Winter Park, FL Homes for Sale under $300,000

This charming 2-bedroom, 2-bathroom condo offers 1,295 square feet of comfortable single-level living, thoughtfully designed for easy living and entertaining. The open floor plan boasts a spacious, sunlit living area and a well-appointed kitchen, perfect for culinary creations. Both bedrooms are generously sized and provide privacy, each featuring its own en-suite bathroom for added convenience.

Jamie Vanosdol EXP REALTY LLC

Location, Location, Location! This highly sought-after two-bedroom, two-bath condo in Winter Park won’t last long! Ideally situated close to the University of Central Florida, it's a perfect investment opportunity for parents offering lower monthly payments compared to the high costs of on-campus housing.Upgrades made in 2020 include a new roof, air conditioning system, and enhanced attic

Travis Sorci DALTON WADE INC

Charming 2-Story Condo in the Heart of Winter ParkLocated in the highly sought-after city of Winter Park, this beautifully maintained 2-bedroom, 1.5-bath condo offers the perfect blend of comfort, convenience, and community living. Along with a dedicated covered carport parking space. Just minutes from Park Avenue, top-rated shopping, and dining destinations, this home puts you at the

Jessica Geer A+ REALTY PROFESSIONALS, INC

One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of

Eddie Cooper MAINFRAME REAL ESTATE

Excellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-bath corner unit is in the Four Seasons Condominiums of Winter Park, just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, and shopping. Park Avenue and museums are just minutes away. Four Seasons Condominiums is a 20-acre community located within the Winter Park city

Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

One or more photo(s) has been virtually staged. Welcome you to your charming 3-bedroom, 2-bathroom condo right in the heart of historic Winter Park! This spacious end unit spans 1,322 square feet and features beautiful designer touches that create a cozy and inviting atmosphere. Enjoy the stylish kitchen and baths along with a large primary bedroom that boasts an ensuite bathroom and a

Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

2/2 * 956 SQ FT * LAKE KILLARNEY * CLOSE TO PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NEW AC * NEW WATER HEATER * NEW INTERIOR PAINT * NEW LIGHTING *Perfectly located close to Park Ave in Winter Park, Rollins College, and Downtown Orlando. Fully updated, sought-after 956 Sq ft 2/2 Condo, on beautiful Lake Killarney a serene oasis in Winter

Alison Maltby THE ANDERSON GROUP & CO PL

Location, Location, Location! Welcome to this charming Winter Park townhome. The first floor features a convenient half bath and an in-unit laundry area. Upstairs, you’ll find two spacious primary suites, each with its own private bathroom. Enjoy outdoor living with a private back patio and take advantage of the community pool just steps away. Perfectly situated for comfort and lifestyle! Enjoy

Jasmin Cabral LIFESTYLE INTERNATIONAL REALTY

This stylish condo lives more like a townhouse, offering two stories, a private patio, and a fenced yard for added privacy and outdoor enjoyment.Inside, you’ll find an open floor plan with vaulted ceilings and a cozy wood-burning fireplace. The updated kitchen and bathrooms pair perfectly with ceramic tile and luxury vinyl flooring throughout—no carpet in sight! A versatile first-floor

Allison Day RE/MAX TOWN & COUNTRY REALTY

Don’t miss your opportunity to own this lovingly cared for home in beautiful Winter Park! This UPDATED 2-bedroom, 2-bath condo is just minutes from the vibrant downtown area with its boutique shopping, renowned restaurants, museums, colleges, boat tours, and more. Located on the first floor with NO STAIRS, this home offers numerous UPGRADES, including: energy-efficient double-pane windows and

Jim Chuba CHARLES RUTENBERG REALTY ORLANDO

Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as

Nicole Van Treese SUNDIAL REAL ESTATE LLC

Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own private bathroom.

Qing Lin SPRINGHILL PROPERTIES LLC

Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

Incredible Investment Opportunity in a Desirable Location!This 2-bedroom, 1.5-bath home is full of potential and ready for a transformation. It's a fantastic opportunity for investors, flippers, or anyone seeking a high-potential investment. With just a little TLC, this property can be turned into a beautiful primary residence or a strong income-producing rental. Whether you're looking to

Nimrah Ashraf THE FIRM RE

Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

Sue Gilman KELLER WILLIAMS WINTER PARK

**This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a

Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

Investors/builders, here is your next project. This oversized lot (6,957 sf) on a dead-end street is perfect for our next investment opportunity. With a Winter Park address, this lot contains a spectacular location. In the bustling area of College Park/Winter Park, this lot sits near the main campus of Advent Health, the museums of Orlando, shopping on Park Avenue, and fine dining at the new

Herb Baird, Jr MARKET CONNECT REALTY LLC

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 is included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to

Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESTLED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGERATOR AND

Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully

Michell Carrasquero GLOBALWIDE REALTY LLC

Winter Park gem! Tastefully updated 2-bedroom, 2-bathroom corner condominium with a spacious patio is your rare chance ! This one-of-a kind residence boasts high quality enhancements such as plantation shutters, built-in closets, hurricane proof sliding door, smart canned lighting in the living room, dining room, kitchen, and hallway, along with a smart fan with a light kit in

Irina Paul FUTURE HOME REALTY INC

Welcome to this 2-bedroom, 2-bathroom condo located in the desirable winter Park Villas community. Well-maintained with a fireplace. Plenty of natural light. The kitchen features newer cabinets and a breakfast bar. The master bedroom has generous space, a walk-in closet, and an en-suite bathroom. Community amenities such as a swimming pool, tennis courts and clubhouse. Centrally located in

Michael Berlant RE/MAX EXCLUSIVE COLLECTION

Investor Special! This Winter Park gem is an ideal find for investors or home flippers, with *no HOA* and sturdy block construction for peace of mind. Originally a 3-bedroom, 2-bath layout, the home is currently used as a 4-bedroom, 1-bath due to additional walls added by the previous owner. The second bathroom’s plumbing remains intact, simplifying restoration to the original

Whitney Kane THE AGENCY ORLANDO

One or more photo(s) has been virtually staged. Welcome to your dream home in beautiful Winter Park, Florida! This charming 3-bedroom, 2-bath corner unit is just half a mile from Casselberry Commons, offering shopping, dining, and everyday convenience right at your doorstep.Enjoy peace of mind with a new roof (2023), new thermostat and fan (2024), and updated AC ducts and insulation

Yvette Hernandez THE REALTY EXPERIENCE POWERED BY LRR

Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

Marion McGrath ABSOLUTE REALTY GROUP, LLC

This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

Manny Celi YOUNG REAL ESTATE

This property located in a peaceful community 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

Hoover Yap PRIMESTATE REALTY, INC.

This beautifully maintained three-bedroom, two-bath residence features an inviting open floor plan, perfect for both entertaining and everyday living. Recently painted with a fresh interior, the home radiates warmth and brightness throughout. Enjoy modern comforts with a brand-new air conditioning system installed just six months ago, ensuring a cool and comfortable atmosphere year-round. The

Bianca Botelho RE/MAX ASSURED