Location: Winter Park
Do Not Show Listings
1500 GAY RD #8D, WINTER PARK, FL 32789
$267,00019 Days on yellowkey MLS ID: O6392693
0 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972Monthly Fee: $425 Tax: $2,630 (2025)Community: Chateaux Du LacCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,630
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to the most beautifully updated 2 Bedroom 2 bath End Unit in a Lakefront Community on Lake Killarney. This home features Quartz counter tops with a Granite Island and stainless steel appliances, along with a beverage refrigerator, and luxury vinyl flooring through out the whole unit. A huge living room offers loads of gathering and entertaining space in this cheerful home. Enjoy Florida outdoor living in the private patio. Home is move in ready!! The Community includes a private Boat Ramp and Dock, On-site Boat Parking, Heated Pool and Sauna, and a community grill. Enjoy Sunsets on Lakefront Deck and short walking access to Winter Parks Shops, Restaurants, Movies, Park Avenue, Farmers Market and Downtown Art Festivals. Come see this inviting home and make it yours today!
Listing is courtesy of: SOLID OAK REAL ESTATE LLC (321-888-9232)
Listing Agent: Trevor Laug (321-888-9232)
1500 GAY RD #24B, WINTER PARK, FL 32789
$261,500196 Days on yellowkey MLS ID: O6348568
REDUCED by $2,500 (0.9%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $1,271 (2024)Community: Chateaux Du LacSpa: NoCondo
Taxes:$1,271
Tax Year: 2024
Remarks: ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS! Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas! Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting, Kitchen Island/Bar! Enjoy the Ease of Luxury Vinyl Plank Flooring, Crown and Wide Floor Moldings, Plantation Shutters, Upgraded Energy Saving Windows and Sliding Glass Door. Modernized Master Bath with Raised Vanity, Open Layout with Spacious Shower with Seat and Barn Door for Privacy. Guest Bath also Updated with New Raised Vanity and Shower. Second Bedroom Walk-in Organized Closet. New Master Bedroom Carpet in 2025, New Water Heater in 8/2025 A/C replaced 4-5 years ago. Sit on Private Covered Patio and enjoy Pool Views and Landscaped Vistas. Walk to Shopping, Restaurants, Movies, Trader Joe's. Minutes from Park Avenue and Farmer's Market. Centrally located, close to I-4. One of Winter Park's "Best Kept Secrets"! Make an Appointment to view today!
Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)
Listing Agent: Janice Erickson (407-621-6856)
640 N PARK AVE #5, WINTER PARK, FL 32789
$450,000117 Days on yellowkey MLS ID: O6367841
0 Days Off yellowkey (back on 4/13/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 673 Built: 1956Monthly Fee: $812 Tax: $4,623 (2024)Community: Park Aire CondoCondo
Taxes:$4,623
Elementary School: Lakemont Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.
Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)
Listing Agent: David Auerbach (407-619-5250)
300 CAROLINA AVE #207, WINTER PARK, FL 32789
$495,00026 Days on yellowkey MLS ID: O6391523
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1981 Tax: $6,512 (2025)Community: Park West CondoCondo
Taxes:$6,512
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: One or more photo(s) has been virtually staged. Enjoy the best of downtown Winter Park living in this spacious 1-bedroom, 2-bathroom condominium located in the highly sought-after Park West Condominiums. This well designed residence offers comfortable living with the rare convenience of two full bathrooms. Park West is a gated community known for its exceptional amenities, including a resort-style swimming pool, lighted tennis courts, and a clubhouse perfect for social gatherings and private events. Residents also benefit from secure entry, covered parking, and beautifully maintained grounds, creating a quiet and private residential setting just moments from the heart of the city. One of the community’s most desirable features is its unbeatable proximity to Park Avenue. Just a short walk away, you’ll find Winter Park’s premier destination for boutique shopping, award-winning restaurants, cafés, art galleries, Central Park, Rollins College, and the weekly farmers market. Whether you’re enjoying a casual coffee, fine dining, or cultural events, everything downtown Winter Park has to offer is right at your doorstep. This condominium combines location, convenience, and lifestyle amenities, making it an ideal opportunity for full-time residents or those seeking a low-maintenance home in one of Central Florida’s most prestigious neighborhoods.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kevin Mcclanahan (407-491-8509)
1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792
$174,70024 Days on yellowkey MLS ID: O6392099
REDUCED by $5,000 (2.8%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1969Monthly Fee: $355 Tax: $1,111 (2025)Community: Golfside Villas CondoCondo
Taxes:$1,111
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy access to shopping, dining, and major roadways. One of the few units in the community featuring a screened patio AND an in-unit washer and dryer, providing added convenience and everyday ease. Low HOA fees make this an excellent opportunity for both homeowners and investors alike. Whether you're looking for a primary residence or an income-producing property, this condo stands out with its upgrades, location, and unique features. NEW ROOF April 2026! Call today to schedule your private showing.
Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)
Listing Agent: Carrie Sue Shawfield (407-963-7749)
1695 LEE RD #E103, WINTER PARK, FL 32789
$139,99018 Days on yellowkey MLS ID: S5146352
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966Monthly Fee: $482 Tax: $2,041 (2025)Community: Waterfall CoveCondo
Taxes:$2,041
Elementary School: Hungerford Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a bright and spacious living area, perfect for relaxing or entertaining guests. The kitchen features modern new (2025) appliances and ample storage space, making cooking a breeze. The bedrooms are spacious and plenty of natural light, creating a peaceful ambiance. One of the highlights of living at Waterfall Cove is the stunning waterfall feature that gives the community its name. This serene setting is perfect for unwinding after a long day or enjoying a peaceful morning coffee. The community also features a pool and fitness center, providing residents with plenty of opportunities to stay active and healthy. Waterfall Cove is ideally located near Interstate 4, making it easy to commute to major job centers in Orlando. It's also just a short drive away from downtown Orlando and Winter Park, where you can explore a variety of dining, shopping, and entertainment options. Additionally, the condo is close to Rollins College, making it a great option for convenient housing. For those who enjoy the outdoors, Waterfall Cove is close to several parks and nature reserves, where you can hike, bike, or simply enjoy the beauty of the Florida landscape. And if you're a coffee lover, you'll appreciate the proximity to Starbucks, where you can grab your favorite drink on the go. In conclusion, Waterfall Cove offers the perfect blend of comfort, convenience, and natural beauty. With its modern amenities, convenient location, and affordable pricing, it's no wonder why living in this area is so desirable. Don't miss out on the opportunity to make Waterfall Cove your new home! THIS PROPERTY MAY QUALIFY FOR UP TO 40,000.00 IN DOWN PAYMENT ASSISTANCE.
Listing is courtesy of: RE/MAX SELECT GROUP (954-905-2772)
Listing Agent: Jason Price (954-905-2772)
106 S INTERLACHEN AVE #118, WINTER PARK, FL 32789
$1,395,00067 Days on yellowkey MLS ID: O6380506
REDUCED by $55,000 (3.8%) on 04/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1834 Built: 1971 Tax: $9,767 (2025)Community: Cloisters CondoCondo
Taxes:$9,767
Remarks: Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique shopping, fine dining and cultural landmarks. Designed for elegant everyday living and entertaining, the open floor plan showcases a chef’s kitchen with granite countertops, solid wood cabinetry, and an island for prep and serving. The spacious dining and living areas are enhanced by hardwood flooring, crown molding and a marble-trimmed wood-burning fireplace. More than 20 feet of sliding glass doors open to an expansive, L-shaped terrace that brings in natural light and offers breathtaking lake vistas. The oversized primary suite offers serene lake views and includes an en-suite bath with dual vanities, built-in closets and a walk-in shower. Additional features include a rare laundry and utility room with a full-size washer, dryer and sink, updated electrical and plumbing, and upgraded water heater and HVAC system. Just two blocks from Park Avenue, this residence places you in the heart of downtown Winter Park’s sought-after lifestyle. Enjoy effortless access to fine dining, boutique shopping, world-class museums, Rollins College and year-round cultural events, all in an accessible, lakefront setting. Whether going to the Saturday farmers market, dining alfresco along the avenue or taking in the scenic views of Lake Osceola from your private residence, this property offers a seamless blend of luxury and urban elegance.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Drew Henner (407-406-0662)
311 E MORSE BLVD #7-19, WINTER PARK, FL 32789
$299,900106 Days on yellowkey MLS ID: O6368912
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 482 Built: 1960Monthly Fee: $870 Tax: $3,161 (2024)Community: Whispering WatersCondo
Taxes:$3,161
Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you within effortless reach of the Winter Park Farmers’ Market, acclaimed dining, boutique shopping, cultural venues, and a picturesque network of lakes and parks. The residence features a bright and open floor plan where the kitchen, dining, and living spaces flow seamlessly, creating an inviting atmosphere ideal for both everyday living and entertaining. Upon entry, you are welcomed by multiple storage closets and a discreet hallway that provides additional storage and convenient access to the full bathroom—an uncommon luxury for a studio-style layout. Sliding glass doors lead to a generously sized, private covered and enclosed balcony overlooking the tranquil interior courtyard, with peaceful views of the community pool and Lake Osceola beyond. This serene outdoor retreat is the perfect setting for morning coffee, evening relaxation, or quiet reflection amid lush surroundings. Residents enjoy a truly low-maintenance lifestyle, with electric, gas, water, sewer, and trash all included in the condominium fee. Building amenities include elevator access to the third floor, on-site management, a community laundry facility, and beautifully appointed common areas. The property also features expansive outdoor patios overlooking Lake Osceola, a resident club room, and immediate access to the community pool. Located within Whispering Waters, a highly desirable 55+ community, this residence is ideally suited as a primary home, seasonal retreat, or elegant in-law suite—offering timeless Winter Park living with unmatched convenience and charm.
Listing is courtesy of: TURN-KEY MOVES REALTY (407-796-2221)
Listing Agent: Mathew Kelly (407-796-2221)
3021 AARON BURR AVE #3, WINTER PARK, FL 32792
$140,0001 Day on yellowkey MLS ID: S5147382
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1090 Built: 1974Monthly Fee: $479 Tax: $1,992 (2025)Community: ColoniesCondo
Taxes:$1,992
Elementary School: Cheney Elem
Remarks: Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Daiana Garcia Medrano (321-315-4686)
851 MILES AVE #13, WINTER PARK, FL 32789
$209,999117 Days on yellowkey MLS ID: O6368234
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 808 Built: 1984 Tax: $2,694 (2025)Community: Aragon CondoCondo
Taxes:$2,694
Remarks: Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready. As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to maintain. The heart of the home, the kitchen, has been completely reimagined with sleek granite countertops, fresh cabinetry, and contemporary finishes that make cooking and entertaining a joy. The bathroom has also received a full renovation, featuring granite countertops and updated fixtures that enhance both style and function. With thoughtful design at every turn, this condo feels fresh, bright, and uniquely yours. Situated on the second floor for added privacy and natural light, this unit provides a peaceful retreat while still being close to all that Winter Park has to offer. Enjoy being minutes from Park Avenue, with its array of boutique shopping, acclaimed restaurants, art galleries, and outdoor markets. Explore scenic parks, lakeside boat tours, cultural attractions, and community events that make Winter Park one of Central Florida’s most desirable places to live. Whether you’re searching for your next home or an exceptional investment opportunity, 851 Miles Ave #13 showcases stylish updates, quality finishes, and a location you’ll love. Don’t miss your chance — schedule a showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eric Campbell (321-279-8941)
7336 FOREST HILL CT #240, WINTER PARK, FL 32792
$169,90046 Days on yellowkey MLS ID: O6386461
REDUCED by $10,000 (5.6%) on 04/08/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1984Monthly Fee: $450 Tax: $2,899 (2025)Community: Hidden Oaks Condo Ph 12Condo
Taxes:$2,899
Remarks: Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained END unit is move in ready: two-story 2 Bedrooms 1.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area. Updated cabinetry, quartz counters, stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, two bedrooms and master bathroom with double vanity set and brown glass sink top in dark coffee. Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
256 LEWFIELD CIR #256, WINTER PARK, FL 32792
$184,90093 Days on yellowkey MLS ID: O6367842
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973Monthly Fee: $465 Tax: $1,916 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$1,916
