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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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$329,900
$1,222/mo
Monthly Payment:
$1,222
Principal & Interest:
$1,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $65,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,525sq ft $216 / sq ft SFR
Lot Size6,651sq ft Built1925 On Site153days
Welcome to 2600 Winter Park Road. Built in 1925, this Spanish Mediterranean home can claim a designation in the Winter Park Register of Historic places. The original owner since... more
Welcome to 2600 Winter Park Road. Built in 1925, this Spanish Mediterranean home can claim a designation in the Winter Park Register of Historic places. The original owner since 1957 has lovingly cared for and maintained this 3 bedroom, 2 bath home. The entrance to the home is through a segmented arched opening on the front facing gable. The living room features a wood burning fireplace, a cathedral beamed ceiling, original windows and hardwood floors. From the dining room, French doors, open to a screened side porch. The updated kitchen features recessed lighting, granite counters, Kitchen Aid appliances, new hardwood floors and window treatments. One bathroom has a walk-in shower and the second bathroom has a tub/shower. A free standing two-car garage has been attached to the main body of the house by an open breezeway. The house has many unique architectural features and mature landscaping. Seller will transfer a one year home warranty. Walking distance to the new East End marketplace and Blue Jacket Park. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
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$695,000
$2,574/mo
Monthly Payment:
$2,574
Principal & Interest:
$2,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 6bath 5,184sq ft $134 / sq ft SFR
Lot Size29,185sq ft Built1968 On Site154days
Being already impressed with the exterior of this amazing home, you are going to be more than impressed with the interior as well! Beautiful hardwood, laminate and tile floors... more
Being already impressed with the exterior of this amazing home, you are going to be more than impressed with the interior as well! Beautiful hardwood, laminate and tile floors extend throughout this spacious home. The owner’s retreat and 2 secondary bedrooms are upstairs along with a guest bath with double sinks and a jacuzzi tub and shower. The master suite has an adjacent sitting room great for a nursery, dressing room, workout room, sewing room, library or media nook and an unparalleled view of Garden Lake. Downstairs is an additional bedroom with en-suite bathroom plus large kitchen, family room with fireplace, dining room and office/den/sitting room. Tucked to the rear of the property is a detached in-law suite with a kitchen, bath and bedroom and the upper portion of the oversized detached garage has a partially finished bonus room (currently being used for storage). The grounds are tastefully landscaped and the oversized screened pool has beautiful views of the lake as well. Enjoy your own piece of paradise right here in Winter Park! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$1,200,000
$5,195/mo
Monthly Payment:
$5,195
Principal & Interest:
$4,445
HOA Dues:
$750
(Based on a 30 year fixed loan at 3.75% with $240,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,579sq ft $335 / sq ft SFR
Lot Size3.3acre Built1915 On Site154days
This Pristine Victorian Home is condo living in a single family home. Private Gate Entry brings you into the Semi-Circular Driveway at The Vias. The HOA maintains the Entire... more
This Pristine Victorian Home is condo living in a single family home. Private Gate Entry brings you into the Semi-Circular Driveway at The Vias. The HOA maintains the Entire Exterior as well as the Lush Landscaped Grounds. As you enter you will notice the attention to detail in every corner. Home movie theater, Chef’s Kitchen with Gourmet Gas Stove, Two Fireplaces, Beautiful Hardwood Floors, Private Formal Dining Room fit for Royalty. Stunning Master Suite with Sitting Area and additional staircase leading to Large Bonus Room. Beautiful Views from the Balconies above. Relax on the Wraparound Porch as you take in the Magnificent Water View. Lake Maitland rental slip is only $750.00 per year for your boat. This is a one of a kind opportunity to own a piece of history while living the life some can only dream of. less
Listing Provided Courtesy of Real Estate Firm Of Orlando
Popularity
$374,900
$1,388/mo
Monthly Payment:
$1,388
Principal & Interest:
$1,388
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $74,980 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 2,315sq ft $162 / sq ft SFR
Lot Size12,761sq ft Built1965 On Site155days
