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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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$589,000
$2,390/mo
Monthly Payment:
$2,390
Principal & Interest:
$2,182
HOA Dues:
$208
(Based on a 30 year fixed loan at 3.75% with $117,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size23,512sq ft BuiltN/A On Site4days
Amazing chance to own a huge windsong lot - build your dream home. House and plans also available as a new home lisitng - see MLS
Amazing chance to own a huge windsong lot - build your dream home. House and plans also available as a new home lisitng - see MLS less
Listing Provided Courtesy of Aig Realty Services Llc
Popularity
Your search results are current and complete. Learn more
$547,000
$2,026/mo
Monthly Payment:
$2,026
Principal & Interest:
$2,026
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $109,400 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,982sq ft $183 / sq ft SFR
Lot Size12,063sq ft Built1974 On Site4days
Charm and sophistication radiate from this beautifully maintained Winter Park home located in much desired Quail Hollow. As you make your way on the circular driveway and pass... more
Charm and sophistication radiate from this beautifully maintained Winter Park home located in much desired Quail Hollow. As you make your way on the circular driveway and pass by the lush landscaping and two-car garage, you will find yourself gazing longingly at the custom solid wood front entrance doors. Upon entering, you will bask in the natural lighting illuminating the main space. You will be elated to find a spacious Florida room leading to the most private, lush oasis wrapped around a sparkling blue pool alongside meticulously laid Chicago brick pavers. Back inside you will experience an updated kitchen with granite countertops to fulfill all your needs in hosting and entertaining your guests. You will find the master retreat tucked away past the spacious secondary bedrooms, with wonderful views of your private oasis. This home exudes the Winter Park lifestyle and is waiting for your buyers to call it their new home. Please click on the movie reel links (2) to view additional photos & video & upgrades/features. less
Listing Provided Courtesy of Regal R.e. Professionals Llc
Popularity
$1,295,000
$4,797/mo
Monthly Payment:
$4,797
Principal & Interest:
$4,797
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,663sq ft $354 / sq ft SFR
Lot Size25,409sq ft Built1959 On Site4days
The value is in the land! At roughly 140 ft. wide x 180 ft. deep, this lot is the perfect site for the home of your dreams in the highly desirable Via neighborhood. City-owned... more
The value is in the land! At roughly 140 ft. wide x 180 ft. deep, this lot is the perfect site for the home of your dreams in the highly desirable Via neighborhood. City-owned land next door offers additional privacy, as well as a private walking path to the Winter Park Racquet Club. Conveniently located minutes from downtown Winter Park. Copy of Survey attached to listing. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$75,900
$526/mo
Monthly Payment:
$526
Principal & Interest:
$281
HOA Dues:
$245
(Based on a 30 year fixed loan at 3.75% with $15,180 down)
Winter Park, FL 32792
2bed 2bath 990sq ft $77 / sq ft CND
Lot Size1.4acre Built1984 On Site4days
Immaculate, move-in ready! 2 bed/1.5 bath, 2 story condo in Hidden Oaks community of Winter Park. This end unit on a corner lot will not disappoint. Living/dining room combo,... more
Immaculate, move-in ready! 2 bed/1.5 bath, 2 story condo in Hidden Oaks community of Winter Park. This end unit on a corner lot will not disappoint. Living/dining room combo, built-in cabinet in dining, Saltillo tile on first floor, indoor laundry, outside storage closet. Completely renovated bathrooms, NEW double pane energy efficient windows and french doors significantly lowers the energy bill! Upstairs bedrooms have oversized closets to maximize space. This unit has 2 assigned parking spaces at your front door. Community pool and playground. Close to UCF, Full Sail and Valencia and zoned for Winter Park schools. less
Listing Provided Courtesy of Alicia Spears Realty
Popularity
$825,000
$3,056/mo
Monthly Payment:
$3,056
Principal & Interest:
$3,056
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $165,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
4bed 4bath 2,849sq ft $290 / sq ft SFR
Lot Size14,466sq ft Built1923 On Site4days
Fabulous 1920's Dutch Colonial nestled in prime Olde Winter Park setting walking distance to Park Ave / Downtown Winter Park... This New England style home is elevated from... more
Fabulous 1920's Dutch Colonial nestled in prime Olde Winter Park setting walking distance to Park Ave / Downtown Winter Park... This New England style home is elevated from street level on beautiful oversized 1/3 acre corner lot... Current owner has restored home with historic style and added some modern updates/finishes... Bright-open floor plan with tremendous character & charm await you from the moment you step into the foyer... Features include original smooth plaster walls, high ceilings, generous living areas, exquisite hardwood floors, French doors, period lighting, extensive moldings & true craftsmanship, plantation shutters, oversized brick masonry fireplaces in main living room and original master bedroom... Main level includes kitchen, mud room, formal dining room, living room with fireplace, primary master bedroom, sun room & lovely screened porch overlooking serene fabulous northern style back yard with flagstone patio area for outdoor entertaining... Recent enhancements include a lot of "TLC", complete new paint in/out, refinished hardwood floors, updated baths, upgraded electrical, new plumbing, new ac systems, refurbished some windows, all new landscaping and more! Also, deeded access to park on Lk Virginaia with amazing sunset & Rollins College views w/ kayak/canoe storage This home has been well preserved and unfortunately the current owners have now been transferred out of state... must see to appreciate breathtaking Old Florida home that could easily be found in Nantucket as well! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$145,000
