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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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$935,000
$3,464/mo
Monthly Payment:
$3,464
Principal & Interest:
$3,464
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $187,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,499sq ft $267 / sq ft SFR
Lot Size14,976sq ft Built1936 On Site111days
Just Reduced!!! Gorgeous 1930’s two story character home in the heart of Winter Park on a quiet tree lined brick street. White panel siding, green Board and Batten... more
Just Reduced!!! Gorgeous 1930’s two story character home in the heart of Winter Park on a quiet tree lined brick street. White panel siding, green Board and Batten shutters, and a gated driveway all lend to this home’s amazing curb appeal. Stunning interior offers five bedrooms, three and one-half baths, a formal living room, separate den and/or office, and family room. Master suite is overly spacious and features a wood burning fireplace and en suite, complete with a large soaking tub, shower, and expansive walk-in closet. Downstairs guest suite has private bath and could easily be enclosed to serve as a guest wing. Kitchen has been updated with stainless steel appliances, built-in oven, and pantry closet. Outdoor living space is extraordinary! Located on 0.34 acres the backyard is fantastic and has both an open deck and a covered patio that overlook the beautifully cared for lawn and gardens. Hardwood floors, butler’s pantry, bay windows, high ceilings, and more. Charming and delightful this house will make you feel right at home. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
We show you every available listing. Here's how
$425,000
$1,574/mo
Monthly Payment:
$1,574
Principal & Interest:
$1,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size12,734sq ft BuiltN/A On Site111days
Beautiful brick street with oversized 104' wide lot (12,733 SF)... Priced for land value with many options to move in, add on or build new on street with lots of new... more
Beautiful brick street with oversized 104' wide lot (12,733 SF)... Priced for land value with many options to move in, add on or build new on street with lots of new construction activity! Convenient to downtown Winter Park, Mead Gardens, tennis courts and Baldwin Park downtown area... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$425,000
$1,574/mo
Monthly Payment:
$1,574
Principal & Interest:
$1,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,515sq ft $281 / sq ft SFR
Lot Size12,733sq ft Built1948 On Site112days
Charming bungalow in Olde Winter Park on beautiful brick street with oversized 104' wide lot (12,733 SF)... 3 bedroom 2 bath split plan with updated bathrooms... updated kitchen... more
Charming bungalow in Olde Winter Park on beautiful brick street with oversized 104' wide lot (12,733 SF)... 3 bedroom 2 bath split plan with updated bathrooms... updated kitchen with newer cherry cabinets, granite counter tops, stainless steel appliances, and hardwood floors thru-out, sun room with slate floors... oversized 2-car garage and huge backyard. This home shows in great condition and could be purchased furnished. Priced for land value with many options to move in, add on or build new on street with lots of new construction activity! Convenient to downtown Winter Park, Mead Gardens, tennis courts and Baldwin Park downtown area... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$6,500,000
$24,082/mo
Monthly Payment:
$24,082
Principal & Interest:
$24,082
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $1,300,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
5bed 8bath 7,800sq ft $833 / sq ft SFR
Lot Size1.6acre Built1925 On Site112days
Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with... more
Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with electronic gate, motor court, four car garage, guest house, boathouse, and more. Sophisticated and elegant, the main house offers four bedrooms, three full baths, two half baths, formal living and dining rooms, family room, a Chef’s kitchen with professional grade appliances, home office, and gym. Screened in lanai, trellis covered patio, and open back porch all overlook the meticulously cared for lawn and gardens, complimented by hanging moss oaks and towering palms. Enjoy breathtaking sunset views over the estate’s rolling hills. Originally built in 1925, this is a very rare opportunity to own one of Winter Park’s most significant estates, offering exclusive privacy and priceless lakefront views. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$79,900
$541/mo
Monthly Payment:
$541
Principal & Interest:
$296
HOA Dues:
$245
(Based on a 30 year fixed loan at 3.75% with $15,980 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,151sq ft $69 / sq ft CND
