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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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$1,295,000
$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 5bath 4,510sq ft $287 / sq ft SFR
Lot Size15,749sq ft Built1926 On Site161days
1920's Modern Mediterranean in premier setting on oversized corner lot overlooking Lake Chelton and surrounded by majestic oaks and beautiful brick streets! This elegant 4... more
1920's Modern Mediterranean in premier setting on oversized corner lot overlooking Lake Chelton and surrounded by majestic oaks and beautiful brick streets! This elegant 4 bedroom home is bright & open sitting up high overlooking Lake Chelton wonderfully remodeled & preserved to maintain its historic charm and character! Original hardwood floors and Italian tile enhance the downstairs living areas, including the formal living and dining rooms, and breakfast nook. Designer island kitchen with gas appliances, custom cabinetry, and granite counter tops open to large family room with French doors to lanai... Also a fabulous sunroom with floor to ceiling glass arc windows offering panoramic views of the lake and a peaceful environment to relax in... Separate, outdoor screened patio is an extension of the indoor living space and continues the arc window design and Mexican tile flooring and great character... Upstairs master bedroom is oversized with sitting area, and French doors that open onto a walk-out terrace. Master bathroom is adorned with marble vanities and a marble Jacuzzi tub, walk-in shower, and expansive closet. Two additional guest suites, each with their own bath, and generous 4th bedroom suite/bonus room with wood burning fireplace complete the upstairs. Lastly, there is a detached two garage with covered walkway and a unique "hard to find" unfinished 2nd floor that could easily be converted into a guest apartment with full bath. Located in one of Winter Park's most picturesque neighborhoods. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
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$1,675,000
$6,205/mo
Monthly Payment:
$6,205
Principal & Interest:
$6,205
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $335,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 4,872sq ft $344 / sq ft SFR
Lot Size18,088sq ft Built1994 On Site161days
Custom built, original-owner canal home on Alabama Drive, one of the most beautiful tree lined streets in downtown Winter Park. Hand crafted by Peatross & Huber, the floor plan,... more
Custom built, original-owner canal home on Alabama Drive, one of the most beautiful tree lined streets in downtown Winter Park. Hand crafted by Peatross & Huber, the floor plan, amenities and attention to detail are timeless. Enter into grand foyer with vaulted ceilings and marble floors, flanked by elegant dining room with built in niches, and living room with double-sided gas fireplace. The downstairs boasts a luxurious master suite with pool view, a separate guest suite, and an office with wood beams, wood floors, and a magnificent set of etched glass French doors. Kitchen opens onto family room and has double ovens, Subzero refrigerator, an island, and butler’s pantry. There is also an indoor sunporch, as well as an outdoor screened porch with brick walls that feels like the best of coastal living! 3 Bedrooms + 3 baths upstairs plus bonus area. Features include crown molding, French doors, tray ceilings, hardwood floors, custom built-ins, and abundant storage. Pool area is lovely with outdoor grill and pergola, and home sits on almost a half-acre. Boat house included in sale but sold AS IS. The best location in town, easy walk to Park Avenue, and “A” rated Winter Park schools. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$800,000
$2,963/mo
Monthly Payment:
$2,963
Principal & Interest:
$2,963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $160,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size19,059sq ft BuiltN/A On Site165days
Big 150'x130 (approx) building lot (s), serene lake view setting, viewed from the front porch of your new custom home. 15 new homes under construction within 1/2 mile of this... more
Big 150'x130 (approx) building lot (s), serene lake view setting, viewed from the front porch of your new custom home. 15 new homes under construction within 1/2 mile of this location, up to $1.5M. Approved Winter Park City lot split into two 75x130 (approx) lots. See attachment for approval letter. City of Winter Park Building Codes apply. Value is in the land for one large or two separate building lots. Winter Park City maintained Lake Wilbar. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$2,595,000
$9,614/mo
Monthly Payment:
$9,614
Principal & Interest:
$9,614
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $519,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,285sq ft $413 / sq ft SFR
Lot Size32,129sq ft Built2011 On Site166days
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011... more
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011 with Hal George at Parkland Homes, top quality craftsmanship & exquisite trim / moldings thru-out, bright-open floor plan, high detailed ceilings, generous room sizes, designer lighting, lots of great windows & french doors... Fabulous 1st floor master retreat with lavish bath along with his & her baths/dressing areas... Wonderful huge gourmet island kitchen with commercial appliances & extensive cabinetry, elegant "club room" with full bar & paneled walls, large beautiful formal dining & living rooms with windows/french doors both sides, and a library downstairs... Upstairs includes 4 bedroom suites, game room & bonus room... The outdoor living is nothing short of spectacular with tremendous grounds, expansive covered lanai (invisible remote retractable screens), classic pool area & walled in private yard... Enjoy the Winter Park Racquet Club, tennis courts, & access to Lake Maitland "chain of lakes" next door... A perfect entertaining home & property!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$265,000
