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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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$325,000
$1,150/mo
Monthly Payment:
$1,150
Principal & Interest:
$1,150
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $65,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft SFR
Lot Size985sq ft Built1990 On Site40days
Rare boathouse opportunity for sale !! Boathouse, with low mileage 2014 boston whaler 170 montauk with mercury 90 efi fourstroke, on the winter park chain of lakes. Perfectly... more
Rare boathouse opportunity for sale !! Boathouse, with low mileage 2014 boston whaler 170 montauk with mercury 90 efi fourstroke, on the winter park chain of lakes. Perfectly tucked away behind rollins crew team boathouse at the curve on alabama ave, the 2nd boathouse in from the mouth of lake maitland. Gravel parking lot available for owner parking. One of the rare & exclusive boathouse exceptions that can be owned by someone other than a resident of the neighboring kronenberger subdivision. Freshly painted adirondack styled green exterior & brown interior, newly serviced electric boat lift, docked repaired and new stain, fishing rods rack, utility hooks and brand new remote controlled white garage door. Boathouse can be negotiated with or without the boat. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
We show you every available listing. Here's how
$895,000
$3,167/mo
Monthly Payment:
$3,167
Principal & Interest:
$3,167
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $179,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
2bed 3bath 2,033sq ft $440 / sq ft SFR
Lot Size6,935sq ft Built2000 On Site40days
Home has Full size Generator which supplies the home with power in the event the power goes out. Home also has hand made 8 ft doors made from heart pine. Iron railings around... more
Home has Full size Generator which supplies the home with power in the event the power goes out. Home also has hand made 8 ft doors made from heart pine. Iron railings around the patio upstairs and down stair and also in the front walk outs. less
Listing Provided Courtesy of FLORIDA REALTY INVESTMENTS
Popularity
$2,650,000
$9,378/mo
Monthly Payment:
$9,378
Principal & Interest:
$9,378
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $530,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 5,035sq ft $526 / sq ft SFR
Lot Size18,050sq ft Built2005 On Site40days
Elegant Mediterranean Estate custom built by Posada in the middle of downtown Winter Park on prestigious Park Avenue. The main residence sits on almost half an acre and also has... more
Elegant Mediterranean Estate custom built by Posada in the middle of downtown Winter Park on prestigious Park Avenue. The main residence sits on almost half an acre and also has a guest apartment with bedroom, full bath, and kitchenette. High-end finishes include arched French doors, Travertine marble floors, custom iron work, beamed ceilings, arches and columns, and authentic barrel tile roof. Downstairs master suite is the epitome of luxury with grand bathroom and a large walk-in closet. The upstairs has 3 bedrooms plus bonus area. Chefs kitchen features large granite island, 6-burner Thermador gas range, Thermador refrigerator and freezer, compactor, dishwasher, warming oven and many beautiful cabinets and granite counters. Adjacent butler's pantry/wine bar has sink, 2nd dishwasher, beverage refrigerator and 2 large Avanti wine refrigerators. Other extras include 3 fireplaces, surround sound, a double and a single garage, wrought iron automatic security gate, all new landscaping & lighting, curved brick driveway, & front fountain. The backyard is a private oasis with beautiful entertaining space, including a fireplace, and lovely pool. The residence has been well maintained, shows magnificently, and is the BEST location in town. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,350,000
$4,777/mo
Monthly Payment:
$4,777
Principal & Interest:
$4,777
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $270,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,208sq ft $321 / sq ft SFR
Lot Size18,800sq ft Built2001 On Site40days
Four bedroom, four and one-half bath pool home tucked quietly in one of Winter Parks charming neighborhoods. Downstairs master bedroom, home office/den, formal living and dining... more
Four bedroom, four and one-half bath pool home tucked quietly in one of Winter Parks charming neighborhoods. Downstairs master bedroom, home office/den, formal living and dining rooms, and an open kitchen/family room make this homes interior layout very desirable for day to day living. Beautiful kitchen with breakfast nook features a large granite island, GE Monogram refrigerator, and a 5-burner gas range. Just off the kitchen is the homes family room, with French doors that open to the covered patio and screened pool and spa. Master bedroom offers a spacious en suite with double vanities and jetted tub, as well as his and her walk-in closets. Upstairs youll find not one, but two, bonus/game rooms and a charming reading room. Each guest bedroom has a full bath and great closet space. Located on a quiet cul-de-sac, this Tuscan inspired home sits on almost a half-acre lot and has been meticulously landscaped with stunning rose gardens. Zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High, this active community is within a short distance to Lake Lily, Park Avenue shops and restaurants, Hannibal Square and the Winter Park Golf Course. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$175,000
