Cheap Townhouses for Sale in Winter Park, FL

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ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Aloma Trails is a gated townhome community, built by Ryan Homes, located in Winter Park. Conveniently you'll find it's location between UCF and Rollins College. Seminole County is known for its highly rated public schools. Only minutes from Park Avenue shopping and restaurants. This END UNIT townhome features 3 bedrooms, 2 1/2 bathrooms, and a TWO car garage. Granite countertops, 42” upper cabinets, GE appliance package including the microwave, oven, dishwasher, and smooth stop range. The living room is very large and wide open to the kitchen and dining. Collapsible 3 panel sliding glass doors allow easy access to back patio. The primary bedroom features 2 walk-in closets, raised dual

$380,000

3 beds2.5 baths1,787 sq ft

7506 Aloma Pines Ct, Winter Park, FL 32792

$396 HOA • 2 garage spots • Built 2017

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Experience the best value in Winter Park. Beautifully maintained corner-unit townhome in the desirable Four Seasons community, offering a perfect blend of comfort, privacy and style. This bright and inviting residence features modern laminated floors, new carpet in the bedroom areas, granite kitchen countertops, updated lighting, and recently painted interiors. Enjoy the convenience of a private front entrance and a second entrance from the spacious patio- ideal for added flexibility and seamless indoor=outdoor living. Abundant natural light enhances the the open layout and inviting living areas. Four Seasons community delivers top tear amenities: 3 swimming pools, tennis courts, a fitness

$237,000

2 beds1.5 baths1,085 sq ft

200 Saint Andrews #3001, Winter Park, FL 32792

$440 HOA • Garage • Community pool

(305) 209-4715

3D WALKTHROUGH

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
* * This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment. * * Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout with high ceilings, modern finishes, and tile and carpet flooring all throughout. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating a seamless environment for entertaining or everyday living. All three bedrooms include generous walk-in closets,

$450,000

3 beds3 baths2,308 sq ft

2224 Shadowland Loop, Winter Park, FL 32792

$320 HOA • 2 garage spots • Community pool

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Gorgeous 2-Story Townhome, newly built in 2024. Located in upscale Winter Park, Florida, close to fine dining, shopping and entertainment. Not far from downtown Orlando and Orlando theme parks, this manicured gated community showcases beautiful landscaping and a sparkling pool surrounded by coveted modern architecture. The home contains the high-end Lux Fresh interior package, and owner has added light dimmers, ceiling fans, window coverings and a kitchen island. In addition to seating capacity at the expansive, stone kitchen counter, new stainless-steel appliances complete this large chef’s kitchen. The stunning open-concept living area on the first level is great for entertaining or

$436,900

3 beds2.5 baths1,916 sq ft

2808 Bright Bird Ln, Winter Park, FL 32792

$375 HOA • Garage • Pool

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
This 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space in a highly sought-after location. Enjoy a bright living area featuring a gorgeous tiled fireplace, built-in bookshelves, and two sets of French doors that open to your private patio and fenced backyard with brick pavers and turf grass. The home includes a spacious double vanity bathroom, custom shelving for extra storage, and a one-car garage with an additional air-conditioned room behind it. Recent updates include a 2021 roof, 2022 AC, and a transferable termite bond for added peace of mind. Located just 1.5 miles from Downtown Winter Park and Park Avenue, and only a mile from the newly renovated Wi

$372,500

2 beds2 baths1,495 sq ft

1229 Park Green Pl, Winter Park, FL 32789

$327 HOA • Community pool • Built 1984

Property at 7580 Aloma Pines Ct, Winter Park, FL 32792, 3 beds, 3.5 baths

$359,500

3 beds3.5 baths1,872 sq ft

7580 Aloma Pines Ct, Winter Park, FL 32792

Property at 7480 Woodburn Ct #39, Winter Park, FL 32792, 3 beds, 2.5 baths

$199,999

3 beds2.5 baths1,151 sq ft

7480 Woodburn Ct #39, Winter Park, FL 32792

Property at 1900 Erudite Way, Winter Park, FL 32792, 3 beds, 2.5 baths

$439,000

3 beds2.5 baths1,907 sq ft

1900 Erudite Way, Winter Park, FL 32792

Property at 3370 Cedar Springs Pl #156, Winter Park, FL 32792, 2 beds, 2.5 baths

$197,500

2 beds2.5 baths1,031 sq ft

3370 Cedar Springs Pl #156, Winter Park, FL 32792

Property at 2417 Passamonte Dr Unit 1E, Winter Park, FL 32792, 3 beds, 2.5 baths

$329,999

3 beds2.5 baths1,837 sq ft

2417 Passamonte Dr Unit 1E, Winter Park, FL 32792

Property at 3254 Oak Lake Pl #137, Winter Park, FL 32792, 2 beds, 2.5 baths

$214,900

2 beds2.5 baths1,031 sq ft

3254 Oak Lake Pl #137, Winter Park, FL 32792

Property at 7444 Woodburn Ct #29, Winter Park, FL 32792, 2 beds, 2.5 baths

$177,000

2 beds2.5 baths1,031 sq ft

7444 Woodburn Ct #29, Winter Park, FL 32792

Property at 1447 Broad Wing Ln, Winter Park, FL 32792, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths2,308 sq ft

