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Guest house builders in Winchester

Avatar for Hernandez Landscaping
Hernandez Landscaping
2.33(
3
)
Approved Pro
Hernandez Landscaping
2.33(
3
)
Approved Pro
963 local quotes requested
3 years of experience

We focus on all kind of projects, big or small. We do your traditional Landscaping such as cut grass, trim bushes/trees, pull weeds. We also work on bigger projects like creating new back or front yards and patios, and all kind of cement work. We work all year around and do our best to give the customers the best affordable price out there. We shovel during the winters and paint all year around, as well as much more.

"We do not recommend Hernanadez Landscaping. After at least 3 requests to for a written estimate, including the night before the project (we had to call for the arrival time), it was never provided. Red Flags! Jerry claims he sent it via the Angi app, and that he isn't given any personal contact information. However, he had previously asked for and gotten my personal email. When he first came to give an oral estimate, we liked the crew and agreed that they would install a walkway that matched the pavers of a connecting walkway, remove some trees and a brush pile, and clean the patio. When they arrived to start, we were told they didn't have the matching pavers. When we spoke with Jerry on the phone, it seemed he wasn't entirely sure which job was ours. At this point we cancelled the walkway project but asked him to do the other part of the job. The next thing we knew, the crew was packing up to leave. Jerry took no responsibility for the problems. One star is for the nice crew."

Carolyn R on May 2025

We focus on all kind of projects, big or small. We do your traditional Landscaping such as cut grass, trim bushes/trees, pull weeds. We also work on bigger projects like creating new back or front yards and patios, and all kind of cement work. We work all year around and do our best to give the customers the best affordable price out there. We shovel during the winters and paint all year around, as well as much more.

"We do not recommend Hernanadez Landscaping. After at least 3 requests to for a written estimate, including the night before the project (we had to call for the arrival time), it was never provided. Red Flags! Jerry claims he sent it via the Angi app, and that he isn't given any personal contact information. However, he had previously asked for and gotten my personal email. When he first came to give an oral estimate, we liked the crew and agreed that they would install a walkway that matched the pavers of a connecting walkway, remove some trees and a brush pile, and clean the patio. When they arrived to start, we were told they didn't have the matching pavers. When we spoke with Jerry on the phone, it seemed he wasn't entirely sure which job was ours. At this point we cancelled the walkway project but asked him to do the other part of the job. The next thing we knew, the crew was packing up to leave. Jerry took no responsibility for the problems. One star is for the nice crew."

Carolyn R on May 2025


Avatar for Pegasus Design-To-Build  LLC
Pegasus Design-To-Build LLC
727 Main St
4.66(
123
)
Approved Pro
Pegasus Design-To-Build LLC
727 Main St
4.66(
123
)
Approved Pro
Customers say: Quality work
142 local quotes requested
24 years of experience

A Boston area full service design/build remodeling firm offering planning and construction of kitchens, additions and other quality home renovations. Visit www.pegdesign.net/portfolio to see more of our projects!

"Everything went well except for the painting of the kitchen. My 2 year old could have done a better job"

Brian H on July 2020

A Boston area full service design/build remodeling firm offering planning and construction of kitchens, additions and other quality home renovations. Visit www.pegdesign.net/portfolio to see more of our projects!

"Everything went well except for the painting of the kitchen. My 2 year old could have done a better job"

Brian H on July 2020


B LaGrassa Construction
282 South Road
5.00(
3
)
Approved Pro
B LaGrassa Construction
282 South Road
5.00(
3
)
Approved Pro
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
281 local quotes requested

B Lagrassa Construction is your one stop shop for all remodeling, decks and home improvement needs. We pride ourselves on quality work, fair pricing and customer satisfaction on every project...we will treat your home like our own. Give us a call today to schedule your free home estimate and ask all the questions you need answers for regarding your dream project. We are licensed and insured for your protection and look forward to adding you to our long list of happy customers!

"Amazing! Punctual and very clean. So happy with our basement remodel!"

ann m on January 2025

B Lagrassa Construction is your one stop shop for all remodeling, decks and home improvement needs. We pride ourselves on quality work, fair pricing and customer satisfaction on every project...we will treat your home like our own. Give us a call today to schedule your free home estimate and ask all the questions you need answers for regarding your dream project. We are licensed and insured for your protection and look forward to adding you to our long list of happy customers!

