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Dreaming of a new home for the holidays? Still time to get in and with a REFRESHED price! Enjoy the ease of first-floor living in this beautifully maintained townhouse located in a sought-after 55+ community in Windham. Thoughtfully designed with comfort and convenience in mind, this home offers an open-concept floor plan, soaring vaulted ceilings, a private primary suite, and inviting sun-filled living spaces that make everyday living feel effortless. The open-concept kitchen flows seamlessly into the living room, creating the perfect space for entertaining. The private first-floor primary suite overlooks the backyard and features a spacious attached bath with a walk-in shower, creating a peaceful retreat. A versatile bonus room provides additional living space and leads to a sunroom, perfect for enjoying your morning coffee or unwinding with a good book. Step outside to the private deck and take in the tranquil surroundings. Convenient first-floor laundry and a half bath add to the home's practicality, while the attached one-car garage offers easy access and additional storage. Upstairs, you'll find a generous loft second bedroom, a full bath, and an oversized walk-in closet, making it an ideal space for guests or hobbies. The unfinished basement provides endless possibilities for storage, a workshop, home gym, or future expansion. Enjoy the benefits of a low HOA fee and access to the community clubhouse, all while being conveniently located near Windham's shopping, dining, and commuter routes. Comfort, convenience, and community await. Don't miss this exceptional opportunity!

2 Beds ⋅ 3 Baths ⋅ 5112487 MLS

Dreaming of a new home for the holidays? Still time to get in and with a REFRESHED price! Enjoy the ease of first-floor living in this beautifully maintained townhouse located in a sought-after 55+ community in Windham. Thoughtfully designed with comfort and convenience in mind, this home offers an open-concept floor plan, soaring vaulted ceilings, a private primary suite, and inviting sun-filled living spaces that make everyday living feel effortless. The open-concept kitchen flows seamlessly into the living room, creating the perfect space for entertaining. The private first-floor primary suite overlooks the backyard and features a spacious attached bath with a walk-in shower, creating a peaceful retreat. A versatile bonus room provides additional living space and leads to a sunroom, perfect for enjoying your morning coffee or unwinding with a good book. Step outside to the private deck and take in the tranquil surroundings. Convenient first-floor laundry and a half bath add to the home's practicality, while the attached one-car garage offers easy access and additional storage. Upstairs, you'll find a generous loft second bedroom, a full bath, and an oversized walk-in closet, making it an ideal space for guests or hobbies. The unfinished basement provides endless possibilities for storage, a workshop, home gym, or future expansion. Enjoy the benefits of a low HOA fee and access to the community clubhouse, all while being conveniently located near Windham's shopping, dining, and commuter routes. Comfort, convenience, and community await. Don't miss this exceptional opportunity!

33 Brookview Rd, Windham

$439,000

Welcome home to Whispering Winds, one of Windham’s premier 55+ active adult communities! Situated at 59 Pleasant St, this stunning mid-unit condo offers a thoughtful floor plan designed for effortless, one-level living paired with incredible bonus space. Step inside to an airy layout featuring soaring cathedral ceilings and rich hardwood flooring. The main living area flows seamlessly into a bright kitchen and comfortable dining area, leading out to your private backyard patio—perfect for morning coffee or outdoor relaxation. The main level offers convenience with a primary suite, full bathroom, and central air conditioning powered by efficient gas heat. Upstairs, you'll find a versatile loft area alongside additional living space ideal for a second bedroom, home office, or guest suite. Key Features & Highlights: * Spacious Living: 1,522 sq. ft. of above-grade living area across 1.5 stories with 4 rooms, 2 full bathrooms, and 1 half bath. * Bonus Space: Includes a partially finished basement for extra rec space or storage, plus an attached garage and a charming wood deck/patio. * Modern Comforts: Central A/C, forced air gas heating, and low-maintenance community utilities. * Prime Location: Peaceful setting within a highly desirable, well-maintained neighborhood. Don't miss the opportunity to enjoy relaxed, low-maintenance condo living at its finest! OPEN HOUSES THIS WEEKEND! Sat 10/17 & Sun 10/18 @ 10am-12pm

