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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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$4,875,000
$18,061/mo
Monthly Payment:
$18,061
Principal & Interest:
$18,061
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $975,000 down)
Winter Park, FL 32789
Orange County School District
6bed 9bath 10,493sq ft $465 / sq ft SFR
Lot Size1.1acre Built2008 On Site58days
Incredible 2008 custom-built lakefront home nestled on over one acre along the shores of Lake Maitland. This home has it ALL! The living and entertaining areas are spacious and... more
Incredible 2008 custom-built lakefront home nestled on over one acre along the shores of Lake Maitland. This home has it ALL! The living and entertaining areas are spacious and elegant, with sweeping views of the lake from almost every room. High end finishes include hand scraped wood floors, crown molding, French doors, surround sound, central vacuum, custom built-ins, beamed ceilings and other detailed millwork throughout. The downstairs has formal living room, dining room, media room, exercise room, game room with impressive granite bar, and family room that opens to kitchen. The kitchen is a cook’s dream with stainless appliances, Dacor 6 burner gas cooktop with double ovens & convection, large island, Butler’s pantry with coffee bar & wine refrigerator, and beautiful eat-in area overlooking the water. Adjacent downstairs guest suite, laundry & mud room, and computer work station. There are 3 more bedroom suites upstairs plus the master suite which resembles a 5 star hotel with sitting room, double walk-in closets, balconies with lake views, and luxurious bathroom. Interior bonus/guest studio as well as detached guest apartment. 5 car garage. Gazebo with pool & spa, boathouse with lift and Jet Ski space. “A” rated schools!!! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
Your search results are current and complete. Learn more
$449,000
$1,663/mo
Monthly Payment:
$1,663
Principal & Interest:
$1,663
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $89,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,643sq ft $123 / sq ft SFR
Lot Size8,594sq ft Built1964 On Site58days
Fabulous four bedroom (consisting of two Master Suites), three and a half bath home. The upstairs bonus room, which includes a wood burning fireplace, and the downstairs office... more
Fabulous four bedroom (consisting of two Master Suites), three and a half bath home. The upstairs bonus room, which includes a wood burning fireplace, and the downstairs office all add to this unique property. Wrought Iron Juliette balconies upstairs. Completely renovated with rich wood and French Doors throughout and also featuring granite countertops. The entrance opens to a grand foyer with sweeping staircase, beautiful chandelier and a large living room which leads to an open plan kitchen with an additional fireplace. All new stainless steel appliances, vaulted/high ceilings and rounded corners. Tons of storage and closet space. Upstairs master bath has separate pedestal sinks, jetted tub and large walk-in shower with rain showerhead. You’ll feel like you are at the spa. Third and fourth bedrooms have a Jack and Jill bathroom. Wonderful location right in the heart of Winter Park; very close to Park Avenue and Winter Park Village—great shopping and dining. Don’t miss this must-see property. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$2,250,000
$8,336/mo
Monthly Payment:
$8,336
Principal & Interest:
$8,336
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $450,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size37,500sq ft BuiltN/A On Site58days
150 x 250 vacant lot, 37,500 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf with a net of 34,000 sf of net... more
150 x 250 vacant lot, 37,500 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf with a net of 34,000 sf of net saleable air conditioned space. Each unit has a 2 car attached garage and access to outdoor parking for 7+ extra parking spaces. Four 2 story units and eleven 3 story units. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$269,000
$996/mo
Monthly Payment:
$996
Principal & Interest:
$996
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,800 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 800sq ft $336 / sq ft SFR
Lot Size6,242sq ft Built1958 On Site59days
Classic Winter Park 2/1 Cottage on a nice brick street!! Perfect starter home in Prime Neighborhood!! House was redone in 2001 with New Windows, New plumbing, New Air... more
Classic Winter Park 2/1 Cottage on a nice brick street!! Perfect starter home in Prime Neighborhood!! House was redone in 2001 with New Windows, New plumbing, New Air Conditioning, New Electrical panels and wiring, Crown molding and wainscoting, New kitchen, New bathroom fixtures with Claw foot bathtub, High efficiency Heat Pump Air Conditioning, New 6 panel interior doors Brick street Large oaks Refinished Hardwood floors Front porch Large shed in backyard Fenced yard Separate utility room off carport. Close to Rollins college and YMCA. less
Listing Provided Courtesy of Jack Keller Inc
Popularity
$249,500
$1,429/mo
Monthly Payment:
$1,429
Principal & Interest:
$924
HOA Dues:
$505
(Based on a 30 year fixed loan at 3.75% with $49,900 down)
Winter Park, FL 32789
Orange County School District
1bed 2bath 850sq ft $294 / sq ft CND
Lot Size1.6acre Built1969 On Site59days
Direct lakefront unit with breathtaking views. Spacious one bedroom, one and a half bath unit. Updated kitchen. Corian countertops. Oversized covered patio. Enjoy lakefront... more
