Winter Park FL. Homes For Sale

Stunningly inviting, this beautifully appointed Winter Park home in the prestigious GATED Bear Gully Pointe community will take your breath away! The community is situat...

Start Packing! This Lovely four bedroom two bathroom home located in sought after Winter Park Pines ready for a new owner. This home is exquisitely upgraded with beautifu...

Charming 3 bedroom, 2.5 bathroom, two-story home located in the wonderful community of Autumn Glen in Winter Park. The welcoming front porch is a perfect place to meet yo...

LOCATION! LOCATION! LOCATION! Mid-Century Large Cottage Home. NO HOA! There are so many charming details about this home, the tile (backsplash) in the kitchen, the built-...

Nestled in the private cul-de-sac of Via Tuscany Oaks, the Eastward-facing home joins 6 other estates, built around a central park, secured by a brick wall, & boasts an a...

Wonderful home, neat, clean and ready to go! Laminate and tile floors throughout, gas fireplace in great room plus mirrored accent wall, vaulted ceilings. The kitchen is ...

This contemporary elegant home is located in Olde Winter Park...the interior of the home has a very open floor plan...it has a resort style pool with lush landscaping and...

Welcome to your very own slice of paradise in Winter Park! Opening the front door you’re immediately welcomed into the living room filled with natural light from the larg...

Welcome home to the Golfside neighborhood AKA Winter Park's best kept secret! Where the mailman delivers to your door, BEAUTIFUL TREE LINED STREETS and sidewalks on both ...

Wanting to live in the "Via's"- This home is perfect for you! Full of upgrades and the attention to detail as you would expect! The home was just freshly painted outside,...

Lakefront home, with innumerable upgrades in Winter Park. Gorgeous views from the widest setpoints on private spring-fed Lake Waunatta. Through this established neighborh...

Exciting opportunity to own an Elegant Custom Lakefront Estate located on the Winter Park Chain of Lakes (Casa Fiera Vista). This home is an Aurora and Parade of Homes Gr...

RARE OPPORTUNITY to own this Winter Park home in the charming neighborhood of EASTBROOK. Whether you're a first-time homebuyer or looking to invest you'll appreciate this...

Nestled along the most exclusive street in the Windsong neighborhood, this estate epitomizes the luxury that has made Winter Park THE destination for discerning residents...

Beautiful Charming and Newly Remodeled 4/2 home in well Desired area in winter park. This property boasts new tiles floors , new hard wood flooring in bedrooms, newly ren...

Imagine the possibilities! This property features a charming bungalow that you could move into, renovate, or tear down and build something brand new. It's comprised of tw...

Pre-Construction. To be built. International Design meets elegant transitional lines in this new Golf-View Winter Park home. Located in the downtown Winter Park corridor/...

In the celebrated City of Winter Park. No HOA fee, "A" School district home. Immaculate Converted 4 bedroom 2 bath split plan home with fresh interior paint! Converted ro...

REdUCED!!!! great house in lovely Park Grove. Walking distance to Park Ave, great Schools., family neighborhood. Renovated and updated.

Will not last! This house has been given a contemporary face lift. Gorgeous renovated Kitchen including granite countertops, tiled back splash, Skylight, and built in eat...

Simply stunning MOVE-IN ready solid block three bedroom two bathroom POOL HOME in the heart of WINTER PARK!! Open the DOUBLE DOORS to magnificent PORCELAIN TILE FLOORS gr...

Spacious 3 bedroom, 2 bath block home with 2 car garage and large, fenced-in back yard on a cul-de-sac in Winter Park. As you enter the home, you will see a large formal ...

Be Impressed with this Completely Renovated 6 Bedrooms Plus Office and 3 Full Bathrooms Home to Enjoy with Your Family & Loved Ones. Also It Could be a Great Investment P...

Under Construction. BRAND NEW CONSTRUCTION IN WINTER PARK! Stunning 4 bedroom, 3.5 bath home designed and built by local builder Homes by Carmen Dominguez. Every detail t...

