Winter Park FL. Homes For Sale

Sleek “like new construction” modern style home with clean lines and simple elegance architecture… This home is in incredible condition with everything in near perfect co...

Live in the epicenter of where EVERYONE wants to live in Central Florida — in the Heart of GORGEOUS & EXCLUSIVE Winter Park 32789! The home is nestled in one of the most...

Beautifully updated and move in ready! This lovely one story range home offers 3 bedrooms 2 baths and a stunning backyard oasis with a large swimming pool. The gorgeou...

Welcome home to 921 Golfside! This beautiful split plan house is waiting for you to make it your home! From the canopied street, you'll enter through the foyer and find...

An absolute FIND! Over 1/2 acre on private Lake Sylvan, a spring-fed jewel that is teaming with trout and catfish! In the middle of Old Winter Park, sited on a charming ...

The Perfect Cottage home on a Cul-De-Sac in the Heart of Winter Park! You can't ask for a better location than being just minutes from both Downtown Orlando and Park Ave...

This property is completely renovated. New updated kitchen with beautiful granite counter tops, updated cabinets and appliances, recess lighting, and a 4' X 8' eat in kit...

Finally, a move-in ready home in the highly sought-after area of Winter Park featuring top-rated schools! This beautiful, block home is situated on a quiet street that ba...

Stately Winter Park residence built by Rex-Tibbs on an oversized corner lot on Park Avenue is available and ready for a new owner! This 5-bedroom, 5-bath with office, bo...

Upon arrival you are immediately put on notice that this is a home like no other. Its strong presence is emboldened with elements such as Cor-Ten steel cladding on the cu...

Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Walking distance to the historic Dubsdread Golf Course a...

MULTIPLE OFFER SITUATION! HIGHEST & BEST DUE BY SATURDAY 9PM ON MAY 21st. LOCATION! LOCATION! LOCATION! This updated home is nestled on a quite dead-end street in the he...

From the owner The main reasons I bought this house are the excellent public schools and quiet, family-oriented neighborhood. Our lot is on a quiet street of Winter Park ...

Beautiful Pool Home Now Available! After an extensive renovation in 2019, this home now offers an Open Concept floor plan and all the Modern Amenities that you're lookin...

Pre-Construction. To be built. Are you ready to enjoy this luxurious 4 Bedroom/ 4 Bathroom, two story home in Winter Park? This modern style home features an expansive i...

Modern midcentury offers location and lifestyle! You will love this recently renovated, one-story, two-bedroom and one-bath home situated on a large fenced-in lot with a ...

Beautifully remodeled home in quiet Winter Park neighborhood. Fully renovated this year leaving no stone unturned, this home features all new electrical, plumbing, HVAC, ...

Long day at work? Extended travel? Open this front door and get that “I Love My Home” feeling when you walk into this Gem! A Beautiful, Comfortable 4-bedroom two bath mo...

Located near the end of a tree lined dead end cul de sac has great curb appeal in the Lake Waunatta Woods subdivision in the University Goldenrod area. It is a lovely r...

Under Construction. Under Construction! one or more photos are renderings of the home. Brand new home in the heart of winter park. This new construction modern home is tr...

Set in a gated little enclave on a quiet cul-de-sac in Winter Park, this custom home sports five bedrooms, three-full-and-two-half baths and a wonderful outdoor space to ...

Welcome to Orwin Manor, one of Winter Park's best kept secrets, conveniently located near Advent Health, Park Ave, College Park shopping and dining, and featuring diverse...

Beautifully renovated home tucked away on a quiet street and a short stroll to charming Lake Knowles as well as Phelps Park! This beauty has a delightful brick paver fron...

Totally renovated Modern Farmhouse looks as though Chip and Joanna Gaines had their personal touch on it! Long circle driveway and paver front porch welcomes friends to c...

Welcome to your new home! Perfectly located near top rated schools, minutes from downtown Winter Park and the abundance of shopping, dining and entertainment it has to of...

Opportunity is knocking with this lovely Winter Park pool home. Move quickly on this spacious 4 bedroom, 3 bathroom house boasting fresh updates to bathrooms, media room...

Located in the heart of the Vias, this elegant and meticulously maintained home exudes warmth and endless quality and style throughout. It’s bright, neutral décor and con...

MULTIPLE OFFERS RECIEVED! The seller will be making a decision Tuesday afternoon (5/17). INVESTOR ALERT! Don't miss out on this remarkable Winter Park opportunity right o...

WATERFRONT, LAKE ACCESS, HUGE LOT! This estate is situated on a beautifully landscaped oversized lot that backs up to a tropical canal with full access to 400 acre (Priva...

Under Construction. Under Construction. FG Schaub Custom Home opportunity will be ready in December 2022! Live the custom lifestyle in the highly sought-after Olde Wint...

One or more photo(s) has been virtually staged. Beautiful understated LUXURY tucked away in Winter Park in the small GATED community of Eden Point with a 4-CAR TANDEM GAR...

Walk to Park Avenue from this beautiful traditional masterpiece that will feel like home with every step. Built by Rex-Tibbs, one of Winter Park’s most established home b...