$619/mo
Monthly Payment:
$619
Principal & Interest:
$619
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $35,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size10,500sq ft BuiltN/A On Site40days
Excellent opportunity to build your dream home on this large 75' wide lot in Dubsdread Heights. Much larger than the average College Park lot. Winter Park address within a view... more
Excellent opportunity to build your dream home on this large 75' wide lot in Dubsdread Heights. Much larger than the average College Park lot. Winter Park address within a view of Dubscread Golf Course. Since a house on the property was demolished in 1999 the impact fees are minimal. All survey and soil test work has been completed. The property is located one block from the newly renovated Dubsdread Golf course and very convenient to I-4, High end custom homes all around. Seller is currently using the property for their garden. less
Listing Provided Courtesy of OLDE TOWN BROKERS INC
Popularity
$465,000
$2,495/mo
Monthly Payment:
$2,495
Principal & Interest:
$1,645
HOA Dues:
$850
(Based on a 30 year fixed loan at 3.38% with $93,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,336sq ft $348 / sq ft CND
Lot Size3.3acre Built1921 On Site40days
Luxurious condo in the heart of historic Olde Winter Park, evoking images of an Old Southern Plantation with all it's charm and romance. Beautiful finishing touches that include... more
Luxurious condo in the heart of historic Olde Winter Park, evoking images of an Old Southern Plantation with all it's charm and romance. Beautiful finishing touches that include detailed trim & drywall moulding, elegant lighting, and built ins throughout this lovingly maintained home. Fully equipped kitchen highlighted with a chandelier in the trey ceilings, stainless steel appliances & eat in space. Wood flooring in the living areas, carpet in the bedrooms. Outstanding amenities to enjoy all of Winter Park's finest luxuries include 5 acres of meticulously maintained landscaped grounds, boat dock, lakefront wrap-around porch overlooking the swimming pool. Also included in the amenities are elevators, fitness center and clubhouse, and access to Lake Maitland. Near fine dining, boutique Park Avenue shopping and the popular Farmers Market. less
Listing Provided Courtesy of KELLER WILLIAMS CLASSIC REALTY
Popularity
$315,000
$1,114/mo
Monthly Payment:
$1,114
Principal & Interest:
$1,114
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $63,000 down)
Winter Park, FL 32789
Orwin Manor Orange County School District
3bed 2bath 1,626sq ft $194 / sq ft SFR
Lot Size7,420sq ft Built1950 On Site41days
Here is your chance to buy in Garden Acres of Winter Park. Just a stone throw from Park Ave, Downtown Orlando, Rollins College, and Florida Hospital. Let your imagination go... more
Here is your chance to buy in Garden Acres of Winter Park. Just a stone throw from Park Ave, Downtown Orlando, Rollins College, and Florida Hospital. Let your imagination go wild with this solid block home with updated plumbing and electrical already completed. The home sits on a very nice lot with mature oaks and plenty of room for a pool. Would make a great home for an owner occupant who would like to put their own touch of style in their new home, or perfect for the savvy investor as well. less
Listing Provided Courtesy of CENTURY 21 CARIOTI
Popularity
$389,900
$1,462/mo
Monthly Payment:
$1,462
Principal & Interest:
$1,379
HOA Dues:
$83
(Based on a 30 year fixed loan at 3.38% with $77,980 down)
Winter Park, FL 32792
4bed 3bath 2,267sq ft $172 / sq ft SFR
Lot Size7,405sq ft Built2014 On Site41days
Here's your chance to live in the highly sought after neighbourhood of Enclave at Aloma. Only two years old, Beautiful upgrades throughout. Ceramic title covering entire first... more
Here's your chance to live in the highly sought after neighbourhood of Enclave at Aloma. Only two years old, Beautiful upgrades throughout. Ceramic title covering entire first floor. Very private lot backs to trees. Screened in 36x10 back porch. Hardwired for surround sound in family room and back patio. Covered front porch. Bonus room/loft upstairs. Built in Cabinets in den/office/dining room. Extra storage in garage. Shows like a model home. less
Listing Provided Courtesy of OWNERS.COM
Popularity
$1,250,000
$4,423/mo
Monthly Payment:
$4,423
Principal & Interest:
$4,423
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $250,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,576sq ft $350 / sq ft SFR
Lot Size9,644sq ft Built2007 On Site41days