One or more photo(s) has been virtually staged. Looking for a home built with magic? This is it! This 5 bedroom, 5 and a half bathroom home boasts breathtaking views of B...

Grand southern elegant custom home with 5,243 sq ft in one of Winter Park’s most charming and sought after neighborhoods. A double balcony, paver driveway with remote con...

Seller Motivated, Bonus offered. Excellent Winter Park location at an affordable price. Perfect for AIR BNB or New Home Owner Located close to the 417, UCF, Rollins Colle...

WOW!!! NEW ELECTRICAL, NEW A/C, NEW PLUMBING, NEW ROOF, RESURFACED POOL AND IF YOU NEEDED MORE... HOME HAS BEEN APPRAISED (WILL PROVIDE UPON REQUEST) AT $472k. Sitting on...

Breathtaking high-quality home built by Zoltan Homes, in prime location in Winter Park. Boasting a tremendous open floor plan with over 11ft ceilings on the 1st floor and...

Under Construction. This Stunning transitional 5 bedroom pool home is perfect for family living & entertaining. Floor plan is ideal w/ 2 bedroom suites downstairs plus of...

Another meticulously custom built masterpiece by award winning Austin Homes! Situated on an over-sized lot w/ deeded lake access to the prestigious Winter Park Chain of L...

Great updated home with water views on an oversized lot.This charming 3 bed, 2.5 bath home offers, hardwood floors, updated appliances, and granite tops. The community of...

Just Listed! Gorgeous .82 acre estate home in Winter Park’s Sevilla neighborhood. Set on an oversized lot that offers 120’ along Howell Creek, this amazing, one-of-a-kind...

PRICE REDUCED! This lovely home is nestled in a charming family neighborhood in Winter Park with the desirable Seminole County school district. This adorable 3 bedroom/2 ...

Rare opportunity to own a lakefront home on over 1 acre lot located in the highly desirable Vias of Winter Park. Nestled on a quiet, brick, and cul-de-sac street, this sl...

A must-see! 3 bedroom/2 bath home located in Winter Park! The generous 1/3 acre 2 corner lot gives you plenty of space with no neighbors on three sides, plus a fenced bac...

Great quiet neighborhood in Winter Park. NO HOA! 4 bedroom 2 bathroom home updated in and out! No carpet in living areas! (engineered hardwood and tile) and carpets in...

Moments from the charms of downtown Winter Park in the highly sought-after Windsong neighborhood, a magnificent Mediterranean masterpiece awaits. Stunningly appointed and...

Come tour this adorable, move-in ready ranch-style home located at the heart of everything! Winter Park Schools! Just a short stroll to Park Avenue, Rollins College, YMCA...

Spectacular home in a great Winter Park location...this 4 bedroom custom home is located on a quiet street in the heart of Winter Park. The 1st floor has stone flooring &...

The location of this charming updated gem does not get any better in Winter Park. This stunning 4 bedroom 3 bath property sits with lovely elevation on one of the most d...

Get Ready for this ULTIMATE energy efficient smart home. This recently built MOVE IN READY home has 5 bedrooms and 3 bathrooms and is located in the highly sought after ...

One or more photo(s) has been virtually staged. Lovely custom built home with numerous upgrades throughout. Walk to Phelps Park, YMCA & Lakemont Elementary! Spacious & pr...

Wow! Location, Location, Location! This solid built home is filled with potential. Located in the heart of Winter Park, right around the corner from the beautiful Ward Pa...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready March 2020! The Kerrville II floor plan impresses upon entry with a formal living and dinin...

PRICED BELOW APPRAISAL! The perfect balance of elegance, luxury and location adorns this 4 bedroom, 3.5 bath custom built home located on prestigious Palmer Avenue. You w...

Mediterranean Ranch home with new updates in Winter Park. Gourmet kitchen upgrades include GE double ovens, induction cooktop, marble backsplash, large marble island and...

Step inside and fall in love with this Winter Park beauty. Sitting on a corner lot and walking distance to downtown Winter Park this home is overflowing with old school g...