$981/mo
Monthly Payment:
$981
Principal & Interest:
$981
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,592sq ft $166 / sq ft SFR
Lot Size9,542sq ft Built1965 On Site166days
Winter Park Pines Beautiful home with multiple upgrades including newer roof, AC, stucco, gutters, electrical, paint. Tiled, sprinkler well and timer, fenced backyard, screened... more
Winter Park Pines Beautiful home with multiple upgrades including newer roof, AC, stucco, gutters, electrical, paint. Tiled, sprinkler well and timer, fenced backyard, screened porch, back deck and on a corner Lot. New Windows and Updated Baths. Mature Oak Trees and landscaping. A - Rated Winter Park Schools!! less
Listing Provided Courtesy of Florida Home Realty & Invest
Popularity
$199,900
$740/mo
Monthly Payment:
$740
Principal & Interest:
$740
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $39,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,788sq ft $112 / sq ft SFR
Lot Size14,000sq ft Built1961 On Site167days
Price reduced. Bring all offers! ....What a lot! If you are looking for a huge backyard with plenty of land, then look no further! This property is perfect for you. This 4... more
Price reduced. Bring all offers! ....What a lot! If you are looking for a huge backyard with plenty of land, then look no further! This property is perfect for you. This 4 bedroom 2 bath home is ideal for the family looking to settle down in a great area. Come see this home today! less
Listing Provided Courtesy of Century 21 Roo Realty
Popularity
$1,000,000
$3,704/mo
Monthly Payment:
$3,704
Principal & Interest:
$3,704
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $200,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,265sq ft $306 / sq ft SFR
Lot Size8,583sq ft Built2015 On Site168days
Stunning Custom Contemporary home that will exceed your client's expectations! This gorgeous home will have the master, study and second bedroom all on the first floor.... more
Stunning Custom Contemporary home that will exceed your client's expectations! This gorgeous home will have the master, study and second bedroom all on the first floor. The spacious open concept downstairs living, dining and eat-in kitchen boasts picturesque views of the luxurious resort style swimming pool viewed through the floor to ceiling panoramic sliding glass doors. The living room will also have a sleek, modern, flush mount fireplace to further enhance the luxury of this design. The study will boast a modern sliding barn door and the entry will have an IMPRESSIVE open riser cantilever stair system that will appear to be floating. The first floor master suite offers a private en suite master bath that boasts a "wet room" shower and stand alone tub, as well, as a private outdoor space with an additional shower. It also includes a stackable washer and dryer for convenience. The second floor has two additional bedrooms, a loft area, and a full laundry for servicing the upstairs living. This architect has made exceptional use of light via oversized windows throughout. The exquisite exterior will boast a Stacked Stone accent, exterior wood ceilings, a paver driveway, walk ways and lanai and a ten year warranty exterior paint system. This will be a must see for the most discerning clients!!! less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity
$359,000
$1,330/mo
Monthly Payment:
$1,330
Principal & Interest:
$1,330
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $71,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,935sq ft $186 / sq ft TWN
Lot Size4,775sq ft Built2002 On Site171days
Centrally located in the HEART of Winter Park on a brick-paved street, welcome to stress free living with NO HOA fees! The Mediterranean inspired townhome sits in a quiet... more
Centrally located in the HEART of Winter Park on a brick-paved street, welcome to stress free living with NO HOA fees! The Mediterranean inspired townhome sits in a quiet neighborhood overlooking a well-groomed park, complete with a tranquil pond and a fountain. Recent updates include NEW interior paint, NEW landscape, 4 NEW windows (12/2014), NEW gas hot water heater (2013), and refinished/screened wood floors (12/2014). The Kitchen features a gas stove with a Jen-Air grill, granite counters, and solid wood cabinets with abundance of storage. The breakfast bar opens to a large living room with a 35' ceiling. A separate office area with build-in computer desk, book shelves & storage is off the kitchen. A separate Dining room is off the open Living room, complete with marble-trimmed gas fireplace & custom built bookshelves. Upstairs includes all 3 bedrooms with bright guest bath. The grand master suite features a 12-jet therapeutic bathtub, separate shower , double sinks and a large walk-in closet. The townhome is "smart home" prewired for surround sound, security & an intercom to front door. A central vacuum & available Rainsoft water system make for more quality living. This townhome is TURN KEY ready for you. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$900,000
$3,334/mo
Monthly Payment:
$3,334
Principal & Interest:
$3,334
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $180,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size20,476sq ft BuiltN/A On Site171days
First time on market!! 125 feet on beautiful lake killarney! Build your dream home (5500 sq ft) on this double lot! 125 x 130 plus 125x60x25x128 lakefront/boathouse lot!