RECENTLY RENOVATED INCLUDING KITCHEN!!! GREAT VALUE! This gorgeous Winter Park home has four bedrooms, three baths along with a large pool and garden patio. As you walk i...

Motivated Seller!!!! Winter Park living! Located 3 miles from historic Downtown Winter Park, this completely upgraded home sits on one of the LARGEST lots with NO HOA! T...

Gorgeous, Transitional Living in 32789. Masterfully designed and built to perfection, this 5 bedroom, 4.5 bathroom pool home offers modern, open living in the Heart of Wi...

You’re going to love this amazing three bedroom 2 1/2 bath plus office home located in the highly sought after city of Winter Park. The stunning yard and driveway have be...

City of Winter Park 1947 Bungalow 1.5 miles to Park Avenue. Listed below market value. 2 1/2 Bathroom PLUS DEN 1940's Block Bungalow in Orwin Manor Estates. This charming...

Come see this BEAUTIFULLY MAINTAINED, IMMACULATE WINTER PARK HOME IN LIKE NEW CONDITION! This is a one owner home and has been maintained in pristine, like new condition....

LAKEFRONT!! Beautiful, Updated Home with an oversized yard of 0.72 acres for you to enjoy with this Spring Fed Jet Ski Lake NAN. Be prepared to fall in love with the wat...

Come see this beautifully renovated 4-bedroom 2 bath home, in a lovely neighborhood in Winter Park with Winter Park schools. It features a brand new Architectual roof, ne...

If you want an affordable home in Winter Park, this is the one! This home has great potential and the location that so many are looking for. It is perfect for 1st Time Ho...

Live in the heart of Winter Park. This cozy 3 bedroom 2 bath, concrete block home with one car garage, screened front porch and no HOA is in walking distance to shopping...

Charming Winter Park bungalow available on a 78' x 113' corner lot. Fantastic location where Park Avenue is a 3-block walk to the East and the Winter Park Village is a 2-...

Located in the prestigious Via’s of Winter Park, this timeless home was custom-built on ½ an acre, and has been meticulously maintained by the original owners. The high-q...

Pre-Construction. To be built. Looking to purchase a new home in Winter Park? Barefoot Brothers Construction group presents this opportunity to build on a quiet street, b...

Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Walking distance to the historic Dubsdread Golf Course. ...

One or more photo(s) has been virtually staged. This Winter Park two-story corner home offers a patio, and a two-car garage.

STUNNING FLORIDA LAKEFRONT home on spring-fed LAKE BURKETT serves up the best of gorgeous views, a terrific Winter Park location, quiet community privacy, and tidy Florid...

Under Construction. Don't miss the opportunity to live in a brand new custom designed pool home built by renowned Winter Park builder Carmen Dominguez. Warm woods and mod...

One or more photo(s) has been virtually staged. This Winter Park one-story home offers granite countertops, and a two-car garage.

This beautiful Modern Mediterranean home is centrally located in Winter Park within walking and biking distance to Park Avenue, Winter Park YMCA, and Phelps Park. The two...

This home is located in the highly sought after Kenilworth Shores neighborhood. A New Roof and New paint inside and out make this home move in ready. A large fenced in b...

Under Construction. Completion estimated by the end of the year. This home features 4,370 square feet of living space comprised of 5 bedrooms and 5.5 bathrooms. The main...

Nestled on the eastern shores of Lake Knowles in the Heart of Winter Park. Enjoy incredible wildlife and beautiful sunsets each night. This home is a MUST SEE. There a...

This property is in the very back of Winter Park Estates. It is on a very quiet street and backs to to a canal for further privacy.

Do not miss out on this charming 3-bedroom 2-bathroom Winter Park charmer! Move in or build your dream home on this 74X120 lot in the desired Sylvan Heights neighborhood....

Excellent opportunity to build your own dream home in Winter Park. Located across the street from Ward Park, Playground, and Fields this oversized 120x135 (0.38 acre) lot...

Pre-Construction. To be built. Location, functionality, beautiful construction and a host of amenities make this the perfect place to call home. Historic oak trees drippi...

One or more photo(s) has been virtually staged. **Price just improved by $10,000!!** Don't miss the opportunity to call this Newly Built 3-bedroom, 2-bathroom property in...

This stunning 3 bedroom 2 bathroom ranch style home is completely remodeled with high end finishes located less than a half mile from Park Ave. This property offers over ...

NEWLY RENOVATED “MOVE-IN READY” home! Featuring new flooring, cabinets, stone counter tops, brand new kitchen appliances, NEW roof and NEW A/C, this home is ready to be y...

Casa del Mondo known as House of the World in Winter Park, is situated on Winter Park Chain of Lakes in the posh and very exclusive Twelve Oaks neighborhood off Park Aven...

HEAVY HANDY-MAN SPECIAL OR KNOCK-DOWN. PROPERTY NEEDS WORK!!! PROPERTY IS A 2 BEDROOM/1BATHROOM WITH 850 SQFT. ROOF REPLACED IN 2020. CALL TO SCHEDULE AN APPOINTMENT TODA...

