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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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$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 32789
Fairview Shores Orange County School District
4bed 3bath 1,701sq ft $352 / sq ft SFR
Lot Size20,863sq ft Built1953 On Site192days
Total of 6 lots already assembled with development potential in Winter Park. Future rezoning from R2 may allow mixed use opportunity. 1518 Minnesota is 3 lots with 150FF x... more
Total of 6 lots already assembled with development potential in Winter Park. Future rezoning from R2 may allow mixed use opportunity. 1518 Minnesota is 3 lots with 150FF x 140'deep with a 3/2 home providing $1150/mo income,12month lease started 5/01/14 + 1/1cottage providing $650/mo income. Only being sold together with 1516 Minnesota Ave MLS#O5308266 also 3 lots with 150FF x 140'deep with a 3/1 home providing $1000/mo income, 12mo lease started 4/01/14. Purchase this 300x140 (.96Ac) property with $2800/mo income today, hold for appreciation or future higher density development opportunity. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
We show you every available listing. Here's how
$979,000
$3,627/mo
Monthly Payment:
$3,627
Principal & Interest:
$3,627
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $195,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,634sq ft $269 / sq ft SFR
Lot Size9,774sq ft Built2014 On Site194days
Perfect family home located on a quiet tree lined cul-de-sac in the heart of Winter Park. Spacious living areas include a formal living room, dining room, and a large eat in... more
Perfect family home located on a quiet tree lined cul-de-sac in the heart of Winter Park. Spacious living areas include a formal living room, dining room, and a large eat in kitchen open to the family that is perfect for entertaining. French doors from the family room lead to a secluded and private backyard with professional landscaping. This desirable floor-plan includes a well-appointed master suite downstairs with generous closets and his and hers vanities. Upstairs there are 3 additional bedrooms plus a large bonus area that can be used as a home office, playroom or additional storage. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$849,000
$3,145/mo
Monthly Payment:
$3,145
Principal & Interest:
$3,145
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $169,800 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 3,595sq ft $236 / sq ft SFR
Lot Size14,280sq ft Built1957 On Site195days
Wonderful Home in a tucked-away area in the heart of Winter Park. Main House with 3 Bedrooms 3.5 Baths and Office/Study connected to Master Downstairs.......then GUEST/IN-LAW... more
Wonderful Home in a tucked-away area in the heart of Winter Park. Main House with 3 Bedrooms 3.5 Baths and Office/Study connected to Master Downstairs.......then GUEST/IN-LAW HOUSE w/Living Room, Bedroom, Bath, and Complete Kitchen. All very Spacious Rooms...Gourmet Kitchen opening to Family Room opening to Dining Room...all overlooking the Beautiful Screened Pool. Two Fireplaces...one in the Family Room, one in the Living Room. 2BR 2 Baths upstairs. High end appliances: Sub-Zero Refrigerator, Wolf Gas Range/Convection Oven and Bosch Dishwasher. 3-Car Garage...one with a full Bath. LAKE OSCEOLA ACCESS ACROSS THE STREET. Beautiful Landscaping/Trees. Family Room and Kitchen TVs plus Surround Sound stay. RENOVATED IN 2003 and 2006! Now it can be Yours!! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$998,000
$3,697/mo
Monthly Payment:
$3,697
Principal & Interest:
$3,697
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,600 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,767sq ft $265 / sq ft SFR
Lot Size12,059sq ft Built2014 On Site196days
The moment you walk in the front door of an Osprey Custom Home, you're drawn by the innovative, open floor plans. We encourage you to customize your home and put your personal... more
The moment you walk in the front door of an Osprey Custom Home, you're drawn by the innovative, open floor plans. We encourage you to customize your home and put your personal touch on it. Our experience allows us to offer creative suggestions that can significantly enhance the comfort and value of your new home. This home combines the timeless elegance of an estate with the amenities that today's luxury buyers expect. Please see a list of exterior appointments, energy saving features and technology, interior appointments, gourmet kitchen features, and luxury master suite features attached to Matrix. Floor plans and survey are also attached to Matrix. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$294,900
