Location: Winter Park
Do Not Show Listings
311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792
$109,500277 Days on yellowkey MLS ID: O6355536
REDUCED by $400 (0.4%) on 06/29/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 785 Built: 1974Monthly Fee: $880 Tax: $1,271 (2024)Community: Winter Park Woods CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,271
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: 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.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Omar Rodriguez (321-442-2001)
1134 WASHINGTON AVE #13C, WINTER PARK, FL 32789
$525,00013 Days on yellowkey MLS ID: O6416746
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2195 Built: 1981 Tax: $7,472 (2025)Community: Quarters At Winter Park CondoCondo
Taxes:$7,472
Elementary School: Audubon Park K8
High School: Winter Park High
Tax Year: 2025
Middle School: Audubon Park K-8
Remarks: Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Drew Henner (407-406-0662)
1600 ALABAMA DR #402, WINTER PARK, FL 32789
$1,250,00056 Days on yellowkey MLS ID: O6413153
0 Days Off yellowkey (back on 7/22/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1574 Built: 1981 Tax: $4,206 (2025)Community: Alabama CondoCondo
Taxes:$4,206
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Nestled along one of Winter Park's most cherished brick-lined streets, this elegantly appointed two-bedroom, two-bath residence at the prestigious Alabama offers a rare opportunity to experience the very best of lakeside luxury living. With 1,574 square feet of thoughtfully designed interior space, this exceptional unit captures the timeless charm and sophistication that have made the Alabama one of the most coveted addresses in the heart of Winter Park. From the moment you step through the gracious foyer entry, complete with a coat closet, you are welcomed by an atmosphere of warmth and refined taste. Reclaimed wood floors flow seamlessly throughout the entire residence, lending an organic richness that perfectly complements the grass cloth covered walls and classic crown molding found in every room. Recessed lighting adds a soft, curated ambiance, while the expansive living and dining area serves as the heart of the home, offering sweeping views of the beautifully maintained gardens and the shimmering waters of Lake Maitland just beyond. The well-appointed kitchen is a chef's delight, featuring stainless steel appliances, an induction range, a Subzero refrigerator, stone countertops, a charming penny tile backsplash, and a central island ideal for both casual dining and entertaining. A dedicated interior laundry room adds a layer of everyday convenience that is rarely found in residences of this era and character. The primary bedroom is a true retreat, featuring double built-in closets and a beautifully finished en suite bath with a walk-in shower. The second bedroom is comfortably proportioned and well-suited for guests, a home office, or whatever lifestyle demands require. The hall bath offers a classic tub and shower combination to serve residents and visitors alike. One reserved covered parking space is included, and monthly HOA dues of $1,600 cover the care and maintenance that keep this distinguished property in impeccable condition. The location is simply unmatched. Kraft Azalea Park, one of Central Florida's most scenic and beloved green spaces along the shores of Lake Maitland, is just moments away, offering a tranquil setting for morning walks and golden-hour evenings. The legendary shops, restaurants, and galleries of Park Avenue are easily accessible, placing world-class dining and boutique retail practically at your doorstep. Tennis enthusiasts will appreciate the proximity to the Winter Park Racquet Club, while golf aficionados will find the storied Interlachen Country Club well within reach, rounding out a lifestyle that is as active as it is refined. This is Winter Park living at its most authentic, offering history, elegance, and an unbeatable sense of place in one of the most desirable communities in all of Central Florida.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792
$80,00016 Days on yellowkey MLS ID: O6424619
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1974 Tax: $1,392 (2025)Community: Winter Park Woods CondoCondo
Taxes:$1,392
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Lisa Wright (321-231-3141)
2500 LEE RD #208, WINTER PARK, FL 32789
$175,000474 Days on yellowkey MLS ID: O6297570
0 Days Off yellowkey (back on 7/21/2026)
REDUCED by $5,000 (2.8%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $432 Tax: $1,519 (2025)Community: Lakeside Manor Apts CondoCondo
Taxes:$1,519
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Debbie Jones (407-619-1850)
262 LEWFIELD CIR #262, WINTER PARK, FL 32792
$149,50083 Days on yellowkey MLS ID: C7525448
REDUCED by $3,400 (2.2%) on 07/21/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $1,278 (2024)Community: Stratford A Winter Park CondoSpa: NoCondo
Taxes:$1,278
Remarks: Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower fixtures in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is everything and this one delivers. Just minutes from downtown Winter Park, grocery stores, shopping and dining with access to I-4, 408,417, Semoran Blvd and State Road 50. Only 10 minutes to Full Sail, 20 minutes to UCF and close to Rollins College.