Hurry & make offer before i go off market! This beautiful winter park home has had a price reduction! Located in a highly rated school district, this traditional home has great... more
Hurry & make offer before i go off market! This beautiful winter park home has had a price reduction! Located in a highly rated school district, this traditional home has great curb appeal and enormous potential. Inside you will find a great layout, split floor plan, large master suite, and a fourth bedroom (converted from the third garage bay) with large closets and private access. Exit through french doors to a beautiful paver patio and swimming pool or enjoy a front yard with plenty of free space and lush landscaping. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$350,000
$1,327/mo
Monthly Payment:
$1,327
Principal & Interest:
$1,296
HOA Dues:
$31
(Based on a 30 year fixed loan at 3.75% with $70,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 2,562sq ft $137 / sq ft SFR
Lot Size16,977sq ft Built1986 On Site155days
Large home in desirable Pelican Bay and Seminole School District. Split plans offers two bedrooms downstairs (master with on-suite and guest bedroom with full bath). Sunken... more
Large home in desirable Pelican Bay and Seminole School District. Split plans offers two bedrooms downstairs (master with on-suite and guest bedroom with full bath). Sunken living room with high vaulted ceilings. Tile throughout entire downstairs including inside laundry area. Upstairs are two more large bedrooms (another master with on-suite and guest bedroom) with hall bath. There is also a small bonus room that could be a study, craft room or play area. This large corner lot gives plenty of room to add a pool or enjoy the yard from the outside deck. Two car garage with plenty of off-street parking. Room to park your boat or RV. Public utilities. The community offers a beautiful park like setting with a basketball court, picnic area and a fishing pier on Lake Florence. There is a launch (riprap) for small boats and canoes. Lake Florence is a ski lake. less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$700,000
$2,593/mo
Monthly Payment:
$2,593
Principal & Interest:
$2,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $140,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,334sq ft $300 / sq ft SFR
Lot Size12,046sq ft Built1960 On Site155days
This immaculate & completely updated three bedroom plus office single story home is situated on a quiet street in the sought after “Vias” of Old Winter Park. Floor... more
This immaculate & completely updated three bedroom plus office single story home is situated on a quiet street in the sought after “Vias” of Old Winter Park. Floor plan is open with views of the private back yard & sparking pool with brick paver patio. Spacious kitchen has custom cabinets, granite counter tops, pantry & opens to a light & bright family room. Large dining & living are perfect for family enjoyment or entertaining. Garage is attached & has plenty of additional storage space. Additional amenities include: French doors, custom closets throughout, hard wood & tile floors, custom wood shutters, laundry room with plenty of storage, tile roof & landscape lighting. Updates include: electrical, plumbing, new AC, new pool heater and garage floor coating. This home is move in ready. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$154,900
$573/mo
Monthly Payment:
$573
Principal & Interest:
$573
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $30,980 down)
Winter Park, FL 32792
Goldenrod
3bed 2bath 1,412sq ft $110 / sq ft SFR
Lot Size8,443sq ft Built1959 On Site158days
Located in the Eastbrook subdivision, this 3 bedroom, 2 bath Winter Park home features split bedroom plan, carpeted floors in living room and dining area, tile throughout the... more
Located in the Eastbrook subdivision, this 3 bedroom, 2 bath Winter Park home features split bedroom plan, carpeted floors in living room and dining area, tile throughout the rest of the home, vaulted ceilings,updated kitchen cabinets. Washer/Dryer included! 2 car garage, fenced yard with screened in wooden gazebo and deck are great for entertaining. less
Listing Provided Courtesy of Waterstone Realty
Popularity
$929,900
$3,445/mo
Monthly Payment:
$3,445
Principal & Interest:
$3,445
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $185,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,527sq ft $264 / sq ft SFR
Lot Size21,025sq ft Built1948 On Site159days
Ideal location in old winter park! One mile to exclusive park ave, upscale shopping and gourmet restaurants centered around a chain of lakes, parks, golf courses and country... more
