Homes for sale under $500k in Middletown, VA

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OPEN SAT, 12PM TO 4PM

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. You'll love the professionally curated finishes! Situated on a corner lot and backing to open common area.

$484,999

3 beds2 baths1,610 sq ft

100 Midsummer Ln, Middletown, VA 22645

Elegant dining room • Private bath • Single-floor living

(877) 366-2213

OPEN SAT, 12PM TO 4PM

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
The main floor of this Coral home offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This home is built a loft. To round out this home a basement is included and this beautiful home backs to common area.

$469,999

3 beds2.5 baths1,840 sq ft

102 Midsummer Ln, Middletown, VA 22645

Convenient laundry • Backs to common area • Walk-in closet

(877) 366-2213

OPEN SAT, 12PM TO 4PM

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Enjoy single level living in this ranch plan Three bedrooms and 2 full baths. The Master Suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future bathroom. This beautiful home is a must see! Call today to schedule your tour of our Onyx ranch style plan.

$464,999

3 beds2 baths1,610 sq ft

104 Midsummer Ln, Middletown, VA 22645

Large kitchen island • Private bath • Single level living

(877) 366-2213

READY TO BUILD

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Enjoy single-floor living in this inspired ranch floor plan! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. A tech center provides added convenience! The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. A covered patio for outdoor entertaining is included on select homesites. You'll love the professionally curated finishes!

$464,999

3 beds2 baths1,610 sq ft

Onyx Plan, Middletown, VA 22645

Tech center • Elegant dining room • Ranch floor plan

Listing provided by Zillow

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Welcome to your new home in the charming town of Middletown, VA! This spacious 4-bedroom, 2.5-bath single-family home offers the perfect blend of comfort, style, and convenience. Enjoy an open floor plan that’s ideal for both everyday living and entertaining, featuring a large kitchen island and plenty of room to gather. The generously sized bedrooms provide comfort and flexibility, while the large, useable backyard offers an inviting space for outdoor relaxation or play. Conveniently located near major commuter routes—including I-81, Route 11, I-66, Route 7, and Route 50—this home makes commuting simple and efficient. You’ll also be just minutes from Winchester and

$460,000

4 beds2.5 baths2,880 sq ft

129 Birmingham, Middletown, VA 22645

Large kitchen island • Open floor plan • Useable backyard

(540) 773-8475

Property at 163 Emmet St, Middletown, VA 22645, 4 beds, 2.5 baths

$446,000

4 beds2.5 baths1,930 sq ft

163 Emmet St, Middletown, VA 22645

(540) 662-3484

Property at 6731 Middle Rd, Middletown, VA 22645, 3 beds, 2 baths

$435,000

3 beds2 baths2,630 sq ft

6731 Middle Rd, Middletown, VA 22645

(540) 665-0360

Property at Coral Plan, Middletown, VA 22645, 3 beds, 2.5 baths

$428,990

3 beds2.5 baths1,840 sq ft

Coral Plan, Middletown, VA 22645

Listing provided by Zillow

Property at 2425 Third St, Middletown, VA 22645, 4 beds, 2 baths

$350,000

4 beds2 baths1,484 sq ft

2425 Third St, Middletown, VA 22645

(540) 662-4500

Property at 119 Kensington Cir, Middletown, VA 22645, 3 beds, 2.5 baths

$334,000

3 beds2.5 baths1,307 sq ft

119 Kensington Cir, Middletown, VA 22645

(540) 665-0360

Property at 131 Kensington Cir, Middletown, VA 22645, 3 beds, 2.5 baths

$329,900

3 beds2.5 baths1,220 sq ft

131 Kensington Cir, Middletown, VA 22645

(540) 348-4911

Property at 2085 Chapel Rd, Middletown, VA 22645, 2 beds, 1.5 baths

$199,900

2 beds1.5 baths1,053 sq ft

2085 Chapel Rd, Middletown, VA 22645

(540) 227-4416

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VIDEO TOUR

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Be sure to go to the video button for a tour! This property offers the perfect blend of privacy, functionality and potential. Several high dollar updates were just completed this year. See list below. Beautifully positioned on approximately 2.94 acres and approximately 2,200 Sq Ft of finished living area. This inviting residence features 4 bedrooms and 2.5 baths, with two additional bonus rooms upstairs ideal for a home office, playroom, or guest space. The finished basement has its own private entrance which offers a wet bar area, laundry room, full bath, and your fourth bedroom with a walk in closet—making it a perfect in-law suite Rental opportunity or private retreat. Enjoy th