Listing is courtesy of: KELLER WILLIAMS REALTY FT MYER (239-236-4350)
Listing Agent: Andrew Bishop (863-381-1870)
1500 GAY RD #3C, WINTER PARK, FL 32789
$244,90041 Days on yellowkey MLS ID: O6417533
REDUCED by $3,100 (1.3%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972Monthly Fee: $425 Tax: $3,244 (2025)Community: Chateaux Du LacCondo
Taxes:$3,244
Remarks: New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Heather Frazee (321-689-9465)
3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792
$179,90034 Days on yellowkey MLS ID: O6419959
0 Days Off yellowkey (back on 7/20/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984 Tax: $197 (2025)Community: Hidden. OaksSpa: NoCondo
Taxes:$197
Elementary School: Aloma Elem
Remarks: Under contract-accepting backup offers. Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
1695 LEE RD #E215, WINTER PARK, FL 32789
$135,000162 Days on yellowkey MLS ID: O6383089
REDUCED by $14,990 (10.0%) on 06/17/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966Monthly Fee: $624 Tax: $2,472 (2024)Community: Waterfall CoveCondo
Taxes:$2,472
Elementary School: Hungerford Elem
Remarks: Under contract-accepting backup offers. Located in the heart of Winter Park, this charming condo stands ready to welcome you home. This three-bedroom, two-bathroom sanctuary offers a blend of comfort and modern elegance, perfect for those who cherish both relaxation and entertaining. As you step inside, the spacious living and dining areas greet you with an abundance of natural light, creating a warm and inviting atmosphere. Imagine hosting friends and family in this expansive space, where laughter and memories will fill every corner. The heart of this home is undoubtedly the fully upgraded kitchen, featuring stunning quartz countertops, sleek new cabinets, and stainless steel appliances. Each meal becomes a culinary adventure in this thoughtfully designed area. Retreat to any of the large bedrooms, designed to be your personal oasis. Each room offers generous space, allowing for restful nights and peaceful mornings. A dedicated laundry room, complete with a washer and dryer, adds convenience to your daily routine, while ample storage throughout the unit ensures that everything has its place. Step outside onto your private balcony, where a serene courtyard unfolds below. Picture yourself sipping morning coffee or enjoying an evening breeze as you overlook the tranquil scene of benches, a sparkling pool, and a welcoming clubhouse—perfect for gathering with neighbors or unwinding after a busy day. This pet-friendly community understands that your fur babies deserve a home too, so bring them along for this new adventure! Plus, enjoy the benefits of the HOA, which includes cable TV and high-speed internet, making it easy to stay connected. With a prime location just a short walk from a variety of shopping and dining options, you’ll find everything you need right at your fingertips. And with quick access to I-4, the beautiful beaches and thrilling theme parks are just minutes away. This isn't just a condo; it’s a lifestyle filled with comfort, convenience, and community. Welcome to your new home in Winter Park! Schedule your private tour today.
Listing is courtesy of: FOWLKES REALTY CO (407-361-2052)
Listing Agent: Jenaia Fowlkes (407-361-2052)
3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792
$142,500341 Days on yellowkey MLS ID: O6337083
REDUCED by $2,000 (1.4%) on 07/10/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Monthly Fee: $300 Tax: $2,050 (2024)Community: Parkview VillageSpa: NoCondo
Taxes:$2,050
Remarks: 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.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cassandra Kelly Flores (347-723-4649)
291 LEWFIELD CIR #291, WINTER PARK, FL 32792
$144,000163 Days on yellowkey MLS ID: O6382547
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $350 Tax: $1,942 (2025)Community: Stratford Winter ParkCondo
Taxes:$1,942
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: 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.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Barbara Coy (407-497-1777)
700 MELROSE AVE #J24, WINTER PARK, FL 32789
$380,00068 Days on yellowkey MLS ID: R4911307
REDUCED by $10,000 (2.6%) on 07/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 987 Built: 1964 Tax: $3,874 (2025)Community: Winter Park Gardens CondoCondo
Taxes:$3,874
Remarks: Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally updated one bedroom unit has just been completed. All new paint, porcelain flooring, all new fixtures, bathroom, appliances, new wood cabinets, new stone counters. All NEW The desirable condo community of Winter Park Gardens is nestled between Mead Gardens, Azalea Tennis Center and upcoming Winter Park's Progress Point. Unit is located on the second floor but there is an elevator and stairs to help to the location. Spacious 2 bedroom , 2 bath unit has large open floor plan. Main living area has an additional glass sunroom which provides additional space and breath-taking views of the beautifully landscaped and private courtyard. With its prime location in Winter Park, you'll have easy access to a many of the dining opportunities, shopping, and entertainment options. This is a 55+ community Whether you're strolling through the charming downtown area of Park Avenue or Hannibal Square or immersing yourself in the thriving arts and culture scene, with the Orlando Museum of Art right around the corner This property is centrally located to Downtown Orlando and Downtown Winter Park… no need to use the expressways! !THIS UNIT DOES NOT REQUIRE OWNER TO BE OVER 55+ furniture can convey with purchase.
Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)
Listing Agent: Scott Butts (321-239-8509)
2500 LEE RD #104, WINTER PARK, FL 32789
$254,90049 Days on yellowkey MLS ID: TB8517242
REDUCED by $5,099 (2.0%) on 07/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $431 Tax: $2,327 (2025)Community: Lakeside Manor Apts CondoSpa: NoCondo
Taxes:$2,327
Remarks: Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a light granite sink, and carefully selected high-end finishes, including antique brass hardware and faucet. Vinyl flooring creates a clean, cohesive look across the residence. Additional recent improvements include: Renovated primary shower featuring Italian porcelain tile and added storage shelving (2026) , Dining room chandelier and bedroom ceiling fans (2026), Fresh paint throughout (2026) Tankless water heater (2025) , New A/C system (2024), professionally serviced in June 2026, Renovated hallway bathroom and added storage shelving (2024). The floor plan offers a bright, open living space with two points of entry and an easy flow between the kitchen, dining, and living areas. Beyond the unit itself, residents enjoy an exceptional list of community amenities. The HOA includes water, trash, Spectrum high-speed internet, cable television with 150+ channels, and access to popular streaming services including Disney+, HBO Max, Peacock, and more. Set along scenic Lake Killarney, the community features a private dock, water access for boating and kayaking, a peaceful courtyard, abundant guest parking, and newly completed landscaping enhancements. The association has also recently completed significant infrastructure improvements to the community's incoming water system, with paving improvements and painting coming soon. A great opportunity to purchase a truly turnkey residence.
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)
Listing Agent: Stephen Hachey (813-863-3948)
2503 TAHOE CIR #2503, WINTER PARK, FL 32792
$250,000118 Days on yellowkey MLS ID: O6395130
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1981 Tax: $506 (2025)Community: Cedarwood Village 1Condo
Taxes:$506
Remarks: This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining and living room combo. The living room has 2 skylights and flows right into the delightful Florida room. The Florida room boasts wonderful built-in shelving and a glass door giving access to the backyard. The primary bedroom showcases wonderful built-in cabinets, 2 closets and an ensuite bathroom with a granite counter vanity. The primary bedroom also looks into the Florida room but can be shut off for privacy with a sliding door. The second bedroom is at the front of the home and has access to the guest bathroom with a granite counter vanity. Two assigned parking spaces are directly in front of the home. To top it all off, this home is in close proximity to several restaurants and shops and is an easy drive to downtown Winter Park.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Beth Logullo (772-633-0670)
311 E MORSE BLVD #7-11, WINTER PARK, FL 32789
$299,000336 Days on yellowkey MLS ID: O6337061
REDUCED by $10,900 (3.5%) on 05/24/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 570 Built: 1960 Tax: $668 (2024)Community: Phillips Circle RepCondo
Taxes:$668
Remarks: Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.
Listing Agent: Mary Colton (407-222-7388)
5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792
$275,000106 Days on yellowkey MLS ID: O6398856
REDUCED by $5,000 (1.8%) on 06/29/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984 Tax: $668 (2024)Community: Lazy Oaks CondoCondo
Elementary School: Eastbrook Elementary
Remarks: Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!
Listing Agent: Mindy Machock (407-461-1866)
4756 TANGERINE AVE #4756, WINTER PARK, FL 32792
$185,00042 Days on yellowkey MLS ID: R4911483
REDUCED by $10,000 (5.1%) on 07/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $2,244 (2025)Community: Wrenwood CondoSpa: NoCondo
Taxes:$2,244
Remarks: 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.
Listing is courtesy of: HOME BUYER HELPER REAL ESTATE LLC (407-342-2664)
Listing Agent: Ada Sanchez (407-342-2664)
3282 OAK LAKE PL #3282, WINTER PARK, FL 32792
$154,50090 Days on yellowkey MLS ID: O6403912
0 Days Off yellowkey (back on 7/17/2026)
REDUCED by $15,000 (8.8%) on 05/28/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1984 Tax: $2,899 (2025)Community: Hidden Oaks Condominium Association, IncCondo
Taxes:$2,899
Remarks: New Price! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your private patio, complete with additional outdoor storage. Bonus: Your HOA dues cover water and trash service! This Winter Park steal won’t last—schedule your showing today.
Listing is courtesy of: BUSBY REALTY LLC (407-529-6952)
Listing Agent: Chad Busby (407-529-6952)
1500 GAY RD #18D, WINTER PARK, FL 32789
$275,00023 Days on yellowkey MLS ID: O6422691
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $3,244 (2025)Community: Chateaux Du LacCondo
Remarks: Under contract-accepting backup offers. Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
2526 PASSAMONTE DR #10F, WINTER PARK, FL 32792
$335,00013 Days on yellowkey MLS ID: O6418710
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1790 Built: 2009Monthly Fee: $402 Tax: $4,769 (2025)Community: Via Lago/Hanging Moss CondoCondo
Taxes:$4,769
Remarks: Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.
Listing is courtesy of: LEGACY CORNERSTONE INC (407-674-5601)
Listing Agent: Kathi Thomas (407-674-5601)
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