The ultimate Coastal Modern home is now available. Located in the highly coveted tree streets of Winter Park this home was custom built by premier builder Austin Homes an...

LOVINGLY MAINTAINED AND NEAT AS A PIN! MOVE IN READY WINTER PARK CHARMER, IN DUBSDREAD AND CLOSE TO EVERYTHING. THIS 3 BED 2 BATH HOME BUILT IN 1954, HAS ALMOST 1500 SQ F...

Situated on over a half acre of lush landscaping located a short walking distance to Park Avenue... this gorgeous 1940s ranch-style residence has been meticulously mainta...

Welcome home to this beautifully renovated just under 3, 000 Sq. Ft., four-bedroom, two-bath ranch style house which offers the opportunity to live and play in the Heart ...

Located in the North Corrine neighborhoods of Winter Park, this 3 Bed, 2 Bath, 1764 sqft ranch home offers an open floor plan, new roof, 2015 AC and walking distance to 3...

Former parade of home winner underwent a meticulous renovation in 2019 creating the newest completely updated home in the Vias available on the market today. With its pro...

Great opportunity to purchase an awesome 3/2 pool home with open floor plan and nice renovations. The following updates were all done within the last 1-2 years. New roof...

Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150’ on the shores of Lake Berry. Custom built and architecturally stunning, this 5 bedroom, 4....

This stunning Winter Park home is located on the Tree Streets and is a short walk to Phelps Park, YMCA, and minutes drive to Park Avenue shops and restaurants. This beaut...

Half an acre in superior location steps away from Lake Chelton on brick streets in 32789. Considered one of the best neighborhoods in Winter Park! Beautifully remodeled M...

Fantastic value in Winter Park! Can use 4/5th bedroom for separate in law suite or private owner retreat. Don't let the outside fool you! 4 bedrooms plus a large office w...

The Value is in the Land! 150' wide x 130' deep, TWO Build-able Lots! Charming Spanish revival influenced home nestled in old Winter Park. Barrel mission tiles accent the...

Close to everything. Back yard is adjacent to enviromental area.

If you love to cook and/or bake this is the kitchen for you. Recently remodeled and ready for you. Lovely granite counters and stainless steel appliances. Both bathroo...

This stunning two-story, one-owner home with unique Italian Renaissance elevation offers four bedrooms, four and a half baths, and 3,814 sq. ft. of open living space. Bea...

Welcome to the highly desirable water view neighborhood in Winter Park. CANAL FRONT estate on the chain of lakes with original boat slip. 2 pieces of parcels for a pric...

Winter Park Pool home on 1/3 acre located next to Baldwin Park. Beautiful 3 bedroom, 2 bathroom Pool home with large fenced lot located just outside of Baldwin Park. This...

Almost new in the Aloma area of Winter Park with a screened in lanai to enjoy your morning coffee. Your new home features the open concept of a great room with surround ...

Exceptional & Delightful Winter Park home! A thoughtfully executed quality build by Rex-Tibbs that offers so many sought after features, like gracious open floor plan, sp...

Cute and cozy Florida home located in Winter Park. This 3 bedroom 1.5 bath home with an extra bonus room in Winter Park Estates features over 1200 sq ft of living space. ...

NEW CUSTOM CONSTRUCTION IN WINTER PARK 32789 UNDER $700K!!! Stunning coastal modern home, wide open and very bright living areas, 3 bedrooms/2.5 baths, with lush tropical...

Charming & UPDATED WINTER PARK POOL HOME; 3 bedroom 2 baths w/ open floorplan; upon entering you are greeted w/ views thru the great room & dining area to the Florida ro...

Charming block home updated throughout in Winter Park 32789. Great starter home, investment opportunity or tear down for new build. This neighborhood is going through gre...

Don't miss out on this one of a kind, 3 story home. This home is 5 bedroom, 3.5 bathroom homes zoned for a work/live so you can easily make this space your office as well...

One or more photo(s) has been virtually staged. **New Construction and newly Renovated Property** Welcome to beautiful 1811 Bryan Avenue, centrally located in the heart ...