$1,113/mo
Monthly Payment:
$1,113
Principal & Interest:
$1,092
HOA Dues:
$21
(Based on a 30 year fixed loan at 3.75% with $58,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,275sq ft $130 / sq ft SFR
Lot Size13,175sq ft Built1988 On Site198days
Make this your dream home! On a corner lot,1/4+ acre, with a good size pool and screened pool enclosure with a spacious tiled porch which is great for entertaining or just... more
Make this your dream home! On a corner lot,1/4+ acre, with a good size pool and screened pool enclosure with a spacious tiled porch which is great for entertaining or just relaxing with the family. The formal and family rooms have sliding doors that make easy access to the porch and pool. Top rated seminole county schools and close to major shopping, restaurants and 417. Also close to walking and biking trail. Two large ponds with benches and ducks enhance subdivision entrance . Come and see this lovely home today ! Send in your offer. less
Listing Provided Courtesy of Cosmopolitan Home Realty Llc
Popularity
$215,000
$796/mo
Monthly Payment:
$796
Principal & Interest:
$796
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $43,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,400sq ft $154 / sq ft SFR
Lot Size9,225sq ft Built1961 On Site209days
Winter park golfer's dream home! Excellent location! This 3/2 home features its own pristine 6-hole putting green in the private back yard, mature landscaping and paver... more
Winter park golfer's dream home! Excellent location! This 3/2 home features its own pristine 6-hole putting green in the private back yard, mature landscaping and paver driveway. The living room features an exposed brick wall, beautiful terrazzo flooring throughout. The kitchen features granite counter tops and updated cabinets. Screened porch, great curb appeal with expensive palm trees. Centrally located near winter park retail shopping and restaurants and top rated schools. Call today for your private tour! less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$115,000
$669/mo
Monthly Payment:
$669
Principal & Interest:
$426
HOA Dues:
$243
(Based on a 30 year fixed loan at 3.75% with $23,000 down)
Winter Park, FL 32792
2bed 2bath 1,295sq ft $89 / sq ft CND
Lot Size1,841sq ft Built1981 On Site209days
Location! Location! This charming and well maintained 2/2 condo offers one story spacious living. Its light and bright inside, with many upgrades. This home offers vaulted... more
Location! Location! This charming and well maintained 2/2 condo offers one story spacious living. Its light and bright inside, with many upgrades. This home offers vaulted ceilings, large open great room and a formal dining room with a wet bar. There is an upgraded eat in kitchen including all appliances. The great room has a fireplace and a large sliding glass door that opens to the screened porch. The screened porch provides a cool shady retreat for relaxation an outdoor fun. Its within walking distance to shopping, supermarkets and restaurants. It has a convenient two space dedicated parking pad out front with easy access to major reads and Downtown Winter Park. Cedarwood Village is a well cared for community with a community pool and tennis courts. Don't miss this wonderful home! Owner will consider all offers. less
Listing Provided Courtesy of Watson Realty Corp
Popularity
$4,899,000
$18,150/mo
Monthly Payment:
$18,150
Principal & Interest:
$18,150
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $979,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 8,207sq ft $597 / sq ft SFR
Lot Size4.6acre Built2001 On Site212days
This exquisite lakefront gated estate custom built by Charles Clayton in 2001 is situated on an amazing 1.5 acre meticulously manicured lot with 157 ft on the shores of Lake... more
This exquisite lakefront gated estate custom built by Charles Clayton in 2001 is situated on an amazing 1.5 acre meticulously manicured lot with 157 ft on the shores of Lake Maitland of the exclusive Winter Park Chain of Lakes. Spectacular lake views and quality craftsmanship throughout . Downstairs master suite with sitting room and fireplace. Downstairs guest suite with private entrance. Rich mahogany paneled office/library with fireplace. Gourmet kitchen boasts delightful breakfast nook. Fantastic living room with 20 ft ceilings. Cozy family room has a fireplace and walk-in wet bar. Upstairs are three bedroom suites, a soundproof media room with theatre seating and state of the art electronics as well as a large bonus/game room and exercise room. Enjoy stunning sunsets year-round from the large covered lanai with screened solar and gas heated pool , fountain, spa and summer kitchen. Private boat dock and lift make this home perfect for entertaining or family living! The oversized three car garage with separate air conditioned one car garage plus additional storage building will hold your cars, boat, motorcycles and more. Absolutely no detail overlooked. Excellent Winter Park location in the heart of Olde Winter Park . CREATIVE SELLER FINANCING AVAILABLE. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$2,395,000
