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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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$1,750,000
$6,483/mo
Monthly Payment:
$6,483
Principal & Interest:
$6,483
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $350,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,819sq ft $621 / sq ft CND
Lot Size27,512sq ft Built2008 On Site14days
Fabulous penthouse in the heart of downtown winter park! Steps to park ave with it's world class shopping and dining. This 4th floor corner unit is finished with top quality... more
Fabulous penthouse in the heart of downtown winter park! Steps to park ave with it's world class shopping and dining. This 4th floor corner unit is finished with top quality materials throughout with wolf and subzero appliances, stone and wood flooring. A wet bar with wine cooler and refrigeration drawers. A spacious master suite with 14 foot tray ceiling, an elegant bath and a balcony. The living room features a fireplace and french doors that lead to a balcony with a gas grill and a spiral staircase up to the private roof top terrace with a fireplace and views of the winter park skyline and lake osceola. Villa siena provides you with the privacy of an intimate setting and amenities including a club room with bar, billiards, fitness center and a roof top terrace. Enjoy the downtown lifestyle without giving up the privacy, security and serenity this condo has to offer. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
Your search results are current and complete. Learn more
$3,400,000
$12,596/mo
Monthly Payment:
$12,596
Principal & Interest:
$12,596
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $680,000 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 8,342sq ft $408 / sq ft SFR
Lot Size15,570sq ft Built2004 On Site14days
Breathtaking appointments at every turn, collaboration between Maroon Fine Homes and Marquis Fine Homes offers a fully furnished classic estate on prestigious Park Avenue. Three... more
Breathtaking appointments at every turn, collaboration between Maroon Fine Homes and Marquis Fine Homes offers a fully furnished classic estate on prestigious Park Avenue. Three stories of living space includes a fully equipped gym, temperature controlled wine cellar, game room inclusive of full wet bar and pool table with four televisions, and movie theater. Nothing would be complete without a temperature-controlled lanai, summer kitchen, heated pool, spa, and outdoor fireplace. Recent additions include internet-based security cameras, copper gutters, and hurricane shutters. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$194,900
$722/mo
Monthly Payment:
$722
Principal & Interest:
$722
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $38,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,040sq ft $187 / sq ft SFR
Lot Size9,860sq ft Built1959 On Site14days
Adorable Winter Park 3 BDRM/ 2 BA home located in “A” Rated School District. Cottage-like Home features Pitched Ceilings, Neutral Tile, Crown Molding, and Neutral... more
Adorable Winter Park 3 BDRM/ 2 BA home located in “A” Rated School District. Cottage-like Home features Pitched Ceilings, Neutral Tile, Crown Molding, and Neutral Paint in Living Room and Kitchen. Just off the living room is a hallway to bedrooms. Pass by guest bathroom complete with bathtub/ shower and linen closet. Additional storage available in hall closet. Master bedroom has carpet, two closets, and bathroom with walk in shower. Two other bedrooms are carpeted with deep closets and pitched ceilings. Almost all windows have been recently replaced. Spacious kitchen offers original Real Wood cabinets, Raised Oven, and pass-through section above sink which allows for an OPEN feel. On the other side of the pass through, be surrounded natural beauty in the enclosed Florida room which also serves as a casual living/dining room combo area. Just off of the Florida room is a screened in patio as well as an unscreened concrete paver patio area on the side of the home, a perfect place to set up a grill and entertain. OVERSIZED backyard has a private and peaceful feeling to it with its lush greenery, and mature landscaping. An outdoor storage shed and utility room provides functional storage. 1-Car CARPORT. The home is simply adorable. Conveniently located in quiet neighborhood off of Horatio within a couple miles of school, several parks, and Park Avenue shopping and dining. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$229,000
$848/mo
Monthly Payment:
$848
Principal & Interest:
$848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,800 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,763sq ft $130 / sq ft SFR
Lot Size14,040sq ft Built1956 On Site14days
Traditional Sale, Over Quarter Acre Corner lot home with lots of potential. Great schools and good location. Home does need some TLC.
