom, and a large bathroom. The charming kitchen offers ample cabinet and counter space, creating an inviting space for both everyday living and entertaining. Step outside to your private balcony, the perfect place to enjoy your morning coffee or relax at the end of the day. The home's separate exterior entrance adds an extra level of convenience and privacy. Enjoy low-maintenance living with HOA dues that cover water, trash, exterior maintenance, and roof replacement. The community recently completed a roof replacement, providing added peace of mind for the new owner. Residents also enjoy access to the community pool, perfect for cooling off on warm Florida days. Conveniently located near UCF, Valencia College, Waterford Lakes Town Center, Orlando International Airport, major highways including SR 408 and SR 417, shopping, dining, and entertainment, this home is also zoned for highly desirable schools. Whether you're a first-time homebuyer, someone looking to downsize, or an investor seeking a well-maintained property in a prime East Orlando location, this condominium offers an outstanding opportunity. Schedule your private showing today!

1000 S Semoran Boulevard Unit 302, Winter Park

$109,500
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 is leased to a reliable long-term tenant paying $1,450 / month. 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

$89,900
1 Baths Colonies SubDv. 32792 Zip Code
NEW PRICE!!! 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