First time on market!! 125 feet on beautiful lake killarney! Build your dream home (5500 sq ft) on this double lot! 125 x 130 plus 125x60x25x128 lakefront/boathouse lot! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$99,999
$370/mo
Monthly Payment:
$370
Principal & Interest:
$370
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $20,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size7,001sq ft BuiltN/A On Site171days
Build your dream home on this vacant piece of land in Winter Park! 50x140' deep, flat lot is zoned R-2. Great neighborhood with quiet, brick streets, mature oaks trees, and... more
Build your dream home on this vacant piece of land in Winter Park! 50x140' deep, flat lot is zoned R-2. Great neighborhood with quiet, brick streets, mature oaks trees, and sidewalks. Centrally located, this home site is just minutes from Park Avenue, downtown Orlando, Florida Hospital’s Health Village and the I-4 corridor. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$214,999
$1,072/mo
Monthly Payment:
$1,072
Principal & Interest:
$796
HOA Dues:
$276
(Based on a 30 year fixed loan at 3.75% with $43,000 down)
Winter Park, FL 32789
2bed 3bath 1,536sq ft $140 / sq ft CND
Lot Size4,764sq ft Built1986 On Site172days
Price reduced for a quick sale! Motivated seller! Walk over to Trader Joe's! This urban 2-level condo in Winter Park has character and prime location! Killarney Bay is a... more
Price reduced for a quick sale! Motivated seller! Walk over to Trader Joe's! This urban 2-level condo in Winter Park has character and prime location! Killarney Bay is a beautiful lake front community with Lake Killarney access, a dock, tile roofs and a lakeside pool to enjoy the amazing Florida sunsets! Extremely convenient to Downtown Orlando, shopping, Park Ave, restaurants, Winter Park Village, I4 and much more! This 2-level remodeled property has 2 bedrooms and 2.5 baths with designated carport space at your doorstep. Double master suites with walk-in closets (2nd floor) and a spacious living room with a wood burning fireplace, a custom crafted bookshelf/desk and laminate wood floors. Open concept kitchen design with maple cabinets, Corian countertops, stainless steel appliances and snack bar. Other characteristics include a screened lanai, lots of storage space, balcony, newer carpet, newer AC system (inside and out), interior laundry room with the washer and dryer and a wet bar in the dining room. New interior paint. One year home warranty included. Run, don’t walk! less
Listing Provided Courtesy of Re/max Town Centre
Popularity
$900,000
$3,334/mo
Monthly Payment:
$3,334
Principal & Interest:
$3,334
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $180,000 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 1,444sq ft $623 / sq ft SFR
Lot Size20,476sq ft Built1949 On Site172days
125 feet on beautiful lake killarney! First time on market!! Outstanding opportunity to renovate charming 1949 bungalow or build your dream home (over 5500 sq ft) on this double... more
125 feet on beautiful lake killarney! First time on market!! Outstanding opportunity to renovate charming 1949 bungalow or build your dream home (over 5500 sq ft) on this double lot: 125 x 130 plus lakefront lot. Enjoy 239 acre, spring fed lake killarney: a serene place to call home with easy access to i-4/ downtown orlando or downtown winter park. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$699,000
$2,589/mo
Monthly Payment:
$2,589
Principal & Interest:
$2,589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,800 down)
Winter Park, FL 32789
4bed 4bath 2,648sq ft $264 / sq ft SFR
Lot Size5,996sq ft Built2015 On Site173days
Take advantage of our $10,000 Home Discount! And we’ll pay $7,500 towards your closing costs when you use our preferred lander and Title Company! But hurry, home must... more
