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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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$346,500
$1,956/mo
Monthly Payment:
$1,956
Principal & Interest:
$1,226
HOA Dues:
$730
(Based on a 30 year fixed loan at 3.38% with $69,300 down)
Winter Park, FL 32789
2bed 2bath 1,148sq ft $302 / sq ft CND
Lot Size1.6acre Built1969 On Site54days
Completely renovated two bedroom, two bath unit at Lake Virginia Condos. Top floor, end unit has gorgeous views of both Lake Virginia AND the canal and a screened-enclosed... more
Completely renovated two bedroom, two bath unit at Lake Virginia Condos. Top floor, end unit has gorgeous views of both Lake Virginia AND the canal and a screened-enclosed balcony that provides the perfect space to relax and take in the scenic beauty. Elegantly decorated, the home has been updated to showcase hardwood floors in both the master and guest bedroom, stone flooring throughout the living areas, remodeled bathrooms, and a gorgeous kitchen complete with granite counters, custom solid cabinetry, and newer appliances. Dry bar with built-in wine refrigerator just off the dining room is great for entertainment and additional storage. Located right around the corner from Park Avenue, Lake Virginia Condominiums offers residents a short walking distance to nearby shops and restaurants, a community pool, assigned parking, and chain-of-lake access. With panoramic views and a modern interior, this home is by far one of the best units in the building. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
Your search results are current and complete. Learn more
$2,848,000
$10,079/mo
Monthly Payment:
$10,079
Principal & Interest:
$10,079
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $569,600 down)
Winter Park, FL 32789
Orange County School District
3bed 5bath 4,160sq ft $685 / sq ft TWN
Lot Size15,232sq ft Built2016 On Site54days
Pre-construction, to be built. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen... more
Pre-construction, to be built. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park Avenue, across the street from the Alfond Inn, and just a stones throw from the Winter Park Chain of Lakes. Comprised of six exquisitely appointed townhouses, South Interlachen Place is being built with premium level specifications; a standard of luxury usually only found in cosmopolitan world-class destinations. Award winning architect, Randall Slocum of Slocum Platts Architects, placed privacy as his top priority in creating the design for South Interlachen Place. Every fee-simple residence has a private two-car garage, private elevator to all levels, and lush, mature landscaping defining the entrances. A truly unique aspect of the design is the extraordinarily large and private roof top terrace for each individual residence providing both covered and open areas for outdoor dining and entertaining; each with a fireplace and powder bath. The residences are designed with "universal" features throughout; allowing for invisible accessibility that can respond to changing life styles. Each townhouse embraces smart technology for entertainment, lighting, energy management and security. There is just too much more to list here. Live in one of the most beautiful Winter Park residences in a truly exceptional downtown location - live at South Interlachen Place. less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
$725,000
$2,565/mo
Monthly Payment:
$2,565
Principal & Interest:
$2,565
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $145,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,289sq ft $220 / sq ft SFR
Lot Size11,226sq ft Built2004 On Site54days
Open Sun Jun 5, 2pm-4pm
Stunning custom designed four bedroom, three and one half bath home located on one of the most quiet streets in Winter Park! Amazing floor plan with more than 2,900 square feet... more
Stunning custom designed four bedroom, three and one half bath home located on one of the most quiet streets in Winter Park! Amazing floor plan with more than 2,900 square feet of living space showcases a formal dining room, a spacious kitchen overlooking the light and bright family room, a private master suite, a first floor office/den and a second story bonus room! This house has it all! Finishes include hardwood flooring, crown molding, high ceilings and plantation shutters. The kitchen offers stainless appliances, granite countertops, a breakfast area and bar stool seating. Adjacent butler's pantry leads into the separate formal dining room. Downstairs master bedroom is generous in size with a walk in closet, soaking tub with separate shower and a dual sink vanity. A home office/den completes the home's first floor. Three additional bedrooms and a bonus room are located on the second story. Enjoy looking out over the beautiful neighborhood from the upstairs front balcony. A two-car garage is set back in the rear of the property with ample storage space. Minutes from Park Avenue, walk thru some of Winter Parks charming neighborhoods to your favorite shops and restaurants. Call to schedule your showing today! less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,295,000
$4,582/mo
Monthly Payment:
$4,582
Principal & Interest:
$4,582
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $259,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 4,328sq ft $299 / sq ft SFR
Lot Size10,899sq ft Built1976 On Site55days
Elegant "VIA BELLA home nestled on one of WINTER PARKs most sought-after streets. Traditional brick architecture and pedestrian access to Lake Osceola comes with this classic... more