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to a covered and screened rear porch with a pool view. The primary suite features a walk-in closet and a private bath with a floor-to-ceiling tiled walk-in shower. The HOA completed roofing and plumbing improvements in 2019, and all exterior and grounds maintenance is handled by the on-site HOA. The Stratford community offers two pools, a community and fitness center, and tennis courts. Just minutes from popular Downtown Winter Park with its dining and shopping, with easy highway access via the 417 and I-4, and surrounded by nearby lakes and parks, this is one opportunity you don’t want to miss. Call today to schedule your private tour!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Renee Kumar Llc (407-756-4422)
200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792
$225,00012 Days on yellowkey MLS ID: O6395720
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1266 Built: 1970Monthly Fee: $451 Tax: $2,131 (2025)Community: Four Seasons CondoCondo
Taxes:$2,131
Elementary School: Brookshire Elem
Remarks: Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
151 N ORLANDO AVE ##115, WINTER PARK, FL 32789
$298,000133 Days on yellowkey MLS ID: O6362403
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 710 Built: 1960 Tax: $2,965 (2025)Community: Lake Killarney CondoSpa: NoCondo
Taxes:$2,965
Elementary School: Killarney Elem
Remarks: Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
101 S NEW YORK AVE #302, WINTER PARK, FL 32789
$1,580,00020 Days on yellowkey MLS ID: O6390752
REDUCED by $50,000 (3.1%) on 04/11/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3174 Built: 2009Monthly Fee: $1,263 Tax: $19,802 (2025)Community: Winter Park ResidentialCondo
Taxes:$19,802
Remarks: Discover unparalleled luxury at The Douglas Grand, a distinguished location just a stone’s throw from Park Ave in Downtown Winter Park. This expansive 2-Story unit boasts 3,174 sq/ft of living space with your private elevator. From the moment you step inside, you’ll be captivated by the exquisite craftmanship and modern comforts that define this exceptional residence. This stunning condo boast three spacious ensuite bedrooms and abundance of storage. The heart of this home is the gourmet kitchen, custom-designed and built to fulfill every chef's dream complemented by top-of-the-line appliances that include a wall-mounted convection/microwave oven and a cutting-edge Wolfe induction stove top. The kitchen is not only functional but also perfect for entertaining, featuring a spacious breakfast bar where culinary creativity knows no bounds. As you move through this exceptional residence, in the living room, dining room, and entrance, creating an inviting ambiance that welcomes you home. Indulge in the spa-like sanctuary of the master bathroom, where luxury knows no bounds with a charming fireplace in the primary suite. Here, you'll find a sumptuous bathtub, separate vanity areas. With three generously appointed bedrooms, featuring custom closets, you'll have ample space to organize your wardrobe and storage needs effortlessly. Step onto the private balcony upstairs and be captivated by the breathtaking views. This secluded outdoor space is an ideal setting for unwinding with an evening cocktail, savoring a family dinner, or starting your day with a tranquil cup of morning coffee. The Douglas Grand enjoys a central location that places you within a lifestyle that defines this charming community. In addition to its unmatched location, this building offers a quiet, private, and secure environment—making it the perfect choice for those seeking a "lock and leave" second home or a luxurious vacation retreat. Don't miss this opportunity to experience the height of elegance and y reach of Downtown Winter Park's award-winning restaurants, cultural museums, upscale shopping boutiques, and the vibrant sophistication. Contact me today to schedule a private viewing of this remarkable residence.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Julie Scott (407-497-3492)
302 LEWFIELD CIR #302, WINTER PARK, FL 32792
$146,00068 Days on yellowkey MLS ID: O6380160
REDUCED by $4,000 (2.7%) on 04/11/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $350 Tax: $1,942 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$1,942
