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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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$795,000
$2,945/mo
Monthly Payment:
$2,945
Principal & Interest:
$2,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,381sq ft $334 / sq ft SFR
Lot Size17,514sq ft Built1955 On Site239days
Prime old Winter Park Via location. Large lot 0.41 acre. Lot has 110 feet of street frontage. Home is very good condition in a great Winter Park neighborhood.
Prime old Winter Park Via location. Large lot 0.41 acre. Lot has 110 feet of street frontage. Home is very good condition in a great Winter Park neighborhood. less
Listing Provided Courtesy of EXCLUSIVE REAL ESTATE
Popularity
Your search results are current and complete. Learn more
$195,000
$722/mo
Monthly Payment:
$722
Principal & Interest:
$722
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $39,000 down)
Winter Park, FL 32792
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size15,046sq ft BuiltN/A On Site241days
Large Beautifully Natural Lanscaped in Excellant Winter Park Neighborhood Near W.P.Hospital. Ready to Build Large Home.
Large Beautifully Natural Lanscaped in Excellant Winter Park Neighborhood Near W.P.Hospital. Ready to Build Large Home. less
Listing Provided Courtesy of REAL ESTATE PROFESSIONALS SE
Popularity
$890,000
$3,518/mo
Monthly Payment:
$3,518
Principal & Interest:
$3,297
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $178,000 down)
Winter Park, FL 32789
Windsong Orange County School District
4bed 4bath 3,349sq ft $266 / sq ft SFR
Lot Size10,825sq ft Built2013 On Site241days
**Best price in Windsong** A Perfect home for entertaining. Upon entrance to this well maintained "like new" home you will notice the floor plan offers a three-way split and is... more
**Best price in Windsong** A Perfect home for entertaining. Upon entrance to this well maintained "like new" home you will notice the floor plan offers a three-way split and is perfect for your guests privacy. Your Chef's kitchen opens to the family room and features a gas range, Wolf and SubZero appliances as well as double ovens. Enjoy your mornings with the sunrise in your breakfast nook. Your large Formal Dining room is located to the left of the kitchen and wet bar. Adjacent to your dining area is a private office space complete with french doors. It Can also be used as a media room or Den. You can retreat to your oversized master suite in the evenings and enjoy a soak in your spa tub. The Master suite also features a generously sized closet. Granite countertops, travertine tile and wood floors throughout. Custom shutters, crown molding and tray ceilings compliment this homes interior. Come see this "model like" home today, Call me for a private showing. less
Listing Provided Courtesy of EXIT REALTY CENTRAL
Popularity
$344,900
$1,277/mo
Monthly Payment:
$1,277
Principal & Interest:
$1,277
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $68,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 2,436sq ft $142 / sq ft SFR
Lot Size11,578sq ft Built1986 On Site242days
New Remodel! Great 3 bedroom and 2 bathroom home located on corner lot across from Lake Killarney. Easy access to I-4, Winter Park, and downtown Orlando. Beautiful wood floors... more
New Remodel! Great 3 bedroom and 2 bathroom home located on corner lot across from Lake Killarney. Easy access to I-4, Winter Park, and downtown Orlando. Beautiful wood floors with exposed brick in Living Room and Kitchen. Brick on the home is originally from a structure from Rollins College. Enjoy the bright open kitchen with new cabinets, granite counter tops, and new appliances. The home offers a screened courtyard which is great for gardening or relaxation. Home offers a bonus room with separate entrance. Master bedroom offers a large walk in closet and master bath has a spa tub with separate shower. Enjoy all of the wonderful upgrades to this home. less
Listing Provided Courtesy of LEERDAM PROPERTIES INC.
