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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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$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
4bed 5bath 4,766sq ft $209 / sq ft SFR
Lot Size15,396sq ft Built2014 On Site50days
This stunning modern Mediterranean home has a private courtyard design with very bright-open floor plan. Quality finishes thru-out including stunning marble floors, high... more
This stunning modern Mediterranean home has a private courtyard design with very bright-open floor plan. Quality finishes thru-out including stunning marble floors, high decorative ceilings, picturesque large windows, designer lighting, impressive entry perfect for grand piano & wonderful entertaining room (47 X 27) provided with TV and projector installation. Double master bedroom suites both downstairs & upstairs, 2 fireplaces, and 2 laundry rooms. One highlight is an expansive formal dining room big enough to seat up to 16 people or more. This unique courtyard style home has an enclosed swimming pool with waterfall right in the center of the home making it perfect for entertaining! Gourmet kitchen open to family room, custom bar, marble floors thru-out, energy efficient, surround system, insulated walls and ceilings, fenced backyard, and Jacuzzi tub in master bath. There are many more custom features in this well designed home walking distance to ICC, WPRC, YMCA & Phelps Park... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
We show you every available listing. Here's how
$1,225,000
$4,538/mo
Monthly Payment:
$4,538
Principal & Interest:
$4,538
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $245,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 4,084sq ft $300 / sq ft SFR
Lot Size12,096sq ft Built2006 On Site50days
Spectacular, custom built pool home in the heart of Olde Winter Park! This stunning, traditional home features four to five bedrooms, four full baths, two half baths, and a... more
Spectacular, custom built pool home in the heart of Olde Winter Park! This stunning, traditional home features four to five bedrooms, four full baths, two half baths, and a downstairs office with fireplace, offering more than 4,000 square feet of comfortable living space. Brazilian cherry wood floors, crown molding, plantation shutters and beautiful mill-work throughout are just a few of the exquisite finishes you'll fall in the love with. The gourmet kitchen with an attached butler's pantry and spacious walk-in pantry also features a gas burner stove, built-in oven, and solid wood cabinetry with granite counters. The kitchen opens to a fantastic living room, with french doors leading out to and overlooking the covered lanai with summer kitchen and pool. Retreat into the downstairs master suite and find relaxation in the spa bath, complete with his and her vanities and walk-in shower with rainfall shower head. Walk upstairs to discover three additional bedrooms and the bonus room or fifth bedroom with its own private bath and french doors that help turn this room into the perfect creative space. Step outside to a gorgeous, fenced-in backyard with mature landscaping and 15' bamboo for extra privacy. Heated salt water pool with fountain, four-hole putting green, and playground with high-end, artificial turf all make for great recreation and entertainment. Solar heating, central vac and a home security system are other thoughtful installations. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$549,000
$2,034/mo
Monthly Payment:
$2,034
Principal & Interest:
$2,034
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $109,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,927sq ft $285 / sq ft SFR
Lot Size6,181sq ft Built2015 On Site50days
Live on one level in this new construction arts and craft single family home in the hottest new area of Winter Park. Enjoy the spacious open floor plan, fabulous kitchen, large... more
Live on one level in this new construction arts and craft single family home in the hottest new area of Winter Park. Enjoy the spacious open floor plan, fabulous kitchen, large great room, first floor grand master bedroom and guest bedrooms, and private loft. Special interior selections include wooden cabinets, granite counter tops, 7-inch wide "wooden" tile, and stainless appliances. No HOA fees. Located walking distance to Winter Park Village, Park Ave and all of the new parks, restaurants, and shopping. Upstairs bathroom optional. Fireplace optional. Summer Kitchen optional. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$450,000