Traditional Sale, Over Quarter Acre Corner lot home with lots of potential. Great schools and good location. Home does need some TLC. less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity
$539,500
$1,998/mo
Monthly Payment:
$1,998
Principal & Interest:
$1,998
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $107,900 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,362sq ft $228 / sq ft SFR
Lot Size9,796sq ft Built1992 On Site14days
Move-in ready family home in the Winter Park 'Tree Streets'. Walk to Phelps Park, the Winter Park YMCA and Lakemont Elementary School. Excellent layout, the first floor flows... more
Move-in ready family home in the Winter Park 'Tree Streets'. Walk to Phelps Park, the Winter Park YMCA and Lakemont Elementary School. Excellent layout, the first floor flows from the kitchen, dining room and large family room with soaring ceilings. Updated kitchen with eat-in breakfast area connects to dining room and formal living room or den/office. New roof in 2004, new HVAC in 2007. There is a large 1st floor Master suite with direct access to the light and bright Florida room that has large windows to the completely fenced in back yard. Updated shower in the master bath. Wood burning fireplace in the family room, hardwood floors on the first floor with newer carpet in the Master. This home has been extremely well maintained and is ready to move in and enjoy the Winter Park lifestyle. less
Listing Provided Courtesy of Highlander Property Group, Inc
Popularity
$230,000
$853/mo
Monthly Payment:
$853
Principal & Interest:
$852
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $46,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,760sq ft $131 / sq ft SFR
Lot Size9,462sq ft Built1970 On Site14days
This well maintained 3 bedroom 2 full bath pool home located in beautiful Winter Park is now available! The many features include a 3 year new architectural shingle roof,... more
This well maintained 3 bedroom 2 full bath pool home located in beautiful Winter Park is now available! The many features include a 3 year new architectural shingle roof, concrete block construction, 3 car garage, separate formal living and dining areas, separate family room and large bright windows. The kitchen comes with all appliances included, has ceramic tile flooring, lots of counter space and is located right off the family room. The master bedroom is spacious and has two closets. Other features include a beautiful wood burning fireplace with stone surround and ledge and ceiling fans. The 3 car garage has an electronic door opener, laundry area with washer & dryer included, utility sink, central air conditioner and updated electrical panel. Outside features include an extra-large fenced lot located on a cul-de-sac, storage shed, resurfaced sparkling bright swimming pool and glassed Florida Room for year round use that overlooks the pool area. This is a great location with excellent high rated schools conveniently located just minutes from downtown Winter Park, most major roadways, dining, shopping, entertainment, lakes, parks, golf courses, UCF, Full Sail University & Rollins College. A MUST SEE, CALL TODAY TO SCHEDULE A SHOWING! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$339,000
$1,255/mo
Monthly Payment:
$1,255
Principal & Interest:
$1,255
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $67,800 down)
Winter Park, FL 32792
Golfside Orange County School District
4bed 3bath 2,067sq ft $164 / sq ft SFR
Lot Size10,807sq ft Built1973 On Site14days
Beautifully Renovated 4/3 Ranch Style Property in Golf Course Community! Owners have renovated this amazing property! New kitchen, new baths and new landscaping. Located on the... more
Beautifully Renovated 4/3 Ranch Style Property in Golf Course Community! Owners have renovated this amazing property! New kitchen, new baths and new landscaping. Located on the Winter Park Pines Golf Course, this property is on a gorgeous tree-lined street that is family friendly. This property features a wood burning fireplace and a large back patio with custom concrete finish with back yard large enough for a pool. Minutes from Downtown Orlando, Park Avenue and the Winter Park Village, you cannot ask for a better location to everything Orlando has to offer. less
Listing Provided Courtesy of Exit Realty Central
Popularity
$1,500,000
$5,564/mo
Monthly Payment:
$5,564
Principal & Interest:
$5,557
HOA Dues:
$7
(Based on a 30 year fixed loan at 3.75% with $300,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,293sq ft $349 / sq ft SFR
Lot Size10,449sq ft Built2006 On Site14days
Dreaming of living the Winter Park Chain of Lakes lifestyle? This luxurious Mediterranean home is located on one of the most serene canals winding out to Lake Maitland. The... more