2 Beds ⋅ 3 Baths ⋅ 5112368 MLS

Welcome home to Whispering Winds, one of Windham’s premier 55+ active adult communities! Situated at 59 Pleasant St, this stunning mid-unit condo offers a thoughtful floor plan designed for effortless, one-level living paired with incredible bonus space. Step inside to an airy layout featuring soaring cathedral ceilings and rich hardwood flooring. The main living area flows seamlessly into a bright kitchen and comfortable dining area, leading out to your private backyard patio—perfect for morning coffee or outdoor relaxation. The main level offers convenience with a primary suite, full bathroom, and central air conditioning powered by efficient gas heat. Upstairs, you'll find a versatile loft area alongside additional living space ideal for a second bedroom, home office, or guest suite. Key Features & Highlights: * Spacious Living: 1,522 sq. ft. of above-grade living area across 1.5 stories with 4 rooms, 2 full bathrooms, and 1 half bath. * Bonus Space: Includes a partially finished basement for extra rec space or storage, plus an attached garage and a charming wood deck/patio. * Modern Comforts: Central A/C, forced air gas heating, and low-maintenance community utilities. * Prime Location: Peaceful setting within a highly desirable, well-maintained neighborhood. Don't miss the opportunity to enjoy relaxed, low-maintenance condo living at its finest! OPEN HOUSES THIS WEEKEND! Sat 10/17 & Sun 10/18 @ 10am-12pm

59 Pleasant St, Windham

$429,900

Your Dream Lake Escape on Shadow Lake Awaits! Seize this incredible opportunity to create a custom retreat on the highly desirable Shadow Lake. Offering 46 feet of private water frontage on the serene north side, this end-of-the-road lot is an absolute gem. A beautiful babbling brook runs down the property, enhancing the tranquil setting. Whether you choose to renovate the existing structure or completely tear down and build new, the path is clear: all state plans are already approved and available! Town permit has expired and needs approvals, but all plans will be shared. Enjoy the privacy of a large lot that abuts state land and provides plenty of parking. This peaceful waterfront location is also a commuter's dream, only 45 minutes from Boston and conveniently close to Salem's vibrant shopping, restaurants, and the Tuscan Village area. Property sold AS IS. Buyers must be accompanied by their agent and enter the existing structure at their own risk.

2 Beds ⋅ 1 Baths ⋅ 5091573 MLS

Your Dream Lake Escape on Shadow Lake Awaits! Seize this incredible opportunity to create a custom retreat on the highly desirable Shadow Lake. Offering 46 feet of private water frontage on the serene north side, this end-of-the-road lot is an absolute gem. A beautiful babbling brook runs down the property, enhancing the tranquil setting. Whether you choose to renovate the existing structure or completely tear down and build new, the path is clear: all state plans are already approved and available! Town permit has expired and needs approvals, but all plans will be shared. Enjoy the privacy of a large lot that abuts state land and provides plenty of parking. This peaceful waterfront location is also a commuter's dream, only 45 minutes from Boston and conveniently close to Salem's vibrant shopping, restaurants, and the Tuscan Village area. Property sold AS IS. Buyers must be accompanied by their agent and enter the existing structure at their own risk.

5 Allen Rd, Windham

$410,000

This pint-sized home packs a punch! Tucked away from the road on a private .46-acre lot, this charming, fully remodeled home offers the perfect blend of character, comfort, and modern updates. Step inside to discover beautiful hardwood floors, a stylish new kitchen, and an inviting living room featuring a cozy wood-burning fireplace. The covered front porch is the perfect spot to enjoy your morning coffee or unwind while taking in the peaceful surroundings. Outside, the spacious lot offers plenty of room to relax, garden, or entertain, along with a convenient storage shed. Big on charm and low on maintenance, this little gem is a fantastic alternative to condo living, offering the freedom of homeownership without the condo fees! Whether you're a first-time buyer, looking to downsize and enjoy easy single-level living, or exploring the potential for a short-term rental (subject to local regulations), this adorable Windham home offers endless possibilities. Small in size, but big on appeal -don't miss this darling home in desirable Windham.