$1,667/mo
Monthly Payment:
$1,667
Principal & Interest:
$1,667
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $90,000 down)
Winter Park, FL 32789
2bed 2bath 2,300sq ft $196 / sq ft CND
Lot Size5,007sq ft Built1964 On Site50days
This sophisticated Penthouse is accessed via a keyed elevator. When entering, guests step directly from the elevator into a formal dining room. The living quarters occupy the... more
This sophisticated Penthouse is accessed via a keyed elevator. When entering, guests step directly from the elevator into a formal dining room. The living quarters occupy the entire top floor of the condominium building and thus offer maximum privacy, quiet and security. A sleek and roomy kitchen, with stone counters and wood cabinets, include features that will please the serious chef or the everyday cook. Spread over 2300 sq ft of living area, the open-floor plan features a 54 ft. living room that is flanked by a 44 ft sun room that overlooks a swimming pool, a duck pond and acres of landscaped gardens. The window wall of the sun room provides spectacular views of ever-changing sunsets. (If, you're an early riser, marvelous views of sunrises can be seen through the windows at the eastern end of the penthouse.) Amenities of the 2 bedroom/2 bath home include Brazilian cherry and carpeted floors and crown molding. The inside utility room has storage cabinets and an extra refrigerator. Located in the heart of Winter Park, this unique Penthouse is within walking distance of Rollins College and Park Avenue. Ownership is 80% age 55 and older. Call listing agent for additional information. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$159,000
$829/mo
Monthly Payment:
$829
Principal & Interest:
$589
HOA Dues:
$240
(Based on a 30 year fixed loan at 3.75% with $31,800 down)
Winter Park, FL 32789
2bed 2bath 1,160sq ft $137 / sq ft CND
Lot Size5,612sq ft Built1986 On Site50days
This is great end unit condo located inside Killarney Bay Condo. Fully equipped kitchen with breakfast bar to the dining room. Large living room with high ceilings with a wood... more
This is great end unit condo located inside Killarney Bay Condo. Fully equipped kitchen with breakfast bar to the dining room. Large living room with high ceilings with a wood burning fire place and open floor plan. This condo is light and bright with freshly painted walls and brand new carpet throughout. Large indoor laundry room. Rear balcony. This condo comes with a covered parking space too. Near to Winter Park Village and the new Trader Joe's and other new businesses. less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$1,148,500
$4,255/mo
Monthly Payment:
$4,255
Principal & Interest:
$4,255
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $229,700 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,981sq ft $288 / sq ft SFR
Lot Size13,917sq ft Built2014 On Site51days
Brand new construction by Vintage Estate Homes on oversized lot situated on quiet brick street. All bedrooms and living spaces on the first floor with a 23x18 bonus room on the... more
Brand new construction by Vintage Estate Homes on oversized lot situated on quiet brick street. All bedrooms and living spaces on the first floor with a 23x18 bonus room on the 2nd floor. Quality construction with high end details throughout including large master suite with sitting area and fireplace plus huge master closet, 3 additional bedrooms downstairs – one of which is a 2nd master suite with sitting area. Downstairs office, hardwood floors, crown molding, high ceilings, Thermador gas stove, quartz counters, 2 tankless water heaters, covered outdoor patio for entertaining, 2 car garage + additional separate 1 car garage. Option for a pool for additional price if desired. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$122,000
$452/mo
Monthly Payment:
$452
Principal & Interest:
$452
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $24,400 down)
Winter Park, FL 32792
Seminole County School District
3bed 1bath 988sq ft $123 / sq ft SFR
Lot Size8,520sq ft Built1960 On Site51days
Nice Winter Park home with no HOA fees! Seller installing new AC system. Home has brick detail on the front, tile, updated kitchen and it is in good condition. Conveniently... more
Nice Winter Park home with no HOA fees! Seller installing new AC system. Home has brick detail on the front, tile, updated kitchen and it is in good condition. Conveniently located with easy access to major interstates. This is a Freddie Mac / Home Steps property. An Owner Occupant Affidavit must accompany all Owner Occupant offers. Buyer to pay DOC stamps on deed - Seller is exempt. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyers advised to verify. less