1447 Broad Wing Ln, Winter Park, FL 32792

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ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Investor Opportunity or Home Buyer! Income-producing 3BR/1.5BA townhouse in Casselberry with an in-place tenant paying $1,950/month who would like to remain. Features include tile flooring on the first floor, upgraded bath, full-size W/ D, ceiling fans throughout, and a large private fenced courtyard—low maintenance and highly desirable for renters. Community amenities include Lake Howell access, pool, clubhouse, 24-hr security, and assigned parking. Prime location near Full Sail, UCF, Rollins, shopping, dining, and transit. Immediate cash flow—schedule your showing today!

$239,900

3 beds1.5 baths1,344 sq ft

520 Georgetown Dr, Casselberry, FL 32707

$500 HOA • 54 parking spots • Community pool

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Lake of the Woods 2 bedroom 2 bath townhome with 1 car enclosed garage. Private courtyard in front. Foyer with coat closet. Large Kitchen with newer appliances and eat in space. Spacious great room and formal dining room that is nice and bright. Big owners bedroom with walk-in closet, makeup vanity and new shower. Second bedroom has walk-in closet. Inside laundry closet with newer washer and dryer. Newer windows. Replumbed. New roof 2025. Newer sliding door. Hot water heater 2022. Low HOA dues. Community features POOL, tennis and basketball courts, fitness center, playground, picnic pavilion, community library, and fishing pier! Good schools. Great location. Move right in!

$279,000

2 beds2 baths1,296 sq ft

608 Woodridge Dr, Fern Park, FL 32730

$260 HOA • Garage • Community pool

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Discover comfortable Winter Park living in this bright and stylish 3-bedroom, 2.5-bathroom corner-unit townhome located in the gated Grayson Square community. Abundant natural light fills the open-concept living area, which flows seamlessly to a covered lanai that’s perfect for relaxing mornings or quiet evenings. The modern kitchen includes stainless steel appliances, quartz countertops, and generous storage, offering both convenience and contemporary appeal. The owner’s suite features a spacious walk-in closet and an elegant ensuite bathroom with a glass-door shower and dual quartz vanities. Additional highlights include a two-car garage with epoxy flooring, and a washer and d

$449,900

3 beds2.5 baths1,782 sq ft

1951 Canny Cv, Winter Park, FL 32792

$375 HOA • 2 garage spots • Community pool

3D WALKTHROUGH

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
One or more photo(s) has been virtually staged. Welcome to 982 Congress Court, a charming 2-bedroom townhome featuring two en-suite bathrooms upstairs and a convenient half bath downstairs for added comfort and functionality. This home offers a solid foundation with a brand new hot water heater (2025) and a roof replaced in 2018, giving you peace of mind as you add your personal touches. While it could use a bit of TLC, it holds great potential—whether you’re a first-time homebuyer looking to make a place your own or an investor seeking a promising opportunity. The main living and dining areas provide a welcoming flow, and the location offers easy access to a variety of nearby s

$245,000

2 beds2.5 baths1,350 sq ft

982 Congress Ct, Casselberry, FL 32707

$141 HOA • Community pool • Built 1987

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Welcome Home to this beautifully maitained 2- bedroom, 2 bath with a BONUS ROOM Villa. This unit's blends updated finishes with the convinience of low association fees and established neighborhood amenities- that include a well maintaned POOL AND GROUNDS. all just minutes from MCO(Orlando Airport) MAYOR highways (408,528) malls, and dinning. This charming home features a modern kitchen with updated finishes (stainlees steel apliances, a large sink, )The kitchen offers ample cabinetry and counter space, along with the WASHER AND DRYER, stay with the unit for added conveninience direct access to a screened -in patio for relaxing or entretaining. Enjoy a peace of mind of a new INSULATED ROOF 2

