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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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$625,000
$2,315/mo
Monthly Payment:
$2,315
Principal & Interest:
$2,315
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $125,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,869sq ft $334 / sq ft SFR
Lot Size7,302sq ft Built1940 On Site18days
This 1940 Bungalow is situated on one of the most beautiful and desirable tree lined streets in Winter Park. Lush landscaping leads you into this 4 bedroom 3 bath home. Two... more
This 1940 Bungalow is situated on one of the most beautiful and desirable tree lined streets in Winter Park. Lush landscaping leads you into this 4 bedroom 3 bath home. Two bedrooms feature their own on suite full bath. Enjoy your beautiful back yard while relaxing on your large deck with family and friends. Conveniently located to all your shopping, dinning and entertainment needs. This home is a must see. less
Listing Provided Courtesy of The K Co
Popularity
We show you every available listing. Here's how
$315,000
$1,167/mo
Monthly Payment:
$1,167
Principal & Interest:
$1,167
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,000 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 1,945sq ft $162 / sq ft SFR
Lot Size9,252sq ft Built1958 On Site18days
Located in beautiful Brookshire Heights in Winter park, this remodeled 4 bedroom 2 bath home is perfect for you. While keeping the charm and character of the area neighborhood... more
Located in beautiful Brookshire Heights in Winter park, this remodeled 4 bedroom 2 bath home is perfect for you. While keeping the charm and character of the area neighborhood in this established community, the renovations boast a large open kitchen with high end solid cabinets, soft close drawers, huge granite counters, and brand new stainless steel appliances. From the family room, new french doors with blinds in between panes open up to the shaded patio area perfect for relaxing. All new lighting, flooring, new paint, through out the house with all new bathrooms, and large windows throughout the house that embrace the nature lighting. Outside is a well maintained lush lawn, with a wide drive way, and new 2 car garage with "hidden laundry room." Close to the Historic District, you can enjoy shopping and dining on Park avenue. Of course this home is zoned for all A schools, including Brookshire Elementary, Glennridge Middle, and Winter Park High School. Great Parks, lots to do in this established community, this home is waiting for you! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$219,900
$814/mo
Monthly Payment:
$814
Principal & Interest:
$814
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $43,980 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 811sq ft $271 / sq ft SFR
Lot Size6,959sq ft Built1947 On Site18days
Absolutely darling! Updated 2 bed/1 bath bungalow in “red hot” location of Corrine Corridor. Walk to East End Market, restaurants and shops. Everything you need... more
Absolutely darling! Updated 2 bed/1 bath bungalow in “red hot” location of Corrine Corridor. Walk to East End Market, restaurants and shops. Everything you need and nothing you don’t…for modern urban living in Winter Park. High ceilings, ceramic and laminate flooring. Updated kitchen with stainless appliances and granite tops, open to living area. Light bright open plan – great for socializing and entertaining. Visit with neighbors on front deck or grill on back patio. Separate utility room with storage and laundry. Room for expansion in large backyard. Don’t miss this great opportunity! less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$985,000
$3,649/mo
Monthly Payment:
$3,649
Principal & Interest:
$3,649
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $197,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,161sq ft $237 / sq ft SFR
Lot Size16,136sq ft Built1965 On Site19days
Charming Cape Cod Revival renovated home with 5 bdrms/3 full baths/2 half baths on an expansive lot in prime Via location. This property is ideally located on a secluded cul de... more
Charming Cape Cod Revival renovated home with 5 bdrms/3 full baths/2 half baths on an expansive lot in prime Via location. This property is ideally located on a secluded cul de sac with towering trees in a wonderful area of Winter Park. Walking distance to Winter Park Racquet Club & minutes from downtown Park Ave/WP restaurants & shops. Features spacious Living & Dining rooms for formal entertaining with wood floors, crown molding & plantation shutters. The Kitchen hosts GE Stainless appliances, wine refrigerator with built in wine rack, snack bar counter plus eat in breakfast area. The Family room offers a built in media center, travertine mosaic tile & stone fireplace, surround sound & French doors out to spacious Lanai. Lanai has brick paver flooring, bead board composite ceiling & designer fans. Enormous Master has a separate sitting/exercise/office area & a gorgeous bath. One of the best features of the home is the detached home office/media room or playroom with wonderful wood floors, crown molding & inset lighting. The enormous backyard offers plenty of room to add a pool & outdoor summer kitchen & cabana, if desired. Don't miss the opportunity to live in this wonderful home in the very desirable WP School District! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$449,900