This exquisite Winter Park home was custom built by Brannon Construction. With more than 3,500 square feet of living space, this beautiful family home offers 4-bedrooms,... more
This exquisite Winter Park home was custom built by Brannon Construction. With more than 3,500 square feet of living space, this beautiful family home offers 4-bedrooms, 3-baths, and 2-half baths. The gourmet kitchen is fully equipped with gas appliances, granite counters, and cherry cabinets. Additional rooms include a large game room with a custom bar, an exercise room with rubber gym flooring, a formal dining room, and a music room with a cast stone fireplace. The home is exceptionally appointed with Brazilian cherry wood and travertine floors, 8 crown molding and baseboards, wood shutters, wrought iron railings and balusters, wainscot walls, central vacuum, custom closets, and a multi-functional sound system. Relax in the backyard with a full summer kitchen and enjoy the saltwater pool surrounded by a travertine deck while being cooled by the misters. Toy storage is plentiful with an attached two-car garage enclosed with pecky cypress doors and a detached garage behind the pool area. Centrally located, your family is directly around the corner from the Winter Park YMCA and Phelps Park, a brief ride to downtown Winter Park and Park Avenue, and minutes by car to Interstate 4 and State Road 436. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$83,900
$296/mo
Monthly Payment:
$296
Principal & Interest:
$296
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $16,780 down)
Winter Park, FL 32792
1bed 1bath 793sq ft $106 / sq ft CND
Lot Size19.0acre Built1970 On Site41days
Cute, clean four seasons condo. Move in ready 2nd floor unit. Great location in fabulous winter park. Close to downtown, rollins college & ucf. Wood floors, freshly painted,... more
Cute, clean four seasons condo. Move in ready 2nd floor unit. Great location in fabulous winter park. Close to downtown, rollins college & ucf. Wood floors, freshly painted, appliances and tranquil views from your private balcony. Steps to the laundry facilities. Look what the hoa covers; bldg. Exterior maintenance, pool, escrow reserve funds, ground maintenance, bldg. Insurance, manager, pest control, private road, recreational facility, roof, tennis courts, trash removal, water/sewer all for only $310 per month. Great opportunity for owner occupant or investor. Easy to show! less
Listing Provided Courtesy of LA ROSA REALTY, LLC
Popularity
$1,299,000
$4,818/mo
Monthly Payment:
$4,818
Principal & Interest:
$4,597
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.38% with $259,800 down)
Winter Park, FL 32789
Windsong Orange County School District
5bed 5bath 3,787sq ft $343 / sq ft SFR
Lot Size11,064sq ft Built2013 On Site41days
Newly constructed house. Never used after construction. Beautiful community and good surrounding schools. Nearby winter park city owned playground. Access to chain of Lakes.
Newly constructed house. Never used after construction. Beautiful community and good surrounding schools. Nearby winter park city owned playground. Access to chain of Lakes. less
Listing Provided Courtesy of GOLDEN SUN REALTY INC
Popularity
$285,000
$1,009/mo
Monthly Payment:
$1,009
Principal & Interest:
$1,008
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.38% with $57,000 down)
Winter Park, FL 32792
Seminole County School District
5bed 3bath 1,864sq ft $153 / sq ft SFR
Lot Size7,875sq ft Built1970 On Site41days
Seller wants to see all offers! This gorgeous updated 5 bedroom & 3 bath winter park home featuring lots of modern updates with a retro feel is now available! The many features... more
Seller wants to see all offers! This gorgeous updated 5 bedroom & 3 bath winter park home featuring lots of modern updates with a retro feel is now available! The many features include an open floor plan with formal living/dining area, family room right off the kitchen, large bright windows, fresh new paint of modern & trending color palettes inside & out, all new ceilings fans, satin nickel hardware & light fixtures throughout, window blinds, newer hvac & brand new video/audio wi-fi doorbell with remote cell phone access. The master features a california style walk-in closet, updated bath & double french doors that lead out to the huge florida room with tile flooring & glass windows for year round use. The newly updated kitchen has granite counter tops with breakfast bar, stainless steel dishwasher & microwave, recessed lighting, garbage disposal, stainless steel sink with pull-down sprayer faucet, new cabinets & beautiful glass tile backsplash. The all new laminate flooring is not only beautiful; it is also commercial grade & all bedrooms feature new frieze carpet. Other features include 2 car garage with an electronic opener, washer/dryer hookups & 3rd full bath, brand new architectural shingle roof, concrete block construction, fenced backyard, tropical landscape with over a dozen palm trees & solar landscape lighting. Seller will provide an appliance allowance with acceptable offer. Conveniently located to shopping, dining, ucf, full sail, beaches, excellent high rated schools & downtown winter park. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$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