Elegant "VIA BELLA home nestled on one of WINTER PARKs most sought-after streets. Traditional brick architecture and pedestrian access to Lake Osceola comes with this classic home. Lush and mature landscaping creates complete privacy. Florida outdoor living with entertainment areas, pool bath, summer kitchen and tropical pool with terraced flagstone pool deck. This home is for entertaining! Gorgeous kitchen with gourmet appliances, custom cabinets, Carrara marble counter tops and a farmhouse sink. Olde world charm brick archway that takes you from the kitchen into a breakfast nook w/ beautiful natural lighting that overlooks the pool. The spacious formal dining room flows into a living room with a fireplace, tongue/groove ceilings, and glass doors that open out to the outdoor patio. Lower level has well-appointed stately office/ study with a wood-burning fireplace, tongue & groove wood ceiling and French doors leading out to the summer kitchen. Spacious Master bedroom, new master bath, enormous 204 SF walk-in closet, French doors open to a private screened patio off the Master Suite, and 12x12 flex room that is perfect for an art studio or workout room. Second bedroom has vaulted ceilings that flow into a 15X15 sitting area with tons of storage/closet space. This home is equipped with a whole house generator and is on well irrigation. This elegant Winter Park home has been extensively renovated. Walking distance to PARK AVE boutiques and restaurants. Home was appraised in March 2015 for $1,470,000. less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$289,900
$1,025/mo
Monthly Payment:
$1,025
Principal & Interest:
$1,025
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $57,980 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,216sq ft $238 / sq ft CND
Lot Size2,504sq ft Built1983 On Site56days
New Price!! Located in Winter Park, close to Rollins College and Park Avenue, this ground floor 2 bedroom 2 bath split plan condo with a backyard and garage bay is a true find.... more
New Price!! Located in Winter Park, close to Rollins College and Park Avenue, this ground floor 2 bedroom 2 bath split plan condo with a backyard and garage bay is a true find. Light bright and airy, the living area is open and framed with sliding glass doors. A wood burning fireplace warms the few cold days we have in Florida. Through the sliding glass doors, you can see the back yard with a wooden deck, benches, and planters. The kitchen has lots of cabinets, glass tile back splash, closet pantry, and all appliances. There is an eat-in area in the kitchen as well. An attached one car garage bay includes the washer/dryer hookup, water heater, and storage area. There are only four units in Azalea Lane Condos and the Association is run by the Owners. The complex is scheduled for painting. Super location! less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity
$899,000
$3,181/mo
Monthly Payment:
$3,181
Principal & Interest:
$3,181
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $179,800 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
4bed 4bath 3,022sq ft $297 / sq ft SFR
Lot Size11,250sq ft Built1920 On Site57days
Stunning & Perfectly Private POOL Home. Superbly located in the Heart of Olde Winter Park where you can WALK to exceptional Restaurants & Shopping on PARK AVE., the Farmers... more
Stunning & Perfectly Private POOL Home. Superbly located in the Heart of Olde Winter Park where you can WALK to exceptional Restaurants & Shopping on PARK AVE., the Farmers Market, great local events and more! Nestled on a Beautiful, Lushly Landscaped 75 x 150 lot, on a quaint tree lined street. This 4 Bedrm, 3 1/2 Baths home includes a detached 360 Sq.Ft. Guest House which opens to the pool and offers a large open Bedroom, Full Bathroom & Closet, makes a wonderful In Law Suite, Office, Game or Exercise Rm, whatever you would like. Additionally includes a 2 Car Garage that current owners are using as an Air Conditioned Playroom (this is not included in the living Sq.ft.). Tremendous Character & Amazing Architectural Details await you from the moment you step into the foyer, including Gorgeous Hardwood Floors throughout, 3 Wood Burning Fireplaces, French Doors, Gorgeous Moldings, & True Craftsmanship. Light and Bright floor plan w/ high ceilings & generous living areas. Newer kitchen w/ Carrara Marble Counters, Custom Cabinets, Step-in Pantry, and a Breakfast Nook with French doors & Screens leading out to the Serene Backyard Oasis, POOL and GUEST HOUSE. Completely PRIVATE and SPACIOUS BACK YARD Area. Amazing Curb Appeal, Convenient circular drive and Professional Landscaping welcome you home. Even has residents only LAKE ACCESS, with a Tranquil Park overlooking Beautiful LAKE VIRGINIA with Kayak & Canoe Storage. Dont Miss this Wonderful Home, with Excellent Winter Park Schools in a Phenomenal Location! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$875,000
$3,096/mo
Monthly Payment:
$3,096
Principal & Interest:
$3,096
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $175,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,717sq ft $235 / sq ft SFR
Lot Size11,374sq ft Built2007 On Site57days
Lovely traditional home with an open floor plan of how we love to live today. Hardwood floors almost everywhere, tall ceilings, columns and extensive woodwork and trim. Large... more
