Winter Park, FL Homes for Sale under $400,000

Welcome to your dream home in Winter Park! This beautifully updated, spacious two-bedroom condo is nestled in the highly sought-after Cedarwood Village Condominium, a well-maintained community known for its charm and appeal. Meticulously cared for, this residence boasts modern elegance with gleaming quartz countertops and premium flooring throughout. The master suite is a true retreat, featuring

Bryce Jones CHARLES RUTENBERG REALTY ORLANDO

Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location and this 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with

Simon Colak USCO CAPITAL GROUP

This stunning home has been completely renovated and is ready for you to move in! Featuring 3 bedrooms, 2 full bathrooms, and a screened-in pool with a spacious deck, it blends modern style with everyday comfort. Inside, you’ll find brand-new waterproof laminate flooring, fresh paint throughout, and stylish modern finishes that create a light and inviting atmosphere. The open and spacious common

Gea Gomez LPT REALTY, LLC

Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

Melissa Woodman FANNIE HILLMAN & ASSOCIATES

Aloma Trails is a gated townhome community, built by Ryan Homes, located in Winter Park. Conveniently you'll find it's location between UCF and Rollins College. Seminole County is known for its highly rated public schools. Only minutes from Park Avenue shopping and restaurants. This END UNIT townhome features 3 bedrooms, 2 1/2 bathrooms, and a TWO car garage. Granite countertops, 42” upper

Corey Van Dyke HOMEVEST REALTY

Charming 3-bedroom, 2-bathroom single-family home nestled on a generous 9,626 sq ft lot in Winter Park’s desirable Goldenrod area. Built in 1972, this cozy one-story home offers 1,104 sq ft of living space with a classic split-bedroom floor plan — perfect for privacy while entertaining. The residence features tile and carpet flooring, central air conditioning, and a functional kitchen complete

Rosa Rivera SKINNER REALTY, INC.

A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. This is a two bedroom and one bath in the front with a one bedroom one bath mother-in-law suite in the back, off of the laundry room with its own entrance as well. Main house has a large foyer and living room. Kitchen has beautiful cabinets and granite counter tops. Septic system was just replaced in September. Currently rented for $2,000

Moe Mossa SAVVY AVENUE, LLC

Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family

George Freelove KELLER WILLIAMS WINTER PARK

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 $399,000. 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

Lovingly Maintained by original owner. This is a true 4 bedroom home with 2 bathrooms and a single car garage. Located in desirable Winter Park with easy access to major roads, convenient to shopping, the post office, restaurants, higher education, and airports. This solid built home features a split plan, large living room with a wall of closet space, easy access walk - through kitchen, screened

Wanda Perkins GLOBAL PROPERTIES SALES & MGMT

Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

Mary Colton FANNIE HILLMAN & ASSOCIATES

Prepare to fall in love with this comfy, cozy retreat tucked along a charming tree-lined street. From the inviting front elevation to the welcoming sitting porch and long driveway, this home instantly feels like “the one.” Inside, soaring vaulted ceilings and beautiful wood flooring create a warm, open atmosphere, while the eat-in kitchen shines with stainless appliances and extended counter

Victoria Myers RE/MAX TOWN & COUNTRY REALTY

One or more photo(s) has been virtually staged. AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. One or more photo(s) has been virtually staged. Welcome to 2189 Sussex Road, a home with strong potential located in the Winter Woods community of Winter Park. This property presents an opportunity for investors or buyers seeking a renovation project. The home is being offered as-is. The layout

William Vega LPT REALTY, LLC

One or more photo(s) has been virtually staged. Welcome home to this beautifully updated 3-bedroom, 3.5-bath townhome tucked away on a quiet cul-de-sac in a desirable Winter Park community. Designed with comfort and functionality in mind, each bedroom features its own private bathroom, including a convenient first-floor bedroom with a fully updated, handicap-accessible bath showcasing a spacious

Jean Scott KELLER WILLIAMS ADVANTAGE REALTY

Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, 3 Bedroom Town Home with a Garage in the VIA LAGO GATED community?? ABSOLUTELY! Meticulously maintained and spacious town home is just waiting for its new owner! Elegant brick paver driveway and entryway greet you as you pull up. The downstairs is open, light and bright. The beautifully appointed kitchen has

Stephen Hachey FLAT FEE MLS REALTY

Welcome to Killarney Bay—Winter Park’s best-kept secret for tranquil lakeside living, and just steps from the city’s finest shopping and dining!This beautifully updated and spacious 2-bedroom, 2.5-bath townhome-style condo offers a rare blend of modern upgrades and classic charm. Enjoy a BRAND NEW WATER HEATER, vaulted ceilings, a wood-burning fireplace, and rich wood-like flooring

Blaike Gill KELLER WILLIAMS WINTER PARK

The perfect hideaway home, nestled in the oaks, in coveted and charming Winter Park. Get the ''small-town'' feel, close to all the dynamic, high-energy Orlando has to offer. Your key gateway and home base to picturesque Central Florida. This versatile 2-story end-unit townhouse in a park-like setting lives like a single-family home. Privacy galore. It will appeal not just to 'Orlandoans' but also

TJ TAMARA FISHER Compass Florida LLC

Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment. Located on the first floor, this beautifully renovated 2-bed, 2-bath home features an open

Brandon Geers COMPASS FLORIDA LLC

Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life.Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more!The community offers a complete infrastructure with a swimming

Marcus Freire de Araujo WRA BUSINESS & REAL ESTATE

This 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space in a highly sought-after location. Enjoy a bright living area featuring a gorgeous tiled fireplace, built-in bookshelves, and two sets of French doors that open to your private patio and fenced backyard with brick pavers and turf grass. The home includes a spacious double vanity bathroom, custom shelving

Steven Koleno BEYCOME OF FLORIDA LLC

Make it your very own in 2026! Great opportunity to add your personal touches to this super 3 bed / 2 bath home in desirable Country Lane neighborhood. Vaulted ceiling bring tons of natural light into this great room style floorplan. Bonus room off dining area for office or crafts with door to fenced back yard - perfect for pets and play! Sunny kitchen at the heart of the home, with ample cabinet

Lisa Gould KELLER WILLIAMS WINTER PARK

Major Price Improvement! 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 Integrity Reserve Study

Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

One or more photo(s) has been virtually staged. Welcome Home! Incredible opportunity to live in the desirable Country Lane community in Winter Park! This charming 3-bedroom, 2-bath POOL home features an extra-large backyard, ideal for entertaining, play, or future outdoor projects. Inside, you’ll love the beautiful engineered hardwood floors throughout—NO carpet! Major updates include New A/C

Noella Tinkler MARK SPAIN REAL ESTATE

Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood

Richard Traynor FLORIDA ONE REAL ESTATE LLC

Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home has a

David Ruiz CENTRAL REALTY

This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

Bennie Olivo BOX REAL ESTATE LLC

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

Dominick Florio RE/MAX TOWN & COUNTRY REALTY