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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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$959,000
$3,586/mo
Monthly Payment:
$3,586
Principal & Interest:
$3,553
HOA Dues:
$33
(Based on a 30 year fixed loan at 3.75% with $191,800 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 4,383sq ft $219 / sq ft SFR
Lot Size17,822sq ft Built1980 On Site145days
This Stately Red Brick home in the sought after City of Winter Park boasts over 4300 sq.ft. with a price per square foot under $219! This home will not last! 5... more
This Stately Red Brick home in the sought after City of Winter Park boasts over 4300 sq.ft. with a price per square foot under $219! This home will not last! 5 Bedrooms 4 Baths, 2 Bonus rooms and/or Offices plus an open Fitness room with an Abundance of Natural Light. Master Suite with Balcony overlooking Beautiful Screened Pool Area with Brick pavers and Summer Stainless Steel Kitchen. Hardwood and Custom Slate floors. Open Gourmet Kitchen with 48" 6 Burner Thermador Gas Range, Sub-Zero Refrigerator, built-in Granite Breakfast area opens to Dinning room and Wine Bar with Wine Cooler. Separate Formal Living and Large Family Room. Located in wonderful neighborhood on a Tree Lined street conveniently close to the "A Rated" Winter Park schools. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
We show you every available listing. Here's how
$319,900
$1,185/mo
Monthly Payment:
$1,185
Principal & Interest:
$1,185
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,980 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,820sq ft $176 / sq ft TWN
Lot Size8,532sq ft Built2014 On Site145days
Gorgeous "Brand New" Back Unit Colonial style 3 Bedroom/2 1/2 bath townhome with 1,820 sq ft located in the Winter Park Pines area, near Winter Park Memorial Hospital, Ward Park... more
Gorgeous "Brand New" Back Unit Colonial style 3 Bedroom/2 1/2 bath townhome with 1,820 sq ft located in the Winter Park Pines area, near Winter Park Memorial Hospital, Ward Park and convenient shops and restaurants on Aloma Ave., including Publix and Whole Foods. Only about 5 min. to Rollins College and Full Sail and about 15 min. to UCF. Most outstanding features include: 42" high Wood-Like European Style Kitchen Cabinets with Granite Countertop, Stainless Steel Appliances, incl. Refrigerator, 10' Ceiling - 1st Floor, Tile Floor Downstairs, High Quality Wood-like Laminate Floor Upstairs, Porch and Balcony. An Association will be formed, comprised of all unit owners. The Association will only be responsible for paying the water and electric bill to run the common areas (with reimbursement from all unit owners) and for maintaining/repairing the driveway, irrigation and septic, when needed. Lot size, parcel ID and legal description specified are subject to change once the 2 units in the building are individually recorded in Orange County. Note: Sale reflected in 2012 was for the vacant land. less
Listing Provided Courtesy of Kilsy J Vargas
Popularity
$139,900
$518/mo
Monthly Payment:
$518
Principal & Interest:
$518
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $27,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,168sq ft $120 / sq ft SFR
Lot Size8,911sq ft Built1960 On Site146days
*Back on the market. The buyer walked away!* HERE'S YOUR CHANCE! MOTIVATED SELLER! LET'S MAKE A DEAL! CHARMING EAST WINTER PARK HOME LOCATED ONLY MINUTES FROM ROLLINS COLLEGE,... more
*Back on the market. The buyer walked away!* HERE'S YOUR CHANCE! MOTIVATED SELLER! LET'S MAKE A DEAL! CHARMING EAST WINTER PARK HOME LOCATED ONLY MINUTES FROM ROLLINS COLLEGE, PARK AVENUE, UNIVERSITY OF CENTRAL FLORIDA, RESTAURANTS, BANKING, RETAIL SHOPPING & OTHER ATTRACTIONS. MAJOR ROADS IN THE IMMEDIATE AREA INCLUDE SR-436/SEMORAN BLVD, SR-417, COLONIAL DR & SR-408. HOME FEATURES CERAMIC TILE FLOORING, 1 CAR CARPORT, SPACIOUS REAR YARD, CEILING FANS, & WOODEN KITCHEN CABINETS. SOLD AS-IS, WHERE-IS. NO SELLER’S DISCLOSURES. SELLER IS MAKING NO WARRANTIES OR REPRESENTATIONS OF PROPERTY CONDITION. ROOM DIMENSIONS ARE APPROXIMATE & SHOULD BE INDEPENDENTLY VERIFIED. PROOF OF FUNDS/PRE-APPROVAL LETTER REQUIRED WITH ALL OFFERS. BUYING PARTY IS RESPONSIBLE FOR VERIFYING WHETHER OR NOT PROPERTY CONDITION WILL QUALIFY FOR BUYER’S SPECIFIC LOAN PROGRAM. HOA DUES ARE SUBJECT TO CHANGE & SPECIAL ASSESSMENTS & MUST BE VERIFIED BY BUYER. less