Lot Size1.4acre Built1984 On Site112days
Perfectly located in the Winter Park Community of Hidden Oaks, 2 story spacious townhouse style condo with 3 bedrooms and 2.5 bathrooms and 1,151 square feet. Full kitchen with... more
Perfectly located in the Winter Park Community of Hidden Oaks, 2 story spacious townhouse style condo with 3 bedrooms and 2.5 bathrooms and 1,151 square feet. Full kitchen with dinette and fenced patio for privacy, living room with nice tile and wet bar and all bedrooms upstairs. Conveniently located with access to shopping, dining and major access roads, A rated schools and great for someone attending the University of Central Florida or Full Sail. less
Listing Provided Courtesy of Coldwell Banker Ackley Realty
Popularity
$210,000
$778/mo
Monthly Payment:
$778
Principal & Interest:
$778
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
2bed 3bath 1,236sq ft $170 / sq ft CND
Lot Size1,431sq ft Built1984 On Site113days
Completely renovated condo. Beautiful 5 inch Ashwood flooring throughout. Wood staircase with cherrywood spindles and oak handrails. Hardwood molding in every room. New... more
Completely renovated condo. Beautiful 5 inch Ashwood flooring throughout. Wood staircase with cherrywood spindles and oak handrails. Hardwood molding in every room. New appliances with maple cabinets in kitchen with marble flooring and counter tops. Two pantries allows for tons of storage. The home has been replumbed. All ceilings are knockdown plaster. New AC and air handler. New storm door being installed on the front door. New England slate flooring on the porch which has been rescreened. All windows have new screens. Nothing has been ignored in this remodel. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32792
Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size29,481sq ft BuiltN/A On Site113days
Paradise for sale – location extraordinaire…a world you never thought could exist, could be yours for that new lakefront home and a water-loving family. This... more
Paradise for sale – location extraordinaire…a world you never thought could exist, could be yours for that new lakefront home and a water-loving family. This winter park private lakefront lot offers approximately .68 buildable acres and .23 riparian right acres for a total close to an acre of private paradise. Lot measures: front: 108 x 232 x lakefront: 82 x 244. Many large estate homes (over 6,000 square feet) are being built on the few lakefront lots left on bear gully lake. This hidden winter park gem, is just enough out-of-the-way of the busy town, but close to highways, airport, private schools, shopping and dining on park ave. The views alone are worth the price. Scenic and serene, lake breezes and birds are all you’ll hear, except maybe the occasional neighbor’s boat and skiers or paddleboarders who live on the lake itself. Lakeside suntans and siestas await you…don’t wait, call today for details, before this gem is gone!! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$200,000
$795/mo
Monthly Payment:
$795
Principal & Interest:
$740
HOA Dues:
$55
(Based on a 30 year fixed loan at 3.75% with $40,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 3bath 1,990sq ft $101 / sq ft SFR
Lot Size12,929sq ft Built1988 On Site116days
Short sale!!! Great 3 bedroom, 2.5 bath winter park home in desirable trinity bay. Huge/oversized great room with custom vaulted ceilings, wood burning fireplace and beautiful... more
Short sale!!! Great 3 bedroom, 2.5 bath winter park home in desirable trinity bay. Huge/oversized great room with custom vaulted ceilings, wood burning fireplace and beautiful tiled floor. Formal dining room adds charm to intimate dining or special guests affairs. Kitchen complete with breakfast nook overlooking the family room so you never miss any of the excitement. Master bedroom with double sinks and large walk in closet. Part of garage was converted to a 4th bedroom. Many architectural details such as plant shelving, french door and lovely front elevation. Well established community with access to lake burkett!!! You don't want to miss this one. Call today for your private viewing!!!!! less
Listing Provided Courtesy of Watson Realty Corp
Popularity
$530,000
$1,963/mo
Monthly Payment:
$1,963
Principal & Interest:
$1,963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $106,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size9,165sq ft BuiltN/A On Site116days
The location is incomparable as it is uniquely located directly on the Winter Park golf course. This character home boasts five bedrooms, three and one-half baths, wood burning... more