Dreaming of living the Winter Park Chain of Lakes lifestyle? This luxurious Mediterranean home is located on one of the most serene canals winding out to Lake Maitland. The moment you walk into this home you will fall in love. Grab a bottle of wine from your temperature controlled cedar wine cellar and relax by the gorgeous travertine pool deck as you gaze out at the peaceful water. Cook up dinner in your gourmet kitchen boasting a large granite island, Sub-Zero refrigerator, Dacor range, oven and warming drawer. Enjoy your meal as you hear the soft whisper from your 700 gallon saltwater aquarium located right in your family room. Beautiful wood & travertine floors, curved hallways, lighted boat dock with lifts for both your boat and wave runners, granite summer kitchen with your own beer tap. This home has too many upgrades to list. Move into your new home before summer starts and enjoy lake living at its best! Request a showing now! less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$1,325,000
$4,909/mo
Monthly Payment:
$4,909
Principal & Interest:
$4,909
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $265,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 3,018sq ft $439 / sq ft SFR
Lot Size13,376sq ft Built1920 On Site15days
Prime location in old winter park. The perfect and highly sought-after opportunity to remodel or build on this 13,376 sf lot. This charming 1920s home is located on golfview... more
Prime location in old winter park. The perfect and highly sought-after opportunity to remodel or build on this 13,376 sf lot. This charming 1920s home is located on golfview terrace, one of the premier downtown streets of winter park. The main home with 3018 sf has brick and wood floors, pitched living and family room ceilings, and a wonderful gourmet kitchen with subzero and wolf appliances. The separate detached 1/1 apt with 564 sf makes for a great home office or a guest suite. nestled on a beautiful brick circle anchored by the beloved neighborhood park and fountain, this home is the perfect spot for paradise in winter park. Come renovate or build and enjoy the walk to park ave lifestyle. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$485,000
$1,796/mo
Monthly Payment:
$1,796
Principal & Interest:
$1,796
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $97,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,520sq ft $319 / sq ft SFR
Lot Size4,482sq ft Built2005 On Site15days
Walk to Rollins, Park Avenue and many charming shops and restaurants while enjoying a tucked away, private, low maintenance home in the heart of Winter Park. Quality... more
Walk to Rollins, Park Avenue and many charming shops and restaurants while enjoying a tucked away, private, low maintenance home in the heart of Winter Park. Quality construction abounds in this spacious home with a Chicago brick fireplace, 10 ft. ceilings, extensive use of crown mold, ample windows for lots of natural light, spacious closets, cozy front porch, solid six panel colonial doors, and a well appointed staircase with nice detail. Large downstairs master suite with , double closets & sinks in the master bath with gentleman height vanity. Eat in space in the kitchen with corner windows overlooks a charming covered back porch and the kitchen features granite counter tops, warm upgraded wood cabinetry, and stainless appliances with a huge utility room for the washer and dryer and a one car garage. Well maintained and move in ready. Room sizes approx. less
Listing Provided Courtesy of Colonialtown Realty
Popularity
$395,000
$1,463/mo
Monthly Payment:
$1,463
Principal & Interest:
$1,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,345sq ft $294 / sq ft SFR
Lot Size10,509sq ft Built1958 On Site15days
Nice part of Winter Park (32789), right down the street from Windsong. Original beautiful hardwood floors. Remodeled kitchen, and large deck. Dream... more
Nice part of Winter Park (32789), right down the street from Windsong. Original beautiful hardwood floors. Remodeled kitchen, and large deck. Dream location, 5 minutes from fabulous Park Avenue. Very cute home in great location near schools, restaurants, and shopping. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School. 3/2, spacious bedrooms, large kitchen, great yard. Great neighborhood, very friendly neighbors, and central to stores and easy access to downtown. Beautiful shady, canopied street. less
Listing Provided Courtesy of Spencer Realty Professionals
Popularity
$860,000
$3,186/mo
Monthly Payment:
$3,186
Principal & Interest:
$3,186
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $172,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,232sq ft $266 / sq ft SFR
Lot Size10,007sq ft Built2015 On Site15days
New home construction!! Beautiful custom built home pre-construction, just starting construction. This two story 4 bedroom 5 bath home features a great-room, media-room and a... more
New home construction!! Beautiful custom built home pre-construction, just starting construction. This two story 4 bedroom 5 bath home features a great-room, media-room and a loft! Perfect family home! This open floor plan lives even larger with the outdoor patio and summer kitchen to enjoy your included pool!! less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$129,900
$938/mo
Monthly Payment:
$938
Principal & Interest:
$481
HOA Dues:
$457
(Based on a 30 year fixed loan at 3.75% with $25,980 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 939sq ft $138 / sq ft CND
Lot Size1.4acre Built1985 On Site15days
