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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$1,509,000
$6,870/mo
Monthly Payment:
$6,870
Principal & Interest:
$5,590
HOA Dues:
$1,280
(Based on a 30 year fixed loan at 3.75% with $301,800 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,291sq ft $659 / sq ft CND
Lot Size13,765sq ft Built2008 On Site42days
This classic style residence invites you in with warm accents and designer lighting. The large, open kitchen with an included wine refrigerator is perfect for entertaining. The... more
This classic style residence invites you in with warm accents and designer lighting. The large, open kitchen with an included wine refrigerator is perfect for entertaining. The french doors that line the walls of the living room create a Manhattan-like ambiance with the charm of Winter Park. The master bedroom is fully equipped with a grand his/her bathroom including a walk-closet efficiently designed and ready for use. This residence exudes a luxury lifestyle with all the qualities of home. less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
We show you every available listing. Here's how
$1,544,236
$7,001/mo
Monthly Payment:
$7,001
Principal & Interest:
$5,721
HOA Dues:
$1,280
(Based on a 30 year fixed loan at 3.75% with $308,847 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,450sq ft $630 / sq ft CND
Lot Size13,765sq ft Built2008 On Site42days
The Landmark is the finest, most esteemed condominium residence nestled among the high profile streets of downtown Winter Park steps from Park Avenue. The aesthetically pleasing... more
The Landmark is the finest, most esteemed condominium residence nestled among the high profile streets of downtown Winter Park steps from Park Avenue. The aesthetically pleasing and award-winning architectural design presents a European, old world style throughout each detail. This spacious second floor luxury condo has unparalleled views of downtown activity in Winter Park. The kitchen is ready to be adorned with cabinets and personal accents to create a masterpiece for the chef. This residence gives you the opportunity to create a family room, an additional 3rd bedroom, den or even an executive office. It is open, bright and ready to come alive! less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
$1,179,000
$4,368/mo
Monthly Payment:
$4,368
Principal & Interest:
$4,368
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $235,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,465sq ft $340 / sq ft SFR
Lot Size12,696sq ft Built1991 On Site45days
Modern luxury and masterful design embody this one of a kind recently renovated residence located in Winter Park's most desirable community, "The Vias". The grand 2 story... more
Modern luxury and masterful design embody this one of a kind recently renovated residence located in Winter Park's most desirable community, "The Vias". The grand 2 story entryway with custom staircase, along with both formal living and dining rooms, create a dramatic focal point. A large open kitchen with transformations granite and stainless steel appliances, adjoins a large family room with extensive windows and French doors. The main level has 3 bedrooms all with direct bath access, a large laundry room with numerous cabinets and Brazilian Mahogany flooring throughout. A private, formal living room with new French doors and custom marble wood burning fireplace with built-in bookcases create a wonderful entertainment area. The upper level master suite has large windows and French doors leading to a private deck which takes in the outstanding views of the grounds and recently renovated pool. A large bath with Jacuzzi tub and separate shower, along with a 2nd wood burning fireplace and 2 large walk-in closets (one recently renovated), round out this private oasis. The additional en suite is ideal for a guest or teen. Entertain outdoors in grand style with a very private yard with incredible pool and custom summer kitchen. Additional highlights include remote control estate gates, perimeter security camera system, irrigation system, high-efficiency Hayward pool system and completely refinished designer pool with custom stone path, pavers, outdoor shower and travertine pool deck. Expect to be impressed! less
Listing Provided Courtesy of ORLANDO LUXURY HOMES INC
Popularity
$1,100,000
$4,075/mo
Monthly Payment:
$4,075
Principal & Interest:
$4,075
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $220,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,500sq ft $314 / sq ft SFR
Lot Size14,323sq ft Built2016 On Site48days
Mark your calendar to come see this gorgeous masterpiece built Energy Efficient, located on one of the loveliest streets in Winter Park. With 3500sf of "living space" everything... more
