20

Windham, CT Homes for Sale under $500,000

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  • /10

    $249,900

    • Land
    • 25.7 Acres
    • $9,724 per Acre

    220 Plains Rd, Windham, CT 06280

    Wonderful potential development opportunity. Road frontage on 2 roads, approximately 1350' of frontage on Plains Rd., and approximately 450' of frontage on Anna Maria Ln., and existing cul-du-sac subdivision. Possible 7-8 lots subdivision to be created.

    Agent Photo

    Rick Nassiff

    KW Legacy Partners

    220 Plains Rd, Windham, CT 06280
  • /2

    $299,900

    • 6 Beds
    • 3 Baths
    • 2,700 Sq Ft

    14 Carey St, Willimantic, CT 06226

    Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive.

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    14 Carey St, Willimantic, CT 06226
  • /40

    $319,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,379 Sq Ft

    130 Windham Rd, Willimantic, CT 06226

    If you're looking for a spacious investment property or a home where you can add your own personal touches, this could be the one! Ideally located close to Eastern Connecticut State University, this 4-bedroom Colonial offers excellent potential as a housing investment, especially with a separate in-law apartment. The home features generously sized rooms, beautiful wood floors, some updated

    Lisa Perry CR Premier Properties

    130 Windham Rd, Willimantic, CT 06226
  • /40

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,856 Sq Ft

    415 Jerusalem Rd, Windham, CT 06280

    Pristine property with one floor living and enough room for all! Beautiful updated kitchen with breakfast bar, granite counters and access to the back deck perfect for all your gatherings by the pool or firepit. Amazing primary bedroom suite with hardwood floors, cathedral ceiling, sitting area, walk-in closet, full bath with whirlpool tub and access to your own private office. The remaining

    Rick Loranger Coldwell Banker Realty

    415 Jerusalem Rd, Windham, CT 06280
  • /40

    $274,900

    • 4 Beds
    • 2 Baths
    • 1,648 Sq Ft

    27 Gamache Ln, North Windham, CT 06256

    Offered for the first time in 24 years and loaded with high-ticket updates, this spacious 1648 ft.2 Cape Cod offers four bedrooms, two full baths, and is set on a private .61 acre lot in a small neighborhood! Over the past 12 years, the seller performed substantial updates including a new metal roof, installed a new central air system with new ductwork, converted from oil to propane, added a high

    James Burnett Eagle Eye Realty PLLC

    27 Gamache Ln, North Windham, CT 06256
  • /40

    $365,000

    • 3 Beds
    • 2 Baths
    • 2,318 Sq Ft

    207 Summit St, Willimantic, CT 06226

    Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring

    Sue Esposito Home Selling Team

    207 Summit St, Willimantic, CT 06226
  • /26

    $439,000

    $4K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 1,787 Sq Ft

    7 Devotion Rd, Windham, CT 06280

    Nestled in the peaceful, rural charm of Scotland, CT, this lovingly updated 9-room, 4-bedroom, 2-bathroom home delivers the perfect blend of comfort, character, and modern convenience. From the moment you arrive, you'll feel the embrace of home - and see endless opportunities for family life here. This home is ready for your life to unfold - from quiet weekday mornings to lively gatherings. Step

    Alexia Andrade US Asset Realty

    7 Devotion Rd, Windham, CT 06280
  • /17

    $479,000

    $1K PRICE DROP
    • 9 Beds
    • 4 Baths
    • 2,939 Sq Ft

    260 Summit St, Windham, CT 06226

    Opportunity awaits with this multi-family property in Willimantic. Featuring multiple residential units with a mix of layouts, this property offers flexibility for both investors and owner-occupants seeking rental income. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks, public transportation, and major commuter routes. Separate living spaces provide

    Michelle Mandel Carl Guild & Associates

    260 Summit St, Windham, CT 06226
  • /14

    $324,900

    • 3 Beds
    • 1 Bath
    • 804 Sq Ft

    14 Tunxis Ln, Willimantic, CT 06226

    Welcome to 14 Tunxis Lane! This well-maintained 3-bedroom, 1-bathroom home is move-in ready and offers a wonderful opportunity for its next owner. Recent improvements include newer windows, a new front entry door, and refreshed landscaping, enhancing both curb appeal and functionality. Situated near a quiet cul-de-sac, the property offers a peaceful and private setting with a spacious back and

    Justin Marino Marino Realty LLC

    14 Tunxis Ln, Willimantic, CT 06226
  • /17

    $290,000

    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    86 Chestnut St, Willimantic, CT 06226

    INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered

    Marcus Hamilton CENTURY 21 Shutters & Sails

    86 Chestnut St, Willimantic, CT 06226
  • /20

    $210,000

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 998 Sq Ft

    29 Kathleen Dr Unit 5C, Willimantic, CT 06226

    Move-in ready 2-bedroom, 1.5-bath townhouse-style condo offering comfortable, low-maintenance living in a desirable community. The main level features a spacious living room, a kitchen with updated appliances, designated dining area and a convenient half bath. Upstairs are two generously sized bedrooms and a full bathroom. The full basement provides abundant storage, washer and dryer hookups, and