Lovely traditional home with an open floor plan of how we love to live today. Hardwood floors almost everywhere, tall ceilings, columns and extensive woodwork and trim. Large Great room is graced with a gas fireplace with a custom marble mantle and surround, with detailed wrought iron work. Great room is all open to the Dining area and spectacular Chef's Kitchen with rich warm wood cabinets, granite counters and a huge eat at, center island. High end appliances include Sub-Zero refrigerator, Dacor gas 5 burner cook-top, Thermador ovens/warming drawer and Fisher-Paykel double drawer dishwasher. Amazing home office has custom built-in cabinetry with LED under cabinet lighting and a double sided desk. 2 bedrooms are located on the main level, each with a bath. Upstairs floor is an entire Master wing, encompassing the Master bedroom with a breakfast balcony, luxurious Master bath, separate flex space room (home theater, nursery or exercise) a closet the size of a large bedroom and a ladies study or craft room. The exterior features a covered rear paver patio that is perfect for entertaining, lovely tropical pool with a swim out platform and a separate rear fenced area, for your own garden and with a storage shed. Energy efficient home with spray foam insulation and LED lighting. Best of all the public schools and within short distance to the YMCA and Phelps Park. Convenient to Winter Park Hospital, shopping and restaurants. less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity N/A
$849,000
$3,004/mo
Monthly Payment:
$3,004
Principal & Interest:
$3,004
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $169,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,651sq ft $320 / sq ft SFR
Lot Size8,070sq ft Built2005 On Site58days
Renovated in 2015.....Exquisitely updated Mediterranean home in the heart of Winter Park that has all the current upgrades for your most discriminating buyer. This home bodes 3... more
Renovated in 2015.....Exquisitely updated Mediterranean home in the heart of Winter Park that has all the current upgrades for your most discriminating buyer. This home bodes 3 bedrooms, 2.5 baths, office/living room with hidden temperature controlled storage/wine room, separate dining room, and a chefs kitchen open to the large gathering room overlooking the resort style pool. Interior features include gorgeous hardwood floors, 10 ceilings, beautiful molding throughout, and LED lighting. The newly renovated kitchen comes equipped with new stainless appliances, custom cabinetry, and granite countertops. Upstairs you will find the lavish master retreat inclusive of an oversized (12x13) custom walk-in closet, and a beautiful bathroom with walk-in shower and separate soaker tub. Other features include gas fireplace, plantation shutters, surround sound, and tankless water heaters. Outdoor living areas include a covered porch with tongue & groove ceilings, multiple seating areas, and gas fire features next to the luxurious pool. Above the 2 car garage is a large air-conditioned flex room perfect for exercise equipment, music room, additional office, or storage. Perfectly located with easy access to YMCA, UCF, Florida Hospital, Rollins College, and just minutes from the Park Avenue Retail District. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$124,900
$442/mo
Monthly Payment:
$442
Principal & Interest:
$442
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $24,980 down)
Winter Park, FL 32792
Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size3.3acre BuiltN/A On Site58days
Unbelieveable! Over 3 acres of vacant land in sought-after winter park!! This property is loaded with gorgeous oak trees in a serene setting close to everything. Part of this... more
Unbelieveable! Over 3 acres of vacant land in sought-after winter park!! This property is loaded with gorgeous oak trees in a serene setting close to everything. Part of this property is deemed as wetlands, however, there is over a 1/2 acre that is completely buildable per the county. This property is being sold in conjunction with lot 2g which is 1.1 acre. Buy them both and build custom dream homes! less
Listing Provided Courtesy of PROFITABLE PROPERTIES
Popularity
$99,000
$350/mo
Monthly Payment:
$350
Principal & Interest:
$350
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $19,800 down)
Winter Park, FL 32792
Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size1.1acre BuiltN/A On Site58days
WOW! Amazing opportunity to own over an acre of beautiful property with a Winter Park address!! Peaceful and quiet lot located close to everything and across from half million... more
WOW! Amazing opportunity to own over an acre of beautiful property with a Winter Park address!! Peaceful and quiet lot located close to everything and across from half million dollar homes. Build a custom home on this gorgeous lot which is cleared and ready to go. There is NO HOA here and it may be possible to get a variance to build more than one house on the property. Note that this is lot G and the contiguous Lot D with over 3 acres is also for sale. Possibilities galore!! Please respect the neighbors. There is a 15 foot right-of-way road easement the runs down the west side of the lot and then cuts across the north 15 feet of Lot C. The dirt road currently only extends as far as Lot C, so please park there and walk to this lot. less
Listing Provided Courtesy of PROFITABLE PROPERTIES
Popularity
$375,000
$1,327/mo
Monthly Payment:
$1,327
Principal & Interest:
$1,327
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $75,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size7,918sq ft BuiltN/A On Site59days
Walking distance to Park Ave. New construction in happening now all around this area. Million dollar + homes surrounding this property