"Amazing! Punctual and very clean. So happy with our basement remodel!"

ann m on January 2025


Avatar for Allied Builders Group
Allied Builders Group
10 Willams Street
5.00(
18
)
Approved Pro
Allied Builders Group
10 Willams Street
5.00(
18
)
Approved Pro
Customers say: True professional
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
263 local quotes requested

Allied Group is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customer's interests, and make their concerns the basis of our business. General Contractor

"They were great! The workers were prompt, easy to work with, hard working and did beautiful work. I would recommend them to anyone who is looking for a reliable company to work with."

Ellen A on January 2025

Allied Group is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customer's interests, and make their concerns the basis of our business. General Contractor

"They were great! The workers were prompt, easy to work with, hard working and did beautiful work. I would recommend them to anyone who is looking for a reliable company to work with."

Ellen A on January 2025


Avatar for SRS Construction & Landscape
SRS Construction & Landscape
92 Bishop St
5.00(
20
)
Approved Pro
SRS Construction & Landscape
92 Bishop St
5.00(
20
)
Approved Pro
Customers say: True professional
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
381 local quotes requested

Welcome! Uproot problems with your landscape for a more pleasing, unique property with superior services from in Metro West area . SRS Construction & Landscape specializes in landscaping services and maintenance that make your property look its best year-round. We are a full-service landscaping company that handles all of your property needs. SRS Construction & Landscape has been keeping grass greener, flowers more vibrant, and clients happier. Contact us now to become one of the many satisfied property owners we've helped throughout the years. No matter whether it is a small or large project, our expertise will enhance the look and value of your property. Call us in Metro West today for a personal consultation. Our Services Include the Following : Spring e Falls Cleanups , Landscape design, Landscape Installation ,General Maintenance , Lawn Mowing , Fertilization Program, Shrub Trimming , Irrigation System , Sprinkler Systems , Patios and Walkways , Stone And Brick , Blue stone , Cobblestone , Steps , Pool Patio , And many More. Call us today For Free Estimate At 508 494 4858. Our office hours are:7:00 am to 6:00 pm

"I’m very impressed while working with the SRS Contruction & Landscape team. They showed up right away to assess my needs, listened carefully to my ideas, and offered helpful suggestions. Throughout the process, the team was friendly, flexible, and ready to accommodate my requests. To top it off, their pricing was more competitive than any other contractor I contacted. I highly recommend SRS Construction & Landscape for this smooth, professional and pleasant experience."

Liwei L on March 2025

Welcome! Uproot problems with your landscape for a more pleasing, unique property with superior services from in Metro West area . SRS Construction & Landscape specializes in landscaping services and maintenance that make your property look its best year-round. We are a full-service landscaping company that handles all of your property needs. SRS Construction & Landscape has been keeping grass greener, flowers more vibrant, and clients happier. Contact us now to become one of the many satisfied property owners we've helped throughout the years. No matter whether it is a small or large project, our expertise will enhance the look and value of your property. Call us in Metro West today for a personal consultation. Our Services Include the Following : Spring e Falls Cleanups , Landscape design, Landscape Installation ,General Maintenance , Lawn Mowing , Fertilization Program, Shrub Trimming , Irrigation System , Sprinkler Systems , Patios and Walkways , Stone And Brick , Blue stone , Cobblestone , Steps , Pool Patio , And many More. Call us today For Free Estimate At 508 494 4858. Our office hours are:7:00 am to 6:00 pm

"I’m very impressed while working with the SRS Contruction & Landscape team. They showed up right away to assess my needs, listened carefully to my ideas, and offered helpful suggestions. Throughout the process, the team was friendly, flexible, and ready to accommodate my requests. To top it off, their pricing was more competitive than any other contractor I contacted. I highly recommend SRS Construction & Landscape for this smooth, professional and pleasant experience."

Liwei L on March 2025


Avatar for All Work Construction INC.
All Work Construction INC.
183 Londonderry Tpke
New on HomeAdvisorNew on Angi
Approved Pro
All Work Construction INC.
183 Londonderry Tpke
New on AngiNew on HomeAdvisor
Approved Pro
961 local quotes requested
25 years of experience

All Work Construction is proudly the #1 Home Improvement Company for Hooksett NH and beyond. We specialize in bathroom remodeling, kitchen remodeling, exteriors such as vinyl siding, shingle roof replacement, replacement windows, and exterior doors. Contact us today to request our home remodeling services. We offer free estimate consultations! (We serve NH, Northern MA, and partial ME)