$1,666/mo
Monthly Payment:
$1,666
Principal & Interest:
$1,666
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $89,980 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,817sq ft $248 / sq ft SFR
Lot Size6,750sq ft Built1926 On Site19days
Stunning renovation in Historic Orwin Manor in Winter Park! Minutes from Park Avenue in Winter Park, Florida Hospital, Ivanhoe Village, College Park and Winter Park's restaurant... more
Stunning renovation in Historic Orwin Manor in Winter Park! Minutes from Park Avenue in Winter Park, Florida Hospital, Ivanhoe Village, College Park and Winter Park's restaurant row on 17-92. Kitchen and baths have all been updated. Narrow oak floors that shine, crown molding, wood burning fireplace and high ceilings. Kitchen has granite counter tops, stainless steel appliances and gorgeous cherry cabinets. Natural gas stove and hot water heater. All new electrical wiring in 2003. Master bath has two pedestal sinks and a nice tiled shower. All new tile in both upstairs baths. This home is perfect for entertaining with an open floor plan, French doors leading out to a beautifully landscaped back yard and wood deck. Cozy den for T.V. watching and office downstairs both have slate floors.The charming Orwin Manor neighborhood is the perfect location for anyone working in downtown Orlando or Winter Park. Jump on I-4 conveniently or avoid it all together with I-4 construction set to start this summer. Minutes from Loch Haven Park, Orlando Science Center, Dr. Philips Performing Arts Center and Amway Arena. This home is individually listed on the Register of Historic Places in the City of Winter Park. Outside of home painted in 2011. Wood deck re-stained in 2015. A pleasure to show. less
Listing Provided Courtesy of Sutton & Sutton Realty, Inc.
Popularity
$75,000
$587/mo
Monthly Payment:
$587
Principal & Interest:
$277
HOA Dues:
$310
(Based on a 30 year fixed loan at 3.75% with $15,000 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 793sq ft $95 / sq ft CND
Lot Size19.0acre Built1970 On Site19days
Nicely FURNISHED, or unfurnished if buyer desires, 1 Bedroom, 1 bath, upstairs unit overlooking the pool. Light & bright with open kitchen, breakfast bar & breakfast nook,... more
Nicely FURNISHED, or unfurnished if buyer desires, 1 Bedroom, 1 bath, upstairs unit overlooking the pool. Light & bright with open kitchen, breakfast bar & breakfast nook, updated appliances, large walk-in closet and Screened Patio. Immediate occupancy! Walk to Wholefoods, shopping, restaurants and banks. (desk in bedroom does not convey). less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$394,200
$1,460/mo
Monthly Payment:
$1,460
Principal & Interest:
$1,460
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $78,840 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
2bed 2bath 1,487sq ft $265 / sq ft SFR
Lot Size30,729sq ft Built1951 On Site19days
Awesome opportunity for this lakefront home on lake killarney with your own boat house. This is located close to everything, fine dining and shopping and convenient to major... more
Awesome opportunity for this lakefront home on lake killarney with your own boat house. This is located close to everything, fine dining and shopping and convenient to major roadways. Call your agent today!!! less
Listing Provided Courtesy of Real Estate Professionals Se
Popularity
$1,150,000
$4,260/mo
Monthly Payment:
$4,260
Principal & Interest:
$4,260
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $230,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,572sq ft $322 / sq ft SFR
Lot Size9,651sq ft Built2014 On Site20days
Exquisite custom built home in Winter Park. This two-story floor plan offers a very versatile floor plan with an oversized master suite and spacious secondary bedrooms each with... more
Exquisite custom built home in Winter Park. This two-story floor plan offers a very versatile floor plan with an oversized master suite and spacious secondary bedrooms each with private bathrooms and walk-in closets. The master bedroom features coffered ceilings, electric fireplace, and built-in book case. Master bath includes Jacuzzi tub, dual sinks, and walk-in shower with luxury spa shower heads. The beautiful gourmet kitchen is well appointed with custom wood cabinetry, granite counter tops, large walk-in pantry, and GE Café Series appliances with five burner propane cook top and convection oven. Enjoy peaceful evenings in your very own wine room with custom cabinetry, built-in sink, and wine refrigerator. You will enjoy entertaining in the serene outdoor living space which includes a saltwater pool and spa with solar and propane heating, brick paver pool deck, outdoor shower and spacious patio with electric fireplace. Energy efficient features throughout the home. If you are looking for a luxurious new construction home in Winter Park, look no further than this one of a kind home. Taxes are an estimate for 2015, 2014 taxes were not for the current new home. less