$537/mo
Monthly Payment:
$537
Principal & Interest:
$537
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,000 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 1,358sq ft $107 / sq ft SFR
Lot Size8,986sq ft Built1964 On Site4days
Charming 3 bedroom, 2 bath clean, well cared for home. Open floor plan featuring a large family room and living room ready to entertain your guests. Updated kitchen with a side... more
Charming 3 bedroom, 2 bath clean, well cared for home. Open floor plan featuring a large family room and living room ready to entertain your guests. Updated kitchen with a side door for easy access from the carport to bring in the groceries. Enjoy your morning coffee on the over-sized screened-in porch overlooking the large backyard with lush landscape. Property is in Orange County section of Eastbrook zoned for Winter Park schools. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$95,000
$651/mo
Monthly Payment:
$651
Principal & Interest:
$351
HOA Dues:
$300
(Based on a 30 year fixed loan at 3.75% with $19,000 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,365sq ft $70 / sq ft TWN
Lot Size6.7acre Built1974 On Site4days
This townhouse is truly move in ready!!! Perfect for first time buyers, snow birds, or parents looking for a home for their sons or daughters attending one of the colleges in... more
This townhouse is truly move in ready!!! Perfect for first time buyers, snow birds, or parents looking for a home for their sons or daughters attending one of the colleges in the area. The kitchen is all updated with new appliances, cabinets and more. The master bedroom has it's own balcony with a view overlooking the fenced and tiled private courtyard. It also has a large closet. There is a living room/dining room combo and the kitchen has a breakfast area. Just imagine sipping your morning coffee looking out at the screened porch. Speaking of the screened porch all the screen is new also! There is a large storage space outside not to mention all the storage inside. The A/C has been cleaned and serviced. The home is in an a-rated school district and close to all the major attractions. Come see this great townhome today!!!! less
Listing Provided Courtesy of Florida Oasis Realty Inc
Popularity
$1,399,000
$5,183/mo
Monthly Payment:
$5,183
Principal & Interest:
$5,183
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $279,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,436sq ft $315 / sq ft SFR
Lot Size11,862sq ft Built2015 On Site5days
New construction 2015 European style home built by Carmen Dominguez. Walking distance to Park Ave with a truly fantastic floor plan and elegant finishes. The dramatic two-story... more
New construction 2015 European style home built by Carmen Dominguez. Walking distance to Park Ave with a truly fantastic floor plan and elegant finishes. The dramatic two-story foyer leads to the open great room with gorgeous pool and covered lanai views. The living and dining areas are well defined with a bright and open flow, accented by a stylish wet bar with counter seating, built-ins and wine refrigerator. Gorgeous eat-in island kitchen with custom cabinets, 6 burner gas stove and double oven, high-end appliances and walk-in pantry. Office or 5th bedroom also downstairs along with a full pool bath, 8’x10’ flex room and huge laundry room. Master on main with hardwood floors and pool and lanai access. Spectacular master bath with glass tile accents, double vanities, soaking tub and glassed-in shower. Glamorous custom his & hers closets, with an island in the larger. Both levels feature 10’ ceilings, 8’ solid wood doors and wonderful natural light with energy efficient windows. The hardwood floors are continued through the upstairs loft and hallway. Three generous upstairs bedrooms each with well designed baths. This home is the epitome of excellent craftsmanship, bridging classic and cutting edge design—all within reach of downtown Park Avenue! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$100,000
$647/mo
Monthly Payment:
$647
Principal & Interest:
$370
HOA Dues:
$277
(Based on a 30 year fixed loan at 3.75% with $20,000 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,043sq ft $96 / sq ft CND
Lot Size5.0acre Built1986 On Site5days
2/2 single floor condo in winter park pines! Condos in this complex are rarely on the market for sale. This is a split bedroom plan, with a very large master and vaulted... more
2/2 single floor condo in winter park pines! Condos in this complex are rarely on the market for sale. This is a split bedroom plan, with a very large master and vaulted ceilings throughout, with comfortable laminate flooring throughout all the main rooms. Master has a nice walk-in closet, tiled shower, and sliding doors that open to the screened in porch. The guest bath offers a tub/shower combo. There is also small backyard, privacy fenced, with nice plants and paving stones. The kitchen opens to the living/dining room and also has sliding doors that open to your front patio. Condo comes with a one car garage, and has a storage room on the back patio. Plenty of storage space! Schools are great, and located near shopping and restaurants. The quota of rentals in this community has been met, so this condo needs to be owner occupied. Cute condo with terrific floor plan - just needs some cosmetic updating. Being sold as-is. less
Listing Provided Courtesy of Sutton & Sutton Realty, Inc.