Direct lakefront unit with breathtaking views. Spacious one bedroom, one and a half bath unit. Updated kitchen. Corian countertops. Oversized covered patio. Enjoy lakefront condo amenities, including club house, fitness room, sauna, pool, and spa. Guest suite. Rent-able boat slips. Direct lakefront units are truly rare! Call today for your private showing. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$54,000
$272/mo
Monthly Payment:
$272
Principal & Interest:
$200
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.75% with $10,800 down)
Winter Park, FL 32792
Seminole County School District
2bed 1bath 912sq ft $59 / sq ft SFR
Lot Size2,823sq ft Built1978 On Site59days
Best Kept Secret - Winter Park - Seminole County **Location Near Bus Line, Full Sail, UCF, Rollins**Community Pool**Tennis Court**Gated on South End to Discourage any Cut... more
Best Kept Secret - Winter Park - Seminole County **Location Near Bus Line, Full Sail, UCF, Rollins**Community Pool**Tennis Court**Gated on South End to Discourage any Cut Through**Owner Occupied Community**Very Active HOA** less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$375,000
$1,389/mo
Monthly Payment:
$1,389
Principal & Interest:
$1,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,247sq ft $167 / sq ft SFR
Lot Size12,738sq ft Built1966 On Site60days
Fantastic Winter Park Home! Tis the Season to come out and take a look at this beautiful home. This 4 bedroom 2.5 bath, pool home backs up to a tranquil conservation area and... more
Fantastic Winter Park Home! Tis the Season to come out and take a look at this beautiful home. This 4 bedroom 2.5 bath, pool home backs up to a tranquil conservation area and quiet stream. Too much to list in the remarks section. We know the demand will be great. So get up off the couch and take a look inside while you still can! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$279,900
$1,037/mo
Monthly Payment:
$1,037
Principal & Interest:
$1,037
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $55,980 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 2,121sq ft $132 / sq ft SFR
Lot Size9,294sq ft Built1955 On Site61days
Completely refinished wood floors, stainless steel appliance, new doors, baseboards , mirrors, light fixtures, pool covered, NO WORK NEEDED, NO SHORT SALE, NO BANK OWNED quick... more
Completely refinished wood floors, stainless steel appliance, new doors, baseboards , mirrors, light fixtures, pool covered, NO WORK NEEDED, NO SHORT SALE, NO BANK OWNED quick response. SELLER AND LISTING AGENT HAVE NO KNOLEDGE OF PROPERTY HISTORY. less
Listing Provided Courtesy of Florida Dreams Realty Grp Inc
Popularity
$695,000
$2,574/mo
Monthly Payment:
$2,574
Principal & Interest:
$2,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,816sq ft $247 / sq ft SFR
Lot Size6,050sq ft Built2015 On Site65days
A great opportunity to own your own brand new contemporary home designed and built by renowned architect and builder, Phil Kean. This WayCool Homes by Phil Kean design/build... more
A great opportunity to own your own brand new contemporary home designed and built by renowned architect and builder, Phil Kean. This WayCool Homes by Phil Kean design/build offers 2800+ SF of living space with a first floor master suite with a spacious walk-in closet, an open great room and a large open kitchen with a walk-in pantry and island with breakfast bar. The second floor has two ensuite bedrooms and a 15 x 11 loft area that can be used as a family room, study room or media room. Located on a charming brick street and a quick bike to Park Avenue, Rollins College and Winter Park Village. Purchase price subject to increase based on buyer's selections of finishes. Buyer is not limited to plan/renderings shown. less
Listing Provided Courtesy of Waycool Real Estate
Popularity
$210,000
$780/mo
Monthly Payment:
$780
Principal & Interest:
$778
HOA Dues:
$2
(Based on a 30 year fixed loan at 3.75% with $42,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 1,790sq ft $117 / sq ft SFR
Lot Size10,330sq ft Built1974 On Site65days
This 4/2 pool home is waiting for you! Large porch! Completely renovated with upgrades! Brand new kitchen and bathrooms with granite counter tops, new stainless steel... more
This 4/2 pool home is waiting for you! Large porch! Completely renovated with upgrades! Brand new kitchen and bathrooms with granite counter tops, new stainless steel appliances, ceramic tile flooring and laminate in the bedrooms, new sliding glass doors, light fixtures. This home is located in a cul-de-sac and is nearly 1/4 acre with a utility shed and fruit trees. Plenty of space for a large family to enjoy. Located in great school district! Must see this home! Desirable community !!! Not going to last on the market. less
Listing Provided Courtesy of Weichert Realtors Hallmark Pr
Popularity
$3,500,000
$12,967/mo
Monthly Payment:
$12,967
Principal & Interest:
$12,967
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $700,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 5,684sq ft $616 / sq ft SFR
Lot Size2.7acre Built1977 On Site66days
Lakefront living at it's finest in a spectacular downtown winter park location! Chain of lakes executive estate with amazing guest quarters nestled in the heart of olde... more