Mark your calendar to come see this gorgeous masterpiece built Energy Efficient, located on one of the loveliest streets in Winter Park. With 3500sf of "living space" everything new. Inquire immediately to learn about pre-completion discounts, and to customize fit and finish to your heart's desire! As you walk through the magnificent 8’ double entrance doors into the open floorplan with soaring voluminous 10' ceilings throughout. This open unobstructed floorplan allows for a magical view from the front entrance direct to the pool and lanai. The elegant gourmet kitchen is expansive and has sleek solid surface counters & island with double sink and bar seating, stainless KitchenAid appliances including double ovens, a closet pantry and built-in desk, all completely open to large family room and 8’ sliding glass doors overlooking picturesque lovely backyard. The grand master bedroom and master bath offer three walk-in closets fit for a king. Fantastic location of only a 15 minute walk to the Winter Park Racquet Club and only 2 miles to Winter Park’s downtown Park Avenue. Scheduled for completion in early March 2016 don’t hesitate to pick your finishes and customize your next home. less
Listing Provided Courtesy of FLORIDA REALTY INVESTMENTS
Popularity
$899,000
$3,330/mo
Monthly Payment:
$3,330
Principal & Interest:
$3,330
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $179,800 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,332sq ft $270 / sq ft SFR
Lot Size9,701sq ft Built2002 On Site49days
Beautiful Remodeled Charmer in the heart of Winter Park. Stunning architectural design details. Originally built in 1927 & extensively renovated in 2002 & 2015. Millwork cannot... more
Beautiful Remodeled Charmer in the heart of Winter Park. Stunning architectural design details. Originally built in 1927 & extensively renovated in 2002 & 2015. Millwork cannot be compared- exquisite crown moldings, coffered ceilings, bead board & replicated embossed tin ceilings. All cabinetry & interior doors custom made. Hardie Board siding, metal roof, separate 2 car garage with office & bonus above. 4 bedrooms, 4.5 baths. Each bedroom has bathroom. Upstairs/open loft & study with custom built-ins. Home is entirely hardwood flooring. Kitchen is built for gourmet. Natural gas. Six burner Thermador range, custom hood, Jenn Air convection, Bosch dishwasher, Dacor warming drawer, wall mounted pot filler, granite counter, center island includes cherry wood & prep farmhouse sink, custom cabinetry with brushed nickel hardware. Two large pantry closets & 24 back-saver pull out drawers. Living room has one of a kind antique soapstone gas fireplace & mantel. Formal dining has 11 ft. bay windows. Custom plantation shutters throughout. Spacious master bedroom overlooking lush yard. Master bath includes jetted tub & dual head walk-in shower. Inside laundry. Impressive back deck with handcrafted pergola, cobblestone pavers & private landscaped backyard. New light fixtures, 2nd floor AC, & whole house painted in 2015, irrigation system, termite bond, security system, basement storage, double pane windows, upgraded wireless network, new white picket fence- fully enclosed. Excellent schools, walk to Park Ave, etc. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$664,900
$2,671/mo
Monthly Payment:
$2,671
Principal & Interest:
$2,463
HOA Dues:
$208
(Based on a 30 year fixed loan at 3.75% with $132,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 5bath 4,528sq ft $147 / sq ft SFR
Lot Size11,596sq ft Built2007 On Site53days
Check out this amazing Estate home in the gated community of Sanctuary at Lake Ann. The home has over 4500 square feet and is a 4 bedroom 4 bath and more. The interior includes... more
Check out this amazing Estate home in the gated community of Sanctuary at Lake Ann. The home has over 4500 square feet and is a 4 bedroom 4 bath and more. The interior includes Wood Plank Floors, Double Crown Molding, Stone, Granite, and Wrought Iron stair rails. The home has a fireplace in the living room and formal Dining room. The first floor Master Suite has access to a Covered Patio. The Secondary Bedrooms, Office with Balcony, Media Room and Guest Suite are all located on the second floor. The home has a very nice pool and a 3 car garage. less
Listing Provided Courtesy of BUYER'S & SELLER'S REALTY, INC
Popularity
$285,000
$1,055/mo
Monthly Payment:
$1,055
Principal & Interest:
$1,055
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $57,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,666sq ft $171 / sq ft SFR
Lot Size7,760sq ft Built2010 On Site54days
Beautiful 3 bedroom, 2 bathroom on a corner lot home in the desirable Winter Park- Shores of Killarney community. This newly built open floor plan home offers a spacious... more