The location is incomparable as it is uniquely located directly on the Winter Park golf course. This character home boasts five bedrooms, three and one-half baths, wood burning fireplace and two car garage. Downstairs master suite overlooks golf course and has a claw foot bath tub. Upstairs features four bedrooms plus a bonus room. Enjoy watching golfers play from the wrap around porch. Great opportunity to build your dream home or renovate existing home and be one of the only homes on the golf course. This lot is approx 76 X 120, .21 acres, 9156 square feet. Ask listing agent for more details regarding the adjacent land as it is not part of this parcel. Property currently has a long term tenant and term is flexible although current owner has committed to tenant through June 1, 2016. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$649,000
$2,404/mo
Monthly Payment:
$2,404
Principal & Interest:
$2,404
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $129,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,340sq ft $277 / sq ft SFR
Lot Size8,004sq ft Built1941 On Site117days
Timeless Winter Park Cape Cod treasure displays the charm of 1940’s combined with the updates of today. The 2 DWELLING PROPERTIES have so much to offer while being so... more
Timeless Winter Park Cape Cod treasure displays the charm of 1940’s combined with the updates of today. The 2 DWELLING PROPERTIES have so much to offer while being so close to Park Ave. The main living quarters, with 1,780sqft, has 3 beds/2 beds, a den/office, and a sun room. DOWNSTAIRS master bedroom includes custom shelving for his and her closets. The detached 1 Bed/1 Bath RENTAL APARTMENT is located above the oversized two car garage with 560 ft.². The bright apartment can fit so many needs: rental, guest quarters, private office, or retreat…with 1 large bedroom, walk-in closet, washer and dryer, and open kitchen to the family room. They historical home has had many renovations and updates over the years. Kitchen includes granite counter , SS refrigerator, and eat in dinette area, overlooking the private backyard. Wood floors and crown molding flow through the entire home. Enjoy the cozy sun room, wrapped in windows, with a gas fireplace and French door to the side patio. Relax on the back Trex deck, watch the Koi pond /fountain, or swim in the pool. The oversized 2 car garage includes a rear 3rd garage door to access tools in the workbench area. Located behind Rollins College this home is a short distance to Park Avenue. See the real virtual tour for more photos. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$525,000
$1,945/mo
Monthly Payment:
$1,945
Principal & Interest:
$1,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $105,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,737sq ft $302 / sq ft TWN
Lot Size2,860sq ft Built2016 On Site117days
Pre-Construction Winter Park’s newest Contemporary townhouse collection - The Wisteria Townhouses are beautifully designed by renowned architect and National... more
Pre-Construction Winter Park’s newest Contemporary townhouse collection - The Wisteria Townhouses are beautifully designed by renowned architect and National Custom Home Builder of the Year, Phil Kean Designs. This WAYCOOL Homes by Phil Kean project is a collection of 3 attractive contemporary homes, located on a brick street walking distance to Park Avenue, Hannibal Square and Rollins College. Each 3 bedroom, 2.5 bath unit offers the classic PKD open-air foyer and courtyard, an open concept floor plan with walls of glass sliding doors for indoor/outdoor living, a spacious master suite with a large walk-in closet and a 2-car attached garage. Don’t miss this unique opportunity to own this Fee Simple common wall home, set in a quiet, urban location with easy access to downtown Winter Park & Orlando, Maitland & Baldwin Park. less
Listing Provided Courtesy of Phil Kean Real Estate Llc
Popularity
$525,000
$1,945/mo
Monthly Payment:
$1,945
Principal & Interest:
$1,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $105,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,737sq ft $302 / sq ft TWN
Lot Size4,070sq ft Built2016 On Site117days
Pre-Construction Winter Park’s newest Contemporary townhouse collection - The Wisteria Townhouses are beautifully designed by renowned architect and National... more
Pre-Construction Winter Park’s newest Contemporary townhouse collection - The Wisteria Townhouses are beautifully designed by renowned architect and National Custom Home Builder of the Year, Phil Kean Designs. This WAYCOOL Homes by Phil Kean project is a collection of 3 attractive contemporary homes, located on a brick street walking distance to Park Avenue, Hannibal Square and Rollins College. Each 3 bedroom, 2.5 bath unit offers the classic PKD open-air foyer and courtyard, an open concept floor plan with walls of glass sliding doors for indoor/outdoor living, a spacious master suite with a large walk-in closet and a 2-car attached garage. Don’t miss this unique opportunity to own this Fee Simple common wall home, set in a quiet, urban location with easy access to downtown Winter Park & Orlando, Maitland & Baldwin Park. less