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
2bed 1bath 1,132sq ft $331 / sq ft SFR
Lot Size10,510sq ft Built1951 On Site5days
Enjoy Hardwood floors and terracotta tile throughout. No carpet to hide dust and allergins! Master Bathroom has dual closets. Upgrades around every corner! HVAC, electrical and... more
Enjoy Hardwood floors and terracotta tile throughout. No carpet to hide dust and allergins! Master Bathroom has dual closets. Upgrades around every corner! HVAC, electrical and plumbing all redone! Attic insulation, garage door, windows and exterior doors have been upgraded throughout the entire home. Access to gas is available nearby, across the street! A remodeled kitchen boasts granite countertops, newer appliances and a porcelain farmhouse apron sink. Both French doors are fashioned with retractable screens which lead to a wooden decked patio complete with support footers and large, well landscaped playful rear yard. The home also has gutters and downspouts, a charming vintage bath with clawfoot tub, subway tiles, and pedestal sink. The lot is deceivingly large and could accommodate an addition or new construction! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$635,000
$2,485/mo
Monthly Payment:
$2,485
Principal & Interest:
$2,352
HOA Dues:
$133
(Based on a 30 year fixed loan at 3.75% with $127,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 3,595sq ft $177 / sq ft SFR
Lot Size14,943sq ft Built1993 On Site5days
Your very own private oasis in winter park. This elegant bear gully pointe custom pool home is open, friendly and inviting. It’s ideal for relaxing, entertaining and... more
Your very own private oasis in winter park. This elegant bear gully pointe custom pool home is open, friendly and inviting. It’s ideal for relaxing, entertaining and family fun. You’ll adore the beautifully appointed architectural details and extras throughout. The big, modern chef’s kitchen boasts breakfast area, island, stunning granite, abundant cherry cabinets, two pantries, plus an adjoining butler’s pantry. Formal living, dining and family rooms are all spacious and flow together beautifully. The downstairs master suite is extra large & private, with jetted tub & huge walk in closet. Also downstairs is office/bonus room and a 2nd bedroom (aka in-law suite with sitting area, separate entrance and adjoining full bathroom). Upstairs are two large bedrooms with jack & jill bath. Don’t miss the air conditioned bonus room #2 that can be accessed from the 3 car garage. Wood floors, crown molding, plantation shutters, columns, stone fireplace, soaring ceilings, summer kitchen and that fabulous portico are just some of the outstanding features. The french doors and transom windows provide plenty of natural light and gorgeous views of the pool, lanai and landscaped private yard. All bedrooms have walk in closest, all bathrooms are full bathrooms. Bear gully pointe is a gated, sought after community. Minutes to beltway, downtown, airport, ucf, siemens, lockheed, research park & trinity prep. Nearby top schools, fine restaurants, great shopping, & trails. Don’t miss this one! less
Listing Provided Courtesy of Re/max Optima
Popularity
$36,000
$133/mo
Monthly Payment:
$133
Principal & Interest:
$133
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $7,200 down)
Winter Park, FL 32789
N/Asq ft N/A / sq ft LND
Lot Size4,493sq ft BuiltN/A On Site5days
Can you believe this a buildable lot in Winter Park for this price. This lot has been cleared and it has been confirmed with the counter that it is a buildable. The property is... more
Can you believe this a buildable lot in Winter Park for this price. This lot has been cleared and it has been confirmed with the counter that it is a buildable. The property is convenient to I-4, shopping and downtown Winter Park. Bring your builder and your imagination. less
Listing Provided Courtesy of Real Living Good Neighbor Rlty
Popularity
$499,000
$2,682/mo
Monthly Payment:
$2,682
Principal & Interest:
$1,848
HOA Dues:
$834
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,567sq ft $318 / sq ft CND
Lot Size2.8acre Built1960 On Site5days
Welcome home to easy living in the heart of Winter Park. This FIRST FLOOR condo is ideally located with its own private gated patio, perfect for the gardener, and a sprawling... more
