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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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$3,300,000
$12,226/mo
Monthly Payment:
$12,226
Principal & Interest:
$12,226
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $660,000 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 8,342sq ft $396 / sq ft SFR
Lot Size15,570sq ft Built2004 On Site201days
The Dream Estate! Your opportunity to own a masterpiece! This Classic Estate offers elegance, luxury and entertainment in the heart of desired Winter Park. With just a... more
The Dream Estate! Your opportunity to own a masterpiece! This Classic Estate offers elegance, luxury and entertainment in the heart of desired Winter Park. With just a short walk from all the fine restaurants and shopping on Park Avenue. As you enter this home you will be mesmerized with the attention to details given by the award winning builder's team Maroon Fine Homes & Marquis Fine Homes. The 3 story home features on the main level a formal living room with fireplace, family room, dining room, study, master bedroom and a gourmet kitchen with professional appliances. As you step into the temperature controlled lanai you will find an additional fireplace, summer kitchen and electronic hurricane shutters. Backyard offers room for outdoors entertaining, heated pool/spa and outdoor fireplace. You can take the fully operational elevator to the base level where you will find a fully equipped gym, climate controlled wine cellar, full wet bar, game room, movie theatre and 2 full suites. The home's top level features additional living space and 2 full suites. No description or photos can make justice to this stunning property!!!!! less
Listing Provided Courtesy of BHHS FLORIDA REALTY
Popularity
We show you every available listing. Here's how
$645,000
$2,389/mo
Monthly Payment:
$2,389
Principal & Interest:
$2,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $129,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,638sq ft $245 / sq ft SFR
Lot Size11,933sq ft Built1997 On Site201days
Desirable single story home, with three bedrooms, three full baths, and guest apartment in the heart of Winter Park! Located on a quiet circle, minutes from Park Avenue and... more
Desirable single story home, with three bedrooms, three full baths, and guest apartment in the heart of Winter Park! Located on a quiet circle, minutes from Park Avenue and nearby shops and dining, this home has a fantastic floor plan and offers over 2,600 square feet of living space, with formal living and dining, a large family room off the kitchen, and French doors that lead to the resort style pool and spa. Beautiful hardwood flooring has been laid throughout the home. Master bedroom is the perfect retreat with its vaulted ceilings, and en suite with his and her walk-in closets, double vanity, garden tub and shower. Each guest bedroom is generous in size and has their own private bath. Spacious kitchen with new GE appliances features travertine flooring, an over-sized closet pantry, bar-top seating, built-in work-space, and breakfast nook. Family room is radiant with natural light that fills the space from the windows and French doors. Wood burning fireplace and built-in entertainment center help create the perfect entertainment space. Step outside and be inspired by the gorgeous backyard. Vinyl fencing around the property provides privacy, while the brick pavers, vine covered trellis, and stunning pool bring characteristic charm. Above the two-car, detached garage, is a guest apartment with office, half bath, and efficiency kitchen. Zoned for A-rated schools; Brookshire Elementary, Glendridge Middle, and Winter Park High. Schedule your showing today! less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
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
5bed 4bath 3,064sq ft $244 / sq ft SFR
Lot Size8,775sq ft Built2008 On Site204days
Beautiful 5 bedroom Winter Park home in prime location with A+ Schools. Walk to Baldwin Park, Winter Park, close to airport. This home features wood floors, large kitchen with... more
Beautiful 5 bedroom Winter Park home in prime location with A+ Schools. Walk to Baldwin Park, Winter Park, close to airport. This home features wood floors, large kitchen with beautiful light cabinets and granite overlooking large fenced yard. First floor has 2 bedrooms, one currently being used as office. Upstairs 3 bedrooms and laundry. Yard has room for a pool. Call today to view this exquisite home! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
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