Popularity
$425,000
$2,045/mo
Monthly Payment:
$2,045
Principal & Interest:
$1,574
HOA Dues:
$471
(Based on a 30 year fixed loan at 3.75% with $85,000 down)
Winter Park, FL 32789
3bed 3bath 1,944sq ft $219 / sq ft CND
Lot SizeN/Asq ft Built2004 On Site250days
Rarely available, this condo in the Arbors on Aragon is charming and conveniently nestled near the heart of Olde Winter Park. This three bedroom and three bathroom property is... more
Rarely available, this condo in the Arbors on Aragon is charming and conveniently nestled near the heart of Olde Winter Park. This three bedroom and three bathroom property is filled with a generous amount of natural light and nicely appointed finishes. A few of these quality appointments include hardwood flooring, crown molding, volume ceilings, granite counter tops, pavered porches and a tile roof. Built in 2004, the floor plan is modern and functional. The kitchen, dining and family room spaces are sizeable and open to each other. The kitchen features granite counter tops, stainless appliances, a built-in desk, pantry closet and abundant cabinetry for storage. The pavered and nicely landscaped backyard is fully fenced and accessed from the family room area. The downstairs bedroom has an adjacent full bathroom. This room can easily be doubled as a den or home office. Completing the first floor is an interior utility room with hidden storage and an attached one car garage. Headed to the second level, you will find decorative iron railing accents. The second bedroom and ensuite bath face out over the front of the home with french doors leading to a private balcony with great views of Alfond Stadium. Across the landing is the expansive master suite, thoughtfully finished with wide plank flooring, walk-in closet with built-in organization system, and french doors leading to the serene screened balcony. Exquisite master bath includes double sinks, a garden tub, and separate shower. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,299,500
$4,814/mo
Monthly Payment:
$4,814
Principal & Interest:
$4,814
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,900 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,834sq ft $339 / sq ft SFR
Lot Size17,835sq ft Built1955 On Site251days
NEW PRICE and located in the desirable heart of the VIA's, this cottage style home in SICILIAN SHORES, is a meticulously renovated Winter Park beauty! Nestled quietly on an... more
NEW PRICE and located in the desirable heart of the VIA's, this cottage style home in SICILIAN SHORES, is a meticulously renovated Winter Park beauty! Nestled quietly on an approx 18,000 Sq ft. CORNER LOT within minutes of the RACQUET CLUB. You have to see this home to truly appreciate all it has to offer but just to name a "few" . . . CHERRY HARDWOOD floors, Elegant MANICURED LAWN, LAP POOL with HOT TUB, COBBLESTONE PAVERS, DESIGNER LIGHT FIXTURES, SUB ZERO and THERMADOR APPLIANCES, CAMERA SECURITY SYSTEM, MEDIA ROOM, DESIGNER WINDOW TREATMENTS, WALL TO WALL WINDOWS, HOME AUDIO SYSTEM, A TRUE MASTER SUITE which features a JET TUB in the master bath and STEAMER in the DUAL HEAD shower, CALIFORNIA CLOSETS, HIGH VOLUME and TRAY CEILINGS, SKYLIGHTS, HOME GENERATOR, and a 40YR ELK DIMENSIONAL SHINGLE ROOF. Elegance, privacy, and sophistication combined with quality finishes and touches makes this home a true gem! *Owner willing to convert media room as part of negotiation* less
Listing Provided Courtesy of ESTATES HOMES SALES & RENTALS
Popularity
$159,000
$589/mo
Monthly Payment:
$589
Principal & Interest:
$589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $31,800 down)
Winter Park, FL 32792
Goldenrod Orange County School District
4bed 2bath 1,347sq ft $118 / sq ft SFR
Lot Size11,133sq ft Built1959 On Site252days
Short sale. Listing price approved by lender.All home square footage and lot size, if exact square footage is concern, the property should be independently measured. Seller does... more
Short sale. Listing price approved by lender.All home square footage and lot size, if exact square footage is concern, the property should be independently measured. Seller does not provide condo/ hoa docs, this is the responsibility of the buyer. All information recorded in the mls is intended to be accurate but cannot be guaranteed, buyer advised to verify. Seller has retained an attorney to negotiate the short sale transaction. less
Listing Provided Courtesy of FLORIDA REALTY TEAM OF CENTRAL
Popularity
$879,900
$3,259/mo
Monthly Payment:
$3,259
Principal & Interest:
$3,259
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $175,980 down)
Winter Park, FL 32792
Orange County School District
6bed 4bath 5,449sq ft $161 / sq ft SFR
Lot Size20,128sq ft Built2000 On Site253days
Short sale. Bank approved price! Lender will respond to all offers within 20 days. Priced $300,000 below appraisal! Nestled in desirable winter park, come home to your own... more