1 Beds ⋅ 1 Baths ⋅ 5114186 MLS

This pint-sized home packs a punch! Tucked away from the road on a private .46-acre lot, this charming, fully remodeled home offers the perfect blend of character, comfort, and modern updates. Step inside to discover beautiful hardwood floors, a stylish new kitchen, and an inviting living room featuring a cozy wood-burning fireplace. The covered front porch is the perfect spot to enjoy your morning coffee or unwind while taking in the peaceful surroundings. Outside, the spacious lot offers plenty of room to relax, garden, or entertain, along with a convenient storage shed. Big on charm and low on maintenance, this little gem is a fantastic alternative to condo living, offering the freedom of homeownership without the condo fees! Whether you're a first-time buyer, looking to downsize and enjoy easy single-level living, or exploring the potential for a short-term rental (subject to local regulations), this adorable Windham home offers endless possibilities. Small in size, but big on appeal -don't miss this darling home in desirable Windham.

24a Range Rd, Windham

$299,900

BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

2 Beds ⋅ 1 Baths ⋅ 5111290 MLS

BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

17 First St, Windham

$299,900

BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

5111289 MLS

BUILDERS AND INVESTORS! Rare opportunity just steps from the community beach, boat launch, and small marina on sought-after Cobbetts Pond. Set on a 0.37-acre lot, this property is best suited for investors and builders; the existing 2-bedroom, 1-bath cottage (built 1920, approx. 798 sq ft) shows significant deferred maintenance and is not salvageable, making this essentially a lot sale with an established location in a highly desirable lake community. The lot is serviced by private well water; buyers should factor in the cost of establishing permanent utilities and confirm zoning, setback, and septic/well requirements with the Town of Windham before purchase. Surrounded by trees and open space, the property offers privacy while being part of a lakeside neighborhood. Cobbetts Pond is known for swimming, kayaking, fishing, and scenic beauty, and residents of Windham enjoy highly regarded schools, local shops and dining, and easy commuting via I-93 to Manchester, Nashua, and Boston. This is a chance to secure a foothold in the Cobbetts Pond lifestyle with land, location, and long-term potential. Buyer to perform own due diligence regarding rebuild feasibility, permitting, and lot coverage. Photos may be digitally enhanced.

17 First St, Windham

$295,000

A special piece of Vermont awaits you. Less than 12 minutes to Magic, 25 minutes to Bromley, and 35 minutes to either Okemo or Stratton. This parcel is such a varied offering, it truly has something for everyone. Peace and quiet is the first thing you will notice. Cross Road is a quiet spot off Windham Hill. There is over 1000 feet of road frontage. Choose your homesite, and your driveway will take you to your private retreat where you will not have any other houses in sight. The acreage is varied and has the type of forest diversity you might expect to find on a much larger parcel. There is a wetland at the low point at the beginning of the property where you will see visiting wildlife. As you travel up the road further, the stonewall along the road appears. The land is all woodland in various age classes of regeneration. The property is in the Current Use program where benefit is a managed forestland that will continue to provide a reduction in your property taxes. There are several species of both hardwood and softwood trees. The property is flat and sloping. Depending on where you choose to site your home, you have some great view potential. You will share the property with a variety of creatures...turkeys, deer, grouse, woodcock, fox, bear, and maybe even moose. Come see if this is the spot for you.

5111403 MLS

A special piece of Vermont awaits you. Less than 12 minutes to Magic, 25 minutes to Bromley, and 35 minutes to either Okemo or Stratton. This parcel is such a varied offering, it truly has something for everyone. Peace and quiet is the first thing you will notice. Cross Road is a quiet spot off Windham Hill. There is over 1000 feet of road frontage. Choose your homesite, and your driveway will take you to your private retreat where you will not have any other houses in sight. The acreage is varied and has the type of forest diversity you might expect to find on a much larger parcel. There is a wetland at the low point at the beginning of the property where you will see visiting wildlife. As you travel up the road further, the stonewall along the road appears. The land is all woodland in various age classes of regeneration. The property is in the Current Use program where benefit is a managed forestland that will continue to provide a reduction in your property taxes. There are several species of both hardwood and softwood trees. The property is flat and sloping. Depending on where you choose to site your home, you have some great view potential. You will share the property with a variety of creatures...turkeys, deer, grouse, woodcock, fox, bear, and maybe even moose. Come see if this is the spot for you.