Listing Provided Courtesy of Re/max Platinum Realty
Popularity
$788,000
$2,919/mo
Monthly Payment:
$2,919
Principal & Interest:
$2,919
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $157,600 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 2,442sq ft $323 / sq ft SFR
Lot Size7,380sq ft Built1925 On Site20days
This home is a must see! Timeless Winter Park landmark with a new custom built addition that enhances all of the existing architectural elegance. Completion scheduled for late... more
This home is a must see! Timeless Winter Park landmark with a new custom built addition that enhances all of the existing architectural elegance. Completion scheduled for late July. This perfect Mission style home is located on a highly desirable street less than one block from Park Avenue and quick driving distance to the new Whole Foods Market and Winter Park Village. Come see the charm that every nook has in this beautiful home. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$429,900
$1,592/mo
Monthly Payment:
$1,592
Principal & Interest:
$1,592
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,980 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 2,253sq ft $191 / sq ft SFR
Lot Size10,615sq ft Built1960 On Site20days
WOW! Here’s a fantastic opportunity to own a beautiful home in the heart of Winter Park. Spectacularly renovated from top to bottom with custom designer touches, this... more
WOW! Here’s a fantastic opportunity to own a beautiful home in the heart of Winter Park. Spectacularly renovated from top to bottom with custom designer touches, this home is marvelous! The professionally restored terrazzo floors provide a sleek low maintenance surface while retaining the mid-century charm of the home. The open kitchen features custom all-wood cabinets with full extension/soft close drawer hardware; gorgeous Marble countertops with a large combination prep island and bar area, brand new stainless steel appliances, and modern hard wearing bamboo flooring. All bathrooms have been completely updated with new vanities, tops, faucets, hardware, and a custom glass enclosure in the master bedroom. The multi-split floorplan with abundant windows and sliders throughout make the home bright and airy yet the design provides ample privacy both inside the home and out. The HVAC system is brand new with insulated ductwork and the brand new windows feature double pane, insulated, low-e glass which will keep your energy bills low. The home has been completely re-plumbed and includes a new irrigation system, and all new landscape. This was truly a COMPLETE rehab, not just cosmetic. Not to mention the home is just a short walk to Baldwin Park's restaurants and shops and the Lake Baldwin Recreational Park across the street features an upscale playground, boat launch, and dog park. This home is luxury living at its finest. Setup your Viewing Today! less
Listing Provided Courtesy of Bateman Management Group Llc
Popularity
$229,900
$851/mo
Monthly Payment:
$851
Principal & Interest:
$851
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,579sq ft $146 / sq ft SFR
Lot Size8,135sq ft Built1962 On Site21days
Delightful 3 bedroom 2 bath in Winter Park with gardener's touch!! Charming curb appeal with beautiful landscaping and window boxes. Brand new AC, Fresh paint, new doors, and... more
Delightful 3 bedroom 2 bath in Winter Park with gardener's touch!! Charming curb appeal with beautiful landscaping and window boxes. Brand new AC, Fresh paint, new doors, and great floor plan. Terrazzo flooring throughout this Winter Park home. Kitchen features include tons of cabinets, beveled edge formica counters, large breakfast nook, and new slider doors that access the lush backyard. Bathrooms have been updated with new sinks and toilets. Large living room and separate dining room give multiple options for entertaining a crowd. Enjoy the privacy of the fenced backyard. This location has it all: close to Park Ave, YMCA, Cady Way Park, Shopping and Trails!! Paradise in Winter Park! less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$429,900
$1,678/mo
Monthly Payment:
$1,678
Principal & Interest:
$1,592
HOA Dues:
$86
(Based on a 30 year fixed loan at 3.75% with $85,980 down)
Winter Park, FL 32792
5bed 3bath 2,564sq ft $168 / sq ft SFR
Lot Size7,500sq ft Built2014 On Site21days
Located close to Downtown Winter Park, 417, shopping, & restaurants, this area has it all. Over $40,000 in upgrades throughout, pool with spa, fenced yard, & lot is on the only... more