Gorgeous and recently renovated 2/2 condo in great area of Winter Park! Light and bright, move-in ready end unit. All stainless appliances, granite, new cabinets, wood burning... more
Gorgeous and recently renovated 2/2 condo in great area of Winter Park! Light and bright, move-in ready end unit. All stainless appliances, granite, new cabinets, wood burning fireplace, ceiling fans, fixtures, carpet throughout except tile in wet areas. Convenient to shopping (walk to Publix), area restaurants, 5 minutes to Park Ave. Tile roofs were just replaced and buildings painted. Screened patio balcony with extra storage room. Assigned parking space and ample guest spaces as well. Community has gate out the back (residents only) to access traffic light for easy in and out of the community. less
Listing Provided Courtesy of Aig Realty Services Llc
Popularity
$499,900
$2,504/mo
Monthly Payment:
$2,504
Principal & Interest:
$1,852
HOA Dues:
$652
(Based on a 30 year fixed loan at 3.75% with $99,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,734sq ft $288 / sq ft CND
Lot Size1,670sq ft Built1971 On Site15days
PRIME Downtown Winter Park 3 Bedroom 2 Bath CONDO...with views of LAKE OSCEOLA, HEATED POOL and PUTTING GREEN. Large Living Room with Electric Fireplace, Dining Area... Enclosed... more
PRIME Downtown Winter Park 3 Bedroom 2 Bath CONDO...with views of LAKE OSCEOLA, HEATED POOL and PUTTING GREEN. Large Living Room with Electric Fireplace, Dining Area... Enclosed Porch off 3RD Bedroom/Office, Open Balcony, Spacious Two Bedrooms....either could be the Master...Lots of Windows(updated) and Great Light. Private End Unit with Three Exposures....East, West and North. Covered Parking Space. Boat Slips on Lake Osceola. Walking distant to Restaurants, Library. Shops, Golf Course and Parks. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$474,900
$1,759/mo
Monthly Payment:
$1,759
Principal & Interest:
$1,759
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $94,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,033sq ft $234 / sq ft SFR
Lot Size15,367sq ft Built1969 On Site16days
Absolutely beautiful 4 Bedroom/3 Bath, 2 car garage home in a quiet, desirable Winter Park residential neighborhood. Modern, recently updated (2011 -2014) home with contemporary... more
Absolutely beautiful 4 Bedroom/3 Bath, 2 car garage home in a quiet, desirable Winter Park residential neighborhood. Modern, recently updated (2011 -2014) home with contemporary facilities and mature landscaping and added lot size. This open, spacious home features Spanish tile flooring throughout, and hardwood floors in a Master Bedroom. Extensive renovations include: kitchen, bathrooms, lighting, electrical/data, woodwork, paint inside and out, pool, landscaping and much more. Master Bedroom suite has a 2-room walk-in closet, beautiful french doors (in the Living room as well) that lead to the spacious, screened pool area. Master 2 en-suite Bathroom (Jack & Jill Shower) and Second Bathroom feature dual sinks and stand up shower with a modern style. Stunning kitchen features: stainless steel appliances (Whirlpool), kitchen island, gas 36" 5 burner range/oven with hood , granite countertops, custom cabinetry, custom lighting and plenty of counter and storage space. Security system with security screens on all windows. Spacious screened pool area is perfect for relaxation and family gatherings with some privacy of the fenced backyard. In-ground, salt-water pool with custom BeadCrete lining finish and programmable LED lighting. (Patio table stays with the home). This home is conveniently located near YMCA, close to shopping centers, Park Ave and all the major roads. SCHEDULE YOUR SHOWING TODAY !!! *** Curtains, Wine fridge & Water Filter DO NOT CONVEY WITH THE HOME... Washer/Dryer are Negotiable *** less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
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ZipRealty helps you find current homes for sale in Winter Park, FL. We show up to 30% more MLS listings than other websites, including new homes for sale, condos for sale, townhomes for sale, foreclosed homes for sale and land for sale. Set up your unique Winter Park real estate search criteria to see results that match what you're looking for. Explore maps, photos, schools and more to get an idea of what your life would be like in a new neighborhood. Find a local Winter Park real estate agent to work with by reading realtor reviews left by buyers and sellers like you. If you want to know what your home is worth, you can instantly view home values for any address by visiting our Seller Center. If you're planning to sell your home, you can also see how much similar homes are selling for in Winter Park to get an idea of how to price your home.
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid Florida Regional MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid Florida Regional MLS. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid Florida Regional MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

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Data last updated: Tuesday, March 31, 2015 at 8:45 PM