Listing Provided Courtesy of Phil Kean Real Estate Llc
Popularity
$625,273
$2,451/mo
Monthly Payment:
$2,451
Principal & Interest:
$2,316
HOA Dues:
$135
(Based on a 30 year fixed loan at 3.75% with $125,055 down)
Winter Park, FL 32792
6bed 4bath 5,111sq ft $122 / sq ft SFR
Lot Size9,000sq ft Built2015 On Site118days
Brand New Energy-Efficient home ready for move in now! This Del Rio features a spacious kitchen with large center island, granite countertops, walk in pantry and eat in... more
Brand New Energy-Efficient home ready for move in now! This Del Rio features a spacious kitchen with large center island, granite countertops, walk in pantry and eat in breakfast nook all open to the welcoming Family room. Enjoy family dinners in the formal Dining room and coffee and dessert in the Living room. The secluded first floor master suite, complete with huge walk-in closet and spa-like master bath with soaking tub and separate shower and his and hers vanities. The additional bedrooms each have walk in closets for that much needed extra storage space. Enjoy family fun nights in the Game room and highly sought after Media room. lake, boat dock and Seminole community parks as well as A-rated schools minutes away. For added convenience the laundry room is located on the second floor as well. Love life living at Lakeside with Known for their energy efficient features, our homes help you live a healthier & quieter lifestyle while saving you thousands of dollars on your utility bills. less
Listing Provided Courtesy of Meritage Homes Of Fl Realty
Popularity
$150,000
$555/mo
Monthly Payment:
$555
Principal & Interest:
$555
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $30,000 down)
Winter Park, FL 32792
Orange County School District
2bed 1bath 912sq ft $164 / sq ft SFR
Lot Size8,301sq ft Built1958 On Site118days
2 bed/1 bath single family home in sought after Winter Park, FL. Room sizes are approximate and are to be confirmed by buyer. Tenant in place. Minimum 24-48 hr. notice... more
2 bed/1 bath single family home in sought after Winter Park, FL. Room sizes are approximate and are to be confirmed by buyer. Tenant in place. Minimum 24-48 hr. notice required. This property is a Diamond in the Rough and does need some work. less
Listing Provided Courtesy of Gagnon Re Investments Llc
Popularity
$1,185,000
$4,390/mo
Monthly Payment:
$4,390
Principal & Interest:
$4,390
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $237,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,661sq ft $324 / sq ft SFR
Lot Size9,565sq ft Built2010 On Site118days
Built by Feely Developments in 2010 this spacious Mediterranean home is located in a highly sought after neighborhood of Winter Park on a street with almost all new construction... more
Built by Feely Developments in 2010 this spacious Mediterranean home is located in a highly sought after neighborhood of Winter Park on a street with almost all new construction homes. The private Master Quarters downstairs features an oversized custom walk-in closet, garden bath, shower, and his and her sinks. This home has an array of social areas on both levels and large windows to let the light enter each purposefully designed space and to look out over the meticulously landscaped yard. A mix of travertine a wood floors guides you to each section of the home. The chefs’ kitchen, with double islands, farmhouse style sink, and stainless Thermador appliances, is all open to the breakfast room living room side yard and porch. The upstairs bedrooms each feature custom walk-in closets and private bathrooms with a shared living room. Just a short walk to the restaurants on Park Avenue and an easy drive to the upcoming new Whole Foods Marketplace. less
Listing Provided Courtesy of Parkland International Realty
Popularity
16 17 18 19 20 21 22 23 24 ... 29
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
Website provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid-Florida Regional Multiple Listing Service 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 Multiple Listing Service. 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 Multiple Listing Service. 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.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

Copyright 2015 Mid-Florida Regional Multiple Listing Service. All rights reserved.

Data last updated: Monday, August 31, 2015 at 6:21 AM. Properties in listings may have been sold or may no longer be available.