3bed 3bath 1,718sq ft $218 / sq ft SFR
Lot Size7,918sq ft Built1947 On Site205days
This beautiful 3 bedroom 2.5 bath 1718 sqft home was built in 1947. A cozy home for your family with a huge backyard perfect to add a pool, a garden, or some trees. Your front... more
This beautiful 3 bedroom 2.5 bath 1718 sqft home was built in 1947. A cozy home for your family with a huge backyard perfect to add a pool, a garden, or some trees. Your front porch will be surrounded with lush landscaping and private hedging. A brick walkway will lead you into your beautiful new home with original hardwood flooring. Walk to Park Avenue and enjoy the beauty that Winter Park has to offer! less
Listing Provided Courtesy of OLDE TOWN BROKERS INC
Popularity
$1,593,900
$6,105/mo
Monthly Payment:
$6,105
Principal & Interest:
$5,905
HOA Dues:
$200
(Based on a 30 year fixed loan at 3.75% with $318,780 down)
Winter Park, FL 32792
Seminole County School District
5bed 5bath 5,000sq ft $319 / sq ft SFR
Lot Size32,700sq ft Built2016 On Site206days
Pre-Construction. To be built. NEW CUSTOM HOME IN GATED COMMUNITY ON BEAR GULLY LAKE(SKI LAKE)! Home to be custom designed and built by Woodruff Construction. Home is... more
Pre-Construction. To be built. NEW CUSTOM HOME IN GATED COMMUNITY ON BEAR GULLY LAKE(SKI LAKE)! Home to be custom designed and built by Woodruff Construction. Home is subject to Buyer obtaining a construction loan and construction contract with Woodruff Construction. Elevation and interior photos are for conceptual purposes only. Photos are from a home Woodruff Construction completed in Winter Park in 2015. All room dimensions, square foot, and price are approximate. 5 Bed/ 4.5 Bath plus Study and Game Room and Bonus Room. Modern touches include two 10' tall disappearing glass walls in the Great Room, Thermador stainless steel gas appliance package, granite countertops throughout, hand made custom cabinet package and moldings, linear fireplace & disappearing motorized screens on rear covered patio, wood and marble flooring, contemporary pool package with LED lighting, huge pavered patio and deck for entertaining, custom ceiling details, Energy Saving features such as double pane Pella wood windows with Low E coating, injected foam in block walls, all interior walls and floors are insulated, 2 Tankless Water Heaters, tile roof, and paver driveway. Enjoy the convenience to downtown Winter Park and Park Avenue shopping, 417 and the airport, Trinity Prep, Masters Academy, the bike trail. Built by Woodruff Construction & Development, an MCBC Builder, this estate combines classic timeless design with a clean transitional interior. Call Richard for a personal tour of our latest custom estate in Winter Park. less
Listing Provided Courtesy of WOODRUFF REALTY, INC.
Popularity
$749,000
$3,357/mo
Monthly Payment:
$3,357
Principal & Interest:
$2,774
HOA Dues:
$583
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,773sq ft $270 / sq ft CND
Lot Size21,602sq ft Built2008 On Site207days
Lowest Priced Town Home in the Douglas Grand. Why pay more. Central Florida's most distinctive in-town living experiences. with all of the finishes and fixtures of a brand new,... more
Lowest Priced Town Home in the Douglas Grand. Why pay more. Central Florida's most distinctive in-town living experiences. with all of the finishes and fixtures of a brand new, modern-day building. Luxurious finishes are coupled with high-end appliances and fixtures in this two story 3 bed, 3 1/2 bath unit. Open floor plan with a large kitchen and dining area. The master bedroom with two (2) walk-in closets. The town home unit is finished with high quality finishes including Pella windows and doors, Kohler fixtures, Sub-Zero, Wolf and Bosch appliances, Trane air conditioning and other quality components the luxury Buyer demands. Crown molding, granite counter tops in the kitchen and all baths, walk-in closets in every bedroom, oversized walk-in shower and garden bath in the master suite, attached and covered parking and a private entry to the unit are also included. The Douglas Grand location is irreplaceable, one block from Park Avenue shopping district, across the street from Central Park, one block from Hannibal Square and walking distance to hundreds of retailers, restaurants and wine bars - a true city-living experience in Central Florida's most unique town - Winter Park. less
Listing Provided Courtesy of FLORIDA ONE REAL ESTATE LLC
Popularity
$2,099,000
$7,776/mo
Monthly Payment:
$7,776
Principal & Interest:
$7,776
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $419,800 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 6,138sq ft $342 / sq ft SFR