$279,900

2 beds2 baths965 sq ft

667 Golden Sunshine Cir, Orlando, FL 32807

$69 HOA • Community pool • Built 1986

OPEN JAN 10 TO 2PM

ABOUT THIS HOME
Cheap Townhouses for Sale in Winter Park, FL
Enjoy peace of mind with a brand-new roof, plus newer electrical and plumbing, easing all your worries from day one. The community has a roof assessment BUT THIS OWNER PAID THIS UNITS ASSESSMENT IN FULL ALREADY FOR YOU! Move in with NO worries! Discover comfort and convenience in this beautifully maintained 2-bedroom, 2.5-bath townhome offering 1,564 sq. ft. of thoughtfully designed living space including a bonus room downstairs that is perfect for an at home office, craft studio or work out space. Both bedrooms are located upstairs & have bathrooms attached making them BOTH primary suites with walk in closets, perfect for roommate situations! Fresh interior and exterior paint make th

$319,999

2 beds2.5 baths1,564 sq ft

136 Teriwood Ct, Fern Park, FL 32730

$260 HOA • 2 garage spots • Community pool

Property at 2833 Shady Willow Ln, Oviedo, FL 32765, 3 beds, 2.5 baths

$350,000

3 beds2.5 baths1,502 sq ft

2833 Shady Willow Ln, Oviedo, FL 32765

Property at 4701 New Orleans Cv, Oviedo, FL 32765, 4 beds, 3 baths

$440,000

4 beds3 baths1,769 sq ft

4701 New Orleans Cv, Oviedo, FL 32765

Property at 2853 Cliffe Ct, Oviedo, FL 32765, 3 beds, 2.5 baths

$345,000

3 beds2.5 baths1,872 sq ft

2853 Cliffe Ct, Oviedo, FL 32765

Property at 471 Meadowood Blvd, Fern Park, FL 32730, 2 beds, 2 baths

$325,000

2 beds2 baths1,296 sq ft

471 Meadowood Blvd, Fern Park, FL 32730

Property at 2516 Olive Branch Way, Orlando, FL 32817, 2 beds, 2 baths

$274,900

2 beds2 baths1,093 sq ft

2516 Olive Branch Way, Orlando, FL 32817

Property at 650 Woodridge Dr #650, Fern Park, FL 32730, 3 beds, 2 baths

$329,000

3 beds2 baths1,721 sq ft

650 Woodridge Dr #650, Fern Park, FL 32730

Property at 1110 Woodbine St, Fern Park, FL 32730, 3 beds, 2 baths

$319,000

3 beds2 baths1,541 sq ft

1110 Woodbine St, Fern Park, FL 32730

Property at 1529 N Carolwood Blvd, Fern Park, FL 32730, 3 beds, 2 baths

$329,000

3 beds2 baths1,721 sq ft

1529 N Carolwood Blvd, Fern Park, FL 32730

Property at 2040 Countryside Cir N, Orlando, FL 32804, 2 beds, 2 baths

$345,000

2 beds2 baths1,560 sq ft

2040 Countryside Cir N, Orlando, FL 32804

Property at 806 Town Cir #156, Maitland, FL 32751, 3 beds, 3 baths

$267,000

3 beds3 baths1,575 sq ft

806 Town Cir #156, Maitland, FL 32751

Property at 739 Golden Sunshine Cir, Orlando, FL 32807, 3 beds, 2 baths

$320,000

3 beds2 baths1,312 sq ft

739 Golden Sunshine Cir, Orlando, FL 32807

Property at 2401 Antilles Dr, Winter Park, FL 32792, 3 beds, 2 baths

$325,000

3 beds2 baths1,719 sq ft

2401 Antilles Dr, Winter Park, FL 32792

Property at 5045 Cypress Branch Pt, Oviedo, FL 32765, 3 beds, 2.5 baths

$390,000

3 beds2.5 baths1,656 sq ft

5045 Cypress Branch Pt, Oviedo, FL 32765

Property at 623 Red Oak Cir #109, Altamonte Springs, FL 32701, 3 beds, 2.5 baths

$369,900

3 beds2.5 baths1,914 sq ft

623 Red Oak Cir #109, Altamonte Springs, FL 32701

Based on information submitted to the MLS GRID as of Mon Dec 22 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Cheap Townhouses for Sale in Winter Park

There are currently 13 cheap townhouses for sale in Winter Park at a median listing price of $630K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Park stay on the market for 61 days. Popular neighborhoods include Audubon Park, College Park, Winter Park Pines, Baldwin Park, and Downtown Maitland. This map is refreshed with the newest listings in Winter Park every 15 minutes.

In the past month, 37 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 61 condos, 16 townhouses, and 1 multi-family unit for sale in Winter Park last month. Winter Park is a minimally walkable city in Orange County with a Walk Score of 44. Winter Park is home to approximately 27,958 people and 25,253 jobs. Find your dream home in Winter Park using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park. Our Winter Park real estate stats and trends will give you more information about home buying and selling trends in Winter Park. If you're looking to sell your home in the Winter Park area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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