The value is in the land. Fantastic location. Unique opportunity to build a custom home with Maroon Fine Home, Inc. This beautiful property is located only a few bl...

Location, Location, Location! This location doesn’t come along very often, so this could be an opportunity for you to own this charming and unique Sears catalog “Crescent...

Are you looking for that special Winter Park home with separate In-Law Suite?? Look No Further! This is the Winter Park home that you have been looking for. Warm and fami...

Located on a cul-de-sac in a desirable gated community in Winter Park, this 5 bedrooms/3 full bathrooms/2 ½ bathrooms house sits on an oversized lot. The community border...

Lovely 4/2 home with screen patio & 2 car garage

Welcome to this move-in-ready 4 bedroom, 3 1/2 bathroom pool home located in the wonderful community of Enclave at Aloma in Winter Park. This home features an open livin...

By far one of the most dramatic interiors of any home on the market in Winter Park. Award winning Brian Schlosser of NV design as created this exquisite remodel in the he...

Live in Winter Park’s Golden Triangle! Walk to Park Avenue, the Winter Park 9, Whole Foods - you name it! Rarely available, prime location and pure potential, this lock...

***Value is in the Land***Bring your Builder and Build Your Dream Home***This is your opportunity to live in the spectacular and highly sought after Sicilian Shores secti...

Renovated in 2018 and move-in ready. In a great Winter Park location with deeded access to Lake Killarney. Situated on a large 0.35 acre lot in a quiet neighborhood with ...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January 2020! The Valencia features an open floor plan providing flexibility and is perfec...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January 2020! Use this Florentine's first-floor flex room as a formal living or dining roo...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January 2020! The one-story Shore home features a split floor plan. Gourmet kitchen overlo...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready February 2020! Relax and unwind in the Chislett's private master suite featuring tray ceil...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January 2020! The Palermo II is a one-story home featuring tile roofing, 3 car garage, ext...

Adorable 3 Bedrooms /1 Bathroom in the Heart of College Park, Close to Dubsdread Golf Course Area with Winter Park address. Dubsdread Golf Course right around corner. Hom...

This stunning Winter Park home, situated in the desirable Orwin Manor neighborhood, combines style and elegance with the most convenient location in all of Central Florid...

Location,! Location! Don't miss this Prime Winter Park Location gem in the rough. Walk to Winter Park Village. Close to Rollins College, the Winter Park Farmers Marke...

Builder's dream lot! This very large lot, 77x151.42, is located on one of the very desirable "tree streets" of Winter Park. Extremely convenient location, walking dista...

Stately custom Winter Park estate on Lake Maitland spans over 10,000 sq ft, offers 6-bed,7-baths,2-half for gracious living and refined comfortable entertaining.Two-story...

Modernized gourmet kitchen with eat in area, featuring French doors opening to a private enclosed large outdoor brick paved yard, perfect for year round Florida en...

Under Construction. Unique ONE-STORY build on oversized lot. Brand new construction offered by Rex-Tibbs Construction, one of Winter Park's premier custom home builders f...

Stunning Spacious 5 Bedroom 3.5 Bath POOL HOME with 1ST FLOOR MASTER now available with a Winter Park address. This Beautiful 2 Story is ready for your extended family an...

This beautiful Spanish Casita style home is located in highly desirable Winter Park. It is a short distance to Park Avenue, Hannibal Square, and Winter Park Village. Ente...

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

INVESTOR ALERT! Great tenants in place and occupied until 5/15/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

This beautiful 7 bedroom pool home features a traditional layout with formal living and dining rooms, an open kitchen and family room, and downstairs guest bedroom. From ...

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

***WONDERFUL WINTER PARK*** NEW QUALITY CONSTRUCTION!!! This Fabulous 5 Bedroom, 3 and 1 Half Bath New Build has it all! Huge First Floor Master Suite with Walk In Clo...