Welcome home to easy living in the heart of Winter Park. This FIRST FLOOR condo is ideally located with its own private gated patio, perfect for the gardener, and a sprawling back patio with lake views. The 2 bedroom/ 2 bath condo includes travertine tile, new double pane windows and large sliding glass doors. The open living & dining room combination overlooks the lush landscape and winding water features. Surround sound speakers are located in the living room, master suite and the Florida room. The kitchen, with granite counters, opens up to the dinette area located in the bright rotunda, or Florida room. You will never want to leave this fabulous Florida wrapped in 9 windows and 2 glass doors just bursting with natural light. It is perfect for entertaining while located off the large patio. The bathrooms have been updated with beautiful marble throughout. The large master suite includes a walk-in closet, linen closet, office area with lake views, and a full size washer and dryer. The relaxing pool is just steps away from the back door. Or enjoy the front community patio for stunning views of Lake Osceola. Boat slips may be available to rent, upon request. The 55+ Community has plenty of room for ALL AGE buyers..so do not fret…any age can live here! This is condo living at it’s best with only steps away from great restaurants and shopping galore on Park Ave. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$689,000
$2,552/mo
Monthly Payment:
$2,552
Principal & Interest:
$2,552
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $137,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,333sq ft $207 / sq ft SFR
Lot Size9,450sq ft Built1991 On Site5days
Nestled in the heart of Winter Park under majestic oak trees, you will find this privately gated and beautiful four bedroom, three and one-half bath home. More than 1,800 square... more
Nestled in the heart of Winter Park under majestic oak trees, you will find this privately gated and beautiful four bedroom, three and one-half bath home. More than 1,800 square feet of extensive outside decking, pavered patios and walkways take advantage of the outdoor beauty and privacy surrounding this home. The interior offers two master suites, a renovated and top-of-the-line gourmet kitchen, and spacious bedrooms. A great room housing the gracious family room with wood-burning fireplace, a charming sitting area, and dining room overlook the sunroom with French doors leading to the inviting deck and brick courtyard. The open kitchen features a Wolf 6-burner gas range, breakfast bar, built-in double ovens, silestone counters and a separate breakfast nook. Downstairs master with en suite bath has a large sunken Jacuzzi tub, dual vanity and walk-in closet; glass doors open to a private outdoor sitting area. For additional storage, this home also features a full, walk down basement with 7’ ceilings and sliding windows. Upstairs you will find a fantastic bonus room and a second outstanding master suite with views of Lake Virginia, as well as two generously sized bedrooms and one additional full bath. Roof and windows were replaced in 2014. Great Winter Park schools! This home is located in one of Winter Park's most desirable neighborhoods, with shopping, dining and entertainment on Park Avenue just a pleasant stroll away. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$1,375,000
$5,094/mo
Monthly Payment:
$5,094
Principal & Interest:
$5,094
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $275,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,511sq ft $250 / sq ft SFR
Lot Size22,599sq ft Built1970 On Site5days
Exceptional 5500 sq ft 5 bedrooms 5.5 baths custom home carefully renovated and re-crafted with entertainment in mind and provides comfort and elegance!! No expense spared!... more
Exceptional 5500 sq ft 5 bedrooms 5.5 baths custom home carefully renovated and re-crafted with entertainment in mind and provides comfort and elegance!! No expense spared! Situated on a 1/2 acre home-site with 195 ft of frontage on howell creek and views to bonnie burn park. Quality finishes include: wood, natural stone, & marble flooring; anderson low-e windows, full masonry fireplace, 2 stairways, extensive use of crown moldings and mill work throughout the home! First floor with open formals & family room with views to the chef`s kitchen showcased by granite counter tops, large working island, ss appliances, double ovens & lots of storage! Walk-in pantry. The home also features 2 separate laundry rooms located on 1st & 2nd floor. Dinette with wet bar and wine cooler with open views looking out onto your back yard and creek. 3 bedrooms & 3 baths on 1st floor with 2 patios, great for your evening wine & cheese. The 2 car garage has a separate work shop & storage area along with a porch that can be accessed from the kitchen too. The 3,000 sq ft upstairs is highlighted by the 1,000 sq ft master suite with 16 ft high ceiling, transom windows, french doors opening to a private covered balcony. In the master you will find a california closet with sitting area, huge walk-in shower with body spray system, jetted tub, separate vanities and laundry room. The 2nd floor also includes another large bedroom with adjoining bath and a bonus room for home office or gym. Click to see the walk-thru video tour. less
Listing Provided Courtesy of Bhhs Results Realty
Popularity
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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: Friday, July 3, 2015 at 8:21 AM