    Brittany Kimlingen First Choice Realty

    29 Kathleen Dr Unit 5C, Willimantic, CT 06226
  • /40

    $285,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,324 Sq Ft

    3 Bristol St, Willimantic, CT 06226

    Welcome to 3 Bristol St! Tucked away in a quiet Windham neighborhood, this well cared for home is a gardeners dream! Surrounded by established perennial gardens and fruit trees, the property offers a peaceful, tranquil setting while remaining just minutes from downtown and University areas. The flexible floor plan provides plenty of options, including an office that could easily be another

    Kathy Geryk Coldwell Banker Realty

    3 Bristol St, Willimantic, CT 06226
  • /34

    $350,000

    $25K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,228 Sq Ft

    15 Cracow Ave, Windham, CT 06280

    Move-in ready, single-level living meets your own private backyard retreat at 15 Cracow Avenue. This well-maintained 3-bedroom, 2-full-bath ranch offers the convenience buyers are searching for, with all three bedrooms and both full bathrooms located on the main living level. Inside, an open and inviting layout is highlighted by hardwood flooring, a wood-burning fireplace, and an updated kitchen

    AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

    15 Cracow Ave, Windham, CT 06280
  • /32

    $275,000

    $100K PRICE DROP
    • 7 Beds
    • 4 Baths
    • 3,963 Sq Ft

    129 Valley St, Windham, CT 06226

    Mixed-use investment property with multiple income streams and strong value-add potential. The property is zoned B-1A and currently configured with two occupied residential units generating income, plus two additional gutted residential units with plumbing in place, ready for build-out. The property also includes a commercial storefront with a separate entrance, offering flexibility for a variety

    Kyle West eXp Realty

    129 Valley St, Windham, CT 06226
  • /40

    $310,000

    • 5 Beds
    • 2 Baths
    • 1,488 Sq Ft

    134 Lauter Ave, Willimantic, CT 06226

    Charming One-Level Living Ranch Welcome to this delightful ranch-style home, perfectly situated on a serene, private lot adorned with beautiful fruit trees and a garden area. This residence offers the convenience of one-level living with a host of appealing updates. The main level features a modernized kitchen that flows seamlessly into a bright and airy living room, accentuated by abundant

    Jeanne Crum Home Selling Team

    134 Lauter Ave, Willimantic, CT 06226
  • /28

    $380,000

    Open Fri 5PM - 7PM $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,158 Sq Ft

    187 Tuckie Rd, North Windham, CT 06256

    Welcome to your own retreat! Perfectly positioned on a gorgeous, level 1 acre lot surrounded by mature trees, this beautifully maintained Cape offers the peaceful lifestyle you've been dreaming of. From the moment you arrive, you'll picture slow mornings spent on the charming front porch w/a cup of coffee and your favorite book, soaking in the quiet beauty that surrounds you. Out back, you'll

    Meghan Wininger Real Broker CT, LLC

    187 Tuckie Rd, North Windham, CT 06256
  • /15

    $215,000

    • 2 Beds
    • 1.5 Baths
    • 998 Sq Ft

    29 Kathleen Dr Unit 7E, Willimantic, CT 06226

    Welcome to this well maintained 2 bedroom, 1.5 bathroom condo in the peaceful Elm Tree Village community. With a living room that flows into the dining area, this home features a functional layout designed for easy living. The private deck is perfect for relaxing and enjoying the weather. There is also an attached garage and a basement offering ample storage space. Come add your touches and make

    Shacara Cook KW Legacy Partners

    29 Kathleen Dr Unit 7E, Willimantic, CT 06226
  • /19

    $219,000

    $19K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,078 Sq Ft

    129 Walnut St, Willimantic, CT 06226

    Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a

    Lisa Therecka Therecka & Associates LLC

    129 Walnut St, Willimantic, CT 06226
  • /38

    $385,000

    • 4 Beds
    • 1 Bath
    • 1,478 Sq Ft

    17 Buckingham Rd, Mansfield Center, CT 06250

    Welcome to this well-maintained 4-bedroom Cape Cod-style home, peacefully situated at the end of a quiet street. Well maintained and thoughtfully upgraded, this home offers comfort, functionality, and peace of mind. The heated breezeway provides a welcoming entrance and convenient access to the attached garages. The spacious kitchen offers plenty of room for cooking and entertaining and features

    Lisa Barstow Simply Sold Real Estate

    17 Buckingham Rd, Mansfield Center, CT 06250
  • /36

    $419,900

    $30K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,887 Sq Ft

    13 Bates Rd, Chaplin, CT 06235

    Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

    Kristen Merrill Countryside Realty

    13 Bates Rd, Chaplin, CT 06235

Home Price Trends

Median Sale Price
$369,900
Median Single Family Sale Price
$368,950
Median Townhouse Sale Price
$505,000
Median 2 Bedroom Sale Price
$199,000
Average Price Per Sq Ft
$219
Number of Homes for Sale
5
Last 12 months Home Sales
45
Months of Supply
1.30
Median List Price
$382,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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