Beautiful 3 bedroom, 2 bathroom on a corner lot home in the desirable Winter Park- Shores of Killarney community. This newly built open floor plan home offers a spacious combination living room/Dining Room with easily maintained tile flooring and is filled with natural light - great for entertaining! The kitchen features wood cabinetry, newer stainless steel appliances, granite counter tops, recessed lighting and breakfast bar. The spacious owners retreat offers two walk in closets and en suite- bathroom , granite counter tops, dual sinks and tiled shower. It has a convenient utility room inside with washer and dryer hookups. Deeded lake access, dock and ramp to Lake Killarney! Easy access to I-4, Winter Park Village, Park Ave, Downtown Orlando and College Park and NO HOA FEES!! Come and see what this lovely home has to offer. less
Listing Provided Courtesy of KELLER WILLIAMS AT THE PARKS
Popularity
$875,000
$3,241/mo
Monthly Payment:
$3,241
Principal & Interest:
$3,241
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $175,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,600sq ft $243 / sq ft SFR
Lot Size18,419sq ft Built1950 On Site55days
Open Sun Feb 14, 11am-2pm
Gorgeous home on almost a half-acre lot, walking distance to Downtown Winter Park. Remodeled with custom cabinetry, exotic granite, Brazilian wood floors, and timeless marble.... more
Gorgeous home on almost a half-acre lot, walking distance to Downtown Winter Park. Remodeled with custom cabinetry, exotic granite, Brazilian wood floors, and timeless marble. Oasis pool area with natural stone waterfall, tropical foliage, and plenty of privacy. Outdoor entertaining area off of the kitchen with partial views of Lake Mizell. Upstairs master retreat boast large closets and spacious bathroom. Upstairs is a secondary bedroom and downstairs provides two guest suites. Additional game room leading to covered Lanai is off of the foyer making great living spaces with plenty of storage. This unique property is something to see and fall in love with.a new roof will be placed . brand new appliances and AC units. less
Listing Provided Courtesy of PALMANO GROUP RE BROKERAGE LLC
Popularity
$230,000
$852/mo
Monthly Payment:
$852
Principal & Interest:
$852
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $46,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,608sq ft $143 / sq ft SFR
Lot Size9,438sq ft Built1973 On Site55days
Single story home, not far from Full Sail University.The home has three bedrooms two baths, large living room, all electric kitchen, combo dining and kitchen area. The exterior... more
Single story home, not far from Full Sail University.The home has three bedrooms two baths, large living room, all electric kitchen, combo dining and kitchen area. The exterior has been reason recently painted, new three years roof, both bath rooms have been updated, update kitchen appliances, large fence lot and large exterior storage building. Close to commercial, close to malls. Beautiful property. Detached Storage Shed In Back. less
Listing Provided Courtesy of FORSALEBYOWNER.COM REFERRAL
Popularity
$899,000
$3,351/mo
Monthly Payment:
$3,351
Principal & Interest:
$3,330
HOA Dues:
$21
(Based on a 30 year fixed loan at 3.75% with $179,800 down)
Winter Park, FL 32792
Goldenrod Orange County School District
4bed 5bath 5,329sq ft $169 / sq ft SFR
Lot Size25,253sq ft Built1984 On Site55days
Fabulous lakefront opportunity in Winter Park! This stunning custom-built pool home, which sits on private spring-fed Lake Waunatta, offers vaulted ceilings, wood floors and a... more
Fabulous lakefront opportunity in Winter Park! This stunning custom-built pool home, which sits on private spring-fed Lake Waunatta, offers vaulted ceilings, wood floors and a spacious floor plan with over 5,000 sf for entertaining and family living. Almost every room of this four bedroom, four and one half bath home offers spectacular views of the pool and lake. First floor includes a gracious formal living room and family room, enhanced by a double-sided wood burning fireplace, and a separate formal dining room off of the gourmet kitchen, which boasts a breakfast room, breakfast bar, island, stainless steel appliances, granite countertops, solid wood cabinets and generous pantry space. A very large second floor master suite with wood burning fireplace has two walk-in closets, spa bath with his and her sinks, and a breathtaking sitting room that overlooks the pool and lake. The second floor is completed with a bedroom with private bath and two additional bedrooms with a Jack-n-Jill bath. A fifth room on the first floor can be used as a mother-in-law suite, bonus room or office/den. Sunroom with floor-to-ceiling windows and Mexican tile, showcasing pool and lake views and a built-in summer kitchen with large sit down bar and wine cooler, is great for entertaining family and friends. Retreat to the boat house with lift and enjoy warm summer breezes relaxing under the gazebo. Zoned for top Winter Park schools and convenient location to Trinity Preparatory School, UCF, and Full Sail. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$995,000
$3,686/mo
Monthly Payment:
$3,686
Principal & Interest:
$3,686
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size29,111sq ft BuiltN/A On Site55days