Listing Provided Courtesy of Mickey Hage Inc
Popularity
$1,949,000
$8,542/mo
Monthly Payment:
$8,542
Principal & Interest:
$7,220
HOA Dues:
$1,322
(Based on a 30 year fixed loan at 3.75% with $389,800 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,275sq ft $595 / sq ft CND
Lot Size27,512sq ft Built2008 On Site51days
Penthouse at Villa Siena. This Condominium runs along a large portion of the south facing Penthouse level. Home has 2 large Master bedroom suites and a 3rd bedroom with ensuite... more
Penthouse at Villa Siena. This Condominium runs along a large portion of the south facing Penthouse level. Home has 2 large Master bedroom suites and a 3rd bedroom with ensuite bath. Custom cabinetry in the Master bedroom provides ample storage. Home has a Large Media room for entertaining. Polished marble and wood floors run through out this spectacular space. Villa Siena is a 31 unit luxury condominium in downtown Winter Park. Building offers underground garage parking, rooftop terrace, clubroom and workout room. Sub-Zero and Wolf appliances along with high-end finishes throughout. Stone and Wood floors. Walking distance to everything Park Ave. has to offer.... less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,282sq ft $389 / sq ft SFR
Lot Size13,061sq ft Built1951 On Site51days
Stunning Winter Park lot on a tree lined, brick street. Lush 100 x 130 foot site is surrounded by million dollar homes. Walk to Phelps Park and the Winter Park YMCA. Fantastic... more
Stunning Winter Park lot on a tree lined, brick street. Lush 100 x 130 foot site is surrounded by million dollar homes. Walk to Phelps Park and the Winter Park YMCA. Fantastic opportunity to build your dream home! Please call for an appointment to walk the property. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$375,000
$1,389/mo
Monthly Payment:
$1,389
Principal & Interest:
$1,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,503sq ft $250 / sq ft SFR
Lot Size9,690sq ft Built1959 On Site51days
Beautiful tree lined street welcomes you to this CHARMING 3 Bedroom/2 Bath SPLIT plan home: Original hardwood floors & BRAND NEW kitchen w new cabinets,... more
Beautiful tree lined street welcomes you to this CHARMING 3 Bedroom/2 Bath SPLIT plan home: Original hardwood floors & BRAND NEW kitchen w new cabinets, granite counters & stainless steel appliances, & sparkling lap pool is the perfect centerpiece for your backyard oasis!! Large 14 x 16 storage room off utility room could easily be converted to a home office (included in sq ft) Extras include: NEW AC, slightly vaulted ceilings & 2 car carport PLUS Brookshire Elementary, Glenridge Middle & Winter Park High School!! Welcome Home!! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$375,000
$1,389/mo
Monthly Payment:
$1,389
Principal & Interest:
$1,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,022sq ft $185 / sq ft SFR
Lot Size10,344sq ft Built1960 On Site51days
Kenilworth shores treasure! This one owner home has been meticulously maintained! Upon entering, the open floor plan is delightful boasting a charming foyer, original hardwood... more
Kenilworth shores treasure! This one owner home has been meticulously maintained! Upon entering, the open floor plan is delightful boasting a charming foyer, original hardwood floors, & wood burning fireplace! 3 bedrooms/ 2 baths in main house plus 1 bedroom/1 bath detached guest suite (included in sq ft) steps from the beautiful backyard and sparkling lap pool. Adorable kitchen with cozy breakfast nook & built-in corner china cabinets in dining room add to the character of this beauty! Extras include: 2 car garage, mature landscaping, updated windows, attic fan plus brookshire elementary, glenridge middle & winter park high school! Welcome home! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$330,000
$1,222/mo
Monthly Payment:
$1,222
Principal & Interest:
$1,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $66,000 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 1,838sq ft $180 / sq ft SFR
Lot Size10,260sq ft Built1957 On Site51days
Winter park classic!!! Home features 3 bedrooms and 2 baths plus a 1 bedroom 1 bath in-law suite. This home has it all with a gourmet kitchen, custom cabinets, custom tile... more