Take advantage of our $10,000 Home Discount! And we’ll pay $7,500 towards your closing costs when you use our preferred lander and Title Company! But hurry, home must close on or before March 31, 2015! Start fresh and buy new in Winter Park’s oldest area! This new home has the garage in the back with a private gated alley access. Step back into time with the nostalgic Craftsman exterior style with all the modern materials, processes and energy efficiency. This floorplan has an oversized kitchen and island in the heart of the home, connected to the single dining room area, first floor master bedroom. The interior design selections have elegant transitional style with mixture of dark cherry wood slate kitchen cabinets and painted White Island in the kitchen to create the furniture feel to this oversized kitchen. Our designer beautifully blended with a soft white quartz countertop and earth tone glass tile backsplash so this home doesn’t miss a detail! Our Energy Saver Homes offer Homebuyers the best in energy-efficiency and are backed by our program’s heating and cooling energy usage guarantee. These homes are friendlier to you, the environment and your pocketbook… it’s a win-win-win! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$549,900
$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 $109,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,664sq ft $330 / sq ft SFR
Lot Size18,676sq ft Built1948 On Site173days
Olde World Charm is being brought back to life in this Winter Park bungalow! The discerning Buyer will appreciate the details lovingly done by the Seller throughout. From the... more
Olde World Charm is being brought back to life in this Winter Park bungalow! The discerning Buyer will appreciate the details lovingly done by the Seller throughout. From the pavered circle driveway, you arrive at the private entry. Passing through, notice the outdoor sitting area & garden areas recently added. Foyer greets you with travertine & stained glass window before entering the home on original refurbished Red Oak wood flooring. Great room includes a stunning marble fireplace with custom shelving just before you enter the bright Formal dining room through the alabaster mosaic columns. Throughout the home – solid wood interior doors, custom molding & trim work, reglazed windows & travertine in all wet areas. Kitchen offers a full complement of stainless steel appliances set off by the New kitchen with solid Maple cabinets & crown molding as well as separate Breakfast Nook. Owner’s suite flooring is solid bamboo & has a lovely sitting area with French doors & floor to ceiling windows to enjoy the natural light & private courtyard. Split floor plan with two guest bedrooms & shared bath on the opposite side of the home. Outdoors is such a pleasure from the pavered patio with custom canopy including ceiling fan in the fully landscaped & privacy fenced yard that extends over 200’deep making the property nearly ½ acre. Architectural shingle roof installed in 2011 before beginning the interior. Just a short bike ride to Downtown Winter Park, walk to Phelps Park, YMCA, Lake Knowles & Lakemont Elementary. less
Listing Provided Courtesy of Watson Realty Corp
Popularity
$249,900
$928/mo
Monthly Payment:
$928
Principal & Interest:
$925
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $49,980 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 1,596sq ft $157 / sq ft SFR
Lot Size10,346sq ft Built1964 On Site173days
Beautiful 4 bedroom/2 bath corner lot home in the heart of Winter Park. House has newer plumbing, A/C and upgraded electrical. Spacious kitchen features plenty of cabinets and... more
Beautiful 4 bedroom/2 bath corner lot home in the heart of Winter Park. House has newer plumbing, A/C and upgraded electrical. Spacious kitchen features plenty of cabinets and stainless steel appliances and granite breakfast bar. Home features some laminate wood, enclosed screened patio, bright and open living space, separate dining area, fenced yard. Home is close to downtown Winter Park, schools, hospital and Cady Way. Seller is motivated, quick answer to offers. Bring your buyers to see this one!! less
Listing Provided Courtesy of Homecenter Realty Associates
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Sunday, April 26, 2015 at 6:12 AM