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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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$1,135,000
$4,205/mo
Monthly Payment:
$4,205
Principal & Interest:
$4,205
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $227,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 4,249sq ft $267 / sq ft SFR
Lot Size12,543sq ft Built2008 On Site166days
An elegant classic home in Olde Winter Park! Located on a quiet street between Lake Osceola and N. Phelps Ave., this 5 bedroom, 4/2 bath pool home boasts high-end finishes and... more
An elegant classic home in Olde Winter Park! Located on a quiet street between Lake Osceola and N. Phelps Ave., this 5 bedroom, 4/2 bath pool home boasts high-end finishes and fixtures throughout. Beautiful wood floors, crown molding and upscale lighting fixtures complement this well-appointed home. There is a spectacular gourmet kitchen with a large granite island and high-end KitchenAid appliances, including an eight burner gas stove with pot filler, 2 ovens, and a wine refrigerator. Open to the kitchen is a large family room with surround sound, a fireplace and French doors opening to the covered lanai and pool area. There is a screen-enclosed, heated salt water pool and spa, outdoor shower, half bath and a fabulous summer kitchen, perfect for entertaining or just relaxing. The large master suite is downstairs and has a beautiful master bath with travertine floors, granite counters and a spacious walk-in closet with custom dark wood built-ins. In addition to the 5 bedrooms there is a home office on the first level with rich wood cabinetry and ceiling detail. Upstairs are the 4 additional bedrooms which are all spacious with plenty of storage in the roomy closets. The large bonus area upstairs can be used as an additional study, game room or sitting area. The home is very convenient to excellent schools, parks, WPH as well as upscale dining and boutiques on Park Ave. in downtown Winter Park! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
We show you every available listing. Here's how
$299,000
$1,107/mo
Monthly Payment:
$1,107
Principal & Interest:
$1,107
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,534sq ft $195 / sq ft SFR
Lot Size10,361sq ft Built1964 On Site169days
Wonderful, affordable winter park !!! This fabulous 3 bedroom 2 bath home has many upscale features such as travertine tile, granite counters, stainless steel appliances and 42"... more
Wonderful, affordable winter park !!! This fabulous 3 bedroom 2 bath home has many upscale features such as travertine tile, granite counters, stainless steel appliances and 42" cabinets in the gourmet kitchen. It also boasts of crown molding throughout. This home has an awesome backyard which includes a spectacular pool designed by hgtv. In addition, the property has a convenience gate to the cady way trail. Functional open floor plan with an extra large utility room. Located on a no outlet street. All of this and much, much more!!! Welcome home!!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$749,000
$2,774/mo
Monthly Payment:
$2,774
Principal & Interest:
$2,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,373sq ft $316 / sq ft SFR
Lot Size17,411sq ft Built1925 On Site169days
Rose Cottage" established in 1922 is a Winter Park landmark with timeless beauty and charm. Each owner has carefully renovated this bungalow over the years. High ceilings,... more
Rose Cottage" established in 1922 is a Winter Park landmark with timeless beauty and charm. Each owner has carefully renovated this bungalow over the years. High ceilings, heirloom architectural appointments, heart of pine floors, front, side and back porches. Recent additions or updates include a salt water heated pool and spa, screen on back porch, complete rebuild of the garage with the addition of a pool cabana, both driveways bricked, updated electrical including panels, laundry room update with equipment, new front and back porch decking and new fence. Other features include wood burning fireplace, large gourmet kitchen with gas and inviting sunroom all situated on three lots. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$599,000
$2,427/mo
Monthly Payment:
$2,427
Principal & Interest:
$2,219
HOA Dues:
$208
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Windsong Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size23,512sq ft BuiltN/A On Site170days
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 Coldwell Banker Residential Re
Popularity N/A
$2,295,000
$8,710/mo
Monthly Payment:
$8,710
Principal & Interest:
$8,502
HOA Dues:
$208
(Based on a 30 year fixed loan at 3.75% with $459,000 down)
Winter Park, FL 32789
Windsong Orange County School District
5bed 5bath 5,500sq ft $417 / sq ft SFR