Winter park classic!!! Home features 3 bedrooms and 2 baths plus a 1 bedroom 1 bath in-law suite. This home has it all with a gourmet kitchen, custom cabinets, custom tile flooring, and spacious living/dining room with sliders to open air pool with brick pavers. In-law unit has private entrance, kitchenette and full bath with lots of upgrades and direct access into the main house. Also has private brick pavered patio area and is perfect for a home office or bonus room. Large bedrooms in main house with classic baths and vintage tile. Updated electrical, a/c. Large fenced corner lot and 2-car carport. Walk to great schools, shopping, hospital, parks and the cady way trail. less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$130,000
$786/mo
Monthly Payment:
$786
Principal & Interest:
$481
HOA Dues:
$305
(Based on a 30 year fixed loan at 3.75% with $26,000 down)
Winter Park, FL 32792
2bed 2bath 1,119sq ft $116 / sq ft CND
Lot Size19.0acre Built1970 On Site51days
Enjoy the best of what Winter Park has to offer at the Four Seasons! Convenient living in this established Winter Park community. This home has been tastefully remodeled and... more
Enjoy the best of what Winter Park has to offer at the Four Seasons! Convenient living in this established Winter Park community. This home has been tastefully remodeled and waiting ready for a new owner to call it home! This beautifully maintained unit features 2 bedrooms, 2 bathrooms, separate kitchen, dining room, living room, screened room with utility closet and a carport. The Master Bedroom is very spacious and features a large walk in closet. The condo is refinished with, designer commercial grade pergo wood floors though out the family room, hallways and dining room; Master bath boast gorgeous custom vanity with reconfigured shower, Guest Bath has terracotta like tile with updated vanity and tub. Ceiling fans in all rooms and stainless steel appliances. As a resident of this beautiful community you will enjoy 3 swimming pools, tennis courts, shuffleboard and car wash area. HOA fees also include water, sewer and trash removal, ground and landscaping maintenance and pest control. This sought after community features outstanding Winter Park schools, minutes from Park Avenue, Whole Foods, Winter Park YMCA, Rollins College, Full Sail University, high end shopping and restaurants with in a minutes drive. Sq footage from tax rolls. All info intended to be accurate but can't be guaranteed. less
Listing Provided Courtesy of Realty Pros Assured Llc
Popularity
$265,000
$989/mo
Monthly Payment:
$989
Principal & Interest:
$981
HOA Dues:
$8
(Based on a 30 year fixed loan at 3.75% with $53,000 down)
Winter Park, FL 32792
Goldenrod Orange County School District
4bed 3bath 2,219sq ft $119 / sq ft SFR
Lot Size10,253sq ft Built1972 On Site52days
You Have to see this beautifully rehabbed house in a family friendly neighborhood. Great lay out and open floor plan. New Granite counter tops, marble back... more
You Have to see this beautifully rehabbed house in a family friendly neighborhood. Great lay out and open floor plan. New Granite counter tops, marble back splash and stainless steel apps in the kitchen. Master Bath is all new. Pool has been redone. Don't let this one get away. less
Listing Provided Courtesy of Investment Homes Direct Llc
Popularity
$259,900
$962/mo
Monthly Payment:
$962
Principal & Interest:
$962
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $51,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,453sq ft $179 / sq ft SFR
Lot Size9,097sq ft Built1961 On Site52days
Beautiful pool home in Winter Park. Recently remodeled with refinished original wood floors throughout, an open kitchen with stainless steel appliances and granite counters. New... more
Beautiful pool home in Winter Park. Recently remodeled with refinished original wood floors throughout, an open kitchen with stainless steel appliances and granite counters. New windows and remodeled baths. Brand new roof. Driveway and swimming pool area with brand new pavers. This home offers outstanding fenced backyard. Cozy bonus room with double pane windows facing the swimming pool. less
Listing Provided Courtesy of Varonia Real Estate, Llc
Popularity
6 7 8 9 10 11 12 13 14 ... 19 29
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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
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.

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 MLS 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 2014 Mid Florida Regional MLS. All rights reserved.

Data last updated: Friday, December 19, 2014 at 2:14 PM