Remarks: Perfectly positioned in the heart of Winter Park, this inviting one-bedroom, one-bath residence offers effortless living in one of Central Florida’s most desirable locations. The thoughtfully designed interior opens to a second-story private balcony, creating a quiet space to unwind or enjoy morning coffee. Natural light fills the home, while the layout provides comfort, functionality, and easy everyday living. Residents enjoy access to a community pool and clubhouse, ideal for relaxation and gathering, all within a well-maintained setting. Just moments from Park Avenue, Rollins College, shopping, dining, and scenic parks, this condo places the best of Winter Park right outside your door. An exceptional opportunity for those seeking location, lifestyle, and simplicity in a prime Winter Park community.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Heather Spirazza (407-757-6022)
4864 TANGERINE AVE #4864, WINTER PARK, FL 32792
$200,00056 Days on yellowkey MLS ID: O6383320
INCREASED by $1,000 (0.5%) on 04/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1059 Built: 1973Monthly Fee: $441 Tax: $2,828 (2025)Community: Wrenwood CondoCondo
Taxes:$2,828
Remarks: One or more photo(s) has been virtually staged. 4.99% INTEREST RATE OFFERED FOR QUALIFIED BUYERS! This low-maintenance Winter Park condo just became even more affordable ... and it truly checks all the boxes! Enjoy single-story living with no neighbors above or below, corner-unit privacy, a screened patio overlooking the spacious courtyard, updated kitchen and baths, and major mechanical updates already taken care of. Add in a community pool, sidewalks, pet stations, and an unbeatable Winter Park location - and this 2-bedroom, 2-bath condo offers the ideal combination of comfort, convenience, privacy, and value. Inside, you’ll find a functional split-bedroom floor plan, spacious living and dining areas, indoor laundry, and a screened patio that adds valuable outdoor living space. The one-story layout offers easy everyday living, while the corner-unit location provides added privacy and a more desirable setting within the community. The flexible floor plan works well for everyday living, guests, roommates, or even a home office setup. Located in a community with a pool and situated near shopping, dining, major roadways, and daily conveniences, this property offers easy access to University of Central Florida, Full Sail University, SR-417, FL-436, Downtown Winter Park, and Downtown Orlando. Whether you are searching for a primary residence, a first home, or a low-maintenance property in a central location, this home checks all the boxes. The special financing rate equates to a savings of approximately $213 per month for qualified buyers! Now more than ever, if you’ve been searching for an affordable, easy-maintenance, Move-in Ready property in Winter Park ... this is your sign! Seller offering an incredible savings to help you on your path to homeownership. Terms and conditions apply. Call for details.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Allison Day (407-617-2881)
1695 LEE RD #C202, WINTER PARK, FL 32789
$210,000406 Days on yellowkey MLS ID: O6285607
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966 Tax: $2,126 (2024)Community: Waterfall Cove At Winter ParkCondo
Taxes:$2,126
Remarks: This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.
Listing is courtesy of: PRIMESTATE REALTY, INC. (407-850-9494)
Listing Agent: Hoover Yap (407-342-9395)
1695 LEE RD #D211, WINTER PARK, FL 32789
$115,0006 Days on yellowkey MLS ID: O6396190
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966 Tax: $2,051 (2025)Community: Waterfall Cove/Winter ParkCondo
Taxes:$2,051
Remarks: Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area of Winter Park close to tons of and amenities. Currently being rented for $1550/month
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Brandy Ray (949-449-5652)
1695 LEE RD #E204, WINTER PARK, FL 32789
$115,000125 Days on yellowkey MLS ID: O6366205
REDUCED by $9,900 (7.9%) on 04/03/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 881 Built: 1966Monthly Fee: $482 Tax: $1,917 (2024)Community: Waterfall CoveCondo
Taxes:$1,917
Remarks: Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area with lots of nearby shopping, restaurants, and amenities
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