Listing Provided Courtesy of Real Estate Asset Disposition
Popularity N/A
$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 Site148days
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
$400,000
$1,481/mo
Monthly Payment:
$1,481
Principal & Interest:
$1,481
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $80,000 down)
Winter Park, FL 32789
2bed 2bath 2,120sq ft $189 / sq ft CND
Lot Size5,007sq ft Built1964 On Site148days
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
$950,000
$3,519/mo
Monthly Payment:
$3,519
Principal & Interest:
$3,519
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $190,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,766sq ft $199 / sq ft SFR
Lot Size15,396sq ft Built2014 On Site148days
Stunning modern Mediterranean with a private courtyard design and very bright-open floor plan. Quality finishes thru-out including marble floors, high decorative ceilings,... more
Stunning modern Mediterranean with a private courtyard design and very bright-open floor plan. Quality finishes thru-out including 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 16 guests or more. This unique courtyard style home has an enclosed swimming pool with waterfall as the central feature 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... The seller has provided some possible floor plan modification options as well - Please see on MLS "pdf attachments" for further review to demostrate flexibility of the home design... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,135,900
$4,208/mo
Monthly Payment:
$4,208
Principal & Interest:
$4,208
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $227,180 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,981sq ft $285 / sq ft SFR
Lot Size13,917sq ft Built2014 On Site149days
Open Sun Mar 29, 1pm-4pm
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
$1,949,000
$8,639/mo
Monthly Payment:
$8,639
Principal & Interest:
$7,220
HOA Dues:
$1,419
(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 Site149days
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
$360,000
$1,333/mo
Monthly Payment:
$1,333
Principal & Interest:
$1,333
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $72,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,503sq ft $240 / sq ft SFR
Lot Size9,690sq ft Built1959 On Site149days
New price!!! Beautiful tree lined street welcomes you to this charming 3 bedroom/2 bath split plan home: original hardwood floors & brand new kitchen w new... more
New price!!! 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
$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 Site149days
Winter park classic!!! Main house features 3 bedrooms and 2 baths plus a 1 bedroom 1 bath in-law suite with access from the main house. This home has it all with a gourmet... more
Winter park classic!!! Main house features 3 bedrooms and 2 baths plus a 1 bedroom 1 bath in-law suite with access from the main house. 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
$117,900
$741/mo
Monthly Payment:
$741
Principal & Interest:
$436
HOA Dues:
$305
(Based on a 30 year fixed loan at 3.75% with $23,580 down)
Winter Park, FL 32792
2bed 2bath 1,119sq ft $105 / sq ft CND
Lot Size19.0acre Built1970 On Site149days
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, 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
$879,000
$3,256/mo
Monthly Payment:
$3,256
Principal & Interest:
$3,256
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $175,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,628sq ft $334 / sq ft SFR
Lot Size6,408sq ft Built1948 On Site151days
Owner Finance Available. This is a beautiful 4 bedroom 2.5 bath Winter Park home with a 2 car garage located in Lake Knowles Terrace.