All Work Construction is proudly the #1 Home Improvement Company for Hooksett NH and beyond. We specialize in bathroom remodeling, kitchen remodeling, exteriors such as vinyl siding, shingle roof replacement, replacement windows, and exterior doors. Contact us today to request our home remodeling services. We offer free estimate consultations! (We serve NH, Northern MA, and partial ME)


Avatar for Affordable Landscaping
Affordable Landscaping
61 Crimson Rd
4.21(
97
)
Approved Pro
Affordable Landscaping
61 Crimson Rd
4.21(
97
)
Approved Pro
Customers say: Quality work
541 local quotes requested
34 years of experience

We are an award winning woman owned business here to help address your landscaping needs with a women’s touch. We specialize in high end and affordable landscape design & construction. We believe that your back yard is our back yard! As a true full-service landscaper we are committed to providing home and business owners with the highest quality landscaping services at affordable rates. Serving Billerica, Tewksbury, Chelmsford, Burlington, Wilmington, Bedford and LANDSCAPING/HARDSCAPING- Merrimack Valley

"Lisa and team were amazing to work with … and they did it AGAIN! This is the second big project I have done with Affordable Landscape and they executed this work efficiently and effectively I asked them to give me ideas for a patio and fire pit … final product is a genuine backyard oasis for my family and I to enjoy. They offered creative ideas in their design as the lot wasn’t the easiest to work with. I’m Super happy with the final product and can’t say enough about their work ethic, kindness, professionalism and art ! Thank you Lisa and team!"

Christine C on August 2024

We are an award winning woman owned business here to help address your landscaping needs with a women’s touch. We specialize in high end and affordable landscape design & construction. We believe that your back yard is our back yard! As a true full-service landscaper we are committed to providing home and business owners with the highest quality landscaping services at affordable rates. Serving Billerica, Tewksbury, Chelmsford, Burlington, Wilmington, Bedford and LANDSCAPING/HARDSCAPING- Merrimack Valley

"Lisa and team were amazing to work with … and they did it AGAIN! This is the second big project I have done with Affordable Landscape and they executed this work efficiently and effectively I asked them to give me ideas for a patio and fire pit … final product is a genuine backyard oasis for my family and I to enjoy. They offered creative ideas in their design as the lot wasn’t the easiest to work with. I’m Super happy with the final product and can’t say enough about their work ethic, kindness, professionalism and art ! Thank you Lisa and team!"

Christine C on August 2024


Avatar for Long Home Products
Long Home Products
300 Myles Standish Blvd
2.76(
21
)
Approved Pro
Long Home Products
300 Myles Standish Blvd
2.76(
21
)
Approved Pro
6060 local quotes requested
80 years of experience

With over 70 years of experience in home improvement, Long Home Products is the industry-leading company you can trust to give you peace of mind. We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We are experts in all aspects of roofing, bathroom, window and door projects. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guarantee your satisfaction!

"Ayden was very kind and insightful. I was happy to meet an incredible worker like that from Long Home."

Alayna L on April 2025

With over 70 years of experience in home improvement, Long Home Products is the industry-leading company you can trust to give you peace of mind. We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We are experts in all aspects of roofing, bathroom, window and door projects. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guarantee your satisfaction!

"Ayden was very kind and insightful. I was happy to meet an incredible worker like that from Long Home."

Alayna L on April 2025


Avatar for DS General Services Corp.
DS General Services Corp.
5 Clearview Drive
5.00(
6
)
Approved Pro
DS General Services Corp.
5 Clearview Drive
5.00(
6
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
336 local quotes requested

We offer bathroom, kitchen and basement remodeling, deck build, hardwood floor installation, interior painting, tile. We do not claim perfection, but we promise pride, quality and perseverance. Over 20 years in business.

"Extremely satisfied with project from start to finish. In my opinion communication is always the key to all successful projects, DS General Services excelled in this area. All calls and questions were returned and addressed in a prompt response. Wellington DaSilva and his team were courteous, clean and professional. My wife and I are extremely happy with our new walk in shower and will definitely reach out to DS General Services for any future projects."

Dennis M on March 2024

We offer bathroom, kitchen and basement remodeling, deck build, hardwood floor installation, interior painting, tile. We do not claim perfection, but we promise pride, quality and perseverance. Over 20 years in business.