Lot Size20,335sq ft Built2002 On Site211days
***owner can move out quickly*gorgeous 5 bedroom home with lake view. When you enter through the double, hand carved, wood front doors, you will be greeted with the elegant... more
***owner can move out quickly*gorgeous 5 bedroom home with lake view. When you enter through the double, hand carved, wood front doors, you will be greeted with the elegant living room and fireplace. The formal banquet sized dining has a window seat and view of the lake. The office/library also has a fireplace. The gourmet kitchen has beautiful granite counters, 6 burner gas stove that will excite the chef in you. The kitchen flows into the family room and breakfast area. Off the family room is a bonus room full of light and french doors to the private patio and pool area. In-ground pool, the back yard is private.The master bedroom and 5th bedroom complete the first floor. Both have french doors to the pool area. There are 2 staircases to the upstairs. The main staircase leads you to a loft and balcony overlooking the lake,4th bedroom with a view of the lake, and two very large bedrooms with spacious connecting bath. There is also an additional room for storage or bonus room. The second staircase brings you to a large media and game room above the three car garage. Measurements are approximate . Brand new a/c installed 12/2015 less
Listing Provided Courtesy of TERZA REAL ESTATE
Popularity
$1,200,000
$4,562/mo
Monthly Payment:
$4,562
Principal & Interest:
$4,445
HOA Dues:
$117
(Based on a 30 year fixed loan at 3.75% with $240,000 down)
Winter Park, FL 32792
Seminole County School District
6bed 5bath 5,796sq ft $207 / sq ft SFR
Lot Size15,001sq ft Built2002 On Site212days
Stunning custom home in a gated community of 15 homes in winter park is waiting for a new owner. This spacious 6/4.5 home, 4-car garage, around 6,300 sq ft (per the seller) has... more
Stunning custom home in a gated community of 15 homes in winter park is waiting for a new owner. This spacious 6/4.5 home, 4-car garage, around 6,300 sq ft (per the seller) has something for everyone. First level features huge master bedroom overlooking the pool with a luxurious bathroom, huge mother-in-law or guest suite with private bath, large office with built-in bamboo shelves and flooring. The estate features custom contemporary kitchen with 42+ inch cabinets with blue pearl granite countertops, top of the line appliances including a sub-zero refrigerator, two dishwashers, island, gas cooktop. Family room is wrapped in custom cabinets adding convenient hidden storage space. Living room, which the owner uses as a music room, fits a grand piano and is separated from the master bedroom by a soundproof wall. The second floor offers three more bedrooms and two bathrooms, giant game room with bar and refrigerator, study den equipped with custom cabinetry, breathtaking upstairs patio overlooking a neighborhood pond and a lake! Top of the line insulation, 3 ac units, a water heater with re-circulating water flow secure the lowest utility bills in the neighborhood! Each room in the house is accentuated with custom ceiling designs, crown moldings, central vacuum and 12'-20' ceilings. Strategic floor plan layout is ideal for large family who loves to entertain. Custom outdoor kitchen and a saltwater pool with jacuzzi and a waterfall. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$659,000
$2,441/mo
Monthly Payment:
$2,441
Principal & Interest:
$2,441
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $131,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,764sq ft $238 / sq ft SFR
Lot Size15,722sq ft Built1955 On Site212days
Canal front home with direct access to the Winter Park Chain of Lakes. This one-story 4 bedroom traditional home is located in a quiet setting and set up perfect for... more
Canal front home with direct access to the Winter Park Chain of Lakes. This one-story 4 bedroom traditional home is located in a quiet setting and set up perfect for entertaining. Enjoy the waterfront setting directly in your back yard surrounded by nature. Exterior features include boat dock with lift, separate lift for wave runner or smaller watercraft, private pool, mature landscaping, and 2 porches for relaxing. Interior features include a split plan with 4 bedrooms, media room, family room with spectacular views of the canal and “preserve” across the canal, tongue and groove ceilings in family room, stainless steel appliances, wine storage closet, 2 wood burning fireplaces, and newly renovated master bathroom with granite countertops and large spa tub. All located in the Dommerich Elementary, Maitland Middle, and Winter Park High School district. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$489,000