Lot Size23,512sq ft Built2014 On Site170days
Stunning new one story 5,500 sf house on HUGE private 23,835 sf lot. Open and modern plan by Nasrallah Architectural Group and joint venture build by prestigious IBK... more
Stunning new one story 5,500 sf house on HUGE private 23,835 sf lot. Open and modern plan by Nasrallah Architectural Group and joint venture build by prestigious IBK Construction and Z Properties. Huge living spaces open to gracious outdoor living area and pool with pool cabana and outdoor kitchen. Spacious suites, split plan, no detail will be overlooked - four car garage. Do not miss this opportunity. Please call lisitng agent to schedule appointment to discuss time lines and budget. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$379,000
$1,404/mo
Monthly Payment:
$1,404
Principal & Interest:
$1,404
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size12,059sq ft BuiltN/A On Site170days
Opportunity knocks! With inventory at an all-time low you do not want to miss your chance to develop this great lot! Whether you are an investor, builder or plan to occupy -... more
Opportunity knocks! With inventory at an all-time low you do not want to miss your chance to develop this great lot! Whether you are an investor, builder or plan to occupy - build your dream home on this oversized 70x170 lot in winter park! Excellent proximity to everything - walk to the ymca ride your bike to park avenue to enjoy shopping, dining and entertainment or just a short drive to whole foods and so much more! Great schools! Close to i-4, 417 and 408. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$194,500
$720/mo
Monthly Payment:
$720
Principal & Interest:
$720
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $38,900 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,226sq ft $159 / sq ft SFR
Lot Size9,818sq ft Built1964 On Site170days
Charming Ranch home in "A" Rated school district (Dommerich Elementary, Maitland Middle, and Winter Park High). Exterior features brick and cypress siding, and landscaping... more
Charming Ranch home in "A" Rated school district (Dommerich Elementary, Maitland Middle, and Winter Park High). Exterior features brick and cypress siding, and landscaping includes numerous low-maintenance Florida native plants. Interior features 3 bedroom/ 2 bath, split floor plan, beautiful hardwood flooring throughout. Galley Kitchen with stainless steel appliances, connects to oversized laundry/ mud room. Master bedroom has a walk-in closet, bathroom with walk-in shower, and connected bonus room. Would be great for office, sitting area, or nursery. French doors from living/ dining room open to large outside area. As you step outdoors, a custom-made cedar pergola forms a shaded walkway to a large back yard surrounded by tall wooden fence for privacy. Yard is a gardeners dream with lemon and orange trees, numerous native flowers and trees, and plenty of room to grow. Detached workshop with electricity, lots of storage, and attached garden/bicycle shed in backyard. Truly a rare find, ideally located just off of Howell Branch Rd, just minutes from downtown Winter Park and Maitland. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,169,900
$4,334/mo
Monthly Payment:
$4,334
Principal & Interest:
$4,334
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $233,980 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,860sq ft $303 / sq ft SFR
Lot Size10,295sq ft Built2015 On Site171days
Elegant, Classic Italianate home on a lovely, tree lined street. This fantastic new home has 4 large bedrooms, all en suite, with a generous master down. Formal dining room,... more
Elegant, Classic Italianate home on a lovely, tree lined street. This fantastic new home has 4 large bedrooms, all en suite, with a generous master down. Formal dining room, study/ flex space and a gorgeous sun room make this plan work for the whole family. The kitchen features a 48" dual fuel range, a 48" built in refrigerator and a large dining island with prep sink. Hand scraped wood floors in all the main living areas, the master bedroom and the sun room as well as an all wood staircase. The homes energy features include LED lighting, radiant barrier insulation, thermal PGT windows and two tankless hot water heaters. There is an over sized, detached 2 car garage with plenty of storage. Call today about this wonderful new home and select your own finishes! less
Listing Provided Courtesy of Arlington Realty Inc
Popularity N/A
$5,200,000
$19,265/mo
Monthly Payment:
$19,265
Principal & Interest:
$19,265
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $1,040,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,850sq ft $759 / sq ft SFR
Lot Size42,678sq ft Built1999 On Site171days