Walking distance to Park Ave. New construction in happening now all around this area. Million dollar + homes surrounding this property less
Listing Provided Courtesy of LA ROSA REALTY, LLC
Popularity
$1,329,000
$4,703/mo
Monthly Payment:
$4,703
Principal & Interest:
$4,703
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $265,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,966sq ft $335 / sq ft SFR
Lot Size10,312sq ft Built2016 On Site61days
Under Construction New Modern style home designed by Davila Homes Construction. This bright open-floor plan is just minutes to downtown Winter Park, the famous Park Avenue and... more
Under Construction New Modern style home designed by Davila Homes Construction. This bright open-floor plan is just minutes to downtown Winter Park, the famous Park Avenue and Winter Park Village. The modern interiors were designed with clean lines, oversized iron front door, glass doors and windows to bring the outside in feeling. The first floor master suite has contemporary features, oversized walk-in closet, freestanding bath tub, and walk-in shower. This modern masterpiece also includes a formal dining room, flex space that can be used as an office/playroom/living room, 5 bedrooms, 4.5 bathrooms, gourmet kitchen, quartz counter-tops throughout, Sub Zero/Wolf Appliance Package, guest suite, over the top laundry room downstairs and upstairs, entertaining space upstairs with full bar setup, tankless water heater, hardwood floors in all bedrooms and Italian porcelain tile throughout. The great room overlooks the expansive outdoor living space that includes a contemporary design swimming pool, summer kitchen, fire pit area and covered lanai. This location is prime: 15 minutes commute Downtown Orlando, 30 minutes from Disney World, 10 minutes to the new Florida Hospital. less
Listing Provided Courtesy of NOVA REAL ESTATE SERVICES INC
Popularity
$284,000
$1,005/mo
Monthly Payment:
$1,005
Principal & Interest:
$1,005
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $56,800 down)
Winter Park, FL 32789
Orange County School District
1bed 2bath 850sq ft $334 / sq ft CND
Lot Size1.6acre Built1969 On Site61days
Beautiful panoramic lake views from this 4th floor unit. Condo is on Winter Park Chain. Nice bright and clean unit with upgraded tile floors. Rentable boat slips when available,... more
Beautiful panoramic lake views from this 4th floor unit. Condo is on Winter Park Chain. Nice bright and clean unit with upgraded tile floors. Rentable boat slips when available, lakeside pool and spa. under building parking. Fitness room and clubhouse plus rentable guest suite. Dog walk and much more. Walk to Park Ave, Rollins College, restaurants and shopping. less
Listing Provided Courtesy of WINTER PARK LAND CO.
Popularity
$3,450,000
$12,430/mo
Monthly Payment:
$12,430
Principal & Interest:
$12,209
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.38% with $690,000 down)
Winter Park, FL 32789
Windsong Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.5acre BuiltN/A On Site63days
Located in Windsong on a quiet cul-de-sac only 10 minutes from Downtown Orlando. This lot faces West and overlooks Rollins College. The total square footage of the lot is 64,407... more
Located in Windsong on a quiet cul-de-sac only 10 minutes from Downtown Orlando. This lot faces West and overlooks Rollins College. The total square footage of the lot is 64,407 sq. ft. (1.48 acres). There are 5 very beautiful large oak trees, one is about 350 years old and 15 cypress trees on the water. It is by far the best available vacant lot on the Winter Park Chain of Lakes. Plans are available for a gorgeous 9,782 sq. ft. home that was designed by Randall Slocum, architect. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$725,000
$2,565/mo
Monthly Payment:
$2,565
Principal & Interest:
$2,565
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $145,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,483sq ft $292 / sq ft SFR
Lot Size9,714sq ft Built2009 On Site65days
This modern Mediterranean-style residence located off Old Winter Park Road has been fully renovated, and no details have been overlooked. Features of the unique, three bedroom,... more
This modern Mediterranean-style residence located off Old Winter Park Road has been fully renovated, and no details have been overlooked. Features of the unique, three bedroom, three-and-a-half-bath home include an open floor plan with 12-foot ceilings and a tranquil view of the courtyard pool and spa as you enter the home. The master bedroom takes over the whole second floor and is a true owners retreat. The detached en suite bedroom would be perfect as an in-law suite or office. Some of the homes upgrades include a new HVAC unit, new flooring, kitchen updates, automatic electric blinds, sound system, security system and landscaping, just to mention a few. Behind the home, the oversized two-car garage with a single covered parking area attached is ideal for the car collector or craftsman. In an excellent location and a great school district, this beautiful home is minutes from downtown Orlando, Winter Park and I-4. less
Listing Provided Courtesy of PREMIER SOTHEBY'S INT'L REALTY
Popularity
10 11 12 13 14 15 16 17 18 ... 23
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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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Data last updated: Tuesday, May 31, 2016 at 8:00 PM. Properties in listings may have been sold or may no longer be available.