$1,811/mo
Monthly Payment:
$1,811
Principal & Interest:
$1,811
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $97,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,209sq ft $221 / sq ft SFR
Lot Size6,750sq ft Built1945 On Site218days
Charming four bedroom home, paver driveway, w/wood and tile floors, formal living room with fireplace, stainless steel appliances, great room w/ vaulted ceilings, wet bar +... more
Charming four bedroom home, paver driveway, w/wood and tile floors, formal living room with fireplace, stainless steel appliances, great room w/ vaulted ceilings, wet bar + bonus room! Cozy neighborhood on brick one-way tree-lined street. Bike to Winter Park Village and Park Avenue stores. Highly rated school district. less
Listing Provided Courtesy of EZ CHOICE ASSOCIATES, INC
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 Site221days
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
$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 Site222days
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
$575,000
$2,263/mo
Monthly Payment:
$2,263
Principal & Interest:
$2,130
HOA Dues:
$133
(Based on a 30 year fixed loan at 3.75% with $115,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 3,595sq ft $160 / sq ft SFR
Lot Size14,943sq ft Built1993 On Site222days
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 (gas) 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
$1,185,000
$4,390/mo
Monthly Payment:
$4,390
Principal & Interest:
$4,390
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $237,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,700sq ft $320 / sq ft SFR
Lot Size9,655sq ft Built2015 On Site225days
Brand new! This spacious 5 bedroom custom home is located on a quiet tree lined street in the heart of winter park. At 3700 sq. Ft. This home boasts a huge master suite plus a... more
Brand new! This spacious 5 bedroom custom home is located on a quiet tree lined street in the heart of winter park. At 3700 sq. Ft. This home boasts a huge master suite plus a possible guest suite on the first floor. The first floor has beautiful hardwood flooring throughout. The master bath is appointed with dual sinks, tub, and separate shower stall. This home also features a luxury kitchen with gas range, built in appliances and gorgeous granite island. Conveniently located, the large dining room is connected to the kitchen. Perfect for entertaining, the kitchen and gathering area open up to a covered lanai and sparkling pool. An extra room on the first floor is perfect for an office, den, or formal living or dining area. Upstairs you will find a bonus space/loft area as well as three additional bedrooms with two baths. Highly acclaimed winter park schools, walking distance to the ymca, and just minutes from shopping and dining on park avenue! less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 3bath 2,486sq ft $201 / sq ft TWN
Lot Size5,258sq ft Built2002 On Site225days
Beautiful three bedroom, three bathroom townhome in prestigious Winter Park. From the moment you walk through the double front doors, you are welcomed by a bright and open floor... more
Beautiful three bedroom, three bathroom townhome in prestigious Winter Park. From the moment you walk through the double front doors, you are welcomed by a bright and open floor plan with plantation shutters throughout the home. The high ceilings and crown molding create a splendid atmosphere for both comfort and entertainment. The gourmet kitchen features an island, 42" custom cabinets, stainless steel appliances, granite counter tops, and under cabinet lighting. Located just off the kitchen is a large den/bonus room with custom built cabinetry, a full bath, the dining and living room combo with a wood burning fireplace, and two doors to the outdoor patio area. The wood staircase leads you to the an additional bonus area with a custom built-in desk. The master suite includes two walk-in closets and luxurious master bath with dual sinks, garden tub, and walk-in shower. Nestled around College Quarter, this home is perfectly located to enjoy all the shops and restaurants of Park Avenue, Rollins College, the Winter Park Public Library, and Farmer's Market. 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

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Friday, February 5, 2016 at 1:54 PM. Properties in listings may have been sold or may no longer be available.