Short sale. Bank approved price! Lender will respond to all offers within 20 days. Priced $300,000 below appraisal! Nestled in desirable winter park, come home to your own private oasis! Sprawling oak trees and a sweeping landscape welcome you to this 6 bed/4 bath 2-story custom home on a premium 1/2 acre lot. step inside and fall in love with the soaring cathedral ceilings and stunning floor-to-ceiling glass windows that flood the elegant living room with natural light. This spacious beauty also boasts 2 master suites (one on each floor) and a separate 2-bedroom first floor suite perfect for in-laws or an extended family! the first floor bedrooms open up to a private deck with a hot tub where you can relax in comfort under the stars. Or if you're feeling like entertaining, host a spectacular party in your expansive back yard! Back inside, enjoy the views of your garden or catch a cardinal or blue-jay flying by while making breakfast in your bright, open kitchen or while unwinding in the family room. Upstairs you'll find three bedrooms, including the second master suite all with private balconies! A den/library & large bonus room complete the second floor. oversized garage with double doors that open on both sides. Nearby shopping & restaurants abound, including the world-class shops and restaurants of park avenue! Plus, convenient to wp hospital, ymca, whole foods, phelps park & interlachen country club; along with a-rated schools. call today for a private showing! less
Listing Provided Courtesy of KELLER WILLIAMS HERITAGE RLTY
Popularity
$1,999,000
$7,406/mo
Monthly Payment:
$7,406
Principal & Interest:
$7,406
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $399,800 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 5,410sq ft $370 / sq ft SFR
Lot Size26,421sq ft Built1992 On Site255days
A contemporary one-of-a-kind work of art located on over half an acre in the heart of the Via’s. This one owner, custom built paradise is light, bright and incredibly... more
A contemporary one-of-a-kind work of art located on over half an acre in the heart of the Via’s. This one owner, custom built paradise is light, bright and incredibly open with soaring ceilings and hand crafted skylights that create the feeling of bringing the outside IN. Large, accommodating living spaces are perfect for entertaining, replete with dining room, living room, kitchen open to family room with fantastic bar area, all overlooking tropical outdoor oasis with covered and screened patios, beautiful pool, and backyard. This one story home is a split plan with spacious private master suite with extra sitting room and luxurious bath. 3 additional bedroom suites with full baths + extra office. Gourmet kitchen with island and breakfast nook. Additional features include extensive crown molding and built-ins, 3 car garage, 4 AC units - all 4 years new, new roof 2014, 2 wine coolers, whole house generator. “A” rated schools include Dommerich Elementary, Maitland Middle and Winter Park High. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$489,000
$1,811/mo
Monthly Payment:
$1,811
Principal & Interest:
$1,811
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $97,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,432sq ft $201 / sq ft SFR
Lot Size10,550sq ft Built1966 On Site257days
Best priced priced 4 bedroom 3 bath home in olde winter park . Reduced to sell !!!! Lot size 100 x 104 !!! Freshly painted , and the owner has just added a home warranty !!!!... more
Best priced priced 4 bedroom 3 bath home in olde winter park . Reduced to sell !!!! Lot size 100 x 104 !!! Freshly painted , and the owner has just added a home warranty !!!! Wonderful mid century corner lot home with hardwood floors throughout in winter park 32789 . New roof in 2014 & solid block construction with an indoor laundry room . Close to whole foods , winter park hospital , phelps park , winter park ymca , the crosby center , baldwin park ,windsong , the winter park racquet club , trinity preparatory school , interlachen country club , & park avenue . This wonderful home is zoned for the a+++ winter park school district . This home is a great investment for flippers . less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$1,695,000
$6,279/mo
Monthly Payment:
$6,279
Principal & Interest:
$6,279
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $339,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,879sq ft $347 / sq ft SFR
Lot Size18,293sq ft Built2000 On Site258days
Stunning Modern Mediterranean with oversized corner lot on beautiful brick street in sought after neighborhood convenient to ICC, YMCA & Phelps Park... Elegant style with... more
Stunning Modern Mediterranean with oversized corner lot on beautiful brick street in sought after neighborhood convenient to ICC, YMCA & Phelps Park... Elegant style with character and quality thru-out this custom designed residence... 5 BE with lavish Master retreat down along with additional bedroom/guest suite and 3 bedrooms & bonus/media room upstairs... Gourmet chef's island kitchen with commercial style stainless appliances, sleek sophisticated cabinetry, separate breakfast room & friends/family side entry... Great entertaining home with elegant formal dining & living rooms , walk-in wine cellar, wine refrigerators, and generous gathering room with full bar, fireplace, built-ins and more... Gorgeous hardwood & travertine flooring thru-out, custom carved olde world doors, high ceilings, beams, fireplace & more... Exquisite backyard, tropical pool & spa, mature wonderful premium landscaping... Pella windows & doors, 3 garages and motor-court with expansive grounds and park like setting... 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
Orange County School District
4bed 2bath 1,540sq ft $292 / sq ft SFR
Lot Size8,705sq ft Built1947 On Site261days
146' x 62' +/- lot - one of the only available corner lots on a brick street in winter park! Sold as-is. Per winter park zoning & planning, you can build on 43% of the lot size... more