Ideal location in old winter park! One mile to exclusive park ave, upscale shopping and gourmet restaurants centered around a chain of lakes, parks, golf courses and country clubs. Walk to the best schools! 10 minutes to downtown orlando, without traffic or highways! Enchanting forrest hills neighborhood-2 beautiful lakes (lake sue & lake chelton), tree lined, brick paved streets with rolling hills and amazing sunsets on lake sue! This beautifully designed home was completely renovated in1997-new electrical, plumbing and roof with additions by winter park architect mark nasrallah. This home has 4 bedrooms and 2.5 baths with a split bedroom plan. A large master suite with granite fireplace, jacuzzi tub overlooking the pool, double shower and large closets. Living room has a fireplace, the family room has 10 ft ceilings and a built-in entertainment center with french doors to covered porch and pool. A chef's eat-in kitchen has decor double ovens, a thermador 6 burner gas cooktop, built-in refrigerator, custom designed maple cabinets with granite counter tops. A formal dining room-10 ft ceilings, a built in china cabinet and french doors leading to a covered porch/pool. The home offers great outdoor patios and a covered porch overlooking the swimming pool. The home is situated on a professionally landscaped, fenced double lot and has a partial lake view, located on a quite street! Want a great lake view? Add a second floor to this property! Lots of room to grow! Will consider lease purchase. less
Listing Provided Courtesy of Addvantage Real Estate Services
Popularity
$55,000
$341/mo
Monthly Payment:
$341
Principal & Interest:
$203
HOA Dues:
$138
(Based on a 30 year fixed loan at 3.75% with $11,000 down)
Winter Park, FL 32792
1bed 1bath 786sq ft $70 / sq ft CND
Lot Size10.1acre Built1974 On Site160days
1/1 Condo near UCF and Full Sail. Great shopping and restaurants near by! Great for an investment property. Spacious interior. Balcony for entertaining. Pool in community.... more
1/1 Condo near UCF and Full Sail. Great shopping and restaurants near by! Great for an investment property. Spacious interior. Balcony for entertaining. Pool in community. Minutes from downtown. Don't miss this opportunity! less
Listing Provided Courtesy of Brennan Real Estate Group Llc
Popularity
$329,000
$1,218/mo
Monthly Payment:
$1,218
Principal & Interest:
$1,218
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $65,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,393sq ft $236 / sq ft SFR
Lot Size6,847sq ft Built1952 On Site160days
Charming bungalow on the brick "tree streets" of Winter Park! Oversized Master Bedroom overlooking a large fenced in backyard with storage shed. Enjoy both a living room and... more
Charming bungalow on the brick "tree streets" of Winter Park! Oversized Master Bedroom overlooking a large fenced in backyard with storage shed. Enjoy both a living room and great room with a cozy fireplace (garage conversion). Make this your new home or design your dream home in this area of new construction homes! less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$1,599,000
$5,924/mo
Monthly Payment:
$5,924
Principal & Interest:
$5,924
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $319,800 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 5,364sq ft $298 / sq ft SFR
Lot Size6,637sq ft Built1984 On Site162days
Fabulous modern Mediterranean with sleek/contemporary interiors, unparalleled location & private setting surrounded by Mead Gardens, wildlife & bird sanctuary...This home is... more
Fabulous modern Mediterranean with sleek/contemporary interiors, unparalleled location & private setting surrounded by Mead Gardens, wildlife & bird sanctuary...This home is walking distance to downtown Winter Park/Park Avenue, Rollins College & Azalea Lane tennis courts & park! ... Enjoy tranquil views of nature from any one of 4 covered porches around the home... The main level living areas are all very bright with wonderful tall windows/doors & open with plenty of room for entertaining a large party along with plenty of expansive wall space for displaying an art collection… There is a gorgeous gourmet island kitchen open to apprx. 2,000 SF of living, dining, bar and other generous gathering space… The heated endless pool/spa is also on the main level and offers ColorLogic (LED technology) lighting for a reflective background to light up your art & walls in the evenings… There is a wonderful spacious master retreat with its own private balcony overlooking tree-top park views… Along with 2 other large in-suite bedrooms, the 4th bedroom is set up as an in-law quarters (or guest apartment) with its own separate kitchen… Quality Andersen windows/doors and thermal insulation along with solid concrete construction make this home energy efficient… full security system & Bose audio system. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$274,500
$1,017/mo