ONE-OF-A-KIND, 8-Acre, LAKEFRONT, Paradise on Lake Howell (a private, skiable lake) in Winter Park. Over 220 FT. of LAKE FRONTGE w/ Dock & Panoramic Private Lake Views i...

Pre-Construction. To be built. Take advantage of one of the last chances to live in Lake Killarney Shores, one of Winter Park's newest communities - a collection of 30 cu...

Casa Bianca, the extraordinary Winter Park estate, has entered the market for the first time available in over 40 years. Perfectly positioned on the corner of Via Tuscany...

Santa Barbara 4 bedroom 4.5 bath in the heart of Winter Park. Showings on Friday, Saturday, and Sunday only. More pictures to come this week. New countertops and fresh in...

Stunning coastal modern home, wide open and very bright living areas, 3 bedrooms/2.5 baths, with lush tropical landscaping situated perfectly just 5-10 minutes from downt...

Elegant classic design with custom finish work in this traditional yet timeless home. Detached apartment with private entrance offers flexible space for extended family o...

New Price! Absolutely stunning, mid-century modern home in Winter Park! Fantastic location just minutes from nearby shops and dining and less than 10 minutes to Park Aven...

One or more photo(s) has been virtually staged. This Winter Park one-story home offers a patio, and granite countertops.

Unique opportunity to own a large home in Winter Park's Kings Cove subdivision. There are 4 bedrooms, 3.5 baths, an office, and a potential fifth bedroom. The entire bac...

THIS IS A TRI-PLEX with a waterfront view of Baldwin Lake with a Winter Park address! NEW ROOF and new panel box. No HOA. Perfectly positioned across the street from Bal...

WINTER PARK VIA’S!!! Incredible Oversized Lot is located in the “Heart” of Winter Park. Very Unique opportunity in Winter Park for a high-quality custom build. The bric...

Welcome home to this effortlessly bright and open, oversized, almost half-acre property with a beautiful lake view, located in one of the most precious and private spots ...

Beautiful Mediterranean Lakefront estate with 5 bedrooms, 3.5 bathrooms, sandy beach (one of a kind) and 127’ on lake Osceola. Enjoy captivating views of lake Osceola, pa...

A fantastic waterfront opportunity in Winter Park on the Lake Maitland Lagoon awaits. This 0.62-acre lot features 100-feet of frontage on Lake Maitland’s quiet lagoon and...

*Bring your boat, your RV, your utility trailers, No HOA you may park in the side yard! 4 bedroom 3.5 bath 2 car garage home situated on 1/2 acre in Winter Park!! This is...

Contemporary living in the heart of Winter Park. This Phil Kean designed/built home is sure to be at the top of your list. Phil Kean’s distinctive signature style feature...

Some photos have been virtually staged. If you need LOTS of bedrooms and SPACE or want a separate MOTHER-IN-LAW SUITE, then this unique property may be for you! Just lock...

Beautiful 1930’s Winter Park Character Home on Oversized 0.42 acre lot with privacy gate, detached mother-in law apartment, screened pool, and so much more. Originally bu...

Pre-Construction. To be built. This stunning new house in Winter Park features the perfect blend of textures and clean finishes with modern warmth and undeniable sleeknes...

One or more photo(s) has been virtually staged. This Winter Park one-story home offers granite countertops.

LOWER PRICE, Great Investor Opportunity: Very desirable Tanglewood Winter Park neighborhood with many updated properties. This home sits on a corner lot with over 1/4 a...

Pre-Construction. To be built. Take advantage of one of the last chances to live in Lake Killarney Shores, one of Winter Park's newest communities - a collection of 30 cu...

Beautiful Ray Coudriet built home on Lake Mizell. Greet your guests from the Balcony overlooking the Motor Courtyard. The Master Suite has extensive amenities including a...

Move in ready 4-bedroom, 2-bathroom home in the ideal Winter Park Neighborhood across from Winter Park High School.

Pre-Construction. To be built. Here is the perfect opportunity to purchase your very own private sanctuary in the heart of Winter Park. This exquisite transitional modern...

This Winter Park one-story home offers a one-car garage. This home has been virtually staged to illustrate its potential.

Pre-Construction. To be built. This impressive modern coastal farmhouse is being built by Parade of Homes award winning builder, Meridian Homes. Located on an impressive ...

Pre-inspected. Offered for the first time in over 30 years! Winter Park’s only original, charming and completely remodeled historical farmhouse. Known as the “Harris-Edis...

On almost one acre in the heart of Winter Park, this beautiful Victorian home was extensively and meticulously remodeled and modernized in 2002 and 2011, while still reta...

Under Construction. Completion in July 2022. Single family home and model unit. 4 bedrooms and 3.5 bathrooms equipped with an elevator. Enjoy luxury living and premium so...

Pre-Construction. To be built. Excellent opportunity to build a modern coastal custom home with a 2 car rear entry garage in a very desirable location. This 3148 square f...