5bed 3bath 3,650sq ft $233 / sq ft SFR
Lot Size12,678sq ft Built1993 On Site41days
Fantastic Winter Park Pool Home on Large Lot across from beautiful Lake Knowles. Bright and Spacious Floorplan offers your choice of 5 or 6 Bedrooms, 1 Bedroom on the First... more
Fantastic Winter Park Pool Home on Large Lot across from beautiful Lake Knowles. Bright and Spacious Floorplan offers your choice of 5 or 6 Bedrooms, 1 Bedroom on the First Floor, 3 Full Baths and a 2nd Floor Balcony overlooking the Lake. Dramatic entryway with double story foyer. Views of the pool from the Kitchen and Family Room. Tasteful Dcor. Volume Ceilings and Oversized Rooms throughout. Family Room boasts sliding doors to the pool and a fireplace, perfect for entertaining. Updated Kitchen in 2009 features granite counters, 42 cabinets, island, tile floor and stainless steel appliances. Master Bedroom ensuite features oversized bedroom with sitting area perfect for relaxing after a long day. Plenty of storage. Newer A/C system, roof and tankless water heater in 2009. New courtyard driveway and irrigation system 2015. New pool filter, exterior paint, carpet and French doors to balcony in 2016. Located close to Downtown Winter Park and Park Avenue offering the best in dining, shopping, and lifestyle. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$448,800
$1,588/mo
Monthly Payment:
$1,588
Principal & Interest:
$1,588
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $89,760 down)
Winter Park, FL 32792
Golfside Orange County School District
5bed 3bath 2,392sq ft $188 / sq ft SFR
Lot Size12,803sq ft Built1969 On Site42days
If you are looking for a 4+ bedroom house in one of the best school districts in Central Florida, then you have found it! Previously owned by prominent Winter Park physician... more
If you are looking for a 4+ bedroom house in one of the best school districts in Central Florida, then you have found it! Previously owned by prominent Winter Park physician this house is on the market for the first time. Located on the oak lined streets of the Golfside neighborhood and backing up to the Cady Way Trail, this is a truly rare find in Winter Park. This 5 bedroom, 3 bath home is within a short walk to both Winter Park High School and Brookshire Elementary Schools with Glennridge Middle School only 1.6 miles away. The heart of this community is the Winter Pines Golf course sitting less than 200 yards from your front door step to the east. The corner lot is spacious at just under 1/3 of an acre with its enormous front yard and private garden behind the house replete with mature, flowering azaleas and bougainvillea. Air conditioned Florida rooms adds another 240+- square feet of great entertaining space to this fantastic home. The three car garage provides for plenty of room for multiple vehicles while leaving room for storage via the attic and additional bonus room. less
Listing Provided Courtesy of SMITH MCINTOSH PROPERTIES, INC
Popularity
$809,999
$2,866/mo
Monthly Payment:
$2,866
Principal & Interest:
$2,866
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $162,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,461sq ft $234 / sq ft SFR
Lot Size12,679sq ft Built2014 On Site42days
Built in 2014 this Winter Park custom home is perfectly located and has all the upgrades for your most discriminating buyer. This home is set on an oversized lot with a large... more
Built in 2014 this Winter Park custom home is perfectly located and has all the upgrades for your most discriminating buyer. This home is set on an oversized lot with a large yard and has easy access to Florida Hospital, YMCA, the Park Avenue Retail District, Whole Foods, Rollins College, UCF, and a short drive to downtown Orlando without driving I-4! The transitional open floor plan includes beautiful Hickory wood floors, cathedral ceilings, crown moldings throughout, surround sound, French doors, double pane windows, and master and guest suites downstairs. The chefs kitchen is equipped with Bosch stainless appliances, solid wood cabinets, and granite counter tops. The spacious master suite has his and her closets, granite countertops, walk-in shower, and Jacuzzi tub. Also, downstairs you will find a separate office, formal dining, laundry room, and eat-in area next to the kitchen. A beautiful winding staircase which leads you upstairs to 2 large bedrooms, gorgeous bathroom, and a bonus area. Other features include an attached 2 car garage and detached single garage, large yard with mature landscaping, and covered back porch perfect for entertaining. Great A rated Winter Park schools.. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
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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: Monday, May 30, 2016 at 9:54 AM. Properties in listings may have been sold or may no longer be available.