Monthly Payment:
$1,017
Principal & Interest:
$1,017
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $54,900 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,250sq ft $220 / sq ft SFR
Lot Size7,081sq ft Built1927 On Site162days
Come and see this cozy home located in the heart of Winter Park. Close to shopping, restaurants, and major roadways, this home is a gem! The list of improvements in this home... more
Come and see this cozy home located in the heart of Winter Park. Close to shopping, restaurants, and major roadways, this home is a gem! The list of improvements in this home goes on and on! Pride of ownership is unbelievable with over $150,000 in improvements! Roof is only 6 years old, new air and heat pump installed 3 yrs ago, all new installation in the attic 3 yrs ago, water main replaced 6 yrs ago, new irrigation system, decorative brick work on front and sides of house, new water heater 6 yrs ago, and brand new 8x8 storage shed in backyard! Beautiful, all natural oak wood floors throughout the home provides a rich look and feel! Brand new moldings, ceramic tile and paint! Lovely Florida room great for enjoying a morning cup of coffee! Enjoy open living and dining concept great for entertaining! Living room features a custom fireplace solid oak mantel with black granite hearth. The kitchen has all new stainless steel appliances, solid granite counter tops, and all new wood cabinets! Both bathrooms in the home have been completely remodeled for a modern feel! New ceiling fans and lights throughout home. Carport has been converted to full insulated garage that can fit 2 cars! You must see this home to appreciate the details and beauty of it all! All information recorded in the MLS is intended to be accurate however, it should be independently verified less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$435,000
$1,611/mo
Monthly Payment:
$1,611
Principal & Interest:
$1,611
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $87,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,302sq ft $189 / sq ft TWN
Lot Size8,597sq ft Built2008 On Site165days
Open & Bright Townhome with no HOA or Dues. This unique Tri-level boast High ceilings, real Wood floors, 3 full baths plus a separate family room with balcony. One bedroom and... more
Open & Bright Townhome with no HOA or Dues. This unique Tri-level boast High ceilings, real Wood floors, 3 full baths plus a separate family room with balcony. One bedroom and bath on the first level. Master has dual sinks plus oversized shower and walk-in closet. Beautifully landscaped with paver and covered porch entry. All centrally located in Lawndale/Orwin Manor North close to I-4, 17-92, Downtown Winter park and Rollins College. Brand new St. Augustine sod and 4 ft black aluminum fence purchased and to be installed by September. less
Listing Provided Courtesy of Real Estate Firm Of Orlando
Popularity
$42,000
$287/mo
Monthly Payment:
$287
Principal & Interest:
$155
HOA Dues:
$132
(Based on a 30 year fixed loan at 3.75% with $8,400 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 537sq ft $78 / sq ft CND
Lot Size10.1acre Built1974 On Site166days
Studio style condo located in Winter Park, with convienient access to shopping and public transport. Ground floor with patio and tile flooring throughout. Great investment... more
Studio style condo located in Winter Park, with convienient access to shopping and public transport. Ground floor with patio and tile flooring throughout. Great investment property. less
Listing Provided Courtesy of Brennan Real Estate Group Llc
Popularity
$43,000
$297/mo
Monthly Payment:
$297
Principal & Interest:
$159
HOA Dues:
$138
(Based on a 30 year fixed loan at 3.75% with $8,600 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 549sq ft $78 / sq ft CND
Lot Size10.1acre Built1974 On Site166days
1/1 Condo on second floor with convenient access to shopping, public transport and great schools. Cozy balcony with courtyard view. Close parking, pet friendly.
1/1 Condo on second floor with convenient access to shopping, public transport and great schools. Cozy balcony with courtyard view. Close parking, pet friendly. less
Listing Provided Courtesy of Brennan Real Estate Group 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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The information being provided by Mid-Florida Regional Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid-Florida Regional Multiple Listing Service. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid-Florida Regional Multiple Listing Service. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

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Data last updated: Monday, August 31, 2015 at 2:13 PM. Properties in listings may have been sold or may no longer be available.