Lakefront living at it's finest in a spectacular downtown winter park location! Chain of lakes executive estate with amazing guest quarters nestled in the heart of olde winter park! Sprawling property offers panoramic views from 130 waterfront feet on picturesque lake maitland! This elegant home (totally renovated in 2001) boasts an outstanding master suite with his & her bathrooms & walk in closets; soaring ceilings in foyer & formal rooms; a smartly appointed gourmet kitchen with stunning cabinets & granite and a cozy breakfast nook; family room with exquisite millwork & built-ins plus a gas fireplace! The 26 x 17 downstairs bonus room perfect for your home office, game room or in-law suite plus an incredible guest home above the 3 car detached garage includes vaulted ceilings, large bedroom/full bath & fully equipped kitchen & laundry room. Stunning back yard oasis includes a fabulous patio for entertaining, perfectly manicured landscaping & stone enhanced waterfront with boat dock. Walk to park avenue from this serene cul-de-sac location! Welcome home! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,295,000
$6,427/mo
Monthly Payment:
$6,427
Principal & Interest:
$4,797
HOA Dues:
$1,630
(Based on a 30 year fixed loan at 3.75% with $259,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,272sq ft $396 / sq ft CND
Lot SizeN/Asq ft Built1990 On Site69days
Premier Winter Park condominium located in the heart of downtown Winter Park. This elegant & private Mediterranean style building includes only 8 units centered around a... more
Premier Winter Park condominium located in the heart of downtown Winter Park. This elegant & private Mediterranean style building includes only 8 units centered around a beautiful courtyard. This spacious single story 3 bedroom, 4 bath unit plus possible 4th bedroom or wonderful den features gorgeous hardwood floors throughout, formal living room w/ fireplace & French doors leading to 2 balconies, oversized formal dining room with decorative corner built-ins, master bedroom suite w/ fireplace, bath with dual sinks, tub & separate shower, large storage area & workshop area located in gated entry garage. Luxurious community pool & underground private parking. Walking distance to Park Avenue! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,145,000
$4,242/mo
Monthly Payment:
$4,242
Principal & Interest:
$4,242
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $229,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,709sq ft $309 / sq ft SFR
Lot Size9,749sq ft Built2007 On Site70days
Open Sun Feb 1, 1pm-4pm
Gorgeous custom-built five bedroom Mediterranean pool home located in the heart of Winter Park! This home, built in 2007, has a wonderful floor plan and top notch finishes and... more
Gorgeous custom-built five bedroom Mediterranean pool home located in the heart of Winter Park! This home, built in 2007, has a wonderful floor plan and top notch finishes and details throughout. The spacious gourmet kitchen has a large granite cooking island with a breakfast bar, a separate breakfast nook with pool views and a great butler's pantry which connects to the beautiful formal dining room. The kitchen is open to the family/great room with a gas fireplace and two sets of French doors that lead out to the pool and covered lanai with a built-in chef's grill. The ultra-private master suite also has French doors to the backyard/pool and a luxurious master bath with large shower and extra-deep soaking tub. A guest suite is also located on the first floor - great for company, a child/baby's room or an in-law suite. A stately office/den with built-ins completes the first floor. The second floor showcases three spacious bedrooms- two bedrooms share a Jack & Jill bath, and the third bedroom has a great kid's den/playroom attached. A loft/bonus room allows for a second family room. Enjoy the pool all year! Cool off in the summer with the poolside misting fans, or enjoy the heated pool during the winter months. Great location on a sought-after street near Windsong. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$149,000
$552/mo
Monthly Payment:
$552
Principal & Interest:
$552
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,800 down)
Winter Park, FL 32792
Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size1.8acre BuiltN/A On Site70days
Great opportunity!!! Lake front with 2.31 acres with lots of potential. Call today before it is to late.
Great opportunity!!! Lake front with 2.31 acres with lots of potential. Call today before it is to late. less
Listing Provided Courtesy of Assist 2 Sell All Sellers & Bu
Popularity
$117,900
$707/mo
Monthly Payment:
$707
Principal & Interest:
$436
HOA Dues:
$271
(Based on a 30 year fixed loan at 3.75% with $23,580 down)
Winter Park, FL 32789
Garden Acres Orange County School District
2bed 2bath 893sq ft $132 / sq ft CND
Lot Size13,119sq ft Built1967 On Site70days
Quaint and cozy 2 bedroom/2 bathroom condo in desirable Mead Garden. This condo features a living/dining room combo with an open kitchen. Dining area boasts cabinets providing... more
Quaint and cozy 2 bedroom/2 bathroom condo in desirable Mead Garden. This condo features a living/dining room combo with an open kitchen. Dining area boasts cabinets providing perfect storage space for dishes and kitchen items. Condo is complete with a screened- in patio, with window shades, overlooking the pool; providing the perfect retreat to relax. This community is in the perfect location and is well established. Condo would make an ideal home or fantastic investment property. Walking distance to restaurants and Park Avenue; beautiful Mead Gardens is just next door. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
7 8 9 10 11 12 13 14 15 ... 20
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: Wednesday, January 28, 2015 at 6:05 AM