Enter the private gate to find this sophisticated contemporary home along the shores of Lake Maitland. Outstanding features adorn this 2006 totally remodeled home. The front... more
Enter the private gate to find this sophisticated contemporary home along the shores of Lake Maitland. Outstanding features adorn this 2006 totally remodeled home. The front door opens to this beautiful open floor plan drawing your attention past the Dining Room to a most beautiful view of Lake Maitland. Foyer leads to an attractive Office with fireplace and built in shelves and an open Living Room, currently enjoyed as a Music Room, with piano and seating. Large Family Room with another gas fireplace and a wall of windows overlooks the Pool. Kitchen features double refrigerators, gas cook top, wine refrigeration room, center island and a breakfast area with built in desk. Off the Kitchen is a Guest Suite with full bath. Toward the back of the home is a Gathering Room with a wet bar and more views of the lake. The Master is located downstairs with a large Master Bath and closets. Electric shades can be open or shut with the push of a button. Upstairs hosts three en suite Bedrooms, one currently used as a Media Room. An added bonus is located between two bedrooms and currently used as an Art Studio, also perfect for a writer or convert to a playroom, with a scenic view of the lake. The outside area has a wrap around terrace with a Summer Kitchen off the Family Room and a Gathering Area off the Master with another gas fireplace. Dock includes a covered Boat House with hoist. Please view the virtual tour for more details. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$380,000
$1,407/mo
Monthly Payment:
$1,407
Principal & Interest:
$1,407
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $76,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,321sq ft $164 / sq ft TWN
Lot Size3,524sq ft Built1998 On Site172days
A must see inside!! This four bedroom three bath fee simple townhome will surprise you!! A spacious home offering two master suites, one bedroom & full bath downstairs, hardwood... more
A must see inside!! This four bedroom three bath fee simple townhome will surprise you!! A spacious home offering two master suites, one bedroom & full bath downstairs, hardwood floors, vaulted ceilings and a cozy wood burning, family room fireplace! Unit features a quaint, fenced back yard, inside utility room & one car garage. Steps from rollins college and winter park's farmers market & park avenue. Also available for rent $2500 per month! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$550,000
$2,037/mo
Monthly Payment:
$2,037
Principal & Interest:
$2,037
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $110,000 down)
Winter Park, FL 32792
N/Asq ft N/A / sq ft LND
Lot Size25,768sq ft BuiltN/A On Site172days
Prime vacant land on a corner lot at the intersection of Bates Road and Goldenrod with traffic light to drive vehicles into property! Billboards provide income from CBS of... more
Prime vacant land on a corner lot at the intersection of Bates Road and Goldenrod with traffic light to drive vehicles into property! Billboards provide income from CBS of $4,800/year + bonus (was $6,000 in 2013). Land includes private road connecting Goldenrod and Bates road. High traffic volume with 29,000 vehicles per day on Goldenrod. Land specs: 26,147 square feet or .60 acres, 152 foot frontage on Goldenrod, 161 feet deep, Zoned C-1 vacant commercial (Orange County 1000). Can be sold with 2 additional parcels (PID #112230000000009 and PID#112230000000043)all three totaling 60,706 square feet (1.39 acres) with 2 commercial buildings (one vacant, one tenant occupied). Close to UCF and 417 and minutes from Colonial Drive, University Blvd and the 408. less
Listing Provided Courtesy of Re/max Exclusive Collection
Popularity N/A
$1,225,000
$4,538/mo
Monthly Payment:
$4,538
Principal & Interest:
$4,538
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $245,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,020sq ft $305 / sq ft SFR
Lot Size9,747sq ft Built2002 On Site173days
Elegant home on a quiet brick street in the heart of Winter Park. Classic Mizner-style, designed by architect Gary Hancock. It has 4,020 square feet and was custom built in... more
Elegant home on a quiet brick street in the heart of Winter Park. Classic Mizner-style, designed by architect Gary Hancock. It has 4,020 square feet and was custom built in 2002. 4 bedrooms, 4.5 bathrooms, office/library, and a room for a home theater. Gracious entryway and foyer. Brazilian cherry floors and beautiful Pella windows and french doors. Both gas fireplaces have unique mantels and surrounds. The large open formal living and dining room, with its high ceiling and Mexican tile floor, is perfect for entertaining. The gourmet kitchen is for a serious chef, with its custom cabinetry, granite counter tops, food preparation island, Sub-Zero refrigerator, Bosch dishwasher and Thermador natural gas stove with 2 ovens. Separate suite for guests, a parent or older child. Decorator window finishes throughout. There are original tile wall mosaics by artist Ralph Young on the front porch and balcony, and the handcrafted gas lights outside add a touch of old world charm. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$1,099,900
