Winter Park, FL Homes for Sale with Acreage

Welcome to Tucks Knoll in Winter Park! Nestled on over FOUR ACRES at the end of a private cul-de-sac, this exceptional 4-bedroom, 4-bathroom residence offers more than 3,300 square feet of luxurious living space and a lifestyle that feels like your own private retreat. Backing up to a lush CONSERVATION area with the peaceful flow of Howell Creek, the property is surrounded by mature trees,

Nicole Dege REDFIN CORPORATION

FIRST-FLOOR LIVING WITH DIRECT WATER VIEWS AND AN UNBEATABLE LOCATION! Located in one of Winter Park’s most convenient and cared-for communities, The Gallery at Winter Park. This 2-bedroom, 2-bath condo showcases a beautifully updated kitchen and refreshed bathrooms. Contemporary luxury vinyl floors extend across the bedrooms and living areas for a clean, cohesive look. The primary suite is at

Maria Elena Perez MEP REALTY INVESTMENTS 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

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

Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

Adriana Sanchez AGENT TRUST REALTY CORPORATION

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

Charming Downtown Winter Park Pied-a-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

Mary Colton FANNIE HILLMAN & ASSOCIATES

Excellent location. You can walk to grocery stores, banks, pharmacies in the area. Short drive to Full Sail and Rollins College as well as Park avenue where you have many restaurants, coffee shops, retail.

Didem Isik Widener PARK AVENUE REALTY LLC

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue.This stately 6-bedroom, 5.5-bathroom home

Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural

Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

Beautiful pool home with an open great room plan with high vaulted ceilings and master on the first floor situated on one of the largest lots in the subdivision with over an acre of land that extends all the way to Howell Creek. You’ll love the open and airy feel from the high ceilings and master suite features a large walk in closet and garden tub. Roof is 2022. The kitchen and formal dining

Hojin Chang RE/MAX PRIME PROPERTIES

Welcome to this spacious and beautifully updated first-floor condo with 1 bedroom, 1 bathroom in the heart of Winter Park, the highly sought after Four Seasons community. This unit offers the convenience of walk-up access and a covered carport just steps from your private screened patio and laundry inside the unit. The kitchen was remodeled in 2021 and features white shaker-style cabinetry, a

Amy Turner KELLER WILLIAMS WINTER PARK

Welcome to 3057 Aaron Burr Ave #2, a beautifully updated 2-bedroom, 2-bathroom condo in the desirable Colonies community. Whether you're looking for a stylish home or a fantastic investment opportunity, this property checks all the boxes!Step inside to find brand-new stainless-steel appliances, granite countertops, and spacious walk-in closets. The open layout creates a bright and inviting

Claudia Villarroel ROBERT SLACK LLC

Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve

Kelly Price KELLY PRICE & COMPANY LLC

Rare Corner Top-Floor Condo with Expansive Views in Winter Park’s Premier Location!Discover this beautifully maintained 2-bedroom, 2-bath top-floor corner unit in the highly sought-after Villages of Winterset Condominiums. Bathed in natural light and offering stunning broad views, this inviting home combines comfort, privacy, and unbeatable convenience.Enjoy the ease of top-floor

Daniel Vanzelli D.V REALTY CONSULTANTS

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currently available in same complex MLS: R4909222, R4909220, ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other

Scott Butts KIMBRIDGE REALTY, LLC

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currently available in same complex MLS: R4909222, R4909221 ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other

Scott Butts KIMBRIDGE REALTY, LLC

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currently available in same complex MLS: R4909220, R4909221 ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other

Scott Butts KIMBRIDGE REALTY, LLC

Completely remodeled and move-in ready, this beautiful 1-bedroom, 1-bathroom condo in Winter Park offers the perfect blend of comfort, convenience, and value. Located just 11 minutes from Orlando International Airport and close to UCF, Full Sail University, shopping malls, restaurants, major highways, and popular theme parks, this home is ideal for both homeowners and investors. The condo

John Silva JOHN SILVA REALTY & ASSOCIATES

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

Beautifully Renovated Lakefront Condo with Partial Lake Virginia & Downtown Views. Located just minutes from Park Avenue and Rollins College, this fully renovated condo offers stylish, maintenance-free living with partial views of Lake Virginia and the downtown skyline. The open-concept layout features a brand-new kitchen with quartz countertops, stainless steel Samsung appliances, recessed

Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

Welcome to your privately Gated Lakefront Estate, with stunning views and a fully equipped Guest Suite in one of Winter Park’s Most Desirable Locations! This private, beautifully landscaped property features an Open-Concept floor plan with expansive windows showcasing STUNNING panoramic lake views throughout. Lush Landscaping and privacy Fencing line both sides of the property. The spacious

Jerad Withrow SPECTRUM GLOBAL REALTY, INC

NEW PRICE!!! Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat!Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to

Katherine Bordelon CASTLE & COTTAGE REALTY LLC

READY TO MOVE !!!! Updated 2-bedroom, 2-bath condo featuring modern finishes throughout! This condo features TITLE floors, sleek granite countertops, and stainless steel appliances in the kitchen, A rare find with an in-unit washer and dryer for added convenience; This home also has plenty of natural light! The primary suite features an en-suite bath, providing comfort and convenience. A

Adriana Sanchez AGENT TRUST REALTY CORPORATION

Spacious and inviting, this 2-bedroom, 2-bathroom condo in Winter Park is a fantastic investment or personal home. The open living space seamlessly connects the living and dining area, creating a bright and airy atmosphere perfect for entertaining or relaxing. This home also has plenty of natural light! The primary suite features an en-suite bath, providing comfort and convenience. A second

Kayla Cardenas WHEATLEY REALTY GROUP

Huge Price Reduction!!! on this Fully remodeled unit. Reduced to sell. This fully updated Condo is minutes from Baldwin Park, Full Sail, UCF, and all of Winter Park has to offer. Don't miss the opportunity to own an amazing home or investment opportunity. Low HOAs are hard to find, especially in Winter Park Zip codes. Don't forget that this home has a fully updated kitchen, bathrooms, and new

Benjamin Berry EXP REALTY LLC

Updated 2-bedroom, 2-bath condo featuring modern finishes throughout! This condo features laminate floors, sleek granite countertops, and stainless steel appliances in the kitchen. A rare find with an in-unit washer and dryer for added convenience. Step out onto the brand new deck, upgraded with durable composite decking—perfect for relaxing or entertaining. Ideally located just minutes from Full

Daniel Graves GRAVES REALTY

One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price of $415,000. This fully renovated one-bedroom, one-bathroom condo spans 900 square feet and offers single-story, ground-floor, corner-unit living just steps from Park Avenue. The 2018 full renovation was extensive and included new electrical

Padgett McCormick KELLY PRICE & COMPANY LLC