$9,094/mo
Monthly Payment:
$9,094
Principal & Interest:
$8,873
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $479,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,175sq ft $388 / sq ft SFR
Lot Size20,639sq ft Built2005 On Site222days
Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior... more
Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior details. Grand two-story entry with stone columns invites guests into formal living & dining areas. Polished marble flooring, high ceilings, & magnificent wrought-iron staircase, combined with Illuminating natural light give this formal living area a palatial feel. Luxury continues throughout the home & into the designer kitchen, where solid wood cabinetry with hand-carved trimming, glass doors, granite countertops, & top-of-the-line chef’s appliances make this kitchen truly inspiring. Second living room off kitchen, has gas fireplace & built-in cabinetry with walk-thru to breakfast area & wet bar. Executive office, with floor to ceiling bookshelves & tray ceiling, maintain a studious environment for the professional in this home. Extravagant, downstairs master suite features lavish, two-story, solid-wood closet. Master bath leaves little to be desired with its jetted tub, large walk-in shower, & double vanities. Upstairs provides the perfect retreat for entertaining. Billiard room, with full bar overlooks downstairs living area, & home theater makes movie night at home a cinematic event. Three of the four upstairs bedrooms are generously sized & offer full bath, walk-in closets, & walk-out balcony. Resort style pool & spa, gazebo with summer kitchen, & covered patio exemplify outdoor living at its finest. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$529,000
$1,959/mo
Monthly Payment:
$1,959
Principal & Interest:
$1,959
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $105,800 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,079sq ft $172 / sq ft SFR
Lot Size9,066sq ft Built1959 On Site223days
Fantastic Family Home! 5 bedrooms, 2 car garage, updated thru out. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well.... more
Fantastic Family Home! 5 bedrooms, 2 car garage, updated thru out. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well. Crown molding thru out. Wonderful real wood flooring. Master upstairs has an additional space being used as an office. Back yard is private and has plenty of room for a pool if buyer needed. Winter Park Schools! 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
5bed 3bath 3,756sq ft $265 / sq ft SFR
Lot Size11,239sq ft Built2006 On Site223days
Have you been searching for a unique Winter Park residence that offers you luxury living without the restrictions of a Homeowner's Association? Built in 2006, this expansive yet... more
Have you been searching for a unique Winter Park residence that offers you luxury living without the restrictions of a Homeowner's Association? Built in 2006, this expansive yet intimate villa will remind you of a castle. Boasting over 3,700 square feet, this property offers four bedrooms with two and a half bathrooms. You'll notice no detail has been spared, from arched doorways, Brazilian rosewood floors, back-lit tray ceilings, to a Venetian plaster wall treatment. This custom-built beauty offers a versatile floor plan with numerous bonus rooms, including a "man cave" with a coffered wood ceiling, and a study on the first floor. Tuscan half-columns flank the family room, which offers views of the sparkling Gothic-style pool and outdoor kitchen area. Functional and beautiful, the gourmet kitchen offers an abundance of space, a butcher block island, contrasting wood cabinets, stainless steel and gas appliances, and a walk-in pantry. The Master Suite includes plenty of space for oversized bedroom furniture and more! As you make your way into the Master Bathroom, you'll find that it boasts travertine tile, double sinks, a garden tub, walk-in shower and a large walk-in closet. Upstairs you will find plenty of closet space within each of the bedrooms. The study could easily be converted into a fifth bedroom. Located on a coveted corner lot across from Marvin Smiley Park, you'll enjoy park views and added privacy. Close to Florida Hospital and Park Avenue this location cannot be beat! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$914,691