***Multiple offer notice...highest and best due from all buyers by 01/21/2020 11:59PM Mountain Standard Time...Awesome opportunity to own this 4 bedroom 3 and a half bath...

One or more photo(s) has been virtually staged. PICTURESQUE WINTER PARK LOCATION! Perfectly nestled on almost half an acre, this stunning 5 bedroom 5 1/2 bath pool home o...

A luxurious lakeside lifestyle awaits you in this exquisite 5 bedroom 5.5 bathroom 6,000+ sq ft Winter Park waterfront estate. With a lot comprising of just under 3/4 of ...

Classic Winter Park home combines character, quality and extreme live-ability. Do you like to entertain? High end ( to the studs) renovated chef's kitchen with large cent...

This extraordinary, one-of-a-kind home, just 3 blocks from Park Avenue offers a luxury Winter Park lifestyle in a low maintenance easy living package - and it lives BIG! ...

Meticulously constructed 4 bedroom, 5.5 bath pool home in The Vias. Encompassing over 6,200 square feet of beautiful interior space, this home sits on an oversized .42 ac...

LIKE NEW Winter Park home, completed in January 2018! 5 oversized bedrooms and 5 full baths, plus 1 half bath, with plenty of BACKYARD SPACE! The open floor plan for this...

Fabulous Winter Park premier zip code 32789 with brick roads. This house has an excellent floor plan, large bedrooms and a large fenced in back yard. Minutes from all tha...

*PRICE IMPROVEMENT* Don't miss your opportunity for this newly constructed Winter Park 5 bedroom 4.5 bath home in this exclusive, gated community. This two story home has...

Enjoy maintenance free living at Hawks Crest at Winter Park! Clubhouse,walking trails, gym, dog park, canoe launch to Lake howell to enjoy beautiful sunsets are all a apa...

One or more photo(s) has been virtually staged. PRICED TO SELL! Welcome to Sanctuary at Aloma's EXCLUSIVE GATED COMMUNITY, on a quiet, private CUL-DE-SAC with a DIRECT PO...

This Spectacular local art curator's home is an elegant Winter Park lakefront masterpiece custom built with luxurious finishes by Fred Schaub Homes. Including the outside...

As you walk in through the front door, your greeted by your open floor plan, with a gorgeous view of your pool. The pool area has been remodeled, and placed perfectly in...

Pre-Construction. To be built. PRE-CONSTRUCTION - Don't miss out on this gorgeous new construction home in Winter Park! This 5 bedroom 4 bathroom house includes huge room...

Gorgeous Custom Home on Skiable Lake Now Available. 1st Place Parade of Homes Winner. Luxury Lifestyle on the Water awaits. This home was designed with comfort, entertai...

This two-story house, in the heart of Winter Park, features 11 rooms including a spacious master suite, guest bedroom and powder room downstairs, large family room, kitc...

Located on the shores of Lake Howell, this Lakefront property offers the potential buyer over 4 acres of High and Dry Land in a serene natural setting. After viewing the ...

AMAZING FULL RENOVATED LAKE ACCESS HOUSE ,PERFECT LOCATION Don"t miss out on this rare opportunity to purchased this newly renovated gem located in the much desirable Ju...

If you are looking for a Winter Park address, this home is a must see. A true GEM on Karolina on Killarney. You’ll be buying 2 homes on one lot!! You must see it to truly...

Elegant canal front estate on the Winter Park Chain of Lakes. Beautifully remodeled & tastefully enhanced. Premier location on an oversized lot, a short walk to Park Ave....

WOW NEW PRICE! Don’t miss out on this open floor plan home situated on almost 3/4 acre lot on tranquil Bear Gully Rd. in Winter Park! The home features open floor split c...

MAJOR PRICE REDUCTION FOR QUICK SALE!! Meticulously maintained mid-century home on an oversized CORNER lot in the middle of Winter Park! Located just minutes from shoppin...

Under Construction. New Construction! This two-story crafstman home features 4 bedrooms and 4 full bathrooms in nearly 3,400 square feet of living space. The location is ...