$4,075/mo
Monthly Payment:
$4,075
Principal & Interest:
$4,075
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $219,980 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,658sq ft $301 / sq ft SFR
Lot Size12,300sq ft Built2015 On Site173days
Stunning contemporary designed by Way Cool Homes and built by Arlington. The large ,open great room and kitchen look out onto the beautiful lanai and sparkling pool. Retractable... more
Stunning contemporary designed by Way Cool Homes and built by Arlington. The large ,open great room and kitchen look out onto the beautiful lanai and sparkling pool. Retractable screens and a summer kitchen make your outdoor oasis complete.Custom wood cabinetry, extensive tile and wood, solid surface counters and stainless steel appliances complete the kitchen. A large open balcony off the loft area upstairs is a entertaining delight. This home is in pre construction and the finishes can still be customize to suit your needs. Call today for more information. less
Listing Provided Courtesy of Arlington Realty Inc
Popularity
$595,000
$2,204/mo
Monthly Payment:
$2,204
Principal & Interest:
$2,204
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,335sq ft $178 / sq ft SFR
Lot Size13,752sq ft Built1955 On Site173days
New price! Great 4 bedroom/3 bath, 3300+ sq. Ft. Pool home with tons of space, on a large lot, in a fantastic location! Renovated in 2003, upstairs added with 2 bedrooms... more
New price! Great 4 bedroom/3 bath, 3300+ sq. Ft. Pool home with tons of space, on a large lot, in a fantastic location! Renovated in 2003, upstairs added with 2 bedrooms features large jack 'n jill bath. Two master suites downstairs. Expansive great room with vaulted ceilings, wood burning fireplace that is surrounded by built-in shelves & cabinets. Large florida room with built-in bar looks out on to screened pool. Brand new screen enclosure surrounds the large pool/patio which has mature, lush landscaping providing lots of privacy. Semi-attached workshop is perfect for the handyman in the family or great to store sports equipment, holiday décor, etc...Terrific family & entertaining home! Seller offering a $5000 allowance for paint/renovations with an acceptable offer - call for your showing today! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$969,900
$3,693/mo
Monthly Payment:
$3,693
Principal & Interest:
$3,593
HOA Dues:
$100
(Based on a 30 year fixed loan at 3.75% with $193,980 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,462sq ft $280 / sq ft SFR
Lot Size10,905sq ft Built2004 On Site176days
Open Sun Nov 2, 1pm-4pm
Stunning four bedroom (plus an office) home with more than 3,400 square feet of exceptional living space in Pennsylvania Place. Gorgeous real hardwood floors throughout. High... more
Stunning four bedroom (plus an office) home with more than 3,400 square feet of exceptional living space in Pennsylvania Place. Gorgeous real hardwood floors throughout. High ceilings and crown moldings. Formal living room with fireplace and formal dining room-both have generous sunlight. Large office on the first floor. Gourmet kitchen with beautiful wood cabinets, granite countertops, stainless steel appliances, large walk in pantry and gas cook top. Eat in area with lots of sunny windows. The downstairs master suite is spectacular with lovely green space views, his and her walk in closets, large master bath with separate shower and tub. The upstairs has three bedroom suites, two full baths, large storage room and a bonus area with an outdoor covered balcony. Pennsylvania Place is wonderful neighborhood with a quiet park, sidewalks and rear entry garages. Walk to Park Avenue, the Winter Park Golf Course, and the Winter Park Village. 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
1.941.487.1400
Local service is provided by our preferred broker, Coldwell Banker Residential Real Estate. By logging on to ziprealty.com, you are authorizing ZipRealty to refer you to Coldwell Banker Residential Real Estate for real estate brokerage services, and ZipRealty will receive a referral fee or other valuable consideration for such referral.
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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 2014 Mid Florida Regional MLS. All rights reserved.

Data last updated: Thursday, October 30, 2014 at 7:56 PM