Owner Finance Available. This is a beautiful 4 bedroom 2.5 bath Winter Park home with a 2 car garage located in Lake Knowles Terrace. less
Listing Provided Courtesy of Community Realty Associates
Popularity
$309,900
$1,148/mo
Monthly Payment:
$1,148
Principal & Interest:
$1,148
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $61,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 2,358sq ft $131 / sq ft SFR
Lot Size13,547sq ft Built1986 On Site151days
This Stunning move-in ready 4 bedroom Winter Park Residence with large screened pool wont last! Seminole County A Rated Schools. Former model built by Richmond American Homes... more
This Stunning move-in ready 4 bedroom Winter Park Residence with large screened pool wont last! Seminole County A Rated Schools. Former model built by Richmond American Homes shines brightly due to the owners meticulous maintenance and the skylights and vaulted ceilings and many architectural details that make it so special. Enter into the home and be awe struck by the floor to ceiling double sided fireplace with art niches on both sides and sit awhile in the sunken conversation area while you relax by the fire on colder evenings. The split plan with pocket door closing off the guest or family wing provides privacy from the rest of the home. The light and bright Kitchen has been updated, solid surface counters, and has a unique moveable island that seats four with lots of storage and a granite top. The master suite is a genuine retreat with large sliding doors to the pool area and a huge walk-in closet. The updated master bath is spacious and with a top of the line spa tub with jets and quality plumbing fixtures adjacent to the shower with frameless doors makes this a complete oasis. Enjoy the oversized screened pool with a large covered patio for entertaining. The large yard has plenty of room for family fun! Newer energy efficient Architectural shingle roof in 2010 and much more. Ride your bike or rollerblade on the Cady Trail just 3 blocks away. Near to everything SR417, Downtown Winter Park and some key Department and Grocery stores are less than a mile away. Realtors see remarks! less
Listing Provided Courtesy of Total Realty Corp
Popularity
$569,900
$2,111/mo
Monthly Payment:
$2,111
Principal & Interest:
$2,111
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $113,980 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,730sq ft $209 / sq ft SFR
Lot Size13,988sq ft Built1972 On Site151days
This is not a short sale. Fantastic home on oversized lot with mature landscaping and access to Lake Maitland. Home features hardwood and ceramic tile throughout, a library/den... more
This is not a short sale. Fantastic home on oversized lot with mature landscaping and access to Lake Maitland. Home features hardwood and ceramic tile throughout, a library/den with custom built-ins, a wood burning fireplace, French doors and a spacious kitchen with custom cabinetry. All Information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify. Sold As-Is. less
Listing Provided Courtesy of All Florida Property Group Inc
Popularity
$2,200,000
$8,150/mo
Monthly Payment:
$8,150
Principal & Interest:
$8,150
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $440,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 5,102sq ft $431 / sq ft SFR
Lot Size20,930sq ft Built1954 On Site152days
Amazing chain-of-lakes Home on Lake Osceola, Winter Park. Enjoy breathtaking views from this stunning estate that is situated with a tiered backyard facing north. This one story... more
Amazing chain-of-lakes Home on Lake Osceola, Winter Park. Enjoy breathtaking views from this stunning estate that is situated with a tiered backyard facing north. This one story home has four bedrooms, three full bathrooms, three half baths, den and bonus room. With over 5100 square feet of living space, you will also enjoy the mature landscaped grounds, pool with summer kitchen, dock, and boat house with boat lift. A must see grand dining room with panoramic lake views perfect for entertaining. Gourmet kitchen that opens to the family room. The master, family room and dining room all have gorgeous arched windows with spectacular lake views. All rooms are generously sized. Walk to Park Avenue and experience all the shopping, dining, festivals, movies in the park and so much more! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
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.

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 2015 Mid Florida Regional MLS. All rights reserved.

Data last updated: Friday, March 27, 2015 at 5:21 AM