146' x 62' +/- lot - one of the only available corner lots on a brick street in winter park! Sold as-is. Per winter park zoning & planning, you can build on 43% of the lot size putting this one at 3,741 sq. Ft. = 3,300 sq. Ft. Of living space if a 2 car garage was added. Ideally, a 2 story home would work on this lot to maximize the home space. Excellent location, close to mead gardens, leu gardens, blue jacket park, baldwin park shopping. Dining and outdoor space. Walk/bike to park avenue, rollins college, and the shops of corinne drive. less
Listing Provided Courtesy of RE/MAX 200 REALTY
Popularity
$1,489,000
$5,737/mo
Monthly Payment:
$5,737
Principal & Interest:
$5,516
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $297,800 down)
Winter Park, FL 32789
Orange County School District
4bed 7bath 5,000sq ft $298 / sq ft SFR
Lot Size11,048sq ft Built2008 On Site262days
Open Sun Feb 14, 1pm-4pm
Located in Winter Park’s premier Windsong community only a short distance from Park Ave. Extensive use of detailed ceilings, custom glazed moldings, solid hand distressed... more
Located in Winter Park’s premier Windsong community only a short distance from Park Ave. Extensive use of detailed ceilings, custom glazed moldings, solid hand distressed Hickory hardwood floors, Busby cabinets throughout and hand textured drywall finishes. Superlatives are not enough to describe the inspirational design characteristics and interior spaces, coupled with lush landscaping, pool/spa/fountain feature plus a summer kitchen all crafted to the highest standard. A stunning showcase of luxurious finishes & amenities! A truly magnificent Busby designed kitchen with Wolf and Subzero high end appliances, pot filler plus a fabulous Eat-In island & walk-in pantry. Wonderful 1st floor master retreat leaves little to be desired with its beamed vaulted ceiling, fireplace and large custom his/her closets, steam shower and bidet and jetted tub. Downstairs bedroom or study with private bath and custom built-ins would be wonderful as a guest retreat or home office space. Upstairs provided the perfect retreat for entertaining with 2 bedrooms 2 and a half baths plus a family gathering room with a fireplace and balcony, bonus/media room complete with home theater for movie nights & a wet bar. This home is in mint condition & extremely well maintained... Enjoy all the Windsong amenities including 2 community pools, a water park, playground, fishing pier, boardwalks, walking trails, chain of lakes access & more! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$999,900
$3,704/mo
Monthly Payment:
$3,704
Principal & Interest:
$3,704
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,980 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,050sq ft $328 / sq ft SFR
Lot Size8,415sq ft Built2015 On Site262days
***Click the virtual tour icon to watch the 3D rendering video - fly thru!!*** NEW CONSTRUCTION. Fantastic Transitional architecture by Way Cool Homes. Custom built by... more
***Click the virtual tour icon to watch the 3D rendering video - fly thru!!*** NEW CONSTRUCTION. Fantastic Transitional architecture by Way Cool Homes. Custom built by FG Schaub Homes with all the features you have come to expect from this exceptional builder. The wonderful ,open kitchen features custom cabinetry and solid surface counters. Energy features include radiant barrier insulation, Honeywell thermostats and tankless gas water heaters. The master is located downstairs and has a spacious walk in closet with custom shelving. The master bath features a lovely, freestanding tub and large shower with jets. 3 large, en suite bedrooms and a work space are upstairs. There is smart home technology that includes an I pad to control the 4 camera system, the thermostats and security system and can be expanded to include whole house audio which is already pre wired and ready to go. "A" rated Winter Park schools and walking distance to shopping, dining and the "Y" make this the perfect home. Come make an appointment to see this amazing home before it is gone! less
Listing Provided Courtesy of COLEDEV REAL ESTATE LLC
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
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size8,705sq ft BuiltN/A On Site262days
146' x 62' +/- lot - one of the only available corner lots on a brick street in winter park! Sold as-is. Per winter park zoning & planning, you can build on 43% of the lot size... more
146' x 62' +/- lot - one of the only available corner lots on a brick street in winter park! Sold as-is. Per winter park zoning & planning, you can build on 43% of the lot size putting this one at 3,741 sq. Ft. = 3,300 sq. Ft. Of living space if a 2 car garage was added. Ideally, a 2 story home would work on this lot to maximize the home space. Excellent location, close to mead gardens, leu gardens, blue jacket park, baldwin park shopping. Dining and outdoor space. Walk/bike to park avenue, rollins college, and the shops of corinne drive. less
Listing Provided Courtesy of RE/MAX 200 REALTY
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
Website provided and owned by Coldwell Banker Residential Real Estate.
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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 My 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: Saturday, February 13, 2016 at 7:51 PM. Properties in listings may have been sold or may no longer be available.