"Extremely satisfied with project from start to finish. In my opinion communication is always the key to all successful projects, DS General Services excelled in this area. All calls and questions were returned and addressed in a prompt response. Wellington DaSilva and his team were courteous, clean and professional. My wife and I are extremely happy with our new walk in shower and will definitely reach out to DS General Services for any future projects."

Dennis M on March 2024


Avatar for Busy-Bee Construction LLC
Busy-Bee Construction LLC
151 North Ave
4.80(
99
)
Approved Pro
Busy-Bee Construction LLC
151 North Ave
4.80(
99
)
Approved Pro
Customers say: Super punctual
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
192 local quotes requested

Our company is your best source for professional, value driven, low cost service. Meaning that we are able to provide the most value and innovation per your dollar spent. We are a design build company with 25 years experience in all aspects of the construction industry, unlike most contractors that only specialize in one field and sub out the rest of the work to the lowest bidders; ultimately resulting in a lower quality of work. Busy Bee Construction only employs dependable and experienced craftsman to insure top quality work, and to prove it we offer a one year workmanship warranty. So whether your project is as small as a bathroom or as large as a new constructed home we can make it a stress free and exciting experience for you. Please visit busy-beeconstruction.com to find out more about our company and see photos. Additional email contact: downie.john@comcast.net

"I can't say enough about John, Gary, and the team at Busy Bee Construction. They took on a big project transforming my horror of an overly-large primary bathroom into a beautiful, new bathroom plus an additional study. They were clear, communicative, and knowledgeable, and they did exceptional work at a very fair price. I would absolutely work with them again (and definitely will!). These guys are the real deal."

Kelly W on November 2024

Our company is your best source for professional, value driven, low cost service. Meaning that we are able to provide the most value and innovation per your dollar spent. We are a design build company with 25 years experience in all aspects of the construction industry, unlike most contractors that only specialize in one field and sub out the rest of the work to the lowest bidders; ultimately resulting in a lower quality of work. Busy Bee Construction only employs dependable and experienced craftsman to insure top quality work, and to prove it we offer a one year workmanship warranty. So whether your project is as small as a bathroom or as large as a new constructed home we can make it a stress free and exciting experience for you. Please visit busy-beeconstruction.com to find out more about our company and see photos. Additional email contact: downie.john@comcast.net

"I can't say enough about John, Gary, and the team at Busy Bee Construction. They took on a big project transforming my horror of an overly-large primary bathroom into a beautiful, new bathroom plus an additional study. They were clear, communicative, and knowledgeable, and they did exceptional work at a very fair price. I would absolutely work with them again (and definitely will!). These guys are the real deal."

Kelly W on November 2024

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FAQs for guest house building service projects in Winchester, MA

The standard construction timeline for a villa ranges from eight to 18 months, depending on its complexity and size. Factors affecting this schedule include architectural intricacy, permitting processes, seasonal construction limitations, and material availability. Custom luxury villas with specialized features require additional time for proper execution. Planning and design phases preceding actual construction can add several months to the overall project timeline.

Many villa projects encounter issues from inadequate budgeting that fails to account for contingencies and upgrades. Poor contractor selection based primarily on low bids often leads to quality issues and timeline delays. Insufficient attention to foundation and site preparation can lead to structural problems throughout the building's lifespan. Frequent design modifications during construction significantly increase costs and extend timelines, while overlooking energy efficiency considerations impacts long-term operating expenses.

Villas incorporate more sophisticated architectural elements, requiring specialized construction techniques. Their emphasis on indoor-outdoor living spaces demands thoughtful integration of structural and aesthetic considerations. Many villa designs incorporate luxury amenities that require specialized installation expertise. Local building codes may impose additional requirements for villas in certain communities, particularly those with architectural review boards or historical preservation guidelines.

This decision depends on current real estate market conditions, available inventory, and your specific preferences. Existing villas offer immediate occupancy and established landscaping but may require renovations to meet current tastes. New construction provides complete customization and modern systems, but it involves longer timelines and potential construction challenges. The premium for new construction varies significantly by location, with some markets offering minimal price differences while others show substantial gaps.

Villa maintenance requirements depend largely on size, materials, and included amenities. Exterior elements, such as gardens, pools, and architectural details, require regular upkeep. Major systems, including HVAC, roofing, and plumbing, benefit from preventative maintenance programs. Establishing relationships with reliable service providers helps manage these ongoing requirements efficiently and economically.

The Winchester, MA homeowners’ guide to guest house building services
From average costs to expert advice, get all the answers you need to get your job done.
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