This is a rare opportunity to build your dream home in one of the most desirable neighborhoods in Winter Park. Convenient location with easy access to Downtown Orlando, Park... more
This is a rare opportunity to build your dream home in one of the most desirable neighborhoods in Winter Park. Convenient location with easy access to Downtown Orlando, Park Avenue retail shopping district, Rollins College, Winter Park OR Downtown YMCAs, Florida Hospital, UCF, and all the amenities Winter Park and Orlando have to offer……without having to go on to I-4!!! Utilize the “A” rated Winter Park Schools. This lot is 1 house off of Lake Sue and is elevated from the street to allow lake views. Ample land to build amazing spaces indoors and out. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$299,000
$1,107/mo
Monthly Payment:
$1,107
Principal & Interest:
$1,107
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32789
Garden Acres Orange County School District
3bed 2bath 1,242sq ft $241 / sq ft SFR
Lot Size9,705sq ft Built1948 On Site56days
WinterPark Renovated MeadGardens area home just steps away from many area amenities. Enjoy this conveniently located home on an over-sized corner lot with privacy fencing hiding... more
WinterPark Renovated MeadGardens area home just steps away from many area amenities. Enjoy this conveniently located home on an over-sized corner lot with privacy fencing hiding a Pool! Updates throughout including kitchen and appliances. The home is open, light and bright with ceramic tile and wood toned laminate floors. 3 nice sized bedrooms and one with a private 1/2 bath on suite. French doors open onto the paver deck surrounding the pool. A Must See! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$166,000
$615/mo
Monthly Payment:
$615
Principal & Interest:
$615
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,200 down)
Winter Park, FL 32789
College Park Orange County School District
2bed 1bath 1,028sq ft $161 / sq ft SFR
Lot Size7,000sq ft Built1940 On Site59days
Well maintained home centrally located to everything Orlando and Winter Park have to Offer. Close to downtown Winter Park, downtown Orlando, the burgeoning Ivanhoe Village... more
Well maintained home centrally located to everything Orlando and Winter Park have to Offer. Close to downtown Winter Park, downtown Orlando, the burgeoning Ivanhoe Village district, near Dubsdread golf course and tap room. Perfect starter home or investment property opportunity. The Original hardwood floors are stunning. The seller has agreed to pay for a home warranty through American Home Shield at closing. Transferable termite bond. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$589,000
$2,182/mo
Monthly Payment:
$2,182
Principal & Interest:
$2,182
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $117,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,314sq ft $255 / sq ft SFR
Lot Size10,102sq ft Built1958 On Site59days
One story home with two master suites!! Kenilworth shores tree-lined street is the perfect setting for this 4/3 beauty. Architecturally custom curb appeal invites you into this... more
One story home with two master suites!! Kenilworth shores tree-lined street is the perfect setting for this 4/3 beauty. Architecturally custom curb appeal invites you into this beautiful home with a cheery formal foyer, gleaming hardwood floors & freshly painted interior. The updated windows & french doors at the rear of the house offers stunning natural light and a perfect view of the sparkling pool, serene covered patio & maturely landscaped backyard. A beautiful brick, wood burning fireplace is the perfect centerpiece for the spacious living room. The updated kitchen boasts a lovely breakfast bar, gas cooking & a smart built-in desk! Home was renovated to include a light & bright second master suite with vaulted ceilings plus a large inside laundry room. Extras include: 2 zone ac, attached workshop, utility sheds & custom gated carport. Brookshire, glenridge & winter park high. Welcome home!! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$319,000
$1,181/mo
Monthly Payment:
$1,181
Principal & Interest:
$1,181
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size15,364sq ft BuiltN/A On Site59days
Value is in the land! This is an oversized lot...75 x 205 (15,364 sf) located in the highly desirable "Tree Street" neighborhood of Winter Park. Build your dream home here with... more
Value is in the land! This is an oversized lot...75 x 205 (15,364 sf) located in the highly desirable "Tree Street" neighborhood of Winter Park. Build your dream home here with A rated schools and new construction all around. Conveniently located close to the YMCA, Park Avenue Retail District, Rollins College, Farmer's Market, Florida Hospital, and so much more! This lot can support up to a 5,000 sf home with 3 car garage, pool, and wonderful outdoor living spaces. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Saturday, February 13, 2016 at 7:51 PM. Properties in listings may have been sold or may no longer be available.