$500,000

4 beds2 baths2,088 sq ft

1064 Strasburg Rd, Front Royal, VA 22630

Wet bar area • Two laundry areas • Large yard

(540) 635-4900

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Charming and well-maintained home in a quiet Stephens City neighborhood! This property offers an inviting open-concept main level with abundant natural light, a comfortable kitchen with quality finishes, and spacious bedrooms upstairs for privacy and convenience. Enjoy a manageable yard perfect for relaxing or play, plus easy access to shopping, dining, commuter routes, and nearby Sherando Park. A great opportunity for anyone seeking comfort, convenience, and small-town charm in the Shenandoah Valley.

$499,999

3 beds3.5 baths2,559 sq ft

433 Town Run Ln, Stephens City, VA 22655

Nearby sherando park • Manageable yard • Comfortable kitchen

(540) 692-9378

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Discover the perfect blend of comfort and style in the Laurel. Valley Views sought after main level living floorplan. This thoughtfully designed home features 4 bedrooms and 3 bathrooms, all set within an open floorplan that's perfect for entertaining. Enjoy the convenience of a spacious basement with finished rec room, full bath and bedroom and plenty of additional storage space. The backyard has gorgeous views, creating serene retreat for relaxing or hosting gatherings. The kitchen is a chef's dream, complete with granite countertops, stainless steel appliances and LVP flooring. Home comes complete with washer/dryer, blinds on finished windows and smart home system. Ready to Move-in! * P

$499,990

4 beds3 baths2,638 sq ft

125 Woodford Dr, Stephens City, VA 22655

Finished rec room • Main level living • Lvp flooring

(804) 510-9139

OPEN SAT, 1PM TO 4PM

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
133 Woodford. Main level living at its finest. Available this Winter! The spacious 4 bedroom rancher, with walk out basement, has an open floor plan with 3 full baths, large family/dining area on the main level. The kitchen has beautiful upgraded cabinets with granite countertops and stainless steel appliances. A large pantry for your convenience. The lower level offers a large finished rec room, bedroom, full bath and ample storage area. More great features are included with this home, blinds on all finished windows garage door opener with remote, washer and dryer and many SMART home features. Reach out to hear about our closing cost assistance. * Photos, 3D tours, and videos are represent

$499,990

4 beds3 baths2,638 sq ft

133 Woodford Dr, Stephens City, VA 22655

Open floor plan • Main level living • Large pantry

(804) 510-9139

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
* * * * Builder has completed a 10x16 shed to match the house! Plenty of storage options! New Custom Built, Beautiful One-Level Craftsman style home with approximately 1600 sq feet, sits on a quiet no-thru street. It is located within walking distance to Downtown Strasburg with lots of shopping/dining and events throughout the year! You are close to the Town Park and Pool and there is NO HOA! Less than 3 miles to Interstate 81 and less than 5 miles to Interstate 66! The LP Smart Siding Engineered Wood Siding is known for it's resistance to impact and moisture! Stone foundation all the way around the home! York Heat Pump comes with a 12 Year Equipment Warranty with WIFI Thermosta

$499,000

3 beds2 baths1,600 sq ft

176 S Virginia St, Strasburg, VA 22641

9,409 sq ft lot • 2 garage spots • Built 2025

(540) 931-0144

ABOUT THIS HOME
Homes for sale under $500k in Middletown, VA
Price reduced, Assumable VA loan at 4%, Nestled in the charming Mosby Station, this exquisite Colonial home offers a perfect blend of elegance and comfort. Spanning over 2,128 sq. ft. , the interior features a traditional floor plan that invites warmth and togetherness. Enjoy cozy evenings by the glass-doored fireplace in the family room, seamlessly connected to the upgraded kitchen with premium countertops and stainless steel appliances, including a sleek built-in microwave and dishwasher. The spacious primary suite boasts a luxurious bath and a generous walk-in closet, while three additional bedrooms provide ample space for relaxation. Step outside to discover a beautifully designed deck