$3,388/mo
Monthly Payment:
$3,388
Principal & Interest:
$3,388
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $182,938 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,084sq ft $297 / sq ft SFR
Lot Size9,884sq ft Built2014 On Site224days
Take advantage of our $10,000 Home Discount! And we’ll pay $7,500 towards your closing costs when you use our preferred lander and Title Company! But hurry, home must... more
Take advantage of our $10,000 Home Discount! And we’ll pay $7,500 towards your closing costs when you use our preferred lander and Title Company! But hurry, home must close on or before March 31, 2015! Come home to this brand new energy efficient home in the heart of Winter Park! A side-entry garage increases the appeal of the front exterior style. An open floor plan with large lanai make this home great for entertaining. Stainless Steel GE Monogram appliances make the kitchen ready for a gourmet meal. Gorgeous hardwood flooring stretches across the living areas, kitchen, and stairs into the upstairs retreat area. Relax in the spa-like master bath featuring a free-standing tub and rain showerhead in the shower. Home to be ready Spring/Summer 2015! Set your appointment to see today! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$289,000
$1,070/mo
Monthly Payment:
$1,070
Principal & Interest:
$1,070
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $57,800 down)
Winter Park, FL 32792
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size3.5acre BuiltN/A On Site226days
Prime vacant land. 3.5 acres + ½ acre pond. Zoned a-2. Sold as-is. Close to ucf, 417, colonial dr, university blvd., 408 and area attractions.
Prime vacant land. 3.5 acres + ½ acre pond. Zoned a-2. Sold as-is. Close to ucf, 417, colonial dr, university blvd., 408 and area attractions. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity N/A
$269,900
$999/mo
Monthly Payment:
$999
Principal & Interest:
$999
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,432sq ft $188 / sq ft SFR
Lot Size9,563sq ft Built1957 On Site234days
Reduced!!!Winter Park Charmer, looking for a gorgeous, move-in-ready home with everything brand new in the city of Winter Park. In this quiet street, this home was just... more
Reduced!!!Winter Park Charmer, looking for a gorgeous, move-in-ready home with everything brand new in the city of Winter Park. In this quiet street, this home was just completely renovated. It has is it all including a new roof, new double pane glass, low E windows, designer Kitchen with brand new cabinets, granite, stainless appliances, electric panel upgraded to include bathrooms, kitchen and family room. 2 Elegant new bath rooms with vanities , granite and Porcelain tile, new lighting, the original red oak hardwood floors have been completely redone, new interior doors with new hardware, upgraded base boards with crown molding, new drywall texture, exterior/interior paint, new Seville sod and upgraded front lawn landscape package, has a well and irrigation system, laundry with extra storage, renovated backyard shed for storage add to this a 1 car garage, new door with opener. Newer A/C, Newer plumbing. The "Huge" backyard (can be your blank canvas) easily accommodates a pool with extra space for a swing set, the existing shed and much more. If not the best, it is one of the best lots in the neighborhood. No HOA. A rated Winter Park schools, Walk to the YMCA, Whole Foods. Close to shopping and dining on Park Ave, Rollins College and Winter Park Hospital. Stop by ASAP to see this before it's snatched up!! less
Listing Provided Courtesy of Equitypoint Properties Llc
Popularity
$159,900
$592/mo
Monthly Payment:
$592
Principal & Interest:
$592
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $31,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,232sq ft $130 / sq ft SFR
Lot Size24,877sq ft Built2014 On Site235days
Extra large centrally located property with brand new manufactured home. Fully landscaped, fenced, concrete drive. Country setting near all city conveniences. Space for large... more
Extra large centrally located property with brand new manufactured home. Fully landscaped, fenced, concrete drive. Country setting near all city conveniences. Space for large garage/shop for a business plus parking for your rv or boat. Unique property for this city location. A must see if you are looking for open space without losing convenience. less
Listing Provided Courtesy of Travis Sawchuk Commercial 1st
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.

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Data last updated: Tuesday, January 27, 2015 at 9:50 PM