Located close to Downtown Winter Park, 417, shopping, & restaurants, this area has it all. Over $40,000 in upgrades throughout, pool with spa, fenced yard, & lot is on the only Cul de sac in the community. Oil rubbed bronze handles and fixtures throughout. Recessed lightning throughout home including rear patio. Home is pre-wired for Ethernet, 5 Klipsch speaker surround sound in Bonus room and rear Klipsch ceiling speakers in Family room downstairs. Recessed lighting throughout the home. In-floor power outlet in Family room. Bonus room is pre-wired for home theater (5.1) & has a custom riser built for theater style seating (can be removed). Hardwood floors in downstairs bedroom as well as dining room. 38 x 10 Covered Patio comes standard with recessed lighting, ceiling fans and is pre wired for speakers as well as cable and Ethernet. Home has gutters, ceiling fans in every room, faux wood blinds, overhead ceiling storage in garage. Garage features a dedicated 20amp/110v outlet for Refrigerator as well as rough in plumbing for a water softener. Kitchen has a full size custom pantry cabinet and custom backsplash with upgraded espresso cabinets and under cabinet lighting. GE Stainless Steel Appliances are upgraded to include a Range/Stove, Refrigerator, Dishwasher, and Microwave as well as Garbage disposal. Downstairs features a Nest Thermostat. (Patio Speakers do not convey) Epson Projector, Projection Screen, & Washer and Dryer can be negotiated less
Listing Provided Courtesy of The Sheridan Network.com
Popularity
$1,799,999
$6,668/mo
Monthly Payment:
$6,668
Principal & Interest:
$6,668
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $360,000 down)
Winter Park, FL 32792
Seminole County School District
5bed 6bath 6,001sq ft $300 / sq ft SFR
Lot Size39,528sq ft Built2012 On Site21days
New custom built home on Bear Gully Lake. Private gated entry onto a Pavered drive leads you to the stately two story entrance. Three cameras provide security. The magnificent... more
New custom built home on Bear Gully Lake. Private gated entry onto a Pavered drive leads you to the stately two story entrance. Three cameras provide security. The magnificent open plan provides views of Bear Gully Lake. Travertine or wood flooring is found throughout the home. Upgraded trim package with solid-core doors and crown moulding along with LED ceiling lightening, double-pane windows and custom draperies are found throughout the home. The kitchen is a Chef's dream with Wolf Appliances. The first floor features the Master Suite and a large Guest Suite. Custom ironwork graces the curved staircase leading to the 2nd floor. The large upstairs bedrooms offer privacy to other family members and have 4" Plantation shutters. Every room has a different coffered ceiling. Bedroom five, currently being used as an office, has a travertine floored balcony overlooking the beautiful pool and lake. The lake can be used with both motorized or non-motorized boats for a great play day on the lake. Skiing is allowed. The outdoor areas have accent lighting and a Cabana with an outdoor kitchen, bathroom and outside shower to make the days outside fun and the fireplace provides ambience at night. The lanai and all outdoor ceiling are made of Pecky Cypress. Three efficient AC systems and R19 spray foam insulation make the utility bills for this size home very low. Also: 250 gallon propane tank, 3 tankless H2O heaters. County water and Aqualear Aerobic Treament Septic System. less
Listing Provided Courtesy of Stirling Sotheby's Int'l Rlty
Popularity
$199,900
$743/mo
Monthly Payment:
$743
Principal & Interest:
$740
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $39,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 3bath 2,088sq ft $96 / sq ft SFR
Lot Size13,420sq ft Built1968 On Site22days
FOUR bedroom THREE bath split bedroom home with 2088 SQ FT offers plenty of room to roam!! AMAZING .31 acre lot features a sparkling, newly refinished pool PLUS additional... more
FOUR bedroom THREE bath split bedroom home with 2088 SQ FT offers plenty of room to roam!! AMAZING .31 acre lot features a sparkling, newly refinished pool PLUS additional backyard garden! Inside you will find formal living & dining rooms and spacious kitchen with breakfast bar overlooking family room. The 3 way bedroom split plan is perfect for a growing family OR an excellent plan for 1 Bedroom/1 Bath in-law or guest suite. Huge 13 x 8 inside utility room PLUS 15 x 8 workshop PLUS utility shed in back yard! Extras include gas appliances, wood & parquet floors & quiet corner lot on cul-de-sac street! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$349,900
$1,296/mo
Monthly Payment:
$1,296
Principal & Interest:
$1,296
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $69,980 down)
Winter Park, FL 32792
Baldwin Park Orange County School District
4bed 2bath 1,400sq ft $250 / sq ft SFR
Lot Size10,803sq ft Built1959 On Site22days
Location, location, location!!! This well maintained pool home is located in beautiful winter park, just minutes away from shopping, dining, and a+ rated schools. Easy access to... more
Location, location, location!!! This well maintained pool home is located in beautiful winter park, just minutes away from shopping, dining, and a+ rated schools. Easy access to baldwin park, downtown orlando, and major highways. Home as mother in law suite that can be used as a rental unit as well. 2 car attached garage with pool is a rare find in this area, come see this home today. less
Listing Provided Courtesy of Keller Williams Advantage 2
Popularity
2 3 4 5 6 7 8 9 10 ... 15 25
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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
Content provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Sunday, April 26, 2015 at 10:06 PM