Cross Rd, Windham

$295,000

Rare opportunity to build in Windham! This fully approved 1.95 acre building lot offers a private, wooded setting with the homesite tucked well back from Goodhue Road. A long private drive leads into a wider rear portion of the property, creating an ideal setting for a new home surrounded by mature woods and separation from the road. Much of the upfront work has already been completed, making this an excellent opportunity for a builder or buyer looking to move directly toward construction. Approved survey, subdivision plans and engineered plans are included with the sale. The approved plans provide for private well and septic, with the proposed homesite positioned toward the rear of the property. Located along the Windham/Derry line, the property combines a secluded residential setting with convenient access to Windham's schools, shopping, dining and major commuting routes. A unique opportunity to secure an approved homesite in the Windham School District without starting the lengthy subdivision and engineering process from scratch. Plans and approvals available for review. Buyer and buyer's agent to perform their own due diligence and independently verify all approvals, dimensions, acreage, school assignment, municipal requirements and intended use. Listing party holds an equitable interest in the property pursuant to a purchase and sale agreement and is marketing its contractual interest. Transaction may be completed through an assignment of contract and/or simultaneous closing. Listing party does not currently hold legal title to the property.

5110039 MLS

Rare opportunity to build in Windham! This fully approved 1.95 acre building lot offers a private, wooded setting with the homesite tucked well back from Goodhue Road. A long private drive leads into a wider rear portion of the property, creating an ideal setting for a new home surrounded by mature woods and separation from the road. Much of the upfront work has already been completed, making this an excellent opportunity for a builder or buyer looking to move directly toward construction. Approved survey, subdivision plans and engineered plans are included with the sale. The approved plans provide for private well and septic, with the proposed homesite positioned toward the rear of the property. Located along the Windham/Derry line, the property combines a secluded residential setting with convenient access to Windham's schools, shopping, dining and major commuting routes. A unique opportunity to secure an approved homesite in the Windham School District without starting the lengthy subdivision and engineering process from scratch. Plans and approvals available for review. Buyer and buyer's agent to perform their own due diligence and independently verify all approvals, dimensions, acreage, school assignment, municipal requirements and intended use. Listing party holds an equitable interest in the property pursuant to a purchase and sale agreement and is marketing its contractual interest. Transaction may be completed through an assignment of contract and/or simultaneous closing. Listing party does not currently hold legal title to the property.

Goodhue Road, Windham

$279,900

Welcome to low-maintenance living in desirable Windham! This beautifully kept 2-bedroom, 1-bathroom garden-style condo at Country Manor offers an ideal blend of comfort, privacy, and convenience. Step inside to a sun-filled layout featuring a full kitchen, spacious living room, full bathroom, and generous closet space throughout. Enjoy easy single-level living on the first floor with direct access to your private deck, perfect for relaxing in a quiet, country-like setting at the end of a dead-end street. Standout features include an assigned space in the shared heated garage underneath, an additional dedicated outdoor parking spot, private in-unit laundry, and locked basement storage. The low-stress condo lifestyle gets even better: the low monthly condo fee covers heat, hot water, water/sewer, trash, snow removal, and grounds maintenance. Commuters will love the convenient access to I-93, Route 111, local shopping, and dining. Move right in and make this Windham home yours!

2 Beds ⋅ 1 Baths ⋅ 5113582 MLS

Welcome to low-maintenance living in desirable Windham! This beautifully kept 2-bedroom, 1-bathroom garden-style condo at Country Manor offers an ideal blend of comfort, privacy, and convenience. Step inside to a sun-filled layout featuring a full kitchen, spacious living room, full bathroom, and generous closet space throughout. Enjoy easy single-level living on the first floor with direct access to your private deck, perfect for relaxing in a quiet, country-like setting at the end of a dead-end street. Standout features include an assigned space in the shared heated garage underneath, an additional dedicated outdoor parking spot, private in-unit laundry, and locked basement storage. The low-stress condo lifestyle gets even better: the low monthly condo fee covers heat, hot water, water/sewer, trash, snow removal, and grounds maintenance. Commuters will love the convenient access to I-93, Route 111, local shopping, and dining. Move right in and make this Windham home yours!

6 Colonial Rd Unit 1, Windham

$225,000

This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Home will need a new septic system. If you have been looking for a true Vermont getaway, this property delivers!

2 Beds ⋅ 1 Baths ⋅ 5085393 MLS

This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Home will need a new septic system. If you have been looking for a true Vermont getaway, this property delivers!

51 Golding Rd, Windham