$480,000

4 beds2.5 baths2,128 sq ft

107 Fancy Ct, Stephens City, VA 22655

Upgraded kitchen • Premium countertops • Colonial home

(540) 374-1111

Property at 370 Poe Dr, Front Royal, VA 22630, 4 beds, 3 baths

$470,000

4 beds3 baths2,448 sq ft

370 Poe Dr, Front Royal, VA 22630

(703) 378-8810

Property at 77 Signal Knob Cottage Dr, Strasburg, VA 22657, 4 beds, 2.5 baths

$465,000

4 beds2.5 baths2,192 sq ft

77 Signal Knob Cottage Dr, Strasburg, VA 22657

(540) 686-7362

Property at 120 Bookers Crest Dr, Stephens City, VA 22655, 4 beds, 2.5 baths

$464,990

4 beds2.5 baths1,906 sq ft

120 Bookers Crest Dr, Stephens City, VA 22655

(804) 510-9139

Property at Deerfield Plan, Stephens City, VA 22655, 4 beds, 2.5 baths

$464,990

4 beds2.5 baths1,906 sq ft

Deerfield Plan, Stephens City, VA 22655

Listing provided by Zillow

Property at NEUVILLE Plan, Stephens City, VA 22655, 4 beds, 2 baths

$463,390

4 beds2 baths1,698 sq ft

NEUVILLE Plan, Stephens City, VA 22655

Listing provided by Zillow

Property at 409 Warrenfeltz, Strasburg, VA 22657, 3 beds, 3 baths

$460,000

3 beds3 baths2,285 sq ft

409 Warrenfeltz, Strasburg, VA 22657

(540) 667-9097

Property at 101 Dinges St, Stephens City, VA 22655, 4 beds, 2 baths

$449,990

4 beds2 baths1,698 sq ft

101 Dinges St, Stephens City, VA 22655

(804) 510-9139

Property at 110 April Ave, Stephens City, VA 22655, 4 beds, 3 baths

$449,900

4 beds3 baths2,974 sq ft

110 April Ave, Stephens City, VA 22655

(540) 665-0360

Property at 112 Smoke House Ct, Stephens City, VA 22655, 3 beds, 2.5 baths

$435,900

3 beds2.5 baths2,380 sq ft

112 Smoke House Ct, Stephens City, VA 22655

(540) 662-3484

Property at 59 Valley Overlook Ct, Strasburg, VA 22657, 3 beds, 3 baths

$429,900

3 beds3 baths1,568 sq ft

59 Valley Overlook Ct, Strasburg, VA 22657

(703) 378-8810

Property at 112 Jefferson Ct, Stephens City, VA 22655, 3 beds, 2 baths

$425,000

3 beds2 baths1,682 sq ft

112 Jefferson Ct, Stephens City, VA 22655

(540) 665-0360

Property at 122 Bayberry Ct, Stephens City, VA 22655, 2 beds, 2 baths

$420,000

2 beds2 baths1,448 sq ft

122 Bayberry Ct, Stephens City, VA 22655

(540) 687-6500

Property at 153 Willett Hollow St, Stephens City, VA 22655, 4 beds, 3.5 baths

$399,990

4 beds3.5 baths1,889 sq ft

153 Willett Hollow St, Stephens City, VA 22655

(804) 510-9139

Property at 161 Willett Hollow St, Stephens City, VA 22655, 4 beds, 3.5 baths

$399,990

4 beds3.5 baths1,889 sq ft

161 Willett Hollow St, Stephens City, VA 22655

(804) 510-9139

Homes for sale under $500k in Middletown

There are currently 12 homes for sale under $500k in Middletown. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middletown stay on the market for 76 days. This map is refreshed with the newest listings in Middletown every 15 minutes.

In the past month, 3 homes have been sold in Middletown. In addition to houses in Middletown, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Middletown last month. Find your dream home in Middletown 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 Middletown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middletown. Our Middletown real estate stats and trends will give you more information about home buying and selling trends in Middletown. If you're looking to sell your home in the Middletown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middletown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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