NEW CONSTRUCTION-This Beautiful New Country-Contemporary Home was orchestrated by an award winning team of professionals. >Green Apple Architecture >SEI Custom Homes >Deb...

AVAILABLE NOW! Classic Homes presents the Urban Farmhouse in this new enclave of 30 custom homes along the shores of pristine Lake Killarney with access to the Lake via a...

This Winter Park one-story home offers a fireplace, granite kitchen countertops, a master bath step-in shower, bathroom granite vanity, and a patio. Upgraded features in...

Lovely Upgraded Winter Park POOL home with 3 Bedrooms, 2 Baths Plus Office/Den, HUGE FLORIDA ROOM with a REMODELED KITCHEN & UPDATED BATHS on a LARGE, FULLY-FENCED CORNER...

Come and look at this great estate in a great neighborhood in the Winter Park area. The owners have maintained this home with all necessary upgrades and made it move in r...

Spectacular Custom Spanish/Mediterranean Home Locate In The Heart Of Winter Park , This Beautiful Home Is Featuring A Large First Floor Master Bedroom With Him/Her Walkin...

Beautifully maintained home on an exceptional and quiet street in Golfside area of Winter Park. From the Chicago-like brick facscia to the manicured landscape, this home...

Under Construction. Located in Winter Park. Great schools, restaurants and shops are abound. It is time to call the Weitzel your new home! Your downstairs master bedroom ...

Under Construction. Soak up all the charm of the Seaberg Floor Plan. Located in the highly sought out area of Winter Park, 32789. This premiere location is walking distan...

Under Construction. Introducing Phil Kean's latest project - The Morse + Pennsylvania Townhomes. A private enclave of high-end urban lock + leave residences comprised of ...

A truly unique and rare contemporary home in the tranquil Winter Park oasis that is Windsong! This beautiful property was built in 2011, Architectural details such as flo...

One or more photo(s) has been virtually staged. Under Construction. Welcome to your new Winter Park home to be completed before the end of the year! Quality, established ...

Large lot on prime street surrounded by multimillion dollar homes in Winter Park! Just blocks from Park Avenue and Rollins College, this property is ideal for remodeling...

Great investment property with 3 bedrooms and 1 bath. Large fenced in back yard. Located between Winter Park and College Park. Multi-Family zoning. Property sold AS-IS.

Quintessential Winter Park lakefront living at its best, an incredible opportunity to own a spectacular estate located on the shores of beautiful Lake Virginia, in close ...

Location, Location, Location. Right in the heart of Winter Park. This property is the perfect opportunity to build a new home. SOLD AS-IS. NO HOA.. Close to the Wi...

Lovely, large, spacious home in Winter Park, Florida. 4 bedrooms, 2.5 bathrooms, with bonus room, perfect for office, study, etc. This home has: plantation shutters, ceil...

MOVE RIGHT INTO THIS 5 bedroom 2 bath beautiful pool home. This home has been totally remodeled with a farm house feel. New roof, new AC, new doors and windows, fresh pai...

Charming home in desirable Winter Park! This home has been beautifully maintained and upgrades include Updated kitchen granite countertops, master bath and guest bath ren...

Located in the heart of Winter Park with close proximity to shopping, Winter Park hospital, and A rated schools.This 6,592 square foot lot is ready to build your dream ho...

Timeless and turn-key perfection. Warm and inviting! Top designer’s modern traditional personal home. Large lot 100 x 140. One owner, custom home by Bill Lynch and Slocum...

STYLISH, STUNNING AND RENOVATED TO THE NINES this 3 bedroom/2.5 bath Winter Park home has great access to Interstate 4 and both Winter Park and Orlando downtown areas. Wi...

Sprawling, Well-Built SIX Bedroom, Four & a Half Bath #4462 Square Foot Concrete Custom Estate Home with Two-Car Garage Across the Entrance from INTERLACHEN COUNTRY CLUB!...

A unique offering to say the least. Originally built in 1920, the woodwork highlights the best of lost skills retained in the massive renovation done in 2009. Sitting on...