Location: Winter Park
Do Not Show Listings
640 N PARK AVE #5, WINTER PARK, FL 32789
$450,000120 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,623
Elementary School: Lakemont Elem
High School: Winter Park High
Tax Year: 2024
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
$495,00029 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
Tax Year: 2025
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)
1695 LEE RD #E103, WINTER PARK, FL 32789
$139,99021 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
$1,395,00070 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
$299,900109 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
$140,0005 Days 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
Middle School: Glenridge Middle
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)
256 LEWFIELD CIR #256, WINTER PARK, FL 32792
$184,90096 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
$225,00015 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
$298,000136 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
$1,580,00023 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
Elementary School: None
Middle School: None
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
$146,00071 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)
1695 LEE RD #C202, WINTER PARK, FL 32789
$210,000409 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
High School: None
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
$115,0009 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
$115,000128 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
5180 LAZY OAKS DR #5180, WINTER PARK, FL 32792
$290,00016 Days on yellowkey MLS ID: O6395367
0 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984Monthly Fee: $277 Tax: $1,746 (2024)Community: Lazy Oaks CondoCondo
Taxes:$1,746
Elementary School: Eastbrook Elementary
Remarks: Welcome to your Florida retreat. Whether you’re searching for the perfect first home or looking to downsize into a low-maintenance lifestyle, this single-story end-unit villa offers the ideal blend of comfort, convenience, and charm. With only one shared wall, it lives and feels like a single-family home. The HOA handles all exterior maintenance—including the roof, which was replaced just a few years ago—keeping your upkeep minimal and your insurance costs impressively low. The seller has lovingly maintained this home for nearly a decade and completed a long list of high-quality updates, including: - Glass sliders replaced in 2018 - Water heater replaced in 2019 - AC replaced in 2024 - Garage door replaced in 2024 - Front entry storm door added in 2024 - All kitchen appliances replaced within the last 5 years If that’s not pride of ownership, what is? Inside, the kitchen features newer cabinets, quartz countertops, and updated lighting throughout the home. The seller also transformed the back patio into a screened-in oasis—your own private Florida getaway perfect for morning coffee or evening relaxation. Location is another major highlight. Situated in prestigious Winter Park and zoned for some of Seminole County’s top-rated schools, this home offers unbeatable convenience. You’re just minutes from major highways, shopping, dining, and everything Central Florida has to offer. Schedule your showing today and experience all the beautiful features this home provides.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Farzana Zalil (407-617-3258)
4768 TANGERINE AVE #4768, WINTER PARK, FL 32792
$185,00052 Days on yellowkey MLS ID: S5144503
REDUCED by $9,900 (5.1%) on 04/08/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1973Monthly Fee: $280 Tax: $1,479 (2024)Community: Wrenwood CondoCondo
Taxes:$1,479
Remarks: Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!
Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)
Listing Agent: Christopher Franqui (347-703-7008)
4790 TANGERINE AVE #4790, WINTER PARK, FL 32792
$194,99560 Days on yellowkey MLS ID: O6380539
REDUCED by $20,000 (9.3%) on 04/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $2,253 (2024)Community: Wrenwood CondoCondo
Taxes:$2,253
Remarks: Move right into this beautifully two-bedroom, two-bath condominium located in desirable East Winter Park. The thoughtfully designed floor plan offers two spacious bedrooms, and bathrooms—one featuring a tub and the other a shower—providing comfort and privacy. The light-filled great room showcases attractive laminate wood flooring and sliding glass doors that open to a private, screened-in porch overlooking a sunny, landscaped courtyard—perfect for relaxing. Recent upgrades include a new AC system (May 2021), a new roof (2022), exterior paint 2025, updated bathrooms, upgraded laminate wood flooring throughout. The primary bathroom has been enhanced with a luxurious walk-in shower featuring upgraded stone and tile finishes. This unit is quietly situated in a private location within the well-maintained Wrenwood Condominiums community, offering assigned parking directly in front of the unit and access to a sparkling community swimming pool. Ideally located in East Winter Park, this community offers easy access to Park Avenue shopping and dining, Winter Park Village, Full Sail University, and nearby parks and lakes. Enjoy a vibrant lifestyle with museums, farmers markets, scenic walking areas, and the renowned Winter Park Chain of Lakes just minutes away, all while remaining close to major roadways and downtown Orlando. Schedule your private showing today.
Listing is courtesy of: SUNSHINE BROKERAGE, LLC (407-509-7961)
Listing Agent: Sonny Manku (407-509-7961)
291 LEWFIELD CIR #291, WINTER PARK, FL 32792
$144,00060 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
Remarks: One of the best 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)
WINTER PARK, FL 32789
$257,00021 Days on yellowkey MLS ID: O6393932
1 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 959 Built: 1984Monthly Fee: $318 Tax: $3,011 (2025)Community: Sandlewood Creek Condo Ph 04Condo
Taxes:$3,011
Elementary School: Dommerich Elem
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to one of the most affordable opportunities to own in the highly sought-after Winter Park High School district. This well-maintained community is tucked into a beautiful setting and is extremely convenient to everything that makes Winter Park one of Central Florida's top lifestyle destinations. This end-unit two bedroom / two-and-a-half bath condo in Sandlewood Creek combines a hip retro-classic style with comfort, functionality, and peace of mind with a long list of recent improvements. Solid knotty-pine wood accent paneling is featured throughout and compliments the freshly painted walls in designer colors. The kitchen has been partially renovated and has a nice clean and modern vibe, complemented by granite countertops and updated bathrooms for a clean, modern feel. The roof was replaced in 2021. Major system upgrades include an A/C (2019) and a brand-new water heater (2026), while the entire interior has just been freshly painted, carpets professionally cleaned, and a final detailed cleaning completed—making this home truly move-in ready. Whether you're looking for a primary residence, a low-maintenance lifestyle, or a smart investment in one of Central Florida’s most consistently in-demand areas, this property checks all the boxes. Enjoy easy living in a quiet, established community just minutes from everything that makes Winter Park special—top-rated schools, dining, shopping, and parks. Pre-approved for FHA financing and recent updates that your insurance company will like - this is a rare opportunity in this market. Don't miss it!. Sellers have this priced to sell, so don't delay. Call today to make your appointment for your private viewing.
Listing is courtesy of: DERENTHAL REALTY (321-662-8014)
Listing Agent: Mike Derenthal (321-662-8014)
2500 LEE RD #229, WINTER PARK, FL 32789
$245,00077 Days on yellowkey MLS ID: O6377616
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969 Tax: $2,613 (2024)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,613
Remarks: DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood Cabinets, Corian Sink and Countertops, Stainless Steel Appliances and expanded Pass-through Opening/Bar to Dining Room. Spacious Living and Dining Rooms with Lakeview. French Doors to Second Bedroom/Office with closets. Master Bedroom with en-suite Bath. Beautiful Cork Floors installed in all Living Areas. Tile in Kitchen and Baths. Ventless Washer and Dryer installed in Unit. Newer Double-Paned Energy-Efficient Windows. Unit has been replumbed. approximately 5 years ago. A/C and Water Heater new in 2025. Electric Panel replaced in 2019. You will love this close-in Winter Park Lakefront Community with all it's amenities, including Boat Ramp, 12 Boat Slips with Docks available for Lease to Owners, Waterfront Gazebo, Pool and. Clubhouse. Close to Shopping, Restaurants, Movie Theaters, Trader Joe's, Downtown Winter Park and Farmer's Market. Easy Access to I-4. Don't miss another Sunset! Call for a Private showing today!
Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)
Listing Agent: Janice Erickson (407-621-6856)
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